Of Plural Cyanos Patents (Class 564/491)
  • Patent number: 7399886
    Abstract: 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: Grant
    Filed: September 4, 2003
    Date of Patent: July 15, 2008
    Inventors: Garnini Ananda Vedage, Eugene George Lutz, Matthew J. Engel
  • Patent number: 7381845
    Abstract: 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: Grant
    Filed: December 20, 2004
    Date of Patent: June 3, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Verena Weiskopf, Till Gerlach, Kirsten Wenz
  • Patent number: 7291754
    Abstract: 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: Grant
    Filed: January 21, 2004
    Date of Patent: November 6, 2007
    Assignee: DSM IP Assets B.V.
    Inventors: Franciscus H. A. M. Vandenbooren, Hubertus J. M. Bosman, Alexander V. Peters, Maria J. G. Van Den Boer
  • Patent number: 7208448
    Abstract: 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: Grant
    Filed: March 13, 2003
    Date of Patent: April 24, 2007
    Assignee: Akzo Nobel N.V.
    Inventors: Thale Jacob Ottens, Jacobus Van Den Berg, Paul Van Poecke
  • Patent number: 7196223
    Abstract: 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: Grant
    Filed: May 3, 2005
    Date of Patent: March 27, 2007
    Assignee: Solutia, Inc.
    Inventors: Tom L. Flowers, Anthony K. Uriarte, Shannon Davis, Gregory J. Ward
  • Patent number: 7115781
    Abstract: 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: Grant
    Filed: October 18, 2002
    Date of Patent: October 3, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Ansmann, Christoph Benisch, Peter Bassler, Rolf-Hartmuth Fischer, Stefan Maixner, Johann-Peter Melder, Hermann Luyken
  • Patent number: 6984759
    Abstract: 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: Grant
    Filed: July 31, 2003
    Date of Patent: January 10, 2006
    Assignee: Solvay Solexis S.p.A.
    Inventors: Antonella Di Meo, Rosaldo Picozzi, Claudio Tonelli
  • Publication number: 20040181095
    Abstract: A material useful as catalyst for the hydrogenation of alpha, omega-dinitriles comprises
    Type: Application
    Filed: February 12, 2004
    Publication date: September 16, 2004
    Inventors: Guido Voit, Rolf Fischer, Peter Babetaler, Andreas Ansmann, Hermann Luyken, Martin Merger, Frank Ohlbach, Alwin Rehfinger
  • Patent number: 6790994
    Abstract: 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: Grant
    Filed: January 10, 2003
    Date of Patent: September 14, 2004
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Vincent Boschat, Philippe Leconte
  • Patent number: 6790996
    Abstract: 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: Grant
    Filed: October 17, 2002
    Date of Patent: September 14, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Ansmann, Christoph Benisch
  • Patent number: 6677486
    Abstract: 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: Grant
    Filed: November 7, 2001
    Date of Patent: January 13, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
  • Patent number: 6600075
    Abstract: 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: Grant
    Filed: November 13, 2001
    Date of Patent: July 29, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Kelley Moran Whittle, Alan Martin Allgeier, Thomas Papin Gannett, David Page Higley
  • Patent number: 6469211
    Abstract: 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: Grant
    Filed: November 14, 2001
    Date of Patent: October 22, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
  • Patent number: 6399830
    Abstract: 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: Grant
    Filed: December 13, 2000
    Date of Patent: June 4, 2002
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John Nelson Armor, Michael Edward Ford, William Eamon Carroll
  • Patent number: 6380420
    Abstract: 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: Grant
    Filed: September 8, 2000
    Date of Patent: April 30, 2002
    Assignee: Chevron U.S.A. Inc.
    Inventors: William L. Schinski, Michael S. Driver
  • Patent number: 6376714
    Abstract: 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: Grant
    Filed: May 31, 2001
    Date of Patent: April 23, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Alan M. Allgeier, Theodore A. Koch, Sourav K. Sengupta
  • Publication number: 20010005764
    Abstract: 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: Application
    Filed: February 1, 2000
    Publication date: June 28, 2001
    Inventors: Konrad Fischer, Frank Richter, Anatoly Bazanov, Alexandre Timofeev, Natalja Zubritskaya, Galina Smirnova
  • Patent number: 6198002
    Abstract: 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: Grant
    Filed: June 3, 1999
    Date of Patent: March 6, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Karsten Eller, Bernd Fiege, Stefan Rittinger, Eberhard Fuchs
  • Patent number: 6156694
    Abstract: 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: Grant
    Filed: November 5, 1998
    Date of Patent: December 5, 2000
    Assignee: E. I. Dupont De Nemours & Company
    Inventor: Mark Jay Harper
  • Patent number: 6153784
    Abstract: 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: Grant
    Filed: February 17, 1998
    Date of Patent: November 28, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz-Josef Kneuper, Hans-Jurgen Weyer, Horst Neuhauser, Johann-Peter Melder, Andreas Henne, Karl-Heinz Ross, Rainer Becker
  • Patent number: 6087296
    Abstract: 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: Grant
    Filed: November 5, 1998
    Date of Patent: July 11, 2000
    Assignee: E. I. du Pont de Nemours & Co.
    Inventor: Mark Jay Harper
  • Patent number: 6005145
    Abstract: 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: Grant
    Filed: August 3, 1998
    Date of Patent: December 21, 1999
    Assignee: Rhone-Poulenc Fiber and Resin Intermediates
    Inventors: Georges Cordier, Jean-Michel Popa
  • Patent number: 5894074
    Abstract: 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: Grant
    Filed: March 31, 1998
    Date of Patent: April 13, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Fuchs, Boris Breitscheidel, Rainer Becker, Horst Neuhauser
  • Patent number: 5886227
    Abstract: 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: Grant
    Filed: October 28, 1997
    Date of Patent: March 23, 1999
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini Ananda Vedage, Kathryn Sue Hayes
  • Patent number: 5874625
    Abstract: 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: Grant
    Filed: November 4, 1996
    Date of Patent: February 23, 1999
    Assignee: Henkel Corporation
    Inventor: A. Fred Elsasser
  • Patent number: 5869653
    Abstract: 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: Grant
    Filed: October 30, 1997
    Date of Patent: February 9, 1999
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Thomas Albert Johnson
  • Patent number: 5844114
    Abstract: 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: Grant
    Filed: November 14, 1995
    Date of Patent: December 1, 1998
    Assignee: DSM N.V.
    Inventors: Franciscus H.A.M.J. Vandenbooren, Hubertus J.M. Bosman, Jan Van Der Spoel
  • Patent number: 5840989
    Abstract: 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: Grant
    Filed: September 24, 1996
    Date of Patent: November 24, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Georges Cordier, Pierre Fouilloux, Nathalie Laurain
  • Patent number: 5801286
    Abstract: 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: Grant
    Filed: September 23, 1996
    Date of Patent: September 1, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michele Besson, Georges Cordier, Pierre Fouilloux, Jacqueline Masson
  • Patent number: 5789621
    Abstract: 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: Grant
    Filed: August 8, 1996
    Date of Patent: August 4, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Schnurr, Guido Voit, Klemens Flick, Rolf-Hartmuth Fischer
  • Patent number: 5777166
    Abstract: 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: Grant
    Filed: November 25, 1996
    Date of Patent: July 7, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Georges Cordier, Pierre Fouilloux, Nathalie Laurain, Jean-Francis Spindler
  • Patent number: 5763669
    Abstract: 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: Grant
    Filed: June 21, 1996
    Date of Patent: June 9, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Richard Paul Beatty, Rocco Angelo Paciello
  • Patent number: 5760157
    Abstract: 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: Grant
    Filed: December 20, 1996
    Date of Patent: June 2, 1998
    Assignee: Elf Atochem, S.A.
    Inventors: Martine Cerf, Stephane Fouquay, Joel Perthuis
  • Patent number: 5750788
    Abstract: 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: Grant
    Filed: May 19, 1997
    Date of Patent: May 12, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Lukas Haussling, Horst Neuhauser, Wolfgang Paulus
  • Patent number: 5726334
    Abstract: 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: Grant
    Filed: September 19, 1996
    Date of Patent: March 10, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Richard Paul Beatty, Rocco Angelo Paciello
  • Patent number: 5689003
    Abstract: 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: Grant
    Filed: May 8, 1996
    Date of Patent: November 18, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Richard Paul Beatty, Rocco Angelo Paciello
  • Patent number: 5629451
    Abstract: 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: Grant
    Filed: June 30, 1994
    Date of Patent: May 13, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Dennis Hearn, Kyte H. Terhune
  • Patent number: 5597940
    Abstract: 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: Grant
    Filed: March 9, 1995
    Date of Patent: January 28, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Shinzo Seko
  • Patent number: 5571943
    Abstract: 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: Grant
    Filed: March 28, 1995
    Date of Patent: November 5, 1996
    Assignee: Engelhard De Meern B.V.
    Inventors: Frederik Borninkhof, John W. Geus, Michiel J. F. M. Verhaak
  • Patent number: 5557011
    Abstract: 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: Grant
    Filed: November 15, 1994
    Date of Patent: September 17, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Tom Witzel, Eberhard Fuchs
  • Patent number: 5554794
    Abstract: 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: Grant
    Filed: August 18, 1994
    Date of Patent: September 10, 1996
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 5296633
    Abstract: 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: Grant
    Filed: December 30, 1992
    Date of Patent: March 22, 1994
    Inventor: Stephane Fouquay
  • Patent number: 5268509
    Abstract: 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: Grant
    Filed: June 11, 1990
    Date of Patent: December 7, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Dietrich Liebsch, Hans-H. Schwarz, Stephan Wendel, Peter Fischer
  • Patent number: 5266731
    Abstract: 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: Grant
    Filed: July 17, 1991
    Date of Patent: November 30, 1993
    Assignee: Reilly Industries
    Inventors: William M. Ayers, Mary H. Dean
  • Patent number: 5254737
    Abstract: 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: Grant
    Filed: September 17, 1990
    Date of Patent: October 19, 1993
    Assignee: Texaco Chemical Company
    Inventor: Robert L. Zimmerman
  • Patent number: 5254738
    Abstract: 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: Grant
    Filed: February 19, 1991
    Date of Patent: October 19, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Koehler, Hardo Siegel, Matthias Irgang
  • Patent number: 5235108
    Abstract: 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: Grant
    Filed: February 18, 1992
    Date of Patent: August 10, 1993
    Assignee: Engelhard De Meern B.V
    Inventors: Frederik Borninkhof, Eugene G. M. Kuijpers, Pieter H. Berben
  • Patent number: 5196589
    Abstract: 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: Grant
    Filed: September 16, 1991
    Date of Patent: March 23, 1993
    Assignee: LCE Partnership
    Inventors: Anthony J. O'Lenick, Jr., J. Michael Clumpner
  • Patent number: 5166444
    Abstract: 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: Grant
    Filed: March 9, 1992
    Date of Patent: November 24, 1992
    Assignee: Degussa AG
    Inventors: Klaus Hutchmacher, Hermann Schmitt
  • Patent number: 5132427
    Abstract: 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: Grant
    Filed: October 22, 1990
    Date of Patent: July 21, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Koehler, Hardo Siegel, Peter Jaeger, Matthias Irgang