Способ получения 1,2-пропиленгликоля из глицерина

Настоящее изобретение относится к способу получения 1,2-пропиленгликоля гидрированием глицерина при повышенных давлении и температуре в присутствии медьсодержащего катализатора в реакторе. При этом процесс проводят при давлении 20-30 атм в трехфазном реакторе при подаче глицерина и водорода в верхнюю часть реактора, при этом глицерин течет по поверхности частиц катализатора при удельном расходе 0,20-0,70 1/ч, расход водорода устанавливают на таком уровне, чтобы степень его конверсии находилась в интервале 50-90%. Предлагаемый способ позволяет получать 1,2-пропиленгликоль с высокой селективностью при минимальной подаче водорода и без использования дополнительного растворителя. 4 з.п. ф-лы, 1 табл., 12 пр.

СПОСОБ СОВМЕСТНОГО ПОЛУЧЕНИЯ ИЗОПРЕНА И ДИМЕТИЛВИНИЛКАРБИНОЛА

Изобретение относится к области нефтехимического синтеза, к способам получения изопрена и диметилвинилкарбинола, ценных продуктов для получения каучуков и витаминов. Цель - повышение производительности и увеличение выхода целевых продуктов. Получение ведут обработкой 4,4-диметил-1,3-диоксана изобутиленом и/или триметилкарбинолом в воде при 70 - 100С и давлении 10 - 18 атм в присутствии катализатора смеси фосфорной кислоты и азотнокислой меди (II) в мольном соотношении компонентов 1 : 0,001 - 0,2. Затем реакционную смесь дросселируют до атмосферного давления и перегоняют, отбирая фракцию 34 - 97С, содержащую целевые продукты. Способ позволяет повысить конверсию 4,4-диметил-1,3-диоксана на 5 - 7% и увеличить селективность превращения 4,4-диметил-1,3-диоксана в изопрен и диметилвинилкарбинол на 6 - 8 мол.%, исключить забивку оборудования смолами.

Способ получения ендииновых спиртов алициклического ряда

Способ получения производных 2-алкилглицерина

Способ получения амидов бифенилмасляной кислоты

Способ получения 4-(4-бифенилил)1-бутанола

Способ получения изопрена

Способ получения смеси, содержащей 60-90 вес. % родинола и 40-10 вес. % цитронеллола

СПОСОБ ПОЛУЧЕНИЯ 4-

HYDRIERUNG VON GLYCERIN

Verfahren zur Darstellung ungesaettigter Alkohole

VERFAHREN ZUR HERSTELLUNG VON NORPATCHOULENOL

Riechstoffkompositionen

PROCESS FOR THE DEHYDRATION OF DIOLS

... 1355704 Pyrophosphates COMPAGNIE FRANCAISE DE RAFFINAGE 19 April 1971 [16 April 1970] 27244/71 Heading C1A [Also in Divisions B1 C2 and C5] The Specification gives details relating to methods for preparing material which comprises at least one neutral pyrophosphate of at least one metal selected from lithium, sodium, strontium and barium and, optionally, at least one neutral orthophosphate of at least one metal selected from lithium, sodium, strontium and barium, which material may be used as catalyst in the dehydration of vicinal and non-vicinal diols. The neutral pyrophosphate may be a simple pyrophosphate, i.e. containing only one cationic metal, or a complex pyrophosphate, i.e. containing two or more cationic metals. As exemplified, lithium sodium double pyrophosphate, Li 3 NaP 2 O 7 , is prepared by combining a hot aqueous solution of sodium pyrophosphate decahydrate with a hot solution of lithium chloride, nitrate, acetate or hydroxide, drying the resulting precipitate at 110‹ C.

Aliphatic Alcohol, Ester and Aldehyde Odorants

... 1,167,776. Perfumes. L. GIVAUDAN & GIE S.A. 3 Aug., 1967 [3 Aug., 1966], No. 35795/67. Heading A5B. [Also in Division C2] Perfume compositions contain besides conventional perfume ingredients, compounds of formula: wherein R1 is C 1-4 alkyl, R2 is C 1-5 alkyl or Ph [or R1-R2 is -(CH 2 ) 4-5 -], R3 is Me or Et, and R4 is CHO (possibly acetalised), CH 2 OH or its carboxylic-acid-derived acylate, as well as their #5- and #6- dehydro derivatives, and their 6-hydroxy derivatives.

TETRAFLUOROTEREPHTHALYL ALCOHOL ESTERS THEREOF AND A PROCESS FOR THEIR PREPARATION

IMPROVED CATALYTIC HYDROGENOLYSIS OF ALDITOLS TO PRODUCE POLYOLS

Process

Method of preparation of active derivatives of acetic acid.

Weedkillers compositions.

VERFAHREN ZUR HERSTELLUNG VON NEUEN ALKALISALZEN VON DAILKYLPROPIONSAUREN

VERFAHREN ZUR HERSTELLUNG NEUER (4-BIPHENYLYL) -ALKOHOLE

PROCEDURE FOR THE PRODUCTION OF ACROLEIN

Method and apparatus for catalytic conversion of a composition

Verfahren, Vorrichtung, Katalysator und Verfahren zur Herstellung eines Katalysators zur katalytischen Umwandlung einer Stoffmischung enthaltend Glycerin in Propanole in einem Festbettreaktor (2), wobei Substrate des Katalysators anorganische Materialien und/oder Metalloxide aufweisen, dadurch gekennzeichnet, dass die Substrate einen Porendurchmesser an der Oberfläche zwischen 10 und 25 Ångström, bevorzugt zwischen 12 und 20 Ångström, besonders bevorzugt im Wesentlichen von 15 Ångström aufweisen.

PROCEDURE FOR the PRODUCTION of NEW (4-BIPHENYLYL) - 1-BUTANOLE

PROCEDURE FOR THE PRODUCTION OF NEW NAPHTHALINDERIVATEN

PROCEDURE FOR the PRODUCTION of NEW (4-BIPHENYLYL) - ALCOHOLS

PROCEDURE FOR the PRODUCTION of NEW (4-BIPHENYLYL) -3-BUTEN-1-OLE

CYCLOPENTANOL DERIVATIVES, THEIR PRODUCTION, THEIR USE AS SMELLING MATERIALS, MIXTURES, IN THOSE THESE PRODUCTS INCORPORATES, AND RECEIVED INTERMEDIATE PRODUCTS.

PROCEDURE FOR the PRODUCTION of NEW (4-BIPHENYLYL) - 1-BUTANOLE

PROCEDURE FOR the PRODUCTION of NEW (4-BIPHENYLYL) - 1-BUTANOLE

PROCEDURE FOR the PRODUCTION of NEW (4-BIPHENYLYL) - 1-BUTANOLE

PROCEDURE FOR the PRODUCTION of NEW (4-BIPHENYLYL) -3-BUTEN-1-OLE

PROCEDURE FOR the PRODUCTION of NEW (4-BIPHENYLYL) -1-BUTANOLE

PROCEDURE FOR THE PRODUCTION OF NEW ALKALI SALTS OF DAILKYLPROPIONSAUREN

Process for producing fluorinated methyl-benzyl alcohol

Process for the preparation of ethylene glycol from sugars

A process for the preparation of ethylene glycol and other C ...

HYDROGENOLYSIS PROCESS FOR THE PRODUCTION OF MONOETHYLENE GLYCOL MONOMETHYL ETHER, MONOETHYLENE GLYCOL AND ETHANOL

SYNTHESIS OF LIQUID FUELS FROM BIOMASS

Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to paraffins useful as liquid fuels The process involves the conv ersion of water soluble oxygenated hydrocarbons to oxygenates, such as alcohols, furans, ketones, aldehydes, carboxylic acids, diols. triols. and/or other polyols, followed by the subsequent conversion of the oxygenates to paraffins by dehydration and alkylalion. The oxygenated hydrocarbons may originate from any source, but are preferably derived from biomass.

CATALYTIC HYDROGENOLYSIS OF ALDITOLS TO PRODUCE POLYOLS

Alditols such as 15-40 W % sorbitol solution in water are catalytically hydrocracked in a fixed bed catalytic reaction process using an active nickel catalyst to produce at least about 30 W % conversion to glycerol and glycol products. The feedstream pH is controlled to between 7 and 14 by adding a basic promoter material such as calcium hydroxide to prevent damage to the catalyst. Useful reaction zone conditions are 400-500.degree.F temperature, 1200-2000 psig hydrogen partial pressure, and liquid hourly space velocity of 1.5 to 3.0. To maintain desired catalyst activity and product yields, the catalyst is regenerated to provide catalyst age within the range of 20-200 hours. The reaction products are separated in distillation steps at successively lower pressures and unconverted alditol feed is recycled to the reaction zone for further hydrogenolysis to produce 80-95 W % glycerol product. Sorbitol conversion is maintained preferably at between about 30-70 W % by catalyst regeneration following ...

"4-(4-BIPHENYL)-1-BUTANOL"

DEHYDRATION CATALYSTS, PARTICULARLY FOR THE DEHYDRATION OF DIOLS

CATALYTIC DEHYDRATION OF VICINAL DIOLS AND OLEFINIC ALCOHOLS USING CALCIUM PYROPHOSPHATE AINING DEHYDRATION CATALYSTS

A dehydration catalyst (particularly useful for vicinal diols such as methyl-2,3-butane-diol,an isopreneprecursor) formed of calcium pyrophosphate, and possibly at least one pyrophosphate, whether mixed or not, of at least one metal from the group consisting of lithium, sodium, strontium, and barium, and/or at least one neutral orthophosphate, whether mixed or not, of at least one metal selected from the group consisting of lithium, sodium, strontium, barium, and calcium Also processes for making and utilizing such catalysts; for example, a process including the steps of: (a) Mixing calcium pyrophosphate and/or dicalcium orthophosphate and at least one pyrophosphato, whether mixed or not, of at least one metal from the group consisting of lithium, sodium, strontium and barium; and/or at least one acid orthophosphate, whether mixed or not, of at least one metal from the group consisting of lithium, sodium, strontium and barium, in the form of dry and/or moist powders to which water may be ...

VAPOUR-PHASE HYDROGENATION OF GLYCEROL

... ²A process for hydrogenation of glycerol in which a feed comprising glycerol is ²contacted with a ²stream of a hydrogen-containing gas and subjected to hydrogenation in the ²vapour phase in the ²presence of a catalyst at a temperature of from about 160.degree.C to about ²260.degree.C, a pressure of from ²about 10 to about 30 bar, a hydrogen to glycerol ratio of from 400:1 to about ²600:1 and a ²residence time of from about 0.01 to about 2.5 secs.² ...

METHODS AND SYSTEMS FOR GENERATING POLYOLS

Disclosed are methods for generating propylene glycol, ethylene glycol an d other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols fr om biomass using hydrogen produced from the biomass. The methods involve rea cting a portion of an aqueous stream of a biomass feedstock solution over a catalyst under aqueous phase reforming conditions to produce hydrogen, and t hen reacting the hydrogen and the aqueous feedstock solution over a catalyst to produce propylene glycol, ethylene glycal and the other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols. The disclosed methods can be run at lower temperatures and pressures, and allows for the production o f oxygenated hydrocarbons without the need for hydrogen from an external sou rce.

PROCESS FOR PREPARING .ALPHA., .OMEGA.-ALKENOLS

The invention relates to a process for preparing .alpha.,.omega.-alkenols by catalytic monodehydration of .alpha.,.omega.-alkanediols over a catalyst system comprising the combination of aluminum phosphate and barium phosphate. The gas-phase dehydration which occurs over this catalyst at temperatures of from 300 to 500.degree.C advantageously combines selectivity with a high space-time yield while simultaneously enabling a high throughput over the catalyst.

Procédé de préparation d'alcools

4-(4-biphenylyl)-1-butanol - with antiphlogistic props

Title cpd. is of formula (I): and is prepd. e.g. by reducing cpds. of formula (II): (where B is OH or any alkoxy, aralkoxy, aryloxy or acyloxy gp., or halogen atom), with a complex hydride, e.g. LiAlH4 in a solvent, or with catalytically activated H2.

Verfahren zur Herstellung von 6-Alkyl-citronellolen

VERFAHREN ZUR HERSTELLUNG VON NEUEN RIECHSTOFFEN.

Odorising agents for perfumes and soaps - based on isomeric substituted octenol mixtures

Odorisers/perfumes based on a mixt. of isomeric alcohols of general formula where R1 is C1-3 alkyl or alkylidene, R2 is C1-4 alkyl or alkylidene and the dotted lines represent 1 C=C double bond emanating from the 6 posn. either to R1,R2 or the 5 posn. These odorising cpds. can be used in perfumes, soaps etc. to give flower odours e.g. "lily of the valley" etc. of good lasting power.

RIECHSTOFFKOMPOSITIONEN.

Riechstoffkompositionen

Riechstoffkomposition

Riechstoffkompositionen

Perfume compositions

The perfume compositions contain a compound of the formula I in which one R radical is hydrogen and the other is methyl, and R<1> is the 1- or 2-isobutenyl radical. The compounds have a leathery odour reminiscent of ivy or lavender-like. ...

Process for the preparation of acetic acid derivatives

Process for the preparation of new acetic acid derivatives of general formula: in which M represents a nontoxic alkali metal atom and n represents 2 or 3, according to which process an alcohol of general formula: in which n has the same meaning as above, is oxidised, for example using chromic anhydride and in a suitable solvent, to obtain an acetic acid derivative in the form of the free acid which is treated with an alkali metal hydroxide to obtain the desired salt. The new compounds of formula I are useful as competitive inhibitors of gamma -aminobutyric/ alpha -ketoglutaric transaminase, antianoxics and anticonvulsants.

Process for the preparation of acetic acid derivatives

The invention relates to a process for the preparation of new acetic acid derivatives of general formula: in which R1 and R2, which are identical, each represent n-propyl or n-butyl and Me represents a nontoxic alkali metal atom, according to which process a mixture of ethylenic acids obtained by dehydration of a beta -hydroxylated acid of formula: in which R1 and R2 have the same meaning as above, is hydrogenated, under pressure, in a suitable solvent and in the presence of a catalyst, which provides an acetic acid derivative in the form of a free acid which is treated with an alkali metal hydroxide to obtain the desired salt. The new compounds of formula I are useful as competitive inhibitors of gamma -aminobutyric/ alpha -ketoglutaric transaminase, antianoxics and anticonvulsants.

METHOD OF PRODUCING DIENES

СПОСОБ ПОЛУЧЕНИЯ ДИЕНОВ

Изобретение относится к способу получения диена, предпочтительно сопряженного диена, более предпочтительно 1,3-бутадиена, включающему дегидратацию по меньшей мере одного алкенола, имеющего число атомов углерода больше или равное 4, в присутствии каталитического материала, содержащего по меньшей мере один кристаллический металлосиликат в кислотной форме, предпочтительно макропористый цеолит, более предпочтительно цеолит со структурой FAU, BEA или MTW. Предпочтительно указанный алкенол, имеющий число атомов углерода больше или равное 4, можно получить непосредственно с помощью способов биосинтеза или способов каталитической дегидратации по меньшей мере одного диола. Когда указанный алкенол представляет собой бутенол, указанный диол предпочтительно представляет собой бутандиол, более предпочтительно 1,3-бутандиол, еще более предпочтительно био-1,3-бутандиол, т.е. 1,3-бутандиол, полученный с помощью способов биосинтеза. Когда указанным алкенолом является 1,3-бутандиол или био-1,3-бутандиол, ...

СПОСОБ ПОЛУЧЕНИЯ 1,2-ПРОПАНДИОЛА

Настоящее изобретение относится к способу удаления гидроксипропана из потока сырого продукта гидрогенизации глицерола, содержащего 1,2-пропандиол и гидроксипропанон в качестве примесей, причем заявленный способ включает: (а) при необходимости конденсацию потока сырого продукта и (б) обеспечение взаимодействия фазы сырого продукта в жидкой среде с потоком газа, содержащего водород, в присутствии гетерогенного катализатора при подходящем температурном режиме и давлении таким образом, что гидроксипропанон, присутствующий в потоке сырого продукта, превращается в нужный пропандиол.

СПОСОБ ПОЛУЧЕНИЯ 1,2-ПРОПАНДИОЛА

Настоящее изобретение относится к способу удаления гидроксипропана из потока сырого продукта гидрогенизации глицерола, содержащего 1,2-пропандиол и гидроксипропанон в качестве примесей, причем заявленный способ включает: (а) при необходимости конденсацию потока сырого продукта и (б) обеспечение взаимодействия фазы сырого продукта в жидкой среде с потоком газа, содержащего водород, в присутствии гетерогенного катализатора при подходящем температурном режиме и давлении таким образом, что гидроксипропанон, присутствующий в потоке сырого продукта, превращается в нужный пропандиол.

СПОСОБЫ ПОЛУЧЕНИЯ ОКСИГЕНИРОВАННОГО СОЕДИНЕНИЯ И ПРОПИЛЕНГЛИКОЛЯ, РЕАКТОРНАЯ СИСТЕМА ДЛЯ ПОЛУЧЕНИЯ ОКСИГЕНИРОВАННЫХ СОЕДИНЕНИЙ (ВАРИАНТЫ)

Способы получения пропиленгликоля, этиленгликоля и других полиолов, диолов, кетонов, альдегидов, карбоновых кислоты и спиртов из биомассы с использованием водорода, полученного из этой же биомассы. Способы включают реакцию части водного потока сырьевой биомассы над катализатором в условиях жидкостнофазового риформинга для образования водорода, и потом реакцию этого водорода с водной сырьевой биомассой над катализатором для получения пропиленгликоля, этиленгликоля и других полиолов, диолов, кетонов, альдегидов, карбоновых кислот и спиртов. Эти способы могут быть реализованы при низких температурах и давлениях и обеспечивают получение оксигенированных углеводородов без водорода из внешнего источника.

Supported meso-porous molecular sieve catalyst, and preparation method and application thereof

Conversion method for biomass polyols with high boiling point

Supported bi-metal component catalyst, preparation method thereof, and method of hydrogenolysis reaction of glycerol

Process for the preparation of glycols

Method for preparing high-purity allyl alcohol

DECOMPOSITION DE POLYCARBONATES POUR LA FORMATION D'ALCOOLS A INSATURATION TERMINALE

L'INVENTION CONCERNE UN PROCEDE DE PREPARATION D'ALCOOLS A INSATURATION TERMINALE, CARACTERISE PAR LE FAIT QUE L'ON DECOMPOSE THERMIQUEMENT UN POLYCARBONATE EN PRESENCE D'UN CATALYSEUR CONTENANT DU TITANE.

DIHYDROXY-7,8 PARAMENTHENE-1 AND ITS ESTERS AND METHOD OF PREPARATION

METHOD FOR DEHYDRATING MIXTURE CONTAINING ETHANOL AND ISOPROPANOL

L'invention se rapporte à un procédé de production d'un mélange d'éthylène et de propylène à partir d'un mélange contenant de l'éthanol, de l'isopropanol et ayant une teneur en eau comprise entre 30 et 75% poids par rapport au poids total du mélange, dans lequel: a) on met en contact dans une unité de déshydratation le mélange avec un catalyseur de déshydratation choisi parmi: • une alumine (A) ayant une surface spécifique BET mesurée selon la norme ASTM D 3663-03 comprise entre 200 et 350 m2/g, un diamètre moyen mésoporeux compris entre 5 et 15 nm, une teneur en sodium inférieure à 50 ppm poids et une teneur en soufre inférieure à 40 ppm poids; et • une alumine (B) ayant une surface spécifique BET mesurée selon la norme ASTM D 3663-03 comprise entre 130 et 180 m2/g, un diamètre moyen mésoporeux compris entre 14 et 20 nm, une teneur en sodium comprise entre 300 et 600 ppm poids et une teneur en soufre comprise entre 800 et 1300 ppm poids; la mise en contact étant effectuée à une température ...

Method of preparation of citronellol

NOVEL ODORANT

LITER-MENTHYL-OXY ALDEHYDE AND PREPARATION OF THE SAME

PURPOSE: A liter-menthyl-oxyaldehyde compound is found out to give out menthol fragrance under both of normal condition and pyrolysis reaction and is preferably used in a wide application such as foodstuff, tobacco, medicine and/or perfume. CONSTITUTION: A method for preparing a liter-menthyl-oxyaldehyde compound having a formula (I) is performed by reacting l-menthol and trimethyl ortho-formate under the presence of organic solvent and catalyst. The prepared compound can emit menthol fragrance at normal and/or pyrolysis circumstances. The organic solvent is selected from a group comprised of dichloromethane, benzene, toluene, chloroform and tetrahydrofuran. The catalyst is selected from a group comprised of ZnCl2, AlCl3, TiCl4, silica gel, para-toluene sulfonate, campa-sulphonate. COPYRIGHT 2001 KIPO ...

NEW (4 A-BIPHENYLYL DERIVATIVES) - ALCOHOLS AND PRODUCTION METHODS

CONVERSAO TERMOQUIMICA DE BIOMASSA PARA ETANOL

HYDROGENATION CATALYST COMPRISING NICKEL ON CARBON

The hydrogenation catalyst comprises from 1 to 50% by weight, based on the total catalyst, of nickel on a carbon support, wherein the hydrogenation catalyst does not comprise any rhenium. Coconut shell carbon is preferably used as support.

PROCESS FOR PRODUCING A STREAM COMPRISING ETHYLENE GLYCOL

It is disclosed a process for producing a low boiling mixture comprising ethylene glycol and propylene glycol from a liquid sugar stream derived from a ligno-cellulosic biomass feedstock. The liquid sugar stream is catalytically converted in the presence of hydrogen to a mixture, which is separated into at least a high boiling mixture, comprising glycerol, and the low boiling mixture. The high boiling mixture is converted to hydrogen by reforming and the reforming hydrogen is used in the catalytical steps. Preferably, all the hydrogen used in the conversion process is generated by aqueous phase reforming of the high boiling polyols mixture.

NEW METHOD FOR THE CONVERSION OF SUGARS AND SUGAR ALCOHOLS INTO MONO- AND POLYOXYGENATED COMPOUNDS IN THE PRESENCE OF A HETEROGENEOUS CATALYST

The invention concerns a method for converting a feedstock selected from sugars or sugar alcohols, alone or in a mixture, into mono- or polyoxygenated compounds, wherein the feedstock is contacted with at least one heterogeneous catalyst comprising a support selected from perovskites of formula ABO3, in which A is selected from the elements Mg, Ca, Sr and Ba and B is selected from the elements Fe, Mn, Ti and Zr, and the oxides of elements selected from lanthanum, neodymium, yttrium and cerium, alone or in a mixture, which oxides can be doped with at least one element selected from alkali metals, alkaline earths and rare earths, in a reducing atmosphere, at a temperature of 100° C to 300° C and at a pressure of 0.1 MPa to 50 MPa.

PREPARATION OF DERIVATIVE OF POLYHYDRIC ALCOHOLS

A method for converting a polyhydric alcohol into propylene glycol and butanediols is disclosed. Also disclosed are methods for converting polyhydric alcohols into three-carbon products and four-carbon products. Also disclosed are methods for maximizing conversion of polyhydric alcohols and minimizing formation of reaction products that are difficult to remove from the desired product. In other embodiments, methods are described to optimize use of reactants, including hydrogen, in hydrogenolysis of polyhydric alcohols.

IMPROVED CATALYSTS FOR HYDRODEOXYGENATION OF POLYOLS

Disclosed are methods for producing polyols, ketones, carboxylic acids, aldehydes and alcohols from biomass-derived oxygenated hydrocarbons, such as sugars, sugar alcohols, saccharides and the like, using catalysts containing platinum, ruthenium and tin. The methods can be run at lower temperatures and pressures, and allows for the production of oxygenated compounds without the need for hydrogen from an external source. The oxygenated compounds produced are useful as industrial chemicals or chemical intermediates for liquid fuels production.

A HYDROGENTATION CATALYST, AND A METHOD FOR ITS PREPARATION AND USE, IN PARTICULAR FOR HYDROGENATION AND/OR HYDROGENOLYSIS OF CARBOHYDRATES AND POLYHYDRIC ALCOHOLS

A metallic catalyst composition on an inert support, suitable in particular for hydrogenolysis reactions of higher polyhydric alcohols, characterized in that it comprises the following relative to 100 parts of the catalyst: a) 0.5 to 5 weight % ruthenium; b) 1 to 10 weight % of a metal selected from the group consisting of palladium, platinum and rhodium; and c) 0.5 to 2.5 weight % copper, in which the copper content is lower than the content of the metal b). The catalyst is used in particular for producing lower polyhydric alcohols such as ethanediol, propylene glycol, butanediol and glycerol, by means of hydrogenolysis reaction of higher polyhydric alcohols.

Preparation of alkylamines and method of increasing the hydroamination activity of calcined zeolitic catalysts

In a process for preparing alkylamines by reacting olefins with ammonia, primary or secondary amines under hydroaminating conditions over a calcined zeolitic catalyst, the calcined zeolitic catalyst is thermally activated at from 100 to 550° C. in a gaseous stream of air, nitrogen, other inert gases or mixtures thereof not more than 24 hours before commencement of the reaction.

4-(4)-BIPHENYLYL)-1-BUTANOL

Process for producing hydrogenolysis products of polyhydric alcohols

The present invention relates to a process for producing hydrogenolysis products of polyhydric alcohols with a good selectivity and a high yield, as well as hydrogenolysis catalysts used in the production process. The present invention provides (1) a process for producing a hydrogenolysis product of a polyhydric alcohol which includes the step of reacting the polyhydric alcohol with hydrogen in the presence of a catalyst containing a copper component, wherein the catalyst is a catalyst (A) containing the copper component, an iron component and an aluminum component, or a catalyst (B) containing the copper component and a silicon component; and (2) a hydrogenolysis catalyst for polyhydric alcohols which includes a copper component, an iron component and an aluminum component, and (3) a hydrogenolysis catalyst for polyhydric alcohols which includes a copper component and a silicon component.

Process for the production of hexanediols

Disclosed are processes for preparing 1,2-cyclohexanediol, and mixtures of 1,2-cyclohexanediol and 1,6-hexanediol, by hydrogenating 1,2,6-hexanetriol.

Methods and systems for generating polyols

Disclosed are methods for generating propylene glycol, ethylene glycol and other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols from biomass using hydrogen produced from the biomass. The methods involve reacting a portion of an aqueous stream of a biomass feedstock solution over a catalyst under aqueous phase reforming conditions to produce hydrogen, and then reacting the hydrogen and the aqueous feedstock solution over a catalyst to produce propylene glycol, ethylene glycol and the other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols. The disclosed methods can be run at lower temperatures and pressures, and allows for the production of oxygenated hydrocarbons without the need for hydrogen from an external source.

PRODUCTION OF ALPHA, OMEGA-DIOLS

Disclosed herein are processes for preparing an α,ω-C-diol, wherein n is 5 or greater, from a feedstock comprising a Coxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising Cu, a Cu oxide, or mixtures thereof; a heteropoly acid component comprising H[P(WO)], H[Si(WO)], H[P(MoO)], H[Si(MoO)], CsH[P(WO)], CsH[Si(WO)], or mixtures thereof; optionally a second metal component comprising Cr, a Cr oxide, Ni, a Ni oxide, Mn, a Mn oxide, Fe, an Fe oxide, Co, a Co oxide, Mo, a Mo oxide, W, a W oxide, Re, a Re oxide, Zn, or a Zn oxide, Ag, a Ag oxide, SiO, or AlO; optionally at least one promoter comprising Na, K, Mg, Rb, Cs, Ca, Sr, Ba, Ce, or mixtures thereof; and optionally a support. 1. A process for preparing an α ,ω-C-diol , comprising the steps:{'sub': 'n', '(a) providing a feedstock comprising a Coxygenate;'}{'sub': 'n', '(b) contacting the feedstock with hydrogen gas, in the presence of a catalyst and at a temperature and for a time sufficient to form a product mixture comprising an α,ω-C-diol;'}wherein n is 5 or greater; and wherein the catalyst comprises a first metal component, a heteropoly acid component, optionally a second metal component, optionally at least one promoter, and optionally a support;wherein:the first metal component comprises Cu, a Cu oxide, or mixtures thereof;{'sub': 3', '3', '10', '4', '4', '3', '10', '4', '4', '3', '10', '4', '4', '3', '10', '4', '2.5', '0.5', '3', '10', '4', '2.5', '0.5', '3', '10', '4, 'the heteropoly acid component comprises H[P(WO)], H[Si(WO)], H[P(MoO)], H[Si(MoO)], CsH[P(WO)], CsH[Si(WO)], or mixtures thereof;'}{'sub': 2', '2', '3, 'the second metal component comprises Cr, a Cr oxide, Ni, a Ni oxide, Mn, a Mn oxide, Fe, an Fe oxide, Co, a Co oxide, Mo, a Mo oxide, W, a W oxide, Re, a Re oxide, Zn, or a Zn oxide, Ag, a Ag oxide, SiO, or AlO; and'}the promoter comprises Na, K, Mg, Rb, Cs, Ca, Sr, Ba, Ce, or mixtures thereof.2. The process of ...

PRODUCTION OF ALPHA, OMEGA-DIOLS

Disclosed herein are processes for preparing an α,ω-C-diol, wherein n is 5 or greater, from a feedstock comprising a Coxygenate. In some embodiments, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising metals M1, M2, and M3 and optionally a support, wherein: M1 is Mn, Cr, V, or Ti; M2 is Ni, Co, or Fe; and M3 is Cu, Ag, Pt, Pd or Au; or M1 is Pt or Rh; M2 is Cu, Ni or Pd; and M3 is Mo, Re or W. The Coxygenate may be obtained from a biorenewable resource. 2. The process of claim 1 , wherein n=5 or 6.3. The process of claim 1 , wherein the optional support is present in the catalyst and comprises WO claim 1 , SiO claim 1 , AlO claim 1 , carbon claim 1 , TiO claim 1 , ZrO claim 1 , SiO—AlO claim 1 , montmorillonite claim 1 , SiO—TiO claim 1 , tungstated ZrO claim 1 , zeolites claim 1 , VO claim 1 , MoO claim 1 , or mixtures thereof.4. The process of claim 1 , wherein the Coxygenate comprises 1 claim 1 ,2 claim 1 ,6-hexanetriol; 1 claim 1 ,2 claim 1 ,5-pentanetriol; 2H-tetrahydropyran-2-methanol; tetrahydrofuran-2 claim 1 ,5-dimethanol; furan-2 claim 1 ,5-dimethanol; 2 claim 1 ,5 dihydrofuran-2 claim 1 ,5-dimethanol; levoglucosenone; levoglucosan; levoglucosenol; 1 claim 1 ,6-anhydro-3 claim 1 ,4-dideoxy-p-D-pyranose-2-one; isosorbide; hydroxymethylfurfural; sorbitol; glucose; fructose; xylitol; 3 claim 1 ,4-dihydro-2H-pyran-2-carbaldehyde; 1 claim 1 ,2 claim 1 ,5 claim 1 ,6-hexanetetraol; 1 claim 1 ,2 claim 1 ,3 claim 1 ,5 claim 1 ,6-hexanepentanol; 1 claim 1 ,5-anhydro-3 claim 1 ,4-dideoxy-hexitol; 5-hydroxy-2H-tetrahydropyran-2 methanol; furfural; furfuryl alcohol; tetrahydrofurfuryl alcohol; pentoses; dimers containing pentose; oligomers containing pentose; hexoses; dimers containing hexose; oligomers containing hexose; condensation products from the reaction of 5-(hydroxymethyl)-2-furfural with ketones and/or aldehydes; and condensation products from the reaction of furfural with ketones and/or aldehydes.5. The ...

PRODUCTION OF ALPHA, OMEGA-DIOLS

Disclosed herein are processes for preparing an α,ω-C-diol, wherein n is 5 or greater, from a feedstock comprising a Coxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising Pt, Cu, Ni, Pd, Pt, Rh, Ir, Ru, or Fe on a WOor WOsupport. In one embodiment, the process comprises contacting the feedstock with hydrogen in the presence of a catalyst comprising a metal M1 and a metal M2 or an oxide of M2, and optionally a support. In one embodiment, M1 is Pd, Pt, or Ir; and M2 is Mo, W, V, Mn, Re, Zr, Ni, Cu, Zn, Cr, Ge, Sn, Ti, Au, or Co. The Coxygenate may be obtained from a biorenewable resource. 2. The process of claim 1 , wherein n=5 or 6.3. The process of wherein the optional support is present in the catalyst and comprises WO claim 1 , SiO claim 1 , AlO claim 1 , carbon claim 1 , TiO claim 1 , ZrO claim 1 , SiO—AlO claim 1 , montmorillonite claim 1 , SiO—TiO claim 1 , tungstated ZrO claim 1 , zeolites claim 1 , VO claim 1 , MoO claim 1 , or mixtures thereof.4. The process of wherein the Coxygenate comprises 1 claim 1 ,2 claim 1 ,6-hexanetriol; 1 claim 1 ,2 claim 1 ,5-pentanetriol; 2H-tetrahydropyran-2-methanol; tetrahydrofuran-2 claim 1 ,5-dimethanol; furan-2 claim 1 ,5-dimethanol; 2 claim 1 ,5 dihydrofuran-2 claim 1 ,5-dimethanol; levoglucosenone; levoglucosan; levoglucosenol; 1 claim 1 ,6-anhydro-3 claim 1 ,4-dideoxy-p-D-pyranose-2-one; isosorbide; hydroxymethylfurfural; sorbitol; glucose; fructose; xylitol; 3 claim 1 ,4-dihydro-2H-pyran-2-carbaldehyde; 1 claim 1 ,2 claim 1 ,5 claim 1 ,6-hexanetetraol; 1 claim 1 ,2 claim 1 ,3 claim 1 ,5 claim 1 ,6-hexanepentanol; 1 claim 1 ,5-anhydro-3 claim 1 ,4-dideoxy-hexitol; 5-hydroxy-2H-tetrahydropyran-2 methanol; furfural; furfuryl alcohol; tetrahydrofurfuryl alcohol; pentoses; dimers containing pentose; oligomers containing pentose; hexoses; dimers containing hexose; oligomers containing hexose; condensation products from the reaction of 5-( ...

PRODUCTION OF ALPHA, OMEGA-DIOLS

Disclosed herein are processes for preparing an α,ω-C-diol, wherein n is 5 or greater, from a feedstock comprising a Coxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising a first metal component comprising Ni, Ir, Pt, Rh, Ru, Pd, Fe, Ag, or Au; a heteropoly acid component comprising H[P(WO)], H[Si(WO)], H[P(MoO)], H[Si(MoO)], CsH[P(WO)]CsH[Si(WO)], or mixtures thereof; optionally a second metal component comprising Cr, a Cr oxide, Ni, a Ni oxide, Fe, a Fe oxide, Co, a Co oxide, Mn, a Mn oxide, Mo, a Mo oxide, W, a W oxide, Re, a Re oxide, Zn, a Zn oxide, SiO, or AlO; optionally at least one promoter comprising Na, K, Mg, Rb, Cs, Ca, Sr, Ba, Ce, or mixtures thereof; and optionally a support. In one embodiment, the optional support is present in the catalyst and comprises WO, SiO, AlO, carbon, TiO, ZrO, SiO—AlO, montmorillonite, SiO—TiO, tungstated ZrO, zeolites, VO, MoO, or mixtures thereof. The Coxygenate may be obtained from a biorenewable resource. 1. A process for preparing an α ,ω-C-diol , comprising the steps:{'sub': 'n', '(a) providing a feedstock comprising a Coxygenate;'}{'sub': 'n', '(b) contacting the feedstock with hydrogen gas, in the presence of a catalyst and at a temperature and for a time sufficient to form a product mixture comprising an α,ω-C-diol;'}wherein n is 5 or greater; and wherein the catalyst comprises a first metal component, a heteropoly acid component, optionally a second metal component, optionally at least one promoter, and optionally a support; wherein:the first metal component comprises Ni, Ir, Pt, Rh, Ru, Pd, Fe, Ag, or Au;{'sub': 3', '3', '10', '4', '4', '3', '10', '4', '4', '3', '10', '4', '4', '3', '10', '4', '2.5', '0.5', '3', '10', '4', '2.5', '0.5', '3', '10', '4, 'the heteropoly acid component comprises H[P(WO)], H[Si(WO)], H[P(MoO)], H[Si(MoO)], CsH[P(WO)], CsH[Si(WO)], or mixtures thereof;'}{'sub': 2', '2', '3, 'the second metal component ...

Reduction of c-0 bonds by catalytic transfer hydrogenolysis

The present invention relates to a method of reducing a C—O bond to the corresponding C—H bond in a substrate which could be a benzylic alcohol, allylic alcohol, ester, or ether or an ether bond beta to a hydroxyl group or alpha to a carbonyl group.

Methods for producing bioderived propylene glycol

In the process of distilling a polyol product mixture including one or both of a biobased propylene glycol and a biobased ethylene glycol from the reaction of hydrogen with a biobased feed, it has been discovered that undesirable epoxides can form, and the present invention provides means for guarding against their formation, for removing epoxides which do form by particular methods of distilling, and for removing the epoxides from a finished, otherwise commercially acceptable biobased glycol product.

PROCESS FOR HYDROGENOLYSIS OF GLYCEROL

A process for the hydrogenolysis of glycerol to produce propylene glycol as the major product comprising contacting the glycerol with hydrogen in the presence of a heterogeneous catalyst under conditions for the formation of propylene glycol is disclosed. In particular, propylene glycol is formed with a selectivity of greater than about 90%. 1. A process for the hydrogenolysis of glycerol to produce propylene glycol comprising:(a) contacting the glycerol with hydrogen in the presence of a heterogeneous catalyst under conditions for the formation of propylene glycol; and(b) optionally isolating the propylene glycol,wherein the heterogeneous catalyst comprises, consists essentially of or consists of Cu, Cr, Zn and Zr.2. The process of claim 1 , wherein the propylene glycol is formed as the major product in the process3. The process of claim 2 , wherein the propylene glycol is formed with a selectivity of greater than 90% claim 2 , 95% claim 2 , 96% claim 2 , 97% claim 2 , or 98%.4. The process of claim 1 , wherein the catalyst is prepared using a co-precipitation method.5. The process of claim 1 , wherein the heterogeneous catalyst comprises claim 1 , consists essentially of or consists of Cu claim 1 , Zn claim 1 , Cr and Zr in an elemental molar ratio (Cu:Zn:Cr:Zr) of 3:2:1:1 claim 1 , 3:2:1:2 claim 1 , 3:2:1:3 or 3:2:1:4.67.-. (canceled)8. The process of claim 1 , wherein the glycerol is a solution comprising at least about 50% (w/w) glycerol.9. The process of claim 8 , wherein the glycerol is an aqueous solution comprising about 60% (w/w) to about 90% (w/w) claim 8 , about 70% (w/w) to about 85% (w/w) claim 8 , about 80% (w/w) glycerol or about 70% (w/w) glycerol.10. The process of claim 1 , wherein the glycerol is crude glycerol obtained as a byproduct from the production of biodiesel.11. The process of claim 1 , wherein the conditions for the formation of propylene glycol comprise use of a catalyst loading of about 1% (w/w) to about 5% (w/w) claim 1 , about 3% (w ...

BIOMASS CONVERSION PROCESS TO HYDROCARBONS

A process for the production of a higher hydrocarbon from solid biomass is provided. The process provides for ready separation of organic phase from aqueous phase which organic phase maybe recycled as a digestive solvent in a digestion and/or deoxygenation of solid biomass. By contacting the oxygenated hydrocarbon intermediate containing diols produced from the digestion and deoxygenation of solid biomass with an amorphous silica alumina catalyst reduces the diols content and product stream readily separates into organic phase and aqueous phase. 1. A process for the production of a higher hydrocarbon from solid biomass , said process comprising:a. a biomass solid containing cellulose, hemicellulose, and lignin;b. digesting and hydrodeoxygenating the biomass solid in a liquid digestive solvent, said digestive solvent containing a solvent mixture having a boiling point of greater than 40° C. in the presence of a hydrothermal hydrocatalytic in the presence of hydrogen at a temperature in the range of 110° C. to less than 300° C. at a pressure in a range of from 20 bar to 200 bar to form a stable oxygenated hydrocarbon intermediate product having a viscosity of less than 100 centipoise (at 50° C.), a diol content of at least 2 wt. %, less than 2 wt % of sugar, and less than 2 wt % acid (acetic acid equivalent) based on the intermediate product, and at least 60% of carbon exists at less than or equal to 9;c. reacting at least a portion of the stable oxygenated hydrocarbon intermediate product with an acidic amorphous silica alumina catalyst at a temperature in the range from 300° C. to 400° C. thereby producing monooxygenated stream containing water and monooxygenates having a boiling point of at least 40° C.;d. condensing at least a portion of the monooxygenated stream to liquid phase producing an aqueous phase and an organic phase;e. removing the aqueous phase from the organic phase;f. recycling at least a first portion of the organic phase to step (b) as a portion of ...

BIOMASS CONVERSION PROCESS TO HYDROCARBONS

An improved process for the production of a higher hydrocarbon from solid biomass is provided. Solid biomass that has been digested and hydrodeoxygenated in a liquid digestive solvent in the presence of a hydrothermal hydrocatalytic catalyst is separated to an organic rich phase and an aqueous rich phase containing diols. At least a portion of the aqueous rich phase is contacted with an acidic amorphous silica alumina catalyst producing monooxygenate-containing stream comprising water, organic monooxygenates, and unsaturated aliphatic hydrocarbons. At least a portion of the monooxygenate-containing stream is contacted with a solid acid condensation catalyst to produce a higher hydrocarbons stream. At least a portion of the organic rich phase is also contacted with a solid acid condensation catalyst to produce a higher hydrocarbons stream. 1. A process for the production of a higher hydrocarbon from solid biomass , said process comprising:a. providing a biomass solid containing cellulose, hemicellulose, and lignin;b. digesting and hydrodeoxygenating the biomass solid in a liquid digestive solvent in the presence of a hydrothermal hydrocatalytic catalyst and hydrogen at a temperature in the range of 110° C. to less than 300° C. and at a pressure in a range of from 20 bar to 200 bar, said digestive solvent containing a solvent mixture having a boiling point of at least 40° C., to form a stable oxygenated hydrocarbon intermediate product having a viscosity of less than 100 centipoise (at 50° C.), a diol content of at least 2 wt. %, less than 2 wt. % of sugar, and less than 2 wt. % acid (based on acetic acid equivalent), based on the intermediate product, and at least 60% of carbon exists in molecules having 9 carbon atoms or less;c. separating the stable oxygenated hydrocarbon intermediate product to an organic rich phase and an aqueous rich phase;d. reacting at least a portion of the aqueous rich phase with an acidic amorphous silica alumina catalyst at a temperature ...

PROCESS FOR THE DEHYDRATION OF OXYGENATED COMPOUNDS

The present invention relates to a process for the dehydration of at least one oxygenated compound, preferably selected from saturated alcohols, unsaturated alcohols, diols, ethers, in the presence of at least one dehydration catalyst selected from cerium oxide (CeO), aluminium oxide (γ-AlO), aluminium silicate, silica-aluminas (SiO-AlO), aluminas, zeolites, sulfonated resins, ion-exchange resins, metal oxides (for example, lanthanum oxide, zirconium oxide, tungsten oxide, thallium oxide, magnesium oxide, zinc oxide); of at least one basic agent selected from ammonia (NH), or from inorganic or organic compounds containing nitrogen capable of developing ammonia (NH) during said dehydration process; and, optionally, of silica (SiO), or of at least one catalyst for the dissociation of ammonia (NH) selected from catalysts comprising silica (SiO), preferably of silica (SiO). 1. A process comprising dehydrating at least one oxygenated compound in the presence of{'sub': 2', '2', '3', '2', '2', '3, '(i) at least one dehydration catalyst selected from the group consisting of cerium oxide (CeO), aluminum oxide (γ-AlO), aluminum silicate, silica-alumina (SiOAlO) alumina, a zeolite, a sulfonate resin, an ion exchange resin, and a metal oxide;'}{'sub': 3', '3, '(ii) at least one basic agent selected from the group consisting of ammonia (NH) and an inorganic or organic compound comprising nitrogen capable of developing ammonia (NH) during the dehydration; and'}{'sub': '2', '(iii) optionally silica (SiO).'}2. A process comprising dehydrating at least one oxygenated compound by feeding to a reactor a mixture comprising the oxygenated compound and at least one basic agent selected from the group consisting of ammonia (NH) and an inorganic or organic compound comprising nitrogen capable of developing ammonia (NH) during the dehydration , wherein the mixture is fed to the reactor so as to pass first through a first catalytic bed and subsequently through a second catalytic bed in the ...

PROCESS FOR THE PRODUCTION OF DIENES

Process for the production of a diene, preferably a conjugated diene, more preferably 1,3-butadiene, comprising the dehydration of at least one alkenol in the presence of at least one catalytic material comprising at least one acid catalyst based on silica (SiO) and alumina (AIO), preferably a silica-alumina (SiO-AIO), said catalyst having a content of alumina (AIO) lower than or equal to 12% by weight, preferably ranging from 0.1% by weight to 10% by weight, with respect to the total weight of the catalyst. Preferably, said alkenol can be obtained directly from biosynthesis processes, or through the catalytic dehydration of at least one diol, preferably a butanediol, more preferably 1,3-butanediol, even more preferably bio-1,3-butanediol, deriving from biosynthesis processes. Preferably, said 1,3-butadiene is bio-1,3-butadiene. 1. A process for manufacturing a diene , the process comprising dehydrating at least one alkenol in the presence of at least one catalytic material comprising at least one silica (SiO) and alumina (AlO) based acid catalyst , said catalyst having a content of alumina lower than or equal to 12% by weight , relative to a total weight of the catalyst.2. The process according to claim 1 , wherein the alkenol is selected from the group consisting of 3-buten-2-ol (methyl vinyl carbinol) claim 1 , 3-buten-1-ol (allyl carbinol) claim 1 , 2-buten-1-ol (crotyl alcohol) claim 1 , and mixtures thereof.3. The process Process according to claim 1 , wherein the alkenol is directly obtained from a biosynthetic process claim 1 , or by a catalytic dehydration processes of at least one diol claim 1 , deriving from a biosynthetic process.4. The process according to claim 1 , wherein the alkenol derives from catalytic dehydration of at least one diol deriving from the fermentation of sugars.5. The process according to claim 4 , wherein the diol is a bio-1 claim 4 ,3-butanediol deriving from fermentation of sugars obtained from guayule or thistle claim 4 , ...

METHOD FOR SYNTHESIZING AN ALKENOIC ACID

There is provided a method for synthesizing an alkenoic acid, in particular acrylic acid comprising the step of oxidizing an alkenyl alcohol in the presence of a metal oxide catalyst to form the alkenoic acid. The invention further provides a step of deoxydehydrating a polyol, including glycerol to obtain said alkenyl alcohol including an allyl alcohol. 1. A method for synthesizing an alkenoic acid comprising the step of oxidizing an alkenyl alcohol in the presence of a metal oxide catalyst to form said alkenoic acid , wherein said metal oxide catalyst has the formula MoVWO x is a number between 1 to 10;', 'y is a number between 0.05 to 10;', 'm is a number between 1 to 10; and', 'd is calculated based on the formula 3x+2y+3m., 'where'}2. The method of claim 1 , further comprising claim 1 , before said oxidizing step claim 1 , the step of deoxydehydrating a polyol to obtain said alkenyl alcohol.3. The method of claim 2 , wherein said polyol is a triol claim 2 , tetraol claim 2 , pentanol or hexanol.4. The method of claim 3 , wherein said polyol is selected from the group consisting of glycerol claim 3 , 2-methyl-1 claim 3 ,2 claim 3 ,3-propanetriol claim 3 , 1 claim 3 ,2 claim 3 ,3-butanetriol claim 3 , 2-methyl-1 claim 3 ,2 claim 3 ,3-butanetriol claim 3 , 2-methyl-1 claim 3 ,2 claim 3 ,3 claim 3 ,4-butanetetraol claim 3 , 1 claim 3 ,2 claim 3 ,3-pentanetriol claim 3 , 1 claim 3 ,2 claim 3 ,3-hexanetriol claim 3 , xylitol claim 3 , sorbitol claim 3 , arabinitol claim 3 , ribitol claim 3 , mannitol claim 3 , galactitol claim 3 , iditol claim 3 , erythritol claim 3 , threitol and mixtures thereof.5. The method of claim 1 , wherein said alkenyl alcohol is 2-alkenyl alcohol.6. The method of claim 5 , wherein said 2-alkenyl alcohol is selected from the group consisting of allyl alcohol claim 5 , 2-buten-1-ol claim 5 , 2-hexen-1-ol claim 5 , 2-penten-1 claim 5 ,4 claim 5 ,5-triol claim 5 , 2 claim 5 ,4-hexadien-1 claim 5 ,6-diol claim 5 , 2-hexene-1 claim 5 ,4 claim 5 ,5 ...

METHODS FOR CONVERTING GLYCEROL TO ALLYL COMPOUNDS

The present disclosure is directed towards methods of converting glycerol to an allyl compound, involving deoxydehydrating glycerol with formic acid and heat to form allyl alcohol; and esterifying the allyl alcohol with formic acid and/or phthalic anhydride and heat to form allyl formate and diallyl phthalate. In some instances, the heat is generated by a microwave. In further instances, the methods involve polymerizing the allyl alcohol, allyl formate and/or diallyl phthalate to form poly(allyl alcohol) or poly(allyl formate) or poly (diallyl phthalate). In some instances, the allyl polymers were used for the consolidation of oil sands tailings. 1. A method of converting glycerol to an allyl compound , comprising:a) deoxydehydrating glycerol with formic acid and heat to form allyl alcohol; andb) esterifying the allyl alcohol with formic acid and heat to form allyl formate.2. The method of claim 1 , wherein the heat is generated by a microwave.3. The method of claim 1 , wherein a microwave assists:a. deoxydehydrating glycerol with formic acid and heat by distillation to form allyl alcohol; andb. esterifying the allyl alcohol with formic acid and heat by reflux to form allyl formate.4. The method of claim 1 , wherein deoxydehydrating the glycerol with the formic acid and heat to form the allyl alcohol comprises heating the glycerol and the formic acid to about 195° C. claim 1 , and then heating the glycerol and the formic acid to about 240° C.5. The method of claim 4 , further comprising isolating the allyl alcohol while heating the glycerol and the formic acid to about 240° C.6. The method of claim 5 , further comprising cooling the glycerol and the formic acid to between about 95°-100° C. claim 5 , and then adding more of the formic acid.7. The method of claim 5 , wherein esterifying the allyl alcohol with formic acid and heat to form allyl formate comprises heating the allyl alcohol and formic acid at about 60° C.8. The method of claim 5 , wherein the allyl ...

One vessel process for making 1,2-propanediol from a high fructose feedstock

A process is described for directly converting a high fructose feedstock to a product mixture including one or more lower polyols in which 1,2-propanediol is produced in preference to any other lower polyols, wherein a high fructose feed and a source of hydrogen are supplied to a reaction vessel and reacted in the presence of a copper-containing, supported ruthenium catalyst to provide the product mixture.

Fuels And Fuel Additives Production From Glycerol Conversion Using A Monohydric Alcohol And Heterogeneous Catalysis

The present disclosure relates to a method of converting glycerol into organic reaction products. The method may include mixing glycerol with a monohydric alcohol. The mixture of glycerol and monohydric alcohol is then reacted in the presence of a heterogeneous nano-structured catalyst, wherein the monohydric alcohol is present at subcritical/supercritical temperatures and pressures. This converts the glycerol into one or more reaction products, wherein the reaction products include an oxygenated organic reaction product. Ninety percent or greater of the glycerol is converted. 1. A method of converting glycerol , comprising:mixing glycerol containing hydroxyl groups with methanol;reacting said glycerol and methanol in the presence of a heterogeneous nano-structured catalyst, wherein said methanol is present at a temperature of 200° C. or greater and a pressure of 1,140 psia or greater;converting said glycerol into one or more reaction products, wherein one or more of said hydroxyl groups of said glycerol is converted into alkyl, alkyl ether, carbonyl, cyclic ether or alkene functionality; andwherein 90% or greater of said glycerol is converted to said reaction products containing said converted hydroxyl functionality.2. The method of claim 1 , wherein said methanol is present at a temperature in the range of 200° C. to 400° C. and a pressure in the range of 2 claim 1 ,000 psia to 3 claim 1 ,500 psia.3. The method of claim 1 , wherein said methanol is present as a supercritical fluid.4. The method of claim 1 , wherein said heterogeneous nano-structured catalyst comprises a zeolite mineral.5. The method of claim 4 , wherein said heterogenous nano-structured catalyst includes a zeolite and an oxide claim 4 , wherein said zeolite is selected from the group consisting of zeolite X and zeolite Y claim 4 , and said oxide is selected from one or more of the following: alumina claim 4 , silica and aluminosilicate.6. The method of claim 1 , wherein said heterogeneous nano- ...

Shaped porous carbon products

Shaped porous carbon products and processes for preparing these products are provided. The shaped porous carbon products can be used, for example, as catalyst supports and adsorbents. Catalyst compositions including these shaped porous carbon products, processes of preparing the catalyst compositions, and various processes of using the shaped porous carbon products and catalyst compositions are also provided.

PROCESS FOR THE SELECTIVE PRODUCTION OF PROPANOLS BY HYDROGENATION OF GLYCEROL

The present invention discloses a process for the selective hydrogenation of glycerol in the liquid phase to produce 1- and 2-propanols in high yields as the major organic products. The process comprises subjecting a glycerol stream having at least 30% by weight water to a combination of low pressure and high temperature hydrogenation conditions in the presence of a promoted or un-promoted skeletal copper catalyst. 1. A catalytic process for the hydrogenation of glycerol comprisinga) obtaining a glycerol-containing stream having a water content of at least 30% by weight of the total glycerol containing stream; andb) subjecting the glycerol-containing stream to hydrogenation in the liquid phase in a reactor in the presence of a skeletal copper catalyst at a reaction temperature of greater than 250° C., and a reaction pressure of less than 100 bar.2. The catalytic process of wherein the skeletal copper catalyst is promoted with at least one transition metal other than copper selected from the group consisting of Groups 4 claim 1 , 6 claim 1 , 7 claim 1 , 8 claim 1 , 9 claim 1 , 10 and 12 of the Periodic Table of Elements claim 1 , and combinations thereof.3. The catalytic process of wherein the skeletal copper catalyst is promoted with a transition metal selected from the group consisting of nickel claim 2 , cobalt claim 2 , molybdenum claim 2 , zinc claim 2 , chromium claim 2 , zirconium and combinations thereof.4. The catalytic process of wherein the reaction temperature is from about 260° C. to about 320° C.5. The catalytic process of wherein the reaction temperature is from about 270° C. to about 310° C.6. The catalytic process of wherein the reaction pressure is less than 60 bar.7. The catalytic process of wherein the reaction pressure ranges from about 10 bar to about 50 bar.8. The catalytic process of wherein the water content of the glycerol is at least 50% by weight based on the total weight of the glycerol feed.9. The catalytic process of wherein a glycerol ...

MANGANESE OXIDE-STABILIZED ZIRCONIA CATALYST SUPPORT MATERIALS

The present disclosure relates generally to catalyst support materials, catalysts and methods for using them, such as methods for converting sugars, sugar alcohols, glycerol, and bio-renewable organic acids to commercially-valuable chemicals and intermediates. One aspect of the invention is catalyst support material including ZrOand one or more oxides of manganese (MnO), the catalyst support material being at least about 50 wt % ZrOand MnO. In certain embodiments, the weight ratio of ZrOto MnOis within the range of about 1:1 to about 30:1; and/or the catalyst support material is substantially free of any binder, extrusion aid or additional stabilizing agent. 1. A catalyst support material comprising ZrOand one or more oxides of manganese (MnO) the catalyst support material containing at least about 1 wt % to about 50 wt % of MnO.2. A catalyst support material according to claim 1 , wherein the catalyst support material being at least 50 wt % ZrOand MnO.3. A catalyst support material according to claim 1 , wherein the catalyst support material further comprises nickel oxide claim 1 , the catalyst support material containing at least about 1 wt % to about 50 wt % of MnOand at least 1 wt. % to 10 wt. % nickel oxide.4. A catalyst support material according to claim 1 , wherein the weight ratio of ZrOto MnOis within the range of about 1:1 to about 30:1.5. A catalyst support material according to claim 1 , further comprising oxides of yttrium and/or lanthanum claim 1 , wherein the molar ratio of the ZrOto the oxides of yttrium and/or lanthanum is within the range of about 10:1 to about 100:1.6. A catalyst support material according to claim 1 , wherein the catalyst support material has a pore volume within the range of about 0.1 to about 0.5 cm/g.7. A catalyst support material according to claim 1 , wherein the catalyst support material has a surface area within the range of about 10 to about 400 m/g.8. A catalyst support material according to claim 1 , wherein the ...

METHODS FOR PRODUCING 2,6-DIMETHYL-1,5-HEPTADIEN-3-OL AND 2,6-DIMETHYL-1,5-HEPTADIEN-3-YL ACETATE

Provided are industrial and economical methods for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate (3), which is, for example, a sex pheromone component of Comstock mealybug, and 2,6-dimethyl-1,5-heptadien-3-ol (2), which is an intermediate of the acetate (3). More specifically, provided are a method for producing 2,6-dimethyl-1,5-heptadien-3-ol comprising a step of subjecting 2-methyl-3-buten-2-yl 2-methyl-2-propenyl ether (1) to a rearrangement reaction in the presence of a base to obtain 2,6-dimethyl-1,5-heptadien-3-ol (2), and a method for producing 2,6-dimethyl-1,5-heptadien-3-yl acetate comprising a step of acetylating the produced 2,6-dimethyl-1,5-heptadien-3-ol (2) to obtain 2,6-dimethyl-1,5-heptadien-3-yl acetate (3). 2. The method for producing 2 claim 1 ,6-dimethyl-1 claim 1 ,5-heptadien-3-ol according to claim 1 , wherein the base is selected from the group consisting of metal alkoxides claim 1 , organometallic compounds claim 1 , and metal amides.4. The method for producing 2 claim 3 ,6-dimethyl-1 claim 3 ,5-heptadien-3-yl acetate according to claim 3 , wherein the base is selected from the group consisting of metal alkoxides claim 3 , organometallic compounds claim 3 , and metal amides. The invention relates to 2,6-dimethyl-1,5-heptadien-3-yl acetate, which is a sex pheromone component of Comstock mealybug (scientific name: ), and 2,6-dimethyl-1,5-heptadien-3-ol, which is an intermediate thereof.Since Comstock mealybug (scientific name: ) damages many fruit trees such as apples, pears, peaches and grapes and the excrement of this insect pest causes plant diseases, yield reduction and quality deterioration of these fruits have become a serious problem. At present, insecticides are used for the control of Comstock mealybug. However, they do not have a sufficient effect against the body of mealybugs covered with a waxy substance. Further, in order to prevent the insecticides from remaining on or in crops or prevent them from affecting the environment or ...

GLYCERIN-ONLY REACTION FOR ALLYL ALCOHOL PRODUCTION

A process of producing allyl alcohol by reacting glycerin with ReO—AlOin the presence of gamma-valerolactone (GVL) in a reactor is described. More specifically, a process to produce allyl alcohol, comprising the step of: a) reacting glycerin with ReO—AlOin the presence of an inert solvent, GVL, in a reactor, and b) collecting the product comprising allyl alcohol. 1. A process to produce allyl alcohol , comprising the step of:{'sub': 3', '2', '3, 'a) reacting glycerin with ReO—AlOin the presence of an inert solvent in a reactor, wherein the inert solvent is gamma-valerolactone (GVL); and'}b) collecting the product comprising allyl alcohol.2. The process of claim 1 , wherein the process is free of additional reducing agent.3. The process of claim 1 , wherein the reaction is further carried out in the presence of at least two inert solvents.4. The process of claim 3 , wherein at least one of the two inert solvents is tetraethylene glycol dimethyl ether (tetraglyme).5. The process of claim 1 , wherein the molar ratio of the inert solvent to glycerin ranges from 2:1 to 1:2.6. The process of claim 1 , wherein the reactor is maintained at 180-200° C. for 4 hours. The process of claim 1 , further comprising pretreating the glycerin.87. The process of claim claim 1 , wherein the pretreating step comprises washing the glycerin with an acid or treating the glycerin with an ion exchange resin.9. The process of claim 8 , wherein the ion exchange resin is a macroreticular sulfonated polystyrene-divinylbenzene resin.107. The process of claim claim 8 , wherein the pretreating step further comprises washing the glycerin with water.11. The process of claim 1 , wherein the product comprises a vapor component and a liquid component.12. The process of claim 11 , further comprising removing the vapor component from the reactor.13. The process of claim 11 , further comprising distilling the vapor component with a solvent.14. The process of claim 11 , further comprising removing the ReO— ...

PROCESS FOR CATALYTIC PRODUCTION OF PROPANOL

The present disclosure is related to a multistep process for producing renewable gasoline components from a glyceride containing feedstock. The glycerides are split to provide a stream containing fatty acids, or esters of fatty acids, and another stream containing glycerol and water. Glycerol, preferably as crude glycerol recovered from splitting, is next converted to propanols at vapor phase, providing a renewable propanol gasoline component. Another renewable gasoline component is obtained from hydroprocessing of the fatty acids or esters thereof, as a renewable paraffinic naphtha component. Blending the renewable components can provide a novel 100% renewable gasoline. 1. A process for producing renewable fuel components , said process comprising steps a.-e. of ,a. providing a glyceride containing feedstock; andb. splitting said glyceride containing feedstock to provide a first stream containing at least one or more of fatty acids, or esters of fatty acids, and a second stream containing glycerol and water; and i. at least one evaporation in a presence of 5-90%-wt water of a total second stream weight, wherefrom a vapor phase is directed to:', 'ii. catalytic conversion of glycerol to 1-propanol, 2-propanol or a mixture thereof at vapor phase in presence of water and hydrogen, and', 'iii. separation and recovery of 1-propanol, 2-propanol or a mixture thereof as a renewable propanol gasoline component;, 'c. subjecting said second stream obtained from step b, tod. subjecting said first stream to hydroprocessing, to provide a first product stream of renewable paraffinic fuel components containing i-paraffins and n-paraffins; ande. separating said first product stream, and recovering renewable fuel components containing at least one renewable paraffinic naphtha component.2. The process according to claim 1 , for producing renewable fuel components claim 1 , said process comprising:b′. separating the first stream obtained from step b into at least two fatty acid or ...

IMPROVED PROCESS OF MAKING BIODERIVED PROPYLENE GLYCOL

An improved process for making bioderived propylene glycol from a feed composition including at least one of lactic acid, glycerol, a five carbon sugar, a five carbon sugar alcohol, a six carbon sugar and a six carbon sugar alcohol, wherein production of four carbon and higher diols is reduced by adding base after the initiation of the reaction. In preferred embodiments, the process pH and other process conditions are initially established at targeted values for obtaining the highest conversion for a given catalyst consistent with the production of substantially no pentanediol byproducts in the product mixture, and base is added thereafter to control the process pH proximate to the initially targeted value. 1. In a process of making bioderived propylene glycol by reacting a feed composition including at least one of lactic acid , glycerol , a five carbon sugar , a five carbon sugar alcohol , a six carbon sugar and a six carbon sugar alcohol with hydrogen in the presence of a suitable catalyst for catalyzing the reaction and under conditions effective for carrying out the reaction , the improvement comprising adding base to the reactor after the initiation of the reaction.2. An improved process according to claim 1 , further comprising adding base to the feed composition and hydrogen entering the reactor claim 1 , in an amount at least sufficient to improve the conversion of the at least one of lactic acid claim 1 , glycerol claim 1 , a five carbon sugar claim 1 , a five carbon sugar alcohol claim 1 , a six carbon sugar and a six carbon sugar alcohol as compared to a scenario wherein no base is added either prior to or after initiation of the reaction claim 1 , but less than that amount of base at which a pentanediol byproduct begins to be formed at detectable levels under the same conditions.3. An improved process according to claim 2 , wherein the process is a continuous process and wherein base is added to the reactor in at least one location downstream of the ...

Methods for Preparing Diol

Provided is a method for preparing a diol. In the method, a saccharide and hydrogen as raw materials are contacted with a catalyst in water to prepare the diol. The employed catalyst is a composite catalyst comprised of a main catalyst and a cocatalyst, wherein the main catalyst is a water-insoluble acid-resistant alloy; and the cocatalyst is a soluble tungstate and/or soluble tungsten compound. The method uses an acid-resistant, inexpensive and stable alloy needless of a support as a main catalyst, and can guarantee a high yield of the diol in the case where the production cost is relatively low. 1. A method for preparing a diol , characterized by:(a) adding an unsupported main catalyst comprising nickel, one or more rare earth elements, tin and aluminium, and optionally i) tungsten, ii) tungsten and molybdenum, or iii) tungsten, molybdenum and boron or phosphorus to a slurry bed reactor;(b) increasing the reaction system pressure to 5-12 MPa and the reaction temperature to 150-260° C.;(c) adding a soluble tungstic acid salt cocatalyst, hydrogen and a sugar to the slurry bed reactor, wherein the sugar and cocatalyst are fed continuously into the slurry bed reactor in the form of an aqueous sugar solution having a sugar concentration from 20-60 wt % and further comprising the soluble tungstic acid salt cocatalyst to provide gas and a liquid comprising a diol;(d) continuously passing the gas and reaction liquid out of the reactor through a filter to intercept catalyst and(e) separating the diol from the gas and reaction liquid.2. The method for preparing a diol as claimed in claim 1 , characterized in that the diol is ethylene glycol.3. The method for preparing a diol as claimed in claim 2 , characterized in that the reaction system pH is 1-7; more preferably claim 2 , the reaction system pH is 3-6.4. The method for preparing a diol as claimed in claim 1 , characterized in that the sugar is selected from one or more of five-carbon monosaccharides claim 1 , ...

PROCESS FOR THE PRODUCTION OF ALKYLENE GLYCOLS

The invention provides a process for the production of alkylene glycols, said process comprising providing a feed comprising at least 10 wt % of lignocellulose and/or one or more saccharides, on the basis of the overall feed, in water to a reactor; also providing a feed comprising one or more hydrogen-donating organic solvent species to the reactor; contacting the lignocellulose and/or one or more saccharides in the reactor with a retro-aldol catalyst composition at a temperature in the range of from at least 160 to at most 270° C., wherein the combined solvent system within the reactor comprises in the range of from at least 5 to at most 95 wt % of one or more hydrogen-donating organic solvent species and in the range of from at least 5 to at most 95 wt % of water. 1. A process for the production of alkylene glycols , said process comprising providing a feed comprising at least 10 wt % of lignocellulose and/or one or more saccharides , on the basis of the overall feed , in water to a reactor; also providing a feed comprising one or more hydrogen-donating organic solvent species to the reactor; contacting the lignocellulose and/or one or more saccharides in the reactor with a retro-aldol catalyst composition at a temperature in the range of from at least 160 to at most 270° C. , wherein the combined solvent system within the reactor comprises in the range of from at least 5 to at most 95 wt % of one or more hydrogen-donating organic solvent species and in the range of from at least 5 to at most 95 wt % of water.2. The process according to claim 1 , wherein the hydrogen-donating organic solvent species is selected from the group consisting of secondary alcohols claim 1 , glycols claim 1 , hydroquinone claim 1 , formic acid and sugar alcohols.3. The process as claimed in claim 2 , wherein the hydrogen-donating organic solvent species is selected from isopropyl alcohol claim 2 , glycerol claim 2 , erythritol claim 2 , threitol claim 2 , sorbitol claim 2 , xylitol claim ...

PROCESSES TO CREATE MULTIPLE VALUE STREAMS FROM BIOMASS SOURCES

Use of diverse biomass feedstock in a process for the recovery of target C5 and C6 alditols and target glycols via staged hydrogenation and hydrogenolysis processes is disclosed. Particular alditols of interest include, but are not limited to, xylitol and sorbitol. Various embodiments of the present invention synergistically improve overall recovery of target alditols and/or glycols from a mixed C5/C6 sugar stream without needlessly driving total recovery of the individual target alditols and/or glycols. The result is a highly efficient, low complexity process having enhanced production flexibility, reduced waste and greater overall yield than conventional processes directed to alditol or glycol production. 1. A process , comprising:selecting a target alditol or a target blend of alditols,hydrogenating continuously a mixed C5/C6 monomer sugar stream to form a mixed C5/C6 alditol stream;isolating the target alditol or target blend of alditols from the mixed C5/C6 alditol stream to leave a residual mixed C5/C6 alditol stream;continuous hydrogenolysis of the residual mixed C5/C6 alditol stream to form a mixed C2-C4 glycol stream; andisolating a target glycol or target blend of glycols from the mixed C2-C4 glycol stream;wherein at least 10% of the overall target product yield is either target alditol/target blend of alditols or target glycol/target blend of glycols.23.-. (canceled)4. The process of claim 1 , wherein the monomer sugar stream or the mixed C5/C6 monomer sugar stream comprises greater than or equal to 60% C5 monomer sugar based on the combined total of C5 and C6 monomer sugars claim 1 , specifically greater than or equal to 65% C5 monomer sugar claim 1 , and more specifically greater than or equal to 70% C5 monomer sugar; orwherein the monomer sugar stream or the mixed C5/C6 monomer sugar stream comprises greater than or equal to 60% C6 monomer sugar based on the combined total of C5 and C6 monomer sugars, specifically greater than or equal to 65% C6 ...

SYNTHESIS OF R-GLUCOSIDES, SUGAR ALCOHOLS, REDUCED SUGAR ALCOHOLS, AND FURAN DERIVATIVES OF REDUCED SUGAR ALCOHOLS

Disclosed herein are methods for synthesizing 1,2,5,6-hexanetetrol (HTO), 1,6 hexanediol (HDO) and other reduced polyols from C5 and C6 sugar alcohols or R glycosides. The methods include contacting the sugar alcohol or R-glycoside with a copper catalyst, most desirably a Raney copper catalyst with hydrogen for a time, temperature and pressure sufficient to form reduced polyols having 2 to 3 fewer hydoxy groups than the starting material. When the starting compound is a C6 sugar alcohol such as sorbitol or R-glycoside of a C6 sugar such as methyl glucoside, the predominant product is HTO. The same catalyst can be used to further reduce the HTO to HDO. 1. A method of making a reduced sugar alcohol including at least one member selected from the group consisting of 1 ,2 ,5-pentanetriol , 1 ,4 ,5-hexanetriol , 1 ,2 ,6-hexanetetrol , and 1 ,2 ,5 ,6 hexanetetrol , comprising ,contacting a solution comprising water and at least 20% wt/wt of a starting compound selected from the group consisting of a sugar alcohol and a R-glycoside of a sugar, wherein R is a methyl or ethyl group, with hydrogen and a Raney copper catalyst for a time and at a temperature and pressure sufficient to produce a mixture containing one or more of the reduced sugar alcohols with a combined selectively yield of at least 50% mol/mol.2. The method of claim 1 , wherein the starting compound is a C6 sugar alcohol selected from the group consisting of sorbitol claim 1 , mannitol claim 1 , ididtol claim 1 , dulcitol claim 1 , talitol claim 1 , and 1 claim 1 ,4-sorbitan and the reduced sugar alcohol is at least one of 1 claim 1 ,4 claim 1 ,5-hexanetriol and 1 claim 1 ,2 claim 1 ,5 claim 1 ,6-hexanetetrol.3. The method of wherein the starting compound is a methyl or ethyl glucoside and reduced sugar alcohol is at least one of 1 claim 1 ,4 claim 1 ,5-hexanetriol and 1 claim 1 ,2 claim 1 ,5 claim 1 ,6-hexanetetrol.4. The method of claim 1 , wherein the temperature is 175° C. to 250° C. and the pressure is ...

MIXED CARBON LENGTH SYNTHESIS OF PRIMARY GUERBET ALCOHOLS

In an embodiment of the disclosure, mixtures of different carbon length alcohols are used as the primary feedstock for Guerbet alcohols. Specifically, embodiments relate to a method of synthesizing mixed molecular weight additives from a mixture of primary alcohols comprising, receiving a mixture of primary alcohols having greater than two different chain length primary alcohols and reacting the mixture of primary alcohols in a single reactor to produce a mixture of at least five Guerbet alcohols. The mixture of Guerbet alcohols can then be used to produce an additive or surfactant composition comprising additives or surfactants of different molecular weights. 1. A method of synthesizing mixed chain length surfactants from a mixture of primary alcohols , the method comprising:receiving a mixture of primary alcohols comprising greater than two different chain length primary alcohols in equal parts of each primary alcohol; i. the number of Guerbet alcohols produced is equal to twice the number of primary alcohols minus one;', 'ii. the mixture of at least five Guerbet alcohols comprises a lowest molecular weight Guerbet alcohol, a highest molecular weight Guerbet alcohol, a Guerbet alcohol having a molecular weight halfway between the molecular weight of the lowest molecular weight Guerbet alcohol and the highest molecular weight Guerbet alcohol;', 'iii. the Guerbet alcohol having the molecular weight halfway between the molecular weight of the lowest molecular weight Guerbet alcohol and the highest molecular weight Guerbet alcohol has a highest concentration of the Guerbet alcohols in the mixture of at least five Guerbet alcohols;', 'iv. the lowest molecular weight Guerbet alcohol and the highest molecular weight Guerbet alcohol each have a lowest concentration of the Guerbet alcohols in the mixture of at least five Guerbet alcohols; and', 'v. remaining Guerbet alcohols in the mixture of at least five Guerbet alcohols have concentrations increasing as molecular weight ...

PROCESS FOR THE CONVERSION OF SACCHARIDE-CONTAINING FEEDSTOCK

The invention provides a process for the catalytic conversion of a saccharide-containing feedstock in a reactor, wherein saccharide-containing feedstock is provided to the reactor as a feed stream through a feed pipe and is contacted with a catalyst system in the reactor and a reaction product is continuously removed from the reactor and wherein the saccharide-containing feedstock is provided through the feed pipe as a pulsed flow and is alternated with a second feed stream comprising a solvent being provided through the same feed pipe. 1. A process for the catalytic conversion of asaccharide-containing feedstock in a reactor, wherein saccharide-containing feedstock is provided to the reactor as a feed stream through a feed pipe and is contacted with a catalyst system in the reactor and a reaction product is continuously removed from the reactor and wherein the saccharide-containing feedstock is provided through the feed pipe as a pulsed flow and is alternated with a second feed stream comprising a solvent being provided through the same feed pipe.2. A process according to claim 1 , wherein the flow of the saccharide containing feedstock is turned on and off such that when the flow of the saccharide containing feedstock is turned off claim 1 , the amount of saccharide entering the reactor is reduced by at least 90% when compared with when the flow of the saccharide containing feedstock is turned on.3. A process according to claim 1 , wherein the second feed stream is provided to the reactor for at least 90% of the time in which the flow of the saccharide containing feedstock is turned off.4. A process according to claim 1 , wherein the ratio of the time in which the flow of the saccharide containing feedstock is turned on to the time in which the flow of the saccharide containing feedstock is turned off is in the range of from 0.5:1 to 20:1.5. A process according to claim 1 , wherein the saccharide containing feedstock is also contacted with hydrogen in the reactor. ...

PROCESS FOR THE TRANSFORMATION OF LIGNOCELLULOSIC BIOMASS INTO MONO- OR POLY-OXYGENATED MOLECULES

The invention concerns a process for the transformation of lignocellulosic biomass or cellulose into mono- or poly-oxygenated compounds, in which the lignocellulosic biomass or the cellulose is brought into simultaneous contact with a catalytic system comprising a combination of one or more homogeneous catalysts and one or more heterogeneous catalysts, in the same reaction chamber, in the presence of at least one solvent, said solvent being water alone or as a mixture with at least one other solvent, in a reducing atmosphere, and at a temperature in the range 80° C. to 250° C. and at a pressure in the range 0.5 MPa to 20 MPa. 1. A process for the transformation of lignocellulosic biomass or cellulose into mono- or poly-oxygenated compounds , in which the lignocellulosic biomass or the cellulose is brought into simultaneous contact with a combination of one or more homogeneous catalysts and one or more heterogeneous catalysts in the same reaction chamber , in the presence of at least one solvent , said solvent being water alone or as a mixture with at least one other solvent , in a reducing atmosphere , and at a temperature in the range 80° C. to 250° C. and at a pressure in the range 0.5 MPa to 20 MPa ,{'sub': n', '2, 'said homogeneous catalyst or catalysts comprising a metallic salt which may or may not be hydrated with general formula MX.n′HO in which M is a metal selected from the metals from groups 3 to 16 of the periodic classification, n is a whole number in the range 1 to 6 and n′ is a whole number in the range 0 to 6 and X is at least one anion selected from halides, nitrates, carboxylates, halocarboxylates, acetylacetonates, alcoholates, phenolates, which may or may not be substituted, sulphates, alkylsulphates, phosphates, alkylphosphates, halo sulphonates, alkylsulphonates, perhaloalkylsulphonates, bis(perhaloalkylsulphonyl)amides, arenesulphonates, which may or may not be substituted with halogen or haloalkyl groups, said anions X possibly being ...

PROCESS FOR THE PRODUCTION OF ALKENOLS AND USE THEREOF FOR THE PRODUCTION OF 1,3-BUTADIENE

Process for the production of alkenols comprising the dehydration of at least one diol in the presence of at least one catalyst based on cerium oxide, wherein said catalyst based on cerium oxide is obtained by precipitation, in the presence of at least one base, of at least one compound containing cerium. Preferably, said diol may be a butanediol, more preferably 1,3-butanediol, still more preferably bio-1,3-butanediol derived from biosynthetic processes. Said alkenols may advantageously be used for the production of 1,3-butadiene, in particular of bio-1,3-butadiene. 1. Process for the production of alkenols comprising the dehydration of at least one diol , in the presence of at least one catalyst based on cerium oxide , wherein said catalyst based on cerium oxide is obtained by precipitation , in the presence of at least one base , of at least one compound containing cerium.2. Process for the production of alkenols according to claim 1 , wherein said process is carried out in the presence of at least one diluent.3. Process for the production of alkenols according to claim 1 , wherein said catalyst based on cerium oxide is obtained by a process comprising:preparing a solution including at least one compound containing cerium;adding to said solution at least one base in a time ranging from 1 minute to 16 hours, to obtain a reaction mixture;allowing said reaction mixture to react at a temperature ranging from 15° C. to 100° C., for a time ranging from 1 minute to 120 hours, to obtain a precipitate;recovering the precipitate and subjecting it to drying and, optionally, to calcination.4. Process for the production of alkenols according to claim 1 , wherein said catalyst based on cerium oxide is obtained by a process comprising:preparing a solution including at least one base;adding to said solution at least one compound containing cerium in a time ranging from 1 minute to 16 hours, to obtain a reaction mixture;allowing said reaction mixture to react at a temperature ...

PROCESS FOR PRODUCING ETHANOL FROM METHYL ACETATE

The present invention relates to a process for producing ethanol by methyl acetate hydrogenolysis. The process comprises the step of reacting carbon monoxide and methanol in a reaction medium to form a reaction solution that comprises acetic acid and from 0.5 to 25 wt. % methyl acetate. The process further comprises the step of esterifying the acetic acid and feeding the methyl acetate to a distillation column to remove alkyl halides. The process further comprises the steps of reacting the methyl acetate stream that does not contain alkyl halides and hydrogen in the presence of a second catalyst to form an alcohol product that comprises ethanol and/or methanol. 1. A process for producing ethanol by hydrogenolysis of methyl acetate comprising:reacting carbon monoxide and methanol in a reaction medium to form a reaction solution that comprises acetic acid and from 0.5 to 25 wt. % methyl acetate, wherein the reaction medium comprises water, acetic acid, methyl acetate, a first catalyst, and an alkyl halide;flashing the reaction solution to yield a carbonylation product and a liquid catalyst recycle stream;separating the carbonylation product into a first methyl acetate stream and acetic acid stream;esterifying the acetic acid stream to form a second methyl acetate stream;feeding the first methyl acetate stream and the second methyl acetate stream to a distillation column to remove alkyl halides and obtain a third methyl acetate stream;reacting the third methyl acetate stream and hydrogen in the presence of a second catalyst to form an alcohol product that comprises ethanol and methanol; andrecovering ethanol from the alcohol product.2. The process of claim 1 , wherein the third methyl acetate stream comprises at least 60 wt. % methyl acetate.3. The process of claim 1 , wherein the third methyl acetate stream comprises less than 5 wt. % acetic acid.4. The process of claim 1 , wherein the third methyl acetate stream is substantially free of methyl iodide.5. The process ...

PROCESS FOR THE PRODUCTION OF ALLYL COMPOUNDS BY DEOXYDEHYDRATION OF GLYCEROL

A continuous-flow process for the production of allyl compounds by deoxydehydration of glycerol includes: 1. A continuous-flow process for the production of allyl compounds by deoxydehydration of glycerol comprising:{'b': '1', 'claim-text': [{'b': '2', 'a carboxylic acid (), or'}, 'a triethyl orthoester, preferably triethyl orthoformate (TEOF), or a combination thereof;, '(a) Forming a reactive solution by mixing glycerol () with(b) Feeding the reactive solution to an inlet of a channel of a thermolysis microreactor module wherein the channel has an inner hydraulic diameter, D=4 A/P, wherein A is the area and P the perimeter of a cross-section of the channel, of not more than 1000 μm,(c) Exposing the reactive solution to thermolysis by driving a flow of the reactive solution along the channel from the inlet to an outlet, for a thermolysis time, t, at a pressure, P, and at a thermolysis temperature, T, larger than 200° C., to form thermolysis products including at least one allyl compound; and(d) Recovering the thermolysis products at the outlet and separating the at least one allyl compound from the other thermolysis products.2. The continuous-flow process according to claim 1 , wherein claim 1 ,the triethyl orthoester is present in the reactive solution in an amount comprised between 1 and 3, or{'b': '2', 'the carboxylic acid () is present in the reactive solution in an amount comprised between 1 and 3, or a combination thereof.'}3. The continuous-flow according to claim 1 , wherein claim 1 ,the triethyl orthoester is present in the reactive solution in an amount comprised between 1 and 3 equivalent, and{'b': '2', 'the carboxylic acid () is present in the reactive solution in an amount comprised between 0.001 and 1.5 equivalent.'}4. The continuous-flow process according to claim 1 , wherein the at least one allyl compound present in the thermolysis products comprises allyl alcohol and allyl formate claim 1 , wherein the 3a/3b ratio defined as the relative content ...

Process for the preparation of glycols

The invention provides a process for the preparation of ethylene glycol and 1,2-propylene glycol from starting material comprising one or more saccharides, by contacting said starting material with hydrogen in a reactor in the presence of a solvent and a catalyst system with catalytic hydrogenation abilities, wherein the process comprises the steps of: i) introducing a first portion of the starting material into the reactor such that the initial concentration of the saccharide in the solvent in the reactor is no more than 2 wt %; ii) allowing at least 90 wt % of the saccharide in the first portion of the starting material to react; iii) subsequently adding further portions of starting material to the reactor over time; and removing reaction product from the reactor.

PROCESSES AND SYSTEMS FOR THE PRODUCTION OF PROPYLENE GLYCOL FROM GLYCEROL

Processes and systems for converting glycerol to propylene glycol are disclosed. The glycerol feed is diluted with propylene glycol as the primary solvent, rather than water which is typically used. The diluted glycerol feed is sent to a reactor where the glycerol is converted to propylene glycol (as well as other byproducts) in the presence of a catalyst. The propylene glycol-containing product from the reactor is recycled as a solvent for the glycerol feed. 111-. (canceled)13. The process of further comprising reacting the diluted feed with the catalyst after recycling back the product and soluble base.14. The process of wherein up to about 60% of the product is recycled back into the feed.15. The process of wherein the feed was derived from a biodiesel process.16. The process of wherein the diluted glycerol feed comprises from about 40% to 60% by weight glycerol.17. The process of wherein the diluted glycerol feed comprises from about 40% to 60% by weight propylene glycol.18. The process of wherein the reaction is carried out at a temperature from about 160° C. to about 240° C.19. The process of wherein the reaction is carried out at a pressure from about 400 to about 1600 psi.20. The process of wherein the recycled product comprises less than about 20% water by weight.21. The process of wherein further reacting the diluted feed with the catalyst after recycling the product and soluble base results in about 70% or greater selectivity to propylene glycol.22. The process of wherein the feed comprises less than about 12% water by weight.2340-. (canceled) This invention was made with Government support under Contract DE-AC06-76RL01830 awarded by the U.S. Department of Energy. The Government has certain rights in the invention.This disclosure relates to processes and systems for the conversion of glycerol to propylene glycol, including processes that recycle the propylene glycol product stream to serve as a solvent for the glycerol feed stream.It is known to convert ...

HYDROTHERMAL HYDROCATALYTIC TREATMENT OF BIOMASS USING WATER TOLERANT CATALYSTS

A method of hydrothermal hydrocatalytic treating biomass is provided. Lignocellulosic biomass solids is provided to a hydrothermal digestion unit in the presence of a digestive solvent, and a supported hydrogenolysis catalyst containing (a) sulfur, (b) Mo or W, and (c) Co, Ni or mixture thereof, incorporated into a group 4 metal oxide support; (ii) heating the lignocellulosic biomass solids and digestive solvent in the presence of hydrogen, and the supported hydrogenolysis catalyst thereby forming a product solution containing plurality of oxygenated hydrocarbons, said catalyst retaining a crush strength of at least 50% after being subjected to an aqueous phase stability test compared with before the aqueous phase stability test or a crush strength of at least 0.25 kg after being subjected to an aqueous phase stability test. 1. A method comprising: (i) providing lignocellulosic biomass solids in a hydrothermal digestion unit in the presence of a digestive solvent , and a supported hydrogenolysis catalyst containing (a) sulfur , (b) Mo or W , and (c) Co , Ni or mixture thereof , incorporated into a group 4 metal oxide support; (ii) heating the lignocellulosic biomass solids and digestive solvent in the presence of hydrogen , and supported hydrogenolysis catalyst thereby forming a product solution containing plurality of oxygenated hydrocarbons , said catalyst retaining a crush strength of at least 50% after being subjected to an aqueous phase stability test compared with before the aqueous phase stability test.2. The method of wherein the lignocellulosic biomass solids is heated to a temperature in the range of 180° C. to less than 300° C.3. The method of wherein the catalyst retains aqueous phase stability of at least 60% after being subjected to an aqueous phase stability test.4. The method of wherein the group 4 metal oxide support is a stabilized form.5. The method of wherein the group 4 metal oxide support is zirconia.6. The method of wherein the group 4 metal ...

PRODUCTION OF ALPHA, OMEGA-DIOLS

Disclosed herein are processes for preparing an α,ω-C-diol, wherein n is 5 or greater, from a feedstock comprising a Coxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising Pt, Cu, Ni, Pd, Pt, Rh, Ir, Ru, or Fe on a WOor WOsupport. In one embodiment, the process comprises contacting the feedstock with hydrogen in the presence of a catalyst comprising a metal M1 and a metal M2 or an oxide of M2, and optionally a support. In one embodiment, M1 is Pd, Pt, or Ir; and M2 is Mo, W, V, Mn, Re, Zr, Ni, Cu, Zn, Cr, Ge, Sn, Ti, Au, or Co. The Coxygenate may be obtained from a biorenewable resource. 2. The process of claim 1 , wherein n=5 or 6.3. The process of wherein the optional support is present in the catalyst and comprises WO claim 1 , SiO claim 1 , AlO claim 1 , carbon claim 1 , TiO claim 1 , ZrO claim 1 , SiO—AlO claim 1 , montmorillonite claim 1 , SiO-TiO claim 1 , tungstated ZrO claim 1 , zeolites claim 1 , VO claim 1 , MoO claim 1 , or mixtures thereof.4. The process of wherein the Coxygenate comprises 1 claim 1 ,2 claim 1 ,6-hexanetriol; 1 claim 1 ,2 claim 1 ,5-pentanetriol; 2H-tetrahydropyran-2-methanol; tetrahydrofuran-2 claim 1 ,5-dimethanol; furan-2 claim 1 ,5-dimethanol; 2 claim 1 ,5 dihydrofuran-2 claim 1 ,5-dimethanol; levoglucosenone; levoglucosan; levoglucosenol; 1 claim 1 ,6-anhydro-3 claim 1 ,4-dideoxy-p-D-pyranose-2-one; isosorbide; hydroxymethylfurfural; sorbitol; glucose; fructose; xylitol; 3 claim 1 ,4-dihydro-2H-pyran-2-carbaldehyde; 1 claim 1 ,2 claim 1 ,5 claim 1 ,6-hexanetetraol; 1 claim 1 ,2 claim 1 ,3 claim 1 ,5 claim 1 ,6-hexanepentanol; 1 claim 1 ,5-anhydro-3 claim 1 ,4-dideoxy-hexitol; 5-hydroxy-2H-tetrahydropyran-2 methanol; furfural; furfuryl alcohol; tetrahydrofurfuryl alcohol; pentoses; dimers containing pentose; oligomers containing pentose; hexoses; dimers containing hexose; oligomers containing hexose; condensation products from the reaction of 5-( ...

Process to recover 3-methyl-but-3-en-1-ol

The presently claimed invention relates to a process for the recovery of 3-methyl-3-buten- -ol from a stream comprising (Z)-3-methylpent-2-ene-1,5-diol, (E)-3-methylpent-2-ene-,5-diol and 3-methylenepentane-1,5-diol by treating the stream with isobutene and water.

PROCESS FOR PRODUCING DIMETHYL CARBONATE

The present disclosure relates to a recycling method for producing dimethyl carbonate and dimethyl carbonate derivatives. The process is unique in that it produces a by-product that can be re-used in the process as a raw material for repeating the process. For example, when the process is directed to synthesizing dimethyl carbonate, glycerol is used as a starting material. Glycerol is also a by-product produced during formation of dimethyl carbonate, and therefore it can be re-used as starting material to generate more dimethyl carbonate. 2. The process of claim 1 , wherein the halogenating agent in (a) is hydrogen chloride or a mixture of gaseous hydrogen chloride and an aqueous solution of hydrogen chloride.3. The process of claim 1 , wherein the reaction of the compound of formula (I) with the halogenating agent in (a) is carried out in the presence of a catalyst.4. The process of claim 3 , wherein the catalyst is an organic acid catalyst claim 3 , an inorganic acid catalyst claim 3 , or a heterogeneous acid catalyst.5. The process of claim 4 , wherein the catalyst is an organic acid catalyst selected from the group consisting of a carboxylic claim 4 , a sulfonic claim 4 , and a phosphoric acid.6. The process of claim 1 , wherein the base in (b) is selected from the group consisting of a hydroxide claim 1 , a carbonate and a bicarbonate of alkali metal claim 1 , alkaline earth metal claim 1 , and a basic ion exchange resin.7. The process of claim 6 , wherein the base in (b) is selected from the group consisting of LiOH claim 6 , NaOH claim 6 , KOH claim 6 , CsOH claim 6 , RbOH claim 6 , Mg(OH) claim 6 , Ca(OH) claim 6 , Sr(OH) claim 6 , NHOH claim 6 , Ba(OH) claim 6 , NaCO claim 6 , and KCO claim 6 , NaHCOand KHCO.8. The process of claim 1 , wherein the reaction of the compound of Formula (III) with carbon dioxide in (c) is carried out in the presence of a catalyst.9. The process of claim 9 , wherein the catalyst is an alkali metal halide salt or quaternary ...

Method for producing allyl alcohol and allyl alcohol produced thereby

Disclosed are a method of preparing allyl alcohol and allyl alcohol prepared thereby. The method of preparing allyl alcohol includes adding glycerol with formic acid in an amount of 0.8˜2 equivalents relative to 1 equivalent of glycerol, and increasing a reaction temperature to 220˜260° C. from room temperature at a heating rate of 2.0˜7.0° C./min so that glycerol and formic acid are reacted.

POROUS SHAPED METAL-CARBON PRODUCTS

The present invention provides a porous metal-containing carbon-based material that is stable at high temperatures under aqueous conditions. The porous metal-containing carbon-based materials are particularly useful in catalytic applications. Also provided, are methods for making and using porous shaped metal-carbon products prepared from these materials. 1. A process for preparing a porous , shaped metal-carbon product , the process comprising:mixing a carbonaceous material with water, a water-soluble organic binder, and a (first) metal precursor to form a metal-carbon mixture, wherein the metal precursor is a compound selected from the group consisting of a metal carbonate, a metal oxide, a metal hydroxide, a salt of a metal acid, a heteropoly acid, a metal carboxylate, a metal carbide, a metal chloride, a metal amine complex-containing compound, a hydrate thereof, and a mixture of any two or more thereof;shaping the metal-carbon mixture to form a green shaped metal-carbon product; andheating the green shaped metal-carbon product to a carbonization temperature to produce a carbonized, shaped metal-carbon product comprising a plurality of pores.211-. (canceled)12. The process of claim 1 , wherein the metal precursor comprises a metal that is a base metal.13. The process of claim 1 , wherein the metal precursor comprises a metal selected from the group consisting of Cu claim 1 , Pb claim 1 , Ni claim 1 , Zn claim 1 , Fe claim 1 , Mo claim 1 , Al claim 1 , Sn claim 1 , W claim 1 , Ta claim 1 , Co claim 1 , Bi claim 1 , Cd claim 1 , Ti claim 1 , Zr claim 1 , Sb claim 1 , Mn claim 1 , Be claim 1 , Cr claim 1 , Ge claim 1 , V claim 1 , Ga claim 1 , Hf claim 1 , In claim 1 , Nb claim 1 , Rh claim 1 , Tl claim 1 , Ru claim 1 , Rh claim 1 , Pd claim 1 , Ag claim 1 , Os claim 1 , Ir claim 1 , Pt claim 1 , Au claim 1 , and combinations thereof.1418-. (canceled)19. The process of claim 1 , wherein the metal precursor is water insoluble.20. (canceled)21. The process of claim 1 ...

DEHYDRATION AND CRACKING OF ALPHA-, BETA-DIHYDROXY CARBONYL COMPOUNDS TO LACTIC ACID AND OTHER PRODUCTS

Processes are disclosed for the synthesis of a cracked product or an end product, from a starting compound or substrate having a carbonyl functional group (C═O), with hydroxy-substituted carbon atoms at alpha (α) and beta (β) positions, relative to the carbonyl functional group. According a particular embodiment, an α-, β-dihydroxy carboxylic acid or carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the α-hydroxy group to a second carbonyl group and removal of the β-hydroxy group. The dicarbonyl intermediate is cracked to form the cracked product, in which the first and second carbonyl groups are preserved. Either or both of (i) the cracked product and (ii) a second cracked product generated from cleavage of a carbon-carbon bond of the dicarbonyl intermediate, may be further converted (e.g., by hydrogenation) to one or more end products, which, like the cracked product(s), also having fewer carbon atoms relative to the dicarbonyl intermediate and substrate. 1. A method for synthesizing a cracked product , having a lower number of carbon atoms relative to a starting compound , the method comprising:(a) dehydrating the starting compound comprising an alpha hydroxy group, substituted at an alpha carbon atom with respect to a first carbonyl group, and a beta hydroxy group, substituted at a beta carbon atom with respect to the first carbonyl group, to form a dicarbonyl intermediate by transformation of the alpha hydroxy group to a second carbonyl group and removal of the beta hydroxy group; and(b) cracking the dicarbonyl intermediate to produce a cracked product having fewer carbon atoms relative to the dicarbonyl intermediate.2. The method of claim 1 , further comprising:(c) hydrogenating the cracked product to produce an end product, having the first carbonyl group and an adjacent hydroxy group, resulting from hydrogenation of the second carbonyl group.3. The method of claim 1 , wherein the dehydrating comprises forming water from a ...

PRE-TREATMENT OF LIGNOCELLULOSIC FEEDS FOR THE PRODUCTION OF GLYCOLS

A process for the preparing glycols from a lignocellulosic solid biomass involves contacting the biomass with an organic solvent comprising a low boiling point alcohol and a pre-treatment acid at a temperature in a range from 80 to 220° C. and a pressure in a range from 1 to 50 bara. The resulting mixture, having >20 wt. % water, is separated into a pre-treated solid residue comprising cellulose and a liquid stream comprising dissolved lignin and hemicellulose. The pre-treated solid residue is subjected to a hydrogenolysis reaction, generating a glycols stream, a lights stream, comprising a first portion of organic solvent, and a heavies stream. At least of part of the liquid stream is separated to produce a second portion of organic solvent and a solid residue of lignin and hemicellulose. At least part of the first and second portion of organic solvent is recycled to the contacting step. 2. The process of claim 1 , wherein the pre-treated solid residue comprises pre-treatment acid and the process further comprises removing pre-treatment acid from the pre-treated solid residue by washing claim 1 , drying or combinations thereof to produce an acid-removed pre-treated solid residue and recycling the removed pre-treated acid to step (a); wherein drying preferably comprises heating claim 1 , reducing pressure claim 1 , or combinations thereof.3. The process of claim 1 , wherein the pre-treated solid residue comprises lignin and the process further comprises removing the lignin from the pre-treated solid residue by washing to produce an lignin-removed pre-treated solid residue and recycling the removed pre-treated acid to step (a).4. The process according to claim 1 , wherein the pre-treatment acid further comprises at least one selected from the group consisting of hydrochloric acid claim 1 , sulfuric acid claim 1 , boric acid claim 1 , nitric acid claim 1 , phosphoric acid claim 1 , hydroxysulfonic acid claim 1 , citric acid claim 1 , benzoic acid claim 1 , α- ...

METHODS FOR PRODUCING BIODERIVED PROPYLENE GLYCOL

In the process of distilling a polyol product mixture including one or both of a biobased propylene glycol and a biobased ethylene glycol from the reaction of hydrogen with a biobased feed, it has been discovered that undesirable epoxides can form, and the present invention provides means for guarding against their formation, for removing epoxides which do form by particular methods of distilling, and for removing the epoxides from a finished, otherwise commercially acceptable biobased glycol product. 1. A process for distilling a product mixture from the reaction of hydrogen with an aqueous solution of biobased glycerol including water , lower molecular weight alcohols , higher diols and unconverted glycerol to produce a purified biobased propylene glycol product , comprising the steps of:distilling low molecular weight alcohols inclusive of methanol, ethanol and any propanols overhead in a first column;distilling substantially all of the water from the first column bottoms overhead in a second column;modifying the pH of the second column bottoms with acid, and then removing substantially all of the components therein with higher boiling points than that of propylene glycol in the bottoms from a third column; anddistilling the overheads from the third column in a fourth column to produce the distilled biobased propylene glycol product as the bottoms, with removing any glycidol and propylene oxide contained in the third column overheads as the overheads from the fourth column.2. A process according to claim 1 , further comprising distilling the third column bottoms to produce an ethylene glycol-rich diols mix overhead and a bottoms containing unreacted glycerol for recycle and reuse.3. A process for distilling a product mixture from the reaction of hydrogen with an aqueous solution of biobased glycerol including water claim 1 , lower molecular weight alcohols claim 1 , higher diols and unconverted glycerol to produce a purified biobased propylene glycol product ...

PRE-TREATMENT OF LIGNOCELLULOSIC FEEDS FOR THE PRODUCTION OF GLYCOLS

A process for preparing glycols from a lignocellulosic solid biomass involves contacting the biomass with an organic solvent comprising a low boiling point alcohol and a pre-treatment acid at a temperature in a range from 80 to 220° C. and a pressure in a range from 1 to 50 bara. The resulting mixture, having less than wt. % water, is separated into a pre-treated solid residue comprising cellulose and a liquid stream comprising dissolved lignin. The pre-treated solid residue is subjected to a hydrogenolysis reaction. generating a glycols stream, a lights stream, comprising a first portion of organic solvent, and a heavies stream. At least part of the liquid stream is separated to produce a second portion of organic solvent and a lignin stream. At least part of the first and second portions of organic solvent is recycled to the contacting step. 2. The process of claim 1 , wherein the pre-treated solid residue comprises pre-treatment acid and the process further comprises removing pre-treatment acid from the pre-treated solid residue by washing claim 1 , drying or combinations thereof to produce an acid-removed pre-treated solid residue and recycling the removed pre-treated acid to step (a); wherein drying preferably comprises heating claim 1 , reducing pressure claim 1 , or combinations thereof.3. The process of claim 1 , wherein the pre-treated solid residue comprises lignin and the process further comprises removing the lignin from the pre-treated solid residue by washing to produce an lignin-removed pre-treated solid residue and recycling the removed pre-treated acid to step (a).4. The process according to claim 1 , wherein the pre-treatment acid further comprises at least one selected from the group consisting of hydrochloric acid claim 1 , sulfuric acid claim 1 , boric acid claim 1 , nitric acid claim 1 , phosphoric acid claim 1 , hydroxysulfonic acid claim 1 , citric acid claim 1 , benzoic acid claim 1 , α-hydroxysulfonic acids claim 1 , and mixtures thereof.5. ...

SYNTHESIS OF ALIPHATIC ALCOHOLS AS AROMA CHEMICALS

The present invention relates to a method for preparing a compound of formula (I). The present invention also relates to compounds of formula (A) or a compound in the form of a stereoisomer. The present invention further relates to the use of a compound of formula (A) as aroma chemical. 3. The process according to the claim 1 , wherein steps (b) claim 1 , (c) and (d) and/or steps (b) and (c) and/or steps (c) and (d) are carried out in a single pot.4. The process according to the claim 1 , wherein the peroxyacid in step b) is selected from the group consisting of peroxymonosulfuric acid claim 1 , peroxyphosphoric acid claim 1 , peroxyacetic acid claim 1 , peroxyformic acid claim 1 , peroxytrifluoroacetic acid claim 1 , potassium peroxymonosulfate claim 1 , sodium perborate claim 1 , peroxynitric acid and peroxybenzoic acid.5. The process according to the claim 4 , wherein the peroxybenzoic acid is meta-chloroperoxybenzoic acid.6. The process according to the claim 1 , wherein the peroxide in step b) is selected from the group consisting of hydrogen peroxide.7. The process according to claim 1 , wherein step d) is carried out in the presence of an acid.8. The process according to claim 7 , wherein the acid is selected from the group consisting of methanesulfonic acid claim 7 , phosphoric acid claim 7 , p-toluenesulfonic acid claim 7 , formic acid claim 7 , sulfuric acid claim 7 , hydrochloric acid and acetic acid.10. The compound of claim 9 , wherein Ris H or methyl;{'sup': 2', '5, 'Ris selected from the group consisting of H, methyl, ethyl, 1-propyl, 1-methylethyl, and cyclopropyl; Ris selected from the group consisting of methyl, ethyl, 1-propyl, 1-methylethyl, and cyclopropyl;'}{'sup': '4', 'Ris selected from the group consisting of H, ethyl, 1-propyl, 1-methylethyl, and cyclopropyl;'}{'sup': '3', 'and Ris H.'}12. A composition comprising at least one compound selected from the the mixture of compounds of the formulae (A.a) claim 9 , (A.b) and (A.c) according to . ...

Catalyst for polyol hydrogenolysis

Ethylene glycol and propylene glycol may be made by hydrogenolysis of a polyol comprising the steps of reacting a polyol with hydrogen in the presence of a hydrogenolysis catalyst. The hydrogenolysis comprises nickel, one or more promoter, and one or more support. The promoter is selected from bismuth, silver, tin, antimony, gold, lead, thallium, cerium, lanthanum, and manganese. The support is selected from zirconia and carbon. A zirconia support comprises a zirconia textual promoter, which is selected from Cr, Mo, W, Nb, Ce, Ca, Mg, La, Pr, Nd, Al, and P. If the support comprises carbon, then the promoter is selected from bismuth and antimony. In another embodiment, if the support comprises carbon, then both the promoter is selected from bismuth and antimony, and the catalyst comprises copper. In another embodiment, the catalyst additionally comprises copper.

Process for the Manufacture of Propanediol

A process for manufacturing 1,3-propanediol by reacting glycerol with hydrogen in the presence of a supported catalyst, the supported catalyst comprising at least one first compound of an element selected from iridium, rhodium, palladium and platinum and at least one second compound of an element selected from chromium, molybdenum and tungsten, both compounds being supported on alumina, wherein the at least one second compound content in the catalyst expressed in weight of trioxide per weight of catalyst is lower than 20% by weight and wherein the reaction is carried out in a liquid medium containing water in an amount of at least 3 g and less than 900 g of water per kg of liquid medium. 1. A process for manufacturing 1 ,3-propanediol by reacting glycerol with hydrogen in the presence of a supported catalyst , the supported catalyst comprising at least one first compound of an element selected from the group consisting of iridium , rhodium , palladium and platinum and at least one second compound of an element selected from the group consisting of chromium , molybdenum and tungsten , both said compounds being supported on alumina , wherein the at least one second compound content in the catalyst expressed in weight of trioxide per weight of catalyst is lower than 20% by weight and wherein the reaction is carried out in a liquid medium containing water in an amount of at least 3 g and less than 900 g of water per kg of liquid medium.2. The process according to claim 1 , wherein the liquid medium contains at most 600 g of water per kg of liquid medium.3. The process according to claim 1 , wherein the at least one second compound content in the catalyst expressed in weight of trioxide per weight of catalyst is lower than or equal to 15% by weight.4. The process according to claim 1 , wherein the alumina in the supported catalyst is selected from the group consisting of gamma alumina claim 1 , delta alumina claim 1 , theta alumina claim 1 , and any mixture thereof.5. ...

CATALYSTS FOR HYDRODEOXYGENATION OF OXYGENATED HYDROCARBONS

The present invention provides catalysts, methods, and reactor systems for converting oxygenated hydrocarbons to oxygenated compounds. The invention includes methods for producing cyclic ethers, monooxygenates, dioxygenates, ketones, aldehydes, carboxylic acids, and alcohols from oxygenated hydrocarbons, such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like, using catalysts containing Group VIII metals. The oxygenated compounds produced are useful in the production of liquid fuels, chemicals, and other products. 143-. (canceled)44. A heterogeneous catalyst , the heterogeneous catalyst comprising (i) a Group VIII metal , (ii) a second metal , and (ii) a metal oxide support ,wherein the heterogeneous catalyst is configured to produce a mixture of reaction products, the mixture comprising alcohols having a concentration greater than about 1% as a weight percentage of the total carbon entering the system and cyclic ethers having a concentration greater than about 1% as a weight percentage of the total carbon entering the system, when an aqueous oxygenated hydrocarbon feedstock solution, the aqueous feedstock solution comprising water and an oxygenated hydrocarbon selected from the group consisting of a starch, a sugar, a sugar alcohol, a polysaccharide, an oligosaccharide, a trisaccharide, a disaccharide, a monosaccharide, and combinations thereof, and hydrogen are contacted with the heterogeneous catalyst; andwherein the metal oxide support is stable in the aqueous oxygenated hydrocarbon feedstock solution; andwherein the heterogeneous catalyst is capable of being in operation for greater than 20 days without a regeneration of the catalyst.45. The heterogeneous catalyst of claim 44 , wherein the Group VIII metal is palladium.46. The heterogeneous catalyst of claim 44 , wherein the heterogeneous catalyst comprises between 0.05 and 5.0 wt % palladium.47. The heterogeneous catalyst of claim 44 , wherein the second metal is a member ...

Processes for Converting Biomass-Derived Feedstocks to Chemicals and Liquid Fuels

The present invention provides processes, methods, and systems for converting biomass-derived feedstocks to liquid fuels and chemicals. The method generally includes the reaction of a hydrolysate from a biomass deconstruction process with hydrogen and a catalyst to produce a reaction product comprising one of more oxygenated compounds. The process also includes reacting the reaction product with a condensation catalyst to produce Ccompounds useful as fuels and chemicals. 1. A method for producing oxygenated compounds from a biomass-derived feedstock , the method comprising: (i) water;', '(ii) greater than 20 wt % of a plurality of first oxygenated hydrocarbons, the first oxygenated hydrocarbons selected from the group consisting of monosaccharides, disaccharides, trisaccharides, oligosaccharides, and combinations thereof;', '(iii) between 1 wt % and 40 wt % of a plurality of second oxygenated hydrocarbons, the second oxygenated hydrocarbon comprising sugar degradation products; and', '(iv) ash, wherein the ash comprises less than 75 ppm sulfur and less than 30 ppm phosphorous; and, '(a) providing an aqueous feedstock, the aqueous feedstock comprising(b) reacting a portion of the aqueous feedstock with hydrogen in the presence of a catalyst, the catalyst comprising at least one Group VIII metal, to produce a reaction product comprising one or more oxygenated compounds selected from the group consisting of an alcohol, a ketone, a cyclic ether, a carboxylic acid, an aldehyde, a diol, and a polyol.2. The method of claim 1 , wherein the aqueous feedstock is prepared by a biomass deconstruction method and the deconstruction method is selected from the group consisting of water hydrolysis claim 1 , acid hydrolysis claim 1 , alkaline hydrolysis claim 1 , organosolv pulping claim 1 , pyrolysis claim 1 , enzymatic hydrolysis claim 1 , catalytic biomass deconstruction claim 1 , and combinations thereof.3. The method of claim 2 , wherein the aqueous feedstock is further ...

PRODUCTION OF AROMATICS FROM DI- AND POLYOXYGENATES

Methods, catalysts, and reactor systems for producing in high yield aromatic chemicals and liquid fuels from a mixture of oxygenates comprising di- and polyoxygenates are disclosed. Also disclosed are methods, catalysts, and reactor systems for producing aromatic chemicals and liquid fuels from oxygenated hydrocarbons such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like; and methods, catalysts, and reactor systems for producing the mixture of oxygenates from oxygenated hydrocarbons such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like. The disclosed catalysts for preparing the mixture of oxygenates comprise a NiSnalloy and a crystalline alumina support. 1. A catalyst composition , the catalyst comprising a NiSnalloy and a crystalline alumina support.2. The catalyst of claim 1 , wherein n equals 3 and m equals 1 or 2.3. The catalyst of claim 1 , wherein the wt % of Ni is greater than or equal to 0.5 wt %.4. The catalyst of claim 3 , wherein the wt % of Ni is greater than or equal to 1.0 wt % or greater than or equal to 2.0%.5. The catalyst of claim 1 , wherein the wt % of Ni is less than or equal to 20%.6. The catalyst of claim 5 , wherein the wt % of Ni is less than or equal to 15% less than or equal to 12 wt % claim 5 , or less than or equal to 10 wt %.7. The composition of claim 1 , wherein the crystalline support is a transitional alumina support.8. The composition of claim 1 , wherein the crystalline support is a theta-alumina support.9. The catalyst of claim 1 , wherein the support is modified with a member selected from the group consisting of B claim 1 , Cr claim 1 , Ce claim 1 , Co claim 1 , Cu claim 1 , Fe claim 1 , Mg claim 1 , Mo claim 1 , Nb claim 1 , W claim 1 , Zr claim 1 , and mixtures thereof.10. A composition of matter claim 1 , the composition of matter comprising the catalyst of claim 1 , oxygenated hydrocarbons claim 1 , and a mixture of oxygenates.11. The composition of matter ...

METHOD FOR PRODUCING POLYALKYLENE GLYCOL DERIVATIVE HAVING AMINO GROUP AT END, WITH NARROW MOLECULAR WEIGHT DISTRIBUTION

A method for producing a narrow molecular weight distribution polyalkylene glycol derivative having an amino group at an end under mild conditions. A method for producing a compound of the general formula (1): CHO(CHCHO)CHCHCHNH(wherein n is an integer of 1 to 450) comprises the following steps of: 1. A method for producing a narrow molecular weight distribution polyethylene glycol derivative having an amino group at an end represented by a general formula (1) comprising the steps of:{'br': None, 'sub': 3', '2', '2', 'n', '2', '2', '2', '2, 'CHO(CHCHO)CHCHCHNH\u2003\u2003(1)'}wherein n represents an integer of 1 to 450;{'sup': +', '−', '−', '+, 'claim-text': [{'br': None, 'sub': 3', '2', '2', 'k, 'CHO(CHCHO)H\u2003\u2003(2)'}, {'br': None, 'sub': 3', '2', '2', 'k-1', '2', '2, 'sup': −', '+, 'CHO(CHCHO)CHCHOM\u2003\u2003(3)'}, 'wherein k represents an integer of 2 to 5;'}, 'wherein k is the same as defined in the general formula (2); and', 'M is the same as defined for the alkali metal compound;, '1) a step of reacting a compound represented by the general formula (2) with an alkali metal compound selected from M, MH, and ROM (wherein M represents sodium (Na) or potassium (K), and R represents a monovalent alkyl group having 1 to 6 carbon atoms) to obtain a compound represented by a general formula (3) [{'br': None, 'sub': 3', '2', '2', 'n-1', '2', '2, 'sup': −', '+, 'CHO(CHCHO)CHCHOM\u2003\u2003(4)'}, 'wherein n is the same as defined in the general formula (1);, '2) a step of dissolving a compound represented by the general formula (3) in tetrahydrofuran and then reacting with ethylene oxide to obtain a compound represented by the general formula (4) {'br': None, 'sub': 3', '2', '2', 'n', '2', '2, 'CHO(CHCHO)CHCHCN\u2003\u2003(5)'}, '3) a step of reacting the compound represented by the general formula (4) with acrylonitrile without further step of purifying the compound represented by the general formula (4) and then with an acid compound to obtain a compound ...

PROCESS FOR FUNCTIONALIZING BIOMASS USING MOLYBDENUM CATALYSTS

The present invention concerns a process for converting biomass into useful organic building blocks for the chemical industry. The process involves the use of molybdenum catalysts of the formula Aa(MoXRRRe), which may be readily prepared from industrial molybdenum compounds. 215-. (canceled)16. The process according to claim 1 , wherein the temperature is in the range 175 to 250° C. claim 1 , 180 to 220° C. claim 1 , 190 to 210° C. claim 1 , or 195 to 205° C.17. The process according to claim 1 , wherein the polyol is a diol or a triol.18. The process according to claim 17 , wherein the polyol is selected from the group consisting of 1 claim 17 ,2-hexanediol claim 17 , 1 claim 17 ,2-tetradecanediol claim 17 , and glycerol.19. The process according to claim 18 , wherein the polyol is glycerol.20. The process according to claim 1 , wherein the substrate is the polyol itself claim 1 , H claim 1 , or a diol different from the polyol.21. The process according to claim 20 , wherein the substrate is a diol different from the polyol.22. The process according to claim 1 , wherein the amount of molybdenum catalyst is in the range 0.1 to 2.0 mol % claim 1 , 1 to 15 mol % claim 1 , 2. to 10 mol % claim 1 , 3 to 8 mol % claim 1 , or 4 to 7 mol %.23. The process according to claim 1 , wherein A is Na or NH.24. The process according to claim 1 , wherein Rhas one or more donor atoms selected from the group consisting of N claim 1 , P claim 1 , and S.25. The process according to claim 24 , wherein Ris 2 claim 24 ,2′-bipyridine.26. The process according to claim 1 , wherein V is 1 or 7.27. The process according to claim 1 , wherein a is 0 claim 1 , 2 claim 1 , or 6.28. The process according to claim 1 , wherein the molybdenum catalyst is selected from the group consisting of Mo(CO) claim 1 , Mo(CO)(bipy) claim 1 , MoOCl(bipy) claim 1 , MoOBr(bipy) claim 1 , MoO(CH)(bipy) claim 1 , (NH)MoO·4HO claim 1 , and NaMoO claim 1 , or mixtures thereof claim 1 , wherein bipy is 2 claim 1 ,2′- ...

RENEWABLE ISOBUTENE AND ISOPRENE FROM A MIXTURE OF ACETIC ACID AND PROPIONIC ACID

A process is described for making renewable isobutene and renewable isoprene, comprising converting a mixed acid feed including acetic acid and propionic acid to a product mixture including isobutene and at least one or both of 2-methyl-1-butene and 2-methyl-2-butene in the presence of a catalyst, separating isobutene from the product mixture and dehydrogenating either or both of the 2-methyl-1-butene and 2-methyl-2-butene in the remainder to provide isoprene. 1. A process for making renewable isobutene and renewable isoprene , comprising converting a mixed acid feed including acetic acid and propionic acid to a product mixture including isobutene and at least one or both of 2-methyl-1-butene and 2-methyl-2-butene in the presence of a catalyst , separating isobutene from the product mixture and dehydrogenating either or both of the 2-methyl-1-butene and 2-methyl-2-butene in the remainder to provide isoprene.2. A process according to claim 1 , wherein the catalyst for converting the mixed acid feed is a ZnZrOmixed oxide catalyst.3. A process according to claim 2 , wherein the ZnZrOmixed oxide catalyst contains less than about 0.14 percent by weight of sulfur.4. A process according to claim 3 , wherein the ZnZrOmixed oxide catalyst contains less than about 0.01 percent by weight of sulfur.5. A process according to claim 3 , wherein the ZnZrOmixed oxide catalyst contains less than about 0.001 percent by weight of sulfur.65. A process according to any of - claims 2 , wherein x:y is from about 1:100 to about 10:1.7. A process according to claim 6 , wherein x:y is from about 1:30 to about 1:1.8. A process according to claim 7 , wherein x:y is from about 1:20 to about 1:5.9. A process according to claim 8 , wherein x:y is from about 1:12 to about 1:10.10. A process according to claim 1 , wherein the mixed acid feed is or is obtained from a mixed acid fermentation broth from a fermentation of one or more of the five carbon sugars claim 1 , six carbon sugars claim 1 , lactic ...

PROCESS FOR MANUFACTURING ACRYLIC ACID, ACRYLONITRILE AND 1,4-BUTANEDIOL FROM 1,3-PROPANEDIOL

The present invention is in the field of producing bio-based commodity organic chemicals such as bio-acrylic acid, bio-acrylonitrile, and bio-1,4-butanediol using renewable carbon sources as feedstock. In the first stage of the present invention, bio-1,3-propanediol is derived from renewable carbon sources through microbial fermentation. In the second stage of the present invention, bio-1,3-propanediol is converted into bio-acrylic acid or bio-acrylonitrile or bio-1,4-butanediol. 1. (canceled)2. (canceled)3. (canceled)4. (canceled)5. (canceled)6. (canceled)7. (canceled)8. (canceled)9. (canceled)10. (canceled)11. (canceled)12. (canceled)13. (canceled)14. (canceled)15. (canceled)16. A process for preparing acrylic acid comprising the steps of:a. catalytic dehydration of 1,3-propanediol to yield allyl alcohol; andb. catalytic oxidation of said allyl alcohol to yield acrylic acid.17. A process for preparing acrylic acid as in claim 16 , wherein the 1 claim 16 ,3-propanediol is bio-based and is obtained from biomass through a fermentative process.18. A process for preparing acrylic acid as in claim 16 , wherein said 1 claim 16 ,3-propanediol is obtained from biomass through a fermentative process and said step (b) for catalytic oxidation of said allyl alcohol to yield acrylic acid is carried out in a conventional acrylic acid manufacturing plant utilizing propylene derived from petroleum feedstock19. A process for preparing acrylonitrile comprising the steps of:a. catalytic dehydration of 1,3-propanediol to yield allyl alcohol;b. catalytically aminating said allyl alcohol to yield allyl amine; andc. catalytic oxidation of said allyl amine to yield acrylonitrile.20. A process for preparing acrylonitrile as in claim 19 , wherein said 1 claim 19 , 3-propanediol is bio-based and is obtained from biomass through a fermentative process.21. A process for preparing acrylonitrile comprising the steps of:a. catalytic dehydration of 1,3-propanediol to yield allyl alcohol; andb. ...

COPPER-CONTAINING MULTIMETALLIC CATALYSTS, AND METHOD FOR USING THE SAME TO MAKE BIOBASED 1,2-PROPANEDIOL

Copper-containing, multimetallic catalysts with either a zirconia or carbon support are described which have improved utility for the hydrogenolysis of a glycerol or glycerol-containing feedstock to provide a biobased 1,2-propanediol product. specially, improved carbon-supported examples of such catalysts are described for this reaction as well as for other processes wherein hydrogen is used, with methods for maintaining the activity of these catalysts. Related treatment methods in the preparation of these improved catalysts enable the use of carbons with a desired mechanical strength but which previously lacked activity, for example, for the conversion of a glycerol or glycerol-containing feed to produce 1,2-propanediol, so that copper-containing, multi-metallic catalysts may be employed for making a biobased propylene glycol using carbon supports that previously would have not been suitable. 1. A copper-containing multimetallic catalyst comprising copper and one or more additional metals selected from the group consisting of rhenium , palladium , platinum , ruthenium , manganese , and molybdenum on a zirconia or carbon support.2. The catalyst of claim 1 , further comprising zinc.3. The catalyst of claim 2 , wherein the catalyst consists essentially of copper claim 2 , rhenium and zinc on a zirconia or carbon support.4. The catalyst of claim 3 , wherein the copper is from 1 to 10 percent by weight of the catalyst claim 3 , rhenium is at least 0.25 percent by weight of the catalyst and zinc is at least 0.5 percent by weight of the catalyst.5. The catalyst of claim 4 , wherein the support is a monoclinic zirconia.6. The catalyst of claim 1 , wherein the support is a carbon support having:at least one of a) a single pellet crush strength of at least 7.4 MPa and b) a bulk crush strength such that not more than 7.0 percent of fines are observed to pass through a 40 mesh ASTM sieve upon the application of 3.5 MPa for thirty minutes to a sample of the carbon;a 5.3 percent ...

CONVERSION OF 2,3-BUTANEDIOL TO BUTADIENE

A composition comprising 2,3-butanediol is dehydrated to methyl vinyl carbinol and/or 1,3-butadiene by exposure to a catalyst comprising (a) MOwherein M is a rare earth metal, a group IIIA metal, Zr, or a combination thereof, and x and y are based upon an oxidation state of M, or (b) M(PO)where Mis a group IA, a group IIA metal, a group IIIA metal, or a combination thereof, and a and b are based upon the oxidation state of M. Embodiments of the catalyst comprising MOmay further include M, wherein Mis a rare earth metal, a group IIA metal, Zr, Al, or a combination thereof. In some embodiments, 2,3-butanediol is dehydrated to methyl vinyl carbinol and/or 1,3-butadiene by a catalyst comprising MO, and the methyl vinyl carbinol is subsequently dehydrated to 1,3-butadiene by exposure to a solid acid catalyst. 1. A method , comprising: [{'sub': x', 'y', '2', 'a', '4', 'b, 'sup': 3', '3', '3, 'contacting a feed stream comprising 2,3-butanediol with a catalyst comprising (a) MOwhere M is a rare earth metal, a group IIIA metal, Zr, or a combination thereof, and x and y have values based upon an oxidation state of M, and wherein the catalyst is not CeO, or (b) M(PO)where Mis a group IA metal, a group IIA metal, a group IIIA metal, or a combination thereof, and a and b have values based upon the oxidation state of M; and'}, 'dehydrating at least a portion of the 2,3-butanediol to form a product comprising methyl vinyl carbinol, 1,3-butadiene, or a combination thereof., 'converting 2,3-butanediol to methyl vinyl carbinol, 1,3-butadiene, or a mixture thereof by'}2. The method of claim 1 , wherein the catalyst has a methyl vinyl carbinol selectivity of at least 20% claim 1 , a 1 claim 1 ,3-butadiene selectivity of at least 20% claim 1 , or a combined 1 claim 1 ,3-butadiene and methyl vinyl carbinol selectivity of at least 20%.3. The method of claim 1 , wherein M is In claim 1 , Sc claim 1 , La claim 1 , Tm claim 1 , or a combination thereof.4. The method of claim 1 , wherein the ...

USE OF RHENIUM-CONTAINING SUPPORTED HETEROGENOUS CATALYSTS FOR THE DIRECT DEOXY-DEHYDRATED OF GLYCEROL TO ALLYL ALCOHOL

The present invention relates to the use of rhenium-containing supported heterogeneous catalysts for the deoxydehydration of glycerol to allyl alcohol, as well as to a process for the production of allyl alcohol from glycerol, in the presence of such heterogeneous catalysts. 1. A method for catalysing the deoxydehydration of glycerol to allyl alcohol , said method comprising:{'sub': 3', '2', '3, 'deoxydehydrating glycerol to allyl alcohol with an alumina-supported rhenium-oxide catalyst of formula ReO/AlO(I), wherein said reaction is carried out in heterogeneous conditions in the presence of at least one aliphatic alcohol.'}2. The method of claim 1 , wherein said at least one aliphatic alcohol is used as a solvent.3. The method of claim 1 , wherein said catalyst of formula (I) is chosen among those in which the amount of ReOranges from 5 to 15 weight % relative to the total mass of catalyst of formula (I).4. A process for the production of allyl alcohol from glycerol in the presence of a catalyst claim 1 , said process comprising only one step of deoxydehydration of glycerol claim 1 , said reaction being carried out in heterogeneous conditions claim 1 , in the presence of i) an alumina-supported rhenium-oxide catalyst of formula ReO/AlO(I) and of ii) at least one aliphatic alcohol.5. The process of claim 4 , wherein the catalyst of formula (I) is chosen among catalysts in which the amount of ReOranges from 5 to 15 weight % relative to the total amount of catalyst of formula (I).6. The process of claim 4 , wherein the aliphatic alcohol is a monohydroxylated alcohol having from 6 to 10 carbon atoms.7. The process of claim 6 , wherein the aliphatic alcohol is a monohydroxylated alcohol having from 6 to 8 carbon atoms.8. The process of claim 7 , wherein the monohydroxylated alcohol is a secondary alcohol.9. The process according to claim 8 , wherein the secondary alcohol is 2-hexanol or 3-octanol.10. The process according to claim 3 , wherein the deoxydehydration ...

PROCESS FOR THE CONVERSION OF SACCHARIDE-CONTAINING FEEDSTOCK

The invention provides a process for the catalytic conversion of a saccharide-containing feedstock in a reactor, wherein saccharide-containing feedstock is provided to the reactor as a feed stream through a feed pipe and is contacted with a catalyst system in the reactor, wherein the saccharide-containing feedstock in the feed pipe is maintained at a temperature below the degradation temperature of the saccharide contained therein and a section of the wall of the reactor at the point where the feed pipe enters the reactor is cooled to a temperature below the temperature of the bulk of the reactor and the reactor contents. 1. A process for the catalytic conversion of a saccharide-containing feedstock in a reactor , wherein saccharide-containing feedstock is provided to the reactor as a feed stream through a feed pipe and is contacted with a catalyst system in the reactor , wherein the saccharide-containing feedstock in the feed pipe is maintained at a temperature below the degradation temperature of the saccharide contained therein and a section of the wall of the reactor at the point where the feed pipe enters the reactor is cooled to a temperature below the temperature of the bulk of the reactor and the reactor contents.2. A process according to claim 1 , wherein the section of the wall of the reactor at the point where the feed pipe enters the reactor is cooled using a cooling liquid claim 1 , by air cooling claim 1 , or by using the heat to evaporate water in order to provide low pressure steam.3. A process according to claim 1 , wherein the section of the wall of the reactor at the point where the feed pipe enters the reactor is cooled by heat exchange with another stream in the process.4. A process according to claim 1 , wherein the saccharide-containing feedstock in the feed pipe is maintained at a temperature at least 10° C. below the degradation temperature of the saccharide contained therein.5. A process according to claim 1 , wherein the saccharide ...

METHOD FOR PRODUCING 1,3-BUTADIENE AND/OR 3-BUTEN-2-OL

Disclosed is a method for producing 1,3-butadiene and/or 3-buten-2-ol from 2,3-butanediol with high selectivity without using a radioactive substance. The method for producing 1,3-butadiene and/or 3-buten-2-ol comprises the step of dehydrating 2,3-butanediol in the presence of scandium oxide. The method enables the production of 1,3-butadiene and/or 3-buten-2-ol from 2,3-butanediol with high selectivity without using a radioactive substance. 1. A method for producing 1 ,3-butadiene and/or 3-buten-2-ol , said method comprising the step of dehydrating 2 ,3-butanediol in the presence of scandium oxide.2. The method according to claim 1 , wherein the reaction temperature of the step of dehydrating 2 claim 1 ,3-butanediol is not less than 270° C. and not more than 420° C.3. The method according to claim 1 , wherein the scandium oxide is one prepared by calcination at a temperature range of not less than 500° C. and not more than 1000° C.4. The method according to claim 1 , further comprising the step of dehydrating 3-buten-2-ol produced in the step of dehydrating 2 claim 1 ,3-butanediol claim 1 , in the presence of an acid catalyst to produce 1 claim 1 ,3-butadiene. This is the U.S. National Phase application of PCT International Application No. PCT/JP2014/073648, filed Sep. 8, 2014, and claims priority to Japanese Patent Application No. 2013-186946, filed Sep. 10, 2013, the disclosures of each of these applications being incorporated herein by reference in their entireties for all purposes.The present invention relates to a method for producing 1,3-butadiene and/or 3-buten-2-ol by using a biomass resource-derived substance as a raw material.1,3-Butadiene is a highly important key substance in the chemical industry that has been used as a raw material for various chemical products. Chemical products including synthetic rubbers such as styrene-butadiene rubbers, polybutadiene rubbers, and chloroprene rubbers, as well as ABS resins, adiponitrile and 1,4-butanediol have ...

Process for the manufacture of propanediol

A process for manufacturing 1,3-propanediol by reacting glycerol with hydrogen in the presence of a supported catalyst, the supported catalyst comprising at least one iridium compound and at least one rhenium compound, both compounds being supported on a zeolite, wherein the zeolite exhibits an MFI, a MEL, a BEA, a MOR, a FAU, a FER, a MWW, a CHA, a LTA, a ATO or a AEL framework type, and wherein the said zeolite is at least partially in the hydrogen form. 1. A process for manufacturing 1 ,3-propanediol by reacting glycerol with hydrogen in the presence of a supported catalyst , the supported catalyst comprising at least one iridium compound and at least one rhenium compound , both compounds being supported on a zeolite , wherein the zeolite exhibits an MFI , a MEL , a BEA , a MOR , a FAU , a FER , a MWW , a CHA , a LTA , a ATO or a AEL framework type , and wherein the said zeolite is at least partially in the hydrogen form.2. The process according to claim 1 , wherein the zeolite exhibits an MFI claim 1 , a MEL claim 1 , a BEA claim 1 , a MOR claim 1 , a FAU or a FER framework type.3. The process according to claim 2 , wherein the zeolite is an alumino-silicate selected from the group consisting of ZSM-5 claim 2 , ZSM-11 claim 2 , beta claim 2 , mordenite claim 2 , Y claim 2 , ferrierite claim 2 , and any mixture thereof.4. The process according to claim 3 , wherein the zeolite is ZSM-5.5. The process according to claim 3 , wherein the zeolite is Y.6. The process according to claim 3 , wherein the zeolite is beta.7. The process according to claim 3 , wherein the zeolite is mordenite.8. (canceled)9. The process according to claim 3 , wherein the zeolite is ferrierite.10. The process according to claim 1 , wherein the zeolite is an alumino-silicate and wherein the zeolite has a Si:Al ratio higher than or equal to 1:1 claim 1 , and lower than or equal to 200:11117-. (canceled)18. The process according to claim 1 , wherein the zeolite has an alkali metal content of ...

PROCESS FOR PRODUCING LIQUID FUEL FROM GAS STREAM COMPRISING CARBON DIOXIDE

A process for producing liquid fuel and liquid water from a gas stream comprising carbon dioxide and water vapor. The gas stream can be ambient air. In the process, carbon dioxide and water vapor are adsorbed onto an adsorbent. The gases are desorbed from the adsorbent to create a reaction mixture for forming the liquid fuel, such as methanol. Excess water vapor is condensed to form liquid water, which can be used in a variety of ways. 1. A process for producing liquid fuel and liquid water from a gas stream comprising carbon dioxide and water vapor , said process comprising the steps of:a. Contacting the gas stream with one or more adsorbent materials, whereby carbon dioxide and water vapor are adsorbed to the adsorbent;b. Desorbing carbon dioxide and water from the one or more adsorbent materials;c. Reacting carbon dioxide and water to form a liquid fuel;d. Condensing excess water from step b. to form liquid water.2. The process of claim 1 , wherein carbon dioxide and water vapor are adsorbed to one adsorbent material.3. The process of claim 1 , wherein water vapor is predominantly adsorbed to a first adsorbent material claim 1 , and carbon dioxide is predominantly adsorbed to a second adsorbent material.4. The process of claim 3 , wherein the gas stream is first contacted with the first adsorbent material claim 3 , and subsequently contacted with the second adsorbent material.5. The process of claim 4 , wherein the gas stream is substantially free of water vapor at the time of contacting the gas stream with the second adsorbent material.6. The process of claim 1 , wherein step a. comprises forcing a flow of air through a bed of adsorbent material.7. The process of claim 6 , wherein the flow of air is created by mechanical means.8. The process of claim 6 , wherein the flow of air is caused by wind.9. The process of claim 6 , wherein the flow of air is caused by movement of a vehicle.10. The process of claim 1 , wherein the gas stream comprises a flue gas of an ...

METHOD OF MAKING ALCOHOLS

A method of making one or more alcohols with a single hydroxy group, such as methanol and ethanol, the method comprising contacting a polyol and water with a basic catalyst. The polyol may be glycerol, for example. The '. catalyst may be magnesium oxide. 1. A method of making one or more alcohols with a single hydroxy group , the method comprising contacting a polyol with a basic catalyst in the presence of water , wherein the ambient pressure when the polyol is contacted with the catalyst is 5 atmospheres or lower.2. A method according to claim 1 , comprising a method of making one or both of methanol and ethanol.3. A method according to claim 1 , wherein the polyol is mixed with the water.4. A method according to claim 1 , wherein the weight of the water is greater than the weight of the polyol.5. A method according to claim 4 , wherein the weight of the polyol is from 0.001 to 0.5 times the weight of the water.6. A method according to claim 5 , wherein the weight of the polyol is from 0.1 to 0.5 times the weight of the water.7. A method according to claim 1 , wherein the ambient pressure when the polyol is contacted with the catalyst is 2 atmospheres or less.8. (canceled)9. A method according to wherein the catalyst is at a temperature of at least from 200° C. to 350° C. when contacted with the polyol.10. (canceled)11. (canceled)12. A method according to claim 9 , wherein the catalyst is at a temperature of from 300° C. to 350° C. when contacted with the polyol.13. (canceled)14. (canceled)15. A method according to claim 1 , wherein the catalyst comprises one or more oxides of one or more alkaline earth metal.16. A method according to claim 15 , wherein the catalyst comprises one or more of magnesium oxide claim 15 , calcium oxide claim 15 , strontium oxide and barium oxide.17. (canceled)18. A method according to claim 1 , wherein the polyol may comprise a polyhydroxyalkane.19. A method according to claim 18 , wherein the polyol comprises propane-1 claim 18 ,2- ...

METHOD FOR THE PRODUCTION OF GLYCOLS FROM SORBITOL

Implementations of the disclosed subject matter provide a process for producing ethylene glycol and propylene glycol from a sorbitol feed which may include contacting the sorbitol feed with hydrogen in a reactor in the presence of a solvent and a bi-functional catalyst system. The bi-functional catalyst system may include a first catalyst comprising a copper compound, a zinc compound, and an additional metal compound and a second catalyst comprising sodium carbonate. 1. A process for producing ethylene glycol and propylene glycol from a sorbitol feed comprising: 1) a first catalyst comprising a copper compound, a zinc compound, and an additional metal compound, and', '2) a second catalyst comprising sodium carbonate., 'contacting the sorbitol feed with hydrogen in a reactor in the presence of a solvent and a bi-functional catalyst system comprising2. The process of claim 1 , wherein the additional metal compound comprises at least one selected from the group consisting of: zirconium claim 1 , aluminum claim 1 , magnesium claim 1 , praseodymium claim 1 , neodymium claim 1 , promethium claim 1 , gadolinium claim 1 , yttrium claim 1 , lanthanum claim 1 , samarium claim 1 , thorium claim 1 , cerium claim 1 , europium claim 1 , terbium claim 1 , dysprosium claim 1 , holmium claim 1 , erbium claim 1 , thulium claim 1 , ytterbium claim 1 , lutetium claim 1 , titanium claim 1 , scandium claim 1 , and mixtures thereof.3. The process of claim 1 , wherein the additional metal compound comprises lanthanum.4. The process of claim 3 , wherein the first catalyst further comprises at least one metal selected from the group consisting of: zirconium claim 3 , aluminum claim 3 , magnesium claim 3 , praseodymium claim 3 , neodymium claim 3 , promethium claim 3 , gadolinium claim 3 , yttrium claim 3 , samarium claim 3 , thorium claim 3 , cerium claim 3 , europium claim 3 , terbium claim 3 , dysprosium claim 3 , holmium claim 3 , erbium claim 3 , thulium claim 3 , ytterbium claim 3 , ...

METHODS, MATERIALS, AND SYSTEMS FOR CONVERTING ORGANIC ACIDS TO ALCOHOLS

Systems and methods are disclosed for synthesizing one or more simple alcohols from mixtures including organic acids, water, and a superparamagnetic catalyst exposed to fluctuating magnetic fields under ambient conditions. 1. A method for synthesizing an alcohol , the method comprising:contacting a carboxylic acid with water to form a first mixture;contacting the first mixture with a superparamagnetic catalyst to form a second mixture; andexposing the second mixture to a fluctuating magnetic field to form a third mixture thereby yielding the alcohol,wherein the method is carried out at ambient conditions.2. The method of claim 1 , wherein contacting a carboxylic acid with water comprises contacting acetic acid with water claim 1 , andwherein yielding the alcohol comprises yielding one of ethanol or methanol.3. The method of claim 1 , wherein contacting a carboxylic acid with water comprises contacting a dicarboxylic acid with water.4. The method of claim 1 , wherein contacting a carboxylic acid with water to form a first mixture comprises contacting a carboxylic acid with water to form a first mixture having a molar ratio of water to the carboxylic acid of about 1.5:1 to about 4:1.5. The method of claim 1 , wherein yielding of the alcohol depends at least in part on the carboxylic acid and a molar ratio of water to the carboxylic acid.6. The method of claim 1 , wherein contacting the first mixture with a superparamagnetic catalyst comprises contacting the first mixture with a superparamagnetic catalyst comprising one or more of at least one ferromagnetic compound and at least one paramagnetic compound.7. The method of claim 1 , wherein exposing the second mixture to a fluctuating magnetic field comprises exposing the second mixture to a fluctuating magnetic field having a field strength of at least about 1 milliTesla.8. The method of claim 1 , wherein exposing the second mixture to a fluctuating magnetic field comprises exposing the second mixture to a fluctuating ...

Processes for converting biomass-derived feedstocks to chemicals and liquid fuels

The present invention provides processes, methods, and systems for converting biomass-derived feedstocks to liquid fuels and chemicals. The method generally includes the reaction of a hydrolysate from a biomass deconstruction process with hydrogen and a catalyst to produce a reaction product comprising one of more oxygenated compounds. The process also includes reacting the reaction product with a condensation catalyst to produce C 4+ compounds useful as fuels and chemicals.

Process for Producing Dienes

The present invention relates to a process for producing a diene, preferably a conjugated diene, more preferably 1,3-butadiene, comprising the dehydration of at least one alkenol having a number of carbon atoms greater than or equal to 4, in the presence of a catalytic material comprising at least one crystalline metalosilicate in acid form, preferably a macroporous zeolite, more preferably a zeolite with a FAU, BEA or MTW structure. Preferably, said alkenol having a number of carbon atoms greater than or equal to 4 may be obbtained directly through biosynthetic processes, or through catalytic dehydration processes of at least one diol. When said alkenol is a butenol, said diol is preferably a butanediol, more preferably 1,3-butanediol, even more preferably bio-1,3-butanediol, i.e. 1,3-butanediol deriving from biosynthetic processes. When said alkenol is 1,3-butanediol, or bio-1,3-butanediol, the diene obtained with the process according to the present invention is, respectively, 1,3-butadiene, or bio-1,3-butadiene. 1. Process for producing dienes , preferably a conjugated diene , more preferably 1 ,3-butadiene , comprising the dehydration of at least one alkenol having a number of carbon atoms greater than or equal to 4 , in the presence of at least one catalytic material comprising at least one macroporous zeolite in acid , or prevalently acid , form , wherein said zeolite has a molar ratio SiO/AlOcomprised between 7 and 60 , preferably between 10 and 30.2. Process according to claim 1 , wherein said catalytic material comprises at least one inorganic binder claim 1 , selected from the group consisting of silica claim 1 , alumina claim 1 , zirconium oxide claim 1 , titanium oxide and mixtures thereof claim 1 , in quantities comprised between 5% and 80% by weight claim 1 , relative to the total weight of said catalytic material.3. (canceled)4. Process according to [any one of to ] claim 1 , wherein said macroporous zeolite is a zeolite having a FAU claim 1 , or BEA ...

METHOD FOR CHEMICAL CONVERSION OF SUGARS OR SUGAR ALCOHOLS TO GLYCOLS

Methods for chemically converting sugars or sugar alcohols into polyols/glycols, wherein the sugars or sugar alcohols are converted by means of hydrogenolysis in the presence of a catalyst comprising at least one metal and on a carbon support, wherein a nitrogen-doped carbon support is used as a catalyst support. The disclosure provides methods for chemically converting sugars or sugar alcohols into glycols which permits the preparation of glycols with higher selectivity and reduces the formation of lactic acid as a by-product. 112-. (canceled)13. A method for chemically converting sugars or sugar alcohols into polyols/glycols , comprising:converting sugars or sugar alcohols by hydrogenolysis in the presence of a catalyst comprising at least one metal and on a carbon support, andusing a nitrogen-doped carbon support as a catalyst support.14. The method of claim 13 , wherein claim 13 , in a two-stage process claim 13 , firstly a sugar is hydrogenated to give a sugar alcohol and thereafter the sugar alcohol is converted into polyols in a second step by means of hydrogenolysis.15. The method of claim 13 , including converting claim 13 , by hydrogenation/hydrogenolysis claim 13 , a C6 sugar or a C6 sugar alcohol or a C5 sugar or a C5 sugar alcohol into polyols/glycols.16. The method of claim 13 , wherein a nitrogen-doped activated carbon or nitrogen-doped carbon black is used as the catalyst support.17. The method of claim 16 , wherein a carbon support is used as catalyst claim 16 , the surface of which has been doped with nitrogen atoms by reductive methods.18. The method of claim 17 , wherein said reductive methods uses ammonia and/or nitrogen and/or hydrogen.19. The method of claim 13 , wherein nitrogen-doped carbon nanotubes are used as the catalyst support.20. The method of claim 19 , wherein the carbon nanotubes are cylindrical carbon hollow bodies having a diameter of 0.4 to 100 nm which were additionally doped with nitrogen during the production thereof.21. The ...

Synthesis of r-glucosides, sugar alcohols, reduced sugar alcohols, and furan derivatives of reduced sugar alcohols

Disclosed herein are methods for synthesizing 1,2,5,6-hexanetetrol (HTO), 1,6 hexanediol (HDO) and other reduced polyols from C5 and C6 sugar alcohols or R glycosides. The methods include contacting the sugar alcohol or R-glycoside with a copper catalyst, most desirably a Raney copper catalyst with hydrogen for a time, temperature and pressure sufficient to form reduced polyols having 2 to 3 fewer hydoxy groups than the starting material. When the starting compound is a C6 sugar alcohol such as sorbitol or R-glycoside of a C6 sugar such as methyl glucoside, the predominant product is HTO. The same catalyst can be used to further reduce the HTO to HDO.

PROCESS FOR PRODUCING 1,2-PROPANEDIOL FROM GLYCEROL

A process is described for producing biobased 1,2-propanediol, comprising reacting a glycerol-containing feed containing less than 5 weight percent of water with hydrogen in the presence of a catalyst, to partially convert glycerol in the glycerol containing feed to a crude reaction product mixture including 1,2-propanediol, removing 10 water from the crude reaction product mixture, recovering a portion but not all of the 1,2-propanediol from the crude reaction product mixture, and recycling the remainder of the 1,2-propanediol with unconverted glycerol and combining these with makeup glycerol to provide additional of the essentially anhydrous, glycerol-containing feed. 1. In a process for producing 1 ,2-propanediol by reacting a glycerol-containing feed with hydrogen in the presence of a hydrogenolysis catalyst effective for catalyzing the reaction , the improvement comprising using a glycerol-containing feed containing less than 5 weight percent of water.2. The process of claim 1 , wherein the glycerol-containing feed contains less than 3 weight percent of water.3. The process of claim 2 , wherein the glycerol-containing feed contains less than 2 weight percent of water.4. The process of claim 3 , wherein the glycerol-containing feed contains less than 1 weight percent of water.5. The process of claim 4 , wherein the glycerol-containing feed contains less than 0.5 weight percent of water.6. The process of claim 1 , wherein the glycerol-containing feed consists of a product recycle portion from the process and a makeup portion of a virgin glycerol feed.7. The process of claim 6 , wherein the glycerol-containing feed consists essentially of 1 claim 6 ,2-propanediol produced by the hydrogenolysis reaction combined with glycerol.8. The process of claim 7 , wherein the glycerol-containing feed contains less than about 1 percent by weight of anything other than 1 claim 7 ,2-propanediol claim 7 , glycerol and water.9. The process of claim 8 , wherein the glycerol- ...

RHENIUM CATALYSTS FOR GLYCERIN TO ALLYL ALCOHOL CONVERSION

A catalyst system for the conversion of glycerin to allyl alcohol, the catalyst system comprising: a rhenium compound selected from rhenium dioxide, rhenium trioxide, and a combination thereof. A method of producing allyl alcohol from glycerin via the catalyst system, the method comprising exposing glycerin to a temperature of greater than 140° C. in the presence of a catalyst comprising rhenium trioxide, rhenium dioxide, or a combination thereof to produce a product comprising allyl alcohol. 1. A method comprising:exposing glycerin to a temperature of greater than 140° C. in the presence of a catalyst comprising rhenium trioxide, rhenium dioxide, or a combination thereof to produce a product comprising allyl alcohol.2. The method of claim 1 , wherein the glycerin is exposed to the temperature of greater than 140° C. in a solvent.3. The method of claim 2 , wherein the solvent comprises a secondary alcohol.4. The method of claim 3 , wherein the secondary alcohol comprises 3-octanol.5. The method of claim 4 , wherein the product comprising allyl alcohol further comprises 3-octanone byproduct.6. The method of further comprising separating 3-octanone from the product comprising allyl alcohol claim 5 , and hydrogenating at least a portion of the separated 3-octanone to provide 3-octanol.7. The method of claim 1 , wherein the catalyst is present in the range of from 0.5 to 10 mole percent.8. The method of claim 1 , wherein the glycerin comprises bio-glycerin claim 1 , and the allyl alcohol comprises bio-allyl alcohol.9. The method of further comprising hydroformylating the allyl alcohol with synthesis gas to produce a hydroformylation product comprising 4-hydroxybutyraldehyde (HBA) and 3-hydroxy-2-methylpropionaldehyde (HMPA).10. The method of claim 9 , wherein hydroformylation is performed in anhydrous toluene claim 9 , with a rhodium catalyst in the presence of phosphine ligands.11. The method of claim 9 , wherein the hydroformylation is performed in the presence of a ...

SURFACE-MODIFIED CALCIUM CARBONATE AS CARRIER FOR TRANSITION METAL-BASED CATALYSTS

The present invention relates to a catalyst system comprising a transition metal compound on a solid carrier which is a surface-reacted calcium carbonate. The invention further relates to a method for manufacturing said catalyst system and to its use in heterogeneous catalysis. 1. A catalyst system comprising a transition metal compound on a solid carrier , wherein the solid carrier is a surface-reacted calcium carbonate comprising ground natural calcium carbonate (GNCC) or precipitated calcium carbonate (PCC) , and at least one water-insoluble calcium salt other than calcium carbonate , and wherein the surface-reacted calcium carbonate shows:{'sup': '2', '(i) a specific surface area of from 15 to 200 m/g measured using nitrogen and the BET method according to ISO 9277:2010;'}(ii) an intra-particle intruded specific pore volume in the range of from 0.1 to2. 3 cm/g calculated from mercury porosimetry measurement; and(iii) a ratio of the at least one water-insoluble calcium salt to calcite, aragonite and/or vaterite in the range of from 1:99 to 99:1 by weight.2. The catalyst system according to claim 1 , wherein the at least one water-insoluble calcium salt is selected from the group consisting of octacalcium phosphate claim 1 , hydroxylapatite claim 1 , chlorapatite claim 1 , fluorapatite claim 1 , carbonate apatite and mixtures thereof claim 1 , preferably the at least one water-insoluble calcium salt is hydroxylapatite.3. The catalyst system according to claim 1 , wherein the ratio of the at least one water-insoluble calcium salt to calcite claim 1 , aragonite and/or vaterite claim 1 , preferably to calcite claim 1 , is in the range of from 1:9 to 9:1 claim 1 , preferably from 1:7 to 8:1 claim 1 , more preferably from 1:5 to 7:1 and even more preferably from 1:4 to 7:1 by weight4. The catalyst system according to claim 1 , wherein the transition metal compound is selected from the group consisting of palladium compounds claim 1 , platinum compounds claim 1 , copper ...

PRODUCING BDO VIA HYDROFORMYLATION OF ALLYL ALCOHOL MADE FROM GLYCERIN

A method including hydroformylating, with syngas, allyl alcohol in an allyl alcohol feed, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; and producing a 1,4-butanediol (BDO) product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product. A method including hydroformylating, with syngas, allyl alcohol in a feed comprising bio-allyl alcohol, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; and producing a BDO product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product. A method including hydroformylating, with syngas, bio-allyl alcohol in a feed comprising bio-allyl alcohol, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; producing a BDO product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product; and removing a byproduct of the production of the bio-allyl alcohol prior to hydroformylating the bio-allyl alcohol and/or from the BDO-product. 1. A method comprising:hydroformylating, with synthesis gas, allyl alcohol in a feed comprising allyl alcohol derived from glycerin, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde (HBA) and 3-hydroxy-2-methylpropionaldehyde (HMPA); andproducing a 1,4-butanediol (BDO) product comprising BDO and 1,3-methylpropanediol (MPD) via hydrogenation of at least a portion of the hydroformylation product.2. The method of claim 1 , wherein the feed comprises bio-allyl alcohol derived from bio-based glycerin claim 1 , non-bio-allyl alcohol derived from non-bio-based glycerin claim 1 , or a combination thereof.3. The method of claim 1 , wherein the feed comprising allyl alcohol further comprises acrolein claim 1 , lactic acid claim 1 , octene isomers claim 1 , ...

PROCESS FOR THE PREPARATION OF A HYDROGENATION CATALYST AND ITS USE FOR THE PREPARATION OF GLYCOLS

A process for the preparation of an unsupported hydrogenation catalyst wherein a catalyst precursor comprising one or more cations selected from a group consisting of chromium and groups 8, 9, 10 and 11 of the periodic table is contacted in a reactor with hydrazine to convert the catalyst precursor into the unsupported hydrogenation catalyst. 1. A process for the preparation of an unsupported hydrogenation catalyst , wherein a catalyst precursor comprising one or more cations selected from a group consisting of chromium and groups 8 , 9 , 10 and 11 of the periodic table is contacted with hydrazine in a reactor to convert the catalyst precursor into an unsupported hydrogenation catalyst.2. The process according to claim 1 , wherein the one or more cations is selected from a group consisting of chromium claim 1 , iron claim 1 , ruthenium claim 1 , cobalt claim 1 , rhodium claim 1 , iridium claim 1 , nickel claim 1 , copper claim 1 , palladium and platinum.3. The process according to claim 1 , wherein the catalyst precursor comprises an anion selected from a group consisting of carboxylates claim 1 , acetylacetonate and inorganic anions claim 1 , which in all cases form a salt or a metal complex that is soluble in a solvent mixture comprising the saccharide-containing feedstock claim 1 , the solvent and the glycols.4. The process according to claim 1 , wherein the catalyst precursor comprises formate or acetate.5. The process according to claim 1 , wherein the catalyst precursor comprises ruthenium cations.6. A process for the preparation of glycols from a saccharide-containing feedstock comprising the steps of:(a) preparing an unsupported hydrogenation catalyst by contacting a catalyst precursor comprising one or more cations selected from a group consisting of chromium and of groups 8, 9, 10 and 11 of the periodic table with hydrazine in a reactor to convert the catalyst precursor into the unsupported hydrogenation catalyst;(b) preparing in a reactor vessel a ...

PROCESS FOR PRODUCTION OF ALLYL ALCOHOL

The invention relates to a process for producing allyl alcohol, the process comprising: 1. A process for producing allyl alcohol , the process comprising: 'wherein the dehydration is performed in the presence of a basic catalyst.', 'dehydrating a C3-oxygenate comprising monopropylene glycol or 1,3-propanediol;'}2. The process of claim 1 , wherein the C3-oxygenate is diluted with water claim 1 , preferably at a concentration of greater than 10 claim 1 , 20 claim 1 , 30 claim 1 , 40 or 50% and at a concentration of less than 100 claim 1 , 90 claim 1 , 80 claim 1 , 70 claim 1 , 60 or 50%.3. The process of claim 1 , wherein the basic catalyst comprises an element with an electronegativity of less than 2.0 claim 1 , more preferably less than 1.5 and most preferably less than 1.0 claim 1 , according to the Allred-Rochow scale of electronegativity.4. The process of claim 3 , wherein the element is from Group 1 and/or Group 2 claim 3 , preferably in the form of a metal oxide claim 3 , hydroxide or mixture thereof claim 3 , more preferably KOH.5. The process of claim 3 , wherein the basic element is carried on a support selected from the group consisting of SiO claim 3 , AlO claim 3 , ZrO claim 3 , TiO claim 3 , ZnO and CeO—ZrOand mixture thereof claim 3 , or on a carbon support.6. The process of claim 5 , wherein the catalyst is KOH/ZrO.7. The process of claim 1 , wherein the dehydration is conducted at a WHSV of ≥0.1 g/g/h and ≤10 g/g/h claim 1 , preferably ≥0.3 g/g/h claim 1 , and more preferably ≥1 g/g/h.8. The process of claim 1 , wherein the dehydrated C3-oxygenate comprising allyl alcohol is converted by oxidation into acrylic acid claim 1 , preferably in an oxidation reactor.9. The process of claim 8 , wherein the dehydrated C3-oxygenate is obtained as a fraction of dehydration effluent claim 8 , which fraction also comprises water claim 8 , and said fraction is fed to an oxidation reactor for converting the dehydrated C3-oxygenate into acrylic acid.10. The process ...

PROCESS FOR THE PREPARATION OF GLYCOLS

The invention provides a process for the production of glycols comprising the step of adding to a reactor vessel a saccharide-containing feedstock, a solvent, hydrogen, a retro-aldol catalyst composition and a catalyst precursor and maintaining the reactor vessel at a temperature and a pressure, wherein the catalyst precursor comprises one or more cations selected from groups 8, 9, 10 and 11 of the periodic table, and wherein the catalyst precursor is reduced in the presence of hydrogen in the reactor vessel into an unsupported hydrogenation catalyst. 1. A process for the production of glycols comprising the step of adding to a reactor vessel a saccharide-containing feedstock , a solvent , hydrogen , a retro-aldol catalyst composition and a catalyst precursor and maintaining the reactor vessel at a temperature and a pressure , wherein the catalyst precursor comprises one or more cations selected from groups 8 , 9 , 10 and 11 of the periodic table , and wherein the catalyst precursor is reduced in the presence of hydrogen in the reactor vessel into an unsupported hydrogenation catalyst.2. The process claimed in claim 1 , wherein the glycols comprise ethylene glycol and 1 claim 1 , 2-propylene glycol.3. The process claimed in claim 1 , wherein the saccharide-containing feedstock comprises one or more saccharide selected from the group consisting of monosaccharides claim 1 , disaccharides claim 1 , oligosaccharides and polysaccharides.4. The process claimed in claim 1 , wherein the solvent is water claim 1 , or a C1 claim 1 , C2 claim 1 , C3 claim 1 , C4 claim 1 , C5 or a C6 alcohol or polyalcohol claim 1 , or any combination of mixtures thereof.5. The process claimed in claim 1 , wherein the cation is selected from a group consisting of iron claim 1 , ruthenium claim 1 , cobalt claim 1 , rhodium claim 1 , nickel claim 1 , palladium and platinum.6. The process claimed in claim 1 , wherein the cation is selected from a group consisting of ruthenium claim 1 , nickel ...

PROCESS FOR THE PREPARATION OF GLYCOLS

A process for the preparation of glycols from a saccharide-containing feedstock having the steps of: (a) preparing a reaction mixture in a reactor vessel comprising the saccharide-containing feedstock, a solvent, hydrogen, a catalyst component with retro-aldol catalytic capabilities and a first hydrogenation catalyst comprising an element selected from groups 8, 9 and 10 of the periodic table; (b) monitoring the hydrogenation activity in the reactor vessel; (c) when the activity of the first hydrogenation catalyst declines, as indicated by the crossing of a threshold, supplying into the reaction mixture in the reactor vessel a catalyst precursor comprising one or more elements selected from groups 8, 9, 10 and 11 of the periodic table; and (d) converting the catalyst precursor in the presence of hydrogen in the reactor vessel to a second hydrogenation catalyst to supplement the declined hydrogenation activity in the reactor vessel. 1. A process for the preparation of glycols from a saccharide-containing feedstock comprising the steps of:(a) preparing a reaction mixture in a reactor vessel comprising the saccharide-containing feedstock, a solvent, a catalyst component with retro-aldol catalytic capabilities and a first hydrogenation catalyst comprising an element selected from groups 8, 9 and 10 of the periodic table;(b) supplying hydrogen gas into the reaction mixture in the reactor vessel;(c) monitoring the hydrogenation activity in the reactor vessel;(d) when the hydrogenation activity declines, supplying into the reaction mixture in the reactor vessel a catalyst precursor comprising one or more elements selected from groups 8, 9, 10 and 11 of the periodic table; and(e) converting the catalyst precursor in the presence of hydrogen in the reactor vessel to a second hydrogenation catalyst to supplement the declined hydrogenation activity in the reactor vessel.2. The process according to wherein the catalyst precursor comprises one or more cations selected from a ...

METHODS OF CONVERTING POLYOLS

Methods for converting polyols are provided. The methods provided can include using a metal pincer catalyst (e.g., an iridium pincer catalyst) to remove at least one alcohol group from a polyol. The methods provided can include converting glycerol to 1,3-propanediol. 2. The method of claim 1 , wherein the polyol comprises a linear or cyclic C-Calkane molecule substituted with the at least two alcohol groups.3. The method of claim 1 , wherein the acid comprises a homogeneous or heterogeneous proton donor.4. The method of claim 1 , wherein the acid is selected from the group consisting of sulfuric acid claim 1 , tungstic acid claim 1 , phosphoric acid claim 1 , hydrochloric acid and trifluoromethanesulfonic acid.5. The method of claim 3 , wherein the homogeneous acid is used at a concentration range of about 0.03M to about 0.1M.6. The method of claim 1 , wherein the organic solvent includes dioxane claim 1 , sulfolane claim 1 , 1 claim 1 ,3-dimethyl-2-imidazolidinone claim 1 , 1-methyl-2-pyrrolidone claim 1 , 1-methyl-2-piperidone claim 1 , and/or bis(2-methoxyethyl)ether.7. The method of claim 1 , wherein M claim 1 , Mand Mare each independently selected from iridium or rhodium.8. (canceled)9. The method of claim 1 , wherein Xand Xare O.10. The method of claim 1 , wherein Xis C.11. The method of claim 1 , wherein R claim 1 , R claim 1 , Rand Rare the same.12. The method of claim 1 , wherein R claim 1 , R claim 1 , Rand Rare the same.13. The method of claim 1 , wherein R claim 1 , R claim 1 , Rand Rare the same.14. The method of claim 1 , wherein R claim 1 , R claim 1 , R claim 1 , and Rare the same.15. The method of claim 1 , wherein at least one of R claim 1 , Ror Rcomprises a linking group.16. The method of claim 1 , wherein at least one of R claim 1 , R claim 1 , R claim 1 , R claim 1 , or Rcomprises a linking group.17. The method of claim 1 , wherein at least one of R claim 1 , R claim 1 , R claim 1 , R claim 1 , Ror Rcomprises a linking group.18. The method of ...

Hydrogenolysis catalysts and uses thereof

A hydrogenation catalyst comprising nickel, rhenium, and cadmium is disclosed. Process of using hydrogenation catalyst for producing propylene glycol from polyol feedstock are also disclosed. The present invention relates generally to catalysts and more particularly, to catalysts having an enhanced ability to produce propylene glycol from sugar alcohols while reducing the production of by-products.

SYNTHESIS OF BICYCLO[2.2.2]OCTANE DERIVATIVES

Provided is a process for the preparation of certain 1,4-bicyclo[2.2.2]octane derivatives. The new synthetic procedure involves treating 1,4-dimethylene cyclohexane with an oxidizing agent in the presence of a transition metal catalyst to afford an oxo-substituted bicyclo[2.2.2]octane species. This intermediate structure can then be further derivatized. The processes of this disclosure thus affords a novel and simplified means for the commercial production of a wide variety of bicyclo[2.2.2]octane derivatives. 2. The process of claim 1 , represented by step (a).7. The process of claim 1 , represented by step (b).9. The process of claim 1 , represented by step (c).19. A polymer including monomers derived from compounds prepared by the process of any one of or -. This disclosure relates to the field of organic synthesis. In particular, it relates to a process for preparing a variety of 1,4-(substituted) bicyclo[2.2.2]octane derivatives.Bicyclo[2.2.2]octanes substituted at 1- and/or 4-positions are of great commercial interest. See, for example: (a) Joel G. Whitney, W. A. Gregory, J. C. Kauer, J. R. Roland, Jack A. Snyder, R. E. Benson and E. C. Hermann “Antiviral agents. I. Bicyclo[2.2.2]octan- and -oct-2-enamines” J. Med. Chem., 1970, 13, 254-60; (b) U.S. Pat. No. 3,546,290. (c) “4-Pyridyl and 4-(substituted-pyridyl) bicyclo[2.2.2]octane-1-amines” U.S. Pat. No. 3,367,941; and (d) Bicyclo [2.2.2] Acid GPR120 Modulators, US Pat. Appl. 2016/0039780.Unfortunately, the bridgehead substituents of various bicyclic systems inclusive of the bicyclo[2.2.2]octane system are inert to nucleophilic substitution. Therefore, it would be useful to develop simple methods of preparation of the bridgehead bicyclo[2.2.2]octane derivatives. 1,4-Diacetoxybicyclo[2.2.2]octane is particularly interesting because it is a potential starting material for the preparation of various bridgehead bicyclo[2.2.2]octane derivatives. By way of example, U.S. Pat. No. 6,649,660 teaches various adenosine ...

PROCESS FOR THE PREPARATION OF GLYCOLS

A process for the preparation of glycols from a saccharide-containing feedstock comprising the steps of: (a) preparing a reaction mixture in a reactor vessel comprising the saccharide-containing feedstock, a solvent, a catalyst component with retro-aldol catalytic capabilities and a first hydrogenation catalyst comprising an element selected from groups 8, 9 and 10 of the periodic table; (b) supplying hydrogen gas to the reaction mixture in the reactor vessel; (c) monitoring the activity of the first hydrogenation catalyst; (d) preparing a second hydrogenation catalyst by contacting in a reactor a catalyst precursor comprising one or more elements selected from chromium and groups 8, 9, 10 and 11 of the periodic table with hydrazine to convert the catalyst precursor into the second hydrogenation catalyst; (e) when the hydrogenation activity declines, supplying the second hydrogenation catalyst to the reactor vessel to supplement the declined hydrogenation activity in the reactor vessel. 1. A process for the preparation of glycols from a saccharide-containing feedstock comprising the steps of:(a) preparing a reaction mixture in a reactor vessel comprising the saccharide-containing feedstock, a solvent, a catalyst component with retro-aldol catalytic capabilities and a first hydrogenation catalyst comprising an element selected from groups 8, 9 and 10 of the periodic table;(b) supplying hydrogen gas to the reaction mixture in the reactor vessel;(c) monitoring the hydrogenation activity in the reactor vessel;(d) preparing a second hydrogenation catalyst by contacting in a reactor a catalyst precursor comprising one or more elements selected from chromium and groups 8, 9, 10 and 11 of the periodic table with hydrazine to convert the catalyst precursor into the second hydrogenation catalyst; and(e) when the hydrogenation activity declines, supplying the second hydrogenation catalyst to the reactor vessel to supplement the declined hydrogenation activity in the reactor ...

Processes for converting biomass-derived feedstocks to chemicals and liquid fuels

The present invention provides processes, methods, and systems for converting biomass-derived feedstocks to liquid fuels and chemicals. The method generally includes the reaction of a hydrolysate from a biomass deconstruction process with hydrogen and a catalyst to produce a reaction product comprising one of more oxygenated compounds. The process also includes reacting the reaction product with a condensation catalyst to produce C 4+ compounds useful as fuels and chemicals.

PROCESS FOR PRODUCTION OF HEXANETRIOL FROM 5-HYDROXYMETHYLFURFURAL

Industrial scale conversions of 5-hydroxymethylfurfural to commodity chemicals such as 1,2,6-hexanetriol and 1,6-hexanediol by chemocatalytic conversions using hydrogen and a heterogeneous reduction catalyst are provided. The reactions are suitable for use in continuous flow reactors. Methods of carrying out the conversions are provided, as are product and catalyst compositions. 125-. (canceled)26: A process for preparing 2 ,5-bis-hydroxymethylfuran (BHMF) from 5-hydroxymethylfurfural (HMF) comprising:reacting the 5-hydroxymethylfurfural (HMF) with hydrogen in a continuous flow reactor in the presence of an organic solvent and a heterogeneous reduction catalyst comprising Cu to form the 2,5-bis-hydroxymethylfuran (BHMF) over an on-stream period of at least 150 hours.27: A process for preparing 2 ,5-bis-hydroxymethylfuran (BHMF) from 5-hydroxymethylfurfural (HMF) comprising:reacting the 5-hydroxymethylfurfural (HMF) with hydrogen in a continuous flow reactor in the presence of an organic solvent and a heterogeneous reduction catalyst comprising Pt to form the 2,5-bis-hydroxymethylfuran (BHMF) over an on-stream period of at least 150 hours.28: The process of claim 26 , wherein the heterogeneous reduction catalyst further comprises a modifier.29: The process of claim 28 , wherein the modifier is selected from the group consisting of Mn claim 28 , Co claim 28 , Au claim 28 , W claim 28 , Cu claim 28 , Zn claim 28 , Mo claim 28 , Sb claim 28 , Bi and Pb.30: The process of claim 26 , wherein the heterogeneous reduction catalyst comprises a combination of metals selected from the group consisting of Co—Cu and Ni—Cu.31: The process of claim 26 , wherein the heterogeneous reduction catalyst further comprises a catalyst support.32: The process of claim 31 , wherein the catalyst support is selected from the group consisting of carbons claim 31 , aluminas claim 31 , zirconias claim 31 , silicas claim 31 , alumina-silicas claim 31 , titanias claim 31 , alumina-titanias claim 31 ...

IMPROVED PROCESSES FOR PRODUCING PROPYLENE GLYCOL

Processes for producing propylene glycol are disclosed. The processes may comprise subjecting a polyol to a hydrogenolysis reaction, thus producing propylene glycol and a product stream including an unreacted polyol and at least one unwanted compound. The process may include subjecting the product stream to a process that removes at least a portion of the at least one unwanted compound, thus producing a cleaned product stream, and subjecting the cleaned product stream to the hydrogenolysis reaction. Systems for implementing such processes are also described. 1. A process of producing propylene glycol , the process comprising:subjecting a polyol to a hydrogenolysis reaction, thus producing propylene glycol and a product stream including an unreacted polyol and at least one unwanted compound;subjecting the product stream to a process that removes at least a portion of the at least one unwanted compound, thus producing a cleaned product stream; andsubjecting the cleaned product stream to the hydrogenolysis reaction.2. The process according to claim 1 , wherein the process that removes the at least a portion of the at least one unwanted compound is a chromatographic separation.3. The process according to claim 2 , wherein the chromatographic separation is ion-exclusion.4. The process according to claim 2 , wherein the process that removes the at least a portion of the at least one unwanted compound is a C-SEP separation process.5. (canceled)6. The process according to claim 1 , wherein the at least one unwanted compound comprises a salt.7. The process according to claim 1 , wherein the product stream includes unreacted polyol claim 1 , a chain of the polyol claim 1 , and a salt.8. The process according to claim 7 , wherein the hydrogenolysis reaction converts at least a portion of the unreacted polyol to the propylene glycol and converts at least a portion of the chain of the polyol to propylene glycol.9. The process according to claim 1 , further comprising blending ...

METAL OXIDE-STABILIZED ZIRCONIUM OXIDE CERAMIC MATERIALS

The present disclosure relates generally to ceramic materials suitable for use as catalyst support materials, catalysts using such materials and methods for using them, such as methods for converting sugars, sugar alcohols, glycerol, and bio-renewable organic acids to commercially-valuable chemicals and intermediates. One aspect of the invention is a ceramic material including zirconium oxide and one or more metal oxides selected from nickel oxide, copper oxide, cobalt oxide, iron oxide and zinc oxide, the ceramic material being at least about 50 wt. % zirconium oxide. In certain embodiments, the ceramic material is substantially free of any binder or additional stabilizing agent. 1. A ceramic material comprising zirconium oxide and metal oxide , whereinthe zirconium oxide is present in an amount within the range of about 50 wt. % to about 99 wt. % of the material;the metal oxide is one or more of nickel oxide, copper oxide, cobalt oxide, iron oxide and zinc oxide; andthe metal oxide is present in an amount within the range of about 1 wt. % to about 50 wt. % of the material, calculated on metallic basis.2. The ceramic material of claim 1 , whereinthe zirconium oxide is present in an amount within the range of about 75 to about 99 wt. % of the material;the metal oxide is present in an amount within the range of about 1 wt. % to about 25 wt. % of the material, calculated on metallic basis; andwherein the ceramic material optionally includes one or more additional metal oxides present in an amount up to about 20 wt. % of the material, calculated on metallic basis.3. The ceramic material of claim 1 , substantially free of chromium.4. The ceramic material of claim 1 , substantially free of manganese.5. The ceramic material of claim 1 , substantially free of silicon oxide claim 1 , aluminum compounds claim 1 , silica-alumina compounds claim 1 , graphite and carbon black.6. The ceramic material of claim 1 , wherein the zirconium oxide is predominantly in a tetragonal phase ...

Shaped porous carbon products

Shaped porous carbon products and processes for preparing these products are provided. The shaped porous carbon products can be used, for example, as catalyst supports and adsorbents. Catalyst compositions including these shaped porous carbon products, processes of preparing the catalyst compositions, and various processes of using the shaped porous carbon products and catalyst compositions are also provided.

Process for the production of 1,3-butadiene from 1,3-butanediol

Process for the production of 1,3-butadiene comprising: feeding a mixture (a) comprising 1,3-butanediol and water to an evaporator, said water being present in an amount of greater than or equal to 5% by weight, preferably ranging from 10% by weight to 85% by weight, more preferably ranging from 15% by weight to 30% by weight, relative to the total weight of said mixture (a), to obtain: (b) a gaseous stream comprising 1,3-butanediol exiting from the top of said evaporator; and, optionally, (c) a blow-down stream exiting from the bottom of said evaporator; feeding said gaseous stream (b) to a first reactor containing at least one dehydration catalyst to obtain (d) a stream comprising alkenols, water and, optionally, impurities and/or unreacted 1,3-butanediol, exiting from said first reactor; optionally, feeding said stream (d) to a first purification section to obtain: (e) a stream comprising al-kenols, water, and, optionally, impurities; (f) a stream comprising water and, optionally, impurities and/or unreacted, 3-butanediol; and, optionally, (f) a stream comprising impurities; feeding said stream (d) or said stream (e) to a second reactor containing at least one dehydration catalyst to obtain (g) a stream comprising 1,3-butadiene, water and, optionally, impurities and/or unreacted alkenols, exiting from said second reactor; feeding said stream (g) to a second purification section to obtain: (h) a stream comprising pure 1,3-butadiene; (i) a stream comprising water and, optionally, unreacted alkenols; and, optionally, (1) a stream comprising impurities. Said 1,3-butadiene may advantageously be used as a monomer or intermediate in the production of elastomers and (co)polymers.

Glycerol conversion by heterogeneous catalysis

A method for preparing lactic acid is described, having a step of converting glycerol in the presence of a platinum-based heterogeneous catalyst on a zirconia-based support, in basic medium under inert atmosphere.

Production of Aromatics from Di- and Polyoxygenates

Methods, catalysts, and reactor systems for producing in high yield aromatic chemicals and liquid fuels from a mixture of oxygenates comprising di- and polyoxygenates are disclosed. Also disclosed are methods, catalysts, and reactor systems for producing aromatic chemicals and liquid fuels from oxygenated hydrocarbons such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like; and methods, catalysts, and reactor systems for producing the mixture of oxygenates from oxygenated hydrocarbons such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like. The disclosed catalysts for preparing the mixture of oxygenates comprise a NiSnalloy and a crystalline alumina support. 1. A method for producing oxygenated compounds from oxygenated hydrocarbons , the method comprising:{'claim-ref': {'@idref': 'CLM-00001', 'claim 1'}, 'reacting an aqueous feedstock, the aqueous feedstock comprising water and one or more oxygenated hydrocarbons selected from the group consisting of, monosaccharides, disaccharides, oligosaccharides, polysaccharides, sugar alcohols, sugar degradation products, cellulosic derivatives, hemicellulosic derivatives, lignin derivatives, lignocellulosic derivatives, and mixtures thereof, with hydrogen in the presence of the catalyst of to produce a mixture of oxygenates,'}wherein the H:Ceff ratio of the mixture of oxygenates is greater than or equal to 0.5 and less than or equal to 1.7.2. The method of claim 1 , wherein the mixture of oxygenates has one or more attributes selected from the group consisting of (i) a % CF ratio greater than or equal to 0.5 of dioxygenates and polyoxygenates to monooxygenates claim 1 , (ii) a % CF ratio greater than or equal to 0.5 of dioxygenates to monooxygenates claim 1 , (iii) a % CF ratio greater than or equal to 1.0 of C2-4 oxygenates to C5-6 oxygenates claim 1 , and (iv) the mixture of oxygenates further comprising alkanes and less than or equal to 10% CF alkanes.3. A ...

METAL OXIDE CATALYST SYSTEMS FOR CONVERSION OF ETHANOL TO BUTADIENE

A process includes reacting a feed stream containing ethanol and optionally acetaldehyde in a dehydration reactor in the presence of a dehydration catalyst system having a Group 4 or Group 5 metal oxide and a support. The process includes obtaining a product stream containing butadiene from the dehydration reactor. Another process includes reacting a feed stream containing ethanol and optionally acetaldehyde in a dehydration reactor in the presence of a dehydration catalyst system containing a tungsten oxide supported on a zeolite or a tantalum oxide supported on a zeolite. The process includes obtaining a product stream containing butadiene from the dehydration reactor. 1. A process comprising:reacting a feed stream comprising ethanol in a dehydration reactor in the presence of a dehydration catalyst system comprising a Group 4 metal oxide and a support; andobtaining a product stream comprising butadiene from the dehydration reactor.2. The process of claim 1 , wherein the feed stream further comprises acetaldehyde.3. The process of claim 1 , wherein the dehydration catalyst system contains only a single metal oxide claim 1 , wherein the single metal oxide comprises a Group 4 metal oxide.4. The process of claim 3 , wherein the dehydration catalyst system contains a Group 4 metal oxide that comprises a zirconium metal oxide.5. (canceled)6. The process of claim 1 , wherein the dehydration catalyst system comprises a bimetallic catalyst system containing only two metal oxides claim 1 , and wherein at least one of the two metal oxides comprises a Group 4 metal oxide or a Group 5 metal oxide.7. The process of claim 1 , wherein the dehydration catalyst system comprises a trimetallic catalyst system containing only three metal oxides claim 1 , and wherein at least one of the three metal oxides comprises a Group 4 metal oxide or a Group 5 metal oxide.8. The process of claim 1 , the dehydration catalyst system comprises a cobalt-zirconium oxide claim 1 , a cerium-zirconium ...

SHAPED POROUS CARBON PRODUCTS

Shaped porous carbon products and processes for preparing these products are provided. The shaped porous carbon products can be used, for example, as catalyst supports and adsorbents. Catalyst compositions including these shaped porous carbon products, processes of preparing the catalyst compositions, and various processes of using the shaped porous carbon products and catalyst compositions are also provided. 1146-. (canceled)147. A process for the selective oxidation of an aldose to an aldaric acid comprising reacting the aldose with oxygen in the presence of a catalyst composition to form the aldaric acid , wherein the catalyst composition comprises a shaped porous carbon product as a catalyst support and a catalytically active component , wherein the shaped porous carbon product comprises:(a) carbon black and{'sup': 2', '2', '3, '(b) a carbonized binder comprising a carbonization product of a water soluble organic binder and wherein the shaped porous carbon product has a BET specific surface area from about 20 m/g to about 500 m/g, a mean pore diameter greater than about 5 nm, a specific pore volume greater than about 0.1 cm/g, a carbon black content of at least about 35 wt. %, and a carbonized binder content from about 20 wt. % to about 50 wt. %.'}148160-. (canceled)161. The process of claim 147 , wherein the aldose comprises a pentose and/or a hexose.162. The process of claim 161 , wherein the pentose comprises ribose claim 161 , arabinose claim 161 , xylose claim 161 , and/or lyxose.163. The process of claim 161 , wherein the hexose comprises glucose claim 161 , allose claim 161 , altrose claim 161 , mannose claim 161 , gulose claim 161 , idose claim 161 , galactose claim 161 , and/or talose.164. The process of claim 147 , wherein the aldaric acid is selected from the group consisting of xylaric acid and glucaric acid.165. The process of claim 147 , wherein the aldaric acid comprises glucaric acid.166. The process of claim 147 , wherein the catalytically ...

INTEGRATED PROCESS FOR PRODUCING CELLULOSIC PULP AND POLYOLS STREAM

It is disclosed an integrated process for producing at least a cellulosic pulp comprising cellulose in the form of fibers and a polyols stream from a ligno-cellulosic feedstock comprising cellulose, hemicellulose and lignin. The process comprises the steps of: 117-. (canceled)18. An integrated process for producing at least a cellulosic pulp comprising cellulose in the form of fibers and a polyols stream from a ligno-cellulosic feedstock comprising cellulose , hemicellulose and lignin , wherein the process comprises the steps of:a) treating the ligno-cellulosic feedstock to produce the cellulosic pulp and at least a liquid sugar stream comprising water and monomeric sugars derived from the hemicellulose of the lignocellulosic feedstock;b) catalytically converting the monomeric sugars of the liquid sugar stream to a polyols mixture, comprising primary polyols and secondary polyols;c) separating at least a portion of the polyols mixture to produce at least the polyols stream and a residual stream, wherein the polyols stream comprises the majority by weight of the primary polyols and the residual stream comprises the majority by weight of the secondary polyols;d) recovering a first thermal energy from the residual stream in a first recovery unit.19. The integrated process of claim 18 , wherein the treatment of the ligno-cellulosic feedstock comprises the steps of:i. soaking the ligno-cellulosic feedstock in the presence of a process fluid comprising water at a temperature between 100° C. and 210° C. for a time between 1 minute and 24 hours to produce a soaking liquid comprising oligomeric sugars and a soaked ligno-cellulosic feedstock;ii. treating the soaking liquid comprising oligomeric sugars to produce at least the liquid stream comprising monomeric sugars;iii. treating the soaked ligno-cellulosic feedstock in the presence of a chemical agent to produce at least a cellulosic stream comprising the cellulosic pulp and an effluent stream comprising at least a portion ...

A CATALYTIC PROCESS FOR THE PRODUCTION OF PROPYLENE GLYCOL FROM GLYCEROL, A COPPER AND CERIUM CATALYST, AND A PROCESS TO PRODUCE SUCH CATALYST

A process for producing propylene glycol from glycerol including a catalyst of Cu and Ce at concentrations of up to 15% of each metal. In addition, it is described a catalyst of Cu and Ce to perform the selective reduction of glycerol and the process of production of such catalyst. 1. A catalytic process for producing propylene glycol by the selective reduction of glycerol comprising a catalyst of copper and cerium supported on alumina , wherein the concentration of Cu is of up to 15% in weight , the concentration of Ce is of up to 15% in weigh.2. The process of wherein the operating conditions comprise a temperature between 170 and 200° C. claim 1 , a total pressure of 1 atm claim 1 , a partial pressure of Hranging between 0.3 and 1 atm claim 1 , a relation of helium/hydrogen ranging between 0 and 3/2 claim 1 , a concentration of glycerol ranging between 20 and 50% in weight claim 1 , a liquid hourly space velocity ranging between 0.05 and 15.00 h claim 1 , a contact time ranging between 0.03 and 5.00 minutes.3. A catalyst for the process of comprising copper and cerium supported on alumina claim 1 , wherein the concentration of Cu is of up to 15% in weight claim 1 , the concentration of Ce is of up to 15% in weight.4. The catalyst of wherein the concentration of Cu is of up to 7% in weight and the concentration of Ce is of up to 7% in weight.5. The catalyst of comprising: an alumina support with specific surface ranging between 150 and 250 mgand pore volume ranging between 0.1 and 1.0 cmg; copper and cerium precursors.6. A process for producing the catalyst of claim 3 , comprising the following steps:a. grinding the alumina support and sieving to a particle size ranging between 35 and 80 mesh;b. conditioning the alumina particles at 110° C. for one hour and then burning them in air stream at 500° C. for 3 hours;c. adding drop by drop the solution of the precursor of a first metal on the support to damp the whole mass, with ongoing stirring, until wet particles ...

PROCESS FOR THE PREPARATION OF GLYCOLS

The invention provides a process for the preparation of ethylene glycol and 1,2-propylene glycol from starting material comprising one or more saccharide, wherein the process comprises the steps of: i) providing the starting material and hydrogen to a first reactor and reacting said starting material and hydrogen therein in the presence of a solvent and a first catalyst system comprising a retro-aldol catalyst composition and a hydrogenation catalyst composition; ii) continuously removing a first reactor product stream from the first reactor, said first reactor product stream comprising ethylene glycol, 1,2-propylene glycol and in the range of from 2 to 40 wt % of sugar alcohols; iii) contacting said first reactor product stream in a second reactor in the presence of hydrogen with a second catalyst system comprising at least a hydrogenation catalyst composition; and iv) converting a portion of the sugar alcohols in the second reactor into ethylene glycol and/or 1,2-propylene glycol to provide a second reactor product stream comprising ethylene glycol, 1,2-propylene glycol and in the range of from 10 to 80% of the amount of sugar alcohols present in the first reactor product stream. 1. A process for the preparation of ethylene glycol and 1 ,2-propylene glycol from starting material comprising one or more saccharide , wherein the process comprises the steps of:i) providing the starting material and hydrogen to a first reactor and reacting said starting material and hydrogen therein in the presence of a solvent and a first catalyst system comprising a retro-aldol catalyst composition and a hydrogenation catalyst composition;ii) continuously removing a first reactor product stream from the first reactor, said first reactor product stream comprising ethylene glycol, 1,2-propylene glycol and in the range of from 2 to 40 wt % of sugar alcohols;iii) contacting said first reactor product stream in a second reactor in the presence of hydrogen with a second catalyst system ...

CONTINUOUS PROCESS FOR PRODUCING AN ETHYLENE GLYCOL STREAM

It is disclosed a continuous process for producing a polyols stream comprising ethylene glycol and propylene glycol, wherein a liquid sugar stream comprising water and at least a monomeric sugar is introduced into a first reaction zone and subjected to a first reaction, which is a hydrogenation reaction of the at least a monomeric sugar, at a first catalytic conditions and in the presence of a first hydrogen gas to produce an hydrogenated mixture comprising at least a sugar alcohol. At least a portion of the hydrogenated mixture and at least a portion of the first hydrogen gas are then transferred to a second reaction zone and subjected to a second reaction, which is a hydrogenolysis reaction of the at least a sugar alcohol, at second catalytic conditions to produce a hydrogenolysis mixture comprising at least a polyol. The second reaction occurs in the presence of a second hydrogen gas, wherein the second hydrogen gas comprises the portion of the first hydrogen gas which has been transferred to the second reaction. The first reaction is conducted at a first reaction pressure which is greater than or equal to the second reaction pressure, and the hydrogen gas is then released at the end of the conversion process of the second reaction zone at a discharge pressure which is less than the pressure of the first reaction. In this way, the transferring of at least a portion of the hydrogenated mixture and at least a portion of the first hydrogen gas from the first reaction zone to the second reaction zone may be done without the use of any pumping system, specifically of a pumping system which is capable of pumping a pressurized liquid/gas mixture. 132-. (canceled)33. A continuous process for producing a polyols stream comprising ethylene glycol and propylene glycol , wherein the process comprises the steps of:a. introducing a first hydrogen gas and a liquid sugar stream, said liquid sugar stream comprising water and at least a monomeric sugar, into a first reaction zone, ...

SHAPED POROUS CARBON PRODUCTS

Shaped porous carbon products and processes for preparing these products are provided. The shaped porous carbon products can be used, for example, as catalyst supports and adsorbents. Catalyst compositions including these shaped porous carbon products, processes of preparing the catalyst compositions, and various processes of using the shaped porous carbon products and catalyst compositions are also provided. 1160-. (canceled)161. A process for the hydrogenolysis of glycerol comprising feeding a feed composition comprising glycerol to a reaction zone and reacting the glycerol with hydrogen in the presence of a catalyst composition of in the reaction zone to form a reaction product comprising propylene glycol and/or ethylene glycol , wherein the catalyst composition comprises a shaped porous carbon product as a catalyst support and a catalytically active component or precursor thereof , wherein the shaped porous carbon product comprises:(a) carbon black and{'sup': 2', '2', '3, '(b) a carbonized binder comprising a carbonization product of a water soluble organic binder and wherein the shaped porous carbon product has a BET specific surface area from about 20 m/g to about 500 m/g, a mean pore diameter greater than about 5 nm, a specific pore volume greater than about 0.1 cm/g, a carbon black content of at least about 35 wt. %, and a carbonized binder content from about 20 wt. % to about 50 wt. %, and'}wherein the shaped porous carbon product has a radial piece crush strength greater than about 4.4 N/mm (1 lb/mm) and/or a mechanical piece crush strength greater than about 22 N (5 lbs).162. A process for the hydrogenolysis of glycerol comprising feeding a feed composition comprising glycerol to a reaction zone and reacting the glycerol with hydrogen in the presence of a catalyst composition in the reaction zone to form a reaction product comprising propylene glycol and/or ethylene glycol , wherein the catalyst composition comprises a catalytically active component ...

Thermochemical preparation of monoalcohols from biomass

A process for converting polyhydric alcohols to monoalcohols in a counter current column reactor with a metal based catalyst supported on a porous membrane coated over a tubular system that delivers hydrogen where a hydrocarbon (low polarity) liquid solvent is fed at the bottom of the column reactor and an aqueous liquid having polyhydric alcohols therein is fed into the top of the reactor such that the aqueous liquid flows countercurrent to the low polarity solvent liquid and further wherein the low polarity solvent liquid is less dense than the aqueous liquid such that the two liquids are subject to phase separation. Monoalcohols are formed by hydrogenolysis reactions of polyhydric alcohols on the metal catalyst. Monoalcohols phase separate from the aqueous phase to the hydrocarbon solvent. Monoalcohols are further separated from the organic solvent.

PROCESS FOR THE PREPARATION OF GLYCOLS

The invention provides a continuous process for the preparation of ethylene glycol and 1, 2-propylene glycol from starting material comprising one or more saccharides, said process being carried out in a reactor system comprising a reactor vessel equipped with an external recycle loop and said process comprising the steps of: i) providing the starting material in a solvent, via an inlet, to the external recycle loop and contacting it therein with a retro-aldol catalyst composition to provide an intermediate stream; ii) then contacting said intermediate stream with hydrogen in the presence of a hydrogenation catalyst composition in the reactor vessel; iii) withdrawing a product stream comprising glycols from the reactor vessel; iv) providing a portion of said product stream, via an outlet, for separation and purification of the glycols contained therein; and v) recycling the remainder of said product stream via the external recycle loop. 1. A continuous process for the preparation of ethylene glycol and 1 ,2-propylene glycol from starting material comprising one or more saccharides , said process being carried out in a reactor system comprising a reactor vessel equipped with an external recycle loop and said process comprising the steps of:i) providing the starting material in a solvent, via an inlet, to the external recycle loop and contacting it therein with a retro-aldol catalyst composition to provide an intermediate stream;ii) then contacting said intermediate stream with hydrogen in the presence of a hydrogenation catalyst composition in the reactor vessel;iii) withdrawing a product stream comprising glycols from the reactor vessel;iv) providing a portion of said product stream, via an outlet, for separation and purification of the glycols contained therein; andv) recycling the remainder of said product stream via the external recycle loop.2. The process as claimed in claim 1 , wherein the feed stream comprising said starting material in a solvent is contacted ...