Method of preparing 1-chloroacetamido-1,3,3,5,5-pentamethylcyclohexane

Method of preparing 1-chloroacetamido-1,3,3,5,5-pentamethylcyclohexane, an intermediate in the synthesis of 1-amino-1,3,3,5,5-pentamethylcyclohexane (Neramexane) or a pharmaceutically acceptable salt thereof, comprising step (iii): (iii) reacting 1-hydroxy-1,3,3,5,5-pentamethylcyclohexane with chloroacetonitrile in the presence of an acid, wherein 1-hydroxy-1,3,3,5,5-pentamethylcyclohexane is employed in step (iii) as obtained in the reaction of a methylmagnesium halide with 3,3,5,5-tetramethylcyclohexanone without having been subjected to a purification step.

Method for the Hydrolysis of Substituted Formylamines into Substituted Amines

An improved method for the synthesis of substituted formylamines and substituted amines via an accelerated Leuckart reaction. The Leuckart reaction is accelerated by reacting formamide or N-alkylformamide and formic acid with an aldehyde or a ketone at a preferred molar ratio that accelerates the reaction. The improved method is applicable to various substituted aldehydes and ketones, including substituted benzaldehydes. An accelerated method for the hydrolysis of substituted formylamines into substituted amines using acid or base and a solvent at an elevated temperature. The improved method is useful for the accelerated synthesis of agrochemicals and pharmaceuticals such as vanillylamine, amphetamine and its analogs, and formamide fungicides.

Supported metal catalysts

The present invention relates to supported metal catalysts, wherein the catalysts are modified by at least one amine, a method for the preparation thereof and hydrogenation processes utilising the supported metal catalysts.

METHOD FOR PRODUCING beta-AMINOCARBONYL COMPOUND

An optically active β-aminocarbonyl compound is obtained by a Mannich reaction between an aldimine in which: nitrogen is protected and a malonic acid diester, in the presence of optically active BINOL and dialkyl magnesium (in which two alkyl groups are the same or different) in an amount 1 to 2 molar times the amount of the BINOL. 1. A method for producing a β-aminocarbonyl compound comprising carrying out a Mannich reaction between an aldimine in which nitrogen is protected and a malonic acid diester , in the presence of optically active BINOL and dialkyl magnesium (in which two alkyl groups are the same or different) in an amount 1 to 2 molar times the amount of the BINOL , to obtain an optically active β-aminocarbonyl compound.2. The method for producing a β-aminocarbonyl compound according to claim 1 , wherein the aldimine is a compound represented by R—CH═NR(wherein Ris an aryl group or an ester group claim 1 , and Ris tert-butoxycarbonyl (Boc) claim 1 , benzyloxycarbonyl (Cbz) claim 1 , 2 claim 1 ,2 claim 1 ,2-trichloroethoxycarbonyl (Troc) claim 1 , a phenyl group claim 1 , a 2-methoxyphenyl group claim 1 , a 4-methoxyphenyl group claim 1 , or a naphthyl group).3. The method for producing a β-aminocarbonyl compound according to claim 1 , wherein the malonic acid diester is a compound represented by CHX(COR)(wherein X is a hydrogen atom or a halogen atom claim 1 , and Ris alkyl claim 1 , allyl claim 1 , benzyl claim 1 , or aryl).4. The method for producing a β-aminocarbonyl compound according to claim 1 , wherein the BINOL is used in an amount of 2.5 mole percent to 10 mole percent relative to the aldimine.5. The method for producing a β-aminocarbonyl compound according to claim 1 , wherein an aromatic solvent or a halogenated hydrocarbon solvent is used as a reaction solvent. The present invention relates to a method for producing a β-aminocarbonyl compound.Mannich reactions in which a carbonyl compound is added directly to an aldimine are one. Of the most ...

Process for conversion of isobutylene to tertiary butylamine

The invention discloses an improved process for the conversion of isobutylene to tertiary butylamine with conversion up to 50% at pressure lower than 40 bar.

METHOD OF PREPARING 3,3,5,5-TETRAMETHYLCYCLOHEXANONE

Method of preparing 3,3,5,5-tetramethylcyclohexanone comprising step (i): (i) converting isophorone to 3,3,5,5-tetramethylcyclohexanone in the presence of methylmagnesium chloride. The thus prepared 3,3,5,5-tetramethylcyclohexanone may be employed in a method of preparing 1-amino-1,3,3,5,5-pentamethylcyclohexane (Neramexane) or a pharmaceutically acceptable salt thereof. 116.-. (canceled)17. A method of preparing 3 ,3 ,5 ,5-tetramethylcyclohexanone comprising step (i):(i) converting isophorone to 3,3,5,5-tetramethylcyclohexanone in the presence of methylmagnesium chloride.18. The method according to claim 17 , wherein step (i) is performed in the presence of a copper compound.19. The method according to claim 18 , wherein the copper compound is a copper(I) halide.20. The method according to claim 19 , wherein the copper(I) halide is copper(I) iodide.21. The method according to claim 17 , wherein step (i) performed in the presence of a lithium compound.22. The method according to claim 21 , wherein the lithium compound is a lithium halide claim 21 ,23. The method according to claim 22 , wherein the lithium halide is lithium chloride.24. The method according to claim 22 , wherein the molar ratio of copper(I) halide to lithium halide is in the range of from 1:1.5 to 1:2.5.25. The method according to claim 17 , wherein step (i) is performed in a solvent comprising an ether.26. The method according to claim 25 , wherein the ether is tetrahydrofuran.27. The method according to claim 17 , wherein in step (i) isophorone is converted to 3 claim 17 ,3 claim 17 ,5 claim 17 ,5-tetramethylcyclohexanone in the presence of methylmagnesium chloride claim 17 , copper(I) iodide and lithium chloride in tetrahydrofuran.28. The method according to claim 27 , wherein a solution comprising methylmagnesium chloride in tetrahydrofuran is added to a solution comprising isophorone claim 27 , copper(I) iodide and lithium chloride.29. A method of preparing 1-amino-1 claim 27 ,3 claim 27 ,3 ...

SYNTHESIS OF POLYALKYLENEPOLYAMINES HAVING A LOW COLOR INDEX BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION IN THE PRESENCE OF HYDROGEN

Process for the preparation of polyalkylenepolyamines by homogeneously catalyzed alcohol amination, in which aliphatic amino alcohols are reacted with one another or aliphatic diamines or polyamines are reacted with aliphatic diols or polyols with the elimination of water in the presence of a homogeneous catalyst and in the presence of hydrogen gas. Polyalkylenepolyamines obtainable by such processes and polyalkylenepolyamines comprising hydroxy groups, secondary amines or tertiary amines. Uses of such polyalkylenepolyamines as adhesion promoters for printing inks, adhesion promoters in composite films, cohesion promoters for adhesives, crosslinkers/curing agents for resins, primers for paints, wet-adhesion promoters for emulsion paints, complexing agents and flocculating agents, penetration assistants in wood preservation, corrosion inhibitors, immobilizing agents for proteins and enzymes. 1. A process for the preparation of polyalkylenepolyamines by homogeneously catalyzed alcohol amination , in which(i) aliphatic amino alcohols are reacted with one another or(ii) aliphatic diamines or polyamines are reacted with aliphatic diols or polyols with the elimination of water in the presence of a homogeneous catalyst and in the presence of hydrogen gas.2. The process according to claim 1 , wherein the reaction is carried out at a partial pressure of the hydrogen gas of from 0.1 to 25 MPa.3. The process according to or claim 1 , wherein the hydrogen gas engages chemically in the catalyzed alcohol amination claim 1 , thereby reducing the formation of coloring components.4. The process according to to claim 1 , wherein the catalyst is a transition metal complex catalyst.5. The process according to to claim 1 , wherein the catalyst comprises ruthenium or iridium.6. The process according to to claim 1 , wherein the catalyst comprises a nitrogen-heterocyclic carbene ligand.7. The process according to claim 6 , wherein the catalyst comprises a carbene ligand from the group ...

MONITORING OF THE STOICHIOMETRIC RATIO IN THE REACTION OF NITROAROMATICS WITH HYDROGEN

The present invention relates to a continuous process for preparing at least one aromatic amine by hydrogenation of at least one nitroaromatic by means of hydrogen, where a liquid phase comprising at least the aromatic amine and a gas phase comprising at least hydrogen are present, in the presence of a catalyst suspended in the liquid phase at a temperature of from 50 to 250° C. and a pressure of from 5 to 50 bar, wherein the pressure in the reactor is kept essentially constant by continuous adaptation of the amount of hydrogen fed to the reactor, the total amount of hydrogen fed to the reactor is monitored and the introduction of the at least one nitroaromatic is interrupted if the hydrogen uptake in the reactor is not at least 50 mol % of the amount of hydrogen required for stoichiometric reaction of the at least one nitroaromatic to form the at least one aromatic amine. 1. A continuous process for preparing at least one aromatic amine by hydrogenation of at least one nitroaromatic by means of hydrogen , where a liquid phase comprising at least the aromatic amine and a gas phase comprising at least hydrogen are present , in the presence of a catalyst suspended in the liquid phase at a temperature of from 50 to 250° C. and a pressure of from 5 to 50 bar , whereinthe pressure in the reactor is kept essentially constant by continuous adaptation of the amount of hydrogen fed to the reactor,the total amount of hydrogen fed to the reactor is monitored andthe introduction of the at least one nitroaromatic is interrupted if the hydrogen uptake in the reactor is not at least 50 mol %, preferably at least 70 mol %, particularly preferably at least 90 mol %, very particularly preferably at least 95 mol %, in particular at least 98 mol %, of the amount of hydrogen required for stoichiometric reaction of the at least one nitroaromatic to form the at least one aromatic amine.2. The process according to claim 1 , wherein the hydrogen uptake in the reactor corresponding to the ...

PRODUCTION METHOD FOR AMINO COMPOUND

The present invention relates to a process for producing an amino compound by subjecting a polyamine and an alkenyl compound to addition reaction in the presence of an alkali metal hydride compound which is capable of supplying the amino compound in a stable manner without occurrence of odor. 1: A process for producing an amino compound , the process comprising:conducting an addition reaction between a polyamine and an alkenyl compound in the presence of an alkali metal hydride compound.2: The process according to claim 1 ,wherein the conducting comprises mixing and contacting the alkali metal hydride compound with the polyamine, thereby obtaining a mixture and adding the alkenyl compound to the mixture.3: The process according to claim 1 ,wherein the conducting comprises adding the alkenyl compound intermittently in divided parts.4: The process according to claim 1 ,wherein the alkali metal hydride compound is present in an amount of from 0.01% to 3% by mass on a basis of a total amount of the alkali metal hydride compound and the polyamine.5: The process according to claim 1 , {'br': None, 'H2N—CH2-A-CH2—NH2\u2003\u2003(1),'}, 'wherein the polyamine is a polyamine represented by formula (1)wherein A is a phenylene group or a cyclohexylene group.6: The process according to claim 1 , {'br': None, 'H2N—(CH2CH2NH)n-H\u2003\u2003(2),'}, 'wherein the polyamine is a polyamine represented by formula (2)wherein n is an integer of from 1 to 5.7: The process according to claim 1 ,wherein the polyamine is a cyclic aliphatic polyamine having 9 or more carbon atoms and 2 or more amino groups in a molecule thereof as well as 3 or more active hydrogen atoms derived from amino groups.8: The process according to claim 7 ,{'b': 4', '3, 'wherein the cyclic aliphatic polyamine is menthenediamine, isophoronediamine, diaminodicyclohexyl methane, bis(-amino--methylcyclohexyl)methane, N-aminomethyl piperazine, or norbornanediamine.'}9: The process according to claim 1 ,wherein the ...

Process for Preparing Piperazine

Process for preparing piperazine of the formula I 132-. (canceled)34. The process according to claim 33 , wherein the catalytically active mass of the catalyst claim 33 , prior to its reduction with hydrogen claim 33 , comprises 20 to 65% by weight of oxygen-containing compounds of zirconium claim 33 , calculated as ZrO.35. The process according to claim 33 , wherein the catalytically active mass of the catalyst claim 33 , prior to its reduction with hydrogen claim 33 , comprises 2 to 25% by weight of oxygen-containing compounds of copper claim 33 , calculated as CuO.36. The process according to claim 33 , wherein the catalytically active mass of the catalyst claim 33 , prior to its reduction with hydrogen claim 33 , comprises 15 to 50% by weight of oxygen-containing compounds of nickel claim 33 , calculated as NiO.37. The process according to claim 33 , wherein the catalytically active mass of the catalyst claim 33 , prior to its reduction with hydrogen claim 33 , comprises 0.1 to 3% by weight of oxygen-containing compounds of molybdenum claim 33 , calculated as MoO.38. The process according to claim 33 , wherein the molar ratio of nickel to copper is greater than 1.39. The process according to claim 33 , wherein no rhenium and/or ruthenium is present in the catalytically active mass of the catalyst.40. The process according to claim 33 , wherein no iron and/or zinc is present in the catalytically active mass of the catalyst.41. The process according to claim 33 , wherein no cobalt is present in the catalytically active mass of the catalyst.42. The process according to claim 33 , wherein no oxygen-containing compounds of silicon and/or of aluminum and/or of titanium are present in the catalytically active mass of the catalyst.43. The process according to claim 33 , wherein the reaction is carried out at a temperature in the range from 185 to 215° C.44. The process according to claim 33 , wherein the reaction is carried out at an absolute pressure in the range from ...

PROCESS FOR THE RACEMIZATION OF OPTICALLY ACTIVE ARYLALKYLAMINES

Many optically active amines are valuable pharmaceuticals and intermediates for the preparation of active compounds. It is frequently the case that only one of the two enantiomers is active or not harmful, so that isolation of this enantiomer from the racemic mixture is necessary. Processes for racemate resolution make it possible to separate racemic mixtures into their enantiomers. Here, it is useful to once again racemize the enantiomer which is not required and recirculate it to racemate resolution and thus improve the yield of the desired enantiomer. The present invention relates to processes for the racemization of optically active amines, in particular arylalkylamines, in the presence of hydrogen and a hydrogenation/dehydrogenation catalyst comprising nickel, cobalt and copper as active components at elevated temperature. 2. The process of claim 1 , wherein the active components nickel claim 1 , cobalt and copper of the hydrogenation/dehydrogenation catalyst are present entirely or partly in a form of oxides before being activated by a reducing agent.3. The process of claim 1 , wherein the hydrogenation/dehydrogenation catalyst comprises an inert support material.4. The process of claim 1 , wherein the hydrogenation/dehydrogenation catalyst additionally comprises at least one further active component selected from the group consisting of zirconium claim 1 , molybdenum and palladium which further active component is present entirely or partly in a form of an oxide claim 1 , before being activated by a reducing agent.5. The process of claim 1 , wherein the reacting is carried out in the presence of an amine of formula R3NHin which R3 corresponds to the radical R3 of the optically active amine of formula I.6. The process of claim 1 , wherein the hydrogenation/dehydrogenation catalyst comprises less than 1% by weight of zinc-comprising compounds including metallic zinc claim 1 , calculated as ZnO claim 1 , based on a sum of oxygen-comprising compounds of nickel ...

METHOD FOR PRODUCING CYCLIC SILANE COMPOUND OR SALT THEREOF, SALT HAVING CYCLIC SILANE DIANION, AND CYCLIC SILANE DIANION SALT-CONTAINING COMPOSITION

An object of the present invention is to provide a production method that can efficiently produce a cyclic silane compound or a salt thereof with a high yield and to provide a novel salt having a cyclic silane dianion that is easy to handle and a cyclic silane dianion salt-containing composition. The method for producing a cyclic silane compound or a salt thereof of the present invention includes the step of allowing a halosilane compound to react in the presence of at least one of a phosphonium salt and an ammonium salt, and a compound represented by a specific formula. 2. The method for producing a cyclic silane compound or a salt thereof according to claim 1 , wherein the reaction is carried out in the presence of a basic compound.3. The method for producing a cyclic silane compound or a salt thereof according to claim 1 , wherein the phosphonium salt or the ammonium salt is a quaternary phosphonium salt or a quaternary ammonium salt.7. The cyclic silane dianion salt-containing composition according to claim 6 , wherein the salt having a cyclic silane dianion represented by the general formula (vii) is contained in an amount of 1 to 10000 parts by mass claim 6 , based on the total amount of 100 parts by mass of the salt having a cyclic silane dianion represented by the general formula (vi).8. The method for producing a cyclic silane compound or a salt thereof according to claim 2 , wherein the phosphonium salt or the ammonium salt is a quaternary phosphonium salt or a quaternary ammonium salt. (1) Field of the InventionThe present invention relates to a production method that can efficiently obtain a cyclic silane compound or a salt thereof by a simple method, a novel salt having a cyclic silane dianion, and a cyclic silane dianion salt-containing composition.(2) Description of Related ArtA silane compound is widely utilized as a raw material of silicon and silica, and a water-reactive combustible gas such as monosilane and disilane is mostly used. On the other ...

NEW METHOD FOR THE SYNTHESIS OF RASAGILINE

We have developed a new method for the synthesis of Rasagiline (Formula 1) based on the alkylation of trifluoroacetyl protected aminoindan. This protection enabled us to carry out an alkylation of aminoindan with a high yield and purity under very mild conditions with a wide range of reaction conditions and reagent selection. Considering the ease, purity and high yields of introducing and removal of the trifluoroacetyl group, this approach is a highly practical and economical way for the synthesis of rasagiline or its pharmaceutically acceptable salts. 4. A process according to the claim 2 , the alkylating reagent used in the reaction is preferably Formula 6.5. A process according to the claim 2 , the base used in alkylation (a) is preferably NaOtBu claim 2 , or KOtBu claim 2 , or CsCO claim 2 , or a mixture of CsCOand KCO.6. A process according to the claim 2 , alkylation (a) is optionally carried out in the presence of a phase transfer catalyst.7. A process according to the claim 6 , phase transfer catalyst is TBAI.8. A process according to the claim 2 , alkylation (a) is carried out in a solvent.9. A process according to the claim 8 , the solvent is preferably DMF or acetonitrile.10. A process according to the claim 2 , hydrolyzing the compound of Formula 4 is carried out in a solvent.11. A process according to the claim 2 , hydrolyzing the compound of Formula 4 is carried out with a base.12. A process according to the claim 2 , the salt is preferably mesylate salt of Formula 1.13. A process according to the claim 2 , wherein it is carried out in one pot.14. A process according to the claim 3 , wherein it is carried out in one pot. Rasagiline and its synthesis were first reported in EP 0436492 B1. This reported synthesis was simply based on the alkylation of (R)-1-Aminoindan with propargyl chloride in acetonitrile in the presence of potassium carbonate at 60° C. for 16 hours. The crude product was highly impure and required further purification with column ...

Method For The Preparation Of Cinacalcet And Intermediates And Impurities Thereof

A method for the preparation of Cinacalcet is disclosed comprising treating (R)-1-naphthyl ethylamine with an aromatic aldehyde to form (1R)-1-(2-naphthyl)-N-(aryl methylene)ethanamine derivative of Formula (IV), which is further treated with 1-(3-halopropyl)-3-(trifluoromethyl)benzene of Formula (V) to obtain an iminium salt of Formula (VI), followed by hydrolysis to obtain Cinacalcet free base. 2. The method according to claim 1 , wherein the step (a) is carried out at a temperature from about 10° C. to 150° C.3. The method according to wherein the step (a) is carried out in the presence of a solvent.4. The method according to claim 3 , wherein the solvent is selected from the group consisting of hydrocarbons claim 3 , alcohols claim 3 , C-Cether claim 3 , C-Ccyclic ether claim 3 , C-Caliphatic ester claim 3 , C-Caliphatic amides claim 3 , sulfoxide claim 3 , C-Cchlorinated hydrocarbon claim 3 , 1-ethyl-3-methyl imidazolium ethylsulfate claim 3 , and mixtures thereof.5. The method according to wherein claim 1 , the compound of Formula (III) is selected from benzaldehyde claim 1 , salisaldehyde claim 1 , p-hydroxyl benzaldehyde claim 1 , o-chlorobenzaldehyde claim 1 , p-methoxy benzaldehyde claim 1 , o-methoxy benzaldehyde claim 1 , and p-nitrobenzaldehyde.6. The method according to claim 1 , further comprising isolating the compound of Formula (I) or a salt thereof in a crystalline form.7. The method according to claim 1 , wherein the step (b) is carried out at a temperature of 80° C. to 180° C.8. The method as according to claim 7 , wherein the step (b) is carried out in the presence of a solvent.9. The method according to claim 8 , wherein the solvent is selected from the group consisting of hydrocarbons claim 8 , alcohols claim 8 , C-Cethers claim 8 , C-Ccyclic ethers claim 8 , C-Caliphatic esters claim 8 , C-Caliphatic amides claim 8 , sulfoxides claim 8 , C-Cchlorinated hydrocarbons claim 8 , 1-ethyl-3-methyl imidazolium ethyl sulfate claim 8 , and mixtures ...

METHOD FOR SYNTHESIZING 1,1-DIAMINO-2,2-DINITROETHYLENE (FOX-7) OR A SALT THEREOF

In a method for synthesizing 1,1-diamino-2,2-dinitroethylene (FOX-7) or a salt thereof, an isourea derivative cation, which consists of a C(NH)(NH) radical and a nucleofugal leaving group bonded to the carbon atom of the C(NH) (NH) radical, is reacted with a dinitromethane anion. The reaction of the isourea derivative cation with the dinitromethane anion takes place in a solution. 1. A method for synthesizing 1 ,1-diamino-2 ,2-dinitroethylene (FOX-7) or a salt thereof , which comprises the step of:{'sub': 2', '2', '2', '2, 'sup': +', '+, 'reacting an isourea derivative cation, which consists of a C(NH)(NH) radical and a nucleofugal leaving group bonded to a carbon atom of the C(NH) (NH) radical, with a dinitromethane anion.'}2. The method according to claim 1 , which further comprises performing the reacting of the isourea derivative cation with the dinitromethane anion in a polar aprotic solvent.3. The method according to claim 2 , which further comprises using dimethylformamide (DMF) as the polar aprotic solvent.4. The method according to claim 1 , which comprises selecting the nucleofugal leaving group from the group consisting of an O-alkyl claim 1 , O-methyl claim 1 , O-ethyl claim 1 , O-propyl claim 1 , O-butyl claim 1 , O-pentyl claim 1 , triazolyl claim 1 , halide claim 1 , chloride claim 1 , carbonyl halide claim 1 , carbonyl chloride claim 1 , nonaflate claim 1 , trifluoromethanesulphate claim 1 , sulphonate claim 1 , halosulphonate claim 1 , fluorosulphonate claim 1 , tosyl claim 1 , mesyl claim 1 , diazonium claim 1 , oxonium claim 1 , quaternary ammonium compound claim 1 , ester claim 1 , acid anhydride claim 1 , nitrate claim 1 , phosphate claim 1 , organic ester claim 1 , ammonium claim 1 , phenol claim 1 , alcohol and a carboxylic radical.5. The method according to claim 1 , which further comprises selecting the isourea derivative cation from the group consisting of a chloroformamidinium ion and a triazole carboxamidine ion.6. The method according to ...

HIGHLY Z-SELECTIVE OLEFIN METATHESIS

The present invention relates generally to catalysts and processes for the Z-selective formation of internal olefin(s) from terminal olefin(s) via homo-metathesis reactions. 139-. (canceled)41. The metal complex of claim 40 , wherein the ligand containing oxygen bound to M is substituted —O-aryl claim 40 , wherein the aryl group is phenyl.42. The metal complex of claim 40 , the ligand containing oxygen bound to M is substituted —O-aryl claim 40 , wherein the aryl group is biphenyl.43. The metal complex of claim 40 , the ligand containing oxygen bound to M is substituted —O-aryl claim 40 , wherein the aryl group is 1 claim 40 ,2 claim 40 ,3 claim 40 ,4-tetrahydronaphthyl or naphthyl.44. The metal complex of claim 40 , wherein the ligand containing oxygen bound to M is substituted —O-aryl claim 40 , and substituents positioned in close proximity to the metal center are alkylaryl.45. The metal complex of claim 40 , wherein the metal complex is other than W(NAr)(CHCMePh)(Pyr)(HIPTO).46. The metal complex of claim 40 , wherein the ligand containing oxygen bound to M is 3 claim 40 ,3′-di-tert-butyl-5 claim 40 ,5′ claim 40 ,6 claim 40 ,6′-tetramethyl-2′-(trimethylsilyloxy)biphenyl-2-olate (BiphenTMS) claim 40 , 2′-(tert-butyldimethylsilyloxy)-3-mesityl-5 claim 40 ,5′ claim 40 ,6 claim 40 ,6′ claim 40 ,7 claim 40 ,7′ claim 40 ,8 claim 40 ,8′-octahydro-1 claim 40 ,1′-binaphthyl-2-olate (MesBitet) claim 40 , 3 claim 40 ,3′-dimesityl-2′-(tert-butyldimethylsilyloxy)-5 claim 40 ,5′ claim 40 ,6 claim 40 ,6′ claim 40 ,7 claim 40 ,7′ claim 40 ,8 claim 40 ,8′-octahydro-1 claim 40 ,1′-binaphthyl-2-olate (MesBitet) claim 40 , or MesBitetOMe is 3 claim 40 ,3′-dimesityl-2′-methoxy-5 claim 40 ,5′ claim 40 ,6 claim 40 ,6′ claim 40 ,7 claim 40 ,7′ claim 40 ,8 claim 40 ,8′-octahydro-1 claim 40 ,1′-binaphthyl-2-olate (MesBitetOMe).49. The metal complex of claim 48 , wherein Ris tert-butyl claim 48 , optionally substituted.50. The metal complex of claim 48 , wherein Ris substituted phenyl.51. ...

METHOD FOR CLEAVING AMIDE BONDS

A method for cleaving amide bonds, comprising: 130-. (canceled)31. A method for cleaving amide bonds , comprising:a) providing a molecule comprising an amide group, wherein the amide group is a primary, secondary or tertiary amide group;{'sub': '2', 'b) reacting the molecule comprising an amide group with hydroxylamine (NHOH) or a salt thereof to cleave the amide bond of the amide group.'}32. The method according to claim 31 , wherein the method further comprises:c) recovering a product formed by the reaction of step b).33. The method according to claim 31 , wherein the amide group is an N-acyl amide group.34. The method according to claim 31 , wherein the molecule comprising an amide group further comprises a pH sensitive chiral center.35. The method according to claim 31 , wherein the molecule comprising an amide group further comprises a pH sensitive protecting group.36. The method according to claim 31 , wherein step b) comprises reacting the molecule comprising an amide group with the hydroxylamine or salt thereof at a temperature of 100° C. or less.37. The method according to claim 31 , wherein step b) comprises reacting the molecule comprising an amide group with the hydroxylamine or salt thereof for 2-200 hours.38. The method according to claim 31 , wherein step b) comprises reacting the molecule comprising an amide group with hydroxylamine in water.39. The method according to claim 31 , wherein the molar concentration of hydroxylamine in step b) is in the range of 5-20 M.40. The method according to claim 31 , wherein step b) comprises reacting the molecule comprising an amide group with a hydroxylamine salt.41. The method according to claim 40 , wherein the hydroxylamine salt is a salt of hydroxylamine and hydroiodic acid or trifluoroacetic acid.42. The method according to claim 31 , wherein the concentration of the hydroxylamine salt in step b) is in the range of 0.1-5 M.43. The method according to claim 31 , wherein the reaction in step b) is performed in ...

PREPARATION OF CHIRAL AMIDES AND AMINES

This invention provides a convenient method for converting oximes into enamides. The process does not require the use of metallic reagents. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines. The invention provides a process to convert a prochiral enamide into the corresponding chiral amide. In an exemplary process, a chiral amino center is introduced during hydrogenation through the use of a chiral hydrogenation catalyst. In selected embodiments, the invention provides methods of preparing amides and amines that include the 1,2,3,4-tetrahydro-N-alkyl-1-naphthalenamine or 1,2,3,4-tetrahydro-1-naphthalenamine substructure.

PREPARATION OF CHIRAL AMIDES AND AMINES

This invention provides a convenient method for converting oximes into enamides. The process does not require the use of metallic reagents. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines. The invention provides a process to convert a prochiral enamide into the corresponding chiral amide. In an exemplary process, a chiral amino center is introduced during hydrogenation through the use of a chiral hydrogenation catalyst. In selected embodiments, the invention provides methods of preparing amides and amines that include the 1,2,3,4-tetrahydro-N-alkyl-1-naphthalenamine or 1,2,3,4-tetrahydro-1-naphthalenamine sub structure. 151.-. (canceled) This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Patent Application No. 60/787,837 filed Mar. 31, 2006, which application is incorporated herein by reference in its entirety for all purposes.This invention relates to processes suitable for the large-scale preparation of enantiomerically- or diastereomerically-enriched chiral amides and amines prepared by these processes.Enantiomerically-enriched chiral primary amines are commonly used as resolving agents for racemic acids, as chiral auxiliaries for asymmetric syntheses and as ligands for transition metal catalysts used in asymmetric catalysis. In addition, many pharmaceuticals, such as sertraline, contain chiral amine moieties. Effective methods for the preparation of such compounds are of great interest to the pharmaceutical industry. Particularly valuable are processes that allow for the preparation of each enantiomer or diastereomer, in enantiomeric or diastereomeric excess, as appropriate, from prochiral or chiral starting materials.Methods are available for the preparation of enantiomerically enriched amines. For example, the addition of organometallic reagents to imines or their derivatives is reported by Watanabe et al., . ...

PROCESS FOR OBTAINING PURE ANILINE

A process for obtaining pure aniline contains 1. A process for obtaining pure aniline , the process comprising:catalytic hydrogenation of catalytically hydrogenating nitrobenzene, to obtain a reaction mixture,optionally partially condensing the reaction mixture,separating the reaction mixture or the partially condensed reaction mixture into a gas phase comprising hydrogen and a liquid phase,liquid/liquid phase separating the liquid phase to obtain an aqueous phase which is passed to a further work-up or discharged and also crude aniline as an organic phase, where the crude aniline comprises 90-95% by weight of aniline, 4-9% by weight of water and a remainder comprising components having boiling points higher than that of aniline, in each case based on the total weight of the crude aniline, and the sum of the components of the crude aniline is 100% by weight,distillatively prepurifying the crude aniline by partially or completely removing the water via an overhead stream of a first distillation column to obtain a first bottom stream,feeding the first bottom stream as a feed stream to a pure column from which a pure aniline stream comprising at least 99.9% by weight of aniline, based on the total weight of the pure aniline stream, is taken off at the top and a second bottom stream comprising high boilers is taken off, wherein a proportion by weight of the second bottom stream is not more than 0.8%, based on the weight of the feed stream, andpassing the second bottom stream to incineration, by pumping the second bottom stream through one or more heated pipelines wherein a temperature of the second bottom stream is 45° C. or higher, and by adding methanol, ethanol, propanol, acetone or a mixture thereof to the second bottom stream in a proportion by weight of 5-30%, based on the weight of the second bottom stream.2. The process of claim 1 , comprising partially condensing the reaction mixture.3. The process of claim 1 , comprising adding methanol claim 1 , ethanol claim ...

PROCESS TO PREPARE HIGHER ETHYLENE AMINES AND ETHYLENE AMINE DERIVATIVES

The present invention relates to a process to prepare ethyleneamines of the formula NH—(CH—NH—)H wherein p is at least 3 or derivatives thereof wherein one or more units —NH—CH—NH— may be present as a cyclic ethylene urea unit or between two units —NH—CH—NH— a carbonyl moiety is present, by reacting an ethanolamine-functional compound, an amine-functional compound in the presence of a carbon oxide delivering agent, wherein the molar ratio of ethanolamine-functional compound to amine-functional compound is at least 0.7:1 and the molar ratio of carbon oxide delivering agent to amine-functional compound is at least 0.05:1. 2. Process of wherein the molar ratio of ethanolamine-functional compound to amine-functional compound is between 0.8 and 5:1 and the molar ratio of carbon oxide delivering agent to amine functional compound is between 0.2:1 and 20:1.3. Process of wherein the molar ratio of ethanolamine-functional compound to amine-functional compound is between 1:1 and 2:1 and the molar ratio of carbon oxide delivering agent to amine-functional compound is between 0.7:1 and 3:14. Process of wherein the ethanolamine-functional compound and the carbon oxide delivering agent are at least partly added as one compound by using a carbamate adduct.5. Process of wherein the amine-functional compound and the carbon oxide delivering agent are at least partly added as one compound by using an urea adduct.6. Process of wherein the ethanolamine-functional compound is of the formula OH—(CH—NH—)H wherein q is at least 1 and the amine-functional compound is of the formula NH—(CH—NH—)H wherein r is at least 1 claim 1 , wherein the sum of q+r is at least 3 and wherein optionally one or more q or r units may be present as a cyclic ethylene urea claim 1 , or cyclic ethylene carbamate unit.7. Process of wherein next a step is performed to convert the obtained cyclic ethylene urea into its corresponding ethylene amine.8. Process of wherein the ethanolamine-functional compound is AEEA ( ...

Efficient Continuous Process for Manufacturing of 4-Aminodiphenylamine From Aniline and Nitrobenzene

An efficient continuous manufacturing process for 4-aminodiphenylamine by coupling aniline with nitrobenzene in the presence of tetramethylammonium hydroxide (TMAH) as a base, using flow reactors wherein base decomposition is considerably reduced by optimizing base quantity, process conditions and process equipment. 1. A process comprising the step of:reacting aniline and nitrobenzene in the presence of TMAH as base and water in a continuous manner employing a series of continuous flow reactors under conditions suitable to produce at the flow reactors outlet a coupling reaction product including one or more TMA-salts of 4-NODPA and 4-NDPA along with one or more by-products including at least azobenzene, wherein a water to free TMAH molar ratio in the reaction product is at least about 3:1 and a water to total base ratio in the reaction product is less than 0.6:1.2. The process according to further comprising the step of adding water to the reaction product and then hydrogenating the reaction product with the added water in the presence of suitable hydrogenation catalyst to produce a 4-ADPA-containing reaction product;3. The process according to claim 2 , further comprising the steps of:separating the hydrogenation catalyst from the reaction mixture to obtain an aqueous phase containing base catalyst and an organic phase containing at least 4-ADPA, azobenzene and phenazine;purifying the organic phase under suitable conditions to obtain 4ADPA and recover excess aniline which is recycled as a reactant to the coupling step of the process; andpurifying the aqueous phase to regenerate TMAH base for recycle to the coupling step of the process.4. The process according to claim 1 , wherein a molar ratio of water to total TMAH is up to 10:1 at the start of the coupling reaction of aniline with nitrobenzene.5. The process according to claim 1 , wherein in the coupling step claim 1 , an initial molar ratio of aniline to nitrobenzene is from 6:1 to 15:1.6. The process according ...

ISOMERIZATION METHOD FOR CYCLOHEXANEDIAMINE

The present invention provides a method for isomerizing a cyclohexanediamine, which simply and highly actively realizes an isomerization reaction of a cyclohexanediamine, without passing through a high-pressure reaction and a complicated multi-stage process. The isomerization method has an isomerization step of isomerizing a cyclohexanediamine in the presence of a compound represented by the following formula (1) and at least one selected from the group consisting of an alkali metal, an alkali metal-containing compound, an alkaline earth metal or an alkaline earth metal-containing compound. 2. The method for isomerizing a cyclohexanediamine according to claim 1 , wherein the substituted or unsubstituted hydrocarbon group represented by each of Rand Rcomprises a monovalent group selected from the group consisting of a substituted or unsubstituted aliphatic hydrocarbon group claim 1 , a substituted or unsubstituted alicyclic hydrocarbon group and a substituted or unsubstituted aromatic hydrocarbon group; and{'sup': '3', 'the substituted or unsubstituted hydrocarbon group represented by Rcomprises an n-valent group selected from the group consisting of a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alicyclic hydrocarbon group and a substituted or unsubstituted aromatic hydrocarbon group.'}5. The method for isomerizing a cyclohexanediamine according to claim 1 , wherein the imine compound is obtained by dehydration condensation between a primary amine and an aldehyde and/or a ketone.6. The method for isomerizing a cyclohexanediamine according to claim 1 , wherein the imine compound is obtained by dehydration condensation between the cyclohexanediamine and an aldehyde and/or a ketone.7. The method for isomerizing a cyclohexanediamine according to claim 1 , wherein the cyclohexanediamine is 1 claim 1 ,4-cyclohexanediamine.8. The method for isomerizing a cyclohexanediamine according to claim 1 , wherein the alkali metal- ...

Isomerization method for 1,3,3-trimethyl-1-(aminomethyl)aminocyclohexane

An isomerization reaction of a predetermined compound, without passing through a high pressure reaction and a complicated multi-stage process. The isomerization method includes isomerizing, 1,3,3-trimethyl-1-(aminomethyl)aminocyclohexane in the presence of a compound represented by formula (1) and at least one compound selected from no alkali metal, an alkali metal-containing compound, an alkaline earth metal and an alkaline earth metal-containing compound: where R 1 and R 2 each independently represent a hydrogen atom or a monovalent group selected from a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group and an acyl group, R 1 and R 2 may mutually bind to form a ring, R 3 represents a hydrogen atom and an n-valent group selected from a substituted or unsubstituted hydrocarbon group, and n represents as integer of 1 to 10.

PROCESS TO CONVERT CYCLIC ALKYLENE UREAS INTO THEIR CORRESPONDING ALKYLENE AMINES

The present invention relates to a process to convert cyclic alkylene ureas into their corresponding alkylene amines wherein the process is performed by reaction with an amine compound, and wherein the amine compound comprises a primary amine, a cyclic secondary amine or a tertiary bicyclic amine. 2. Process of wherein the amine compound is a compound that can bind the carbonyl group from the cyclic alkylene urea to give another linear or cyclic alkylene urea or linear or cyclic alkylene carbamate.3. Process of wherein the amine compound is a smaller alkylene amine or alkanol amine than the one derived from the starting cyclic alkylene urea after the conversion.4. Process of wherein the amine compound is an alkylene amine or an alkanol amine compound that is larger than the one derived from the starting cyclic alkylene urea after the conversion.5. Process of wherein the amine compound is ethylenediamine (EDA) claim 3 , N-methylethylenediamine (MeEDA) claim 3 , diethylenetriamine (DETA) claim 3 , ethanolamine (MEA) claim 3 , aminoethylethanolamine (AEEA) claim 3 , piperazine (PIP) claim 3 , N-aminoethylpiperazine (AEP) claim 3 , N-diethyldiamine-2-imidazolidinone (U1TETA) claim 3 , N claim 3 ,N′-diaminoethylpiperazine (DAEP) claim 3 , N claim 3 ,N′-diaminoethyl-2-imidazolidinone (U2TETA) claim 3 , a polyethyleneimine (PEI) or an alkylene amine on a solid carrier.6. Process of wherein the reaction is done in the presence of a polar liquid claim 1 , preferably water.7. Process of wherein the amine compound is ethylenediamine (EDA) claim 1 , N-methylethylenediamine (MeEDA) claim 1 , diethylenetriamine (DETA) claim 1 , ethanolamine (MEA) claim 1 , aminoethylethanolamine (AEEA) claim 1 , piperazine (PIP) claim 1 , N-aminoethylpiperazine (AEP) claim 1 , 1 claim 1 ,4-diazabicyclo[2.2.2]octane (DABCO) claim 1 , 1 claim 1 ,4-diazabicyclo[2.2.2]octan-2-yl)methanol claim 1 , triethylenetetramine (TETA) claim 1 , N-diethyldiamine-2-imidazolidinone (U1TETA) claim 1 , N claim 1 ,N ...

METHOD FOR PREPARING SUBSTITUTED 4-AMINOINDANE DERIVATIVES

The present invention relates to a method for preparing substituted 4-aminoindane derivatives of the general formula (I) by cyclization, 2. Method according to claim 1 , wherein{'sub': 1', '4', '1', '4', '1', '4', '1', '4', '1', '4', '1', '4', '1', '4', '1', '4', '1', '4', '1', '4', '1', '4, 'R is mutually independently halogen, (C-C)alkyl, (C-C)alkoxy, (C-C)alkylphenyl, aryl, cyano(C-C)alkyl, halo(C-C)alkyl having 1-9 identical or different halogen atoms, (C-C)alkoxycarbonyl(C-C)alkyl, (C-C)alkoxy(C-C)alkyl or halo(C-C)alkoxy(C-C)alkyl,'}n is an integer from 0 to 3,{'sup': 1', '2', '3', '4, 'sub': 1', '4', '1', '4', '1', '4', '1', '4', '1', '4', '1', '4', '1', '4', '1', '4, 'R, R, Rand Rare mutually independently hydrogen, (C-C)alkyl, (C-C)alkylphenyl, (C-C)alkoxy, aryl, cyano(C-C)alkyl, (C-C)alkoxycarbonyl(C-C)alkyl or (C-C)alkoxy(C-C)alkyl and'}{'sup': 1', '2, 'sub': 1', '4', '1', '4', '1', '4, 'Qand Qare mutually independently hydrogen, substituted (C-C)alkylsulphonyl, substituted alkoxycarbonyl(C-C)alkyl or substituted (C-C)haloalkylsulphonyl.'}3. Method according to claim 1 , whereinR is mutually independently fluorine, chlorine, bromine, methyl or trifluoromethyl,n is an integer from 0 to 1,{'sup': 1', '2', '3', '4, 'R, R, Rand Rare mutually independently hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl and'}{'sup': 1', '2, 'sub': 1', '4', '1', '3', '1', '3, 'Qand Qare mutually independently hydrogen, substituted (C-C)alkylsulphonyl, substituted alkoxycarbonyl(C-C)alkyl or substituted (C-C)haloalkylsulphonyl.'}4. Method according to claim 1 , whereinn is 0 orR is fluorine and n is 1, wherein fluorine is optionally in the 5-, 6- or 7-position, optionally in the 6- or 7-position and optionally in the 7-position of the indane residue, orR is trifluoromethyl and n is 1, wherein trifluoromethyl is optionally in the 5-, 6- or 7-position, optionally in the 6- or 7-position and optionally in the 7-position of the indane residue ...

PROCESS FOR PREPARING 4-AMINODIPHENYLAMINE

A process for preparing 4-aminodiphenylamine (4-ADPA) comprising steps of coupling of aniline with nitrobenzene in presence of a suitable base, e.g. tetramethylammonium hydroxide (TMAH), hydrogenation of the coupling mass, phase separation, hydrogenation of azobenzene in the separated organic mass and fractional distillation for 4-ADPA recovery. An improvement in 4-ADPA recovery and a lowering of tar formation are obtained due to azobenzene reduction prior to 4-ADPA isolation. Also a gain in volume productivity of 4-ADPA is obtained by suitably altering the batch cycle time of the coupling reaction. 1. A process for preparing and isolating 4-aminodiphenylamine comprising the steps of:i) reacting aniline and nitrobenzene in the presence of a base catalyst and water under conditions suitable to produce a reaction product comprising one or more salts of 4-nitrosodiphenylamine and 4-nitrodiphenylamine along with one or more by-products comprising at least azobenzene;ii) adding water and hydrogenating the reaction product from step i) in the presence of suitable hydrogenation catalyst to produce 4-aminodiphenylamine-containing reaction product;iii) separating the hydrogenation catalyst from the reaction mixture by filtration or any other suitable technique to obtain an aqueous phase containing at least base catalyst and an amount of organics, and an organic phase containing at least 4-aminodiphenylamine, azobenzene and base catalyst; andiv) washing organic phase with water to reduce an amount of residual base catalyst in the organic phase and/or extracting the aqueous phase with an aromatic hydrocarbon solvent to reduce an amount of organics present in said aqueous phase.2. The process according to claim 1 , wherein step (iv) comprises washing organic phase with water to reduce an amount of residual base catalyst in the organic phase.3. The process according to claim 1 , wherein step (iv) comprises extracting the aqueous phase with an aromatic hydrocarbon solvent to ...

METHOD FOR ISOMERIZING BIS(AMINOMETHYL)CYCLOHEXANE

A method for isomerizing a bis(aminomethyl)cyclohexane, including isomerizing a bis(aminomethyl)cyclohexane while introducing an inert gas in a reaction solution containing 1. A method for isomerizing a bis(aminomethyl)cyclohexane , the method comprising isomerizing a bis(aminomethyl)cyclohexane while introducing an inert gas in a reaction solution comprising:a bis(aminomethyl)cyclohexane,at least one selected from the group consisting of an alkali metal, an alkali metal-containing compound, an alkaline earth metal and an alkaline earth metal-containing compound, anda benzylamine compound.2. The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1 , wherein the inert gas is at least one selected from the group consisting of helium claim 1 , argon and nitrogen.3. The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1 , wherein the benzylamine compound is at least one selected from the group consisting of benzylamine claim 1 , 3-methylbenzylamine claim 1 , 4-methylbenzylamine claim 1 , dibenzylamine claim 1 , meta-xylylenediamine and para-xylylenediamine.4. The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1 , wherein the benzylamine compound is 4-methylbenzylamine.5. The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1 , wherein the reaction solution comprises an alkali metal-containing compound claim 1 , which comprises sodium amide.6. The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1 , wherein an isomerization reaction temperature is 100 to 140° C.7. The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1 , wherein the introducing of the inert gas comprises bubbling.8. The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1 , wherein the bis(aminomethyl)cyclohexane is 1 claim 1 ,4-bis(aminomethyl)cyclohexane.9. The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1 , wherein the ...

PROCESS FOR PRODUCING AN AMINOPROPYNE OR ENAMINONE

There is provided a process for producing an aminopropyne or an enaminone comprising the step of reacting a metal acetylide, an amine and a carbonyl-containing compound in the presence of a transition metal catalyst. There is also provided a process for producing an aminopropyne comprising the step of reacting a metal acetylide, an amine and a halide-containing compound in the presence of a transition metal catalyst at a reaction temperature of 50° C. to 150° C. There are also provided processes to further synthesize the aminopropyne produced to obtain a butyneamine, another aminopropyne or a triazol. 1. A process for producing an aminopropyne comprising the step of reacting a metal acetylide , an amine and a halide-containing compound in the presence of a transition metal catalyst at a reaction temperature of 50° C. to 150° C.2. The process as claimed in claim 1 , wherein said halide-containing compound is C-haloalkane. This application is a divisional application of and claims the benefit of priority to U.S. patent application Ser. No. 14/131,083, filed on Jan. 6, 2014, which is a U.S. national stage application under 35 U.S.C. §371 of PCT/SG2012/000240, filed Jul. 6, 2012, and published as WO 2013/006143 A1 on Jan. 10, 2013, which claims priority to Singapore Application No. 201104950-9, filed Jul. 6, 2011, which applications and publication are incorporated by reference as if reproduced herein and made a part hereof in their entirety, and the benefit of priority of each of which is claimed herein.The present invention generally relates to a three component coupling reaction to produce aminopropynes. The present invention also relates to a three component coupling reaction to produce enaminones.Proparglyamines are frequent skeletons and synthetically-versatile key intermediates for the preparation of many nitrogen-containing biologically active compounds. In recent years, the most useful methods for synthesis of aminopropynes include using very sensitive Grignard ...

Process for preparing aromatic amines

The invention relates to a process for the continuous preparation of aromatic amines by hydrogenation of the corresponding nitroaromatics in the presence of catalysts arranged in reaction spaces, in which an adiabatically operated reaction space RA is connected downstream of an isothermally operated reaction space RI and RA additionally also has a separate feed for the nitroaromatic to be hydrogenated, RI is fed with the nitroaromatic to be hydrogenated from the start to the end of the hydrogenation, and the product mixture emerging from RI is fed into RA from the start to the end of the hydrogenation, wherein RA can additionally be fed via the separate feed with the nitroaromatic to be hydrogenated.

ISOMERIZATION METHOD FOR DIAMINODICYCLOHEXYLMETHANE

An object of the present invention is to simply and highly actively realize an isomerization reaction of an industrially important compound, diaminodicyclohexylmethane, without passing through a complicated multi-stage process. 2: The method for isomerizing a diaminodicyclohexylmethane according to claim 1 , wherein{'sup': 1', '2, 'the substituted or unsubstituted hydrocarbon group represented by each of Rand Rcomprises a monovalent group selected from the group consisting of a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alicyclic hydrocarbon group and a substituted or unsubstituted aromatic hydrocarbon group; and'}{'sup': '3', 'the substituted or unsubstituted hydrocarbon group represented by Rcomprises an n-valent group selected from the group consisting of a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alicyclic hydrocarbon group and a substituted or unsubstituted aromatic hydrocarbon group.'}5: The method for isomerizing a diaminodicyclohexylmethane according to claim 1 , wherein the imine compound is obtained by dehydration condensation between a primary amine and an aldehyde and/or a ketone.6: The method of isomerizing a diaminodicyclohexylmethane according to claim 1 , wherein the imine compound is obtained by dehydration condensation between the diaminodicyclohexylmethane and an aldehyde and/or a ketone.7: The method for isomerizing a diaminodicyclohexylmethane according to claim 1 , wherein the diaminodicyclohexylmethane is 4 claim 1 ,4′-diaminodicyclohexylmethane.8: The method for isomerizing a diaminodicyclohexylmethane according to claim 1 , wherein the alkali metal-containing compound comprises at least one selected from the group consisting of an alkali metal hydride and an alkali metal amide.9: The method for isomerizing a diaminodicyclohexylmethane according to claim 1 , wherein an isomerization reaction temperature in the isomerizing is 100 to 140° C.10: The ...

METHOD FOR PREPARING TETRAMETHYLAMMONIUM FLUORIDE

A method for the preparation of anhydrous, alcohol-free tetramethylammonium fluoride is described. The method includes fluorination of tetramethylammonium chloride with potassium fluoride in an alcohol solvent, removal of insoluble potassium salts, and finally, removal of the alcohol solvent and replacement of it with an aprotic solvent. 1. A method for preparing anhydrous , alcohol-free tetramethylammonium fluoride which comprises:a) mixing together tetramethylammonium chloride, potassium fluoride and an alcohol solvent;b) isolating tetramethylammonium fluoride from the mixture as a solution in the alcohol solvent;c) adding an aprotic solvent to the mixture containing the tetramethylammonium fluoride as a solution in the alcohol solvent; andd) removing the alcohol solvent.2. The method of in which the alcohol solvent is selected from the group including methanol claim 1 , ethanol claim 1 , and 2-propanol.3. The method of in which the tetramethylammonium fluoride as a solution in the alcohol solvent is isolated by removing insoluble potassium salts from the first mixture.4. The method of in which the removing insoluble potassium salts is conducted by filtration or centrifugation.5. The method of in which the aprotic solvent may be selected from the group including N claim 1 ,N-dimethylformamide (DMF) claim 1 , N claim 1 ,N-dimethylacetamide (DMA) claim 1 , sulfolane claim 1 , 2-methyl tetrahydrofuran claim 1 , N-methyl-2-pyrrolidone claim 1 , dimethyl sulfoxide claim 1 , tetrahydrofuran claim 1 , cyclopentyl methyl ether claim 1 , ethylene carbonate claim 1 , propylene carbonate claim 1 , dioxane claim 1 , mono- and diethyleneglycol ethers claim 1 , and mono- and dipropyleneglycol ethers.6. The method of in which the alcohol solvent is removed by distillation.7. The method of in which the distillation is a vacuum distillation.8. An anhydrous claim 1 , alcohol-free composition of tetramethylammonium fluoride in an aprotic solvent prepared by the method of .9. The ...

PROCESS FOR PREPARATION OF TERTIARY ALKYL PRIMARY AMINES

A method for producing an amine. The first step is contacting a cyanide, an acid, water and a substrate compound capable of generating a carbonium ion by reaction with the acid to generate a first reaction intermediate. The second step is contacting the first reaction intermediate with water to form a second reaction intermediate. The third step is removing cyanide present in the second reaction intermediate to a concentration less than 10 ppm. The fourth step is contacting the second reaction intermediate with an alkali metal hydroxide to form the amine 1. A method for producing an amine; said method comprising steps of: (a) contacting hydrogen cyanide or a salt thereof , an acid , water and a substrate compound capable of generating a carbonium ion by reaction with the acid to generate a first reaction intermediate; (b) contacting the first reaction intermediate with water to form a second reaction intermediate; (c) removing cyanide present in the second reaction intermediate to a concentration less than 10 ppm; and (d) contacting the second reaction intermediate with an alkali metal hydroxide to form the amine.2. The method of in which the substrate compound is an alkene oligomer.3. The method of in which the acid is an inorganic acid.4. The method of in which the alkali metal hydroxide is sodium hydroxide or potassium hydroxide.5. The method of in which hydrogen cyanide is removed from the second reaction intermediate by a stripper column.6. The method of in which the alkene oligomer is propylene tetramer claim 5 , propylene hexamer or isobutylene dimer.7. The method of in which the inorganic acid is a concentrated aqueous solution of sulfuric acid that includes from about 60 wt % to about 100 wt % sulfuric acid.8. The method of in which hydrogen cyanide removed from the second reaction intermediate is recycled to step (a). This invention relates to a method for preparation of tertiary alkyl primary amine compounds with reduced waste costs.Methods for ...

MONONUCLEAR RUTHENIUM COMPLEX AND ORGANIC SYNTHESIS REACTION USING SAME

A neutral or cationic mononuclear ruthenium divalent complex represented by formula (1) can actualize exceptional catalytic activity in at least one reaction among a hydrosilylation reaction, hydrogenation reaction, and carbonyl compound reduction reaction. 2. The neutral or cationic mononuclear divalent ruthenium complex of claim 1 , wherein L is at least one type of two-electron ligand selected from the group consisting of molecular hydrogen claim 1 , amines claim 1 , imines claim 1 , nitrogen-containing heterocycles claim 1 , phosphines claim 1 , phosphites claim 1 , arsines claim 1 , alcohols claim 1 , thiols claim 1 , ethers claim 1 , sulfides claim 1 , nitriles claim 1 , isonitriles claim 1 , aldehydes claim 1 , ketones claim 1 , alkenes of 2 to carbon atoms claim 1 , alkynes of 2 to 30 carbon atoms and triorganohydrosilanes.4. The neutral or cationic mononuclear divalent ruthenium complex of claim 3 , wherein Lis at least one type of two-electron ligand selected from the group consisting of isonitriles claim 3 , nitrogen-containing heterocycles and phosphites (with the proviso that when a plurality of Lligands are present claim 3 , two Lligands may be bonded to one another).5. The neutral or cationic mononuclear divalent ruthenium complex of or claim 3 , wherein Lis a triorganohydrosilane (with the proviso that when a plurality of Lligands are present claim 3 , two Lligands may be bonded to one another).6. The neutral or cationic mononuclear divalent ruthenium complex of claim 3 , wherein mand mare both 2.7. The neutral or cationic mononuclear divalent ruthenium complex of claim 6 , wherein Rto Rare each independently an alkyl claim 6 , aryl or aralkyl group that may be substituted with X claim 6 , which is as defined above claim 6 , and{'sup': 2', '7', '8', '9', '10', '11', '12', '7', '12, 'the Lligands are triorganohydrosilanes of the formulas H—SiRRRand H—SiRRR(wherein Rto Rare each independently an alkyl, aryl or aralkyl group that may be substituted with ...

Chemical Installation

According to the present invention, a chemical installation is provided. The chemical installation comprises 1. A method for producing DADPM , the method comprisesconverting benzene into nitrobenzene thereby providing a nitrobenzene stream and a first aqueous waste stream comprising nitrobenzene;converting said nitrobenzene from said nitrobenzene stream into aniline, thereby providing an aniline stream and a first part of a second aqueous waste stream comprising aniline;removing nitrobenzene from said aniline prior to converting said aniline from said aniline stream into DADPM;converting said aniline from said aniline stream into DADPM thereby providing a second part of said second aqueous waste stream comprising aniline;stripping aniline and nitrobenzene from said first and second aqueous waste stream by means of a stripping column;providing the stripped aniline and nitrobenzene to said aniline cleaning apparatus or to said nitrobenzene stream.2. The method for producing DADPM according to claim 1 , wherein the said aniline production unit comprises a reactor for converting said nitrobenzene into aniline claim 1 , the converting said nitrobenzene from said nitrobenzene stream into aniline comprisesproviding said stripped aniline and nitrobenzene to said reactor for converting said nitrobenzene into aniline;converting nitrobenzene into aniline in a reactor; andremoving nitrobenzene from the provided aniline using an aniline cleaning apparatus.3. The method for producing DADPM according to claim 1 , wherein the said aniline production unit comprises a reactor for converting said nitrobenzene into aniline claim 1 , the converting said nitrobenzene from said nitrobenzene stream into aniline comprisesconverting nitrobenzene into aniline in said reactor;providing said stripped aniline and nitrobenzene to said aniline obtained as reactor effluent; andremoving nitrobenzene from the aniline using an aniline cleaning apparatus.4. The method for producing DADPM according to ...

ORGANIC SYNTHESIS APPLICATIONS OF NON-AQUEOUS FLUORIDE SALT SOLUTIONS

Processes and reaction mixtures including non-aqueous solvent mixtures are presented. Non-aqueous solvent mixtures including fluoride salt and non-aqueous solvent combinations are provided that possess high fluoride ion concentrations useful for a range of applications, including organic synthesis. Further non-aqueous solvent mixtures are provided including a salt possessing a non-fluoride anion and a non-aqueous solvent that, when contacted with aqueous fluoride-containing reagents, extract fluoride ions to form non-aqueous fluoride-ion solutions possessing high fluoride-ion concentrations. The salts include an organic cation that does not possess a carbon in the β-position or does not possess a carbon in the β-position having a bound hydrogen. This salt structure facilitates its ability to be made anhydrous without decomposition. Example anhydrous fluoride salts include (2,2-dimethylpropyl)trimethylammonium fluoride and bis(2,2-dimethylpropyl)dimethylammonium fluoride. The combination of these fluoride salts with at least one fluorine-containing non-aqueous solvent (e.g., bis(2,2,2-trifluoroethyl)ether; (BTFE)) promotes solubility of the salt within the non-aqueous solvents. 1. A process for chemical synthesis , comprising:contacting one or more reagents with a non-aqueous solvent mixture comprising:a fluoride salt, comprising:one or more fluoride ions; andan organic cation that does not possess a carbon in the β-position or does not possess a carbon in the β-position having a bound hydrogen, wherein the cation charge center is N, P, S, or O; andone or more non-aqueous solvent;wherein a concentration of said fluoride ions dissolved in said non-aqueous solvent mixture is greater than or equal to 0.05 M.2. A process for solvent extraction , comprising:contacting an aqueous fluoride ion-containing reagent with a non-aqueous solvent mixture, wherein the non-aqueous solvent mixture comprises:one or more non-aqueous solvent; anda salt, comprising:a non-fluoride anion ...

3-AMINOMETHYL-3, 5, 5-TRIMETHYL CYCLOHEXYLAMINE PREPARATION METHOD

Provided is a 3-aminomethyl-3,5,5-trimethylcyclohexylamine preparation method. A feeding flow of 3-cyano-3,5,5-trimethylcyclohexylimine is reacted with NH3 and hydrogen in the presence of a hydrogenation catalyst; the method is characterized by: firstly adding a basic compound to the feeding flow of 3-cyano-3,5,5-trimethylcyclohexylimine, and then after a portion of 3-cyano-3,5,5-trimethylcyclohexylimine has reacted, adding an acidic compound to reaction materials for further hydrogenation reaction to prepare the product. The method ensures that the aminonitrile content in the product is low, thus effectively reducing the duration of the reaction and greatly reducing the consumption of the catalyst during the hydrogenation reaction process. 1. A method for preparing 3-aminomethyl-3 ,5 ,5-trimethyl-cyclohexylamine , the method comprising:{'sub': '3', 'a) reacting 3-cyano-3,5,5-trimethyl-cyclohexanone with NHto obtain a product containing 3-cyano-3,5,5-trimethyl-cyclohexylimine;'}{'sub': '3', 'b) mixing the product of step a) with a basic compound in the presence of hydrogen, NHand a first hydrogenation catalyst to obtain a product containing 3-aminomethyl-3,5,5-trimethyl-cyclohexylamine and 3-cyano-3,5,5-trimethyl-cyclohexylamine, wherein the space velocity on the first hydrogenation catalyst is 0.5-10 g of 3-cyano-3,5,5-trimethyl-cyclohexanone/(per ml catalyst per hour), preferably 1-5 g of 3-cyano-3,5,5-trimethyl-cyclohexanone/(per ml catalyst per hour), more preferably 1.5-2 g of 3-cyano-3,5,5-trimethyl-cyclohexanone/(per ml catalyst per hour);'}{'sub': '3', 'c) mixing the product of step b) with an acidic compound in the presence of hydrogen, NHand a second hydrogenation catalyst, wherein the 3-cyano-3,5,5-trimethyl-cyclohexylamine in the product of step b) is converted into 3-aminomethyl-ethyl-cyclohexylamine.'}2. The method according to claim 1 , wherein the content of 3-cyano-3 claim 1 ,5 claim 1 ,5-trimethyl-cyclohexylamine in the product of step b) is 5-20 ...

METHOD FOR STARTING A REACTION DURING THE PRODUCTION OF AROMATIC AMINES FROM NITROAROMATICS

The present invention relates to a method of producing aromatic amines by hydrogenation of aromatic nitro compounds. This method comprises the steps: 1. A process for preparing aromatic amines by hydrogenation of aromatic nitro compounds , which comprises:A) providing a reactor with hydrogenation catalyst present therein;B) introducing aromatic nitro compounds and hydrogen into said reactor contacting with said hydrogenation catalyst, wherein at least said hydrogen is fed into the reactor by means of a compressor and said compressor contains an operating liquid which at least partially contacts said hydrogen;C) regenerating said hydrogenation catalyst by heating and contacting with oxygen;wherein:{'b': '1', 'D) at least partially removing liquids which are present in said reactor and/or in plant parts fluidically connected downstream to said reactor and which were at least partly present in said reactor and/or in said plant parts during step C);'}and/or:D2) at least partially replacing said operating liquid of said compressor which was present in said compressor and/or in recirculation facilities connected to said compressor during step C) by an operating liquid which was not present in said compressor and/or in recirculation facilities connected to said compressor during step C);are carried out after C).2. The process as claimed in claim 1 , wherein said compressor is a liquid ring compressor.3. The process as claimed in claim 1 , wherein said operating liquid in said compressor is water or an aqueous solution containing more than 90% by weight of water.4. The process as claimed in claim 1 , wherein said reactor is additionally filled or flushed with an inert gas after step C).51. The process as claimed in claim 1 , wherein step D) is carried out by flushing said reactor and/or plant parts fluidically connected downstream to said reactor with water and/or an aqueous solution containing more than 90% by weight of water.6. The process as claimed in claim 1 , wherein ...

METHOD FOR COUPLING A FIRST COMPOUND TO A SECOND COMPOUND

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an amine; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture including a base, the base comprising a carbonate salt, a phosphate salt or an acetate salt, the reaction mixture under conditions effective to couple the first compound to the second compound. The present disclosure further describes a one-pot method for coupling a first compound to a second compound in the presence of a mild base. 1. A method of coupling a first compound to a second compound , method comprising:providing the first compound having a fluorosulfonate substituent, the first compound comprising an aryl or a heteroaryl group;providing the second compound comprising an amine; andreacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture including a base, the base comprising a carbonate salt, a phosphate salt or an acetate salt, the reaction mixture under conditions effective to couple the first compound to the second compound.2. The method of claim 1 , wherein the reaction mixture further includes a ligand.3. The method of wherein the catalyst is generated in-situ from a palladium precatalyst.4. The method of wherein the catalyst is generated in-situ from a palladium precatalyst claim 1 , the palladium precatalyst is selected from the group consisting of: Palladium(II) acetate claim 1 , Palladium(II) chloride claim 1 , Dichlorobis(acetonitrile)palladium(II) claim 1 , Dichlorobis(benzonitrile)palladium(I1) claim 1 , Allylpalladium chloride dimer claim 1 , Palladium(II) acetylacetonate claim 1 , Palladium(II) bromideBis(dibenzylideneacetone) ...

METHOD FOR STOPPING A REACTION DURING THE PRODUCTION OF AROMATIC AMINES FROM NITROAROMATICS

The present invention relates to A method for producing aromatic amines by the hydrogenation of aromatic nitro compounds. This method comprises: 2. The process as claimed in claim 1 , wherein said hydrogen gas is circulated through said reactor in step B1).3. The process as claimed in wherein the amount of aromatic nitro compounds and hydrogen is reduced in each case to from ≧1% by mass to ≦40% by mass of the amount introduced previously in step A) before step B).4. The process as claimed in claim 1 , wherein said reactor is filled with an inert gas after step B).5. The process as claimed in claim 1 , wherein step A) is carried out isothermally.6. The process as claimed in claim 1 , wherein the molecular ratio of hydrogen to nitro groups of said aromatic nitro compounds in step A) is from ≧3:1 to ≦6:1.7. The process as claimed in claim 1 , wherein said predetermined time in step B2) is ≧1 hour.8. The process as claimed in claim 1 , wherein the predetermined concentration of aromatic nitro compounds said gas stream entering said reactor in step B2) is less than 1000 ppm.10. The process as claimed in claim 1 , wherein said catalyst is arranged in as fixed catalyst bed in said reactor. The present invention relates to a process for preparing aromatic amines by hydrogenation of aromatic nitro compounds, which comprises the steps of introduction of aromatic nitro compounds and hydrogen into a reactor with contacting of a hydrogenation catalyst and of stopping the introduction of aromatic nitro compounds and hydrogen into the reactor.Aromatic amines are important intermediates which have to be prepared inexpensively and in large amounts. For this reason, production plants for aromatic amines are generally built for very high capacities, The high productivity of these plants is ensured by means of very long reaction cycles and trouble-free running between the start-up and shutdown operations of the hydrogenation for regeneration of the hydrogenation catalysts used.Aniline ...

Method for Preparting Alkylamines

The present invention relates to a method for preparing alkylamines using carbon monoxide and the use of this method in the manufacturing of vitamins, pharmaceutical products, adhesives, acrylic fibres and synthetic leathers, pesticides, surfactants, detergents and fertilisers. 2. The method according to claim 1 , wherein{'sup': 1', '2', '3, 'R, Rand Rrepresent, independently of each other, a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, a heterocycle, said alkyl, aryl, heteroaryl, heterocycle groups being optionally substituted;'}m, m′ and m″ are integers chosen from 0 and 1;q, q′, q″ are integers chosen from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10;n=0.3. The method according to claim 1 , wherein{'sup': 1', '2, 'Rand R, taken together with the nitrogen atom to which they are bound, form a heterocycle, optionally substituted, and'}{'sup': '3', 'Rrepresents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, a heterocycle, said alkyl, aryl, heteroaryl, heterocycle groups optionally being substituted;'}m, m′ and m″ are integers chosen from 0 and 1;q, q′, q″ are integers chosen from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10;n=0.4. The method according to claim 1 , wherein{'sup': 1', '2', '3, 'R, Rand Rrepresent, independently of each other, a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, a heterocycle, said alkyl, aryl, heteroaryl, heterocycle groups being optionally substituted;'}R represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, a heterocycle, said alkyl, aryl, heteroaryl, heterocycle groups being optionally substituted;m, m′ and m″ are integers chosen from 0 and 1;q, q′, q″ are integers chosen from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10;n=1;X represents a halogen atom, trifluoromethylsulfonate (triflate), methanesulfonate (mesylate), p-toluenesulfonic acid (tosylate).5. The method according to claim 1 , wherein{'sup': 1', '2, 'Rand R, taken together with the nitrogen atom to which they are ...

PRODUCTION METHOD FOR 2-ALKENYLAMINE COMPOUND

Provided is a method for producing a 2-alkenylamine compound efficiently and at low cost, using a primary or secondary amine compound and a 2-alkenyl compound as the starting materials therefor. The 2-alkenylamine compound is produced by adding Bronsted acid when 2-alkenylating by reacting the primary or secondary amine compound with the 2-alkenyl compound, and 2-alkenylating in the presence of a catalyst comprising a complexing agent and a transition metal precursor stabilized by a monovalent anionic five-membered conjugated diene. 1. A method for producing a 2-alkenylamine compound by reacting a primary or secondary amine compound with a 2-alkenyl compound in the presence of a catalyst ,wherein the catalyst is a transition metal complex which is a reaction product of a complexing agent having a nitrogen coordination site and an oxygen coordination site bidentate-coordinated to a transition metal atom in the molecule and a transition metal precursor having a monovalent anionic five-membered ring-conjugated diene as a ligand in the molecule, and wherein a Bronsted acid is added.3. The method for producing a 2-alkenylamine compound according to claim 1 , wherein the transition metal precursor comprises at least one of transition metal atoms selected from the group consisting of the transition metals belonging to Group 8 and Group 9 of the periodic table.4. The method for producing a 2-alkenylamine compound according to the claim 3 , wherein the transition metal atom is selected from the group consisting of ruthenium claim 3 , rhodium claim 3 , and iridium.7. The method for producing a 2-alkenylamine compound according to claim 6 , wherein all of R claim 6 , R claim 6 , R claim 6 , Rand Rin formula (1) each are a hydrogen atom.8. The method for producing a 2-alkenylamine compound according to claim 1 , wherein the primary or secondary amine compound is selected from the group consisting of a saturated C1 to C30 aliphatic amine having one or two amino group(s) in the ...

METHOD OF PRODUCING DIAMINES AND POLYAMINES OF THE DIPHENYLMETHANE SERIES

The invention relates to a method for producing diamines and polyamines of the diphenylmethane series, by condensing aniline and formaldehyde followed by an acid-catalysed rearrangement at different production capacities with alteration of the isomer composition in the resulting diamines of the diphenylmethane series (altering the 2,4′-MDA content). Adapting the molar ratios of the total used aniline to the total used formaldehyde and of the total used acid catalyst to the total used aniline, and adapting the reaction temperature, allows the rearrangement reaction to be fully completed despite the change in dwell time inevitably associated with a change in production capacity, and allows the formation of undesired by-products to be avoided as far as possible; the intended modification to binuclear content is likewise achieved. 2. The process of claim 1 , in which the temperature in the reactors of the reactor cascade 3000 increases from reactor 3000-1 to reactor 3000-i in all states of operation (A claim 1 , T claim 1 , E).3. The process of claim 1 , in which it is always the case that{'sub': '3000-1', 'Tis set to a value in the range from 25.0° C. to 65.0° C. and'}the temperature in each of the reactors downstream in flow direction (3000-2, . . . , 3000-i) is set to a value in the range from 35.0° C. to 200.0° C.4. The process of claim 3 , in which it is always the case that{'sub': '3000-1', 'Tis set to a value in the range from 30.0° C. to 60.0° C. and'}the temperature in each of the reactors downstream in flow direction (3000-2, . . . , 3000-i) is set to a value in the range from 50.0° C. to 180.0° C.5. The process of claim 1 , in which the acidic catalyst (7) is a mineral acid.6. The process of claim 1 , in which step (B) further comprises:(B-III) washing the organic phase (11) with washing liquid (13);(B-IV) separating the mixture (14) obtained in step (B-III) into an organic phase (16) comprising di- and polyamines of the diphenylmethane series and an aqueous ...

FIXED BED PROCESS FOR CLAY CATALYZED ALKYLATION OF AROMATIC AMINES

Aromatic amines, for example, diarylamines such as diphenylamine, dinaphthylamine, N-phenyl-N-naphthyl amine etc., are alkylated by passing a mixture of the amine and an olefin, though a clay catalyst in a fixed bed reactor system. The process is conveniently run as a continued process, produces an alkylated aromatic amine in excellent purity and provides efficiencies in material and energy use. 1. A process for alkylating an aromatic amine comprising:a) loading a fixed bed reactor with an acidic clay,b) heating or cooling the reactor to within a selected temperature range,{'sub': '3-20', 'claim-text': [{'br': None, 'sub': '2', 'ArNH,'}, {'br': None, 'sub': '2', 'ArNH,'}, {'br': None, 'sub': '3', 'ArN'}, {'br': None, 'or'}, {'br': None, 'sub': 2', '2, 'RN—Ar—NR,'}], 'c) passing through the acidic clay in the fixed bed reactor a mixture comprising one or more olefins selected from the group of Colefins, and an aromatic amine of formula{'sub': 1-18', '1-18, 'wherein each Ar is independently selected from the group consisting of phenyl, phenyl substituted by Calkyl, naphthyl, and naphthyl substituted by Calkyl;'}and{'sub': 1-18', '1-18', '1-18, 'each R is independently selected from the group consisting of H, Calkyl, phenyl, phenyl substituted by Calkyl, naphthyl, and naphthyl substituted by Calkyl;'}{'sub': '3-20', 'to yield a product wherein one or more of the groups Ar are alkylated by one or more alkyl groups derived from the Colefin.'}2. The process according to wherein the aromatic amine is of the formula ArNH.3. The process according to wherein the aromatic amine is diphenylamine claim 2 , dinaphthylamine or N-phenyl-N-naphthyl amine.4. The process according to wherein the one or more olefins comprises Colefins.5. The process according to wherein the one or more olefins comprise isobutylene claim 1 , di-isobutylene claim 1 , tri-isobutylene claim 1 , di-propylene claim 1 , tri-propylene or tetra-propylene.6. The process according to wherein the acidic clay is a ...

Supported Metal Catalysts

The present invention relates to supported metal catalysts, wherein the catalysts are modified by at least one amine, a method for the preparation thereof and hydrogenation processes utilising the supported metal catalysts. 2. The supported metal catalyst of claim 1 , wherein the support is carbon claim 1 , alumina claim 1 , calcium carbonate claim 1 , titania claim 1 , silica claim 1 , zirconia claim 1 , ceria claim 1 , or a combination thereof.3. The supported metal catalyst of claim 2 , wherein the alumina is alpha-AlO claim 2 , beta-AlO claim 2 , gamma-AlO claim 2 , delta-AlO claim 2 , theta-AlOor a combination thereof.4. The supported metal catalyst of claim 2 , wherein the carbon is activated carbon claim 2 , carbon black claim 2 , graphite claim 2 , or a combination thereof.5. (canceled)6. (canceled)7. The supported metal catalyst of claim 1 , wherein the metal is ruthenium claim 1 , rhodium claim 1 , palladium claim 1 , osmium claim 1 , iridium claim 1 , platinum claim 1 , gold claim 1 , silver claim 1 , copper claim 1 , iron claim 1 , cobalt claim 1 , nickel claim 1 , or a combination thereof.8. The supported metal catalyst of claim 1 , wherein the metal is palladium claim 1 , platinum claim 1 , gold claim 1 , or a combination thereof.9. The supported metal catalyst of claim 1 , wherein the Group VIII or IB metal is present in a range of from 0.01 wt % to 20 wt % claim 1 , relative to the total weight of the supported metal catalyst.10. The supported metal catalyst of claim 1 , wherein the amine is a natural amino acid claim 1 , non-natural amino acid claim 1 , peptide claim 1 , alkylamine claim 1 , alkyldiamine claim 1 , alkylpolyamine claim 1 , or combinations thereof.11. The supported metal catalyst of claim 10 , wherein the amine is lysine claim 10 , glycine claim 10 , proline claim 10 , alanine claim 10 , serine claim 10 , phenylalanine claim 10 , asparagine claim 10 , aspartic acid claim 10 , valine claim 10 , butylamine claim 10 , 6-aminocaproic acid ...

PRODUCTION METHOD FOR 2-ALKENYLAMINE COMPOUND

Provided is a method for producing a 2-alkenylamine compound efficiently and at low cost, using a primary or secondary amine compound and a 2-alkenyl compound as the starting materials therefor. The 2-alkenyleamine compound is produced by 2-alkenylating a primary or secondary amine compound, using a specified 2-alkenylating agent and in the presence of a catalyst comprising a complexing agent and a transition metal precursor stabilized by a monovalent anionic five-membered conjugated diene. 3. The method for producing a 2-alkenylamine compound according to claim 1 , wherein the transition metal precursor comprises at least one of transition metal atoms selected from the group consisting of the transition metals belonging to Group 8 and Group 9 of the periodic table.4. The method for producing a 2-alkenylamine compound according to claim 3 , wherein the transition metal atom is selected from the group consisting of ruthenium claim 3 , rhodium claim 3 , and iridium.6. The method for producing a 2-alkenylamine compound according to claim 1 , wherein all of R claim 1 , R claim 1 , R claim 1 , Rand Rin formula (1) each are a hydrogen atom.7. The method for producing a 2-alkenylamine compound according to claim 1 , wherein the primary or secondary amine compound is selected from the group consisting of a saturated C1 to C30 aliphatic amine having one or two amino group(s) in the molecule claim 1 , a saturated C3 to C30 alicyclic amine having one or two amino group(s) in the molecule claim 1 , a C6 to C30 arylamine compound having 1 to 10 amino group(s) in the molecule claim 1 , and a nitrogen-containing C2 to C30 heterocyclic compound having a hydrogen atom on the nitrogen atom constituting the heterocyclic ring.8. The method for producing a 2-alkenylamine compound according to claim 1 , wherein 0.000001 to 10 moles of the transition metal complex is used relative to one total mole of the primary or secondary amine compound and the 2-alkenyl compound (moles of the primary ...

PROCESSES FOR PREPARATION OF 4-AMINOINDANE DERIVATIVES AND RELATED AMINOINDANE AMIDES

A process for preparation of 4-aminoindane derivatives of a first formula, salts and enantiomers thereof comprising the steps of: a) hydrogenating a 1,2-dihydroquinoline of a second formula to give a corresponding tetrahydroquinoline of a third formula; b) acylating the tetrahydroquinoline of the third formula with a carboxylic acid derivative of a fourth formula to obtain a corresponding acyl derivative compound of a fifth formula; c) rearranging the acyl derivative compound of the fifth formula under acidic conditions so as to give an acyl indane compound of a sixth formula; and d) hydrolysing the acyl group of the acyl indane compound of the sixth formula so as to obtain the 4-aminoindane derivatives of the first formula. 2. The process of claim 1 , wherein the step (a) comprises contacting the 1 claim 1 ,2-dihydroquinoline of Formula (IV) dissolved in an organic solvent with gaseous hydrogen in a presence of a hydrogenation catalyst so as to obtain the tetrahydroquinoline of Formula (V).3. The process of claim 1 , wherein the carboxylic acid derivative of Formula RC(O)LG is selected from acetyl chloride claim 1 , acetic anhydride claim 1 , or mixtures thereof.4. The process of claim 1 , wherein the step (b) is carried out in an absence of added solvent.5. The process of claim 1 , wherein a reaction mixture obtained at an end of the step (b) is added with organic solvent and then subjected to distillation to remove an excess of the carboxylic acid derivative and to form a slurry containing the acyl derivative compound of Formula (VI).6. The process of claim 5 , wherein the slurry containing the acyl derivative compound of Formula (VI) is fed to the step (c).7. The process of claim 1 , wherein the step (c) comprises suspending the acyl derivative compound of Formula (VI) in an organic solvent and contacting the thus obtained suspension with an organic acid or an inorganic acid so as to obtain the acyl indane compound of Formula (VII) in a form of an addition salt. ...

Method For The Preparation Of Cinacalcet And Intermediates And Impurities Thereof

A method for the preparation of Cinacalcet is disclosed comprising treating (R)-1-naphthyl ethylamine with an aromatic aldehyde to form (1R)-1-(2-naphthyl)-N-(aryl methylene)ethanamine derivative of Formula (IV), which is further treated with 1-(3-halopropyl)-3-(trifluoromethyl)benzene of Formula (V) to obtain an iminium salt of Formula (VI), followed by hydrolysis to obtain Cinacalcet free base. 2. The method according to claim 1 , wherein the step (a) is carried out at a temperature from about 10° C. to 150° C.3. The method according to wherein the step (a) is carried out in the presence of a solvent.4. The method according to claim 3 , wherein the solvent is selected from the group consisting of hydrocarbons claim 3 , alcohols claim 3 , C-Cether claim 3 , C-Ccyclic ether claim 3 , C-Caliphatic ester claim 3 , C-Caliphatic amides claim 3 , sulfoxide claim 3 , C-Cchlorinated hydrocarbon claim 3 , 1-ethyl-3-methyl imidazolium ethylsulfate claim 3 , and mixtures thereof.5. The method according to wherein claim 1 , the compound of Formula (III) is selected from benzaldehyde claim 1 , salisaldehyde claim 1 , p-hydroxyl benzaldehyde claim 1 , o-chlorobenzaldehyde claim 1 , p-methoxy benzaldehyde claim 1 , o-methoxy benzaldehyde claim 1 , and p-nitrobenzaldehyde.6. The method according to claim 1 , further comprising isolating the compound of Formula (I) or a salt thereof in a crystalline form.7. The method according to claim 1 , wherein the step (b) is carried out at a temperature of 80° C. to 180° C.8. The method as according to claim 7 , wherein the step (b) is carried out in the presence of a solvent.9. The method according to claim 8 , wherein the solvent is selected from the group consisting of hydrocarbons claim 8 , alcohols claim 8 , C-Cethers claim 8 , C-Ccyclic ethers claim 8 , C-Caliphatic esters claim 8 , C-Caliphatic amides claim 8 , sulfoxides claim 8 , C-Cchlorinated hydrocarbons claim 8 , 1-ethyl-3-methyl imidazolium ethyl sulfate claim 8 , and mixtures ...

BENZYLATED TRIAMINONONANE AND USES THEREOF

The present invention provides benzylated triaminononane compounds, epoxy curing agent compositions comprising benzylated triaminononane compounds and methods of making such compositions. Amine-epoxy compositions and articles produced from these amine-epoxy compositions are also disclosed. 1. A curing agent composition comprising at least one benzylated triaminononane compound , wherein the benzylated triaminononane compound comprises the reaction product of a benzaldehyde compound or benzyl halide compound and a triaminononane compound.3. The composition of claim 2 , wherein the composition comprises about 10-20% mono-benzylated amines claim 2 , about 60-70% di-benzylated amines claim 2 , and about 15-20% tri-benzylated amines.4. The composition of claim 1 , wherein the molar reactant ratio of the benzaldehyde compound to the triaminononane is in a range from about 0.8:1 to about 3:1.5. The composition of claim 1 , wherein the molar reactant ratio of the benzyl halide compound to the triaminononane is in a range from about 0.8:1 to about 3:1.6. The composition of claim 1 , wherein the curing agent composition has an amine hydrogen equivalent weight (ANEW) based on 100% solids from about 50 to about 250.7. A method for forming a curing agent composition comprising contacting a benzaldehyde compound or benzyl halide compound and a triaminononane compound under conditions sufficient to form at least one benzylated triaminononane compound.9. The method of claim 7 , wherein the benzaldehyde compound and the triaminononane compound are reacted in a molar reactant ratio of the benzaldehyde compound to the triaminononane compound of about 0.8:1 to about 3:1.10. The method of claim 7 , wherein the benzyl halide and the triaminononane compound are reacted in a molar reactant ratio of the benzyl halide compound to the triaminononane compound of about 0.8:1 to about 3:1.11. An amine-epoxy composition comprising the contact product of: a curing agent composition comprising at ...

METHOD FOR PREPARING N,N'-BIS(3-AMINOPROPYL)-1,2-ETHYLENEDIAMINE

A method for preparing N,N′-bis(3-aminopropyl)-1,2-ethylenediamine uses a glycol ether based solution, such as a solution containing dipropylene glycol dimethyl ether (PM) to replace the traditionally used monol-based solvents, and performs hydrogenation in the presence of a Co—Mn—Al catalyst. The method improves the yield of N,N′-bis(3-aminopropyl)-1,2-ethylenediamine to 98.85-99.49% and effectively suppresses generation of by-products. 1. A method for preparing N ,N′-bis(3-aminopropyl)-1 ,2-ethylenediamine , comprising:a) in a high-pressure reactor, adding 1.00-2.00 wt % of a Co—Mn—Al catalyst and 33.21-38.53 wt % of a dipropylene glycol dimethyl ether-LiOH solution based on a weight of N,N′-bis(2-cyanoethyl)-1,2-ethylenediamine (BCNEDA) as a base material;b) in an environment of a temperature of 110-130° C. and a pressure of 700-900 psi, gradually pumping BCNEDA into the reactor under high speed stirring using a syringe pump within 3 hours;c) after pumping, allowing the mixture to continue reaction at 120° C.;d) using gas chromatography (GC) to verify that conversion of BCNEDA reaches 100% and finishing the reaction; ande) a yield of N,N′-bis(3-aminopropyl)-1,2-ethylenediamine (BAEDA) ranging between 98.85% and 99.49% is obtained.2. The method of claim 1 , wherein the Co—Mn—Al catalyst is added in an amount of 1.0 wt %.3. The method of claim 1 , wherein N claim 1 ,N′-bis(2-cyanoethyl)-1 claim 1 ,2-ethylenediamine is continuously introduced for hydrogenation.4. The method of claim 1 , wherein the pressure for synthesis is 800 psi.5. The method of claim 1 , wherein BCNEDA is gradually pumped into the reactor at the temperature of 120° C.6. The method of claim 1 , wherein the N claim 1 ,N′-bis(2-cyanoethyl)-1 claim 1 ,2-ethylenediamine is pumped in over a duration less than three hours.7. The method of claim 1 , wherein the dipropylene glycol dimethyl ether is added in an amount of 33 wt % based on the weight of the BCNEDA reactant.8. The method of claim 1 , wherein ...

ORGANIC-INORGANIC HYBRID PEROVSKITE COMPOUND, ITS PREPARATION METHOD AND SOLAR CELL COMPRISING THE SAME

In the organic-inorganic hybrid perovskite compounds according to the present invention, a zero point energy becomes lower, and thus the chemical stability of the perovskite compounds increases, thereby increasing the stability of the solar cells. Accordingly, the organic-inorganic hybrid perovskite compound according to the present invention can make the best use of a light-absorbing material of the solar cells. 1. An organic-inorganic hybrid perovskite compound represented by the following chemical formula 1 or 2:{'br': None, 'sub': '3', 'AMX\u2003\u2003[Formula 1]'}{'br': None, 'sub': 2', '4, 'AMX\u2003\u2003[Formula 2]'}in the above formulas,{'sub': 3-a', 'a', '3-b', 'b, 'sup': '+', 'A is CDHNDH, wherein a is a real number from 0 to 3, b is a real number from 0 to 3, except i) when a is 3 and b is 3, ii) when a is 3 and b is 0, or iii) when a is 0 and b is 3,'}M is a divalent metal ion, andX is a halogen ion.2. The organic-inorganic hybrid perovskite compound of claim 1 , wherein a and b are 0.3. The organic-inorganic hybrid perovskite compound of claim 1 , wherein M is Pb claim 1 , Sn claim 1 , Ti claim 1 , Nb claim 1 , Zror Ce.4. The organic-inorganic hybrid perovskite compound of claim 1 , wherein X is Cl claim 1 , Br or Ce.6. A solar cell comprising the organic-inorganic hybrid perovskite compound defined in .7. The solar cell of claim 6 , wherein the solar cell has the following structure:a first electrode including a conductive transparent substrate;a light absorbing layer, formed on the first electrode, comprising the organic-inorganic hybrid perovskite compound;a second electrode disposed opposite to the first electrode in which the light-absorbing layer is formed; andan electrolyte layer located between the first electrode and the second electrode. The present invention relates to an organic-inorganic hybrid perovskite compound having a deuterium, its preparation method and a solar cell comprising the same.In order to solve the depletion of fossil ...

DISTILLED CASHEW NUT SHELL LIQUID BASED, WATER THINABLE PHENALKAMINE AS CURING AGENT FOR EPOXY PAINT COMPOSITIONS

A water-Soluble phenalkamine curing agent including a water-soluble polyamine which is a reaction product of: (a) an unsaturated dicarboxylic acid modified distilled CNSL molecule; and (b) a water-soluble polyamine with aldehyde. The water soluble Mannich base is a reaction product of a polyamine containing at least two amino groups with a phenolic compound, with aid of an aldehyde. The dicarboxylic acid modified distilled CNSL intermediate is produce by diel alder reaction on side chain of cardanol which is renewable biomass. 1. A process for the production of water thinable phenalkamine curing agent for epoxy resins , comprising:a. modifying distilled cashew nut shell liquid with unsaturated dicarboxylic acid at the side chain unsaturation of cardanol by Diels alder reaction to obtain phenolic intermediate;b. converting the said phenolic intermediate in step a) into water-thinable phenalkamine curing agent for epoxy resins by Mannich reaction of reacting the said phenolic intermediate with polyamine and paraformaldehyde to obtain water-thinable phenalkamine curing agent; andc. diluting the said water-thinable phenalkamine curing agent of step (b) in demineralized and solvent-freed water to dilution between 10% to 50% by weight, wherein said water thinable phenalkaline curing agent for epoxy resins is in stable solution form.2. The process as claimed in claim 1 , wherein the said distilled cashew-nut-shell-liquid is a mixture of tri-unsaturated cardanol in 41 weight % as a major component claim 1 , mono-unsaturated cardanol in 34 weight % claim 1 , bi-unsaturated cardanol in 22 weight % and saturated cardanol in 2 weight % claim 1 , based on the total weight of the said distilled cashew-nut-shell liquid.3. The process as claimed in claim 1 , wherein the said Diel alder reaction is carried out claim 1 , keeping ratio of distilled cashew nut shell liquid to itaconic acid at 70:30 by weight and the reaction temperature between 190° C. to 200° C.4. The process as ...

METHOD FOR THE PRODUCTION OF AN AQUEOUS SOLUTION OF SALTS

The invention relates to a method for the continuous production of a solution of salts, in particular for the production of hexamethylenediamine adipate and a device for implementing such a method. According to the invention, it is proposed to convert, in a first step, a substoichiometric quantity of alkane diamine in a ratio to the alkane dicarboxylic acid in water and, in a subsequent second step, to implement making-up with alkane diamine, adjustment of the stoichiometric ratios being effected via a pH value measurement at a constant temperature. 1. A method for the continuous production of an aqueous solution of salts by conversion of alkane dicarboxylic acids with 6 to 12 carbon atoms and alkane diamines with 6 to 12 atoms , having the following steps:a) a defined quantity of alkane dicarboxylic acid is metered as solid material into a first reactor via at least one first feed point and a substoichiometric quantity of undiluted alkane diamine is metered in at at least a second feed point, and also, at the same time, water at at least one third feed point of the first reactor, for the production of an aqueous salt solution in the reactor,b) the formed salt solution is transferred continuously into a subsequently connected second reactor andc) making-up with the alkane diamine is effected in the second reactor, the stoichiometric ratios in the first and second reactor being adjusted by a pH value measurement at a constant temperature.2. The method according to claim 1 ,that wherein, in the first reactor, a pH value of 6.0 to 7 is maintained and, in the second reactor, a pH value of 6.8 to 7.8.3. The method according to claim 1 ,wherein, in the first reactor, a stoichiometric ratio of alkane dicarboxylic acid to alkane diamine of 1:0.80 to 0.99 is maintained.4. The method according to claim 1 ,wherein, in the first reactor, the aqueous solution is maintained at a concentration of salts of alkane dicarboxylic acid and alkane diamines of 50 to 65% by weight.5. The ...

PROCESS FOR PRODUCING SUBSTITUTED 4-AMINOINDANE DERIVATIVES FROM 2-(HYDROXYALKYL)-ANILINES

The present invention relates to a method for preparing substituted 4-aminoindane derivatives from 2-(hydroxyalkyl)-anilines by cyclization, 2. The process according to claim 1 , wherein Ris n-propyl claim 1 , Rand Reach are methyl and Ris hydrogen.3. The process according to claim 1 , wherein R claim 1 , Rand Rare methyl and Ris hydrogen.4. The process according to claim 1 , wherein the process is carried out at a temperature in a range of from 1° C. to 30° C. claim 1 , optionally at a temperature in a range of from 1° C. to 20° C.; optionally at a temperature in a range of from 1° C. to 15° C.5. The process according to claim 1 , wherein the process is carried out at a temperature in a range of from 5° C. to 15° C.6. The process according to claim 1 , wherein an aqueous sulfuric acid having a concentration of at least 85w % is used.7. The process according to claim 1 , wherein an aqueous sulfuric acid is used that has a concentration in a range of from 85w % to 97w % claim 1 , optionally that has a concentration in a range of from 88 w % to 92 w % claim 1 , optionally the concentration of the aqueous sulfuric acid is 90 w %.8. The process according to claim 1 , wherein the amount of used aqueous sulfuric acid or anhydrous hydrogen fluoride is in a range of from 3-45 molar equivalents claim 1 , optionally of from 6 to 40 molar equivalents claim 1 , optionally of from 9 to 35 molar equivalents based on a total amount of the compound of formula (IIa) or (Ib) or (IIc).9. The process according to claim 1 , wherein the reaction can be conducted in the presence or absence of a solvent claim 1 , optionally the reaction is conducted in absence of a solvent. The present invention relates to a process for preparing substituted 4-aminoindane derivatives by cyclization.4-Aminoindanes and corresponding derivatives are important intermediates for the preparation of bioactive compounds which can be used specifically for controlling harmful microorganisms in crop protection.For ...

Synthesis of Chiral Amphetamine Derivatives by Stereospecific, Regioselective Cuprate Addition Reaction with Aziridine Phosphoramidate Compounds

The invention includes processes for the synthesis of amphetamine, dexamphetamine, methamphetamine, derivatives of these, including their salts, and novel precursors and intermediates obtained thereby, by synthesizing aziridine phosphoramidate compounds in specified solvents at specified temperatures, and then converting to a novel aryl or aryl-alkyl phosphoramidate precursors using an organometallic compound such as a copper salt, where the novel aryl or aryl-alkyl phosphoramidate precursor is then easily converted to the target compounds using known reactions, 2. The process according to wherein the acidic conditions are aqueous hydrochloric claim 1 , sulfuric or phosphoric acids.3. The process according to wherein the aqueous acid water content is in an amount of 50% to 90%4. The process according to wherein R=methyl claim 1 , ethyl claim 1 , isopropyl or phenyl.6. The process according to wherein the solvent conditions comprise a crystallization step requiring a mixture of two or more solvents claim 5 , wherein one of the two or more solvents is residue THF.7. The process according to wherein R=methyl claim 6 , ethyl claim 6 , isopropyl or phenyl.8. The process according to wherein the copper halide catalyst is CuCl claim 5 , CuCl claim 5 , CuBr CuF claim 5 , Cu(OAc) claim 5 , Cu(acac) claim 5 , Cu(OMe) claim 5 , Copper turnings or Copper nanoparticles.9. The process according to wherein the non-THF residue solvent of the two or more solvents is selected from the group consisting of heptanes claim 6 , an organic ether 2-methyltetrahydrofuran methyl tert-butyl ether claim 6 , and toluene.10. (canceled)11. The process according to wherein said temperature conditions range from 25° C. to 80° C.13. The process according to wherein the R=methyl claim 12 , ethyl claim 12 , isopropyl or phenyl.14. The process according to claim 12 , wherein the base is potassium hydroxide or potassium carbonate.16. The process according to wherein the R=methyl claim 15 , ethyl claim 15 ...

Synthesis of Racemic Amphetamine Derivatives by Cuprate Addition Reaction with Aziridine Phosphoramidate Compounds

The invention includes processes for the synthesis of amphetamine, dexamphetamine, methamphetamine, derivatives of these, including their salts, and novel precursors and intermediates obtained thereby, by synthesizing aziridine phosphoramidate compounds in specified solvents at specified temperatures, and then converting to a novel aryl or aryl-alkyl phosphoramidate precursors using an organometallic compound such as a copper salt, where the novel aryl or aryl-alkyl phosphoramidate precursor is then easily converted to the target compounds using known reactions. 2. (canceled)3. (canceled)4. (canceled)6. The process according to wherein the compound of Formula 6 contains less than 0.1% regioisomeric impurity.7. The process according to wherein the R=methyl claim 6 , ethyl claim 6 , isopropyl or phenyl.8. The process according to wherein the copper catalyst is CuCl claim 1 , CuCl claim 1 , CuBr claim 1 , CuF claim 1 , Cu(OAc) claim 1 , Cu(acac) claim 1 , Cu(OMe) claim 1 , Copper nanoparticles claim 1 , Copper turnings claim 1 , or combinations thereof.9. The process according to wherein the mixture of two or more solvents comprises a mixture of organic solvent and residual THF.10. The process according to wherein the solvent and temperature conditions effective to produce a compound of Formula 6 comprise an organic ether-toluene mixture claim 1 , or an organic ether selected from the group consisting of diethyl ether claim 1 , tetrahydrofuran claim 1 , 2-methyltetrahydrofuran and mixtures thereof.11. The process according to wherein the phenylmagnesium halide is either phenylmagnesium chloride claim 1 , phenylmagnesium bromide or phenylmagnesium iodide.12. The process according to wherein the phenylmagnesium halide solutions can either be commercially supplied or prepared in situ from the corresponding halobenzene and magnesium.13. The process according to wherein the magnesium can be in the form of chips claim 12 , granules claim 12 , ribbon claim 12 , turnings claim ...

MULTI-STEP PROCESS FOR CONVERTING CYCLIC ALKYLENEUREAS INTO THEIR CORRESPONDING ALKYLENEAMINES

A process for converting a feedstock comprising cyclic alkyleneureas into their corresponding alkyleneamines is provided. The process includes a COremoval step in which cyclic alkyleneureas are converted into their corresponding alkyleneamines by reacting cyclic alkyleneureas in the liquid phase with water with removal of CO. The exemplary process further includes an amine removal step wherein cyclic alkyleneureas are converted in a reactive separation process into their corresponding alkyleneamines by reaction with an amine compound selected from the group of primary amines or secondary amines which have a higher boiling point than the alkyleneamines formed during the process. 1. A process for converting a feedstock comprising cyclic alkyleneureas into their corresponding alkyleneamines , comprising:{'sub': 2', '2, 'a COremoval step in which cyclic alkyleneureas are converted into their corresponding alkyleneamines by reacting cyclic alkyleneureas in the liquid phase with water with removal of CO, and'}an amine removal step wherein cyclic alkyleneureas are converted in a reactive separation process into their corresponding alkyleneamines by reaction with an amine compound selected from the group of primary amines or secondary amines which have a higher boiling point than the alkyleneamines formed during the process.2. The process according to wherein in the COremoval step from about 5% to about 95% of alkyleneurea moieties present in the feedstock are converted into amine moieties claim 1 , and in the amine removal step from about 5% to about 95% of alkyleneurea moieties present in the feedstock are converted into amine moieties.3. The process of wherein the feed to the COremoval step has a CO-loading of from about 0.2 to about 1.4. The process of wherein the feed to the amine removal step has a CO-loading of from about 0.05 to about 0.8.5. The process of comprising the steps of:{'sub': 2', '2', '2, 'providing a feedstock with a CO-loading of at least about 0.2 to ...

METHOD FOR PRODUCING COMPOUND

A method is provided for producing a compound, including a step of mixing a compound (1) having one or two leaving groups, a compound (2) having one or two boron atom-containing leaving groups, an organic base (P), and at least one selected from a phase transfer catalyst and an organic base (Q) larger in the number of carbon atoms than the above-mentioned organic base in the presence of a transition metal catalyst. The method thereby performs a coupling reaction between the above-mentioned compound (1) and the above-mentioned compound (2). 115-. (canceled)16. A method for producing a compound , the method comprising mixing a first compound having two leaving groups , a second compound having two boron atom-containing leaving groups , a first organic base , and at least one selected from the group consisting of a phase transfer catalyst and a second organic base larger in number of carbon atoms than the first organic base in the presence of a transition metal catalyst , such that the method performs a coupling reaction between the first compound and the second compound , wherein the transition metal catalyst is a divalent palladium catalyst.17. The method for producing a compound according to claim 16 , wherein the leaving groups of the first compound are selected from halogen atoms claim 16 , diazonio groups or groups represented by —O—S(═O)R claim 16 , wherein Rrepresents optionally substituted alkyl or aryl groups.18. The method for producing a compound according to claim 16 , wherein the phase transfer catalyst is an ammonium compound.19. The method for producing a compound according to claim 18 , wherein the ammonium compound has 16 to 60 carbon atoms.20. The method for producing a compound according to claim 16 , wherein the phase transfer catalyst is at least one selected from the group consisting of (CH)NF claim 16 , (CH)NCl claim 16 , (CH)NBr claim 16 , (CH)NI claim 16 , (CH)NCl claim 16 , (CH)NBr claim 16 , (CH)NI claim 16 , (CH)(CH)NCl claim 16 , (CH)(CH) ...

Processes for the Preparation of Dasotraline and Intermediates Thereof

The present invention provides processes for the preparation of Dasotraline (1), as well as intermediates useful in the preparation thereof. In particular, processes are provided for the production of the compound of Formula (2), or a salt thereof, and its deprotection to afford Dasotraline (1). 2. The process of claim 1 , wherein Ar is selected from the group consisting of phenyl claim 1 , alkoxy-substituted phenyl claim 1 , alkyl-substituted phenyl claim 1 , and naphthyl.3. The process of claim 2 , wherein Ar is selected from the group consisting of 4-methoxyphenyl and phenyl.4. The process of claim 3 , wherein Ar is 4-methoxyphenyl.5. The process of claim 4 , wherein Ris methyl.6. The process of claim 5 , wherein the deprotection is conducted by acid-mediated hydrolysis comprising treatment of the compound of Formula (2) with an acid selected from the group consisting of trifluoroacetic acid claim 5 , hydrochloric acid claim 5 , and trifluoromethanesulfonic acid.7. The process of claim 6 , wherein the acid is trifluoroacetic acid.8. The process of claim 1 , wherein the carbon atom marked with “*” is enantiomerically enriched in the (S)-configuration and the compound of Formula (2) has a chiral purity in favour of the (1R claim 1 ,4S)-configuration of at least about 90%.10. The process of claim 9 , wherein Ar is selected from the group consisting of phenyl claim 9 , alkoxy-substituted phenyl claim 9 , alkyl-substituted phenyl claim 9 , and naphthyl.11. The process of claim 10 , wherein Ar is selected from the group consisting of 4-methoxyphenyl and phenyl.12. The process of claim 11 , wherein Ar is 4-methoxyphenyl.13. The process of claim 12 , wherein Ris methyl.14. The process of claim 9 , wherein the reductant is selected from the group consisting of sodium borohydride claim 9 , sodium cyanoborohydride claim 9 , and sodium triacetoxyborohydride.15. The process of claim 9 , wherein the carbon atom marked with “*” is enantiomerically enriched in the (S)- ...

ISOMERIZATION METHOD FOR BIS (AMINOMETHYL) CYCLOHEXANE

A method for isomerizing a bis(aminomethyl)cyclohexane, including an isomerization step of isomerizing the bis(aminomethyl)cyclohexane in the presence of an imine compound represented by the following general formula (1) and at least one compound selected from the group consisting of an alkali metal, an alkali metal-containing compound, an alkaline earth metal and an alkaline earth metal-containing compound: 2: The method for isomerizing the bis(aminomethyl)cyclohexane according to claim 1 , wherein the substituted or unsubstituted hydrocarbon group represented by each of Rand Rcomprises a monovalent group selected from the group consisting of a substituted or unsubstituted aliphatic hydrocarbon group claim 1 , a substituted or unsubstituted alicyclic hydrocarbon group and a substituted or unsubstituted aromatic hydrocarbon group; and{'sup': '3', 'the substituted or unsubstituted hydrocarbon group represented by Rcomprises an n-valent group selected from the group consisting of a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alicyclic hydrocarbon group and a substituted or unsubstituted aromatic hydrocarbon group.'}4: The method for isomerizing the bis(aminomethyl)cyclohexane according to claim 2 , wherein the aliphatic hydrocarbon group comprises a linear or branched and substituted or unsubstituted aliphatic hydrocarbon group.5: The method for isomerizing the bis(aminomethyl)cyclohexane according to claim 2 , wherein the alicyclic hydrocarbon group comprises an alicyclic hydrocarbon group having an amino group.6: The method for isomerizing the bis(aminomethyl)cyclohexane according to claim 2 , wherein the aromatic hydrocarbon group comprises a monovalent group selected from the group consisting of a substituted or unsubstituted benzyl group claim 2 , a substituted or unsubstituted benzal group claim 2 , a substituted or unsubstituted monovalent phenyl group and a substituted or unsubstituted monovalent naphthyl group.7: ...

METHOD FOR PRODUCING BIS (AMINOMETHYL) CYCLOHEXANE

A method for producing a bis(aminomethyl)cyclohexane having an isomerization step of isomerizing a cis-isomer of 1,4-bis(aminomethyl)cyclohexane and/or a trans-isomer of 1,3-bis(aminomethyl)cyclohexane at the bottom part of a distillation tower to obtain a trans-isomer of 1,4-bis(aminomethyl)cyclohexane and/or a cis-isomer of 1,3-bis(aminomethyl)cyclohexane; and a distillation step of separating the trans-isomer of 1,4-bis(aminomethyl)cyclohexane and/or the cis-isomer of 1,3-bis(aminomethyl)cyclohexane by distillation, in the top part of the distillation tower, in which the isomerization reaction temperature in the isomerization step is 80 to 140° C., and the isomerization step and the distillation step are simultaneously carried out. 1: A method for producing a bis(aminomethyl)cyclohexane , the method comprising:isomerizing a cis-isomer of 1,4-bis(aminomethyl)cyclohexane and/or a trans-isomer of 1,3-bis(aminomethyl)cyclohexane at a bottom part of a distillation tower to obtain a trans-isomer of 1,4-bis(aminomethyl)cyclohexane and/or a cis-isomer of 1,3-bis(aminomethyl)cyclohexane at a temperature of 80 to 140° C. in the presence of an alkali metal-containing compound and a benzylamine compound; andseparating the trans-isomer of 1,4-bis(aminomethyl)cyclohexane and/or the cis-isomer of 1,3-bis(aminomethyl)cyclohexane by distillation, in a top part of the distillation tower,whereinthe isomerizing and the distillation are simultaneously carried out.2: The method of claim 1 , wherein a content of the trans-isomer in the 1 claim 1 ,4-bis(aminomethyl)cyclohexane obtained from the top part of the tower in the distillation is 84% or more.3: The method of claim 1 , wherein a content of the trans-isomer in the 1 claim 1 ,4-bis(aminomethyl)cyclohexane obtained from the top part of the tower in the distillation is 90% or more.4. (canceled)5: The method of claim 1 , wherein the benzylamine compound is at least one selected from the group consisting of benzylamine claim 1 , 3- ...

Method of Making a Templating Agent

A method for preparing 1-adamantyltrimethylammonium hydroxide is disclosed. The method comprises reacting 1-adamantyldimethylamine with dimethyl carbonate to produce 1-adamantyltrimethylammonium methylcarbonate, which is then reacted with calcium hydroxide or magnesium hydroxide in the presence of water to produce 1-adamantyltrimethylammonium hydroxide. 1. A method for preparing 1-adamantyltrimethylammonium hydroxide , comprising:(a) reacting the 1-adamantyldimethylamine with dimethyl carbonate to produce 1-adamantyltrimethylammonium methylcarbonate; and(b) reacting the 1-adamantyltrimethylammonium methylcarbonate with calcium hydroxide or magnesium hydroxide in the presence of a water to produce 1-adamantyltrimethylammonium hydroxide.2. The method of wherein the molar ratio of dimethyl carbonate:1-adamantyldimethylamine is in the range of 3 to 5.3. The method of wherein the molar ratio of calcium hydroxide or magnesium hydroxide:1-adamantyltrimethylammonium methylcarbonate is in the range of 1.05 to 1.75.4. The method of wherein the reaction of 1-adamantyltrimethylammonium methylcarbonate with calcium hydroxide or magnesium hydroxide in the presence of water is performed at reflux.5. The method of wherein the reaction of 1-adamantyldimethylamine with dimethyl carbonate is performed at a temperature in the range of 120-160° C.6. The method of wherein the 1-adamantyltrimethylammonium methylcarbonate is reacted with calcium hydroxide.7. The method of wherein the 1-adamantyldimethylamine is produced by reacting 1-adamantylamine hydrochloride claim 1 , formaldehyde claim 1 , formic acid claim 1 , and an inorganic base to produce 1-adamantyldimethylamine claim 1 , wherein the molar ratio of formaldehyde:1-adamantylamine hydrochloride is in the range of 2.1 to 2.4 and the molar ratio of formic acid:1-adamantylamine hydrochloride is in the range of 2.3 to 2.7.8. The method of wherein the inorganic base is a hydroxide claim 7 , a carbonate or a bicarbonate of a Group I ...

PROCESS FOR CONVERTING CYCLIC ALKYLENEUREAS INTO THEIR CORRESPONDING ALKYLENEAMINES

A process is provided for converting cyclic alkyleneureas into their corresponding alkyleneamines. The process includes reacting a feedstock comprising cyclic alkyleneureas in the liquid phase with water in an amount of from about 0.1 to about 20 mole water per mole urea moiety, at a temperature of at least 230° C., with removal of CO2. The process may allow the efficient conversion of alkyleneureas into the corresponding alkyleneamines. In certain embodiments, the process has a high yield and low side product production. 1. A process for converting cyclic alkyleneureas into their corresponding alkyleneamines , the process comprising reacting a feedstock comprising cyclic alkyleneureas in the liquid phase with water in an amount of from about 0.1 to about 20 mole water per mole urea moiety , at a temperature of at least about 230° C. , with removal of CO.3. The process according to wherein Ris a hydrogen atom.4. The process of claim 1 , wherein Ris ethylene claim 1 , propylene claim 1 , or isopropylene.5. The process of claim 1 , wherein the cyclic alkyleneurea comprises one or more of EU (ethyleneurea claim 1 , the urea derivative of ethylenediamine (EDA)) claim 1 , UDETA (the urea derivative of diethylenetriamine (DETA)) claim 1 , UTETA (the group of urea derivatives of triethylenetetraamine (TETA) claim 1 , DUTETA (the diurea derivative of triethylenetetramine) claim 1 , UTEPAs (the urea derivatives of tetraethylenpentamine (TEPA)) claim 1 , DUTEPAs (the diurea derivatives of TEPA) claim 1 , or urea derivatives of pentaethylenehexamine (PEHA) and higher analogues claim 1 , UAEEA (the urea derivative of aminoethylethanolamine) claim 1 , HE-UDETA (the urea derivative of hydroxyethyl diethylenetriamine) claim 1 , HE-UTETA (the urea derivative of hydroxyethyl triethylenetetraamine claim 1 , HE-DUTETA (the diurea derivative of hydroxyethyl triethylenetetraamine) claim 1 , or any mixture of these.6. The process of claim 1 , wherein the feedstock comprises at least ...

AMORPHOUS MATERIAL AND THE USE THEREOF

The present invention relates to a new amorphous material with advantageous properties as charge transport material and/or absorber material for various applications, in particular in photoelectric conversion devices, i.e. an amorphous material of the composition (RNR)Me XXwherein Ris C-C-alkyl, Rare independently of one another hydrogen or C-C-alkyl, Me is a divalent metal, Xand Xhave different meanings and are independently of one another selected from F, CI, Br, I or a pseudohalide, a and b are independently of one another 0 to 7, wherein the sum of a and b is 7. 1: An amorphous material having a composition{'br': None, 'sup': 1', '2', '1', '2, 'sub': 3', '5', 'a', 'b, '(RNR)MeXX'}wherein{'sup': '1', 'sub': 1', '4, 'Ris C-C-alkyl,'}{'sup': '2', 'sub': 1', '4, 'Rare independently of one another hydrogen or C-C-alkyl,'}Me is a divalent metal,{'sup': 1', '2, 'Xand Xare different from each other, and are independently of one another selected from the group consisting of F, Cl, Br, I and a pseudohalide, and'}a and b are independently of one another 0 to 7, wherein the sum of a and b is 7.2: The amorphous material according to claim 1 , wherein Ris methyl or ethyl.3: The amorphous material according to claim 1 , wherein the Rgroups are all hydrogen.4: The amorphous material according to claim 1 , wherein Me is at least one element selected from the group consisting of Pb claim 1 , Sn claim 1 , Fe claim 1 , Zn claim 1 , Cd claim 1 , Co claim 1 , Cu claim 1 , Ni claim 1 , and Mn.5: The amorphous material according to claim 1 , wherein Me is Pb or Sn.6: The amorphous material according to claim 1 , wherein Xis I and Xis Cl.7: The amorphous material according to claim 1 , wherein a and b are both 3.5.8: An amorphous material having a composition{'br': None, 'sub': 3', '3', '5', '3.5', '3.5, '(CHNH)PbICl'}{'br': None, 'or'}{'br': None, 'sub': 3', '3', '5', '3.5', '3.5, '(CHNH)SnICl.'}9: A composition comprising the amorphous material of .10: A process for preparing an ...

ENAMIDE PROCESS

A convenient method for converting oximes into enamides is disclosed. The process produces enamides without the concomitant production of a large volume of metallic waste. 1. A process for converting an oxime to an enamide , said process comprising contacting said oxime with an acyl donor and a phosphine in the presence of an iron reagent that provides from 10 to 2000 ppm iron under conditions that convert said oxime to said enamide.2. The process according to wherein the acyl donor is acetic anhydride.3. The process according to wherein the phosphine is chosen from tri n-butylphosphine claim 1 , triethyl phosphine claim 1 , diphenylphosphinoethane and triphenyl phosphine.4. The process according to wherein the phosphine is triethyl phosphine.5. The process according to wherein the iron reagent is chosen from elemental iron and Fe(II) salts and Fe(III) salts wherein the counter ion is halide or alkanoate.5. The process according to wherein the iron reagent is chosen from FeCland Fe(OAc).6. The process according to wherein said iron reagent provides from 10 to 100 ppm iron.7. The process according to wherein said iron reagent provides from 10 to 50 ppm iron8. The process according to wherein said iron reagent provides from 25 to 100 ppm iron9. The process according to wherein said iron reagent provides from 500 to 2000 ppm iron10. The process according to wherein said process is carried out in a solvent at a temperature between 80° C. and 150° C.11. The process of wherein said solvent is toluene.12. The process according to wherein the oxime is an aliphatic ketone oxime.13. The process according to wherein the oxime is a tetralone oxime.14. A process for converting a ketone to an enamide claim 1 , said process comprising the sequential steps of:(a) reacting said ketone with hydroxylamine to provide an oxime; and(b) reacting said oxime with an acyl donor and a phosphine in the presence of an iron reagent that provides from 10 to 2000 ppm iron.15. A process for ...

Method for producing bis (aminomethyl) cyclohexane

A method for producing a bis(aminomethyl)cyclohexane having an isomerization step of isomerizing a cis-isomer of 1,4-bis(aminomethyl)cyclohexane and/or a trans-isomer of 1,3-bis(aminomethyl)cyclohexane at the bottom part of a distillation tower to obtain a trans-isomer of 1,4-bis(aminomethyl)cyclohexane and/or a cis-isomer of 1,3-bis(aminomethyl)cyclohexane; and a distillation step of separating the trans-isomer of 1,4-bis(aminomethyl)cyclohexane and/or the cis-isomer of 1,3-bis(aminomethyl)cyclohexane by distillation, in the top part of the distillation tower, in which the isomerization reaction temperature in the isomerization step is 80 to 140° C., and the isomerization step and the distillation step are simultaneously carried out.

Method for Preparation of Cyano Compounds of the 13th Group with a Lewis Acid

The invention discloses a method for preparation of cyano compounds of the 13th group of the periodic table with 1, 2, 3 or 4 cyano residues, represented by formula (I): [Cat][(ZF(CN))]by a reaction of [(ZF)] with trimethylsilylcyanide in the presence of a Lewis acid and in the presence of the cation Cat; Cat is a cation, Zis B, Al, Ga, In or Tl, m is 1, 2, 3 or 4 and n is 1, 2, 3 or 4. 122-. (canceled)23. A method for the preparation of a compound of formula (I);{'br': None, 'sup': n+', '1', '−, 'sub': 4-m', 'm', 'n, '[Cat][(ZF(CN))]\u2003\u2003(I)'}the method comprises a step (St1); {'br': None, 'sup': n+', '1', '−, 'sub': 4', 'n, '[Cat][(ZF)]\u2003\u2003(A1)'}, 'step (St1) comprises a reaction (Rea1), wherein a compound of formula (A1) is reacted with trimethylsilylcyanide in the presence of CATLEWISACID;'}CATLEWISACID is a catalyst CAT;{'sub': 3', '3', '3', '3', '3', '3', '3', '3', '3', '3', '5', '3', '2', '2', '3', '2, 'CAT is selected from the group consisting of [(CH)SiFSi(CH)][ANIO], Q1(R27), guanidinium[ANIO], (R26)C[ANIO], adamantyl[ANIO], [(R24)O][ANIO], [(R25)Si][ANIO], Q2(R36)(R28), Q3(R29), Q4(R30), Q5(R32), Q6(R33), Q8(R34), Q9(R35), Q10(R37), zeolite and mixtures thereof;'}{'sub': 6-m1', 'm1', '4-m2', 'm2, 'sup': −', '−', '−', '−', '−', '−', '−', '−, 'ANIO is selected from the group consisting of [P(R40)(R41)], [B(R42)(R43)], F, Cl, Br, I, CN and SCN;'}R40 and R41 are identical of different in independently from each other selected from the group consisting of CN, SCN, F, Cl, Br and I;m1 is 0, 1, 2, 3, 4 or 5;{'sub': 6', '5, 'R42 and R43 are identical of different in independently from each other selected from the group consisting of CF, CN, SCN, F, Cl, Br and I;'}m2 is 0, 1, 2 or 3;Q1 is selected from the group consisting of B, Al and Ga;{'sub': 1-10', '1-10', '6', '5, 'R27 is selected from the group consisting of Calkoxy, halogen, Calkyl, CN, SCN and CF;'}{'sub': '1-10', 'R24 is Calkyl;'}{'sub': '1-10', 'R25 is Calkyl;'}{'sub': '1-10', 'R26 is ...

PROCESS TO CONVERT THE CYCLIC MONOUREA OF AN ETHYLENE AMINE COMPOUND INTO THE ETHYLENE AMINE COMPOUND

A process to convert the cyclic monourea of ethylene amine compounds (U-EA) into ethylene amine compound (EA) is provided. The process may include performing a reactive separation step using a reaction mixture containing the cyclic monourea, wherein one cyclic monourea (U-EA) reacts with another cyclic monourea (U-EA) to transfer its urea unit thereto. The process may further include separating the obtained ethylene amine compound (EA) without urea unit from the reaction mixture. 1. A process to convert the cyclic monourea of ethylene amine compounds (U-EA) into ethylene amine compound (EA) , the process comprising:performing a reactive separation step using a reaction mixture containing the cyclic monourea, wherein one cyclic monourea (U-EA) reacts with another cyclic monourea (U-EA) to transfer its urea unit thereto; andseparating the obtained ethylene amine compound (EA) from the reaction mixture.2. The process of wherein the ethylene amine compound (EA) is triethylene tetraamine (TETA) or tetraethylene pentaamine (TEPA).3. The process of wherein the ethyleneamine compound EA is triethylenetetraamine (TETA).4. The process of wherein the reaction is done in less than about 10 wt % of water on the basis of total weight of the reaction mixture.5. The process of wherein the reaction is done at a temperature of at least about 150° C.6. The process of wherein the reaction is done at a pressure of below about 1 bara.7. The process of further comprising hydrolyzing any urea compound DU-EA formed from reaction between at least two cyclic urea compounds with water claim 1 , or water containing a base claim 1 , to release its carbonyl group to provide carbon dioxide or an ionic derivative thereof.8. The process further comprising separating of the carbon dioxide or ionic derivative thereof.9. The process of further comprising recycling any urea compound DU-EA formed from reaction between at least two cyclic urea compounds is recycled back into the reactive separation ...

Process for Preparing Cinacalcet and Pharmaceutically Acceptable Salts Thereof

The present patent application relates to a process for preparing, cinacalcet or a pharmaceutically acceptable salt thereof, which comprises reacting 3-trifluoromethylbenzaldehyde having the following formula (II) with the phosphorus-comprising derivative having the following formula all) in which Rand R, which may he identical or different, are each a (C-C)alkyl group. The present invention also relates to the phosphorus-comprising derivative having the formula (III), to the use thereof and to the process for preparing same. The present invention also relates to the phosphate salt of cinacalcet and to uses thereof. 118-. (canceled)20. The process according to claim 19 , wherein Rand Rare the same.21. The process according to claim 20 , wherein Rand Reach are an ethyl group.22. The process according to claim 19 , wherein the reaction is conducted in the presence of a base.23. The process according to claim 22 , wherein the base is selected from the group consisting of sodium hydride claim 22 , an alkaline metal alkoxide claim 22 , lithium 2 claim 22 ,2 claim 22 ,6 claim 22 ,6-tetramethylpiperidide (LiTMP) claim 22 , lithium or potassium hexamethyldisilazide (LiHMDS or KHMDS) claim 22 , lithium diisopropylamide (LDA) claim 22 , and 1 claim 22 ,8-diazabicyclo[5.4.0]undec-7-ene (DBU).24. The process according to claim 19 , wherein the reaction is conducted in a solvent selected from among dimethylformamide (DMF) claim 19 , dimethylsulfoxide (DMSO) claim 19 , tetrahydrofuran (THF) claim 19 , 2-methyl-tetrahydrofuran (MeTHF) claim 19 , and dimethyl ether (DME).25. The process according to claim 19 , wherein the (II):(III) weight ratio is about 1:1.27. The process according to claim 26 , wherein hydrogenation is performed under a hydrogen atmosphere in the presence of a hydrogenation catalyst.28. The process according to claim 27 , wherein the hydrogenation catalyst is palladium on carbon (Pd/C).29. The process according to claim 27 , wherein the hydrogenation reaction is ...

METHOD FOR PRODUCING DIAMINOTOLUENE

The invention relates to an industrial-scale method for the vapor-phase hydrogenation of dinitrotoluene (DNT). According to said method, a stream containing DNT is sprayed into a carrier-gas stream containing hydrogen, optionally in the presence of an atomizing gas, unevaporated liquid droplets are extracted from the substantially gaseous stream that is obtained and the resultant gas stream is catalytically hydrogenated to form diaminotoluene. 1. A continuous process for preparing toluenediamine by hydrogenation of dinitrotoluene in the gas phase , comprising: a) the temperature of the dinitrotoluene-comprising stream is from 70° C. to 150° C. and the temperature of the hydrogen-containing carrier gas stream is from 140° C. to 300° C.,', 'b) the absolute pressure of the dinitrotoluene-comprising stream is from 3.0 bar to 30 bar and the absolute pressure of the hydrogen-containing carrier gas stream is from 1.0 bar to 10 bar, where the pressure of the dinitrotoluene-comprising stream is higher than that of the hydrogen-containing carrier gas stream, and', 'c) the molar ratio of hydrogen to dinitrotoluene is from 6.0:1 to 900:1.', 'so as to give a stream comprising dinitrotoluene and hydrogen;, '(I) spraying of a dinitrotoluene-comprising stream into a hydrogen-containing carrier gas stream in a vaporization apparatus, where'}(II) removing or targetedly decomposing the liquid droplets present in the stream comprising dinitrotoluene and hydrogen from step (I) to give a gas stream which comprises dinitrotoluene and hydrogen and has been depleted in liquid droplets;(III) reacting the dinitrotoluene present in the gas stream which comprises dinitrotoluene and hydrogen and has been depleted in liquid droplets with hydrogen in at least one reaction space in the presence of a catalyst at an absolute pressure of from 1.0 bar to 10 bar, a temperature of from 140° C. to 300° C. and a residence time in the reaction space of from 0.1 s to 10 s, so as to give a toluenediamine- ...

METHOD FOR PREPARING ARYL SUBSTITUTED P-PHENYLENEDIAMINE SUBSTANCE

A method for preparing an aryl substituted p-phenylenediamine substance is provided. A structural formula of the aryl substituted p-phenylenediamine substance is shown as Formula (I′), where each of R′ and R″ is phenyl or o-methylphenyl, and R′ is same as or different from R″; and the method comprises that: a raw material A and a raw material B are reacted in the presence of a hydrogen acceptor and a catalyst to form the aryl substituted p-phenylenediamine substance, the raw material A having a structure shown as Formula (I), the raw material B being cyclohexanone and/or o-methylcyclohexanone and the hydrogen acceptor being a hydrogen acceptor capable of accepting hydrogen for conversion into the raw material B. Raw materials are low in cost and readily available; use of a large amount of water for post-treatment is avoided. The reaction condition is relatively mild, and corrosion to equipment is avoided. 2. The method as claimed in claim 1 , wherein a molar ratio of the raw material A and the raw material B is 20:1 to 5:1 claim 1 , and a molar ratio of the raw material A and the hydrogen acceptor is 1:10 to 1:2.5.3. The method as claimed in claim 2 , wherein the hydrogen acceptor is phenol claim 2 , o-cresol claim 2 , or both.4. The method as claimed in claim 3 , wherein the aryl substituted p-phenylenediamine substance is rubber antidegradant 3100 claim 3 , and the method comprisingtaking N-phenyl p-phenylenediamine as the raw material A, taking the cyclohexanone, the o-methylcyclohexanone, or both as the raw material B, taking the phenol as the hydrogen acceptor, and performing reaction in the presence of the catalyst to obtain a first component;taking the N-phenyl p-phenylenediamine as the raw material A, taking the cyclohexanone, the o-methylcyclohexanone, or both as the raw material B, taking the o-cresol as the hydrogen acceptor, and performing reaction in the presence of the catalyst to obtain a second component, or, taking N-o-methylphenyl p- ...

BENZYLATED MANNICH BASE CURING AGENTS, COMPOSITIONS, AND METHODS

Compositions and curing agents comprising a benzylated Mannich base composition. The benzylated Mannich base composition includes a reaction product of (a) a substituted phenolic compound having at least one substituent of formula (I): 2. The composition of claim 1 , comprising at least one benzylated Mannich base composition having at least two nitrogen atoms claim 1 , at least two active amine hydrogen atoms per molecule.3. The composition of claim 1 , wherein the substituted phenolic compound is selected from the group consisting of low molecular weight di-alkylaminomethyl-substituted phenols claim 1 , ortho- claim 1 , meta- and para-cresols claim 1 , cardanol claim 1 , the isomeric xylenols claim 1 , para-tert-butylphenol claim 1 , para-nonylphenol claim 1 , alpha-naphthol claim 1 , beta-naphthol claim 1 , diphenols or polyphenols claim 1 , hydroquinone claim 1 , 4 claim 1 ,4′-dihydroxydiphenyl claim 1 , 4 claim 1 ,4′-dihydroxydiphenyl ether claim 1 , 4 claim 1 ,4′-dihydroxydiphenylsulfone claim 1 , 4 claim 1 ,4′-dihydroxydiphenylmethane claim 1 , bisphenol A claim 1 , the condensation products of phenol and formaldehyde claim 1 , and combinations thereof.5. The composition of claim 1 , wherein the benzylated polyalkylene is selected from the group consisting of benzylated polyethylene polyamine claim 1 , benzylated polypropylene polyamine claim 1 , benzylated polyethylene-polypropylene polyamines claim 1 , and combinations thereof.6. The composition of claim 1 , wherein the benzylated polyalkylene is selected from the group consisting of benzylated ethylene diamine claim 1 , benzylated diethylenetriamine claim 1 , and benzylated triethylenetetramine claim 1 , benzylated tetraethylenepentamine claim 1 , benzylated propylene diamine claim 1 , benzylated dipropylenetriamine claim 1 , benzylated tripropylenetetramine claim 1 , benzylated N3 claim 1 , benzylated N4 claim 1 , benzylated N5 claim 1 , and combinations thereof.7. The composition of claim 1 , wherein the ...

Supported Metal Catalysts

The present invention relates to supported metal catalysts, wherein the catalysts are modified by at least one amine, a method for the preparation thereof and hydrogenation processes utilising the supported metal catalysts. 1. A supported metal catalyst , wherein the catalyst is modified by at least one amine , provided that when the metal is Pt and the support is AlO , the amine is not:a) S-benzyl-L-cysteine;b) N-benzyl-S-benzyl-L-cysteine;c) L-cysteine ethyl ester;d) S-benzyl-L-cysteine ethyl ester;e) N-benzyl-S-benzyl-L-cysteine ethyl ester;f) S-phenyl-L-cysteine ethyl ester; org) N-benzyl-S-phenyl-L-cysteine ethyl ester.2. The catalyst of claim 1 , wherein the support is carbon claim 1 , alumina claim 1 , calcium carbonate claim 1 , titania claim 1 , silica claim 1 , zirconia claim 1 , ceria claim 1 , or a combination thereof.3. The catalyst of claim 2 , wherein the alumina is alpha-AlO claim 2 , beta-AlO claim 2 , gamma-AlO claim 2 , delta-AlO claim 2 , theta-AlOor a combination thereof.4. The catalyst of claim 2 , wherein the carbon is activated carbon claim 2 , carbon black claim 2 , or graphite.5. The catalyst of claim 2 , wherein the carbon is Norit Carbon GSX claim 2 , Ceca L4S claim 2 , Ceca 2S claim 2 , Ceca CPL claim 2 , Timcal T44 Graphite claim 2 , or a combination thereof.6. The catalyst of claim 1 , wherein at least one metal is a Group VIII metal or Group IB metal.7. The catalyst of claim 1 , wherein the metal is ruthenium claim 1 , rhodium claim 1 , palladium claim 1 , osmium claim 1 , iridium claim 1 , platinum claim 1 , gold claim 1 , silver claim 1 , copper claim 1 , iron claim 1 , cobalt claim 1 , nickel claim 1 , or a combination thereof.8. The catalyst of claim 1 , wherein the metal is palladium claim 1 , platinum claim 1 , gold claim 1 , or a combination thereof.9. The catalyst of claim 1 , wherein the metal loading is from about 0.01 wt % to about 20 wt %.10. The catalyst of claim 1 , wherein the amine is a natural amino acid claim 1 , non ...

METHOD FOR PRODUCING CATALYST FOR USE IN PRODUCTION OF METHYLAMINE COMPOUND, AND METHOD FOR PRODUCING METHYLAMINE COMPOUND

According to the present invention, a method for producing a catalyst for use in the production of a methylamine compound can be provided, wherein the catalyst comprises a modified crystalline silicoaluminophosphate salt molecular sieve. The method comprises: a moisture control step of adsorbing moisture onto a crystalline silicoaluminophosphate salt molecular sieve in an amount of 5 to 30 wt % of the crystalline silicoaluminophosphate salt molecular sieve; and a step of heating the crystalline silicoaluminophosphate salt molecular sieve having moisture adsorbed thereon under a pressure of 0.1 MPa or more and at a temperature of 130 to 350° C. for 5 to 40 hours. 1. A method for producing a catalyst for use in the production of a methylamine compound , the catalyst comprising a modified crystalline silicoaluminophosphate salt molecular sieve , wherein the method comprises:a moisture control step of adsorbing moisture onto a crystalline silicoaluminophosphate salt molecular sieve in an amount of 5 to 30 wt % of the crystalline silicoaluminophosphate salt molecular sieve; anda step of heating the crystalline silicoaluminophosphate salt molecular sieve having moisture adsorbed thereon under a pressure of 0.1 MPa or more and at a temperature of 130 to 350° C. for 5 to 40 hours.2. The method for producing a catalyst for use in the production of a methylamine compound according to claim 1 , wherein the crystalline silicoaluminophosphate salt molecular sieve is at least one selected from SAPO-14 claim 1 , 17 claim 1 , 18 claim 1 , 21 claim 1 , 22 claim 1 , 25 claim 1 , 33 claim 1 , 34 claim 1 , 35 claim 1 , 39 claim 1 , 42 claim 1 , 43 claim 1 , 44 claim 1 , 47 claim 1 , 52 and 56.3. The method for producing a catalyst for use in the production of a methylamine compound according to claim 1 , wherein the crystalline silicoaluminophosphate salt molecular sieve comprises at least one type of element selected from among Mg claim 1 , Ca claim 1 , Sr claim 1 , Y claim 1 , Ti ...

METHOD OF PRODUCING CHIRAL N-SUBSTITUTED ALLYLIC AMINE COMPOUNDS

The method relates to the field of asymmetric allylic amination and comprises preparing a chiral N-substituted allylic amine compound from the corresponding allylic substrates and substituted hydroxylamines, in the presence of a catalyst, said catalyst comprising copper compounds and a chiral ligand. Examples of chiral amine compounds which can be made using the method include Vigabatrin, Ezetimibe Terbinafine, Naftifine 3-methylmorphine, Sertraline, Cinacalcet, Mefloquine hydrochloride, and Rivastigmine. There are over 20,000 known bioactive molecules with chiral N-substituted allylic amine substructure. The method may also be used to produce non-natural chiral β-aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of β-aminoacid ester which can be produced by the disclosed method, include, but are not limited to, N-(2-methylpent-1-en-3-yl)benzenamine and Ethyl 2-methylene-3-(phenylamino)butanoate. Further, the products of the method described herein can be used to produce chiral heterocycles and bioactive molecules or materials. 1. A method of producing a chiral N-substituted allylic amine compound comprising:(i) mixing an olefin compound, said olefin compound comprising an allylic C—H group, with an aminating reagent, said aminating reagent comprising a substituted hydroxylamine; and(ii) adding a chiral ligand and a copper (Cu(I)) compound to the mixture.2. The method of claim 1 , wherein said olefin compound comprises the general structure R—C(C—HR)═CHR.3. The method of claim 1 , wherein said olefin compound is selected from the group consisting of: 2-Methyl-2-butene claim 1 , 2-Methyl-2-pentene claim 1 , 2-Methyl-2-heptene claim 1 , 2 claim 1 ,5-Dimethyl-2-hexene claim 1 , Ethyltiglate claim 1 , sec-Betyltiglate claim 1 , Benzyltiglate claim 1 , methy-2-methyl-2-pentenoate claim 1 , 2-methyl-2-butenal claim 1 , 2-methyl-2-pentenal claim 1 , and 3-methyl-3-penten-2-one.4. The method of claim 1 , wherein said aminating reagent ...

METHOD FOR PRODUCING RACEMATE OF COMPOUND

A method for producing a racemate of a compound represented by Formula (1), including bringing a transition metal catalyst into contact with an optically active form of the compound represented by Formula (1): 3. The production method according to claim 2 , wherein A claim 2 , A claim 2 , A claim 2 , and Aare C(R)═.4. The production method according to claim 2 , wherein Ais —C(R)═ claim 2 , and Rand Rare bonded to each other to form a divalent hydrocarbon group.6. The production method according to claim 2 , wherein Ris a Calkyl group.8. The production method according to claim 1 , wherein the transition metal catalyst is a hydrogen-absorbing transition metal catalyst having absorbed hydrogen therein.9. The production method according to claim 1 , wherein the transition metal catalyst is a palladium catalyst.10. The production method according to claim 9 , wherein the palladium catalyst is a palladium-carbon catalyst. The present invention relates to a method for producing a racemate from an optically active form of a compound.Patent Literature 1 describes (3R)-1,1,3-trimethyl-4-aminoindane as an intermediate for use in producing agricultural chemicals, etc.Non-Patent Literature 1 describes a method for racemizing an optically active form of 2-phenylbutane by bringing an optically active form of 2-phenylbutane into contact with aluminum chloride.However, a method for racemizing an optically active form of (3R)-1,1,3-trimethyl-4-aminoindane, etc. is not known.[Patent Literature 1] Japanese Unexamined Patent Application Publication No. 1-211568There is a demand for a method for efficiently producing a racemate from an optically active form of a compound of (3R)-1,1,3-trimethyl-4-aminoindane, etc.The present invention includes the following aspects of the invention.[1] A method for producing a racemate of a compound represented by Formula (1), comprising bringing a transition metal catalyst into contact with an optically active form of the compound represented by ...

NOVEL PROCESSES FOR THE PREPARATION OF PHENYLCYCLOPROPYLAMINE DERIVATIVES AND USE THEREOF FOR PREPARING TICAGRELOR

Provided herein are novel processes for the preparation of phenylcyclopropylamine derivatives, which are useful intermediates in the preparation of triazolo[4,5-d]pyrimidine compounds. Provided particularly herein are novel, commercially viable and industrially advantageous processes for the preparation of a substantially pure ticagrelor intermediate, trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine. Provided further herein are novel acid addition salts of trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine, and process for their preparation. The intermediate and its acid addition salts are useful for preparing ticagrelor, or a pharmaceutically acceptable salt thereof, in high yield and purity. 2. The process of claim 1 , wherein the alcohol used in step-(a) is selected from the group consisting of methanol claim 1 , ethanol claim 1 , isopropyl alcohol claim 1 , isobutanol claim 1 , tert-butanol claim 1 , n-pentanol claim 1 , cyclohexanol claim 1 , l or d-menthol claim 1 , benzyl alcohol claim 1 , and mixtures thereof; wherein the first solvent used in step-(a) is selected from the group consisting of an ester claim 1 , a nitrile claim 1 , a hydrocarbon claim 1 , a cyclic ether claim 1 , an aliphatic ether claim 1 , and mixtures thereof; wherein the azide used in step-(a) is selected from the group consisting of diethylphosphoryl azide claim 1 , diisopropylphosphoryl azide claim 1 , di-tert-butylphosphoryl azide claim 1 , dibutylphosphoryl azide claim 1 , dibenzylphosphoryl azide claim 1 , di-l or d-menthylphosphoryl azide and diphenylphosphoryl azide; wherein the acid used in step-(b) is selected from the group consisting of methanesulfonic acid claim 1 , trifluoromethanesulfonic acid claim 1 , trifluoroacetic acid claim 1 , hydrochloric acid claim 1 , sulfuric acid claim 1 , hydrobromic acid claim 1 , and mixtures thereof; and wherein the second solvent used in step-(b) is selected from the group consisting of water claim 1 , an alcohol claim 1 , an ester ...

DEUTERIUM ENRICHED RASAGILINE

The subject invention provides deuterated rasagiline, its salts and uses. 2. The deuterium enriched compound of or a pharmaceutically acceptable salt thereof claim 1 , wherein Ris deuterium enriched claim 1 , and each of Rand Ris H.3. The deuterium enriched compound of or a pharmaceutically acceptable salt thereof claim 1 , wherein Ris H claim 1 , and each of Rand Ris deuterium enriched.4. The deuterium enriched compound of or a pharmaceutically acceptable salt thereof claim 1 , wherein each of R claim 1 , Rand Ris deuterium enriched.5. The deuterium enriched compound of or a pharmaceutically acceptable salt thereof claim 1 , wherein the at least one of R-Ris deuterium enriched to have an isotopic purity of at least 10%.6. The deuterium enriched compound of or a pharmaceutically acceptable salt thereof claim 1 , wherein the at least one of R-Ris deuterium enriched to have an isotopic purity of at least 50%.7. The deuterium enriched compound of or a pharmaceutically acceptable salt thereof claim 1 , wherein the at least one of R-Ris deuterium enriched to have an isotopic purity of at least 70%.8. The deuterium enriched compound of or a pharmaceutically acceptable salt thereof claim 1 , wherein the at least one of R-Ris deuterium enriched to have an isotopic purity of at least 90%.9. The deuterium enriched compound of or a pharmaceutically acceptable salt thereof claim 1 , wherein the at least one of R-Ris deuterium enriched to have an isotopic purity of at least 95%.10. The deuterium enriched compound of claim 1 , in the form of free base.11. The deuterium enriched compound of claim 1 , in the form of a pharmaceutically acceptable salt claim 1 , wherein the pharmaceutically acceptable salt is selected from the group consisting of citrate claim 1 , mesylate claim 1 , maleate claim 1 , malate claim 1 , fumarate claim 1 , tannate claim 1 , tartrate claim 1 , esylate claim 1 , p-toluenesulfonate claim 1 , benzoate claim 1 , acetate claim 1 , phosphate claim 1 , oxalate ...

METHOD FOR SELECTIVE PALLADIUM-CATALYZED TELOMERIZATION OF SUBSTITUTED DIENES

A method for the selective synthesis of a tail-to-head, or a head-to-head, or a tail-to-tail telomer from an unsymmetrical diene by polymerizing the diene in the presence of [Pd(CH)COD]BFand dicyclohexyl-[1-(2,4,6-trimethylphenyl)imidazol-2-yl]phosphane, Pd(OAc)and triphenylphosphine, or [Pd(CH)COD]BFand tris(2,4-di-tert-butylphenyl)phosphite in combination with a polar protic alcohol, an acidic polar protic alcohol, a polar aprotic ether, or a non-polar aprotic hydrocarbon is provided. 1. A method for regioselective synthesis of a telomer from a diene comprising the step of polymerizing the diene in the presence of an active catalytic system containing: [{'sub': 3', '5', '4', '2, '(i) the active catalyst precursor is selected from the group consisting of [Pd(CH)COD]BFand Pd(OAc); and'}, '(ii) the ligand is selected from the group consisting of dicyclohexyl-[1-(2,4,6-trimethylphenyl) imidazol-2-yl]phosphane, triphenylphosphine and tris(2,4-di-tert-butylphenyl)phosphite; and, '(a) an active catalyst precursor and a ligand, wherein'}(b) a solvent comprising methanol, ethanol, propanol, iso-propanol, toluene, acetone, acetonitrile, trifluoroethanol, diethyl ether or tetrahydrofuran.2. The method of claim 1 , wherein the active catalyst precursor and the ligand have a molar ratio between 1:3 and 1:0.1.3. The method of claim 1 , wherein the active catalyst precursor is [Pd(CH)COD]BF; the ligand is dicyclohexyl-[1-(2 claim 1 ,4 claim 1 ,6-trimethylphenyl)imidazol-2-yl]phosphane; and the solvent comprises methanol claim 1 , ethanol claim 1 , propanol claim 1 , iso-propanol claim 1 , toluene claim 1 , acetone claim 1 , or acetonitrile and wherein the telomer comprises a tail-to-head telomer.4. The method of claim 3 , wherein the tail-to-head telomer has a yield of greater than 60% by weight.5. The method of claim 1 , wherein the active catalyst precursor is [Pd(CH)COD]BF; the ligand is triphenylphosphine; and the solvent comprises trifluoroethanol claim 1 , and wherein the ...

Method for the Preparation of 4-(Heptafluoro-2-Propyl) Anilines

The invention discloses a method for the preparation of substituted 4-(heptafluoro-2-propyl) anilines by reaction of 2-bromoheptafluoropropane with anilines in the presence of sodium dithionite, in a solvent and in the presence of a catalyst. 4. The method according to claim 1 , whereinSOLV1 is selected from the group consisting of ethyl acetate, tert-butyl acetate, dimethyl carbonate, acetone, 2-butanone, ethylene glycol, acetonitrile, propionitrile, valeronitrile, 1,4-dioxane, methyl tert-butyl ether, sulfolane, and mixtures thereof.5. The method according to claim 1 , wherein{'sub': 2', '4', '2', '4', '2', '4', '2', '4', '4', '2', '4, 'CAT1 is selected from the group consisting of acetic acid, propionic acid, sulfuric acid, hydrochloric acid, sodium hydrogen sulfate, potassium hydrogen sulfate, tetrabutylammonium hydrogen sulfate, NaHPO, NaHPO, KHPO, KHPO, BuNHPO, pyridinium hydrochloride, toluene sulfonic acid, and mixtures thereof.'} The invention discloses a method for the preparation of substituted 4-(heptafluoro-2-propyl) anilines by reaction of 2-bromoheptafluoropropane with anilines in the presence of sodium dithionite, in a solvent and in the presence of a catalyst.Substituted 4-(heptafluoro-2-propyl) anilines are important intermediates for the preparation of agrochemicals, for example such as Broflanilid with CAS 1207727-04-5.U.S. Pat. No. 4,731,450 describes the perfluoro alkylation of aniline with perfluoroalkyl bromide in a polar aprotic solvent in the presence of zinc and sulfur dioxide. The prominent solvent in the examples is DMF.JP 2003 335735 A discloses a process for producing perfluoroisopropylanilines by a reaction of perfluoroisopropyl bromide with an aniline in the presence of a reaction initiator and a base. The examples disclose only reaction mixtures which have two separate liquid phases, an aqueous phase and a phase formed by an organic solvent. The yield in case of 2-toluidine being the substrate is 32% according to example 2.The use ...

PROCESS FOR THE PREPARATION OF FESOTERODINE

The present invention relates to an improved process for the preparation of Fesoterodine and pharmaceutically acceptable salts thereof. The present invention particularly relates to a process for the preparation of Fesoterodine from O-benzyl tolterodine. 2. A process according to claim 1 , wherein the metal persulphate is selected from the group consisting of sodium persulphate claim 1 , ammonium persulphate or potassium persulphate.3. A process according to claim 1 , wherein said coreductant is selected from the group consisting of dialkylsulphides claim 1 , diaryl sulphides claim 1 , alkyl aryl sulphides claim 1 , dialkylsulfoxides claim 1 , diarylsulfoxides claim 1 , alkylarylsulfoxides claim 1 , mono or poly substituted amines claim 1 , and mono or poly substituted phosphines.4. A process according to claim 3 , wherein said coreductant is dimethyl sulphoxide or dimethyl sulphide.5. The process according to claim 1 , wherein inorganic acid is selected from the group consisting of sulphuric acid claim 1 , hydrochloric acid claim 1 , hydrobromic acid and hydroiodic acid.6. A The process of wherein the metal persulphate is sodium persulphate claim 1 , the organic coreductant is dimethyl sulphoxide and the optional inorganic acid is sulphuric acid.7. (canceled)9. The process according to claim 8 , wherein the metal sulphate is selected from the group consisting of copper sulphate claim 8 , ferrous sulphate claim 8 , zinc sulphate claim 8 , magnesium sulphate claim 8 , and manganese sulphate.10. The process according to claim 8 , wherein metal acetate is selected from the group consisting of sodium acetate claim 8 , potassium acetate claim 8 , magnesium acetate claim 8 , calcium acetate claim 8 , magnesium acetate claim 8 , nickel acetate claim 8 , copper acetate claim 8 , zinc acetate claim 8 , and iron acetate.11. The process according to claim 8 , wherein the metal persulphate is selected from the group consisting of sodium persulphate claim 8 , ammonium ...

METHOD FOR PRODUCING AROMATIC COMPOUND

A method is provided for producing an aromatic compound, including a step of mixing a compound represented by formula (A) and a compound represented by formula (B): 2. The production method of an aromatic compound according to claim 1 , wherein Aand Aare a cyclopentyl group which may have an alkyl group having a number of carbon atoms of 1 to 20 or an aryl group having a number of carbon atoms of 6 to 20 as a substituent.3. The production method of an aromatic compound according to claim 1 , wherein Aand Aare a cyclopentyl group.4. The production method of an aromatic compound according to claim 1 , wherein at least one selected from Rand Ris an alkoxy group having a number of carbon atoms of 1 to 20.5. The production method of an aromatic compound according to claim 1 , wherein R claim 1 , Rand Rare a hydrogen atom.7. The production method of an aromatic compound according to claim 1 , wherein the aprotic organic solvent is at least one selected from the group consisting of ether solvents claim 1 , aromatic hydrocarbon solvents and aliphatic hydrocarbon solvents.8. The production method of an aromatic compound according to claim 1 , wherein the palladium compound is a palladium(0) complex or a palladium(II) complex.10. The phosphine according to claim 9 , wherein Aand Aare a cyclopentyl group which may have an alkyl group having a number of carbon atoms of 1 to 20 or an aryl group having a number of carbon atoms of 6 to 20 as a substituent.11. The phosphine according to claim 9 , wherein Aand Aare a cyclopentyl group.12. The phosphine according to claim 9 , wherein at least one selected from Rand Ris an alkoxy group having a number of carbon atoms of 1 to 20.13. The phosphine according to claim 9 , wherein R claim 9 , Rand Rare a hydrogen atom.15. The phosphonium salt according to claim 14 , wherein Aand Aare a cyclopentyl group which may have an alkyl group having a number of carbon atoms of 1 to 20 or an aryl group having a number of carbon atoms of 6 to 20 as a ...

DEHYDROXYLATION OF AMINOALCOHOLS TO ALKYL AMINES

The present invention provides a process for producing alkyl amines by dehydroxylation of aminoalcohols. This provides an alternate reaction route for making alkyl amines, such as 2-methylpropane-2-amine and its derivatives.

Process for manufacturing ethylene amines

A process for preparing polyethyleneamines of formula NH2-(CH2-CH2-NH-)pH wherein p is at least 3 and wherein one or more —NH-CH2-CH2-NH— units may be piperazine units and/or ethylene urea derivatives of these compounds, includes reacting monoethylene glycol with an amine-functional compound having at least two —NH— units, of which at least one is selected from primary amine groups and cyclic secondary amine groups, in the presence of a carbon oxide-delivering agent. The amine-functional compound includes at least one —NH-CH2-CH2-NH— unit, and one or more —NH-CH2-CH2-NH— units may be in the form of cyclic ethylene urea moieties, piperazine moieties, or linear ethylene urea moieties. The molar ratio of amine-functional compound to monoethylene glycol is above 1.2:1 and the molar ratio of carbon oxide delivering agent to —NH-CH2-CH2-NH— units is at least 0.5:1. The process makes it possible to obtain ethylene amines and derivatives thereof without using ammonia or metal-containing catalysts.

DRILLING FLUID ADDITIVE COMPOSITION, AND OIL-BASED DRILLING FLUID AND USE THEREOF

The present invention relates to the well drilling field in petroleum industry, in particular to a drilling fluid additive composition that contains a lubricant, an emulsifier, and a rheological modifier, wherein, the lubricant contains: graphite oxide and a biquaternary ammonium salt compound in which the cation part is represented by formula (1); the emulsifier is one or more of compounds represented by formula (I); the rheological modifier is a dimer acid-organic amine copolymer comprising structural units from dimer acid, structural units from alkylamine and structural units from arylamine. The present invention further provides an oil-based drilling fluid containing the composition and a use thereof. The oil-based drilling fluid containing the composition provided in the present invention obtains a lower lubrication coefficient, and favorable rheological property and thermostability, and is suitable for use in operation at a high temperature. 2. The composition according to claim 1 , wherein the weight ratio of the lubricant to the emulsifier to the rheological modifier is 100:300-800:50-200.3. The composition according to claim 2 , wherein the weight ratio of the lubricant to the emulsifier to the rheological modifier is 100:300-500:50-100.4. The composition according to claim 1 , wherein claim 1 , in the lubricant claim 1 , each Rgroup is independently selected from H claim 1 , hydroxyl claim 1 , halogen claim 1 , C1-C4 alkyl claim 1 , C1-C4 alkoxy claim 1 , and C1-C4 hydroxyalkyl; each Rgroup is independently selected from H and C1-C4 alkyl; and each Rgroup is independently selected from H claim 1 , C1-C15 alkyl claim 1 , and C1-C15 hydroxyalkyl.5. The composition according to claim 4 , wherein claim 4 , in the lubricant claim 4 , each Rgroup is independently selected from H claim 4 , hydroxyl claim 4 , methyl claim 4 , ethyl claim 4 , methoxy claim 4 , ethoxy claim 4 , hydroxymethyl claim 4 , and hydroxyethyl; each Rgroup is independently selected from H ...

MANUFACTURING PROCESS FOR MEMANTINE

A method for manufacturing 3,5-dimethyl-1-adamantanamine of the present invention comprises: (i) a step of reacting 3,5-dimethyl-1-adamantanol with an acid and nitrile in an organic solvent to obtain a reaction solution; (ii) a step of adding water to the reaction solution obtained in step (i) to obtain 1-amido-3,5-dimethyladamantane; and (iii) a step of hydrolyzing 1-amido-3,5-dimethyladamantane obtained in step (ii) in the presence of an alcohol-containing solvent and an inorganic base. 1. A method for manufacturing 3 ,5-dimethyl-1-adamantanamine , comprising:(i) a step of reacting 3,5-dimethyl-1-adamantanol with an acid and nitrile in an organic solvent to obtain a reaction solution;(ii) a step of adding water to the reaction solution obtained in step (i) to obtain 1-amido-3,5-dimethyladamantane; and(iii) a step of hydrolyzing 1-amido-3,5-dimethyladamantane obtained in step (ii) in the presence of an alcohol-containing solvent and an inorganic base.2. The method according to claim 1 , wherein the organic solvent used in step (i) is hydrophobic.3. The method according to claim 1 , wherein the organic solvent used in step (i) contains at least one organic solvent selected from the group consisting of an aliphatic hydrocarbon and an aromatic hydrocarbon.4. The method according to claim 1 , wherein the alcohol-containing solvent used in step (iii) contains at least one alcohol selected from monovalent linear primary alcohols.5. The method according to claim 1 , wherein the alcohol-containing solvent used in step (iii) contains at least one alcohol selected from the group consisting of 1-butanol claim 1 , 1-pentanol claim 1 , 1-hexanol claim 1 , 1-heptanol claim 1 , and 1-octanol.6. The method according to claim 1 , wherein a molar ratio of the acid to 3 claim 1 ,5-dimethyl-1-adamantanol in step (i) is 1 to 10.7. The method according to claim 1 , wherein a molar ratio of the nitrile to 3 claim 1 ,5-dimethyl-1-adamantanol in step (i) is 1 to 10.8. The method according ...

METHOD FOR PRODUCING TRANS-RICH-1,4-BIS(AMINOMETHYL)CYCLOHEXANE

The method for producing trans-rich-1,4-bis(aminomethyl)cyclohexane includes blending 1,4-bis(aminomethyl)cyclohexane with an alkali metal compound and XDA and heating the mixture to isomerize 1,4-bis(aminomethyl)cyclohexane so that the trans isomer content relative to the cis/trans isomers in total is more than 70 mass %, and purifying the isomerized 1,4-bis(aminomethyl)cyclohexane by distillation after the isomerization step. The alkali metal compound is at least one compound selected from the group consisting of alkali metal hydride, alkali metal amide, and alkyl alkali metal. In the isomerization step, 0.01 mol or more and less than 4 mol of XDA is blended relative to 100 mol of 1,4-bis(aminomethyl)cyclohexane, a dimer produced from one molecular of 1,4-bis(aminomethyl)cyclohexane and one molecular of XDA, and a trimer produced from two molecules of 1,4-bis(aminomethyl)cyclohexane and one molecular of XDA are produced, and the dimer content is 5 mass % or more and less than 75 mass % relative to the dimer and trimer in total. 1. A method for producing trans-rich-1 ,4-bis(aminomethyl)cyclohexane , the method comprising the steps of:blending 1,4-bis(aminomethyl)cyclohexane with an alkali metal compound and xylylenediamine and heating the mixture to isomerize 1,4-bis(aminomethyl)cyclohexane so that the trans isomer content relative to the cis isomer and trans isomer in total is more than 70 mass %,purifying, after the isomerization step, the isomerized 1,4-bis(aminomethyl)cyclohexane by distillation,wherein the alkali metal compound is at least one compound selected from the group consisting of alkali metal hydride, alkali metal amide, and alkyl alkali metal, '0.01 mol or more and less than 4 mol of xylylenediamine is blended relative to 100 mol of 1,4-bis(aminomethyl)cyclohexane, and', 'in the isomerization step,'} wherein the dimer is produced from one molecular of 1,4-bis(aminomethyl)cyclohexane and one molecular of xylylenediamine, and', 'the trimer is produced ...

Two-step process for converting cyclic alkylene ureas into their corresponding alkylene amines

A process is provided for converting cyclic alkyleneureas into their corresponding alkyleneamines. The process includes, in a first step, converting cyclic alkyleneureas into their corresponding alkyleneamines by reacting cyclic alkyleneureas in the liquid phase with water with removal of CO2, so as to convert from about 5 mole % to about 95 mole % of alkyleneurea moieties in the feedstock to the corresponding amines. The process further includes, in a second step, adding an inorganic base and reacting cyclic alkylene ureas remaining from the first step with the inorganic base to convert them partially or completely into their corresponding alkyleneamines. Certain embodiments of the two-step process obtain a high conversion of cyclic alkyleneureas, while using substantially less strong inorganic base. Certain embodiments of the process process also show a higher selectivity to amines than prior art processes.

REACTIVE SEPARATION PROCESS TO CONVERT CYCLIC ALKYLENE UREAS INTO THEIR CORRESPONDING ALKYLENE AMINES

A process to convert cyclic alkylene ureas into their corresponding alkylene amines is provided. An exemplary process includes reacting the cyclic alkylene ureas with an amine compound chosen from the group of primary amines or secondary amines that have a higher boiling point than the alkylene amines formed during the process, wherein the process is a reactive separation process and the reaction mixture contains less than about 10 wt % of water on the basis of total weight of the reaction mixture. 1. A process to convert a cyclic alkylene urea into a corresponding alkylene amines , the process comprising reacting the cyclic alkylene ureas with an amine compound chosen from the group of primary amines or secondary amines that have a higher boiling point than the alkylene amines formed during the process , wherein the process is a reactive separation process and the reaction mixture contains less than about 10 wt % of water on the basis of total weight of the reaction mixture.2. The process of wherein the cyclic alkylene urea and the amine compound react in accordance with the reaction UEA1+EA2->EA1↑+UEA2 claim 1 , wherein the cyclic alkylene urea is UEA1 and the amine compound is EA2 and the amine compound EA2 has a higher boiling point than the amine EA1 formed in the process.4. The process of wherein the amine compound is a compound that can bind the carbonyl group from the cyclic alkylene urea to give another linear or cyclic alkylene urea or linear or cyclic alkylene carbamate.5. The process of wherein the amine compound is an alkylene amine or an alkanol amine compound that is larger than the one derived from the starting cyclic alkylene urea after the conversion.7. The process of wherein the reaction is done in less than about 7 wt % of water on total reaction mixture.8. The process of wherein the reaction is done at a pressure that is less than about 25 bara.9. The process of wherein the reaction is done at a pressure that is less than about 500 mbara.10. The ...

METHOD FOR PREPARING PRIMARY DIAMINES BY KOLBE ELECTROLYSIS COUPLING REACTION

The present invention relates to a method for preparing primary diamines from amino acid compounds. Specifically, this invention is related to the preparation of a primary diamine from an amino acid and/or its salt by Kolbe electrolysis coupling reaction. 2. The method according to claim 1 , wherein T represents a linear or branched C-Calkylene group.3. The method according to claim 1 , wherein the primary diamine is selected from the group consisting of 1 claim 1 ,10-decanediamine claim 1 , 1 claim 1 ,8-octanediamine claim 1 , 1 claim 1 ,6-hexanediamine claim 1 , 1 claim 1 ,4-butanediamine and 1 claim 1 ,2-ethylenediamine.4. The method according to claim 1 , wherein the amino acid compound is selected from the group consisting of 6-aminohexanoic acid claim 1 , 5-aminopentanoic acid claim 1 , 4-aminobutanoic acid claim 1 , 3-aminopropanoic acid and aminoacetic acid.5. The method according to claim 1 , wherein the concentration of the amino acid compound in the reaction medium is from 0.05 to 2 mol/L.6. The method according to claim 1 , wherein the solvent is selected from the group consisting of methanol claim 1 , ethanol claim 1 , propanol claim 1 , acetone claim 1 , acetonitrile claim 1 , THF (tetrahydrofuran) claim 1 , DMF (N claim 1 ,N-dimethylformamide) claim 1 , DMSO (dimethylsulfoxide) claim 1 , NMP (N-Methyl-2-pyrrolidone) claim 1 , DMC (dimethyl carbonate) claim 1 , NM (nitromethane) claim 1 , PC (propylene carbonate) claim 1 , EC (ethylene carbonate) claim 1 , toluene claim 1 , xylene claim 1 , dimethylformamide claim 1 , hexane claim 1 , pentane claim 1 , heptane claim 1 , octane claim 1 , nonane claim 1 , decane claim 1 , undecane claim 1 , dodecane and ionic liquids.7. The method according to claim 6 , wherein the solvent is methanol or ethanol.8. The method according to claim 1 , wherein the electrolyte is a base electrolyte.9. The method according to claim 8 , wherein the electrolyte is an alkoxide.10. The method according to claim 9 , wherein the ...

NEW CATIONIC QUATERNARY AMMONIUM COMPOUNDS AND COMPOSITIONS COMPRISING SAME AND PROCESSES FOR THEIR MANUFACTURE

The present invention concerns new cationic quaternary ammonium compounds which exhibit excellent adsorption properties on negatively charged surfaces. These ones can notably be obtained firstly by reacting an internal ketone with a twin-tail amine under reductive amination conditions to obtain a twin tail triamine, then subjecting the twin tail triamine to a quaternization reaction. They can also obtained be obtained by the quaternization reaction of a certain diamine. 2. The compound of formula (I) or (II) in accordance with claim 1 , wherein Xand Xare —(CH)— with m being an integer equal to 2 to 20 and Rto Rare hydrogen or an alkyl group with 1 to 6 carbon atoms.3. The compound in accordance with wherein Xand Xare —(CH)— and Rto Rare methyl.4. The compound of formula (I) or (II) in accordance with claim 1 , wherein Xand Xare a branched divalent hydrocarbon group claim 1 , which may be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups and Rto Rare as defined.5. The compound of formula (I) or (II) in accordance with claim 1 , wherein Xand Xare a branched or linear divalent hydrocarbon group containing 2 to 20 carbon atoms substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups and Rto Rare as defined.6. The compound of formula (I) or (II) in accordance with claim 1 , wherein Xand Xare a divalent aliphatic group containing 2 to 20 carbon atoms with the exception of —(CH)— and Rto Rare as defined in .7. The compound of formula (I) or (II) in accordance with claim 1 , wherein X claim 1 , X claim 1 , R claim 1 , and Rare as defined in and Rto Rare a C-Calkyl group.8. A composition comprising a compound of formula (II) as defined in and at least one compound of formula (III) or (IV) as defined in .9. The composition in accordance with claim wherein the composition comprises at least one compound of each of formulae (II) to (IV).10. The composition in accordance with claim 9 , wherein ...

Process for converting trans-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine to cis-n-methyl-4- (3,4-di- chlorophenyl)-1,2,3,4- tetrahydro-1- naphthaleneamine

A novel process for converting trans-isomeric N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine to cis-isomeric N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine is disclosed. The process involves contacting trans-isomeric N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine, or a mixture of same with up to about an equal part by weight of the corresponding cis-isomer, with a basic equilibration agent like potassium tert.-butoxide in a reaction-inert polar organic solvent to ultimately afford a cis/trans-mixture wherein the amount of cis-amine present in said mixture achieves a constant value of about 2:1 on a weight-by-weight basis. The aforesaid resultant mixture is useful as an intermediate product that ultimately leads to pure cis-(1S) (4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenea mine (sertraline), which is a known antidepressant agent.

Continuous Ni/low A1 catalyzed hydrogenation of aromatic nitro compounds

Nitrated aromatic compounds are continuously catalytically hydrogenated into their corresponding aromatic amines in the presence of an effective amount of a nickel or nickel/aluminum catalyst, the nickel catalyst being essentially devoid of aluminum values and the nickel/aluminum catalyst containing up to 5.5% by weight of aluminum values; the subject hydrogenation is thus conducted under conditions such as to limit the formation of nickel aluminates and the nickel or nickel/aluminum catalyst is continuously catalytically active for at least three days.

The production of formate salts of nitrogenous bases

A formate salt of a nitrogenous base is produced by reacting hydrogen and carbon dioxide with a nitrogenous base in a multi-liquid phase in the presence of a catalyst comprising an inorganic or organometallic compound of a metal of Group VIII of the Periodic Table and a compound of an element of either Group VA or Group VIA of the Periodic Table of the Elements.

Process for the telomerization of non-cyclic olefins

Verfahren zur Telomerisation von nicht cyclischen Olefinen mit mindestens zwei konjugierten Doppelbindungen mit mindestens einem Nucleophil unter Verwendung eines ein Metall der 8., 9. oder 10. Gruppe des Periodensystems der Elemente aufweisenden Katalysators, welches dadurch gekennzeichnet ist, dass der Gesamtprozess der Telomerisation einen Verfahrensschritt der Katalysatorrückführung aufweist, indem dem in diesem Verfahrensschritt vorliegenden Gemisch über eine Wasserstoffquelle Wasserstoff zugeführt wird. A process for the telomerization of non-cyclic olefins having at least two conjugated double bonds with at least one nucleophile using a catalyst comprising a metal of the 8th, 9th or 10th group of the Periodic Table of the Elements, characterized in that the overall process of telomerization is a process step the catalyst recycling comprises, by supplying hydrogen to the mixture present in this process step via a hydrogen source.

Processo para a produção de aminas aromáticas e catalisador

process for the production of one or more ethylene amines by a transamination reaction

Procedimento per l'lachilazione di ammine secondarie alifatiche

Process for the alkylation of secondary aliphatic amines in the presence of an amide of a transition metal

A process for the alkylation of secondary aliphatic amines is provided which consists of reacting a secondary aliphatic amine with at least one hydrogen on the alpha carbon atom of the amino group with an olefine in the presence of an amide of a transition metal.

Process for the preparation of a dry suspension of an ammonium halide