HYDROFORMYLATION PROCESS

A hydroformylation process wherein a water-soluble amine is contacted with the reaction fluid, liquid from the reactor is sent to an extraction zone, and a neutralized phosphorus acidic compound is at least partially removed from the extraction zone.

Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure

Control of an in-series, multiple, e.g., two, reaction zone, hydroformylation process for producing normal (N) and iso (I) aldehydes at a N:I ratio, the process comprising contacting an olefinically unsaturated compound, e.g., propylene, with carbon monoxide, hydrogen and a catalyst comprising (A) a transition metal, e.g., rhodium, (B) an organobisphosphite, and (C) an organomonophosphite ligand, the contacting conducted in first and subsequent reaction zones and at hydroformylation conditions comprising an olefinically unsaturated compound partial pressure in each zone, the control exercised by decreasing the olefinically unsaturated compound partial pressure in the first reaction zone to decrease the N:I ratio or increasing the olefinically unsaturated compound partial pressure in the first reaction zone to increase the N:I ratio.

Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process

A method of controlling an in-series, multiple, e.g., two, reaction zone, hydroformylation process for producing normal (N) and iso (I) aldehydes at a N:I ratio, the process comprising contacting an olefinically unsaturated compound with synthesis gas and a catalyst comprising (A) a transition metal, e.g., rhodium, (B) an organobisphosphite ligand, and (C) an organomonophosphite ligand, the contacting conducted in first and subsequent reaction zone(s) and at hydroformylation conditions comprising a transition metal concentration in each zone, the method comprising decreasing the transition metal concentration in the first reaction zone to decrease the N:I ratio or increasing the transition metal concentration in the first reaction zone to increase the N:I ratio.

Bidentate ligands for hydroformylation of ethylene

A process for the hydroformylation of ethylene, with a transition metal, e.g., rhodium, catalyst promoted with a bidentate ligand of Formula I, II or III in which each R1-R24are independently a hydrogen, a hydrocarbyl group, an aromatic ring, a heteroaromatic ring or a halogen atom, or a heterocarbyl group. X1is CH2or O, while X2is O or C(R25)2, where each R25may be the same or different and is a hydrogen, a cycloaliphatic group, an aromatic ring, a heteroaromatic ring or a halogen atom, or a heterocarbyl group, wherein two R25groups may combine in a fused ring, and Y is a pyrrole group bound via the nitrogen atom to phosphorus, wherein each pyrrole group may bear multiple substituents selected from among the groups alkyl, alkoxy, acyl, carboxyl, carboxylate, cyano, —SO3H, sulfonate, amino, trifluoromethyl and halogen.

Hydroformylation process

A multi-reaction train hydroformylation process wherein a common product-catalyst separation zone is employed.

HYDROFORMYLATION PROCESS

A multi-reaction train hydroformylation process wherein a common product-catalyst separation zone is employed. 2. The process of further comprising conducting separation in the separation zone to produce a product stream and a catalyst-containing liquid recycle stream claim 1 , splitting the recycle stream into a first recycle stream and a second recycle stream claim 1 , and returning the first recycle stream at least partially to one reaction train and returning the second recycle stream at least partially to another reaction train.3. The process of wherein at least a portion of the liquid recycle stream is sent to the second train and the liquid effluent stream from the second train is at least partially sent to the first train and at least partially sent to the product-catalyst separation zone.4. The process of wherein the separating in the common product-catalyst separation zone comprises vaporization claim 1 , wherein the term vaporization refers to unit operations which are selected from the group consisting of solvent extraction claim 1 , membrane separation claim 1 , crystallization claim 1 , phase separation or decanting claim 1 , filtration claim 1 , distillation claim 1 , and any combination thereof.5. The process of wherein at least one train produces at least one process or effluent stream claim 1 , and at least part of the process or effluent stream is added to at least one reactor in the other train.6. The process of wherein the second train produces at least one vapor stream claim 1 , at least part of which is sent to at least one reactor in the first train.7. The process of wherein the effluent stream from the second train is sent to a reaction zone in the first train that is downstream of the first reaction zone in the first train.8. The process of wherein the olefin of the first feed stream is selected from the group consisting of propylene claim 1 , ethylene claim 1 , and mixtures thereof.9. (canceled)10. The process of wherein the olefin of the ...

Catalyst preparation process

A process for forming a catalyst from a catalytic metal precursor, a chelating bisphosphite and a bulky monophosphite, with a slightly greater than stoichiometric amount of chelating bisphosphite relative to catalytic metal under a CO partial pressure at least 25 psig.

STABILIZED ORGANOPHOSPHOROUS COMPOUNDS

A hydroformylation process wherein the hydrolyzable organophosphorous ligand component of the catalyst is supplied as a stabilized ligand composition comprising a hydrolyzable organophosphorous ligand and, per 100 moles compound, from 0.05 to 13 acid-neutralizing equivalents of an acid scavenger. 1. A process comprising: (a) contacting CO , H , and at least one olefin in a reaction zone under hydroformylation conditions sufficient to form at least one aldehyde product in the presence of a catalyst comprising , as components , a transition metal and a hydrolyzable organophosphorous ligand , and (b) providing the ligand as a ligand composition comprising the ligand and from 0.05 to 13 acid-neutralizing equivalents of an acid scavenger per 100 moles ligand.2. The process of further comprising claim 1 , prior to providing the ligand composition claim 1 , storing the ligand composition under a substantially oxidizer-free atmosphere claim 1 , under vacuum claim 1 , or both.3. The process of wherein the ligand composition is stored for a period of at least 30 days.4. The process of wherein the total weight of the hydrolyzable organophosphorous ligand and the acid scavenger is at least 50 wt % claim 1 , based on the total weight of the ligand composition.5. The process of wherein the acid scavenger includes at least one compound selected from: triethanolamine (TEA) and ethoxylates thereof claim 1 , methyldiethoxyamine claim 1 , dimethylethoxyamine claim 1 , ethyldiethoxyamine claim 1 , tri-3-propoxyamine claim 1 , tri-(2-(methanol)ethyl)amine claim 1 , tri-isopropanolamine and propoxylates thereof claim 1 , 4-hydroxyl-2 claim 1 ,2 claim 1 ,6 claim 1 ,6-tetramethylpiperidine claim 1 , bis(2 claim 1 ,2 claim 1 ,6 claim 1 ,6-tetramethyl-4-piperidyl) sebacate claim 1 , triethylamine claim 1 , tri-n-propylamine claim 1 , tri-n-butylamine claim 1 , tri-iso-butylamine claim 1 , tri-iso-propylamine claim 1 , tri-n-hexylamine claim 1 , tri-n-octylamine claim 1 , dimethyl-iso- ...

Controlling the Normal:ISO Aldehyde Ratio in a Mixed Ligand Hydroformylation Process

A method of controlling an in-series, multiple, e.g., two, reaction zone, hydroformylation process for producing normal (N) and iso (I) aldehydes at a N:I ratio, the process comprising contacting an olefinically unsaturated compound with synthesis gas and a catalyst comprising (A) a transition metal, e.g., rhodium, (B) an organobisphosphite ligand, and (C) an organomonophosphite ligand, the contacting conducted in first and subsequent reaction zone(s) and at hydroformylation conditions comprising a transition metal concentration in each zone, the method comprising decreasing the transition metal concentration in the first reaction zone to decrease the N:I ratio or increasing the transition metal concentration in the first reaction zone to increase the N:I ratio. 1. A method of controlling a multi-reaction zone , hydroformylation process for producing normal (N) and iso (I) aldehydes at a N:I ratio , the process comprising contacting an olefinically unsaturated compound with carbon monoxide , hydrogen and a catalyst comprising (A) a transition metal , (B) an organopolyphosphite ligand (obpl) , and (C) an organomonophosphite ligand , the contacting conducted in first and one or more subsequent reaction zones and at hydroformylation conditions comprising a metal concentration and a obpl:metal ratio in each zone , the process further comprising a product separation zone from which catalyst is recovered and recycled , the method comprising changing the transition metal concentration in the first reaction zone by one or more of the following methods:1. Partitioning the catalyst recycle from the product separation zone between the first reaction zone and one or more subsequent reaction zones; or2. Decreasing the obpl:metal ratio by adding transition metal without any organobisphosphite ligand either as a transition metal precursor or a metal-organomonophosphite compound; or3. Decreasing the transition metal concentration in the first reaction zone by removing up to 20% of ...

HYDROFORMYLATION PROCESS

A combination of calixarene bisphosphite ligand and an organophosphine ligand. The combination can be employed with a catalytic metal to form a complex catalyst. The catalyst can be employed in a hydroforaiylation process for producing a mixture of aldehydes. 1. A composition comprising a calixarene bisphosphite ligand and an organophosphine ligand.6. The composition of the organophosphine is triphenylphosphine.7. A catalytic complex comprising a transition metal complexed with the ligands of .8. A process comprising contacting CO claim 1 , Hand at least one olefin in the presence of a catalytic complex claim 1 , the complex comprising a calixarene bisphosphite ligand and an organophosphine ligand of claim 1 , under hydroformylation conditions sufficient to form at least one aldehyde product.9. A process comprising contacting CO claim 1 , Hand at least one olefin under hydroformylation conditions sufficient to form at least one aldehyde product in the presence of a catalyst having as components a transition metal claim 1 , a calixarene bisphosphite ligand and an organophosphine ligand claim 1 , wherein the molar ratio of organophosphine to catalytic metal is greater than 150:1 claim 1 , and the reaction rate is at least 0.2 g-mol/l-hr.10. The process of wherein the ratio of normal to branched products (the N/I ratio) is at least 13.11. The process of wherein the process is conducted in a reaction vessel claim 9 , and the concentration of the transition metal is greater than about 1 part per million (ppm) and less than about 1 claim 9 ,000 ppm claim 9 , based on the weight of hydroformylation reaction fluid in the vessel.12. The process of wherein the process temperature is greater than about −25° C. and less than about 200° C. claim 9 , wherein the total gas pressure comprising carbon monoxide claim 9 , hydrogen claim 9 , and olefinic reactant(s) ranges from greater than about 25 psia (173 kPa) to less than about 2 claim 9 ,000 psia (14 claim 9 ,000 kPa) claim 9 , ...

Mitigation of Fouling in Hydroformylation Processes by Water Addition

The extraction process for removing metal salts from an organic hydroformylation reaction fluid (“HRF”) prior to returning the HRF to a reaction zone of a hydroformylation process, the extraction process comprising the step of contacting the HRF with an aqueous buffer solution, is improved by contacting the HRF with water in addition to that present in the aqueous buffer solution, i.e., with added water. 1. In an extraction process for removing metal salts from an organic hydroformylation reaction fluid (“HRF”) prior to returning the HRF to a reaction zone of a hydroformylation process , the HRF comprising an organophosphorous ligand and a metal-organophosphorous ligand complex , the extraction process comprising the step of contacting the HRF with an aqueous buffer solution within a buffer extraction zone of the hydroformylation process , the reaction zone located upstream of the buffer extraction zone , the improvement comprising the step of contacting outside of the buffer extraction zone the HRF with water in addition (“added water”) to the water present in the aqueous buffer solution.2. The extraction process of in which the hydroformylation process further comprises a product separation zone located downstream of the reaction zone and upstream of the extraction zone claim 1 , and the added water and the HRF are contacted with one another in at least one of the reaction zone or the separation zone.3. The extraction process of in which the added water is contacted with the HRF downstream of the extraction zone and prior to the return of the HRF to the reaction zone.4. The extraction process of further comprising a salt extraction zone located downstream of the buffer extraction zone claim 1 , and the HRF is contacted with the added water in the salt extraction zone and prior to the return of the HRF to the reaction zone.5. The extraction process of in which the salt extraction zone and buffer extraction zone are located in separate vessels.6. The extraction ...

Methods to Store Transition Metal Organophosphorous Ligand Based Catalysts

The catalyst solution used in a hydroformylation process is prepared for storage by first reducing its acid concentration and/or water content, and then storing the solution under a blanket of syngas and/or an inert gas. Alternatively, or in addition to, the catalyst solution can be stored with an aqueous buffer comprising materials that will neutralize and/or absorb the acid species within the catalyst solution. 2. The method of in which the acid concentration is reduced by one or more of extraction claim 1 , base addition and precipitation.3. The method of in which the water content of the catalyst solution is reduced to no more than 0.8 wt %.5. The method of in which the aqueous buffer solution comprises at least one of a substituted amine or an epoxide.6. The method of in which the catalyst solution is stored with the aqueous buffer solution as a separate phase in contact with the catalyst solution.7. The method of in which the catalyst solution and aqueous buffer solution are stored in a mixed and agitated state.8. The method of in which the catalyst solution is stored under a blanket of syngas.9. The method of in which the catalyst solution is stored under a blanket of an inert gas.10. The method of in which the catalyst solution is stored under a blanket of syngas in combination with one or more inert gases.11. The method of in which the catalyst solution is stored within equipment of the hydroformylation process.12. The method of in which the catalyst solution is stored outside of the equipment of the hydroformylation process.13. The method of in which the transition metal of the hydroformylation catalyst is rhodium.14. The method of in which the acidic species include aldehyde-phosphonic and phosphoric acids.15. The method of in which the catalyst solution is stored under a blanket of syngas.16. The method of in which the catalyst solution is stored under a blanket of an inert gas.17. The method of in which the catalyst solution is stored under a blanket of ...

PROCESSES FOR PRODUCING ORGANOPHOSPHOROUS COMPOUNDS

The present invention relates to processes for producing organophosporous compositions having low acid content as well as processes for reprocessing partially degraded organophosporous compositions that contain high levels of phosphorous acid. In one embodiment, a process comprises: (a) receiving a solid organophosphite compound that has been recrystallized or triturated, wherein the solid organophosphite compound comprises phosphorous acid; (b) dissolving the solid organophosphite compound in a an aromatic hydrocarbon solvent in the absence of water and free amine, wherein the hydrocarbon solvent comprises an aromatic hydrocarbon, a saturated aliphatic hydrocarbon, or a mixture thereof; and (c) removing undissolved phosphorous acid from the solution, wherein the acid content of the organophosphite following step (c) is 30 ppm or less. 1. A process comprising: (a) receiving a solid organophosphite compound that has been recrystallized or triturated , wherein the solid organophosphite compound comprises phosphorous acid; (b) dissolving the solid organophosphite compound in a hydrocarbon solvent , wherein the hydrocarbon solvent comprises an aromatic hydrocarbon , a saturated aliphatic hydrocarbon , or a mixture thereof; and (c) removing undissolved phosphorous acid from the solution , wherein the acid content of the organophosphite following step (c) is 30 ppm or less.2. The process of claim 1 , wherein the undissolved phosphorous acid is removed by filtration.3. The process of claim 1 , wherein the undissolved phosphorous acid is removed by centrifugation.4. The process of claim 1 , wherein the acid content of the organophosphite following step (c) is 10 ppm or less.5. The process of claim 1 , wherein the acid content of the organophosphite following step(c) is 5 ppm or less.6. The process of claim 1 , further comprising (d) concentrating the organophosphite in hydrocarbon solution; (e) combining the concentrated organophosphite in hydrocarbon solution with an anti- ...

PROCESSES FOR PRODUCING ORGANOPHOSPHOROUS COMPOUNDS

The present invention relates to processes for producing organophosporous compositions having low acid content as well as processes for reprocessing partially degraded organophosporous compositions that contain high levels of phosphorous acid. In one embodiment, a process comprises: (a) receiving a solid organophosphite compound that has been recrystallized or triturated, wherein the solid organophosphite compound comprises phosphorous acid; (b) dissolving the solid organophosphite compound in an organic solvent; (c) treating the solution with a weakly basic adsorbent; and (d) collecting the treated organophosphite solution, wherein the acid content of the organophosphite following step (d) is 30 ppm or less. 1. A process comprising: (a) receiving a solid organophosphite compound that has been recrystallized or triturated , wherein the solid organophosphite compound comprises phosphorous acid; (b) dissolving the solid organophosphite compound in an organic solvent; and (c) treating the solution with a weakly basic adsorbent; and (d) collecting the treated organophosphite solution , wherein the acid content of the organophosphite following step (d) is 30 ppm or less.2. The process of claim 1 , wherein the weakly basic adsorbent comprises a metal oxide claim 1 , a metal carbonate claim 1 , or an anionic clay having an effective pKa of less than 12 or a weakly basic ion exchange resin.3. The process of claim 2 , wherein the weakly basic adsorbent comprises a weakly basic ion exchange resin claim 2 , and the weakly basic ion exchange resin comprises at least 10 equivalents of a basic moiety per mole of acid in the organophosphite solution.4. The process of claim 1 , wherein the solid organophosphite compound is dissolved in the organic solvent in the absence of free amine.5. The process of claim 1 , wherein the solvent comprises toluene claim 1 , xylenes claim 1 , diethyl ether claim 1 , dichloromethane claim 1 , ethyl acetate claim 1 , butyraldehyde claim 1 , ...

PROCESS FOR CONVERTING OLEFINS TO ALCOHOLS, ETHERS, OR COMBINATIONS THEREOF

Embodiments of the present invention relate to processes for converting olefins to alcohols, ethers, or combinations thereof that are suitable for use as a gasoline additive. In one embodiment, the process comprises (a) receiving a feed stream, wherein the feed stream comprises one or more olefins having 2 to 5 carbon atoms in an amount of up to 80% by weight based on the weight of the feed stream; (b) hydroformylating the feed stream in the presence of a catalyst to convert at least 80% of the olefins from the feed stream to oxygenates; (c) separating a product stream from step (b) into an oxygenate stream and a stream comprising unreacted olefins, inerts, the catalyst, and the remaining oxygenates; and (d) treating the oxygenate stream to convert a plurality of the oxygenates into at least one of an alcohol, an ether, or combinations thereof having at least 3 carbon atoms, wherein at least 25 weight percent of the alcohols and ethers having at least 3 carbon atoms are branched based on the total weight of the alcohols and ethers having at least 3 carbon atoms, and wherein the alcohols, ethers, or combination thereof is suitable for use as a gasoline additive. 2. The process of claim 1 , wherein the feed stream comprises at least 50% propylene.3. The process of claim 1 , wherein the oxygenate stream in step (c) comprises an aldehyde.4. The process of claim 1 , wherein treating the oxygenate stream comprises hydrogenation of the oxygenate into an alcohol.5. The process of claim 1 , wherein the oxygenates comprise an isobutyraldehyde and wherein treating the oxygenate stream comprises hydrogenation of the isobutyraldehyde into isobutyl alcohol or diisobutyl ether.6. The process of claim 1 , wherein ethylene claim 1 , propylene claim 1 , and butene comprise at least 50% of the feed stream based on the total weight of the feed stream.7. The process of claim 1 , further comprising removing at least some of the alcohols and ethers after step (d).8. The process of claim 1 ...

METHODS TO REJUVENATE A DEACTIVATED HYDROFORMYLATION CATALYST SOLUTION

Disclosed herein are methods to rejuvenate a deactivated hydroformylation catalyst solution wherein the solution comprises rhodium, polydentate phosphine ligands, and polydentate phosphine ligand degradation products. In one embodiment, such methods comprise adding a peroxide to the deactivated hydroformylation catalyst solution. 1. A method to rejuvenate a deactivated hydroformylation catalyst solution comprising rhodium , polydentate phosphine ligands , and polydentate phosphine ligand degradation products , the method comprising: adding a peroxide to the deactivated hydroformylation catalyst solution.2. The method of claim 1 , further comprising adding additional polydentate phosphine ligand to the catalyst solution after the addition of peroxide.3. The method of claim 1 , wherein the temperature of the deactivated hydroformylation catalyst solution is between 0° C. and 40° C. when the peroxide is added.4. The method of claim 1 , wherein the deactivated hydroformylation catalyst solution further comprises at least one product aldehyde claim 1 , and further comprising removing a majority of the product aldehyde prior to adding the peroxide.5. The method of claim 4 , wherein a majority of the product aldehyde is removed by vaporization.6. The method of claim 4 , wherein the temperature of the deactivated hydroformylation catalyst solution is 70° C. or greater when the peroxide is added.7. The method of claim 4 , wherein the temperature of the deactivated hydroformylation catalyst solution is 100° C. or greater when the peroxide is added.8. The method of claim 4 , wherein the peroxide comprises hydrogen peroxide claim 4 , peroxy esters claim 4 , peroxydicarbonates claim 4 , dialkyl peroxides claim 4 , hydroperoxides claim 4 , peroxyketals claim 4 , or a combination thereof. The present disclosure relates generally to methods for rejuvenating deactivated hydroformylation catalyst solutions and in particular, to methods for rejuvenating deactivated hydroformylation ...

Methods of treating a hydroformylation catalyst solution

Disclosed herein are methods of treating a hydroformylation catalyst solution wherein the solution comprises rhodium, polyphosphoramidite ligands, and polyphosphoramidite ligand degradation products and wherein the hydroformylation catalyst solution is used to hydroformylate an olefin in an operating hydroformylation unit. In some embodiments, such methods comprise contacting the catalyst solution with a peroxide in the operating hydroformylation unit.

PROCESSES FOR PURIFYING LIGANDS

Embodiments of the present invention are directed to processes for purifying ligands such as organopolyphosphite ligands. In one embodiment, a process comprises: (a) receiving a solid organopolyphosphite compound that has been recrystallized or triturated at least once, wherein the solid organopolyphosphite compound comprises greater than one weight percent of an oxidized phosphite impurity and wherein the organopolyphosphite compound is substantially free of solvent; (b) slurrying the solid organopolyphosphite compound in a Cor higher alcohol at a temperature of at least 60° C. for at least 20 minutes to reduce the oxidized phosphite impurity in the solid phase; and (c) removing liquid comprising dissolved oxidized phosphite impurity from the slurry, wherein the residual oxidized phosphite impurity content of the organopolyphosphite compound following step (c) is 1 weight percent or less. 1. A process comprising:(a) receiving a solid organopolyphosphite compound that has been recrystallized or triturated at least once, wherein the solid organopolyphosphite compound comprises greater than one weight percent of an oxidized phosphite impurity and wherein the organopolyphosphite compound is substantially free of solvent;{'sub': '2', '(b) slurrying the solid organopolyphosphite compound in a Cor higher alcohol at a temperature of at least 60° C. for at least 20 minutes to reduce the oxidized phosphite impurity in the solid phase; and'}(c) removing liquid comprising dissolved oxidized phosphite impurity from the slurry, wherein the residual oxidized phosphite impurity content of the organopolyphosphite compound following step (c) is 1 weight percent or less.2. The process of claim 1 , wherein the organopolyphosphite is an organobisphosphite.3. The process of claim 1 , wherein the dissolved oxidized phosphite impurity is removed by filtration.4. The process of claim 1 , wherein the dissolved oxidized phosphite impurity is removed by centrifugation.5. The process of claim ...

READILY BIODEGRADABLE ALKOXYLATE MIXTURES

A mixture of octanols, nonanols and decanols is useful for the preparation of alkoxylates, which alkoxylates may be used as surfactants, which surfactants have surprisingly good biodegradability. 2. An alkoxylate mixture of wherein R1 is methyl or ethyl claim 1 , x is 3 or 4 claim 1 , y is 1 or 2 claim 1 , and m has an average value of from 1 to 15.3. An alkoxylate mixtures of wherein R1 is methyl claim 1 , x is 3 or 4 claim 1 , y is 1 or 2 claim 1 , and m has an average value of from 3 to 5.4. An alkoxylate mixture of any of wherein R1 is methyl claim 1 , R2 is hydrogen claim 1 , x is 3 or 4 claim 1 , y is 1 or 2 claim 1 , m has an average value of from 3 to 5 claim 1 , and n has an average value of 3 to 15.5. An alkoxylate mixture of wherein m is from 3 to 5 and n is from 3 to 40.6. An alkoxylate mixture of wherein m is 3 to 10 claim 1 , and n is from 1 to 40.7. An alkoxylate mixture of comprising 10 to 40 mole percent of compounds with x+y=4 claim 1 , 20 to 80 mole percent of compounds with x+y=5 claim 1 , and 10 to 40 mole percent of compounds with x+y=6 claim 1 , wherein the total mole percent is 100.8. An alkoxylate mixture of comprising 20 to 30 mole percent of compounds with x+y=4 claim 1 , 40 to 60 mole percent of compounds with x+y=5 claim 1 , and 20 to 30 mole percent of compounds with x+y=6 claim 1 , wherein the total mole percent is 100.9. A cleaning composition comprising a mixture of .10. An alkoxylate mixture of prepared by a process comprising the following steps. (1) conducting a cross aldol condensation of a mixture of butyraldehyde and valeraldehyde under reaction conditions sufficient to produce a corresponding mixture of enals; (2) hydrogenating the mixture of enals under reaction conditions sufficient to produce a mixture of alcohols; and (3) alkoxylating the mixture of alcohols in one or more stages under reaction conditions sufficient to produce the alkoxylate mixture. This disclosure relates to compounds that are useful as biodegradable ...

HYDROFORMYLATION PROCESS

A process comprising contacting a reaction fluid, which contains at least one phosphorus acidic compound, with a buffer solution to neutralize at least some amount of the phosphorus acidic compound, wherein the buffer solution comprises at least one salt of an unsaturated aliphatic carboxylic acid. 1. A process comprising contacting a reaction fluid containing (a) a phosphorus acidic compound , (b) a metal-organophosphorus ligand complex catalyst that comprises a metal of Group 8 , 9 or 10 complexed with an organophosphorous ligand , and , optionally , (c) free organophosphorus ligand , with an aqueous buffer solution to neutralize at least some amount of the phosphorus acidic compound of said reaction fluid to form a neutralized phosphorus acidic compound , wherein the buffer solution comprises a salt of an unsaturated aliphatic carboxylic acid.2. The process of wherein the unsaturated aliphatic carboxylic acid comprises at least one dicarboxylic acid.3. The process of wherein the salt comprises at least one maleate or fumarate salt.4. The process of wherein the salt comprises at least one maleate salt.5. The process of wherein the concentration of the salt in the buffer solution is from 0.001M to 0.8M.6. The process of wherein the concentration of the salt in the buffer solution is from 0.01 to 0.04M.7. The process of wherein the pH of the buffer solution is from 6 to 8.8. The process of wherein the contacting is done in a countercurrent manner.9. The process of wherein the reaction fluid comprises an organic phase and the buffer solution comprises an aqueous phase.10. The process of wherein the neutralized phosphorus acidic compound is separated from the process. This application claims priority from provisional application Ser. No. 61/655,183, filed Jun. 4, 2012, which is incorporated herein by reference in its entirety.This invention relates to hydroformylation processes. In one aspect, the invention relates to a process for the mitigation of catalyst ...

METHOD FOR THE PREPARATION OF A STABILIZED ORGANOPHOSPHOROUS COMPOUND SOLUTION

A process involving admixing a ligand and an alkanolamine. The process allows the use of ligand despite the presence of contaminating amounts of phosphorus acid, and improves the shelf life of premixed ligand solutions. 1. A process comprising: preparing a solution from raw materials comprising a solvent , an alkanolamine and a ligand raw material comprising a hydrolyzable organophosphorus ligand , wherein the raw materials have a total acidity equivalent to at least 200 ppmw phosphorous acid , based on the weight of the ligand , wherein the concentration of alkanolamine in the solution is from 0.025 to 1 wt % based on the total weight of the solution , and wherein the solution is substantially free of transition metals.2. The process of wherein the ligand raw material is a solid ligand claim 1 , and comprises greater than 200 claim 1 , preferably greater than 300 claim 1 , ppmw phosphorous acid.3. The process of wherein the solvent comprises an alcohol and/or aldehyde.4. The process of wherein the concentration of the alkanolamine is from 0.2 to 0.7 wt % based on the total weight of the solution.5. The process of wherein the alkanolamine includes at least one compound selected from triethanolamine claim 1 , triisopropanolamine claim 1 , methyldiethanolamine claim 1 , dimethylethanolamine and ethyldiethanolamine6. The process of wherein the alkanolamine includes at least one compound selected from triethanolamine and triisopropanolamine7. The process of wherein the alkanolamine is triethanolamine.8. The process of further comprising feeding the ligand solution to a hydroformylation process.9. The process of wherein the hydroformylation process comprises a reaction zone and an extraction zone claim 8 , and wherein at least a portion of the solution is fed from a mix tank to the reaction zone and/or the extraction zone of the hydroformylation process.10. The process of wherein the solution is fed to the extraction zone.11. The process of wherein the hydroformylation ...

CRYSTALLINE LIGAND

A ligand crystal structure of 6,6′-[[3,3′,5,5′-tetrakis(1,1-dimethylethyl)-[1,1′-biphenyl]-2,2′-diyl]bis(oxy)]bisdibenzo[d,f][1,3,2]-dioxaphosphepin. Formule (I) 1. A crystalline form of 6 ,6′-[[3 ,3′ ,5 ,5′-tetrakis(1 ,1-dimethylethyl)-[1 ,1′-biphenyl]-2 ,2′-diyl]bis(oxy)]bisdibenzo[d ,f][1 ,3 ,2]-dioxaphosphepin , which displays its two strongest reflections , stated as 2Θ values , at 7.8±0.2° and 19.7±0.2° in an X-ray powder diffractogram , measured at 25° C. with Cu-Kα radiation.3. The crystalline form of that is solvent-free.4. The crystalline form of lacking a significant reflection at 8.5±0.2° 2θ in an X-ray powder diffractogram claim 1 , measured at 25° C. with Cu-Kα radiation.5. The crystalline form of having a melting point of 202-208° C. claim 1 , as determined by DSC.6. The crystalline form of having a DSC plot that exhibits an initial endothermic transition with a peak at 206° C.7. The crystalline form of having the XRD diffractogram of .8. The crystalline form of having the TGA plot of line B. The invention relates to a crystalline form of a bisphosphite ligand.Bisphosphites are commonly used as ligands for transition-metal catalyzed reactions such as hydroformylation and hydrocyanation. One commonly used bisphosphite ligand is 6,6′-[[3,3′,5,5′-tetrakis(1,1-dimethylethyl)-[1,1′-biphenyl]-2,2′-diyl]bis(oxy)]bisdibenzo[d,f][1,3,2]-dioxaphosphepin, (hereinafter Ligand A), shown in Formula 1:Like many organic molecules, Ligand A is a crystalline material capable of existing in a number of forms. A crystalline non-solvate and various solvate forms are disclosed in U.S. Pat. No. 8,796,481 and Yuan Hao, et al. “Crystal Structure of 6,6′-(3,3′5,5′-tetra-tertbutylbiphenyl-2,2′-diyl)Bis(oxy)didibenzo[d,f]-[1,3,2]dioxaphosphepine” ., Vol 31, 673 (2012).US 2014/0288322 A1 discloses a process for preparing a fast drying form of Ligand A via treatment with a secondary alcohol, e.g., isopropanol, at 72-75° C. for several hours. The crystal structure of the resulting ...

Processes for recovery of rhodium from a hydroformylation process

The present invention generally relates to processes for the recovery of rhodium from a catalyst purge stream from a C6 or higher olefin hydroformylation process. In one embodiment, the process comprises (a) treating a catalyst-containing liquid purge stream from the hydroformylation process, wherein the catalyst comprises a precious metal and an organophosphorous ligand, with an oxidant in the presence of a separate liquid aqueous phase comprising a halide-free acid at a sufficient temperature to effect oxidation of a majority of the contained organophosphorous ligand, wherein the halide-free acid is a C1-C6 organic acid or phosphorous acid; (b) recovering the aqueous phase; (c) contacting the aqueous phase with a separate organic phase by mixing the two phases under a syngas atmosphere, wherein the separate organic phase comprises water-insoluble, hydrolysable organophosphorous ligand and recycled olefin from a hydroformylation process; and (d) separating the organic phase to be recycled back to a hydroformylation process.

Hydroformylation process

The present invention relates to hydroformylation processes for producing aldehydes. In some embodiments, the process comprises contacting in a reaction zone reactants comprising an olefin, hydrogen and CO in the presence of a rhodium-organophosphite based catalyst, optionally with free organophosphite ligand, and 0.1 to 3 weight percent, based on the total weight of the fluid in the reaction zone, of certain polymers specified herein, such that the solubility of the polymer in the aldehyde is greater than or equal to 1 weight percent at 40° C.

CATALYST PREPARATION PROCESS

A process for forming a catalyst from a catalytic metal precursor, a chelating bisphosphite and a bulky monophosphite, with a slightly greater than stoichiometric amount of chelating bisphosphite relative to catalytic metal under a CO partial pressure at least 25 psig. 1. A process comprising (A) forming a hydroformylation catalyst by contacting under reaction conditions , in the presence of a solvent , a catalytic metal precursor , at least one organopolyphosphite ligand , CO , hydrogen , a bulky organomonophosphite ligand and , optionally , an olefin , wherein: the molar organopolyphosphite-to-catalytic metal ratio is at least 1 but less than 2; the partial pressure of carbon monoxide is at least 25 psig; and the molar ratio of bulky organomonophosphite-to-catalytic metal is from 5:1 to 50:1; and then (B) allowing the organopolyphosphite ligand concentration to diminish such that the ratio of organopolyphosphite ligand-to-catalytic metal falls to less than 1.2. The process of wherein the contacting is conducted such that the organopolyphosphite ligand and the catalytic metal precursor are introduced first claim 1 , followed by addition of the bulky organomonophosphite.3. The process of wherein the organopolyphosphite and the catalytic metal precursor are contacted together prior to being contacted with the bulky organomonophosphite.4. The process of wherein the contacting is conducted such that the organopolyphosphite ligand is introduced first claim 1 , followed by addition of the catalytic metal precursor claim 1 , followed by addition of the bulky organomonophosphite.5. The process of wherein the partial pressure of carbon monoxide is from 30 psig to 250 psig.6. The process of wherein at some point in step (A) the molar organopolyphosphite-to-catalytic metal ratio is greater than 1.7. The process of wherein the at some point in step (A) molar organopolyphosphite-to-catalytic metal ratio is from 1.05 to 1.8.8. The process of wherein the at some point in step (A) ...

PROCESS FOR STABILIZING A PHOSPHITE LIGAND AGAINST DEGRADATION

A process for stabilizing a phosphite ligand against degradation in a hydroformylation reaction fluid, said process comprising adding an epoxide to the reaction fluid, and further comprising separating one or more phosphorus acidic compounds from the reaction fluid by treating the reaction fluid with an aqueous buffer solution under conditions sufficient to neutralize and remove at least some amount of the phosphorus acidic compounds from the reaction fluid. 1. A process for stabilizing a phosphite ligand against degradation in a hydroformylation reaction fluid comprising a metal-organophosphite ligand complex catalyst and the phosphite ligand , said process comprising adding to the reaction fluid from 0.001 to 5 weight percent , based on the weight of the reaction fluid , of an epoxide , and further comprising separating one or more phosphorus acidic compounds from the reaction fluid by treating at least a portion of the reaction fluid with an aqueous buffer solution under conditions sufficient to neutralize and remove at least some amount of the phosphorus acidic compounds from the reaction fluid.2. The process of wherein the epoxide addition is performed in a continuous manner.3. The process of wherein the epoxide addition is performed on an as-needed or intermittent basis.4. The process of wherein the buffer extraction is performed in a continuous manner.5. The process of wherein the buffer extraction being performed on an as-needed or intermittent basis.6. The process of wherein the buffer extraction is performed in a batch-mode.7. The process of wherein the reaction fluid includes an amine.8. The process of wherein the metal of the catalyst is Rh.9. The process of wherein at least a portion of the epoxide is added to a reactor.10. The process of wherein the reaction fluid comprises an organic phase and the aqueous buffer solution comprises a separate aqueous phase. This application claims priority from provisional application Ser. No. 61/705,194, filed Sep. 25 ...

HYDROFORMYLATION PROCESS

Some embodiments of the present invention relate to processes for reducing heavies formation in a solution comprising one or more aldehydes, such as a reaction fluid in a hydroformylation process. In some embodiments, the process comprises providing 0.1 to 5 wt. percent of an organic nitrogen compound based on the total weight of the aldehyde solution, the organic nitrogen compound comprising: wherein each of R1-R5 are independently hydrogen, an alkyl, or an aryl radical. 2. The process of wherein the organic nitrogen compound comprises benzimidazole.3. The process of or claim 1 , wherein the aldehyde solution is a reaction fluid in a hydroformylation process comprising an olefin claim 1 , hydrogen claim 1 , carbon monoxide claim 1 , and a catalyst comprising at least one of rhodium and cobalt and a hydrolysable organophosphorus ligand.4. The process of claim 3 , wherein the hydrolysable organophosphorus ligand is a bulky organomonophosphite.5. The process of wherein the catalyst comprises rhodium and the rate of rhodium loss is at least 25% less than the rate of rhodium loss in the absence of the organic nitrogen compound.6. The process of claim 3 , wherein a plurality of heavies are formed during the hydroformylation process claim 3 , wherein the rate of heavies formation is at least 10 percent less than the rate of heavies formation of when the process is carried out in the absence of the organic nitrogen compound claim 3 , and wherein the hydroformylation process is a continuous process and the rate of heavies formation is measured using gas chromatography over a period of at least seven days.7. The process of claim 3 , wherein the amount of benzimidazole in the reaction fluid is 0.25 to 2.5 weight percent based on the total weight of the reaction fluid.8. The process of claim 3 , wherein the olefin is Cor higher.9. The process of claim 3 , wherein the olefin is Cor higher.10. The process of claim 1 , wherein the aldehyde is Cor higher. The present invention ...

HYDROFORMYLATION PROCESS

Embodiments of the present invention are directed to processes to improve rhodium accountability in continuous liquid recycle hydroformylation processes. In some embodiments, a process comprises contacting in a reaction zone reactants comprising mixed C8 olefins or mixed C9 olefins, hydrogen, and carbon monoxide in the presence of a catalyst comprising rhodium and an organomonophosphite ligand to form a reaction fluid, wherein the reaction fluid is introduced to a strip gas vaporizer to produce a product stream and a vaporizer tails stream, and wherein the vaporizer tails stream comprises at least 1.2 percent by weight C8 internal olefins or at least 1.3 percent by weight C9 internal olefins. 1. A process to improve rhodium accountability in a continuous liquid recycle hydroformylation process , the process comprising:contacting in a reaction zone reactants comprising mixed C8 olefins and/or mixed C9 olefins, hydrogen, and carbon monoxide in the presence of a catalyst comprising rhodium and an organomonophosphite ligand to form a reaction fluid,wherein the reaction fluid is introduced to a strip gas vaporizer to produce a product stream and a vaporizer tails stream, and wherein the vaporizer tails stream comprises at least 1.2 percent by weight C8 internal olefins or at least 1.3 percent by weight C9 internal olefins.2. The process of claim 1 , further comprising increasing the C8 internal olefin concentration or the C9 internal olefin concentration in the vaporizer tails stream by one or more of:(a) increasing the C8 internal olefin concentration or the C9 internal olefin concentration in the reaction fluid entering the strip gas vaporizer; or(b) lowering the heavies concentration in the reaction fluid entering the strip gas vaporizer; or(c) lowering the ratio of the mass of reaction fluid fed to the strip gas vaporizer to the mass of the vaporizer tails stream; or(d) raising the temperature of a strip gas condenser associated with the strip gas vaporizer.3. The ...

HYDROFORMYLATION PROCESS

A hydroformylation process that tolerates a high level of methanol in the feed. 1. A hydroformylation process comprising:(a) contacting in a reaction zone reactants comprising an olefin, hydrogen and CO in the presence of a metal hydrolyzable phosphorous ligand complex catalyst and, optionally, free hydrolyzable phosphorous ligand, under reaction conditions sufficient to produce an aldehyde product in a reaction fluid, with the proviso that at least one of the reactants comprises methanol and that the total amount of methanol in the reactants, prior to entering the reaction zone, is from 200 ppm to 10 percent of the total weight of methanol and the reactants,(b) removing at least a portion of the reaction fluid from the reaction zone to a separation zone, and separating the reaction fluid in the separation zone to produce a hydroformylation reaction product stream and a catalyst recycle stream,(c) treating at least a portion of said catalyst recycle stream with an aqueous buffer solution under conditions sufficient to neutralize and remove at least some amount of one or more phosphorus acidic compounds from said product stream.2. The process of claim 1 , wherein the amount of methanol is at least 400 ppm.3. The process of wherein the amount of methanol is at least 1 claim 1 ,000 ppm.4. The process of wherein the amount of methanol is at least 10 claim 1 ,000 ppm.5. The process of wherein the ligand comprises at least one of a bisphosphite claim 1 , a diorganophosphite or a triorganophosphite.6. The process of wherein the metal is rhodium.7. The process of wherein the pH of the buffer solution is from 6 to 9.8. The process of wherein the ligand is a bisphosphite.9. The process of wherein the ligand is a diorganophosphite.10. The process of wherein the ligand is a triorganophosphite.11. The process of wherein the aqueous buffer is a phosphate salt.12. The process of wherein the aqueous buffer is a carboxylate salt. This application claims priority from provisional ...

Bidentate Ligands for Hydroformylation of Ethylene

A process for the hydroformylation of ethylene, with a transition metal, e.g., rhodium, catalyst promoted with a bidentate ligand of Formula I, II or III in which each R-Rare independently a hydrogen, a hydrocarbyl group, an aromatic ring, a heteroaromatic ring or a halogen atom, or a heterocarbyl group. Xis CHor O, while Xis O or C(R), where each Rmay be the same or different and is a hydrogen, a cycloaliphatic group, an aromatic ring, a heteroaromatic ring or a halogen atom, or a heterocarbyl group, wherein two Rgroups may combine in a fused ring, and Y is a pyrrole group bound via the nitrogen atom to phosphorus, wherein each pyrrole group may bear multiple substituents selected from among the groups alkyl, alkoxy, acyl, carboxyl, carboxylate, cyano, —SOH, sulfonate, amino, trifluoromethyl and halogen.

HYDROFORMYLATION PROCESS

Catalytic metal loss when using a hydroformylation catalyst comprising an organophosphite ligand is ameliorated by adding CO to a strip gas vaporizer. 1. A continuous hydroformylation process comprising: (a) removing a reaction fluid from a reactor; (b) sending the reaction fluid to a vaporizer; (c) separating the reaction fluid in the vaporizer to produce a catalyst-containing liquid stream and a gas phase stream; and (d) maintaining an average CO partial pressure in the vaporizer of greater than 16 psia (110 kPa).2. A continuous hydroformylation process comprising:(a) feeding a reaction fluid comprising one or more products, one or more heavy by-products, a transition metal-organophosphite ligand complex catalyst, one or more unconverted reactants, and one or more inert lights into a vaporizer;(b) removing from the vaporizer an overhead gas stream comprising one or more products, one or more unconverted reactants, one or more inert lights, and a portion of the heavy by-products, and feeding said overhead gas stream into a condenser;(c) removing from the condenser a condenser overhead gas stream comprising one or more unconverted reactants and one or more inert lights;(d) recycling at least a portion of said condenser overhead gas stream to the vaporizer;(e) introducing to the vaporizer, in addition to the condenser overhead gas stream, a gas stream comprising CO, such that the average CO partial pressure in the vaporizer is greater than 16 psia (110 kPa); and(f) removing as a tails stream from the vaporizer, a liquid recycle catalyst stream comprising the transition metal-organophosphite ligand complex catalyst and the balance of the heavy by-products.3. The process of wherein the average CO partial pressure in the vaporizer is at least 20 psia (138 kPa).4. The process of wherein the average CO partial pressure in the vaporizer is at least 25 psia (172 kPa).5. The process of wherein the process outlet temperature of the vaporizer is at least 80° C. claim 1 , and ...

Catalyst preparation process

CONTINUOUS HYDROFORMILLATION PROCESS

perda catalítica de metal quando usando um catalisador de hidroformilação compreendendo um ligante organofosfito é melhorada pela adição de co para um vaporizador de gás de separação. catalytic loss of metal when using a hydroformylation catalyst comprising an organophosphite binder is improved by adding co to a separating gas vaporizer.

TRANSMISSION DEVICE CONNECTING TREES LEADING AND LEAD ANGULARLY

L'INVENTION CONCERNE UN DISPOSITIF DE TRANSMISSION COMPORTANT DES ELEMENTS QUI S'ENCLENCHENT ET SE VERROUILLENT ENTRE EUX POUR RELIER DIRECTEMENT ENTRE EUX DES ARBRES MENANT ET MENE DISPOSES ANGULAIREMENT. LES ELEMENTS ENCLENCHES ET VERROUILLES ENTRE EUX COMPRENNENT DES EBAUCHES 32, 36 DE PIGNONS ET DE ROUES DENTEES LATERALES, UTILISEES NORMALEMENT DANS UN BOITIER CLASSIQUE 16 DE DIFFERENTIEL. CES EBAUCHES 32, 36 PRESENTENT DES SURFACES COMPLEMENTAIRES DESTINEES A S'ENCLENCHER ETROITEMENT LES UNES AVEC LES AUTRES AFIN DE LES EMPECHER DE TOURNER PAR RAPPORT AU BOITIER 16 DU DIFFERENTIEL. UNE TRANSMISSION DIRECTE DE PUISSANCE EST AINSI ETABLIE ENTRE L'ARBRE MENANT 12 ET LES ARBRES DE SORTIE 14, 14. DOMAINE D'APPLICATION: TRANSMISSIONS DE VEHICULES. THE INVENTION RELATES TO A TRANSMISSION DEVICE INCLUDING ELEMENTS WHICH SNAP AND LOCK BETWEEN THEM TO CONNECT DIRECTLY BETWEEN THE DRIVE AND DRIVEN SHAFTS ARRANGED ANGULARLY. THE SNAPS AND LATCHES BETWEEN THEM INCLUDE 32 BLADES, 36 OF SPROCKETS AND SIDE GEAR WHEELS, NORMALLY USED IN A CLASSIC 16 DIFFERENTIAL HOUSING. THESE BLADES 32, 36 PRESENT ADDITIONAL SURFACES INTENDED TO INTERLOCK CLOSELY WITH THE OTHERS IN ORDER TO PREVENT THEM FROM TURNING RELATIVE TO THE DIFFERENTIAL BOX 16. A DIRECT TRANSMISSION OF POWER IS THUS ESTABLISHED BETWEEN THE DRIVE SHAFT 12 AND THE OUTPUT SHAFTS 14, 14. FIELD OF APPLICATION: VEHICLE TRANSMISSIONS.

Catalyst composition comprising the combination of a monophopsphine, a tetraphosphine ligand and a hydroformylation process using it

The present invention relates to catalyst compositions for hydroformylation processes and to hydroformylation processes utilizing certain catalysts. In one aspect, a catalyst composition for a hydroformylation process comprises (a) a transition metal; (b) a monophosphine; and (c) a tetraphosphine having the structure described herein, and wherein the composition comprises at least 40 moles of monophosphine per mole of transition metal.

Methods to rejuvenate a deactivated hydroformylation catalyst solution

Disclosed herein are methods to rejuvenate a deactivated hydroformylation catalyst solution wherein the solution comprises rhodium, polydentate phosphine ligands, and polydentate phosphine ligand degradation products. In one embodiment, such methods comprise adding a peroxide to the deactivated hydroformylation catalyst solution.

calixarene bisphosphite ligand for use in hydroformylation processes

A calixarene bisphosphite composition for use as a ligand in a transition metal-ligand complex catalyst and in a complex catalyst precursor. The ligand is especially useful in catalysts and catalyst precursors for hydroformylation processes wherein a raffinate stream comprising a mixture of alpha, beta, and iso-olefinic isomers is hydroformylated in the presence of carbon monoxide, hydrogen, and the transition metal-ligand complex catalyst to form a mixture of linear and branched aldehyde products. The complex catalyst selectively converts the alpha and beta olefin reactants more rapidly than the iso-olefin reactant resulting in an improved molar ratio of normal (linear) to branched aldehyde products. The unconverted iso-olefinic isomer is thereafter readily separated from the aldehyde product mixture.

Controlling the normal: iso aldehyde ratio in a mixed ligand hydroformylation process

Organic catalyst for non-aqueous aldol condensation

The present disclosure provides a process. In an embodiment, the process includes providing a first blend composed of nonanals, C 8 olefins and C 7 -C 9 alkanes. The process includes adding, to the first blend, a component selected from C 4 aldehyde, C 5 aldehyde, and combinations thereof to form a non-aqueous reaction mixture having an initial water content from 0 wt% to 10 wt% water. The process includes introducing an organic base catalyst to the non-aqueous reaction mixture and heating the non-aqueous reaction mixture to a temperature from 30°C to 100°C and cross-aldol condensing the non-aqueous reaction mixture. The process includes forming a cross-aldol product composed of a component selected from C 8 enals, C 10 enals, C 13 enals, C 14 enals, and C 18 enals, and combinations thereof.

Mitigation of fouling in hydroformylation processes by water addition

The extraction process for removing metal salts from an organic hydroformylation reaction fluid ("HRF") prior to returning the HRF to a reaction zone of a hydroformylation process, the extraction process comprising the step of contacting the HRF with an aqueous buffer solution, is improved by contacting the HRF with water in addition to that present in the aqueous buffer solution, i.e., with added water.

Process for stabilizing a phosphite ligand against degradation

A process for stabilizing a phosphite ligand against degradation in a hydroformylation reaction fluid, said process comprising adding an epoxide to the reaction fluid, and further comprising separating one or more phosphorus acidic compounds from the reaction fluid by treating the reaction fluid with an aqueous buffer solution under conditions sufficient to neutralize and remove at least some amount of the phosphorus acidic compounds from the reaction fluid.

Processes for recovery of rhodium from a hydroformylation process

The present invention generally relates to processes for the recovery of rhodium from a catalyst purge stream from a C6 or higher olefin hydroformylation process. In one embodiment, the process comprises (a) treating a catalyst-containing liquid purge stream from the hydroformylation process, wherein the catalyst comprises a precious metal and an organophosphorous ligand, with an oxidant in the presence of a separate liquid aqueous phase comprising a halide-free acid at a sufficient temperature to effect oxidation of a majority of the contained organophosphorous ligand, wherein the halide-free acid is a C1-C6 organic acid or phosphorous acid; (b) recovering the aqueous phase; (c) contacting the aqueous phase with a separate organic phase by mixing the two phases under a syngas atmosphere, wherein the separate organic phase comprises water-insoluble, hydrolysable organophosphorous ligand and recycled olefin from a hydroformylation process; and (d) separating the organic phase to be recycled back to a hydroformylation process.

Hydroformylation process

本發明提供一種氫甲醯化方法，其中使水溶性胺與反應流體接觸、將來自反應器之液體傳送至萃取區且至少部分地自該萃取區移除經中和之含磷酸性化合物。

Hydroformylation process

Bidentate ligands for hydroformylation of ethylene

Processes for converting olefins to alcohols, ethers, or combinations thereof

Methods for slowing deactivation of a catalyst and/or slowing tetraphosphine ligand usage in hydroformylation processes.

La presente invención se refiere a métodos para ralentizar la desactivación de un catalizador y/o ralentizar el uso de ligando de tetrafosfina en un proceso de hidroformilación. En un aspecto, un método comprende (a) poner en contacto una olefina con monóxido de carbono, hidrógeno y un catalizador, el catalizador comprende (A) un metal de transición, (B) una tetrafosfina que tiene la estructura descrita en la presente y, opcionalmente, (C) una monofosfina que tiene la estructura descrita en la presente, el contacto se realiza en una o más zonas de reacción y en condiciones de hidroformilación; y (b) añadir monofosfina adicional que tiene la estructura descrita en la presente a una zona de reacción.

Hydroformylation process

A process comprising contacting a reaction fluid, which contains at least one phosphorus acidic compound, with a buffer solution to neutralize at least some amount of the phosphorus acidic compound, wherein the buffer solution comprises at least one salt of an unsaturated aliphatic carboxylic acid.

Processes for converting olefins to alcohols, ethers, or combinations thereof

Processes for converting olefins into alcohols, ethers or combinations thereof

Un proceso para convertir olefinas en alcoholes, éteres o combinaciones de los mismos que son adecuados para su uso como aditivo de gasolina, comprendiendo el proceso: (a) recibir un flujo de alimentación, comprendiendo el flujo de alimentación una o más olefinas que tienen de 2 a 5 átomos de carbono en una cantidad de hasta el 80% en peso con respecto al peso del flujo de alimentación, comprendiendo el flujo de alimentación al menos un 50% de propileno; (b) hidroformilar el flujo de alimentación en presencia de un catalizador para convertir al menos el 80% de las olefinas del flujo de alimentación en compuestos oxigenados en los que el catalizador comprende rodio y al menos uno de triarilfosfina, diarilalquilfosfina, dialquilarilfosfina, triorganofosfito y diorganofosfito; (c) separar un flujo de producto de la etapa (b) en un flujo de oxigenado y un flujo que comprende olefinas sin reaccionar, compuestos inertes, el catalizador y los compuestos oxigenados restantes; y (d) tratar el flujo de compuestos oxigenados para convertir múltiples compuestos oxigenados en al menos uno de un alcohol, un éter o combinaciones de los mismos que tienen al menos 3 átomos de carbono, en donde al menos el 25 por ciento en peso de los alcoholes y los éteres que tienen al menos 3 átomos de carbono están ramificados con respecto al peso total de los alcoholes y los éteres que tienen al menos 3 átomos de carbono, y en donde los alcoholes, los éteres o combinaciones de los mismos son adecuados para su uso como aditivo de gasolina. A process for converting olefins to alcohols, ethers, or combinations thereof that are suitable for use as a gasoline additive, the process comprising: (a) receiving a feed stream, the feed stream comprising one or more olefins having 2 to 5 carbon atoms in an amount of up to 80% by weight with respect to the weight of the feed stream, the feed stream comprising at least 50% propylene; (b) hydroformylating the feed stream in the presence of a catalyst to ...

Process for stabilizing a phosphite ligand against degradation

A process for stabilizing a phosphite ligand against degradation in a hydroformylation reaction fluid, said process comprising adding an epoxide to the reaction fluid, and further comprising separating one or more phosphorus acidic compounds from the reaction fluid by treating the reaction fluid with an aqueous buffer solution under conditions sufficient to neutralize and remove at least some amount of the phosphorus acidic compounds from the reaction fluid.

Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure

Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms

The present invention relates to processes for preparing isoprene and mono-olefins comprising at least six carbon atoms. In one aspect, a process comprises (a) hydroformylating a mixed C4 olefin stream, wherein the mixed C4 olefin stream comprises 1-butene, 2-butene, and optionally isobutene, with a hydroformylation catalyst, wherein the hydroformylation catalyst comprises rhodium with monodentate organophosphorous ligand and optionally polydentate organophosphorous ligand, to produce a mixture comprising linear and branched C5 aldehydes; (b) separating the branched C5 aldehydes from the linear C5 aldehydes to provide a branched C5 aldehyde stream and a linear C5 aldehyde stream; (c) dehydrating the branched C5 aldehydes in the branched C5 aldehyde stream using a dehydration catalyst to form a stream comprising isoprene; (d) hydrogenating the linear C5 aldehydes in the linear C5 aldehyde stream to form a C5 alcohol stream; (e) dehydrating the C5 alcohols in the C5 alcohol stream with a second dehydration catalyst to form a C5 olefin stream; (f) hydroformylating the C5 olefins in the C5 olefin stream to generate a C6 aldehyde stream; (g) hydrogenating the C6 aldehydes in the C6 aldehyde stream to form a C6 alcohol stream; and (h) dehydrating the C6 alcohols in the C6 alcohol stream with a third dehydration catalyst to form a C6 olefin stream.

Method for the preparation of a stabilized organophosphorous compound solution

A process involving admixing a ligand and an alkanolamine. The process allows the use of ligand despite the presence of contaminating amounts of phosphorus acid, and improves the shelf life of premixed ligand solutions.

Hydroformylation process using a symmetric bisphosphite ligand for improved control over product isomers

A process for hydroformylating an α-olefin to produce two or more aldehydes comprising a normal aldehyde and one or more iso-aldehydes with a target molar ratio of the normal aldehyde to one or more iso-aldehydes in a selectable range from 3/1 to 60/1. The process uses a transition metal-ligand complex catalyst comprising a symmetric calixarene bisphosphite ligand. The target N/I ratio is selected by controlling carbon monoxide partial pressure.

Method for the preparation of a stabilized organophosphorous compound solution

Catalyst compositions and hydroformylation processes

The present invention relates to catalyst compositions for hydroformylation processes and to hydroformylation processes utilizing certain catalysts. In one aspect, a catalyst composition for a hydroformylation process comprises (a) a transition metal; (b) a monophosphine; and (c) a tetraphosphine having the structure described herein, and wherein the composition comprises at least 40 moles of monophosphine per mole of transition metal.

Hydroformylation process

A hydroformylation process wherein a water-soluble amine is contacted with the reaction fluid, liquid from the reactor is sent to an extraction zone, and a neutralized phosphorus acidic compound is at least partially removed from the extraction zone.

Hydroformylation process

A hydroformylation process wherein a water-soluble amine is contacted with the reaction fluid, liquid from the reactor is sent to an extraction zone, and a neutralized phosphorus acidic compound is at least partially removed from the extraction zone.

Processes for producing organophosphorous compounds

The present invention relates to processes for producing organophosporous compositions having low acid content as well as processes for reprocessing partially degraded organophosporous compositions that contain high levels of phosphorous acid. In one embodiment, a process comprises: (a) receiving a solid organophosphite compound that has been recrystallized or triturated, wherein the solid organophosphite compound comprises phosphorous acid; (b) dissolving the solid organophosphite compound in a an aromatic hydrocarbon solvent in the absence of water and free amine, wherein the hydrocarbon solvent comprises an aromatic hydrocarbon, a saturated aliphatic hydrocarbon, or a mixture thereof; and (c) removing undissolved phosphorous acid from the solution, wherein the acid content of the organophosphite following step (c) is 30 ppm or less.

A calixarene bisphosphite ligand for use in hydroformylation processes

A calixarene bisphosphite composition for use as a ligand in a transition metal-ligand complex catalyst and in a complex catalyst precursor. The ligand is especially useful in catalysts and catalyst precursors for hydroformylation processes wherein a raffinate stream comprising a mixture of alpha, beta, and iso-olefinic isomers is hydroformylated in the presence of carbon monoxide, hydrogen, and the transition metal-ligand complex catalyst to form a mixture of linear and branched aldehyde products. The complex catalyst selectively converts the alpha and beta olefin reactants more rapidly than the iso-olefin reactant resulting in an improved molar ratio of normal (linear) to branched aldehyde products. The unconverted iso-olefinic isomer is thereafter readily separated from the aldehyde product mixture.

Method for the preparation of a stabilized organophosphorous compound solution.

La presente invención se relaciona con un proceso que involucra mezclar un ligando y una alcanolamina. El proceso permite el uso de ligando a pesar de la presencia de cantidades contaminantes de ácido fosforoso, y mejora la vida útil de las soluciones de ligandos premezclados.

HYDROFORMILATION PROCESS

PROCESSO DE HIDROFORMILAÇÃO. Um processo de hidroformilação em que uma amina solúvel em água é contatada com o fluido de reação, líquido do reator é enviado para uma zona de extração e um composto ácido de fósforo neutralizado é pelo menos parcialmente removido da zona de extração. HYDROFORMILATION PROCESS. A hydroformylation process in which a water-soluble amine is contacted with the reaction fluid, reactor liquid is sent to an extraction zone, and a neutralized acidic phosphorus compound is at least partially removed from the extraction zone.

Hydroformylation process using a symmetric bisphosphite ligand for improved control over product isomers

Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the syngas partial pressure

The present invention relates to an improved process of controlling a hydroformylation process for producing normal (N) and iso (I) aldehydes at a N:I ratio, the process comprising contacting an olefinically unsaturated compound with synthesis gas and a catalyst comprising a transition metal and an organopolyphosphite and an organomonophosphite ligand, the contacting conducted in a reaction zone operated at hydroformylation conditions, the improvement comprising feeding the synthesis gas to the reaction zone at a constant rate after having established a new syngas partial pressure target.

Methods of controlling hydroformylation processes

The present invention relates to methods of controlling hydroformylation processes for producing normal (N) and iso (I) aldehydes at a N:I ratio. In one aspect, a method of controlling a hydroformylation process comprises contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a monophosphine, and (C) a tetraphosphine having the structure described herein, the contacting conducted in one or more reaction zones and at hydroformylation conditions to produce a blend of normal (N) and iso (I) aldehydes at a N:I ratio, the method comprising at least one of increasing the N:I ratio by adding additional tetraphosphine to a reaction zone; decreasing the N:I ratio by adding additional monophosphine to a reaction zone; or increasing the N:I ratio by volatilization of the free monophosphine.

Composition with Mixed C8-C18 Alcohols and Surfactants Thereof

The present disclosure provides a composition. In an embodiment, the composition includes 2-heptylundecanol; a member selected from the group consisting of 2-ethyhexanol and 2-propylheptanol; and a mixture of an alcohol (1) and an alcohol (2), alcohol (1) having the Structure (1) wherein R 1 is selected from the group consisting of an ethyl group and a propyl group, R 2 and R 3 each independently is selected from the group consisting of hydrogen and an alkyl group, with the proviso that the total number of carbon atoms of R 1 and R 2 is 7, and alcohol (2) having the Structure (2) wherein R 4 is selected from the group consisting of an n-propyl group, an isopropyl group, an n-butyl group, and an isobutyl group.

processes to produce organophosphorous compounds

A presente invenção se refere a processos para produzir composições organfosforosas tendo baixo teor de ácido, bem como a processos para reprocessamento de composições organofosforosas parcialmente degradadas que contêm altos níveis de ácido fosforoso. Numa modalidade, um processo compreende: (a) receber um composto de organofosfito sólido que foi recristalizado ou triturado, em que o composto de organofosfito sólido compreende ácido fosforoso; (b) dissolver o composto de organofosfito sólido num solvente orgânico; (c) tratar a solução com um adsorvente fracamente básico; e (d) coletar a solução de organofosfito tratada, em que o teor de ácido do organofosfito em seguida à etapa (d) é de 30 ppm ou menos. The present invention relates to processes for producing organophosphorous compositions having a low acid content, as well as processes for reprocessing partially degraded organophosphorous compositions containing high levels of phosphorous acid. In one embodiment, a process comprises: (a) receiving a solid organophosphite compound that has been recrystallized or crushed, wherein the solid organophosphite compound comprises phosphorous acid; (b) dissolving the solid organophosphite compound in an organic solvent; (c) treating the solution with a weakly basic adsorbent; and (d) collecting the treated organophosphite solution, where the acid content of the organophosphite after step (d) is 30 ppm or less.

Hydroformylation process

The present invention relates to hydroformylation processes for producing aldehydes. In some embodiments, the process comprises contacting in a reaction zone reactants comprising an olefin, hydrogen and CO in the presence of a rhodium-organophosphite based catalyst, optionally with free organophosphite ligand, and 0.1 to 3 weight percent, based on the total weight of the fluid in the reaction zone, of certain polymers specified herein, such that the solubility of the polymer in the aldehyde is greater than or equal to 1 weight percent at 40° C.

Readily biodegradable alkoxylate mixtures

A mixture of octanols, nonanols and decanols is useful for the preparation of alkoxylates, which alkoxylates may be used as surfactants, which surfactants have surprisingly good biodegradability.

Mitigation of fouling in hydroformylation processes by water addition.

El proceso de extracción para remover sales de metal de un fluido de reacción de hidroformilación orgánico ("HRF") antes de regresar el HRF a una zona de reacción de un proceso de hidroformilación, el proceso de extracción comprende el paso de poner en contacto el HRF con una solución amortiguadora acuosa, se mejora al poner en contacto el HRF con agua además de la presente en la solución amortiguadora acuosa, es decir, con agua agregada.

Methods to rejuvenate a deactivated hydroformylation catalyst solution

Methods to rejuvenate a deactivated hydroformylation catalyst solution

Method for the preparation of a stabilized organophosphorous compound solution

A process involving admixing a ligand and an alkanolamine. The process allows the use of ligand despite the presence of contaminating amounts of phosphorus acid, and improves the shelf life of premixed ligand solutions.

Indole-functionalized bisphosphoramidites, methods for the preparation thereof, and rhodium-ligand complex

An indole-functionalized bisphosphoramidite is disclosed which has a certain formula. A method for preparing a rhodium-ligand complex comprises combining starting materials comprising: (I) a rhodium catalyst precursor, and (II) the indole-functionalized bisphosphoramidite; and optionally (III) a solvent.

Processes to improve catalytic metal accountability in hydroformylation processes

Embodiments of the present invention are directed to processes to improve rhodium accountability in continuous liquid recycle hydroformylation processes. In some embodiments, a process comprises contacting in a reaction zone reactants comprising C7-C20 olefins, hydrogen, and carbon monoxide in the presence of a catalyst comprising rhodium and an organomonophosphite ligand to form a reaction fluid, wherein the feed rate of olefins to the reaction zone is greater than 100 kilograms/hour; providing the reaction fluid to a strip gas vaporizer to produce a product stream and a vaporizer tails stream; measuring the C7-C20 olefin content in the vaporizer tails stream; and adding a C7-C20 olefins stream comprising at least 50 weight percent C7-C20 olefins to the vaporizer tails stream to maintain the C7-C20 content in vaporizer tails stream above 2 percent by weight.

Processes to improve catalytic metal accountability in hydroformylation processes

Embodiments of the present invention are directed to processes to improve rhodium accountability in continuous liquid recycle hydroformylation processes. In some embodiments, a process comprises contacting in a reaction zone reactants comprising C7-C20 olefins, hydrogen, and carbon monoxide in the presence of a catalyst comprising rhodium and an organomonophosphite ligand to form a reaction fluid, wherein the feed rate of olefins to the reaction zone is greater than 100 kilograms/hour; providing the reaction fluid to a strip gas vaporizer to produce a product stream and a vaporizer tails stream; measuring the C7-C20 olefin content in the vaporizer tails stream; and adding a C7-C20 olefins stream comprising at least 50 weight percent C7-C20 olefins to the vaporizer tails stream to maintain the C7-C20 content in vaporizer tails stream above 2 percent by weight.

Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms

The present invention relates to processes for preparing isoprene and mono-olefins comprising at least six carbon atoms. In one aspect, a process comprises (a) hydroformylating a mixed C4 olefin stream, wherein the mixed C4 olefin stream comprises 1-butene, 2 butene, and optionally isobutene, with a hydroformylation catalyst, wherein the hydroformylation catalyst comprises rhodium with monodentate organophosphorous ligand and optionally polydentate organophosphorous ligand, to produce a mixture comprising linear and branched C5 aldehydes; (b) separating the branched C5 aldehydes from the linear C5 aldehydes to provide a branched C5 aldehyde stream and a linear C5 aldehyde stream; (c) dehydrating the branched C5 aldehydes in the branched C5 aldehyde stream using a dehydration catalyst to form a stream comprising isoprene; (d) hydrogenating the linear C5 aldehydes in the linear C5 aldehyde stream to form a C5 alcohol stream; (e) dehydrating the C5 alcohols in the C5 alcohol stream with a second dehydration catalyst to form a C5 olefin stream; (f) hydroformylating the C5 olefins in the C5 olefin stream to generate a C6 aldehyde stream; (g) hydrogenating the C6 aldehydes in the C6 aldehyde stream to form a C6 alcohol stream; and (h) dehydrating the C6 alcohols in the C6 alcohol stream with a third dehydration catalyst to form a C6 olefin stream.

Processes for recovery of rhodium from a hydroformylation process

The present invention generally relates to processes for the recovery of rhodium from a catalyst purge stream from a C6 or higher olefin hydroformylation process. In one embodiment, the process comprises (a) treating a catalyst-containing liquid purge stream from the hydroformylation process, wherein the catalyst comprises a precious metal and an organophosphorous ligand, with an oxidant in the presence of a separate liquid aqueous phase comprising a halide-free acid at a sufficient temperature to effect oxidation of a majority of the contained organophosphorous ligand, wherein the halide free acid is a C1-C6 organic acid or phosphorous acid; (b) recovering the aqueous phase; (c) contacting the aqueous phase with a separate organic phase by mixing the two phases under a syngas atmosphere, wherein the separate organic phase comprises water-insoluble, hydrolysable organophosphorous ligand and recycled olefin from a hydroformylation process; and (d) separating the organic phase to be recycled back to a hydroformylation process.

Procesos para la recuperación de rodio procedente de un proceso de hidroformilación.

La presente invención generalmente se refiere a procesos para la recuperación de rodio de una corriente de purga de catalizador de un proceso de hidroformilación de olefinas C6 o superior. En una modalidad, el proceso comprende (a) tratar una corriente de purga líquida que contiene el catalizador del proceso de hidroformilación, en donde el catalizador comprende un metal precioso y un ligando organofosforado, con un oxidante en presencia de una fase acuosa líquida separada que comprende un ácido libre de haluros a una temperatura suficiente para efectuar la oxidación de la mayoría del ligando organofosforado contenido, en donde el ácido libre de haluros es un ácido orgánico C1-C6 o un ácido fosforoso; (b) recuperar la fase acuosa; (c) poner en contacto la fase acuosa con una fase orgánica separada mediante la mezcla de las dos fases bajo una atmósfera de gas de síntesis, en donde la fase orgánica separada comprende un ligando organofosforado hidrolizable e insoluble en agua y la olefina reciclada de un proceso de hidroformilación; y (d) separar la fase orgánica a reciclar de regreso a un proceso de hidroformilación.

Processes for converting olefins to alcohols, ethers, or combinations thereof

Embodiments of the present invention relate to processes for converting olefins to alcohols, ethers, or combinations thereof that are suitable for use as a gasoline additive. In one embodiment, the process comprises (a) receiving a feed stream, wherein the feed stream comprises one or more olefins having 2 to 5 carbon atoms in an amount of up to 80% by weight based on the weight of the feed stream; (b) hydroformylating the feed stream in the presence of a catalyst to convert at least 80% of the olefins from the feed stream to oxygenates; (c) separating a product stream from step (b) into an oxygenate stream and a stream comprising unreacted olefins, inerts, the catalyst, and the remaining oxygenates; and (d) treating the oxygenate stream to convert a plurality of the oxygenates into at least one of an alcohol, an ether, or combinations thereof having at least 3 carbon atoms, wherein at least 25 weight percent of the alcohols and ethers having at least 3 carbon atoms are branched based on the total weight of the alcohols and ethers having at least 3 carbon atoms, and wherein the alcohols, ethers, or combination thereof is suitable for use as a gasoline additive.

Methods of treating a hydroformylation catalyst solution

氫甲醯化方法

本發明係關於一種多反應系列氫甲醯化方法，其中使用共同的產物-催化劑分離區。

Método para controlar um processo de hidroformilação para produzir aldeídos

métodos para controlar processos de hidroformilação. a presente invenção se refere a métodos para controlar processos de hidroformilação para produzir aldeídos normais (n) e iso (i) em uma razão n:i. em um aspecto, um método para controlar um processo de hidroformilação compreende contatar uma olefina com monóxido de carbono, hidrogênio e um catalisador, o catalisador compreendendo (a) um metal de transição, (b) uma monofosfina e (c) uma tetrafosfina tendo a estrutura aqui descrita, o contato conduzido em uma ou mais zonas de reação e em condições de hidroformilação para produzir uma mistura de aldeídos normais (n) e iso (i) em uma razão n:i, o método compreendendo pelo menos um de aumentar a razão n:i pela adição de tetrafosfina adicional a uma zona de reação; diminuir a razão n:i adicionando monofosfina adicional a uma zona de reação; ou aumentar a razão n:i por volatilização da monofosfina livre.

Método para desacelerar desativação de um catalisador e/ou desacelerar uso de ligante de tetrafosfina em um processo de hidroformilação

MÉTODOS PARA DESACELERAR DESATIVAÇÃO DE UM CATALISADOR E/OU DESACELERAR USO DE LIGANDO DE TETRAFOSFINA EM PROCESSOS DE HIDROFORMILAÇÃO. A presente invenção se refere a métodos para desacelerar desativação de um catalisador e/ou desacelerar o uso de ligando de tetrafosfina em um processo de hidroformilação. Em um aspecto, um método compreende (a) contatar uma olefina com monóxido de carbono, hidrogênio e um catalisador, o catalisador compreendendo (A) um metal de transição, (B) uma tetrafosfina tendo a estrutura aqui descrita e, opcionalmente, (C) uma monofosfina tendo a estrutura aqui descrita, o contato conduzido em uma ou mais zonas de reação e em condições de hidroformilação; e (b) adicionar monofosfina adicional tendo a estrutura aqui descrita a uma zona de reação.

Preparation of organosilicon compounds with aldehyde functionality

A process for preparing an aldehyde-functional organosilicon compound comprises: 1) combining, under conditions to catalyze hydroformylation reaction, starting materials comprising (A) a gas comprising hydrogen and carbon monoxide, (B) a vinyl-functional organosilicon compound, and (C) a rhodium/ligand complex catalyst.

Hydroformylation process

The present invention relates to hydroformylation processes for producing aldehydes. In some embodiments, the process comprises contacting in a reaction zone reactants comprising an olefin, hydrogen and CO in the presence of a rhodium-organophosphite based catalyst, optionally with free organophosphite ligand, and 0.1 to 3 weight percent, based on the total weight of the fluid in the reaction zone, of certain polymers specified herein, such that the solubility of the polymer in the aldehyde is greater than or equal to 1 weight percent at 40°C.

Hydroformylation process

Sposób hydroformylowania

processo de hidroformilação

A presente invenção refere-se a processos de hidroformilação para produzir aldeídos. Em algumas modalidades, o processo compreende contatar, em uma zona de reação, reagentes que compreendem uma olefina, hidrogênio e CO na presença de um catalisador à base de ródio-organofosfito, opcionalmente com ligante de organofosfito livre e 0,1 a 3 por cento em peso, com base no peso total do fluido na zona de reação, de certos polímeros aqui especificados, de modo que a solubilidade do polímero no aldeído seja maior ou igual a 1 por cento em peso a 40 °C.

Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms

The present invention relates to processes for preparing isoprene and mono-olefins comprising at least six carbon atoms. In one aspect, a process comprises (a) hydroformylating a mixed C4 olefin stream, wherein the mixed C4 olefin stream comprises 1-butene, 2-butene, and optionally isobutene, with a hydroformylation catalyst, wherein the hydroformylation catalyst comprises rhodium with monodentate organophosphorous ligand and optionally polydentate organophosphorous ligand, to produce a mixture comprising linear and branched C5 aldehydes; (b) separating the branched C5 aldehydes from the linear C5 aldehydes to provide a branched C5 aldehyde stream and a linear C5 aldehyde stream; (c) dehydrating the branched C5 aldehydes in the branched C5 aldehyde stream using a dehydration catalyst to form a stream comprising isoprene; (d) hydrogenating the linear C5 aldehydes in the linear C5 aldehyde stream to form a C5 alcohol stream; (e) dehydrating the C5 alcohols in the C5 alcohol stream with a second dehydration catalyst to form a C5 olefin stream; (f) hydroformylating the C5 olefins in the C5 olefin stream to generate a C6 aldehyde stream; (g) hydrogenating the C6 aldehydes in the C6 aldehyde stream to form a C6 alcohol stream; and (h) dehydrating the C6 alcohols in the C6 alcohol stream with a third dehydration catalyst to form a C6 olefin stream.

Organic Catalyst for Non-Aqueous Aldol Condensation

The present disclosure provides a process. In an embodiment, the process includes providing a first blend composed of nonanals, C8 olefins and C7-C9 alkanes. The process includes adding, to the first blend, a component selected from C4 aldehyde, C5 aldehyde, and combinations thereof to form a non-aqueous reaction mixture having an initial water content from 0 wt% to 10 wt % water. The process includes introducing an organic base catalyst to the non-aqueous reaction mixture and heating the non-aqueous reaction mixture to a temperature from 30° C. to 100° C. and cross-aldol condensing the non-aqueous reaction mixture. The process includes forming a cross-aldol product composed of a component selected from C8 enals, C10 enals, C13 enals, C14 enals, and C18 enals, and combinations thereof.

Composition with Mixed C13-C14 Alcohols and Surfactants

The present disclosure provides a composition. In an embodiment, the composition includes a mixture of an alcohol (1) and an alcohol (2). Alcohol (1) has the Structure (1): alcohol (2) has the Structure (2): wherein a is an integer from 1 to 2, R 1 and R 2 each independently is selected from the group consisting of hydrogen and an alkyl group, with the proviso that the total number of carbon atoms of R 1 and R 2 is 7, and R 3 is selected from the group consisting of a butyl group, an isobutyl group, a pentyl group, and an isopentyl group.

A process for removing phosphorous acid from organophosphorous compounds

The present invention relates to processes for producing organophosporous compositions having low acid content as well as processes for reprocessing partially degraded organophosporous compositions that contain high levels of phosphorous acid. In one embodiment, a process comprises: (a) receiving a solid organophosphite compound that has been recrystallized or triturated, wherein the solid organophosphite compound comprises phosphorous acid; (b) dissolving the solid organophosphite compound in a an aromatic hydrocarbon solvent in the absence of water and free amine, wherein the hydrocarbon solvent comprises an aromatic hydrocarbon, a saturated aliphatic hydrocarbon, or a mixture thereof; and (c) removing undissolved phosphorous acid from the solution, wherein the acid content of the organophosphite following step (c) is 30 ppm or less.

Sposoby regeneracji dezatywowanego roztworu katalizatora hydroformylowania

Methods of treating a hydroformylation catalyst solution

Alcohol mixtures including linear tridecanols

An alcohol mixture includes greater than 90 wt% of a linear tridecanol based on the total weight of the alcohol mixture.

Process to minimize polyphosphine usage by making use of degradation products

The present invention relates in part to a method for slowing the polyphosphine ligand usage rate in a hydroformylation process. It has been discovered that when a target concentration of total polyphosphorous compounds comprising polyphosphine ligand and polydentate ligand degradation products is maintained in a reaction zone, the usage rate of the polyphosphine ligand may be reduced.

Processes for producing organophosphorous compounds

The present invention relates to processes for producing organophosporous compositions having low acid content as well as processes for reprocessing partially degraded organophosporous compositions that contain high levels of phosphorous acid. In one embodiment, a process comprises: (a) receiving a solid organophosphite compound that has been recrystallized or triturated, wherein the solid organophosphite compound comprises phosphorous acid; (b) dissolving the solid organophosphite compound in an organic solvent; (c) treating the solution with a weakly basic adsorbent; and (d) collecting the treated organophosphite solution, wherein the acid content of the organophosphite following step (d) is 30 ppm or less.

Preparation of propylimine-functional organosilicon compounds and primary aminopropyl-functional organosilicon compounds

An organosilicon compound with a primary aminopropyl-functional group is prepared. A catalyzed reductive amination process for combining a secondary propylimine-functional organosilicon compound with ammonia and hydrogen produces the primary aminopropyl-functional organosilicon compound.

Processo de hidroformilação para produzir um aldeído

A presente invenção refere-se a processos de hidroformilação para produzir aldeídos. Em algumas modalidades, o processo compreende contatar, em uma zona de reação, reagentes que compreendem uma olefina, hidrogênio e CO na presença de um catalisador à base de ródio- organofosfito, opcionalmente com ligante de organofosfito livre e 0,1 a 3 por cento em peso, com base no peso total do fluido na zona de reação, de certos polímeros aqui especificados, de modo que a solubilidade do polímero no aldeído seja maior ou igual a 1 por cento em peso a 40 °C.

Processes for recovering rhodium from hydroformylation processes

The present disclosure relates to processes for recovering rhodium from a hydroformylation process. In one aspect, a tails stream from a product-catalyst separation zone is provided to at least one organic solvent nanofiltration separation membrane, wherein a final permeate stream exits a final organic solvent nanofiltration separation membrane, wherein the rhodium concentration in the final permeate stream is lower than the rhodium concentration in the tails stream. The permeate stream is incinerated on-site to create a rhodium-containing ash.

Catalyst compositions and hydroformylation processes

The present invention relates to catalyst compositions for hydroformylation processes and to hydroformylation processes utilizing certain catalysts. In one aspect, a catalyst composition for a hydroformylation process comprises (a) a transition metal; (b) a monophosphine; and (c) a tetraphosphine having the structure described herein, and wherein the composition comprises at least 40 moles of monophosphine per mole of transition metal.