Preparing Hexamethylene Diamine Patents (Class 564/492)
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Patent number: 6359178Abstract: A process for catalytic hydrogenation of adiponitrile to hexamethylenediamine at elevated temperature and elevated pressure in the presence of catalysts based on elemental iron as catalytically active component and ammonia as solvent comprises a) hydrogenating adiponitrile at from 70 to 220° C.Type: GrantFiled: February 13, 2001Date of Patent: March 19, 2002Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Peter Bassler, Hermann Luyken, Frank Ohlbach, Johann-Peter Melder, Martin Merger, Andreas Ansmann, Alwin Rehfinger, Guido Voit
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Patent number: 6281388Abstract: A method for the production of an amine from a nitrile utilizing hydrogenation by; feeding hydrogen and nitrile into a reactor including catalyst, water and inorganic base to form a reaction medium; mixing the reaction medium to provide a uniform bulk concentration of the nitrile in at least one direction across the reactor to minimize the reactor volume where local bulk nitrile concentration exceeds that stoichiometrically required to completely deplete the local bulk hydrogen concentration; and hydrogenating the nitrile to form the amine.Type: GrantFiled: December 13, 1999Date of Patent: August 28, 2001Assignee: Solutia Inc.Inventors: Ralph T. Goodwin, III, Gregory J. Ward
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Patent number: 6278023Abstract: A process for preparing aliphatic alpha, omega-diamines by hydrogenation of aliphatic alpha, omega-dinitriles in the presence of a catalyst comprises using a hydrogenation catalyst comprising (a) iron or a compound based on iron or mixtures thereof, (b) from 0.001 to 0.3% by weight based on (a) of a promoter based on 2, 3, 4 or 5 elements selected from the group consisting of aluminum, silicon, zirconium, titanium and vanadium, and also (c) from 0 to 0.3% by weight based on (a) of a compound based on an alkali and/or alkaline earth metal.Type: GrantFiled: August 23, 2000Date of Patent: August 21, 2001Assignee: BASF AktiengesellschaftInventors: Guido Voit, Rolf Fischer, Peter Bassler, Andreas Ansmann, Hermann Luyken, Martin Merger, Frank Ohlbach, Alwin Rehfinger
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Patent number: 6248926Abstract: A method for separating a mixture of hexamethylenediamine, aminocapronitile and polarographically reducible impurities using fractional distillation in which the temperature in the rectifying zone of a distillation column varies sigmoidally along its length to force a major portion of the PRI to co-distill with the aminocapronitrile.Type: GrantFiled: October 26, 2000Date of Patent: June 19, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: John J. Ostermaier, Leon S. Scott
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Patent number: 6222059Abstract: A process for preparing aliphatic alpha,omega-amino nitrites by partial hydrogenation of aliphatic alpha,omega-dinitriles in the presence of a catalyst, wherein the catalyst used for the partial hydrogenation comprises (a) iron or a compound based on iron or mixtures thereof and (b) from 0.01 to 5% by weight, based on (a), of a promoter based on 2,3,4 or 5 elements selected from the group consisting of aluminum, silicon, zirconium, titanium and vanadium and (c) from 0 to 5% by weight, based on (a), of a compound based on an alkali metal or alkaline earth metal.Type: GrantFiled: March 10, 1999Date of Patent: April 24, 2001Assignee: BASF AktiengesellschaftInventors: Klaus Ebel, Rolf Fischer, Klemens Flick, Martin Merger, Guido Voit
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Patent number: 6198002Abstract: A process for preparing a secondary or tertiary 2-methyl-1,5-pen-tanediamine of the formula I where R1 and R2 are H, C1-C20-alkyl, C3-C8-cycloalkyl, aryl, C7-C20-arylalkyl, where the radicals R1 and R2 may bear substituents selected from the group consisting of C1-C20-alkyl, C1-C20-alkoxy, C6-C20-aryloxy and hydroxy, and R1 and R2 are not simultaneously hydrogen, or R1 and R2 are together an unsubstituted or C1-C20-alkyl- and/or C1-C20-alkoxy-substituted C3-C7-alkylene chain which may, if desired, be interrupted by one or two O or NR3 groups, where R3 is H or C1-C20-alkyl comprises reacting 2-methylglutarodinitrile with a primary or secondary amine of the formula R1R2NH and hydrogen at from 50 to 250° C. and pressures of from 0.5 to 35 MPa in the presence of an oxidic supported catalyst comprising one or more noble metals which has been treated with hydrogen at from 50 to 300° C. for at least 0.5 hour before use.Type: GrantFiled: June 3, 1999Date of Patent: March 6, 2001Assignee: BASF AktiengesellschaftInventors: Karsten Eller, Bernd Fiege, Stefan Rittinger, Eberhard Fuchs
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Patent number: 6153784Abstract: Halides are removed from halide-containing nitrile mixtures by(a) thermally treating the halide-containing nitrile mixture,(b) subsequently adding a base to the thermally treated nitrile mixture and(c) subsequently separating off the base from the nitrile mixture.Amines are prepared by(A) reacting alkyl halides with metal cyanides in an at least two-phase reaction medium in the presence of halide-containing phase-transfer catalysts to give alkanenitriles,(B) separating off the resulting halide-containing alkanenitrile mixture phase and(C) further treating the halide-containing alkanenitrile mixture phase, as described in the stages(a)-(c) removing halides from halide-containing nitrile mixtures and(d) hydrogenating nitrites obtained in stage (c) to give amines, in the presence of suspended or fixed-bed catalysts.Type: GrantFiled: February 17, 1998Date of Patent: November 28, 2000Assignee: BASF AktiengesellschaftInventors: Heinz-Josef Kneuper, Hans-Jurgen Weyer, Horst Neuhauser, Johann-Peter Melder, Andreas Henne, Karl-Heinz Ross, Rainer Becker
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Patent number: 6139693Abstract: A process for recovering hexamethylenediamine (I) from a mixture (II) including(I) hexamethylenediamine,(III) hexamethyleneimine,(IV) a compound selected from 2-aminomethylcyclopentylamine and 1,2-diaminocyclohexane,(V) an imine,(VI) adiponitrile and 6-aminocapronitrileincludes distilling(a) a mixture (II) to obtain(a1) a low boiling fraction (III),(a2) a medium boiling fraction (VII) (I), (IV) and (V), and(a3) a high boiling fraction (V) and (VI),(b) a mixture (VII) to obtain(b1) an overhead product (IV), and(b2) a mixture (VIII) (I) and (V) as bottom product, and(c) a mixture (VIII) to obtain(c1) (I) as overhead product, and(c2) a bottom product (V).Type: GrantFiled: August 9, 1999Date of Patent: October 31, 2000Assignee: BASF Aktiengesellschaft LudwigshafenInventors: Peter Bassler, Rolf Fischer, Hermann Luyken, Alwin Rehfinger, Guido Voit
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Patent number: 6005145Abstract: The present invention relates to new metal compounds, to a process for the preparation of these metal compounds and to their use as catalysts.The new metal compounds according to the invention have, when they are used as catalysts, in particular as hydrogenation catalysts, an efficiency of the same order as that obtained with Raney nickel or cobalt.These metal compounds are more precisely compounds containing one or a number of divalent metals at least partially in the reduced state, bulked by a phase comprising one or a number of doping metals chosen from chromium, molybdenum, iron, manganese, titanium, vanadium, gallium, indium, bismuth, yttrium, cerium, lanthanum and the other trivalent lanthanides, in the form of oxides.Type: GrantFiled: August 3, 1998Date of Patent: December 21, 1999Assignee: Rhone-Poulenc Fiber and Resin IntermediatesInventors: Georges Cordier, Jean-Michel Popa
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Patent number: 5900511Abstract: A process for continuous hydrogenation of adiponitrile (ADN) to hexamethylene diamine (HMD) and optionally to amninocapronitrile (ACN) involving the catalytic hydrogenation of adiponitrile at relatively low temperature (e.g., 75.degree. C.) and pressure (e.g., 500 psig) using a sponge cobalt catalyst (Raney.RTM. Co) in a reaction medium that is substantially free of caustic. In such a process periodic addition of water controls the production of side reaction products and the periodic addition of ammonium hydroxide rejuvenates the catalyst. Hexamethylene diamine is an important intermediate for the synthesis of polyamides such as Nylon-6,6 and aminocapronitrile is a potential intermediate of Nylon-6.Type: GrantFiled: March 26, 1998Date of Patent: May 4, 1999Assignee: E. I. de Pont de Nemours and CompanyInventors: Sourav Kumar Sengupta, Theodore Augur Koch, Karl Robert Krause
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Patent number: 5894074Abstract: A process for preparing amines of the general formula (I)X(--CH.sub.2 --NR.sup.1 R.sup.2).sub.n (I)whereR.sup.1 and R.sup.2 are preferably methyl, X is preferably 1,4-butylene and n is preferably 2, comprises reacting nitriles of the general formula (II)(R.sup.1 R.sup.2 N--CH.sub.2 --).sub.n-m X(--CN).sub.m (II)where R.sup.1, R.sup.2 and X are each as defined above and m is an integer from 1 to n,with secondary amines of the general formula (III)HNR.sup.1 R.sup.2 (III)where R.sup.1 and R.sup.2 are each as defined above,and hydrogen at from 50 to 250.degree. C. and from 5 to 350 bar in the presence of a palladium catalyst comprising, based on the total weight of the catalyst, from 0.1 to 10% by weight of Pd and from 0.01 to 10% by weight of at least one further metal selected from groups IB and VII of the Periodic Table, cerium and lanthanum on a support.Type: GrantFiled: March 31, 1998Date of Patent: April 13, 1999Assignee: BASF AktiengesellschaftInventors: Eberhard Fuchs, Boris Breitscheidel, Rainer Becker, Horst Neuhauser
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Patent number: 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: 5840989Abstract: The invention relates to a method of doping a Raney nickel catalyst doped with metals by the incorporation of the doping metals in the form of a complex into the alkaline attack medium. Also disclosed is a process for the hydrogenation of nitriles to amines using said catalyst.Type: GrantFiled: September 24, 1996Date of Patent: November 24, 1998Assignee: Rhone-Poulenc ChimieInventors: Georges Cordier, Pierre Fouilloux, Nathalie Laurain
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Patent number: 5801286Abstract: The present invention relates to the field of the catalytic hydrogenation of nitrites to amines and, more particularly, of dinitriles such as adiponitrile (ADN) to diamines such as hexamethylenediamine (HMD).More precisely, the present invention relates to a process for the preparation of a catalyst for the hydrogenation of nitriles to amines of Raney nickel type doped with at least one additional metal element selected from columns IVb, Vb and VIb of the periodic classification.It is targeted at providing an economic and easy-to-implement process which makes it possible to obtain catalysts which are both active and selective with respect to nitrites and stable.The process is characterized in that it consists in suspending Raney nickel in a solution, preferably an acid solution, of the additional metal element.Type: GrantFiled: September 23, 1996Date of Patent: September 1, 1998Assignee: Rhone-Poulenc ChimieInventors: Michele Besson, Georges Cordier, Pierre Fouilloux, Jacqueline Masson
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Patent number: 5789621Abstract: A process for preparing an NH.sub.2 -containing compound by hydrogenating a compound containing at least one unsaturated carbon-nitrogen bond with hydrogen in the presence of a catalyst at temperatures not below room temperature and elevated hydrogen partial pressure in the presence or absence of a solvent which process includes the following steps:a) using a catalyst comprising a cobalt- and/or iron-containing catalyst, andb) after the conversion based on the compound to be hydrogenated and/or the selectivity based on the desired product has or have dropped below a defined value or the amount of an unwanted by-product has risen beyond a defined value, interrupting the hydrogenation by stopping the feed of the compound to be hydrogenated and of the solvent, if used,c) treating the catalyst at from 150.degree. to 400.degree. C. with hydrogen using a hydrogen pressure within the range from 0.Type: GrantFiled: August 8, 1996Date of Patent: August 4, 1998Assignee: BASF AktiengesellschaftInventors: Werner Schnurr, Guido Voit, Klemens Flick, Rolf-Hartmuth Fischer
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Patent number: 5763669Abstract: This invention relates to a process of preparing a ruthenium complex of the formula RuH.sub.2 (PR.sub.3).sub.2 L.sub.2 wherein PR.sub.3 is an organophosphorus ligand and L is H.sub.2 or PR.sub.3 ; a catalyst comprising at least one ruthenium complex having the formula RuH.sub.2 (PR.sub.3)L.sup.1.sub.3 wherein L.sup.1 is a neutral electron pair donor ligand; a process for preparing the catalyst and its use in situ in the hydrogenation of nitriles.Type: GrantFiled: June 21, 1996Date of Patent: June 9, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Richard Paul Beatty, Rocco Angelo Paciello
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Patent number: 5750788Abstract: A process is disclosed for preparing amines by hydrogenating compounds with at least 3 cyano groups prepared by adding acrylonitrile to ammonia or primary amines at temperatures from 80.degree. to 200.degree. C. and pressures from 5 to 500 bars.Type: GrantFiled: May 19, 1997Date of Patent: May 12, 1998Assignee: BASF AktiengesellschaftInventors: Lukas Haussling, Horst Neuhauser, Wolfgang Paulus
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Patent number: 5726334Abstract: This invention relates to a process for the preparation of ruthenium complexes of the formula RuH.sub.2 L.sub.2 (PR.sub.3).sub.2, wherein each L is independently H.sub.2 or an additional equivalent of PR.sub.3, and each R is independently H, a hydrocarbyl group, or an assembly of at least two hydrocarbyl groups connected by ether or amine linkages, comprising contacting a source of ruthenium and PR.sub.3 with gaseous hydrogen in the presence of a strong base, a phase-transfer catalyst, water and an organic solvent; and the use of certain classes of ruthenium complexes as catalysts in hydrogenation, and reductive hydrolysis processes.Type: GrantFiled: September 19, 1996Date of Patent: March 10, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Richard Paul Beatty, Rocco Angelo Paciello
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Patent number: 5717090Abstract: Caprolactam and hexamethylenediamine are prepared simultaneously starting from adiponitrile by a process in which(a) adiponitrile is partially hydrogenated to give a mixture containing essentially 6-aminocapronitrile, hexamethylenediamine, ammonia, adiponitrile and hexamethyleneimine,(b) the mixture obtained in (a) is subjected to a distillation to give ammonia as the top product and a bottom product I,(c) the bottom product I containing essentially 6-aminocapronitrile, hexamethylenediamine, adiponitrile, hexamethyleneimine, inert compound A and ammonia, the ammonia content being lower than that of the mixture used in stage (b), is subjected to a second distillation to give a mixture comprising the inert compound A and ammonia as the top product and a bottom product II,(d) the bottom product II is subjected, in a third column, to a distillation to give the inert compound A as the top product and a bottom product III,(e) the bottom product III is subjected, in a fourth column, to a distillation to give a top pType: GrantFiled: November 30, 1995Date of Patent: February 10, 1998Assignee: BASF AktiengesellschaftInventors: Peter Bassler, Hermann Luyken, Gunther Achhammer, Tom Witzel, Eberhard Fuchs, Rolf Fischer, Werner Schnurr
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Patent number: 5689003Abstract: The invention relates to a novel ruthenium complex having the formula Ru(.eta..sup.3 --C.sub.6 H.sub.8 --PCy.sub.2)(PCy.sub.3)Cl, wherein Cy is cyclohexyl; its use in the preparation of RuHCl(H.sub.2)(PCy.sub.3).sub.2 and RuH.sub.2 (H.sub.2).sub.2 (PCy.sub.3).sub.2 ; and the use of the complexes as catalysts in hydrogenation, imination and reductive hydrolysis processes.Type: GrantFiled: May 8, 1996Date of Patent: November 18, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard Paul Beatty, Rocco Angelo Paciello
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Patent number: 5629451Abstract: A process for selectively reducing nitrile contaminants in fluids such as water, methanol or hydrocarbon streams containing mono olefins and which contain minor amounts of contaminants comprising nitriles in the presence of hydrogen and a supported cobalt catalyst. In the olefin stream the nitrile contaminants are substantially reduced without substantial reduction of the mono olefins.Type: GrantFiled: June 30, 1994Date of Patent: May 13, 1997Assignee: Chemical Research & Licensing CompanyInventors: Dennis Hearn, Kyte H. Terhune
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Patent number: 5571943Abstract: This invention relates to a process for preparing primary amines by hydrogenation of mono and/or dinitrile with hydrogen in the presence of a nickel and/or cobalt catalyst on support and optionally in the presence of ammonia, this process being characterized in that a nickel and/or cobalt catalyst on support is used, optionally in combination with at least one solid, reaction medium-insoluble cocatalyst, the catalyst and/or the cocatalyst being substantially nonacid.Type: GrantFiled: March 28, 1995Date of Patent: November 5, 1996Assignee: Engelhard De Meern B.V.Inventors: Frederik Borninkhof, John W. Geus, Michiel J. F. M. Verhaak
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Patent number: 5557011Abstract: Process for the preparation of diamines of the general formula I ##STR1## in which A denotes a C.sub.1 -C.sub.20 alkylene chain optionally mono- to penta-substituted by C.sub.1 -C.sub.4 alkyl,R.sup.1, R.sup.2 denote C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 hydroxyalkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.20 alkylcycloalkyl, C.sub.4 -C.sub.20 cycloalkylalkyl, phenyl, C.sub.7 -C.sub.20 phenylalkyl, C.sub.1 -C.sub.20 alkoxyalkyl, C.sub.7 -C.sub.20 phenoxyalkyl or together a saturated or unsaturated C.sub.2 -C.sub.6 alkylene chain optionally monosubstituted, disubstituted, or trisubstituted by C.sub.1 -C.sub.4 alkyl and optionally interrupted by oxygen or nitrogen,by the reaction of dinitriles of the general formula IINC--A--CN (II),in which A has the aforementioned meaning,with secondary amines of the general formula II ##STR2## in which R.sup.1 and R.sup.2 have the aforementioned meanings, with hydrogen at temperatures ranging from 50.degree. to 200.degree. C.Type: GrantFiled: November 15, 1994Date of Patent: September 17, 1996Assignee: BASF AktiengesellschaftInventors: Tom Witzel, Eberhard Fuchs
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Patent number: 5268509Abstract: This invention relates to a process for the preparation of an iron catalyst used for the hydrogenation of organic compounds comprising partially oxidizing iron or an iron alloy in particulate form at an elevated temperature in the presence of gaseous oxygen until a weight gain of from 5% to 32% is obtained; and then reducing the partially oxidized iron or iron alloy at an elevated temperature in a stream of hydrogen.The invention also relates to a process for the preparation of primary amines comprising catalytically hydrogenating nitriles corresponding to said primary amines in the presence of an iron catalyst of the invention.Type: GrantFiled: June 11, 1990Date of Patent: December 7, 1993Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Dietrich Liebsch, Hans-H. Schwarz, Stephan Wendel, Peter Fischer
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Patent number: 5266731Abstract: Described are processes for producing amines from nitriles. The processes include electrocatalytic hydrogenations of nitriles in the presence of transition metal-oxide and/or transition metal-hydroxide cathodes to thereby form amines. Preferred modes of the invention provide highly advantageous processes for producing hexamethylenediamine from adiponitrile.Type: GrantFiled: July 17, 1991Date of Patent: November 30, 1993Assignee: Reilly IndustriesInventors: William M. Ayers, Mary H. Dean
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Patent number: 5105015Abstract: An improved process for selectively forming noncyclic, aliphatic polyamines from the corresponding aliphatic polynitriles by reacting the polynitrile with hydrogen at low temperature under a pressure of from 50 to 5,000 psi in a fixed bed reactor while continuously contacting the reactants with granular chromium and nickel promoted Raney.RTM. cobalt packed therein.Type: GrantFiled: June 4, 1991Date of Patent: April 14, 1992Assignee: W. R. Grace & Co.-Conn.Inventors: You-Jyh Lin, Stephen R. Schmidt, Ramin Abhari
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Patent number: 5097072Abstract: Polyamines are prepared via the batchwise hydrogenation of polynitriles by the gradual addition of the polynitrile into a fed-batch reactor which contains chromium promoted Raney.RTM. cobalt catalyst. The hydrogenation optionally is conducted in the presence of anhydrous ammonia. The polyamine product having amino groups which corresponds to the nitrile of the polynitrile is economically obtained in high selectivity and yield as the dominant product.Type: GrantFiled: March 21, 1991Date of Patent: March 17, 1992Assignee: W.R. Grace & Co.-Conn.Inventors: Gerald J. O'Neill, Albert H. Levesque
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Patent number: 4906783Abstract: Preparation of bis(hexamethylene)triamine from 6-aminohexanenitrile by catalytically preparing di(5-cyanopenyl)-amine, followed by hydrogenation using a nitride hydrogenation catalyst.Type: GrantFiled: February 25, 1988Date of Patent: March 6, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert A. Smiley
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Patent number: 4803304Abstract: Recovery of bis(hexamethylene)triamine from still heels of hexamethylenediamine by extraction using an aliphatic hydrocarbon having a boiling point between about 34.degree. C. and 210.degree. C.Type: GrantFiled: April 15, 1987Date of Patent: February 7, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert A. Smiley
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Patent number: 4739120Abstract: An improved process is disclosed for the catalytic hydrogenation of an organic nitrile group containing compound to a primary aminomethyl group in the presence of a rhodium catalyst, a basic substance, and in a two-phase solvent system comprising an immiscible organic solvent and water.Type: GrantFiled: August 21, 1986Date of Patent: April 19, 1988Assignee: The Dow Chemical CompanyInventor: Marie F. Zuckerman
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Patent number: 4601859Abstract: A dinitrile is hydrogenated to an omega-aminonitrile with hydrogen with a supported highly dispersed rhodium catalyst and only ammonia present. The catalyst is prepared by hydrolyzing a rhodium(III) halide or nitrate with strong aqueous base at elevated temperatures, drying the supported rhodium hydroxide at elevated temperatures and intimately contacting with hydrogen the dried product with hydrogen at 260.degree.-360.degree. C. High conversions, selectivity to aminonitrile and long catalyst service times and catalyst recyclability are achieved in the absence of an aprotic solvent.Type: GrantFiled: May 4, 1984Date of Patent: July 22, 1986Assignee: Allied CorporationInventors: James E. Galle, Frank Mares, Steven E. Diamond, Jeffrey Corsi, Francis J. Regina
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Patent number: 4598058Abstract: Molded catalyst materials contain metallic cobalt and/or nickel particles and a lubricant, the said particles being obtained by reduction of cobalt oxide and/or nickel oxide particles containing less than 0.1% by weight of alkali metal oxides and/or alkaline earth metal oxides at .ltoreq.500.degree. C., and the molded catalyst material having an indentation hardness greater than 300 kp/cm.sup.2.Type: GrantFiled: January 31, 1985Date of Patent: July 1, 1986Assignee: BASF AktiengesellschaftInventors: Gerhard Frank, Gerald Neubauer, Paul Duffner, Hans J. Wilfinger
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Patent number: 4595773Abstract: Copper-diamine complexes such as copper(II)-di-t-butylethylenediamine dibromide are prepared by the reaction of a dihalide such as 1,2-dibromoethane with an amine such as t-butylamine and a basic copper(II) compound such as cupric oxide in a nitrile solvent. The diamine can be liberated from the complex by reacting it with a complexing agent such as an ethylenediaminetetraacetic acid salt.Type: GrantFiled: January 24, 1985Date of Patent: June 17, 1986Assignee: General Electric CompanyInventor: Dwain M. White
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Patent number: 4587228Abstract: A molded iron catalyst material which has an indentation hardness of from 850 to 1500 kp/cm.sup.2 and contains metallic iron particles, obtained from iron oxide particles by contact with hydrogen at less than 500.degree. C., and a lubricant, its preparation and its use.Type: GrantFiled: January 25, 1985Date of Patent: May 6, 1986Assignee: BASF AktiengesellschaftInventors: Gerhard Frank, Gerald Neubauer
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Patent number: 4521527Abstract: Molded iron catalysts which contain metallic iron particles, obtained from anisometric iron oxide particles by contact with hydrogen at .ltoreq.500.degree. C., and a lubricant, are prepared.Type: GrantFiled: August 18, 1983Date of Patent: June 4, 1985Assignee: BASF AktiengesellschaftInventors: Gerhard Frank, Peter Rudolf, Gerald Neubauer, Manfred Ohlinger, Hans J. Wilfinger, Emil Pfannebecker, Paul Duffner
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Patent number: 4491673Abstract: This invention provides for the separation of the contents of the process discharge stream of reaction in which an amine is produced from a nitrile. An inorganic base having a concentration greater than 40 weight percent is introduced into the process discharge stream which is decanted, purged, flashed, and a portion thereof recycled.Type: GrantFiled: April 19, 1982Date of Patent: January 1, 1985Assignee: Monsanto CompanyInventors: Charles E. Cutchens, Marion J. Mathews, III, Mark S. Sowell, III
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Patent number: 4480051Abstract: Process for improving the activity of an iron oxide hydrogenation catalyst by reducing the catalyst; oxidizing the reduced catalyst and then re-reducing the catalyst.Type: GrantFiled: August 3, 1983Date of Patent: October 30, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: James C. Wu
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Patent number: 4429159Abstract: In the production of amines from nitriles where the nitriles are hydrogenated under pressure in the presence of a Raney Nickel Catalyst using hydrogen produced from methane and containing CO.sub.2, a more efficient separation of the product hexamethylene diamine from the catalyst is obtained by maintaining a specified carbonate concentration. This specific carbonate concentration improves the settling characteristics of the catalyst and reduces catalyst carryover into the crude hexamethylene diamine during decantation.Type: GrantFiled: March 18, 1983Date of Patent: January 31, 1984Assignee: Monsanto CompanyInventors: Charles E. Cutchens, Lynn H. Lanier
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Patent number: 4395573Abstract: In the production of hexamethylenediamine from adiponitrile an inorganic base is used to facilitate separation of Raney nickel catalyst and crude hexamethylenediamine.Type: GrantFiled: November 23, 1981Date of Patent: July 26, 1983Assignee: Monsanto CompanyInventors: Charles E. Cutchens, Marion J. Mathews, III, Mark S. Sowell, III
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Patent number: 4375003Abstract: An improved process for preparing primary amines from an aliphatic nitrile and hydrogen utilizing a Raney cobalt catalyst which contains from about 2 to 35 weight percent of aluminum on a 100 weight percent total weight basis. Preferably, this catalyst is prepared under low temperature conditions from a cobalt-aluminum alloy. The process can be practiced continuously for extended periods of time at high reaction rates and high conversion yields even when employing concentrated nitrile starting feeds.Type: GrantFiled: January 15, 1979Date of Patent: February 22, 1983Assignee: Nalco Chemical CompanyInventors: Ronald J. Allain, Gerald D. Smith
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Patent number: 4372893Abstract: Selective reduction of compounds containing reducible nitro-, nitroso-, nitrilo-, oximes or double bonds is effected by the use of a metal macrocyclic compound in prereduced form, such as a metal phthalocyanine or a metal porphyrin.Type: GrantFiled: October 6, 1980Date of Patent: February 8, 1983Inventor: Heiner Eckert
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Patent number: 4359585Abstract: This is an improvement in a process for the production of an amine such as hexamethylenediamine from a nitrile such as adiponitrile where the nitrile is hydrogenated under pressure in the presence of a Raney nickel catalyst, the reaction being conducted in a reactor from which is discharged a product stream containing both the amine and the Raney nickel catalyst. The improvement comprises charging to the process discharge stream containing the product amine and the Raney nickel catalyst, an inorganic base, whereby the Raney nickel catalyst is passivated and catalytic decomposition of the amine is substantially decreased.Type: GrantFiled: April 21, 1980Date of Patent: November 16, 1982Assignee: Monsanto CompanyInventors: Charles R. Campbell, Charles E. Cutchens
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Patent number: 4331557Abstract: A ruthenium-containing catalyst is regenerated after use for an organic chemical treatment, e.g., hydrogenation, dehydrogenation, isomerization, disproportionation, hydrocracking, etc., at an elevated temperature and at a considerably reduced pressure of the order of about 600 mm Hg and much lower of the order of about 0.001 mm Hg.Type: GrantFiled: May 22, 1980Date of Patent: May 25, 1982Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4311859Abstract: Unsaturated dinitriles are hydrogenated to saturated diamines using a rhodium catalyst on a silica support having a surface area larger than 275 m.sup.2 /g, a pore volume of from about 1.0 to 1.5 mL/g and an average pore size of from about 100 to about 175 A. The supported rhodium catalyst is prepared by a method which includes the steps of contacting a silica support having the characteristics described above with a solution or dispersion of rhodium or a reducible compound of rhodium, and then subjecting the impregnated silica support to vacuum treatment.Type: GrantFiled: December 5, 1980Date of Patent: January 19, 1982Assignee: Phillips Petroleum CompanyInventors: Timothy P. Murtha, Charles A. Drake
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Patent number: 4288626Abstract: A process for prolonging the activity of catalysts during the hydrogenation of unsaturated dinitriles comprising pretreating the dinitrile feed with a crystalline zeolite.Type: GrantFiled: September 5, 1980Date of Patent: September 8, 1981Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4275237Abstract: Heavy reaction product after separation as by distillation of light reaction product or diadduct from a reaction mixture obtained by reaction of olefinically unsaturated nitriles with monoolefinic hydrocarbons containing an allylic hydrogen atom is hydrogenated to produce a polyamine mixture useful as an epoxy resin hardener yielding cured resins exhibiting low water absorption.Type: GrantFiled: August 6, 1979Date of Patent: June 23, 1981Assignee: Philips Petroleum CompanyInventors: Charles A. Drake, Ralph P. Williams
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Patent number: 4247481Abstract: This is an improvement in a process for the production of an amine such as hexamethylenediamine from a nitrile such as adiponitrile where the nitrile is hydrogenated under pressure in the presence of a Raney nickel catalyst, the reaction being conducted in a reactor from which is discharged a product stream containing both the amine and the Raney nickel catalyst. The improvement comprises charging to the process discharge stream containing the product amine and the Raney nickel catalyst, a nitroaromatic compound, whereby the Raney nickel catalyst is passivated and catalytic decomposition of the amine is substantially decreased.Type: GrantFiled: December 26, 1979Date of Patent: January 27, 1981Assignee: Monsanto CompanyInventors: Charles R. Campbell, Charles E. Cutchens