Of Plural Cyanos Patents (Class 564/491)
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Patent number: 7399886Abstract: This invention relates to an improved hydrogenation process for the preparation of etheramines. In the process, cyanoethylated alcohols, i.e., the reaction product of an alcohol with (meth)acrylonitrile, are contacted with hydrogen in the presence of a sponge cobalt catalyst. The improvement in the process resides in effecting the hydrogenation process utilizing a cyanoethylated alcohol feedstock contaminated with byproduct acrylonitrile and utilizing a solvent that solubilizes byproduct (meth)acrylonitrile present in the feedstock. Specific classes of solvents employed are ethers and amides.Type: GrantFiled: September 4, 2003Date of Patent: July 15, 2008Inventors: Garnini Ananda Vedage, Eugene George Lutz, Matthew J. Engel
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Patent number: 7381845Abstract: A process for hydrogenating nitrile functions present in organic compounds over at least one heterogeneous catalyst, in which the hydrogenation is carried out in the presence of an ionic liquid, is described.Type: GrantFiled: December 20, 2004Date of Patent: June 3, 2008Assignee: BASF AktiengesellschaftInventors: Verena Weiskopf, Till Gerlach, Kirsten Wenz
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Patent number: 7291754Abstract: Process for the catalytic hydrogenation of a nitrite in the presence of an amine and a catalyst wherein the catalyst is a liquid-rinsed Raney-type catalyst contacted with a hydroxide prior to contacting the catalyst with the amine. The process results in higher selectivity in the formation of diamines from diniriles.Type: GrantFiled: January 21, 2004Date of Patent: November 6, 2007Assignee: DSM IP Assets B.V.Inventors: Franciscus H. A. M. Vandenbooren, Hubertus J. M. Bosman, Alexander V. Peters, Maria J. G. Van Den Boer
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Patent number: 7208448Abstract: The invention relates to a passivated hydrogenation catalyst that is embedded in a primary amine, a derivative thereof, and/or a nitrile, the process to make such catalysts, as well as the use of such catalysts in a hydrogenation process in which an amine or a derivative thereof is produced.Type: GrantFiled: March 13, 2003Date of Patent: April 24, 2007Assignee: Akzo Nobel N.V.Inventors: Thale Jacob Ottens, Jacobus Van Den Berg, Paul Van Poecke
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Patent number: 7196223Abstract: A nitrile-containing mixture, which includes a nitrile dissolved in a higher alcohol solvent, and hydrogen are fed to a reactor containing a catalyst. An amine is produced by hydrogenating the nitrile that is dissolved in the higher alcohol solvent. In a preferred embodiment, the reactor also contains a caustic solution. The preferred nitrile-containing mixture includes octadecaneditrile (ODDN) and hexanol to produce a preferred octadecanediamine (ODDA) through hydrogenation.Type: GrantFiled: May 3, 2005Date of Patent: March 27, 2007Assignee: Solutia, Inc.Inventors: Tom L. Flowers, Anthony K. Uriarte, Shannon Davis, Gregory J. Ward
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Patent number: 7115781Abstract: An oxidic composition which is suitable as a catalyst having divalent and trivalent iron in an atomic ratio of divalent to trivalent iron in the range from greater than 0.5 to 5.5 and oxygen as a counterion to the divalent and trivalent iron. The catalyst composition is useful in the hydrogenation of nitriles to amines.Type: GrantFiled: October 18, 2002Date of Patent: October 3, 2006Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch, Peter Bassler, Rolf-Hartmuth Fischer, Stefan Maixner, Johann-Peter Melder, Hermann Luyken
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Patent number: 6984759Abstract: Process for the perfluoropolyether preparation having reactive end groups —CH2NH2, —CHO, —CH2OH, by reduction of the corresponding perfluoropolyethers having —CN, —COCl, —CHO end groups by using gaseous hydrogen in the presence of a catalyst constituted by Pd, Rh, or Ru, supported on solid metal fluorides, at a temperature from 20° C. to 150° C. and under a pressure between 1 and 50 atm.Type: GrantFiled: July 31, 2003Date of Patent: January 10, 2006Assignee: Solvay Solexis S.p.A.Inventors: Antonella Di Meo, Rosaldo Picozzi, Claudio Tonelli
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Publication number: 20040181095Abstract: A material useful as catalyst for the hydrogenation of alpha, omega-dinitriles comprisesType: ApplicationFiled: February 12, 2004Publication date: September 16, 2004Inventors: Guido Voit, Rolf Fischer, Peter Babetaler, Andreas Ansmann, Hermann Luyken, Martin Merger, Frank Ohlbach, Alwin Rehfinger
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Patent number: 6790994Abstract: The present invention relates to a process for the hydrogenation of nitrile functional groups to amine functional groups. It relates more particularly to a process for the complete or partial hydrogenation of dinitrile compounds to diamine or aminonitrile compounds. The invention relates to a process for the hydrogenation of nitrile functional groups to amine functional groups using hydrogen in the presence of a hydrogenation catalyst and of a strong inorganic base preferably deriving from an alkali metal or alkaline earth metal. According to the invention, the process comprises a stage of conditioning the catalyst which consists in mixing the hydrogenation catalyst, a predetermined amount of strong inorganic base and a solvent in which the strong inorganic base is not very soluble. This solvent is an amine compound, such as hexamethylenediamine in the case of the hydrogenation of adiponitrile to HMD and/or aminocapronitrile.Type: GrantFiled: January 10, 2003Date of Patent: September 14, 2004Assignee: Rhodia Polyamide IntermediatesInventors: Vincent Boschat, Philippe Leconte
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Patent number: 6790996Abstract: The invention relates to a process for preparing primary amines by hydrogenating nitrites in the presence of a catalyst comprising cobalt and optionally, in addition, nickel and also at least one further doping metal on a particulate support material, the cobalt and, if present, the nickel having an average particle size of from 3 to 30 nm in the active catalyst. The invention further relates to the use of the catalyst in a process for preparing primary amines by hydrogenating nitrites.Type: GrantFiled: October 17, 2002Date of Patent: September 14, 2004Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch
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Patent number: 6677486Abstract: Nitriles are hydrogenated to primary amines over an activated, alpha-Al2O3-containing, macroporous Raney catalyst based on an alloy of aluminum and at least one transition metal selected from the group consisting of iron, cobalt and nickel, and, if desired, one or more further transition metals selected from the group consisting of titanium, zirconium, chromium and manganese, which is obtainable by a process comprising the steps in the order (a)-(f): (a) preparing a kneadable composition comprising the alloy, a shaping aid, water and a pore former; (b) shaping the kneadable composition to form a shaped body; (c) calcining the shaped body; (d) activating the calcined shaped body by treatment with aqueous alkali metal hydroxide solution; (e) rinsing the shaped catalyst body with aqueous alkali metal hydroxide solution; (f) rinsing the shaped catalyst body with water.Type: GrantFiled: November 7, 2001Date of Patent: January 13, 2004Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
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Patent number: 6600075Abstract: Disclosed is a method for preparing tertiary amine compounds from primary amines and nitrites in the presence of hydrogen gas and a metal catalyst, or metal-containing catalyst composition, at a temperature from about 50° C. to about 200° C. and at a pressure from about 100 psig to 1500 psig. The primary amines and the nitriles used in the process may be diamines and/or dinitriles, or may be combinations of primary amines and/or nitrites. Also disclosed are novel tertiary amine compounds made by the described method.Type: GrantFiled: November 13, 2001Date of Patent: July 29, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Kelley Moran Whittle, Alan Martin Allgeier, Thomas Papin Gannett, David Page Higley
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Patent number: 6469211Abstract: In a process for the continuous hydrogenation of nitrites to primary amines in the liquid phase over a suspended, activated Raney catalyst based on an alloy of aluminum and at least one transition metal selected from the group consisting of iron, cobalt and nickel, and, if desired, one or more further transition metals selected from the group consisting of titanium, zirconium, chromium and manganese, the hydrogenation is carried out in the absence of ammonia and basic alkali metal compounds or alkaline earth metal compounds.Type: GrantFiled: November 14, 2001Date of Patent: October 22, 2002Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
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Patent number: 6399830Abstract: This invention pertains to an improvement in a process for the formation of secondary or tertiary amines by the catalytic reductive amination of a nitrile with a primary amine. The catalyst employed in the improved reductive amination process is one that has been promoted with an acidic promoter preferably a solid phase acidic promoter.Type: GrantFiled: December 13, 2000Date of Patent: June 4, 2002Assignee: Air Products and Chemicals, Inc.Inventors: John Nelson Armor, Michael Edward Ford, William Eamon Carroll
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Patent number: 6380420Abstract: A process for preparing fatty amines by the cross-metathesis of normal alpha olefins and acrylonitrile to form an intermediate fatty acid nitrile which is hydrogenated to the corresponding fatty amine.Type: GrantFiled: September 8, 2000Date of Patent: April 30, 2002Assignee: Chevron U.S.A. Inc.Inventors: William L. Schinski, Michael S. Driver
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Patent number: 6376714Abstract: Process for converting a dinitrile to a diamine and optionally an aminonitrile, in which a Group VIII element catalyst is treated with a modifier either before or during a substantially solvent-free hydrogenation reaction in which the dinitrile is contacted with hydrogen in the presence of the catalyst.Type: GrantFiled: May 31, 2001Date of Patent: April 23, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Alan M. Allgeier, Theodore A. Koch, Sourav K. Sengupta
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Publication number: 20010005764Abstract: The present invention relates to a process for the preparation of 2-aminomethyl-1,5-pentanediamine by simultaneously reacting 2,4-dicyano-1-butene, hydrogen and ammonia in one step without isolation of 2-amino-methyl-1,5-pentanedinitrile; the products are useful as an intermediate in the production of coating compositions, surfactants, detergents and as a component of epoxide compositions.Type: ApplicationFiled: February 1, 2000Publication date: June 28, 2001Inventors: Konrad Fischer, Frank Richter, Anatoly Bazanov, Alexandre Timofeev, Natalja Zubritskaya, Galina Smirnova
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Patent number: 6198002Abstract: A process for preparing a secondary or tertiary 2-methyl-1,5-pen-tanediamine of the formula I where R1 and R2 are H, C1-C20-alkyl, C3-C8-cycloalkyl, aryl, C7-C20-arylalkyl, where the radicals R1 and R2 may bear substituents selected from the group consisting of C1-C20-alkyl, C1-C20-alkoxy, C6-C20-aryloxy and hydroxy, and R1 and R2 are not simultaneously hydrogen, or R1 and R2 are together an unsubstituted or C1-C20-alkyl- and/or C1-C20-alkoxy-substituted C3-C7-alkylene chain which may, if desired, be interrupted by one or two O or NR3 groups, where R3 is H or C1-C20-alkyl comprises reacting 2-methylglutarodinitrile with a primary or secondary amine of the formula R1R2NH and hydrogen at from 50 to 250° C. and pressures of from 0.5 to 35 MPa in the presence of an oxidic supported catalyst comprising one or more noble metals which has been treated with hydrogen at from 50 to 300° C. for at least 0.5 hour before use.Type: GrantFiled: June 3, 1999Date of Patent: March 6, 2001Assignee: BASF AktiengesellschaftInventors: Karsten Eller, Bernd Fiege, Stefan Rittinger, Eberhard Fuchs
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Patent number: 6156694Abstract: The present invention relates to a Raney catalyst comprising iron, cobalt, a third metal wherein the third metal is selected from the group consisting of nickel, rhodium, ruthenium, palladium, platinum, osmium, iridium and mixtures of any of the metals of this group.Type: GrantFiled: November 5, 1998Date of Patent: December 5, 2000Assignee: E. I. Dupont De Nemours & CompanyInventor: Mark Jay Harper
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Patent number: 6153784Abstract: Halides are removed from halide-containing nitrile mixtures by(a) thermally treating the halide-containing nitrile mixture,(b) subsequently adding a base to the thermally treated nitrile mixture and(c) subsequently separating off the base from the nitrile mixture.Amines are prepared by(A) reacting alkyl halides with metal cyanides in an at least two-phase reaction medium in the presence of halide-containing phase-transfer catalysts to give alkanenitriles,(B) separating off the resulting halide-containing alkanenitrile mixture phase and(C) further treating the halide-containing alkanenitrile mixture phase, as described in the stages(a)-(c) removing halides from halide-containing nitrile mixtures and(d) hydrogenating nitrites obtained in stage (c) to give amines, in the presence of suspended or fixed-bed catalysts.Type: GrantFiled: February 17, 1998Date of Patent: November 28, 2000Assignee: BASF AktiengesellschaftInventors: Heinz-Josef Kneuper, Hans-Jurgen Weyer, Horst Neuhauser, Johann-Peter Melder, Andreas Henne, Karl-Heinz Ross, Rainer Becker
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Patent number: 6087296Abstract: The present invention relates to a Raney catalyst comprising iron, cobalt, a third metal wherein the third metal is selected from the group consisting of nickel, rhodium, ruthenium, palladium, platinum, osmium, iridium and mixtures of any of these metals.Type: GrantFiled: November 5, 1998Date of Patent: July 11, 2000Assignee: E. I. du Pont de Nemours & Co.Inventor: Mark Jay Harper
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Patent number: 6005145Abstract: The present invention relates to new metal compounds, to a process for the preparation of these metal compounds and to their use as catalysts.The new metal compounds according to the invention have, when they are used as catalysts, in particular as hydrogenation catalysts, an efficiency of the same order as that obtained with Raney nickel or cobalt.These metal compounds are more precisely compounds containing one or a number of divalent metals at least partially in the reduced state, bulked by a phase comprising one or a number of doping metals chosen from chromium, molybdenum, iron, manganese, titanium, vanadium, gallium, indium, bismuth, yttrium, cerium, lanthanum and the other trivalent lanthanides, in the form of oxides.Type: GrantFiled: August 3, 1998Date of Patent: December 21, 1999Assignee: Rhone-Poulenc Fiber and Resin IntermediatesInventors: Georges Cordier, Jean-Michel Popa
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Patent number: 5894074Abstract: A process for preparing amines of the general formula (I)X(--CH.sub.2 --NR.sup.1 R.sup.2).sub.n (I)whereR.sup.1 and R.sup.2 are preferably methyl, X is preferably 1,4-butylene and n is preferably 2, comprises reacting nitriles of the general formula (II)(R.sup.1 R.sup.2 N--CH.sub.2 --).sub.n-m X(--CN).sub.m (II)where R.sup.1, R.sup.2 and X are each as defined above and m is an integer from 1 to n,with secondary amines of the general formula (III)HNR.sup.1 R.sup.2 (III)where R.sup.1 and R.sup.2 are each as defined above,and hydrogen at from 50 to 250.degree. C. and from 5 to 350 bar in the presence of a palladium catalyst comprising, based on the total weight of the catalyst, from 0.1 to 10% by weight of Pd and from 0.01 to 10% by weight of at least one further metal selected from groups IB and VII of the Periodic Table, cerium and lanthanum on a support.Type: GrantFiled: March 31, 1998Date of Patent: April 13, 1999Assignee: BASF AktiengesellschaftInventors: Eberhard Fuchs, Boris Breitscheidel, Rainer Becker, Horst Neuhauser
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Patent number: 5886227Abstract: Disclosed is an improved process for the catalytic hydrogenation of cyanopropionaldehyde alkyl acetals (CPAA) to form the aminobutyraldehyde alkyl acetals. The basic process comprises hydrogenating the cyanopropionaldehyde alkyl acetals by contacting said cyanopropionaldehyde alkyl acetals with hydrogen in the presence of a nickel or cobalt catalyst under conditions for reducing the nitrile group to the primary amine. The improvement resides in effecting the hydrogenation of a cyanopropionitrile dialkyl acetal feedstock containing contaminating levels of cyanopropionaldehyde in the presence of a secondary alkanol or water.Type: GrantFiled: October 28, 1997Date of Patent: March 23, 1999Assignee: Air Products and Chemicals, Inc.Inventors: Gamini Ananda Vedage, Kathryn Sue Hayes
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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: 5869653Abstract: An improved process for the catalytic hydrogenation of nitriles. The basic process comprises contacting the nitrile with hydrogen in the presence of a sponge or Raney cobalt catalyst under conditions for effecting conversion of the nitrile group to the primary amine. The improvement in the hydrogenation process resides in effecting the hydrogenation in the presence of a catalytic amount of lithium hydroxide and water. To achieve a catalytic amount of lithium hydroxide, the catalyst may be pretreated with the lithium hydroxide and/or the reaction may be carried out with the lithium hydroxide present in the reaction medium.Type: GrantFiled: October 30, 1997Date of Patent: February 9, 1999Assignee: Air Products and Chemicals, Inc.Inventor: Thomas Albert Johnson
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Patent number: 5844114Abstract: The invention relates to a method for the selective hydrogenation of a dinitrile compound in the presence of a catalyst which comprises a metal of group 8 of the periodic system of the elements, the catalyst comprising a zeolite having a pore diameter of between 0.3 and 0.7 nm. The zeolite preferably has a structure chosen from the structures: ABW, AEI, AFT, ANA, ATN, ATV, ATT, AWW, BIK, CAS, CHA, DDR, EAB, EDI, ERI, GIS, JBW, KFI, LEV, LTA, MER, NAT, PHI, RHO, THO, YUG.Type: GrantFiled: November 14, 1995Date of Patent: December 1, 1998Assignee: DSM N.V.Inventors: Franciscus H.A.M.J. Vandenbooren, Hubertus J.M. Bosman, Jan Van Der Spoel
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Patent number: 5840989Abstract: The invention relates to a method of doping a Raney nickel catalyst doped with metals by the incorporation of the doping metals in the form of a complex into the alkaline attack medium. Also disclosed is a process for the hydrogenation of nitriles to amines using said catalyst.Type: GrantFiled: September 24, 1996Date of Patent: November 24, 1998Assignee: Rhone-Poulenc ChimieInventors: Georges Cordier, Pierre Fouilloux, Nathalie Laurain
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Patent number: 5801286Abstract: The present invention relates to the field of the catalytic hydrogenation of nitrites to amines and, more particularly, of dinitriles such as adiponitrile (ADN) to diamines such as hexamethylenediamine (HMD).More precisely, the present invention relates to a process for the preparation of a catalyst for the hydrogenation of nitriles to amines of Raney nickel type doped with at least one additional metal element selected from columns IVb, Vb and VIb of the periodic classification.It is targeted at providing an economic and easy-to-implement process which makes it possible to obtain catalysts which are both active and selective with respect to nitrites and stable.The process is characterized in that it consists in suspending Raney nickel in a solution, preferably an acid solution, of the additional metal element.Type: GrantFiled: September 23, 1996Date of Patent: September 1, 1998Assignee: Rhone-Poulenc ChimieInventors: Michele Besson, Georges Cordier, Pierre Fouilloux, Jacqueline Masson
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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: 5777166Abstract: The present invention relates to the field of the catalytic reduction of nitriles to amines by use of Raney catalysts doped with one or a number of additional metal elements chosen from the elements of group IVb of the periodic classification.More precisely, it relates to a process for the hydrogenation of nitriles to amines, characterized in that it essentially consists:in selecting a liquid reaction medium which dissolves the nitrile substrate to be hydrogenated,in using at least one inorganic alkali metal or alkaline-earth metal hydroxide base,and in adopting a catalyst whose doping element/Ni ratio by weight is between 0.05 and 10%.More specific application to the hydrogenation of dinitriles to diamines or to aminonitriles.Type: GrantFiled: November 25, 1996Date of Patent: July 7, 1998Assignee: Rhone-Poulenc ChimieInventors: Georges Cordier, Pierre Fouilloux, Nathalie Laurain, Jean-Francis Spindler
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Patent number: 5763669Abstract: This invention relates to a process of preparing a ruthenium complex of the formula RuH.sub.2 (PR.sub.3).sub.2 L.sub.2 wherein PR.sub.3 is an organophosphorus ligand and L is H.sub.2 or PR.sub.3 ; a catalyst comprising at least one ruthenium complex having the formula RuH.sub.2 (PR.sub.3)L.sup.1.sub.3 wherein L.sup.1 is a neutral electron pair donor ligand; a process for preparing the catalyst and its use in situ in the hydrogenation of nitriles.Type: GrantFiled: June 21, 1996Date of Patent: June 9, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Richard Paul Beatty, Rocco Angelo Paciello
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Patent number: 5760157Abstract: Compounds of the formula?P!(ACH.sub.2 NH.sub.2).sub.xin which P denotes a partially hydrogenated 1,3-diene oligomer residue, x is practically equal to 2 and A denotes a divalent residue such as ##STR1## are obtained by selective hydrogenation of compounds of formula ?P.sub.1 !(ACN)x in which P.sub.1 denotes a 1,3-diene oligomer residue.Type: GrantFiled: December 20, 1996Date of Patent: June 2, 1998Assignee: Elf Atochem, S.A.Inventors: Martine Cerf, Stephane Fouquay, Joel Perthuis
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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: 5726334Abstract: This invention relates to a process for the preparation of ruthenium complexes of the formula RuH.sub.2 L.sub.2 (PR.sub.3).sub.2, wherein each L is independently H.sub.2 or an additional equivalent of PR.sub.3, and each R is independently H, a hydrocarbyl group, or an assembly of at least two hydrocarbyl groups connected by ether or amine linkages, comprising contacting a source of ruthenium and PR.sub.3 with gaseous hydrogen in the presence of a strong base, a phase-transfer catalyst, water and an organic solvent; and the use of certain classes of ruthenium complexes as catalysts in hydrogenation, and reductive hydrolysis processes.Type: GrantFiled: September 19, 1996Date of Patent: March 10, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Richard Paul Beatty, Rocco Angelo Paciello
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Patent number: 5689003Abstract: The invention relates to a novel ruthenium complex having the formula Ru(.eta..sup.3 --C.sub.6 H.sub.8 --PCy.sub.2)(PCy.sub.3)Cl, wherein Cy is cyclohexyl; its use in the preparation of RuHCl(H.sub.2)(PCy.sub.3).sub.2 and RuH.sub.2 (H.sub.2).sub.2 (PCy.sub.3).sub.2 ; and the use of the complexes as catalysts in hydrogenation, imination and reductive hydrolysis processes.Type: GrantFiled: May 8, 1996Date of Patent: November 18, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard Paul Beatty, Rocco Angelo Paciello
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Patent number: 5629451Abstract: A process for selectively reducing nitrile contaminants in fluids such as water, methanol or hydrocarbon streams containing mono olefins and which contain minor amounts of contaminants comprising nitriles in the presence of hydrogen and a supported cobalt catalyst. In the olefin stream the nitrile contaminants are substantially reduced without substantial reduction of the mono olefins.Type: GrantFiled: June 30, 1994Date of Patent: May 13, 1997Assignee: Chemical Research & Licensing CompanyInventors: Dennis Hearn, Kyte H. Terhune
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Patent number: 5597940Abstract: Disclosed is a process for producing .beta.-nitroenamine represented by the formula I: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and independently indicate a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group which may be optionally substituted with at least one group selected from the group consisting of a halogen atom, a lower alkoxy group, an aryloxy group, a hydroxyl group or an aryl group, or an aryl group which may be optionally substituted with a halogen atom, a lower alkyl group, a lower alkoxy group, an aryl group, an aryloxy group, a nitro group, a cyano group, an acylamino group, a di-lower alkylamino group, an arylamino group, a hydroxyl group, an arylsulfonyl group, a mercapto group, a lower alkylthio group or an arylthio group, R.sub.1 and R.sub.2 may bond together to form a cycloalkyl or bicycloalkyl and R.sub.3 is a hydrogen atom, a lower alkyl group, a cycloalkyl group or an aralkyl group; and an intermediate for producing the .beta.-nitroenamine.Type: GrantFiled: March 9, 1995Date of Patent: January 28, 1997Assignee: Sumitomo Chemical Company, LimitedInventor: Shinzo Seko
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Patent number: 5571943Abstract: This invention relates to a process for preparing primary amines by hydrogenation of mono and/or dinitrile with hydrogen in the presence of a nickel and/or cobalt catalyst on support and optionally in the presence of ammonia, this process being characterized in that a nickel and/or cobalt catalyst on support is used, optionally in combination with at least one solid, reaction medium-insoluble cocatalyst, the catalyst and/or the cocatalyst being substantially nonacid.Type: GrantFiled: March 28, 1995Date of Patent: November 5, 1996Assignee: Engelhard De Meern B.V.Inventors: Frederik Borninkhof, John W. Geus, Michiel J. F. M. Verhaak
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Patent number: 5557011Abstract: Process for the preparation of diamines of the general formula I ##STR1## in which A denotes a C.sub.1 -C.sub.20 alkylene chain optionally mono- to penta-substituted by C.sub.1 -C.sub.4 alkyl,R.sup.1, R.sup.2 denote C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 hydroxyalkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.20 alkylcycloalkyl, C.sub.4 -C.sub.20 cycloalkylalkyl, phenyl, C.sub.7 -C.sub.20 phenylalkyl, C.sub.1 -C.sub.20 alkoxyalkyl, C.sub.7 -C.sub.20 phenoxyalkyl or together a saturated or unsaturated C.sub.2 -C.sub.6 alkylene chain optionally monosubstituted, disubstituted, or trisubstituted by C.sub.1 -C.sub.4 alkyl and optionally interrupted by oxygen or nitrogen,by the reaction of dinitriles of the general formula IINC--A--CN (II),in which A has the aforementioned meaning,with secondary amines of the general formula II ##STR2## in which R.sup.1 and R.sup.2 have the aforementioned meanings, with hydrogen at temperatures ranging from 50.degree. to 200.degree. C.Type: GrantFiled: November 15, 1994Date of Patent: September 17, 1996Assignee: BASF AktiengesellschaftInventors: Tom Witzel, Eberhard Fuchs
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Patent number: 5554794Abstract: The invention includes a compound of formula I ##STR1## where R' is hydrogen, an alkyl, or aryl group; R"O is derived from R"OH which is a polyether mono-ol or hydrocarbyl mono-ol; and R"' independently is a hydrogen, an alkyl group or a substituted alkyl group. The invention also includes an unleaded fuel composition containing a compound of formula I and a process for making the compound of formula I.Type: GrantFiled: August 18, 1994Date of Patent: September 10, 1996Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 5296633Abstract: The methylated tertiary amines are selectively prepared by reacting a primary or secondary amine, or a nitrile or aminonitrile, including an aminoalcohol, etheramine, a polyamine or fatty polyamine or amidoamine, or amidopolyamine or dinitrile, with hexamethylenetetramine ("HMTA"), under hydrogen pressure at a temperature no greater than about 160.degree. C. and in the presence of a catalytically effective amount of a hydrogenation catalyst, e.g., nickel deposited onto appropriate support substrate therefor.Type: GrantFiled: December 30, 1992Date of Patent: March 22, 1994Inventor: Stephane Fouquay
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Patent number: 5268509Abstract: This invention relates to a process for the preparation of an iron catalyst used for the hydrogenation of organic compounds comprising partially oxidizing iron or an iron alloy in particulate form at an elevated temperature in the presence of gaseous oxygen until a weight gain of from 5% to 32% is obtained; and then reducing the partially oxidized iron or iron alloy at an elevated temperature in a stream of hydrogen.The invention also relates to a process for the preparation of primary amines comprising catalytically hydrogenating nitriles corresponding to said primary amines in the presence of an iron catalyst of the invention.Type: GrantFiled: June 11, 1990Date of Patent: December 7, 1993Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Dietrich Liebsch, Hans-H. Schwarz, Stephan Wendel, Peter Fischer
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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: 5254737Abstract: A method for producing secondary amines, particularly fatty secondary amines such as ditallowamine from fatty nitriles, such as tallow nitrile over a reduction, hydrogenation catalyst, such as nickel or cobalt, in two steps has been discovered. The reaction gives high selectivity of secondary amine over the coproduced primary and tertiary amines. The first step of the reaction is conducted continuously in the presence of ammonia and hydrogen. The secondary amine proportion is increased by a second stage using the same catalyst as the first stage, but in the absence of ammonia.Type: GrantFiled: September 17, 1990Date of Patent: October 19, 1993Assignee: Texaco Chemical CompanyInventor: Robert L. Zimmerman
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Patent number: 5254738Abstract: A process for the preparation of a 1,4-alkylenediamine of the general formula I ##STR1## in which the substituents R.sup.1 and R.sup.2 are independently hydrogen, C.sub.1 -C.sub.10 -alkyl, phenyl or benzyl, by reacting a succinic dinitrile of the general formula II ##STR2## in which R.sup.1 and R.sup.2 have the meanings stated, with hydrogen at a temperature of from 30.degree. to 250.degree. C. and a pressure of from 50 to 350 bar in contact with a hydrogenation catalyst, wherein the hydrogenation catalyst used contains cobalt oxide and one or more oxides of the elements iron, nickel, manganese, chromium, molybdenum, tungsten, and phosphorus and one or more oxides of elements in the alkali metal group, alkaline earth metal group, and rare earth group of the Periodic Table, and of scandium, and/or of yttrium.Type: GrantFiled: February 19, 1991Date of Patent: October 19, 1993Assignee: BASF AktiengesellschaftInventors: Ulrich Koehler, Hardo Siegel, Matthias Irgang
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Patent number: 5235108Abstract: This invention relates to a process for preparing secondary alkylamine by selective hydrogenation of alkylnitrile using a nickel-containing catalyst which contains copper as promoter, said catalyst having a selectivity, as herein defined, of not more than 8.Type: GrantFiled: February 18, 1992Date of Patent: August 10, 1993Assignee: Engelhard De Meern B.VInventors: Frederik Borninkhof, Eugene G. M. Kuijpers, Pieter H. Berben
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Patent number: 5196589Abstract: The present invention relates to novel methods of stabilizing polymers of acrylonitrile. The polymers are stabilized by the inclusion of small amounts of stable free radicals compounds which act to inhibit the homopolymerization of the acrylonitrile while promoting the reaction of the acrylonitrile with nucleophilic species such as amines and alcohols.Type: GrantFiled: September 16, 1991Date of Patent: March 23, 1993Assignee: LCE PartnershipInventors: Anthony J. O'Lenick, Jr., J. Michael Clumpner
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Patent number: 5166444Abstract: The invention relates to bis(3-cyano-3,5,5-trimethylcyclohexylidene)-azine (=IPN-azine), a method of its preparation by reacting 1,3,3-trimethyl-5-oxocyclohexane carbonitrile (=IPN) with a source for hydrazine in a molar ratio of essentially 2 to 1 in the presence of a solvent and to a method for the further processing of the IPN-azine to 3-(aminomethyl)-3,5,5-trimethylcyclohexyl amine (isophorone diamine=IPDA) by means of a hydrogenating azine splitting with hydrogen in the presence of an organic solvent, ammonia and of a catalytic system from the series (a) of a cobalt- or nickel-containing Raney catalyst and of a cocatalyst from the series of salts of the elements aluminum, cobalt, nickel, yttrium, lanthanum, cerium, Ru, Rh, Pd, Ir and Pt or of carrier-supported noble metals from the series Ru, Rh, Pd, Ir, Pt or b) of a carrier-supported Ru-, Pd- or Pt catalyst at a pressure of 3 to 30 MPa and a temperature of 50.degree. to 150.degree. C.Type: GrantFiled: March 9, 1992Date of Patent: November 24, 1992Assignee: Degussa AGInventors: Klaus Hutchmacher, Hermann Schmitt
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Patent number: 5132427Abstract: A process for the preparation of amines of the formula ##STR1## in which R.sup.1 is the radical H.sub.2 N-CH.sub.2 and R.sup.2 is hydrogen, or R.sup.1 and R.sup.2 together form a bridging group --CH.sub.2 --, by reacting 1,3,6-tricyanohexane at elevated temperature and pressure with hydrogen in contact with a catalyst containing, in addition to cobalt oxide, and oxide of an alkali metal, an oxide of an alkaline earth metal, an oxide of a rare earth or an oxide of scandium or yttrium.Type: GrantFiled: October 22, 1990Date of Patent: July 21, 1992Assignee: BASF AktiengesellschaftInventors: Ulrich Koehler, Hardo Siegel, Peter Jaeger, Matthias Irgang