Forming Amine Group Of Alicyclic Ring Containing Compound Directly By Reduction Patents (Class 564/448)
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Patent number: 6528687Abstract: A process for the preparation of an enantiomerically enriched chiral amine of formula (10), or the opposite enantiomer thereof, from an inline of formula (11) wherein (i) R1 is aryl, R2 is alkyl and R3 is aryl or aryl-CH2—, or (iii) R2 is linked with R1 and/or R3 to form one or more rings and R3 or R1 (if not in a ring) is H or a non-interfering organic group, the number of C atoms in each of R1, R2 and R3 being up to 30, comprises asymmetric hydrogenation of the imine in the presence of a base and, as catalyst, a ruthenium complex of a chiral diphosphine and a chiral diamine.Type: GrantFiled: July 23, 2001Date of Patent: March 4, 2003Assignee: Chirotech Technology LimitedInventors: Christopher James Cobley, Julian Paul Henschke, James Andrew Ramsden
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Patent number: 6525223Abstract: Secondary amines of the formula (II) (X—CH2—)2NH (II) where X is a C1-20-alkyl, C2-20-alkenyl or C3-8-cycloalkyl group which may be unsubstituted or substituted by C1-20-alkyl, C3-8-cycloalkyl, C4-20-alkylcycloalkyl, C4-20-cycoalkylalkyl, C2-20-alkoxyalkyl, C6-14-aryl, C7-20-alkylaryl, C7-20-aralkyl, C1-20-alkoxy, hydroxy, C1-20-hydroxyalkyl, amino, C1-20-alkylamino, C2-20-dialkylamino, C2-12-alkenylamino, C3-8-cycloalkylamino, arylamino, diarylamino, aryl-C1-8-alkylamino, halogen, mercapto, C2-20-alkenyloxy, C3-8-cycloalkoxy, aryloxy and/or C2-8-alkoxycarbonyl, are prepared by reacting nitriles of the formula (III) X—CN (III) with hydrogen at from 20 to 250° C. and pressures of from 60 to 350 bar in the presence of an Rh-containing catalyst comprising from 0.Type: GrantFiled: December 27, 2001Date of Patent: February 25, 2003Assignee: BASF AktiengesellschaftInventors: Joachim Pfeffinger, Michael Hüllmann, Arthur Höhn, Frank Funke, Frank Ohlbach, Till Gerlach
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Patent number: 6521564Abstract: A process for the modification of a hydrogenation catalyst of the Raney nickel, Raney cobalt, nickel-on-carrier or cobalt-on-carrier type, which process includes treating the hydrogenation catalyst at temperatures of about 0° C. to about 120° C. with carbon monoxide, carbon dioxide, formaldehyde, a lower aliphatic aldehyde, an aromatic aldehyde, an aliphatic ketone, an aromatic ketone, a mixed aliphatic/aromatic ketone, glyoxal, pyruvaldehyde or glyoxylic acid as the modification agent in a liquid dispersion medium consisting of water or an organic solvent for a duration of about 15 minutes to about 24 hours. When the thus-modified catalyst is used in the hydrogenation of a nitrile to the corresponding amine, the selectivity is increased, and significantly favors the amount of the primary amine vis-à-vis the undesired secondary amine in the hydrogenation product as compared to when the corresponding unmodified catalyst is employed.Type: GrantFiled: November 30, 2000Date of Patent: February 18, 2003Assignee: Roche Vitamins, Inc.Inventors: Oliver Gerald Degischer, Felix Roessler
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Publication number: 20020137970Abstract: Process for the preparation of isophorone diamine from isophorone nitrile, isophorone nitrilimine or mixtures containing isophorone nitrile and/or isophorone nitrilimine by hydrogenation through to amine in the presence of at least ammonia, hydrogen and a formed Raney hydrogenation catalyst based on cobalt, nickel, copper and/or iron, wherein the Raney catalyst is present in the form of hollow bodies.Type: ApplicationFiled: December 19, 2001Publication date: September 26, 2002Inventors: Daniel Ostgard, Monika Berweiler, Stefan Roder, Jorg Sauer, Bernd Jaeger, Norbert Finke, Christian Lettmann
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Patent number: 6448402Abstract: The invention relates to a novel process for the preparation of an aminoalcohol of the formula racemically or optically active, starting from 2-azabicyclo[2.2.1]hept-5-en-3-one, its further conversion to give the corresponding acyl derivative and its further conversion to (1S,4R)— or (1R,4S)-4-(2-amino-6-chloro-9-H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formulae In the latter synthesis, the aminoalcohol is converted into the corresponding D- or L-tartrate, which is then reacted with N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide of the formula to give (1S,4R)— or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentenyl-1-methanol of the formulae and then cyclized to give the end compounds.Type: GrantFiled: January 30, 2001Date of Patent: September 10, 2002Assignee: Lonza AGInventors: Walter Brieden, Josef Schröer, Christine Bernegger-Egli, Eva Maria Urban, Michael Petersen, Jean-Paul Roduit, Katja Berchtold, Holger Breitbach
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Patent number: 6448445Abstract: The invention relates to a method for disubstituting carboxylic acid amides on the geminal carbonyl-C-atom using at least one grignard reagent in the presence of a metal alcoholate compound used as a catalyst and in the presence of another organometallic compound used as a co-catalyst.Type: GrantFiled: February 23, 2001Date of Patent: September 10, 2002Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Herwig Buchholz, Urs Welz-biermann, Armin Meijere
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Patent number: 6437186Abstract: Process for the preparation of isophorone diamine from isophorone nitrile, isophorone nitrilimine or mixtures containing isophorone nitrile and/or isophorone nitrilimine by hydrogenation through to amine in the presence of at least ammonia, hydrogen and a formed Raney hydrogenation catalyst based on cobalt, nickel, copper and/or iron, wherein the Raney catalyst is present in the form of hollow bodies.Type: GrantFiled: December 19, 2001Date of Patent: August 20, 2002Assignee: Degussa AGInventors: Daniel Ostgard, Monika Berweiler, Stefan Roder, Jorg Sauer, Bernd Jaeger, Norbert Finke, Christian Lettmann
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Publication number: 20020010371Abstract: An improved process for the preparation of a cyclic amino acid by a novel synthesis is described where benzonitrile is treated with an alkali metal and an amine under Birch reduction conditions to generate in situ an anionic intermediate which is alkylated with an &agr;-haloacetic acid moiety which is subsequently converted to the desired product, as well as valuable intermediates used in the process.Type: ApplicationFiled: March 16, 2001Publication date: January 24, 2002Inventors: Carl Francis Deering, Kenneth Earl Mennen, Robert Ramage
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Patent number: 6297394Abstract: A material useful as catalyst for the hydrogenation of alpha, Omega-dinitriles comprises a) iron or a compound based on iron or mixtures thereof, (b) from 0.001 to 0.3% by weight based on (a) of a promoter based on 2, 3, 4 or 5 elements selected from the group consisting of aluminum, silicon, zirconium, titanium and vanadium, (c) from 0 to 0.3% by weight based on (a) of a compound based on an alkali and/or alkaline earth metal, and also (d) from 0.001 to 1% by weight based on (a) of manganese.Type: GrantFiled: August 23, 2000Date of Patent: October 2, 2001Assignee: BASF AktiengesellschaftInventors: Guido Voit, Rolf Fischer, Peter Bassler, Andreas Ansmann, Hermann Luyken, Martin Merger, Frank Ohlbach, Alwin Rehfinger
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Patent number: 6262309Abstract: Disclosed is a process for producing norbornane dimethylene amines wherein norbornane dicarbonitriles are hydrogenated by using a Raney cobalt catalyst containing manganese etc. in the presence of water in an amount of 0.1 to 1.5 moles per mole of the norbornane dicarbonitriles.Type: GrantFiled: September 22, 2000Date of Patent: July 17, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Isao Fukada, Seiichi Ishii, Hiroharu Kageyama, Hiroki Mizutani
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Publication number: 20010004672Abstract: A process for the modification of a hydrogenation catalyst of the Raney nickel, Raney cobalt, nickel-on-carrier or cobalt-on-carrier type, which process includes treating the hydrogenation catalyst at temperatures of about 0° C. to about 120° C. with carbon monoxide, carbon dioxide, formaldehyde, a lower aliphatic aldehyde, an aromatic aldehyde, an aliphatic ketone, an aromatic ketone, a mixed aliphatic/aromatic ketone, glyoxal, pyruvaldehyde or glyoxylic acid as the modification agent in a liquid dispersion medium consisting of water or an organic solvent for a duration of about 15 minutes to about 24 hours. When the thus-modified catalyst is used in the hydrogenation of a nitrile to the corresponding amine, the selectivity is increased, and significantly favors the amount of the primary amine vis-à-vis the undesired secondary amine in the hydrogenation product as compared to when the corresponding unmodified catalyst is employed.Type: ApplicationFiled: November 30, 2000Publication date: June 21, 2001Inventors: Oliver Gerald Degischer, Felix Roessler
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Patent number: 6156933Abstract: Process for the selective hydrogenation of alphatic or aromatic substrates under supercritical or near critical conditions. Hydrogenation is effected using a heterogeneous catalyst in a continuous flow reactor containing a supercritical or near critical reaction medium and selectively of product formation is achieved by varying one or more of the temperature, pressure, catalyst and flow rate.Type: GrantFiled: February 18, 1999Date of Patent: December 5, 2000Assignees: Degussa-Huls AG, Thomas Swan & Co. Ltd.Inventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland
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Patent number: 6153748Abstract: A process for hydrogenating a compound in the group of the imines or enamines I to an amine II in the presence of a nitrile III, said nitrile III being essentially not hydrogenated comprises reacting a mixture comprising a compound I and a nitrile III with a gas comprising molecular hydrogen in the presence of a catalyst IV.Type: GrantFiled: August 9, 1999Date of Patent: November 28, 2000Assignee: BASF AktiengesellschaftInventors: Eberhard Fuchs, Frank Ohlbach
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Patent number: 6022999Abstract: A process for the preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine having a cis/trans isomer ratio of at least 70:30 bya) imination of 3-cyano-3,5,5-trimethylcyclohexanone with ammonia in the presence of an imination catalyst at temperatures of from 20.degree. to 150.degree. C. and pressures of from 1.5 to 30 MPa to form 3-cyano-3,5,5-trimethylcyclo-hexanone imine followed byb) hydrogenation of the 3-cyano-3,5,5-trimethylcyclohexanone imine in the presence of ammonia over a catalyst containing copper and/or a Group VIII metal at a temperature of from 80.degree. to 160.degree. C. and under a pressure of from 5 to 30 MPa,wherein the catalytic hydrogenation of the 3-cyano-3,5,5-trimethylcyclohexanone imine is carried out in the presence of an acid used in an amount such as to give an acid number of from 0.1 to 2, based on 3-cyano-3,5,5-trimethylcyclohexanone used.Type: GrantFiled: December 9, 1998Date of Patent: February 8, 2000Assignee: BASF AktiengesellschaftInventors: Guido Voit, Tom Witzel, Boris Breitscheidel, Hermann Luyken, Karl-Heinz Ross, Peter Wahl
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Patent number: 6011179Abstract: A process for the production of primary and/or secondary amines from imines or nitriles, comprising an aminating hydrogenation of imine or of nitrile with hydrogen in the presence of ammonia, of a hydrogenation catalyst based on cobalt, nickel, ruthenium or mixtures of these metals and of a base, at a temperature within the range of 50.degree. C. to 200.degree. C. and at a pressure within the range of 0.3 to 30 MPa. The yield of amine is increased by the use of a quaternary ammonium hydroxide as base. Preferably a tetraalkylammonium hydroxide is used in a quantity of from 0.01 to 100 mMol per mol of amine or of nitrile. The process is suitable in particular for the production of isophoronediamine from isophorone nitrile imine.Type: GrantFiled: October 30, 1998Date of Patent: January 4, 2000Assignee: Degussa-Huls AGInventors: Thomas Haas, Karl Ludwig Weber, Klaus Stadtmuller, Willi Hofen, Rudolf Vanheertum
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Patent number: 5986139Abstract: A process for the preparation of primary or secondary amines by hydrogenation of imines with hydrogen at elevated pressure and in the presence of a dinuclear Ir(III) complex having ditertiary diphosphine ligands, halide bridges, halide and hydride ligands, or an Ir(III) halide complex salt containing ditertiary diphosphine ligands, as catalyst, wherein the catalyst corresponds to formula I or Ia or to mixtures of at least two compounds of formula I, at least two compounds of formulae I and Ia, or at least two compounds of formula Ia[(DIP)IrX.sub.q Y.sub.r ].sub.2 (I),[(DIP)X.sub.4 ].sup..crclbar. Me.sup..sym. (Ia),whereinDIP is the ditertiary diphosphine ligand of a ferrocenyldiphosphine the phosphine groups of which are either bonded directly or via a bridge group --CR.sub.v R.sub.w -- to the ortho positions of a cyclopentadienyl ring or are each bonded to a cyclopentadienyl ring of a ferrocenyl, so that a 5-, 6- or 7-membered ring is formed together with the Ir atom;R.sub.v and R.sub.Type: GrantFiled: January 26, 1998Date of Patent: November 16, 1999Assignee: Novartis Crop Protection, Inc.Inventors: Rafael Sablong, John Anthony Osborn, Felix Spindler
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Patent number: 5905170Abstract: The present invention relates to a process for the production of 1-amino-1-methyl-3(4)-aminomethylcyclohexane bya) simultaneously reacting 4(5)-aminomethyl-1-methylcyclohexene (CMA), hydrocyanic acid and aqueous sulphuric acid at temperatures of 60.degree. C. to 120.degree. C., preferably 80.degree. C. to 120.degree. C. to form 1-formamido-1-methyl-3(4)-aminomethylcyclohexane (FMA) in a first stage,b) adding water and hydrolyzing 1-formamido-1-methyl-3 (4)-aminomethylcyclohexane (FMA) and unreacted hydrocyanic acid in a second stage andc) adding a base and isolating 1-amino-1-methyl-3 (4)-aminomethylcyclohexane (AMCA) by extraction from the reaction mixture obtained in the second stage of the reaction, optionally after removing of formic acid.Type: GrantFiled: March 11, 1998Date of Patent: May 18, 1999Assignee: Bayer AktiengesellschaftInventors: Konrad Fischer, Oswald Wilmes, Dieter Arlt, Carl Casser, Peter Maas, Pierre Woestenborghs, Theo Van der Knaap
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Patent number: 5900507Abstract: The present invention relates to a process for the preparation of 1-amino-1-methyl-3(4)-aminomethyl cyclohexane (AMCA) bya) catalytically hydrogenating 1-formamido-1-methyl-3(4)-cyano cyclohexane (FMC) in a first reaction stage to form 1-formamido-1-methyl-3(4)-aminomethyl cyclohexane (FMA), 1-amino-1-methyl-3(4)-formamidomethyl cyclohexane (AMF), 1-formamido-1-methyl-3(4)-formamidomethyl cyclohexane (FMF) and/or AMCA, andb) reacting FMA, AMF and/or FMF in a second reaction stage with an alkaline compound to from AMCA and a formic acid derivative, andc) separating the reaction mixture obtained in step b) into components by fractional distillation and/or by crystallization and filtration.The present invention is also relates to carrying the hydrogenation reaction of step a) in the presence of a formulating agent to form 1-formamido-1-methyl-3(4)-formamidomethyl cyclohexane (FMF).Type: GrantFiled: March 11, 1998Date of Patent: May 4, 1999Assignee: Bayer AktiengesellschaftInventors: Konrad Fischer, Oswald Wilmes, Dieter Arlt, Carl Casser, Peter Maas, Pierre Woestenborghs, Theo Van Der Knaap, Raf Reintjens
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Patent number: 5874625Abstract: An improved, optimized industrial process has been found for the hydrogenation of organic nitrites into primary amines, which essentially consists of contacting a dried charge of at least one organic nitrile, aqueous alkali metal hydroxide, at least one Raney slurry hydrogenation catalyst, water and hydrogen for an effective time and at an effective temperature and pressure, wherein the improvements comprise eliminating the steps of drying the charge and adding water and reducing the required water to about 0.2%. Secondary and tertiary amine formation is low, as is moisture content and neither precious metals such as rhodium, nor strategic metals, such as cobalt nor ammonia gas nor solvents are required. Surprisingly, it has been found that water levels less than that taught in the prior art are effective at suppressing secondary and tertiary amine production, while still producing repeatable product on an industrial scale and with reduced cycle time, energy and catalyst charge.Type: GrantFiled: November 4, 1996Date of Patent: February 23, 1999Assignee: Henkel CorporationInventor: A. Fred Elsasser
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Patent number: 5852217Abstract: This invention relates to a process for the production of primary and/or secondary amines from oxo compounds by catalytic imination of the oxo compound with ammonia or a primary amine and subsequent hydrogenation. Imination proceeds according to the invention in the presence of a novel imination catalyst, namely an organopolysiloxane containing sulphonate groups. This imination catalyst is distinguished by elevated activity. The process is in particular suitable for the production of isophorone diamine from isophorone nitrile, wherein it has proved possible to reduce the content of secondary products and to increase yield.Type: GrantFiled: July 7, 1997Date of Patent: December 22, 1998Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Dietrich Arntz, Karl-Ludwig Weber, Willi Hofen, Stefan Wieland
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Patent number: 5789621Abstract: A process for preparing an NH.sub.2 -containing compound by hydrogenating a compound containing at least one unsaturated carbon-nitrogen bond with hydrogen in the presence of a catalyst at temperatures not below room temperature and elevated hydrogen partial pressure in the presence or absence of a solvent which process includes the following steps:a) using a catalyst comprising a cobalt- and/or iron-containing catalyst, andb) after the conversion based on the compound to be hydrogenated and/or the selectivity based on the desired product has or have dropped below a defined value or the amount of an unwanted by-product has risen beyond a defined value, interrupting the hydrogenation by stopping the feed of the compound to be hydrogenated and of the solvent, if used,c) treating the catalyst at from 150.degree. to 400.degree. C. with hydrogen using a hydrogen pressure within the range from 0.Type: GrantFiled: August 8, 1996Date of Patent: August 4, 1998Assignee: BASF AktiengesellschaftInventors: Werner Schnurr, Guido Voit, Klemens Flick, Rolf-Hartmuth Fischer
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Patent number: 5756845Abstract: A process for the preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine from 3-cyano-3,5,5-trimethylcyclohexanone which requires three spatially separated reaction spaces, in order to carry out the following three steps in sequence:a) reacting the 3-cyano-3,5,5-trimethylcyclohexanone with excess ammonia on acidic metal-oxide catalysts in a first reaction space at from 20.degree. to 150.degree. C. and from 50 to 300 bar,b) hydrogenating the resultant reaction products using hydrogen in a second reaction space in the presence of excess ammonia and preferably liquid ammonia on hydrogenation catalysts, optionally using basic components or on neutral or basic supports at from 50.degree. to 100.degree. C. and at from 50 to 300 bar, andc) hydrogenating the resultant reaction products in the presence of hydrogen and also ammonia in a third reaction space on hydrogenation catalysts, optionally using basic components or on neutral or basic supports at from 110.degree. to 160.degree. C. and at from 150 to 300 bar.Type: GrantFiled: February 28, 1996Date of Patent: May 26, 1998Assignee: BASF AktiengesellschaftInventors: Guido Voit, Tom Witzel, Boris Breitscheidel, Wolfgang Harder, Hermann Luyken, Axel Paul, Karl-Heinz Ross, Peter Wahl
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Patent number: 5750788Abstract: A process is disclosed for preparing amines by hydrogenating compounds with at least 3 cyano groups prepared by adding acrylonitrile to ammonia or primary amines at temperatures from 80.degree. to 200.degree. C. and pressures from 5 to 500 bars.Type: GrantFiled: May 19, 1997Date of Patent: May 12, 1998Assignee: BASF AktiengesellschaftInventors: Lukas Haussling, Horst Neuhauser, Wolfgang Paulus
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Patent number: 5728873Abstract: A process for the preparation of cyclopropanamine by Hofmann degradation of cyclopropanecarboxamide, comprising the following steps:(1) suspending cyclopropanecarboxamide, either (A) in 1.1 to 4 mol of sodium hydroxide, in solution whose concentration is 10 to 50%, per mol of amide, or (B) in a sparing amount of water,(2) adding 1 to 1.5 mol of hypochlorite, per mol of amide, from a 5 to 15% strength hypochlorite solution at a temperature of 0.degree. to 20.degree. C.,(3) adding 1.1 to 4 mol of sodium hydroxide, in solution whose concentration is 10 to 50%, per mol of amide, in the case where a suspension has been formed according to step (1)(B),(4) reacting the amide, hypochlorite, and sodium hydroxide for 10 to 60 minutes to form a homogeneous reaction mixture,(5) continuously passing the homogeneous reaction mixture through a tubular reactor at a temperature of 45.degree. to 260.degree. C.Type: GrantFiled: June 14, 1996Date of Patent: March 17, 1998Assignee: Huels AktiengesellschaftInventors: Wolfgang Kleemiss, Thomas Kalz
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Patent number: 5705699Abstract: 3-Aminomethyl-3,5,5-trimethylcyclohexylamine is prepared by reacting 3-cyano-3,5,5-trimethylcyclohexanone with 3-aminomethyl-3,5,5-trimethylcyclohexylamine and subsequently or simultaneously adding ammonia under a hydrogen pressure of from 50 to 300 bar in the presence of a hydrogenation catalyst at from 20.degree. to 150.degree. C., by a process in which the reaction is carried out without removing the water of reaction.Type: GrantFiled: February 28, 1995Date of Patent: January 6, 1998Assignee: BASF AktiengesellschaftInventors: Tom Witzel, Guido Voit
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Patent number: 5686616Abstract: A novel process for preparing an optically active amine by asymmetric hydrogenation of an imine compound, such as an imine compound prepared by condensing benzylamine and acetophenone, in the presence of a catalytic amount of an iridium-optically active phosphine complex and benzylamine or a benzylamine derivative. The present invention provides an optically active amine of high optical purity.Type: GrantFiled: March 14, 1996Date of Patent: November 11, 1997Assignee: Takasago International CorporationInventors: Kazuhide Tani, Tsuneaki Yamagata, Yasutaka Kataoka, Hidenori Kumobayashi
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Patent number: 5679860Abstract: A process for producing 3-aminomethyl-3,5,5-trimethylcyclohexyl amine (isophorone diamine) from isophorone nitrile. Isophorone nitrile is iminated in a first stage and then the reaction mixture is subjected to aminating hydrogenation in a second stage in the presence of a fixed bed hydrogenation catalyst based on Raney cobalt. The fixed bed hydrogenation catalyst is produced in a special manner by mixing a powdery Co--containing Raney alloy with powdery cobalt, sintering the powdery mixture to shaped moldings and then activating by leaching with alkali hydroxide solution. The yield and/or space-time yield in isophorone diamine production can be increased.Type: GrantFiled: October 28, 1996Date of Patent: October 21, 1997Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Roland Burmeister, Dietrich Arntz, Karl-Ludwig Weber, Monika Berweiler
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Patent number: 5659075Abstract: A process is claimed for preparing [1S(1(.alpha., 2.beta., 4.beta.)]-4-amino-2-hydroxymethyl -1-cyclopentanol from cis-4-((R)-benzoylamino)-2-cyclopentenecarboxylic acid, methyl ester in five steps. The invention also describes a number of novel intermediates useful in the synthesis of [1S(1.alpha., 2.beta.,4.beta.)]-4-amino-2-hydroxymethyl-1-cyclopentanol.Type: GrantFiled: April 6, 1995Date of Patent: August 19, 1997Assignee: Glaxo Group LimitedInventors: Bernard Charles Halter, Clive Alwin Meerholz, Mark Brian Schilling, David Joszef Tapolczay, John Peter Turnbull
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Patent number: 5583260Abstract: A method of controlling the cis/trans isomer ratio in the preparation of isophoronediamine by the aminating hydrogenation of isophoronenitrile in the presence of ammonia, H.sub.2 and a catalyst. The reaction takes place in two temperature steps, initially at 10.degree. to 90.degree. C. and then at above 90.degree. to 150.degree. C. with a temperature difference of at least 30.degree. C. between the two steps, the contact time being shorter in the first step than in the second. The cis/trans ratio is increased by lowering the temperature of the first step.Type: GrantFiled: December 22, 1994Date of Patent: December 10, 1996Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Dietrich Arntz, Dieter Most
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Patent number: 5514716Abstract: This disclosure relates to a novel class of hydroxamic and carboxylic acid based matrix metalloproteinase inhibitor derivatives. The disclosure further relates to pharmaceutical compositions containing such compounds and to the use of such compounds and compositions in the treatment of matrix metalloproteinase induced diseases.Type: GrantFiled: February 25, 1994Date of Patent: May 7, 1996Assignee: Sterling Winthrop, Inc.Inventors: Madhusudhan R. Gowravaram, Jeffrey Johnson, Ewell R. Cook, Robert C. Wahl, Alan M. Mathiowetz, Bruce E. Tomczuk, Ashis K. Saha
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Patent number: 5514358Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.Type: GrantFiled: March 29, 1995Date of Patent: May 7, 1996Inventors: Charles J. Rogers, Alfred Kornel
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Patent number: 5504254Abstract: A process is disclosed for the continuous preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine) in high yield and high purity from 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile) by aminating hydrogenation with hydrogen and ammonia in the presence of a fixed bed catalyst. The aminating hydrogenation is carried out by allowing a mixture of isophoronenitrile, ammonia and a C.sub.1 -C.sub.3 -alcohol, in the presence of hydrogen, to trickle over a trickle bed reactor provided with a Co and/or Ru fixed bed catalyst, at 3 to 8 MPa and at a temperature of 40.degree. to 150.degree. C., preferably 90 to 130.degree. C., and working up the reaction mixture by distillation. Preferably, a high-boiling by-product fraction, containing a bicyclic amidine, is added to the mixture to be hydrogenated, thereby appreciably increasing the yield.Type: GrantFiled: December 22, 1994Date of Patent: April 2, 1996Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Dietrich Arntz, Dieter Most
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Patent number: 5491264Abstract: Isophorone diamine is prepared from isophorone nitrile by imination using a supported heteropoly acid catalyst to form the ketimine followed by the reduction of the ketimine to form the diamine.Type: GrantFiled: September 12, 1994Date of Patent: February 13, 1996Assignee: E. I. du Pont de Nemours and CompanyInventors: Frank E. Herkes, Kostantinos Kourtakis
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Patent number: 5410082Abstract: Process for preparing amines by reacting amides in aqueous-alkaline solutions and/or suspensions with halogens or hypohalites in the presence of alcohols, and converting the reaction products into the amines by hydrolysis, hydrogenation or reductive methods.Type: GrantFiled: May 9, 1994Date of Patent: April 25, 1995Inventor: Ralf Pfirmann
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Patent number: 5406000Abstract: A method is disclosed for the selective preparation of 3-aminomethyl-3,5,5-trialkylcyclohexylamine by preparing dried 3-cyano-3,5,5-trialkylcyclohexylimine from the reaction of 3-cyano-3,5,5-trialkylcyclohexanone with ammonia in the presence of a drying agent in an amount at least sufficient to retain the water present or generated during the imine-forming reaction, and hydrogenating the dried 3-cyano-3,5,5-trialkylcyclohexylimine in the presence of a cobalt-containing catalyst at elevated temperature and pressure.Type: GrantFiled: January 12, 1993Date of Patent: April 11, 1995Assignee: Elf/Atochem North America, Inc.Inventor: Christian Forquy
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Patent number: 5371292Abstract: A process for the preparation of 3-aminomethyl-3,5,5-trimethyl-cyclohexylamine from 3-cyano-3,5,5-trimethyl-cyclohexanone, wherein the following stages are carried out in discrete reaction chambers:a) the 3-cyano-3,5,5-trimethyl-cyclohexanone is reacted in a first reaction chamber with excess ammonia over an acidic metal oxide catalyst at a temperature of from 20.degree. to 150.degree. C. and a pressure of from 15 to 500 bar, andb) in a second reaction chamber, the reaction product from stage a) is hydrogenated with hydrogen at a temperature of from 60.degree. to 150.degree. C. and a pressure of from 50 to 300 bar in the presence of excess ammonia over a catalyst containing cobalt, nickel, ruthenium, and/or some other noble metal, which catalyst optionally contains a basic component or is supported by neutral or basic supporting material.Type: GrantFiled: July 15, 1993Date of Patent: December 6, 1994Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Wolfgang Harder
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Patent number: 5344983Abstract: Process for preparing a pentane-1,5-diamine of the formula ##STR1## where R.sup.1 represents a variety of organic radicals including alkyl which can bear substituents such as hydroxyl, halogen, alkoxy, carbalkoxy, carboxyl, alkylamino, cycloalkyl or aryl, andR.sup.2 and R.sup.3 independently of one another, represent hydrogen or have the same meanings as R.sup.1 or together are a C.sub.4 -C.sub.7 -alkylene chain which is unsubstituted or substituted by one to five C.sub.1 -C.sub.4 -alkyl groups,which comprises:(a) reacting a .gamma.-cyanoketone of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 have the meanings given above, with excess ammonia in a first reaction space on an acidic heterogeneous catalyst at 20.degree.-150.degree. C. and 15-500 bar, and(b) hydrogenating the resulting reaction product in a second separate reaction space in the presence of excess ammonia on a cobalt, nickel or noble metal catalyst at 50.degree.-180.degree. C. and 30-500 bar.Type: GrantFiled: August 26, 1992Date of Patent: September 6, 1994Assignee: BASF AktiengesellschaftInventors: Tom Witzel, Eberhard Fuchs, Franz Merger, Claus-Ulrich Priester
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Patent number: 5296632Abstract: Nitro polyamines, and especially dinitro polyamines, can be readily reduced by a catalyst of zerovalent nickel on silica where the silica contains not more than 10% alumina and where the nickel content of the finished catalyst may be as high as 85%. The reductions can be performed under relatively low temperatures between 40.degree. and 120.degree. C. to avoid the problem of heat lability of the reactant nitro polyamines. Hydrogenations proceed with good conversion as well as good selectivity and the method offers a means of continuous hydrogenation of nitro polyamines.Type: GrantFiled: July 2, 1992Date of Patent: March 22, 1994Assignee: UOPInventors: Dusan J. Engel, Thomas P. Malloy, Steven R. Paeschke
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Patent number: 5286906Abstract: A process for the preparation of a 3-aminomethyl-3,5,5-trialkylcyclohexylamine, which comprises hydrogenating 3-cyano-3,5,5-trialkylcyclohexylamine in the presence of ammonia and a ruthenium-cobalt catalyst.Type: GrantFiled: September 25, 1992Date of Patent: February 15, 1994Assignee: Mitsubishi Kasei CorporationInventors: Yoshinori Hara, Haruhiko Kusaka, Masamichi Onuki, Sugio Nishimura
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Patent number: 5283366Abstract: The reductive amination of 1,3,3-trimethyl-5-oxocyclohexane carbonitrile (IPN) with ammonia and hydrogen in the presence of nickel- or cobalt Raney catalysts to 3-aminomethyl-3, 5,5-trimethyl-cyclohexyl amine is achieved in a single stage with a good yield and requires no pressure distillation if a co-catalyst selected from the group consisting of salts of nickel, cobalt, yttrium, lanthanum and cerium is used in an amount of 0.01 to 0.5 mole per mole Raney catalyst.Type: GrantFiled: February 25, 1993Date of Patent: February 1, 1994Assignee: Degussa AGInventors: Klaus Huthmacher, Hermann Schmitt
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Patent number: 5266731Abstract: Described are processes for producing amines from nitriles. The processes include electrocatalytic hydrogenations of nitriles in the presence of transition metal-oxide and/or transition metal-hydroxide cathodes to thereby form amines. Preferred modes of the invention provide highly advantageous processes for producing hexamethylenediamine from adiponitrile.Type: GrantFiled: July 17, 1991Date of Patent: November 30, 1993Assignee: Reilly IndustriesInventors: William M. Ayers, Mary H. Dean
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Patent number: 5239120Abstract: A process for the preparation of a 2-(3-aminopropyl)-cycloalkylamine of the general formula I ##STR1## in which the subscript n is an integer from 1 to 4, from a 2-(2-cyanoethyl)-cycloalkanone of the general formula II ##STR2## in which the subscript n has the meaning stated, wherein the following stages are carried out in discrete reaction chambers:a) the 2-(2-cyanoethyl)-cycloalkanone of formula II is reacted in a first reaction chamber with excess ammonia over an acidic heterogeneous catalyst at a temperature from 20.degree. to 150.degree. C. and a pressure of from 15 to 500 bar, andb) in a second reaction chamber, the reaction product from stage a) is hydrogenated at a temperature of from 60.degree. to 150.degree. C. and a pressure of from 50 to 300 bar in the presence of excess ammonia over a catalyst containing cobalt, nickel, ruthenium, and/or some other noble metal, which catalyst optionally contains a basic component or is supported on neutral or basic supporting material.Type: GrantFiled: March 27, 1991Date of Patent: August 24, 1993Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Gerhard Koppenhoefer, Wolfgang Harder, Tom Witzel, Helmut Lermer, Ulrich Koehler
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Patent number: 5166435Abstract: The present invention relates to a process for the preparation of organic hydroxylamines as a result of the corresponding nitroderivative being hydrogenated in the presence of an inert solvent, a platinum catalyst, a nitrogen-containing base (in an amount of less than 10% by weight calculated on the amount of nitro derivative) and a tri- or pentavalent organic phosphorus compound. It has been found that if only use is made of the nitrogen-containing base or the phosphorus compound the yields of isolated hydroxyl amine are significantly reduced in comparison with those obtained with the present process.Type: GrantFiled: March 24, 1988Date of Patent: November 24, 1992Assignee: Akzo N.V.Inventors: Ashutosh H. Sharma, Peter Hope
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Patent number: 5099067Abstract: The present invention relates to a method of converting .beta.-nitro compounds, specifically alcohols, into the corresponding hydroxy amines with retention of configuration by the use of ammonium formate.Type: GrantFiled: August 15, 1991Date of Patent: March 24, 1992Assignee: Northwestern UniversityInventors: Anthony G. M. Barrett, Christopher D. Spilling
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Patent number: 5091567Abstract: The instant invention concerns a novel process for the preparation of 1-aminomethyl-1-cyclohexaneacetic acid (gabapentin), a known compound useful for treating certain cerebral diseases such as epilepsy and dizziness.Type: GrantFiled: August 21, 1990Date of Patent: February 25, 1992Assignee: Godecke AktiengesellschaftInventors: Wolfram Geibel, Johannes Hartenstein, Wolfgang Herrmann, Joachim Witzke
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Patent number: 5032687Abstract: The present process for the preparation of cyclopropylamine by the so-called Hofmann degradation of cyclopropanecarboxamide is characterized in that the cyclopropanecarboxamide is employed in the form of a solution. The new process can be carried out at 5.degree.-35.degree. C. The cyclopropylamine is obtained after introducing the reaction mixture into a concentrated alkali metal hydroxide solution.Type: GrantFiled: October 18, 1989Date of Patent: July 16, 1991Assignee: Kernforschunganlage Julich Gesellschaft mit beschrankter Haftung.Inventors: Herbert Diehl, Heinz U. Blank, Edwin Ritzer
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Patent number: 4937384Abstract: An amine is produced by reacting an amide with hydrogen at elevated temperature in the presence as catalyst of a composition comprising as a first component (i) a noble metal of Group VIII of the Periodic Table of the Elements, particularly palladium or ruthenium, and (ii) rhenium, which component may be supported, and as a second component either an alumina or a zeolite, preferably a low silica aluminosilicate zeolite, for example type A or type Y zeolite.Type: GrantFiled: March 16, 1988Date of Patent: June 26, 1990Assignee: BP Chemicals LimitedInventor: Ian D. Dobson
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Patent number: 4739120Abstract: An improved process is disclosed for the catalytic hydrogenation of an organic nitrile group containing compound to a primary aminomethyl group in the presence of a rhodium catalyst, a basic substance, and in a two-phase solvent system comprising an immiscible organic solvent and water.Type: GrantFiled: August 21, 1986Date of Patent: April 19, 1988Assignee: The Dow Chemical CompanyInventor: Marie F. Zuckerman
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Patent number: 4705898Abstract: A two-step process for the preparation of secondary amines in good yield from olefins, carbon monoxide, hydrogen and primary amines is described. The intermediate imine may be isolated in good yield as well.Type: GrantFiled: April 4, 1986Date of Patent: November 10, 1987Assignee: Texaco Inc.Inventors: Edward E. McEntire, John F. Knifton
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Patent number: 4698446Abstract: A nitroamine is formed from an aliphatic amine reactant + a nitroalkane + an aldehyde with better conversion, and faster, if the aldehyde is added last, and gradually, so as not to form an alkanolamine intermediate with the aldehyde as in the prior art reactions. In particular, a diamine such as ethylene diamine (EDA) has the unique ability, even among diprimary amines, to react with nitroalkane, to form a salt intermediate to which is added an essentially solvent-free aldehyde such as paraformaldehyde to produce a reaction product consisting essentially of a mixture of (i) a mononitrodialkylenediamine with a disubstituted N-adjacent terminal C atom and (ii) a dinitrotrialkylenediamine with each N-adjacent terminal C atom being disubstituted; and the mixture is obtained in an yield of at least 90 mol %.Type: GrantFiled: July 1, 1986Date of Patent: October 6, 1987Assignee: The BF Goodrich CompanyInventors: John T. Lai, Pyong N. Son