Of Cyano Patents (Class 564/490)
  • 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: 5817589
    Abstract: A process for regenerating a spent hydrogenation catalyst, comprising the steps of providing a catalyst comprising a support material selected from the group consisting of an inorganic oxide-zeolite composite, carbon and zeolite, and a catalytically active metal phase selected from the group consisting of partially reduced group IB metals and completely reduced group VIII metals, said metal phase being present in an amount of grater than or equal to about 0.03 wt %, and said catalyst having an initial diolefin hydrogenation activity, treating a hydrocarbon feedstock having a diolefin content of greater than or equal to about 0.
    Type: Grant
    Filed: April 2, 1996
    Date of Patent: October 6, 1998
    Assignee: Intevep, S.A.
    Inventors: Magdalena Ramirez de Agudelo, Zaida Hernandez de Godoy, Raul Navarro, Julia Guerra
  • 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: 5756306
    Abstract: A process for producing an .alpha.-hydroxy acid or an .alpha.-hydroxyamide which comprises treating an aldehyde and prussic acid or an .alpha.-hydroxynitrile with a microorganism having nitrilase or nitrile hydratase activity in an aqueous medium and maintaining the aldehyde concentration and/or the .alpha.-hydroxynitrile concentration in the reaction mixture within a predetermined range. Also disclosed is a process for producing an .alpha.-hydroxy acid or an .alpha.-hydroxyamide from an aldehyde and prussic acid with a microorganism in an aqueous medium, which comprises maintaining the cyanogen concentration in the reaction mixture within a predetermined range and supplying the aldehyde to the reaction mixture at a predetermined ratio to the prussic acid.
    Type: Grant
    Filed: November 8, 1996
    Date of Patent: May 26, 1998
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Yasumasa Yamaguchi, Masahiro Ushigome, Takeshi Kato
  • Patent number: 5741930
    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: April 28, 1997
    Date of Patent: April 21, 1998
    Assignee: Chemical Research & Licensing Company
    Inventors: Dennis Hearn, Kyte H. Terhune
  • 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: 5723603
    Abstract: The present invention relates to a process for the preparation of lactams from dinitriles.It consists more precisely of a process for the preparation of lactam, linking two stages in series, one of hemihydrogenation of dinitrile to aminonitrile, the other of cyclizing hydrolysis of the aminonitrile after only one simple purification operation.Aliphatic lactams, such as especially epsilon-caprolactam, are base compounds for the preparation of polyamides (polyamide 6 from caprolactam).
    Type: Grant
    Filed: June 17, 1996
    Date of Patent: March 3, 1998
    Assignee: R.P. Fiber & Resin Intermediates
    Inventors: Laurent Gilbert, Nathalie Laurain, Philippe Leconte, Christophe Nedez
  • Patent number: 5712415
    Abstract: A catalyst useful for the simultaneous and selective hydrogenation of diolefins and nitriles present in a hydrocarbon feedstock. The support material is preferably selected from the group consisting of an inorganic oxide-zeolite composite, carbon and zeolite. A catalytically active phase is deposited on the support material. The catalytically active metal phase is selected from the group consisting of partially reduced Group IB metals and completely reduced Group VIII metals. The catalytically active metal phase is present in an amount of .gtoreq.0.03 wt %. A process using the catalyst involves counter current flow of feedstock and hydrogen in the presence of the catalyst.
    Type: Grant
    Filed: January 29, 1997
    Date of Patent: January 27, 1998
    Assignee: Intevep, S.A.
    Inventors: Magdalena Ramirez De Agudelo, Zaida C. Hernandez, Alejandro Granado
  • 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: 5672762
    Abstract: Improved selectivity to tertiary amine production is obtained by the addition of an aliphatic or aromatic halide to the feed during the catalytic hydrogenation of saturated or unsaturated aliphatic or cycloaliphatic nitriles.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: September 30, 1997
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini Ananda Vedage, John Nelson Armor
  • Patent number: 5663446
    Abstract: A catalyst useful for the simultaneous and selective hydrogenation of diolefins and nitriles present in a hydrocarbon feedstock. The support material is preferably selected from the group consisting of an inorganic oxide-zeolite composite, carbon and zeolite. A catalytically active phase is deposited on the support material. The catalytically active metal phase is selected from the group consisting of partially reduced Group IB metals and completely reduced Group VIII metals. The catalytically active metal phase is present in an amount of .gtoreq.0.03 wt %.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: September 2, 1997
    Assignee: Intevep, S.A.
    Inventors: Magdalena Ramirez de Agudelo, Julia Guerra, Trino Romero, Mariela Medina
  • Patent number: 5663445
    Abstract: A process for the catalytic preparation of alcohols or amines by reaction of esters, fatty acids, or nitriles with hydrogen at elevated temperature and pressure. The unreduced catalyst contains, per 100 parts by weight of CuO, 40 to 130 parts by weight of ZnO, 2 to 50 parts by weight of Al.sub.2 O.sub.3, and optionally 0.5 to 8 parts by weight of oxide of Mn, Mo, V, Zr, and/or alkaline earth metal. It has a BET total area of 80 to 175 m.sup.2 /g of catalyst in the unreduced state, and 75% to 95% of the BET total area is formed by pores having a radius r.sub.p .ltoreq.15 nm.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: September 2, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhardt Horn, Carl Dieter Frohning
  • Patent number: 5648545
    Abstract: Catalysts consisting of from 85 to 100 wt % of copper oxide and zirconium oxide and from 15 to 0 wt % of metal oxides of the subgroups Ib to VIIb and VIII of the Periodic Table and a process for the preparation of amines from nitriles and nitrogen compounds selected from the group comprising ammonia and primary and secondary amines, at temperatures of from 80.degree. to 250.degree. C. and pressures of from 1 to 400 bar using hydrogen in the presence of said catalysts.
    Type: Grant
    Filed: July 5, 1995
    Date of Patent: July 15, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reif, Michael Hesse, Horst Zimmermann, Heinz Lingk
  • 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: 5574189
    Abstract: This invention relates to an improvement in a process for the production of amines and particularly secondary amines by the hydrogenation of aliphatic and aromatic nitriles. The improvement resides in the use of a multi-metallic catalyst, preferably a bimetallic catalyst comprising nickel or cobalt in combination with rhodium, ruthenium or palladium. Optionally, the catalyst is carried on an alumina support.
    Type: Grant
    Filed: February 2, 1995
    Date of Patent: November 12, 1996
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini A. Vedage, John N. Armor
  • 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: 5550297
    Abstract: A process for catalytic preparation of alcohols or amines by reaction of esters, fatty acids, or nitriles with hydrogen at elevated temperature and pressure. The unreduced catalyst contains, per 100 parts by weight of CuO, 40 to 130 parts by weight of ZnO, 2 to 50 parts by weight of Al.sub.2 O.sub.3, and optionally 0.5 to 8 parts by weight of oxide of Mn, Mo, V, Zr, and/or alkaline earth metal. It has a BET total area of 80 to 175 m.sup.2 /g of catalyst in the unreduced state, and 75% to 95% of the BET total area is formed by pores having a radius r.sub.p .ltoreq.15 nm.
    Type: Grant
    Filed: February 16, 1995
    Date of Patent: August 27, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhardt Horn, Carl D. Frohning
  • Patent number: 5527949
    Abstract: A method for making an amine includes the steps of heating a reaction mixture including a nitrile, an acid, water and a substrate compound capable of generating a carbonium ion by reaction with the acid to generate a first reaction intermediate; treating the first reaction intermediate with an acid in the presence of a primary alkanol to form a second reaction intermediate and an alkyl ester; separating the alkyl ester from the second reaction intermediate; and treating the second reaction intermediate with a base to form the amine.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: June 18, 1996
    Assignee: Rohm and Haas Company
    Inventors: Sudhir K. Agarwal, Rajiv M. Banavali, Bharati D. Chheda, Samuel F. Reed, Jr.
  • Patent number: 5504253
    Abstract: A method of making (R)-N- 1-(3-methoxyphenyl)ethyl!-3-(2-chlorobenzene)propanamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of (R)-3-methoxy-.alpha.-methylbenzylamine. A method of condensing a nitrile with a primary or secondary amine to form an imine involves the reaction of a nitrile with diisobutylaluminum hydride; and then reacting the resultant compound with a primary or secondary amine to form the imine. The process is especially useful for producing enantiomerically pure chiral imines, and, ultimately, amines. Typical such imines have the formula: ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, aryl and aralkyl.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: April 2, 1996
    Assignee: NPS Pharmaceuticals, Inc.
    Inventors: Bradford C. VanWagenen, Thomas E. D'Ambra
  • Patent number: 5463130
    Abstract: A process for the preparation of peralkylated amines of the general formula I ##STR1## in which R.sup.1, R.sup.2 denote C.sub.1 -C.sub.200 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.20 alkylcycloalkyl, C.sub.4 -C.sub.20 cycloalkylalkyl, C.sub.2 -C.sub.20 alkoxyalkyl, aryl, C.sub.7 -C.sub.20 alkylaryl, C.sub.7 -C.sub.20 aralkyl, C.sub.2 -C.sub.8 hydroxyalkyl, C.sub.2 -C.sub.8 mercaptoalkyl, C.sub.8 -C.sub.20 phenoxyalkyl, C.sub.2 -C.sub.8 aminoalkyl, C.sub.2 -C.sub.8 (NHR.sup.4)alkyl, C.sub.2 -C.sub.8 (NR.sup.4 R.sup.5)alkyl or together form a saturated or unsaturated C.sub.2 -C.sub.6 alkylene chain optionally mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl and optionally interrupted by oxygen or nitrogenX denotes a C.sub.2 -C.sub.20 alkylene or C.sub.2 -C.sub.20 alkenylene or C.sub.4 -C.sub.8 cycloalkylene chain optionally mono- to penta-substituted by R.sup.3, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 dialkylamino, phenoxy, diphenylamino and/or C.sub.2 -C.sub.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: October 31, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Tom Witzel, Eberhard Fuchs, Horst Zimmermann
  • Patent number: 5371292
    Abstract: 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: Grant
    Filed: July 15, 1993
    Date of Patent: December 6, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Wolfgang Harder
  • Patent number: 5321161
    Abstract: Nitriles can be hydrogenated to amines by heating the nitrile in the presence of hydrogen and a tungsten carbide catalyst, such as are formed by the calcination of a tungsten salt with an acyclic compound containing-nitrogen-hydrogen bonding.
    Type: Grant
    Filed: May 17, 1993
    Date of Patent: June 14, 1994
    Assignee: Akzo nv
    Inventors: Willem Vreugdenhil, Fawzy G. Sherif, Johst H. Burk, James F. Gadberry
  • Patent number: 5306821
    Abstract: This invention relates to a novel process for the preparation of tertiary carbinamines by double addition of organolanthanide reagents, especially organocerium reagents, to nitriles. It further relates to the preparation of such amines by the addition of organolanthanide reagents to imines.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: April 26, 1994
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventor: Engelbert Ciganek
  • 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: 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: 5239120
    Abstract: 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: Grant
    Filed: March 27, 1991
    Date of Patent: August 24, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Claus-Ulrich Priester, Gerhard Koppenhoefer, Wolfgang Harder, Tom Witzel, Helmut Lermer, Ulrich Koehler
  • 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: 5196601
    Abstract: Disclosed herein is a process for producing an alcohol or an amine by reducing a compound having a formyl, keto, nitro, oxirane, ester, nitrile, amide or halogenated carboxyl group with an alkali metal boro-hydride in the presence of a compound having a hydroxyl group and ether linkage. According to the present invention, a functional group having a great steric hindrance can be reduced, and a corresponding alcohol or amine can efficiently be produced under very mild conditions on an industrial scale.
    Type: Grant
    Filed: June 17, 1992
    Date of Patent: March 23, 1993
    Assignee: Kao Corporation
    Inventors: Tomohito Kitsuki, Yoshiaki Fujikura
  • 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: 5166443
    Abstract: A process for the preparation of a 2,2-disubstituted pentane-1,5-diamine of the formula I ##STR1## where R.sup.1 and R.sup.2, independently of one another, are C.sub.1 - to C.sub.10 -alkyl or C.sub.2 - to C.sub.10 -alkenyl or together are a C.sub.4 - to C.sub.7 -alkylene chain which is unsubstituted or monosubstituted to pentasubstituted by C.sub.1 - to C.sub.4 -alkyl, from a 2,2-disubstituted 4-cyanobutanal of the formula II ##STR2## where R.sup.1 and R.sup.2 are as defined above, comprises, in two spatially separate reaction spaces,a) reacting the 4-cyanobutanal of the formula II, in a first reaction space, with excess ammonia on an acidic heterogeneous catalyst at from 20.degree. to 150.degree. C.
    Type: Grant
    Filed: March 17, 1991
    Date of Patent: November 24, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Ludwig Schuster
  • Patent number: 5130491
    Abstract: A method for producing secondary amines, particularly fatty secondary amines such as ditallowamine from fatty nitriles, such as tallow nitrile over a nickel catalyst promoted with copper, chromium and molybdenum has been discovered. The reaction gives high selectivity of secondary amine over the coproduced primary and tertiary amines. The reaction may be conducted continuously in the presence of ammonia and hydrogen. The secondary amine proportion may be increased by a second stage using the same catalyst as the first stage, but in the absence of ammonia. The same catalyst may be used in both steps if a two stage process is used.
    Type: Grant
    Filed: September 17, 1990
    Date of Patent: July 14, 1992
    Assignee: Texaco Chemical Company
    Inventor: Robert L. Zimmerman
  • Patent number: 5124485
    Abstract: A method of preparation of a cobalt catalyst particularly adapted for hydrogenation of nitriles, the catalyst which is the product of the method, and the method of use thereof.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: June 23, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Volker Falk, Gerhardt Horn, Hanswilhelm Bach, Klaus Mathieu, Claus Kniep
  • Patent number: 5101075
    Abstract: Bis- and tris-(3-dimethylaminopropyl)-amine can be prepared by catalytic hydrogenation of 3-(dimethylamino)-propionitrile with a palladium catalyst on an Al.sub.2 O.sub.3 -containing support.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: March 31, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Josef Kasbauer, Helmut Fiege, Wolfgang Kiel
  • Patent number: 5097073
    Abstract: Disclosed is a process for preparing an unsaturated aliphatic primary or secondary amine from the corresponding unsaturated aliphatic nitrile without hydrogenating an olefinic bond in the molecule. The process employs a catalyst which is a combination of copper and a specific metal.
    Type: Grant
    Filed: June 12, 1991
    Date of Patent: March 17, 1992
    Assignee: Kao Corporation
    Inventors: Hiroshi Abe, Tohru Katoh, Hisakazu Tajima, Kohshiro Sotoya
  • Patent number: 5081305
    Abstract: This invention relates to a process for the separation of acrylonitrile used in the cyanoethylation of glycols to produce a bis(cyanoethylated) aliphatic glycol from the resulting glycol which is then reduced with hydrogen to produce the corresponding bis(aminopropoxy) alkane. In this process, acrylonitrile or methacrylonitrile is reacted with an aliphatic glycol in stoichiometric excess and the acrylonitrile removed from the cyanoethylated glycol by reaction with aliphatic primary or secondary alcohol prior to effecting the hydrogenation of the cyanoethylated aliphatic glycol in the presence of the acrylonitrile-amine reaction product. The reaction product then can be separated by conventional techniques such as distillation.
    Type: Grant
    Filed: October 13, 1988
    Date of Patent: January 14, 1992
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Richard V. C. Carr, Steven M. Galaton, Thomas A. Johnson, Thomas A. Albanese
  • Patent number: 5075506
    Abstract: A method for producing secondary amines, particularly fatty secondary amines such as ditallowamine from fatty nitriles, such as tallow nitrile over a cobalt catalyst promoted with zirconium has been discovered. The catalyst may be supported on kieselguhr or other support. The reaction gives high selectivity or secondary amine over the coproduced primary and tertiary amines. The reaction may be conducted continuously in the presence of ammonia and hydrogen. The secondary amine proportion may be increased by a second stage using the same catalyst as the first stage, but in the absence of ammonia.
    Type: Grant
    Filed: April 10, 1990
    Date of Patent: December 24, 1991
    Assignee: Texaco Chemical Company
    Inventor: Robert L. Zimmerman
  • Patent number: 5075507
    Abstract: This invention relates to a process for the separation of acrylonitrile used in the cyanoethylation of glycols to produce a bis(cyanoethylated) aliphatic glycol from the resulting glycol which is then reduced with hydrogen to produce the corresponding bis(aminopropyl) aliphatic glycol. In this process, acrylonitrile is reacted with an aliphatic glycol in stoichiometric excess and the acrylonitrile removed from the cyanoethylated glycol by reaction with aliphatic primary or secondary amine prior to effecting the hydrogenation of the cyanoethylated aliphatic glycol in the presence of the acrylonitrile-amine reaction product. The reaction product then can be separated by conventional techniques such as distillation.
    Type: Grant
    Filed: August 1, 1988
    Date of Patent: December 24, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Richard V. C. Carr, Thomas A. Johnson, Steven M. Galaton, Thomas A. Albanese
  • Patent number: 5047178
    Abstract: The invention provides a nickel/alumina catalyst, with an atomic ratio of nickel/aluminium between 10 and 2, an active nickel surface area between 70 and 150 m.sup.2 /g nickel and an average pore size, depending on the above atomic ratio, between 4 and 20 nanometers. Preferably the nickel/aluminium atomic ratio is between 10 and 4. Preferably the catalyst has a specific porous structure.The invention also provides a method for preparing the catalyst by a two step process involving precipitating nickel ions and adding during a second, so-called ageing step a soluble aluminium compound.The catalyst is useful for hydrogenating unsaturated organic compounds in particular oils.
    Type: Grant
    Filed: June 27, 1990
    Date of Patent: September 10, 1991
    Assignee: Unilever Patent Holdings B.V.
    Inventors: Keshab L. Ganguli, Peter Nootenboom, Cornelis K. Lok
  • Patent number: 5034560
    Abstract: Disclosed is a process for making ethylamines by the hydrogenation in a reaction zone of acetonitrile contained in a basic aqueous solution which also contains HCN, which comprises continuously passing hydrogen gas in contact with a flowing stream containing acetonitrile, water and HCN, which stream is in contact with a solid hydrogenation catalyst, wherein the hydrogen contact time is in the range from 0.5 seconds to 20 minutes and the molar ratio of H.sub.2 to acetonitrile charged to said reaction zone is in the range 2-200:1.
    Type: Grant
    Filed: October 19, 1990
    Date of Patent: July 23, 1991
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, Robert A. Dubbert
  • Patent number: 4990672
    Abstract: This invention relates to propylene-linked polyethylene polyamines and a process for preparing such propylene-linked polyethylene polyamines. These propylene-linked polyethylene polyamines are characterized as having high molecular weight and the amine value is distributed over a wide range of primary, secondary, and tertiary amine functionality.The propylene-linked polyethylene polyamines are prepared by reacting a polyamine containing an ethylene amine functionality with acrylonitrile or methacrylonitrile to form a cyanoethylated polyamine containing the ethylene linkage and then reductively alkylating the resulting cyanoethylated derivative in the presence of a polyamine containing an ethylene linkage. Typically, a polyethylene polyamine such as diethylenetriamine or triethylene tetramine is reacted with acrylonitrile and then hydrogenated under reductive alkylation conditions.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: February 5, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Thomas A. Johnson, Ismail O. Abdalmuhdi
  • Patent number: 4967006
    Abstract: This invention relates to a process for the coproduction of propanediamines and alkylated aminopropanediamines. The process contemplates an initial cyanoethylation of ammonia under conditions for producing aminopropionitrile and modest levels of iminobispropionitrile. After separation of the iminobispropionitrile from the aminopropionitrile, the process involves the catalytic reductive alkylation of the iminobispropionitrile by reaction with an aldehyde in the presence of hydrogen to form the alkylated iminobispropionitrile followed by the catalytic hydrogenation of the nitrile group in aminopropionnitrile and iminobispropionitrile to the amine.
    Type: Grant
    Filed: April 7, 1989
    Date of Patent: October 30, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Richard V. C. Carr
  • Patent number: 4895994
    Abstract: Catalysts made by the Raney process (e.g., Raney process nickel) pelletized in matrix of polymer and plasticizer are activated by either (a) removal of plasticizer (e.g., by solvent extraction) followed by leaching out Al with caustic solution, leaving an active catalyst made by the Raney process in a polymer matrix; or (b) removal of plasticizer, then calcining to remove polymer, followed by leaching with caustic. The activated catalyst pellets have sufficient strength and attrition resistance for efficient use in fixed beds and packed columns for superior hydrogenation of toluene, heptene, butyraldehyde, and other conventional feedstockers used with catalysts made by the Raney process.
    Type: Grant
    Filed: October 18, 1988
    Date of Patent: January 23, 1990
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Wu-Cheng Cheng, Christian B. Lundsager, Robert M. Spotnitz
  • Patent number: 4885391
    Abstract: A process for the hydrogenation of C.sub.4 to C.sub.12 nitriles using a Raney cobalt catalyst promoted with chromium in which the catalyst activity is maintained by the addition of water. The process is particularly attractive to produce diamines by the hydrogenation of dinitriles.
    Type: Grant
    Filed: January 14, 1988
    Date of Patent: December 5, 1989
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Frank E. Herkes
  • Patent number: 4845297
    Abstract: Process for producing polyamines by a catalytic reduction reaction of a cyanoethylated N-(2-aminoethyl)piperazine and cyanoethylated compounds of polyamines containing 4 or more amino groups in the molecule.
    Type: Grant
    Filed: December 30, 1987
    Date of Patent: July 4, 1989
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
  • Patent number: 4845298
    Abstract: A process for selectively preparing an unsaturated long-chain aliphatic secondary amine at a high yield comprising reducing an unsaturated aliphatic nitrile having 8 to 22 carbon atoms or a nitrile mixture containing said nitrile with hydrogen in the presence of a Ni hydrogenation catalyst and a carboxylic acid amide at a reaction temperature of 160.degree. C. to 200.degree. C.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: July 4, 1989
    Assignee: Lion Akzo Company Limited
    Inventors: Takeo Inagaki, Akira Fukasawa, Hiroshi Yamagishi