Of Cyano Patents (Class 564/490)
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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: 5817589Abstract: 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: GrantFiled: April 2, 1996Date of Patent: October 6, 1998Assignee: Intevep, S.A.Inventors: Magdalena Ramirez de Agudelo, Zaida Hernandez de Godoy, Raul Navarro, Julia Guerra
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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: 5756306Abstract: 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: GrantFiled: November 8, 1996Date of Patent: May 26, 1998Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Yasumasa Yamaguchi, Masahiro Ushigome, Takeshi Kato
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Patent number: 5741930Abstract: 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: April 28, 1997Date of Patent: April 21, 1998Assignee: Chemical Research & Licensing CompanyInventors: Dennis Hearn, Kyte H. Terhune
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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: 5723603Abstract: 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: GrantFiled: June 17, 1996Date of Patent: March 3, 1998Assignee: R.P. Fiber & Resin IntermediatesInventors: Laurent Gilbert, Nathalie Laurain, Philippe Leconte, Christophe Nedez
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Patent number: 5712415Abstract: 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: GrantFiled: January 29, 1997Date of Patent: January 27, 1998Assignee: Intevep, S.A.Inventors: Magdalena Ramirez De Agudelo, Zaida C. Hernandez, Alejandro Granado
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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: 5672762Abstract: 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: GrantFiled: April 12, 1996Date of Patent: September 30, 1997Assignee: Air Products and Chemicals, Inc.Inventors: Gamini Ananda Vedage, John Nelson Armor
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Patent number: 5663446Abstract: 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: GrantFiled: January 16, 1996Date of Patent: September 2, 1997Assignee: Intevep, S.A.Inventors: Magdalena Ramirez de Agudelo, Julia Guerra, Trino Romero, Mariela Medina
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Patent number: 5663445Abstract: 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: GrantFiled: May 30, 1995Date of Patent: September 2, 1997Assignee: Hoechst AktiengesellschaftInventors: Gerhardt Horn, Carl Dieter Frohning
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Patent number: 5648545Abstract: 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: GrantFiled: July 5, 1995Date of Patent: July 15, 1997Assignee: BASF AktiengesellschaftInventors: Wolfgang Reif, Michael Hesse, Horst Zimmermann, Heinz Lingk
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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: 5574189Abstract: 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: GrantFiled: February 2, 1995Date of Patent: November 12, 1996Assignee: Air Products and Chemicals, Inc.Inventors: Gamini A. Vedage, John N. Armor
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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: 5550297Abstract: 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: GrantFiled: February 16, 1995Date of Patent: August 27, 1996Assignee: Hoechst AktiengesellschaftInventors: Gerhardt Horn, Carl D. Frohning
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Patent number: 5527949Abstract: 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: GrantFiled: August 23, 1994Date of Patent: June 18, 1996Assignee: Rohm and Haas CompanyInventors: Sudhir K. Agarwal, Rajiv M. Banavali, Bharati D. Chheda, Samuel F. Reed, Jr.
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Patent number: 5504253Abstract: 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: GrantFiled: July 15, 1994Date of Patent: April 2, 1996Assignee: NPS Pharmaceuticals, Inc.Inventors: Bradford C. VanWagenen, Thomas E. D'Ambra
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Patent number: 5463130Abstract: 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: GrantFiled: February 28, 1995Date of Patent: October 31, 1995Assignee: BASF AktiengesellschaftInventors: Tom Witzel, Eberhard Fuchs, Horst Zimmermann
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Patent number: 5371292Abstract: A process for the preparation of 3-aminomethyl-3,5,5-trimethyl-cyclohexylamine from 3-cyano-3,5,5-trimethyl-cyclohexanone, wherein the following stages are carried out in discrete reaction chambers:a) the 3-cyano-3,5,5-trimethyl-cyclohexanone is reacted in a first reaction chamber with excess ammonia over an acidic metal oxide catalyst at a temperature of from 20.degree. to 150.degree. C. and a pressure of from 15 to 500 bar, andb) in a second reaction chamber, the reaction product from stage a) is hydrogenated with hydrogen at a temperature of from 60.degree. to 150.degree. C. and a pressure of from 50 to 300 bar in the presence of excess ammonia over a catalyst containing cobalt, nickel, ruthenium, and/or some other noble metal, which catalyst optionally contains a basic component or is supported by neutral or basic supporting material.Type: GrantFiled: July 15, 1993Date of Patent: December 6, 1994Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Wolfgang Harder
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Patent number: 5321161Abstract: 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: GrantFiled: May 17, 1993Date of Patent: June 14, 1994Assignee: Akzo nvInventors: Willem Vreugdenhil, Fawzy G. Sherif, Johst H. Burk, James F. Gadberry
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Patent number: 5306821Abstract: 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: GrantFiled: January 10, 1992Date of Patent: April 26, 1994Assignee: The Du Pont Merck Pharmaceutical CompanyInventor: Engelbert Ciganek
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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: 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: 5239120Abstract: A process for the preparation of a 2-(3-aminopropyl)-cycloalkylamine of the general formula I ##STR1## in which the subscript n is an integer from 1 to 4, from a 2-(2-cyanoethyl)-cycloalkanone of the general formula II ##STR2## in which the subscript n has the meaning stated, wherein the following stages are carried out in discrete reaction chambers:a) the 2-(2-cyanoethyl)-cycloalkanone of formula II is reacted in a first reaction chamber with excess ammonia over an acidic heterogeneous catalyst at a temperature from 20.degree. to 150.degree. C. and a pressure of from 15 to 500 bar, andb) in a second reaction chamber, the reaction product from stage a) is hydrogenated at a temperature of from 60.degree. to 150.degree. C. and a pressure of from 50 to 300 bar in the presence of excess ammonia over a catalyst containing cobalt, nickel, ruthenium, and/or some other noble metal, which catalyst optionally contains a basic component or is supported on neutral or basic supporting material.Type: GrantFiled: March 27, 1991Date of Patent: August 24, 1993Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Gerhard Koppenhoefer, Wolfgang Harder, Tom Witzel, Helmut Lermer, Ulrich Koehler
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Patent number: 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: 5196601Abstract: 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: GrantFiled: June 17, 1992Date of Patent: March 23, 1993Assignee: Kao CorporationInventors: Tomohito Kitsuki, Yoshiaki Fujikura
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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: 5166443Abstract: 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: GrantFiled: March 17, 1991Date of Patent: November 24, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Claus-Ulrich Priester, Tom Witzel, Gerhard Koppenhoefer, Ludwig Schuster
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Patent number: 5130491Abstract: 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: GrantFiled: September 17, 1990Date of Patent: July 14, 1992Assignee: Texaco Chemical CompanyInventor: Robert L. Zimmerman
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Patent number: 5124485Abstract: 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: GrantFiled: July 26, 1990Date of Patent: June 23, 1992Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Volker Falk, Gerhardt Horn, Hanswilhelm Bach, Klaus Mathieu, Claus Kniep
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Patent number: 5101075Abstract: 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: GrantFiled: October 2, 1990Date of Patent: March 31, 1992Assignee: Bayer AktiengesellschaftInventors: Josef Kasbauer, Helmut Fiege, Wolfgang Kiel
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Patent number: 5097073Abstract: 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: GrantFiled: June 12, 1991Date of Patent: March 17, 1992Assignee: Kao CorporationInventors: Hiroshi Abe, Tohru Katoh, Hisakazu Tajima, Kohshiro Sotoya
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Patent number: 5081305Abstract: 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: GrantFiled: October 13, 1988Date of Patent: January 14, 1992Assignee: Air Products and Chemicals, Inc.Inventors: Richard V. C. Carr, Steven M. Galaton, Thomas A. Johnson, Thomas A. Albanese
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Patent number: 5075506Abstract: 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: GrantFiled: April 10, 1990Date of Patent: December 24, 1991Assignee: Texaco Chemical CompanyInventor: Robert L. Zimmerman
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Patent number: 5075507Abstract: 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: GrantFiled: August 1, 1988Date of Patent: December 24, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Richard V. C. Carr, Thomas A. Johnson, Steven M. Galaton, Thomas A. Albanese
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Patent number: 5047178Abstract: 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: GrantFiled: June 27, 1990Date of Patent: September 10, 1991Assignee: Unilever Patent Holdings B.V.Inventors: Keshab L. Ganguli, Peter Nootenboom, Cornelis K. Lok
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Patent number: 5034560Abstract: 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: GrantFiled: October 19, 1990Date of Patent: July 23, 1991Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Robert A. Dubbert
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Patent number: 4990672Abstract: 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: GrantFiled: May 30, 1989Date of Patent: February 5, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Thomas A. Johnson, Ismail O. Abdalmuhdi
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Patent number: 4967006Abstract: 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: GrantFiled: April 7, 1989Date of Patent: October 30, 1990Assignee: Air Products and Chemicals, Inc.Inventor: Richard V. C. Carr
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Patent number: 4895994Abstract: 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: GrantFiled: October 18, 1988Date of Patent: January 23, 1990Assignee: W. R. Grace & Co.-Conn.Inventors: Wu-Cheng Cheng, Christian B. Lundsager, Robert M. Spotnitz
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Patent number: 4885391Abstract: 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: GrantFiled: January 14, 1988Date of Patent: December 5, 1989Assignee: E. I. Du Pont De Nemours and CompanyInventor: Frank E. Herkes
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Patent number: 4845297Abstract: 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: GrantFiled: December 30, 1987Date of Patent: July 4, 1989Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
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Patent number: 4845298Abstract: 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: GrantFiled: January 27, 1987Date of Patent: July 4, 1989Assignee: Lion Akzo Company LimitedInventors: Takeo Inagaki, Akira Fukasawa, Hiroshi Yamagishi