Of Cyano Patents (Class 564/490)
-
Publication number: 20100099872Abstract: The invention relates to a process for preparing an ethylene amine mixture, which comprises hydrogenating an amino nitrile mixture comprising at least two ?-amino nitriles in an amount of at least 5% by weight in each case in the presence of a catalyst and, if appropriate, a solvent.Type: ApplicationFiled: February 27, 2008Publication date: April 22, 2010Applicant: BASF SEInventors: Kirsten Dahmen, Alfred Oftring, Katrin Baumann, Randolf Hugo, Thilo Hahn, Johann-Peter Melder
-
Publication number: 20100094057Abstract: The invention relates to a process for preparing ethylenediamine by hydrogenation of aminoacetonitrile over a catalyst, wherein the hydrogenation is carried out in a solution comprising aminoacetonitrile, water in a proportion of from 0 to 60% by weight and a solvent and the aminoacetonitrile comprised in the solution is fed into the reaction vessel at a rate which is not greater than the rate at which the aminoacetonitrile reacts with hydrogen in the hydrogenation.Type: ApplicationFiled: February 28, 2008Publication date: April 15, 2010Applicant: BASF SEInventors: Alfred Oftring, Kirsten Dahmen, Randolf Hugo, Thilo Hahn, Katrin Baumann, Johann-Peter Melder
-
Publication number: 20100056828Abstract: The invention relates to a process for preparing an ethylene amine mixture, which comprises hydrogenating an amino nitrile mixture comprising at least 30% by weight of aminoacetonitrile (AAN) and at least 5% by weight of iminodiacetonitrile (IDAN) in the presence of a catalyst. Ethylenediamine (EDA) and/or diethylenetriamine (DETA) and, if appropriate, further ethylene amines can be isolated from the ethylene amine mixtures obtained.Type: ApplicationFiled: February 28, 2008Publication date: March 4, 2010Applicant: BASF SEInventors: Alfred Oftring, Kirsten Dahmen, Thilo Hahn, Randolf Hugo, Katrin Baumann, Johann-Peter Melder
-
Publication number: 20100029991Abstract: The invention relates to a process for preparing triethylenetetramine (TETA), which comprises hydrogenating ethylenediaminediacetonitrile (EDDN) in the presence of a catalyst and a solvent.Type: ApplicationFiled: February 27, 2008Publication date: February 4, 2010Applicant: BASF SEInventors: Kirsten Dahmen, Alfred Oftring, Randolf Hugo, Katrin Baumann, Thilo Hahn, Johann-Peter Melder
-
Publication number: 20090069590Abstract: The present invention relates to a process for preparing an aminoalkyl nitrile by reaction of a corresponding monoamine with a corresponding alkenyl nitrile in a continuous mode of operation, which comprises the steps (a) introduction of the corresponding monoamine into a continuously conveyed reaction stream; (b) introduction of the corresponding alkenyl nitrite into the reaction stream, with this already comprising the aminoalkyl nitrile on addition; (c) reaction of the reaction stream in a first reaction region; and (d) at least partial transfer of the reaction stream into at least one second reaction region for further reaction. The invention further relates to a process for preparing a diamine from the aminoalkyl nitrile, suitable apparatuses for carrying out the processes and their corresponding use.Type: ApplicationFiled: May 7, 2007Publication date: March 12, 2009Applicant: BASF AktiengesellschaftInventors: Jan Eberhardt, Thilo Hahn, Johann-Peter Melder, Gerhard Fritz, Volkmar Menger, Thomas Hill
-
Publication number: 20080293973Abstract: The present invention relates to a process for the industrial preparation of a diamine starting from a corresponding alkenyl nitrile comprising at least one C-C double bond, which comprises the steps (a) reaction of the alkenyl nitrile with a corresponding monoamine in a first reactor so that the monoamine adds exothermically onto the at least one double bond to form an aminoalkyl nitrile, with the monoamine and water being charged initially and the alkenyl nitrile being fed in; (b) evaporation of unreacted alkenyl nitrile and monoamine to increase the concentration of the aminoalkyl nitrile product in the bottoms of the first reactor; (c) transfer of the aminoalkyl nitrile bottom product from step (b) to a second reactor; (d) batchwise catalytic hydrogenation of the aminoalkyl nitrile transferred in step (c) to the diamine in the second reactor, with each batch being obtained by initially charging a catalyst suitable for the hydrogenation of nitriles to amines and also water, the desired diamine and a basType: ApplicationFiled: October 31, 2006Publication date: November 27, 2008Applicant: BASF SEInventors: Martin Ernst, Steffen Oehlenschlager, Frank Kuhnke, Karl-Heinz Ross, Roland Deeg, Johann-Peter Melder
-
Patent number: 7453012Abstract: A process for the hydrogenation of compounds comprising nitrile or nitro functional groups to amine, aminonitrile or aminonitro compounds is provided. The process can be a continuous process conducted in the presence of a heterogeneous hydrogenation catalyst in divided form and a basic compound. The reaction can be conducted in a stirred reactor comprising an external loop for circulating the reaction mixture, allowing one portion of the hydrogenated products to be separated without withdrawing the catalyst, by using tangential filtration. The process may be especially useful in the hydrogenation of adiponitrile to an aminocapronitrile/hexamethylenediamine mixture.Type: GrantFiled: January 20, 2003Date of Patent: November 18, 2008Assignee: Rhodia Polyamide IntermediatesInventors: Gérald Bocquenet, André Chesnais, Jean-Michel Desire, Philippe Leconte, Lionel Sever
-
Publication number: 20080275145Abstract: A catalyst including cobalt, zinc oxide and aluminium is described, having a total cobalt content of 15-75% by weight (on reduced catalyst), an aluminium content ?10% by weight (based on ZnO) and which when reduced at 425° C., has a cobalt surface area as measured by hydrogen chemisorption at 150° C. of at least 20 m2/g cobalt. A method for preparing the catalyst is also described including combining a solution of cobalt, zinc and aluminium with an alkaline solution to effect co-precipitation of a cobalt-zinc-aluminium composition from the combined solutions, separating of the co-precipitated composition form the combined solutions, heating the composition to form an oxide composition, and optionally reducing at least a portion of the cobalt to cobalt metal. The catalysts may be used for hydrogenation reactions and for the Fischer-Tropsch synthesis of hydrocarbons.Type: ApplicationFiled: April 15, 2005Publication date: November 6, 2008Inventors: John Leonello Casci, Carl Leonard Huitson, Cornelis Martinus Lok
-
Patent number: 7399886Abstract: This invention relates to an improved hydrogenation process for the preparation of etheramines. In the process, cyanoethylated alcohols, i.e., the reaction product of an alcohol with (meth)acrylonitrile, are contacted with hydrogen in the presence of a sponge cobalt catalyst. The improvement in the process resides in effecting the hydrogenation process utilizing a cyanoethylated alcohol feedstock contaminated with byproduct acrylonitrile and utilizing a solvent that solubilizes byproduct (meth)acrylonitrile present in the feedstock. Specific classes of solvents employed are ethers and amides.Type: GrantFiled: September 4, 2003Date of Patent: July 15, 2008Inventors: Garnini Ananda Vedage, Eugene George Lutz, Matthew J. Engel
-
Patent number: 7381845Abstract: A process for hydrogenating nitrile functions present in organic compounds over at least one heterogeneous catalyst, in which the hydrogenation is carried out in the presence of an ionic liquid, is described.Type: GrantFiled: December 20, 2004Date of Patent: June 3, 2008Assignee: BASF AktiengesellschaftInventors: Verena Weiskopf, Till Gerlach, Kirsten Wenz
-
Publication number: 20080039658Abstract: A method of producing a primary amine by the hydrogenation of a nitrile in the presence of a hydrogenation catalyst. The hydrogenation catalyst contains at least one metal selected from the group consisting of nickel, cobalt and iron. Before use in the hydrogenation of nitrile, the hydrogenation catalyst is pretreated with at least one treating agent selected from the group consisting of hydrocarbons, alcohols, ethers, esters and carbon monoxide at 150 to 500° C.Type: ApplicationFiled: August 9, 2007Publication date: February 14, 2008Inventors: KAZUHIKO AMAKAWA, Yoshiaki Yamamoto
-
Patent number: 7291754Abstract: Process for the catalytic hydrogenation of a nitrite in the presence of an amine and a catalyst wherein the catalyst is a liquid-rinsed Raney-type catalyst contacted with a hydroxide prior to contacting the catalyst with the amine. The process results in higher selectivity in the formation of diamines from diniriles.Type: GrantFiled: January 21, 2004Date of Patent: November 6, 2007Assignee: DSM IP Assets B.V.Inventors: Franciscus H. A. M. Vandenbooren, Hubertus J. M. Bosman, Alexander V. Peters, Maria J. G. Van Den Boer
-
Patent number: 7259274Abstract: An aliphatic nitrile is prepared by a process of reacting an aliphatic carboxylic acid, an aliphatic dicarboxylic acid or an alkyl ester thereof, wherein the alkyl group has 1 to 5 carbon atoms, with ammonia in the presence of a catalyst of titanium oxide supported on solid silica.Type: GrantFiled: September 9, 2004Date of Patent: August 21, 2007Assignee: Kao CorporationInventors: Michio Terasaka, Tetsuaki Fukushima
-
Patent number: 7208448Abstract: The invention relates to a passivated hydrogenation catalyst that is embedded in a primary amine, a derivative thereof, and/or a nitrile, the process to make such catalysts, as well as the use of such catalysts in a hydrogenation process in which an amine or a derivative thereof is produced.Type: GrantFiled: March 13, 2003Date of Patent: April 24, 2007Assignee: Akzo Nobel N.V.Inventors: Thale Jacob Ottens, Jacobus Van Den Berg, Paul Van Poecke
-
Patent number: 7196223Abstract: A nitrile-containing mixture, which includes a nitrile dissolved in a higher alcohol solvent, and hydrogen are fed to a reactor containing a catalyst. An amine is produced by hydrogenating the nitrile that is dissolved in the higher alcohol solvent. In a preferred embodiment, the reactor also contains a caustic solution. The preferred nitrile-containing mixture includes octadecaneditrile (ODDN) and hexanol to produce a preferred octadecanediamine (ODDA) through hydrogenation.Type: GrantFiled: May 3, 2005Date of Patent: March 27, 2007Assignee: Solutia, Inc.Inventors: Tom L. Flowers, Anthony K. Uriarte, Shannon Davis, Gregory J. Ward
-
Patent number: 7122702Abstract: Process for the catalytic hydrogenation of an aliphatically unsaturated group in an organic compound in the presence of a catalyst whose preparation has involved precipitation of catalytically active components onto monoclinic, tetragonal or cubic zirconium dioxide.Type: GrantFiled: December 10, 2003Date of Patent: October 17, 2006Assignee: BASF AktiengesellschaftInventors: Till Gerlach, Frank Funke, Johann-Peter Melder
-
Patent number: 7115781Abstract: An oxidic composition which is suitable as a catalyst having divalent and trivalent iron in an atomic ratio of divalent to trivalent iron in the range from greater than 0.5 to 5.5 and oxygen as a counterion to the divalent and trivalent iron. The catalyst composition is useful in the hydrogenation of nitriles to amines.Type: GrantFiled: October 18, 2002Date of Patent: October 3, 2006Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch, Peter Bassler, Rolf-Hartmuth Fischer, Stefan Maixner, Johann-Peter Melder, Hermann Luyken
-
Patent number: 7056485Abstract: The invention is directed to a continuous hydrogenation process in which a hydrogenable compound is dissolved in a working solution with hydrogen and a heterogeneous catalyst. At least part of the hydrogen-containing waste hydrogenation gas generated in the reaction is compressed and then recycled into the hydrogenation reactor. A jet pump is used for the compression of the waste hydrogenation gas and a liquid or gaseous feedstock of the hydrogenation process is used as the motive agent. Preferred motive agents are the hydrogenation gas or a working solution recycled into the process. The process is particularly suitable for performing the hydrogenation step in the anthraquinone process for the production of hydrogen peroxide.Type: GrantFiled: October 14, 2003Date of Patent: June 6, 2006Assignee: Degussa AGInventors: Matthias Creutz, Hubertus Eickhoff, Bernhard Maurer
-
Patent number: 6984759Abstract: Process for the perfluoropolyether preparation having reactive end groups —CH2NH2, —CHO, —CH2OH, by reduction of the corresponding perfluoropolyethers having —CN, —COCl, —CHO end groups by using gaseous hydrogen in the presence of a catalyst constituted by Pd, Rh, or Ru, supported on solid metal fluorides, at a temperature from 20° C. to 150° C. and under a pressure between 1 and 50 atm.Type: GrantFiled: July 31, 2003Date of Patent: January 10, 2006Assignee: Solvay Solexis S.p.A.Inventors: Antonella Di Meo, Rosaldo Picozzi, Claudio Tonelli
-
Patent number: 6951959Abstract: An improved process for the production of 3-dimethylaminopropylamine in high purity from N,N-dimethylaminopropionitrile utilizing a low pressure hydrogenation process is described. The basic process comprises contacting the nitrile with hydrogen at low pressure in the presence of a catalyst under conditions sufficient to effect the conversion of the nitrile to the primary amine product.Type: GrantFiled: December 9, 2003Date of Patent: October 4, 2005Assignee: Solutia Inc.Inventors: Gregory J. Ward, Bryan C. Blanchard
-
Patent number: 6916457Abstract: A non-chrome, copper-containing catalyst, Cu—Al—O and method of preparing the same are provided wherein the Cu—Al—O catalyst is prepared by the co-precipitation of copper nitrate (Cu(NO3)2) and sodium aluminate (Na2Al2O4) solutions using sodium carbonate (Na2CO3) as a precipitant. The precipitate is filtered, washed to removed excess sodium, and dried. The dried product, to be used in a powder form, is calcined at a preferred temperature of approximately 700° to 900° C. for approximately 1 to 4 hours. The dry powder, to be tableted or extruded, is calcined at a temperature of approximately 400° to 700° C. The activity of the Cu—Al—O catalyst can be promoted in hydrogenolysis applications by the addition of various agents. The Cu—Al—O catalyst can be employed in applications in place of Cu/Cr, or other copper based catalysts.Type: GrantFiled: July 16, 2002Date of Patent: July 12, 2005Assignee: Engelhard CorporationInventor: Jianping Chen
-
Patent number: 6794542Abstract: Process for the preparation of a diasteromerically enriched phenylglycine amide derivative in which an enantiomerically enriched phenylglycine amide is converted into the corresponding Schiff base with the aid of compound R2—C(O)—R3, and the Schiff base obtained is subsequently converted into the diastereomerically enriched phenyglycine amide derivative with the aid of a cyanide source, a reducing agent or an allyl organometallic compound. The phenylglycine amide derivatives obtained are interesting starting materials for the preparation of for example enantiomerically enriched &agr;- and or &bgr;-amino acids and derivatives thereof, such as amides and esters, and amines.Type: GrantFiled: October 9, 2002Date of Patent: September 21, 2004Assignee: DSM N.V.Inventors: Wilhelmus Hubertus Joseph Boesten, Harold Monro Moody, Bernardus Kaptein, Johannes Paulus Gerardus Seerden, Marcelles Van Der Sluis, Ben Lange De, Quirinus Bernardus Broxterman
-
Patent number: 6790995Abstract: Mixtures of primary amines of the formula (I) X—CH2—NH2 (I) and secondary amines of the formula (II) (X—CH2—)2NH (II) where X is C1-20-alkyl, C2-20-alkenyl or C3-8-cycloalkyl which may be unsubstituted or substituted by C1-20-alkyl, C3-8-cycloalkyl, C4-20-alkylcycloalkyl, C4-20-cycloalkylalkyl, C2-20-alkoxyalkyl, C6-14-aryl, C7-20-alkylaryl, C7-20-aralkyl, C1-20-alkoxy, hydroxy, C1-20-hydroxyalkyl, amino, C1-20-alkylamino, C2-20-dialkylamino, C2-12-alkenylamino. C3-8-cycloalkylamino, arylamino, diarylamino, aryl-C1-8-alkylamino, halogen, mercapto, C2-20-alkenyloxy, C3-8-cycloalkoxy, aryloxy and/or C2-8-alkoxycarbonyl are prepared by reacting nitriles of the formula (III) X—CN (III) with hydrogen at from 50 to 250° C. and pressures of from 5 to 350 bar in the presence of a Pd-containing catalyst comprising, based on the total weight of the catalyst, from 0.1 to 10% by weight of Pd on a support.Type: GrantFiled: January 3, 2002Date of Patent: September 14, 2004Assignee: BASF AktiengesellschaftInventors: Joachim Pfeffinger, Michael Hüllmann, Arthur Höhn, Frank Funke, Frank Ohlbach, Till Gerlach
-
Patent number: 6790994Abstract: The present invention relates to a process for the hydrogenation of nitrile functional groups to amine functional groups. It relates more particularly to a process for the complete or partial hydrogenation of dinitrile compounds to diamine or aminonitrile compounds. The invention relates to a process for the hydrogenation of nitrile functional groups to amine functional groups using hydrogen in the presence of a hydrogenation catalyst and of a strong inorganic base preferably deriving from an alkali metal or alkaline earth metal. According to the invention, the process comprises a stage of conditioning the catalyst which consists in mixing the hydrogenation catalyst, a predetermined amount of strong inorganic base and a solvent in which the strong inorganic base is not very soluble. This solvent is an amine compound, such as hexamethylenediamine in the case of the hydrogenation of adiponitrile to HMD and/or aminocapronitrile.Type: GrantFiled: January 10, 2003Date of Patent: September 14, 2004Assignee: Rhodia Polyamide IntermediatesInventors: Vincent Boschat, Philippe Leconte
-
Publication number: 20040015017Abstract: A process for the hydrogenation, using molecular hydrogen (H2), of a catalytic system, wherein the catalytic system comprises a base and a complex of formula; (II) wherein Y represents simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, and N2P2 is a tetradentate diimine-diphosphino ligand.Type: ApplicationFiled: April 25, 2003Publication date: January 22, 2004Inventors: Valentin Rautenstrauch, Raphael Churlaud, Robert Harold Morris, Kamaluddin Abdur-Rashid
-
Patent number: 6677486Abstract: Nitriles are hydrogenated to primary amines over an activated, alpha-Al2O3-containing, macroporous Raney catalyst based on an alloy of aluminum and at least one transition metal selected from the group consisting of iron, cobalt and nickel, and, if desired, one or more further transition metals selected from the group consisting of titanium, zirconium, chromium and manganese, which is obtainable by a process comprising the steps in the order (a)-(f): (a) preparing a kneadable composition comprising the alloy, a shaping aid, water and a pore former; (b) shaping the kneadable composition to form a shaped body; (c) calcining the shaped body; (d) activating the calcined shaped body by treatment with aqueous alkali metal hydroxide solution; (e) rinsing the shaped catalyst body with aqueous alkali metal hydroxide solution; (f) rinsing the shaped catalyst body with water.Type: GrantFiled: November 7, 2001Date of Patent: January 13, 2004Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
-
Patent number: 6660887Abstract: An improved process for the production of 3-dimethylaminopropylamine in high (>99%) purity from N,N-dimethylaminopropionitrile utilizing a low pressure hydrogenation process is described. The basic process comprises contacting the nitrile with hydrogen at low pressure in the presence of a sponge nickel catalyst under conditions sufficient to effect the conversion of the nitrile to the primary amine product. The improvement in the process resides in a combination of carrying out the hydrogenation process at low pressures and temperatures in the presence of a catalytic amount of caustic base in order to give an improved selectivity of greater than 99.60% of DMAPN to DMAPA.Type: GrantFiled: December 23, 2002Date of Patent: December 9, 2003Assignee: Solutia Inc.Inventors: Gregory J. Ward, Bryan C. Blanchard
-
Publication number: 20030144552Abstract: The present invention relates to a process for the hydrogenation of nitrile functional groups to amine functional groups. It relates more particularly to a process for the complete or partial hydrogenation of dinitrile compounds to diamine or aminonitrile compounds.Type: ApplicationFiled: January 10, 2003Publication date: July 31, 2003Inventors: Vincent Boschat, Philippe Leconte
-
Patent number: 6600075Abstract: Disclosed is a method for preparing tertiary amine compounds from primary amines and nitrites in the presence of hydrogen gas and a metal catalyst, or metal-containing catalyst composition, at a temperature from about 50° C. to about 200° C. and at a pressure from about 100 psig to 1500 psig. The primary amines and the nitriles used in the process may be diamines and/or dinitriles, or may be combinations of primary amines and/or nitrites. Also disclosed are novel tertiary amine compounds made by the described method.Type: GrantFiled: November 13, 2001Date of Patent: July 29, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Kelley Moran Whittle, Alan Martin Allgeier, Thomas Papin Gannett, David Page Higley
-
Patent number: 6525223Abstract: Secondary amines of the formula (II) (X—CH2—)2NH (II) where X is a C1-20-alkyl, C2-20-alkenyl or C3-8-cycloalkyl group which may be unsubstituted or substituted by C1-20-alkyl, C3-8-cycloalkyl, C4-20-alkylcycloalkyl, C4-20-cycoalkylalkyl, C2-20-alkoxyalkyl, C6-14-aryl, C7-20-alkylaryl, C7-20-aralkyl, C1-20-alkoxy, hydroxy, C1-20-hydroxyalkyl, amino, C1-20-alkylamino, C2-20-dialkylamino, C2-12-alkenylamino, C3-8-cycloalkylamino, arylamino, diarylamino, aryl-C1-8-alkylamino, halogen, mercapto, C2-20-alkenyloxy, C3-8-cycloalkoxy, aryloxy and/or C2-8-alkoxycarbonyl, are prepared by reacting nitriles of the formula (III) X—CN (III) with hydrogen at from 20 to 250° C. and pressures of from 60 to 350 bar in the presence of an Rh-containing catalyst comprising from 0.Type: GrantFiled: December 27, 2001Date of Patent: February 25, 2003Assignee: BASF AktiengesellschaftInventors: Joachim Pfeffinger, Michael Hüllmann, Arthur Höhn, Frank Funke, Frank Ohlbach, Till Gerlach
-
Patent number: 6521564Abstract: A process for the modification of a hydrogenation catalyst of the Raney nickel, Raney cobalt, nickel-on-carrier or cobalt-on-carrier type, which process includes treating the hydrogenation catalyst at temperatures of about 0° C. to about 120° C. with carbon monoxide, carbon dioxide, formaldehyde, a lower aliphatic aldehyde, an aromatic aldehyde, an aliphatic ketone, an aromatic ketone, a mixed aliphatic/aromatic ketone, glyoxal, pyruvaldehyde or glyoxylic acid as the modification agent in a liquid dispersion medium consisting of water or an organic solvent for a duration of about 15 minutes to about 24 hours. When the thus-modified catalyst is used in the hydrogenation of a nitrile to the corresponding amine, the selectivity is increased, and significantly favors the amount of the primary amine vis-à-vis the undesired secondary amine in the hydrogenation product as compared to when the corresponding unmodified catalyst is employed.Type: GrantFiled: November 30, 2000Date of Patent: February 18, 2003Assignee: Roche Vitamins, Inc.Inventors: Oliver Gerald Degischer, Felix Roessler
-
Publication number: 20020173676Abstract: A method for producing amines by catalytic hydrogenation of nitrites or imines with hydrogen-containing gases in the presence of a molded hydrogenation catalyst of Raney type, where the Raney catalyst is in the form of hollow bodies.Type: ApplicationFiled: December 21, 2001Publication date: November 21, 2002Inventors: Daniel Ostgard, Monika Berweiler, Stefan Roder
-
Patent number: 6476270Abstract: A method for preparation of an amine from a carbonium ion precursor and a nitrile. The method comprises the steps of: (a) contacting the carbonium ion precursor and the nitrile with aqueous ammonium hydrogen sulfate to produce an amide; and (b) hydrolyzing the amide to the amine. Optionally, the ammonium hydrogen sulfate, nitrile and ammonia are recovered and recycled.Type: GrantFiled: November 14, 2001Date of Patent: November 5, 2002Assignee: Rohm and Haas CompanyInventor: Newman Mayer Bortnick
-
Publication number: 20020128513Abstract: Secondary amines of the formula (II)Type: ApplicationFiled: December 27, 2001Publication date: September 12, 2002Inventors: Joachim Pfeffinger, Michael Hullmann, Arthur Hohn, Frank Funke, Frank Ohlbach, Till Gerlach
-
Publication number: 20020077505Abstract: A method for preparation of an amine from a carbonium ion precursor and a nitrile. The method comprises the steps of: (a) contacting the carbonium ion precursor and the nitrile with aqueous ammonium hydrogen sulfate to produce an amide; and (b) hydrolyzing the amide to the amine. Optionally, the ammonium hydrogen sulfate, nitrile and ammonia are recovered and recycled.Type: ApplicationFiled: November 14, 2001Publication date: June 20, 2002Inventor: Newman Mayer Bortnick
-
Patent number: 6399830Abstract: This invention pertains to an improvement in a process for the formation of secondary or tertiary amines by the catalytic reductive amination of a nitrile with a primary amine. The catalyst employed in the improved reductive amination process is one that has been promoted with an acidic promoter preferably a solid phase acidic promoter.Type: GrantFiled: December 13, 2000Date of Patent: June 4, 2002Assignee: Air Products and Chemicals, Inc.Inventors: John Nelson Armor, Michael Edward Ford, William Eamon Carroll
-
Publication number: 20020058841Abstract: Nitriles are hydrogenated to primary amines over an activated, alpha-Al2O3-containing, macroporous Raney catalyst based on an alloy of aluminum and at least one transition metal selected from the group consisting of iron, cobalt and nickel, and, if desired, one or more further transition metals selected from the group consisting of titanium, zirconium, chromium and manganese, which is obtainable by a process comprising the steps in the order (a)-(f):Type: ApplicationFiled: November 7, 2001Publication date: May 16, 2002Inventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
-
Publication number: 20020058842Abstract: In a process for the continuous hydrogenation of nitrites to primary amines in the liquid phase over a suspended, activated Raney catalyst based on an alloy of aluminum and at least one transition metal selected from the group consisting of iron, cobalt and nickel, and, if desired, one or more further transition metals selected from the group consisting of titanium, zirconium, chromium and manganese, the hydrogenation is carried out in the absence of ammonia and basic alkali metal compounds or alkaline earth metal compounds.Type: ApplicationFiled: November 14, 2001Publication date: May 16, 2002Inventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
-
Patent number: 6384263Abstract: The present invention provides a process for making 3-hydroxyalkanenitriles comprising the steps of reacting an alkenylnitrile, wherein the alkenylnitrile is an alkenyl-2-nitrile or an alkenylnitrile which under reaction conditions isomerizes to form an alkenyl-2-nitrile, in the presence of a base with benzyl alcohol to form a 3-benzyloxyalkanenitrile adduct and then partially hydrogenating the adduct in the presence of a trace amount of HCl to form the 3-hydroxyalkanenitrile or fully hydrogenating the adduct to form a 3-hydroxyaminoalkane.Type: GrantFiled: July 27, 2001Date of Patent: May 7, 2002Assignee: E. I. du Pont de Nemours and CompanyInventor: Frank E. Herkes
-
Patent number: 6380420Abstract: A process for preparing fatty amines by the cross-metathesis of normal alpha olefins and acrylonitrile to form an intermediate fatty acid nitrile which is hydrogenated to the corresponding fatty amine.Type: GrantFiled: September 8, 2000Date of Patent: April 30, 2002Assignee: Chevron U.S.A. Inc.Inventors: William L. Schinski, Michael S. Driver
-
Patent number: 6331651Abstract: A process for making HMD in which a butadiene hydrocyantion reaction product that contains phosphorous-containing impurities is treated with ozone.Type: GrantFiled: April 20, 2001Date of Patent: December 18, 2001Assignee: E. I. du Pont de Nemours and CompanyInventor: John Joseph Ostermaier
-
Publication number: 20010004672Abstract: A process for the modification of a hydrogenation catalyst of the Raney nickel, Raney cobalt, nickel-on-carrier or cobalt-on-carrier type, which process includes treating the hydrogenation catalyst at temperatures of about 0° C. to about 120° C. with carbon monoxide, carbon dioxide, formaldehyde, a lower aliphatic aldehyde, an aromatic aldehyde, an aliphatic ketone, an aromatic ketone, a mixed aliphatic/aromatic ketone, glyoxal, pyruvaldehyde or glyoxylic acid as the modification agent in a liquid dispersion medium consisting of water or an organic solvent for a duration of about 15 minutes to about 24 hours. When the thus-modified catalyst is used in the hydrogenation of a nitrile to the corresponding amine, the selectivity is increased, and significantly favors the amount of the primary amine vis-à-vis the undesired secondary amine in the hydrogenation product as compared to when the corresponding unmodified catalyst is employed.Type: ApplicationFiled: November 30, 2000Publication date: June 21, 2001Inventors: Oliver Gerald Degischer, Felix Roessler
-
Patent number: 6248925Abstract: This invention pertains to an improvement in a process for the formation of secondary or tertiary amines by the catalytic reductive amination of a nitrile with a primary or secondary amine and, particularly to the reductive amination of C8-20 nitrites with a secondary amine. The catalyst employed in the improved reductive amination process is one which has been promoted with a lithium salt or base, e.g., lithium chloride or lithium hydroxide.Type: GrantFiled: October 22, 1999Date of Patent: June 19, 2001Assignee: Air Products and Chemicals, Inc.Inventors: Michael Edward Ford, John Nelson Armor
-
Patent number: 6080891Abstract: The present invention provides a process for preparing a high-quality aliphatic nitrile in a high yield at a low cost without the dissolution of a catalyst in the product, which comprises reacting an aliphatic carboxylic acid, a lower alkyl ester thereof or a fatty acid glyceride with ammonia in the presence of a solid catalyst which exhibits a high activity even at a reaction temperature of as low as 300.degree. C. or below and is difficultly soluble in the reaction fluid; and a process for the preparation of amines by hydrogenating the aliphatic nitrile prepared by the above process. Namely, the present invention provides a process for the preparation of an aliphatic nitrile by reacting an aliphatic carboxylic acid, a lower alkyl ester thereof or a fatty acid glyceride with ammonia in the presence of a composite oxide catalyst comprising titanium oxide as the main component; and a process for the preparation of amines by hydrogenating the aliphatic nitrile prepared by the above process.Type: GrantFiled: August 20, 1999Date of Patent: June 27, 2000Assignee: Kao CorporationInventors: Michio Terasaka, Yasuyuki Mimura, Hiroshi Abe
-
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
-
Patent number: 5948942Abstract: A catalyst useful for the simultaneous and selective hydrogenation of diolefins and nitriles present in a hydrocarbon feedstock includes (a) a support material selected from the group consisting of inorganic oxide, carbon, zeolite and mixtures thereof; and (b) a catalytically active metal phase including at least two metals selected from the group consisting of at least partially reduced Group IB metals and completely reduced Group VIII metals, the active metal phase being present in an amount of about .gtoreq.0.03 wt %.Type: GrantFiled: September 19, 1997Date of Patent: September 7, 1999Assignee: Intevep, S.A.Inventors: Magdalena Ramirez de Agudelo, Djamal Djauadi, Julia Guerra
-
Patent number: 5898085Abstract: A process for the hydrogenation of 3-aminopentanenitrile to produce 1,3 diaminopentane using a Raney.RTM. cobalt catalyst promoted with chromium, nickel, molybdenum, iron, manganese or mixtures thereof. Performing the reaction in the presence of aqueous caustic (e.g., alkali metal hydroxide) enhances the selectivity to 1,3 diaminopentane.Type: GrantFiled: March 26, 1998Date of Patent: April 27, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Frank Edward Herkes, Jay Leslie Snyder
-
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
-
Patent number: 5886227Abstract: Disclosed is an improved process for the catalytic hydrogenation of cyanopropionaldehyde alkyl acetals (CPAA) to form the aminobutyraldehyde alkyl acetals. The basic process comprises hydrogenating the cyanopropionaldehyde alkyl acetals by contacting said cyanopropionaldehyde alkyl acetals with hydrogen in the presence of a nickel or cobalt catalyst under conditions for reducing the nitrile group to the primary amine. The improvement resides in effecting the hydrogenation of a cyanopropionitrile dialkyl acetal feedstock containing contaminating levels of cyanopropionaldehyde in the presence of a secondary alkanol or water.Type: GrantFiled: October 28, 1997Date of Patent: March 23, 1999Assignee: Air Products and Chemicals, Inc.Inventors: Gamini Ananda Vedage, Kathryn Sue Hayes
-
Patent number: 5877364Abstract: A process is provided for simultaneous selective hydrogenation of diolefins and nitriles from a hydrocarbon feedstock, wherein hydrogenation is carried out using a catalyst in one reactor zone while partially deactivated catalyst in another reactor zone is regenerated.Type: GrantFiled: September 19, 1997Date of Patent: March 2, 1999Assignee: Intevep, S.A.Inventors: Zaida Hernandez, Wolfgang Garcia, Magdalena Ramirez de Agudelo