Preparing A Primary Monoamine Patents (Class 564/493)
  • Publication number: 20140048455
    Abstract: Compounds of the formulae: RO—X—NH2 (Ia); RO—X—NH3+Y? (Ib); RO—X—NH—Z—NH2 (IIa); and RO—X—NH—Z—NH3+Y? (IIb), in which X is an aliphatic alkylene group containing 2 to 6 carbon atoms; Z is an aliphatic alkylene group containing 2 to 6 carbon atoms; Y? is an anion; and R is an aliphatic iso C13H27? group with average branching degree ranging from 1.5 to 3.5. The compounds are particularly suitable as flotation collectors for enriching an iron mineral from a silicate-containing iron ore.
    Type: Application
    Filed: April 10, 2012
    Publication date: February 20, 2014
    Applicant: BASF SE
    Inventors: Christian Bittner, Bernhard Ulrich von Vacano, Alexsandro Berger, Roland Boehn, Guenter Oetter, Joerg Nieberle
  • Publication number: 20140021104
    Abstract: The invention relates to a process for enriching an iron mineral from a silicate containing iron ore by inverse flotation comprising the addition of a collector or collector composition comprising at least one of the compounds of formulae RO—X—NH2 (Ia); RO—X—NH3+Y? (Ib); RO—X—NH—Z—NH2 (IIa); and RO—X—NH—Z—NH3+Y? (IIb), in which X is a linear or branched aliphatic alkylene group containing 2 to 6 carbon atoms; Z is a linear or branched aliphatic alkylene group containing 2 to 6 carbon atoms; Y? is an anion; and R is an aliphatic group of the formula (I) C5H11CH(C3H7)CH2— (I) wherein the C5H11 moeity of the aliphatic group of the formula (I) comprises 70 to 99% by weight n-C5H11—, and 1 to 30% by weight C2H5CH(CH3)CH2— and/or CH3CH(CH3)CH2CH2—.
    Type: Application
    Filed: April 10, 2012
    Publication date: January 23, 2014
    Applicant: BASF SE
    Inventors: Christian Bittner, Joerg Nieberle, Bernhard Ulrich Von Vacano, Alexsandro Berger, Roland Boehn, Guenter Oetter
  • Publication number: 20130177839
    Abstract: Provide is a reduction catalyst, which comprises conductive carbon and a palladium-gold alloy supported on the carbon, wherein the alloying degree of said alloy is 50 to 100%. This palladium-supported catalyst has an excellent reduction ability, and exhibits a high conversion ratio and preferably an excellent selectivity when used for hydrogenation reaction. The reduction catalyst is useful as a catalyst for oxygen reduction or as a catalyst for hydrogenation. The catalyst for oxygen reduction is useful as a cathode electrode catalyst for polymer electrolyte fuel cells. The cathode electrode catalyst can be used for a cathode electrode for polymer electrolyte fuel cells.
    Type: Application
    Filed: October 26, 2011
    Publication date: July 11, 2013
    Applicant: N.E. CHEMCAT CORPORATION
    Inventors: Tomoteru Mizusaki, Kiyotaka Nagamori
  • Patent number: 8242311
    Abstract: The present invention relates to a process for preparing 2,2-difluoroethylamine of the formula (I) and salts thereof, for example sulphates, hydrochlorides or acetates, which proceeds from difluoroacetonitrile.
    Type: Grant
    Filed: December 9, 2010
    Date of Patent: August 14, 2012
    Assignee: Bayer Cropscience AG
    Inventors: Norbert Lui, Stefan Antons, Wahed Ahmed Moradi
  • Publication number: 20120149903
    Abstract: The present invention relates to a process for purifying a reaction output which comprises 3-aminopropanol and is obtained in the reaction of ethylene cyanohydrin with hydrogen in the presence of ammonia, which comprises distilling the reaction output comprising 3-aminopropanol in two or more stages, the ammonia content of the reaction output comprising 3-aminopropanol before introduction into the first distillation stage being 1% by weight or less and the temperature in the distillation stages being not more than 135° C. The invention further relates to a process for preparing 3-aminopropanol by reacting ethylene cyanohydrin with hydrogen in the presence of ammonia, which comprises performing the purification of the reaction output comprising 3-aminopropanol in accordance with the invention.
    Type: Application
    Filed: December 14, 2011
    Publication date: June 14, 2012
    Applicant: BASF SE
    Inventors: Manfred Knoll, Andreas Edgar Herrmann, Dominik Herbrecht
  • Publication number: 20110313188
    Abstract: The present invention relates to a catalyst comprising one or more elements selected from the group consisting of cobalt, nickel and copper, said catalyst being present in the form of a structured monolith, wherein said catalyst comprises one or more elements selected from the group of the alkali metals, alkaline earth metals and rare earth metals. The invention further relates to processes for preparing the inventive catalyst and to the use of the inventive catalyst in a process for hydrogenating organic substances, especially for hydrogenating nitriles.
    Type: Application
    Filed: February 4, 2010
    Publication date: December 22, 2011
    Applicant: BASF SE
    Inventors: Christof Wilhelm Wigbers, Jochen Steiner, Martin Ernst, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder
  • Publication number: 20110166388
    Abstract: The present invention relates to a process for preparing 2,2-difluoroethylamine of the formula (I) and salts thereof, for example sulphates, hydrochlorides or acetates, which proceeds from difluoroacetonitrile.
    Type: Application
    Filed: December 9, 2010
    Publication date: July 7, 2011
    Applicant: BAYER CROPSCIENCE AG
    Inventors: Norbert Lui, Stefan Antons, Wahed Ahmed Moradi
  • Patent number: 7939027
    Abstract: 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 bas
    Type: Grant
    Filed: January 6, 2010
    Date of Patent: May 10, 2011
    Assignee: BASF SE
    Inventors: Martin Ernst, Steffen Oehlenschläger, Frank Kuhnke, Karl-Heinz Roβ, Roland Deeg, Johann-Peter Melder
  • Patent number: 7875740
    Abstract: The iron-containing catalyst suitable for use as a catalyst contains a) iron or a mixture containing iron and an iron-based compound. The iron has an average crystallite size ranging from 1-35 nm measured by X-ray diffraction.
    Type: Grant
    Filed: October 18, 2002
    Date of Patent: January 25, 2011
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Ansmann, Christoph Benisch, Peter Baβler, Rolf-Hartmuth Fischer, Stefan Maixner, Johann-Peter Melder, Hermann Luyken
  • Publication number: 20100280274
    Abstract: A nickel slurry comprising a nickel catalyst, water and at least one rheology modifier, the activity of the nickel catalyst being equal to or greater than the activity of the equivalent nickel catalyst contained in a slurry which does not comprise rheology modifiers, wherein the at least one rheology modifier provides high viscosity at low shear stress and low viscosity at high shear stress.
    Type: Application
    Filed: June 29, 2010
    Publication date: November 4, 2010
    Applicant: JOHNSON MATTHEY PLC
    Inventor: James Spencer Dalton
  • Publication number: 20100261863
    Abstract: A multibranched polyoxyalkylene compound represented by the following formula (1): CH2-L1-(OA1)n-L2-X CH(OA2)mOR1 CH(OA2)mOR1 CH(OA2)mOR1 CH2(OA2)mOR1 ??(1) wherein R1 is the same or different and is a hydrocarbon group having 1 to 24 carbon atoms, OA1 and OA2 are the same or different and are an oxyalkylene group having 2 to 4 carbon atoms, n and m are the same or different and are an average number of moles of the oxyalkylene group added, n represents 0 to 1000, m is the same or different and represents 10 to 1000, X represents a functional group capable of reacting with an amino group, a mercapto group, an aldehyde group, a carboxyl group, a triple bond, or an azide group to form a chemical bond, and L1 and L2 are the same or different and are a single bond, an alkylene group, or an alkylene group in which at least one bond selected from an ester bond, a urethane bond, an amide bond, an ether bond, and an amino is interposed.
    Type: Application
    Filed: March 31, 2010
    Publication date: October 14, 2010
    Applicant: NOF CORPORATION
    Inventors: Tsuyoshi TAKEHANA, Ken-ichiro NAKAMOTO, Chika ITOH
  • Patent number: 7781618
    Abstract: The present invention relates to a method for producing an unsaturated aliphatic primary amine including subjecting an unsaturated aliphatic nitrile having 16 to 22 carbon atoms to hydrogen reduction in the presence of ammonia using a hydrogenation catalyst to produce an unsaturated aliphatic primary amine, wherein 0.01 parts by weight to 1.0 part by weight of aromatic carboxylic acid amide is added based on 100 parts by weight of the unsaturated aliphatic nitrile, and a partial pressure ratio of ammonia to hydrogen is adjusted to 8/2 to 6/4. The present invention also relates to an unsaturated aliphatic primary amine, which is produced by the production method.
    Type: Grant
    Filed: March 5, 2008
    Date of Patent: August 24, 2010
    Assignee: Lion Akzo Co., Ltd.
    Inventors: Michito Makimura, Hiroyuki Izumoto
  • Publication number: 20100210878
    Abstract: There is disclosed a process for hydrogen release and chemical storage by dehydrogenating low molecular weight aliphatic amines and di-amines to produce their corresponding nitriles in a reactor system containing a hydrogen fractionation membrane (or sweep gas) to quickly remove any and all hydrogen generated during the dehydrogenation reaction. This disclosure further provides a process for hydrogen recovery using bi- and tri-functional amines that produce corresponding nitriles and high density hydrogen release.
    Type: Application
    Filed: February 17, 2010
    Publication date: August 19, 2010
    Applicant: Asemblon, Inc.
    Inventors: Esmaeel Naeemi, David G. O'Connor
  • Patent number: 7767859
    Abstract: 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: Grant
    Filed: August 9, 2007
    Date of Patent: August 3, 2010
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kazuhiko Amakawa, Yoshiaki Yamamoto
  • Publication number: 20100137592
    Abstract: A process for the preparation of famciclovir a compound of Formula (I) and its intermediates.
    Type: Application
    Filed: June 2, 2008
    Publication date: June 3, 2010
    Inventors: Asif Parvez Sayyed, Murali Krishna Ankaraju, Ravinder Reddy Vennapureddy, Shankar Rama, Ramesh Dandala, Sivakumaran Meenakshisunderam
  • Patent number: 7723547
    Abstract: 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 base,
    Type: Grant
    Filed: October 31, 2006
    Date of Patent: May 25, 2010
    Assignee: BASF SE
    Inventors: Martin Ernst, Steffen Oehlenschläger, Frank Kuhnke, Karl-Heinz Roβ, Ronald Deeg, Johann-Peter Melder
  • Patent number: 7595029
    Abstract: The invention pertains to an improved apparatus comprised of a monolith catalytic reactor having an inlet and an outlet and a static mixer having an inlet and an outlet thereto with the outlet of said static mixer in communication with the inlet of said monolith catalytic reactor. The invention also pertains to an improvement in a process for effecting a reaction in the monolith catalytic reactor wherein a reactant gas and reactant liquid are introduced to the inlet to the monolith catalytic reactor, reacted and, then, the reaction product passed through the outlet of the monolith catalytic reactor.
    Type: Grant
    Filed: February 1, 2005
    Date of Patent: September 29, 2009
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Keith Allen Welp, Anthony Rocco Cartolano, David Joseph Parrillo, Richard Peter Boehme, Reinaldo Mario Machado, Sylvia Caram
  • Patent number: 7453012
    Abstract: 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: Grant
    Filed: January 20, 2003
    Date of Patent: November 18, 2008
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Gérald Bocquenet, André Chesnais, Jean-Michel Desire, Philippe Leconte, Lionel Sever
  • Patent number: 7381845
    Abstract: A process for hydrogenating nitrile functions present in organic compounds over at least one heterogeneous catalyst, in which the hydrogenation is carried out in the presence of an ionic liquid, is described.
    Type: Grant
    Filed: December 20, 2004
    Date of Patent: June 3, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Verena Weiskopf, Till Gerlach, Kirsten Wenz
  • Patent number: 7291754
    Abstract: Process for the catalytic hydrogenation of a nitrite in the presence of an amine and a catalyst wherein the catalyst is a liquid-rinsed Raney-type catalyst contacted with a hydroxide prior to contacting the catalyst with the amine. The process results in higher selectivity in the formation of diamines from diniriles.
    Type: Grant
    Filed: January 21, 2004
    Date of Patent: November 6, 2007
    Assignee: DSM IP Assets B.V.
    Inventors: Franciscus H. A. M. Vandenbooren, Hubertus J. M. Bosman, Alexander V. Peters, Maria J. G. Van Den Boer
  • Patent number: 7214829
    Abstract: The present invention relates to an improvement in a process for preparing primary amines by hydrogenating nitriles. The improvement in the hydrogenation process is that a hydrogenation catalyst modified ex situ with preadsorbed alkali metal carbonate or hydrogencarbonate such as K2CO3 or KHCO3 is used.
    Type: Grant
    Filed: February 13, 2003
    Date of Patent: May 8, 2007
    Assignee: Clariant Produkte (Deutschland) GmbH
    Inventors: Sandor Goeboeloes, Andras Fasi, Jozsef Margitfalvi, Laszlone Millian
  • Patent number: 7208448
    Abstract: The invention relates to a passivated hydrogenation catalyst that is embedded in a primary amine, a derivative thereof, and/or a nitrile, the process to make such catalysts, as well as the use of such catalysts in a hydrogenation process in which an amine or a derivative thereof is produced.
    Type: Grant
    Filed: March 13, 2003
    Date of Patent: April 24, 2007
    Assignee: Akzo Nobel N.V.
    Inventors: Thale Jacob Ottens, Jacobus Van Den Berg, Paul Van Poecke
  • Patent number: 7196223
    Abstract: A nitrile-containing mixture, which includes a nitrile dissolved in a higher alcohol solvent, and hydrogen are fed to a reactor containing a catalyst. An amine is produced by hydrogenating the nitrile that is dissolved in the higher alcohol solvent. In a preferred embodiment, the reactor also contains a caustic solution. The preferred nitrile-containing mixture includes octadecaneditrile (ODDN) and hexanol to produce a preferred octadecanediamine (ODDA) through hydrogenation.
    Type: Grant
    Filed: May 3, 2005
    Date of Patent: March 27, 2007
    Assignee: Solutia, Inc.
    Inventors: Tom L. Flowers, Anthony K. Uriarte, Shannon Davis, Gregory J. Ward
  • Patent number: 7115781
    Abstract: An oxidic composition which is suitable as a catalyst having divalent and trivalent iron in an atomic ratio of divalent to trivalent iron in the range from greater than 0.5 to 5.5 and oxygen as a counterion to the divalent and trivalent iron. The catalyst composition is useful in the hydrogenation of nitriles to amines.
    Type: Grant
    Filed: October 18, 2002
    Date of Patent: October 3, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Ansmann, Christoph Benisch, Peter Bassler, Rolf-Hartmuth Fischer, Stefan Maixner, Johann-Peter Melder, Hermann Luyken
  • Patent number: 7109378
    Abstract: The invention pertains to an improved apparatus comprised of a monolith catalytic reactor having an inlet and an outlet and a static mixer having an inlet and an outlet thereto with the outlet of said static mixer in communication with the inlet of said monolith catalytic reactor. The invention also pertains to an improvement in a process for effecting a reaction in the monolith catalytic reactor wherein a reactant gas and reactant liquid are introduced to the inlet to the monolith catalytic reactor, reacted and, then, the reaction product passed through the outlet of the monolith catalytic reactor.
    Type: Grant
    Filed: January 21, 2002
    Date of Patent: September 19, 2006
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Keith Allen Welp, Anthony Rocco Cartolano, David Joseph Parrillo, Richard Peter Boehme, Reinaldo Mario Machado, Sylvia Caram
  • Patent number: 6951959
    Abstract: 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: Grant
    Filed: December 9, 2003
    Date of Patent: October 4, 2005
    Assignee: Solutia Inc.
    Inventors: Gregory J. Ward, Bryan C. Blanchard
  • Patent number: 6878849
    Abstract: This invention relates to improved catalytic compositions suited for use in hydrogenation processes and to an improved process for hydrogenating organic compounds as in amination of alcohols or hydrogenation of nitrile and nitro groups to the amine using the catalyst. The catalytic composition is more particularly an improvement in nickel catalysts promoted with palladium carried on a support. The improvement resides in including a promoting effect of a metal M and/or its oxide, selected from Zn, Cd, Cu, and Ag, typically from about 0.01 to 10% by weight of the support.
    Type: Grant
    Filed: April 15, 2004
    Date of Patent: April 12, 2005
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Hao Ding
  • Patent number: 6790996
    Abstract: The invention relates to a process for preparing primary amines by hydrogenating nitrites in the presence of a catalyst comprising cobalt and optionally, in addition, nickel and also at least one further doping metal on a particulate support material, the cobalt and, if present, the nickel having an average particle size of from 3 to 30 nm in the active catalyst. The invention further relates to the use of the catalyst in a process for preparing primary amines by hydrogenating nitrites.
    Type: Grant
    Filed: October 17, 2002
    Date of Patent: September 14, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Ansmann, Christoph Benisch
  • Patent number: 6790994
    Abstract: The present invention relates to a process for the hydrogenation of nitrile functional groups to amine functional groups. It relates more particularly to a process for the complete or partial hydrogenation of dinitrile compounds to diamine or aminonitrile compounds. The invention relates to a process for the hydrogenation of nitrile functional groups to amine functional groups using hydrogen in the presence of a hydrogenation catalyst and of a strong inorganic base preferably deriving from an alkali metal or alkaline earth metal. According to the invention, the process comprises a stage of conditioning the catalyst which consists in mixing the hydrogenation catalyst, a predetermined amount of strong inorganic base and a solvent in which the strong inorganic base is not very soluble. This solvent is an amine compound, such as hexamethylenediamine in the case of the hydrogenation of adiponitrile to HMD and/or aminocapronitrile.
    Type: Grant
    Filed: January 10, 2003
    Date of Patent: September 14, 2004
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Vincent Boschat, Philippe Leconte
  • Patent number: 6790995
    Abstract: 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: Grant
    Filed: January 3, 2002
    Date of Patent: September 14, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Pfeffinger, Michael Hüllmann, Arthur Höhn, Frank Funke, Frank Ohlbach, Till Gerlach
  • Patent number: 6762324
    Abstract: This invention relates to improved catalytic compositions suited for use in hydrogenation processes and to an improved process for hydrogenating organic compounds as in amination of alcohols or hydrogenation of nitro groups to the amine using the catalyst. The catalytic composition is more particularly an improvement in nickel catalysts promoted with palladium carried on a support. The improvement resides in including a promoting effect of a metal M and/or its oxide, selected from Zn, Cd, Cu, and Ag, typically from about 0.01 to 10% by weight of the support.
    Type: Grant
    Filed: May 1, 2002
    Date of Patent: July 13, 2004
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Hao Ding
  • Patent number: 6677486
    Abstract: Nitriles are hydrogenated to primary amines over an activated, alpha-Al2O3-containing, macroporous Raney catalyst based on an alloy of aluminum and at least one transition metal selected from the group consisting of iron, cobalt and nickel, and, if desired, one or more further transition metals selected from the group consisting of titanium, zirconium, chromium and manganese, which is obtainable by a process comprising the steps in the order (a)-(f): (a) preparing a kneadable composition comprising the alloy, a shaping aid, water and a pore former; (b) shaping the kneadable composition to form a shaped body; (c) calcining the shaped body; (d) activating the calcined shaped body by treatment with aqueous alkali metal hydroxide solution; (e) rinsing the shaped catalyst body with aqueous alkali metal hydroxide solution; (f) rinsing the shaped catalyst body with water.
    Type: Grant
    Filed: November 7, 2001
    Date of Patent: January 13, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
  • Patent number: 6660887
    Abstract: 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: Grant
    Filed: December 23, 2002
    Date of Patent: December 9, 2003
    Assignee: Solutia Inc.
    Inventors: Gregory J. Ward, Bryan C. Blanchard
  • Patent number: 6649799
    Abstract: 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: Grant
    Filed: December 21, 2001
    Date of Patent: November 18, 2003
    Assignee: Degussa AG
    Inventors: Daniel Ostgard, Monika Berweiler, Stefan Röder
  • Publication number: 20030120115
    Abstract: The invention relates to a process for preparing primary amines by hydrogenating nitrites in the presence of a catalyst comprising cobalt and optionally, in addition, nickel and also at least one further doping metal on a particulate support material, the cobalt and, if present, the nickel having an average particle size of from 3 to 30 nm in the active catalyst. The invention further relates to the use of the catalyst in a process for preparing primary amines by hydrogenating nitrites.
    Type: Application
    Filed: October 17, 2002
    Publication date: June 26, 2003
    Inventors: Andreas Ansmann, Christoph Benisch
  • Patent number: 6576794
    Abstract: A process for producing an ether amine (3), which comprises reacting a primary or secondary alcohol (1), ROH, with acrylonitrile in an amount of 0.8 to 1.2 equivalents of the alcohol (1) in the presence of an alkali metal hydroxide in an amount of not less than 0.01 part by weight, but less than 0.05 part by weight per 100 parts by weight of the alcohol (1) to obtain an alkyloxypropionitrile (2), and then adding water to the reaction system without removing the alkali metal hydroxide therefrom and effecting hydrogenation using a hydrogenation catalyst: ROH(1)+CH2=CHCN→ROCH2CH2CN(2)→ROCH2CH2CH2NH2(3) wherein R denotes a linear or branched alkyl or alkenyl group having 6 to 24 carbon atoms.
    Type: Grant
    Filed: December 17, 2001
    Date of Patent: June 10, 2003
    Assignee: Kao Corporation
    Inventors: Tetsuaki Fukushima, Hiroyuki Masuda, Uichiro Nishimoto, Hiroshi Abe
  • Patent number: 6525223
    Abstract: 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: Grant
    Filed: December 27, 2001
    Date of Patent: February 25, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Pfeffinger, Michael Hüllmann, Arthur Höhn, Frank Funke, Frank Ohlbach, Till Gerlach
  • Patent number: 6476270
    Abstract: 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: Grant
    Filed: November 14, 2001
    Date of Patent: November 5, 2002
    Assignee: Rohm and Haas Company
    Inventor: Newman Mayer Bortnick
  • Patent number: 6469211
    Abstract: In a process for the continuous hydrogenation of nitrites to primary amines in the liquid phase over a suspended, activated Raney catalyst based on an alloy of aluminum and at least one transition metal selected from the group consisting of iron, cobalt and nickel, and, if desired, one or more further transition metals selected from the group consisting of titanium, zirconium, chromium and manganese, the hydrogenation is carried out in the absence of ammonia and basic alkali metal compounds or alkaline earth metal compounds.
    Type: Grant
    Filed: November 14, 2001
    Date of Patent: October 22, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
  • Patent number: 6462238
    Abstract: Disclosed is a process for selectively reducing a nitrile containing organic compound that also contains a sulfone moiety, the nitrile being reduced to a primary amine.
    Type: Grant
    Filed: April 27, 2001
    Date of Patent: October 8, 2002
    Assignee: Array BioPharma, Inc.
    Inventors: Jack (ChanKou) Hwang, Eugene Tarlton, Anthony D. Piscopio
  • Patent number: 6399830
    Abstract: This invention pertains to an improvement in a process for the formation of secondary or tertiary amines by the catalytic reductive amination of a nitrile with a primary amine. The catalyst employed in the improved reductive amination process is one that has been promoted with an acidic promoter preferably a solid phase acidic promoter.
    Type: Grant
    Filed: December 13, 2000
    Date of Patent: June 4, 2002
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John Nelson Armor, Michael Edward Ford, William Eamon Carroll
  • Patent number: 6384283
    Abstract: The present invention relates to a process for the preparation of aminonitrile and of diamine by catalytic hydrogenation of dinitrile. It consists of a process for the preparation of aminonitrile and of diamine by catalytic hydrogenation of aliphatic dinitrile having from 3 to 12 carbon atoms, characterized in that the final reaction mixture, the catalyst of which has been separated beforehand, is acidified by addition of a sufficient amount of an inorganic or organic acid, before being subjected to an operation of distillation of the products of the reaction and of the unconverted dinitrile. It relates more particularly to the preparation of 6-aminocapronitrile and of hexamethylenediamine by hydrogenation of adiponitrile. The 6-aminocapronitrile can be hydrolysed in the liquid phase or in the gas phase to result in caprolactam. The hexamethylenediamine can be used very particularly to prepare polyamide-6,6 by reaction with adipic acid.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: May 7, 2002
    Assignee: Rhodia Fiber & Resin Intermediates
    Inventor: Philippe Leconte
  • Patent number: 6380420
    Abstract: A process for preparing fatty amines by the cross-metathesis of normal alpha olefins and acrylonitrile to form an intermediate fatty acid nitrile which is hydrogenated to the corresponding fatty amine.
    Type: Grant
    Filed: September 8, 2000
    Date of Patent: April 30, 2002
    Assignee: Chevron U.S.A. Inc.
    Inventors: William L. Schinski, Michael S. Driver
  • Patent number: 6307104
    Abstract: The present invention relates to a process for producing both of a primary amine compound and an alkylene oxide adduct thereto, given that the both are excellent in color, with high yield. That is, the process comprises hydrogenating a nitrile compound in the presence of a Raney catalyst comprising 90 to 96% by weight of Ni, 3 to 9% by weight of Al and 0.5 to 3% by weight of Mo being based on the total of the atoms of Ni, Al and Mo to obtain the primary amine compound. Further, an alkylene oxide may be added thereto to obtain an alkylene oxide adduct to the primary amine compound.
    Type: Grant
    Filed: April 19, 2000
    Date of Patent: October 23, 2001
    Assignee: Kao Corporation
    Inventors: Wataru Yoshida, Tetsuaki Fukushima
  • Patent number: 5874625
    Abstract: An improved, optimized industrial process has been found for the hydrogenation of organic nitrites into primary amines, which essentially consists of contacting a dried charge of at least one organic nitrile, aqueous alkali metal hydroxide, at least one Raney slurry hydrogenation catalyst, water and hydrogen for an effective time and at an effective temperature and pressure, wherein the improvements comprise eliminating the steps of drying the charge and adding water and reducing the required water to about 0.2%. Secondary and tertiary amine formation is low, as is moisture content and neither precious metals such as rhodium, nor strategic metals, such as cobalt nor ammonia gas nor solvents are required. Surprisingly, it has been found that water levels less than that taught in the prior art are effective at suppressing secondary and tertiary amine production, while still producing repeatable product on an industrial scale and with reduced cycle time, energy and catalyst charge.
    Type: Grant
    Filed: November 4, 1996
    Date of Patent: February 23, 1999
    Assignee: Henkel Corporation
    Inventor: A. Fred Elsasser
  • Patent number: 5869653
    Abstract: An improved process for the catalytic hydrogenation of nitriles. The basic process comprises contacting the nitrile with hydrogen in the presence of a sponge or Raney cobalt catalyst under conditions for effecting conversion of the nitrile group to the primary amine. The improvement in the hydrogenation process resides in effecting the hydrogenation in the presence of a catalytic amount of lithium hydroxide and water. To achieve a catalytic amount of lithium hydroxide, the catalyst may be pretreated with the lithium hydroxide and/or the reaction may be carried out with the lithium hydroxide present in the reaction medium.
    Type: Grant
    Filed: October 30, 1997
    Date of Patent: February 9, 1999
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Thomas Albert Johnson
  • Patent number: 5847220
    Abstract: Disclosed is an improved process for the catalytic hydrogenation of cyanopropionaldehyde alkyl acetals (CPAA) to form the aminobutyraldehyde alkyl acetals. The basic process comprises hydrogenating the cyanopropionaldehyde alkyl acetals by contacting said cyanopropionaldehyde alkyl acetals with hydrogen in the presence of a nickel or cobalt catalyst under conditions for reducing the nitrile group to the primary amine. The improvement resides in effecting the hydrogenation of a cyanopropionitrile dialkyl acetal feedstock containing contaminating levels of cyanopropionaldehyde in the presence of ammonia or a primary amine and alkali metal hydroxide.
    Type: Grant
    Filed: June 16, 1997
    Date of Patent: December 8, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Kevin Rodney Lassila
  • Patent number: 5801286
    Abstract: The present invention relates to the field of the catalytic hydrogenation of nitrites to amines and, more particularly, of dinitriles such as adiponitrile (ADN) to diamines such as hexamethylenediamine (HMD).More precisely, the present invention relates to a process for the preparation of a catalyst for the hydrogenation of nitriles to amines of Raney nickel type doped with at least one additional metal element selected from columns IVb, Vb and VIb of the periodic classification.It is targeted at providing an economic and easy-to-implement process which makes it possible to obtain catalysts which are both active and selective with respect to nitrites and stable.The process is characterized in that it consists in suspending Raney nickel in a solution, preferably an acid solution, of the additional metal element.
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: September 1, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michele Besson, Georges Cordier, Pierre Fouilloux, Jacqueline Masson
  • Patent number: 5789621
    Abstract: A process for preparing an NH.sub.2 -containing compound by hydrogenating a compound containing at least one unsaturated carbon-nitrogen bond with hydrogen in the presence of a catalyst at temperatures not below room temperature and elevated hydrogen partial pressure in the presence or absence of a solvent which process includes the following steps:a) using a catalyst comprising a cobalt- and/or iron-containing catalyst, andb) after the conversion based on the compound to be hydrogenated and/or the selectivity based on the desired product has or have dropped below a defined value or the amount of an unwanted by-product has risen beyond a defined value, interrupting the hydrogenation by stopping the feed of the compound to be hydrogenated and of the solvent, if used,c) treating the catalyst at from 150.degree. to 400.degree. C. with hydrogen using a hydrogen pressure within the range from 0.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: August 4, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Schnurr, Guido Voit, Klemens Flick, Rolf-Hartmuth Fischer
  • Patent number: 5763669
    Abstract: This invention relates to a process of preparing a ruthenium complex of the formula RuH.sub.2 (PR.sub.3).sub.2 L.sub.2 wherein PR.sub.3 is an organophosphorus ligand and L is H.sub.2 or PR.sub.3 ; a catalyst comprising at least one ruthenium complex having the formula RuH.sub.2 (PR.sub.3)L.sup.1.sub.3 wherein L.sup.1 is a neutral electron pair donor ligand; a process for preparing the catalyst and its use in situ in the hydrogenation of nitriles.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: June 9, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Richard Paul Beatty, Rocco Angelo Paciello