Forming Amine Group Of Alicyclic Ring Containing Compound Directly By Reduction Patents (Class 564/448)
  • Patent number: 11180440
    Abstract: The present disclosure relates to a method for preparing isophorone diamine by means of a hydrogenation reduction of isophorone nitrile imine. The hydrogenation reduction is continuously carried out in a multi-stage bubble column reactor loaded with a supported alkaline cobalt-based catalyst, wherein isophorone nitrile imine is successively in countercurrent contact with hydrogen in each stage of the reactor to carry out a hydrogenation reduction reaction, so as to obtain the isophorone diamine. The preparation method solves the problem of back-mixing, and further improves the conversion rate and the cis/trans ratio of the product.
    Type: Grant
    Filed: November 30, 2018
    Date of Patent: November 23, 2021
    Assignees: Zhejiang Nhu Company Ltd., Zhejiang University, Shandong Nhu Amino Acid Co., Ltd., Shandong Nhu Fine Chemical Science and Technology Company Ltd.
    Inventors: Zhirong Chen, Jianyong Mao, Baishan Hu, Guanbing Li, Haoran Li, Yu Wang, Yingkuo Yang, Qing Liu, Jiyu Tang, Weiyong Chen
  • Patent number: 10906865
    Abstract: A method for producing 1,4-dicyanocyclohexane, having a step of obtaining 1,4-dicyanocyclohexane by subjecting a heated concentrate of an aqueous ammonia solution of 1,4-cyclohexanedicarboxylic acid to a cyanation reaction.
    Type: Grant
    Filed: September 28, 2017
    Date of Patent: February 2, 2021
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akifumi Iida, Yuta Ohmori, Emi Nakano, Aoi Yamazoe
  • Patent number: 9663443
    Abstract: A process for making a tertiary aminoalcohol compound is disclosed. The process comprises using an excess amount of a carbonyl compound in a condensation step between the carbonyl compound and a nitroalkane in the presence of a catalytic amount of a tertiary aminoalcohol compound, and conducting a hydrogenation/alkylation step to produce the tertiary aminoalcohol. The tertiary aminoalcohol compound used to catalyze the condensation step is preferably the same tertiary aminoalcohol compound produced in the hydrogenation/alkylation step. The process uses fewer steps than conventional processes.
    Type: Grant
    Filed: July 16, 2012
    Date of Patent: May 30, 2017
    Assignee: ANGUS CHEMICAL COMPANY
    Inventors: David W. Moore, Christian Spieker, John D. Gummere
  • Patent number: 8884063
    Abstract: The present invention relates to a continuous process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine by reacting a feed stream comprising 3-cyano-3,5,5-trimethylcyclohexylimine with hydrogen and ammonia over hydrogenation catalysts, wherein the basicity of the reaction mixture is increased during the reaction by bringing the reaction mixture into contact with a basic compound which is not ammonia and/or a basic catalyst after part of the 3-cyano-3,5,5-trimethylcyclohexylimine has been reacted.
    Type: Grant
    Filed: December 19, 2007
    Date of Patent: November 11, 2014
    Assignee: BASF SE
    Inventors: Martin Ernst, Thomas Hill, Piotr Makarczyk, Johann-Peter Melder
  • Patent number: 8877976
    Abstract: The invention relates to an improved process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine, referred to hereinafter as isophoronediamine or IPDA for short, by means of catalytic hydrogenation and/or catalytic reductive amination (also referred to as aminating hydrogenation) of 3-cyano-3,5,5-trimethylcyclohexanone, also called isophoronenitrile or IPN for short hereinafter.
    Type: Grant
    Filed: November 17, 2011
    Date of Patent: November 4, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Christian Lettmann, Guido Streukens, Matthias Orschel, Gerda Grund
  • Patent number: 8865938
    Abstract: A method for producing bis(aminomethyl)cyclohexanes includes a nuclear hydrogenation step of producing hydrogenated phthalic acids or phthalic acid derivatives by nuclear hydrogenation of phthalic acids or phthalic acid derivatives of at least one selected from the group consisting of phthalic acids, phthalic acid esters, and phthalic acid amides; a cyanation step of treating the hydrogenated phthalic acids or phthalic acid derivatives obtained in the nuclear hydrogenation step with ammonia, thereby producing dicyanocyclohexanes; and an aminomethylation step of treating the dicyanocyclohexanes obtained in the cyanation step with hydrogen, thereby producing bis(aminomethyl)cyclohexanes. In the cyanation step, metal oxide is used as a catalyst, and the obtained dicyanocyclohexanes have a metal content of 3000 ppm or less.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: October 21, 2014
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Naritoshi Yoshimura, Shinji Kiyono, Tetsuya Hamada, Eiji Watanabe, Saiko Sawada
  • Patent number: 8865939
    Abstract: A method for producing trans-1,4-bis(aminomethyl)cyclohexane includes a nuclear hydrogenation step of producing a hydrogenated terephthalic acid or terephthalic acid derivative by nuclear hydrogenation of a terephthalic acid or terephthalic acid derivative, the terephthalic acid or terephthalic acid derivative being at least one selected from the group consisting of terephthalic acid, terephthalic acid ester, and terephthalic acid amide; a cyanation step of treating the hydrogenated terephthalic acid or terephthalic acid derivative with ammonia, thereby producing 1,4-dicyanocyclohexane, and producing trans-1,4-dicyanocyclohexane from the obtained 1,4-dicyanocyclohexane; and an aminomethylation step of treating the trans-1,4-dicyanocyclohexane with hydrogen, thereby producing trans-1,4-bis(aminomethyl)cyclohexane. Metal oxide is used as a catalyst in the cyanation step, and the obtained trans-1,4-dicyanocyclohexane has a metal content of 3000 ppm or less.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: October 21, 2014
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Naritoshi Yoshimura, Shinji Kiyono, Tetsuya Hamada, Eiji Watanabe, Saiko Sawada
  • Patent number: 8829245
    Abstract: Provided is a 3-aminomethyl-3,5,5-trimethylcyclohexylamine preparation method. A feeding flow of 3-cyano-3,5,5-trimethylcyclohexylamine is reacted with NH3 and hydrogen in the presence of a hydrogenation catalyst; the method is characterized by: firstly adding a basic compound to the feeding flow of 3-cyano-3,5,5-trimethylcyclohexylamine, and then after a portion of 3-cyano-3,5,5-trimethylcyclohexylamine has reacted, adding an acidic compound to reaction materials for further hydrogenation reaction to prepare the product. The method ensures that the aminonitrile content in the product is low, thus effectively reducing the duration of the reaction and greatly reducing the consumption of the catalyst during the hydrogenation reaction process.
    Type: Grant
    Filed: September 6, 2011
    Date of Patent: September 9, 2014
    Assignees: Wanhua Chemical Group Co., Ltd., Wanhua Chemical (Ningbo) Co., Ltd.
    Inventors: Changsheng Chen, Yuan Li, Wenjuan Zhao, Hongyin Cui, Weiqi Hua
  • Patent number: 8692021
    Abstract: Method of preparing 1-amino-1,3,3,5,5-pentamethylcyclohexane or a pharmaceutically acceptable salt thereof (Neramexane), comprising step (iv): (iv) hydrolyzing a mixture comprising an acid, 1-formamido-1,3,3,5,5-pentamethylcyclohexane and hydrogen cyanide to yield 1-amino-1,3,3,5,5-pentamethylcyclohexane.
    Type: Grant
    Filed: September 24, 2010
    Date of Patent: April 8, 2014
    Assignee: Merz Pharma GmbH & Co. KGaA
    Inventors: Markus-Rene Gold, Valerjans Kauss, Aigars Jirgensons
  • Patent number: 8686189
    Abstract: The invention is directed to a process for producing intermediates of a compound which exhibits an activated blood coagulation factor Xa inhibitory action and which is a useful preventive and a therapeutic agent for thrombotic diseases. The intermediate production process is represented by the following reaction scheme.
    Type: Grant
    Filed: September 15, 2006
    Date of Patent: April 1, 2014
    Assignee: Daiichi Sankyo Company, Limited
    Inventors: Koji Sato, Kotaro Kawanami, Tsutomu Yagi
  • Patent number: 8674139
    Abstract: Provided is a process for making a tertiary aminoalcohol compound. The process comprises using an excess amount of a carbonyl compound in a condensation step between the carbonyl compound and a nitroalkane, and conducting a hydrogenation/alkylation step to produce the tertiary aminoalcohol. The process uses fewer steps than conventional processes.
    Type: Grant
    Filed: September 21, 2011
    Date of Patent: March 18, 2014
    Inventors: David W. Moore, Raymond J. Swedo, Asghar A. Peera
  • Publication number: 20130281664
    Abstract: The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e.
    Type: Application
    Filed: October 11, 2011
    Publication date: October 24, 2013
    Inventors: David Milstein, Ekambaram Balaraman, Chidambaram Gunanathan, Boopathy Gnanaprakasam, Jing Zhang
  • Publication number: 20130261341
    Abstract: The invention relates to an improved process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine, referred to hereinafter as isophoronediamine or IPDA for short, by means of catalytic hydrogenation and/or catalytic reductive amination (also referred to as aminating hydrogenation) of 3-cyano-3,5,5-trimethylcyclohexanone, also called isophoronenitrile or IPN for short hereinafter.
    Type: Application
    Filed: November 17, 2011
    Publication date: October 3, 2013
    Applicant: Evonik Degussa GmbH
    Inventors: Christian Lettmann, Guido Streukens, Matthias Orschel, Gerda Grund
  • Publication number: 20130253226
    Abstract: The invention relates to an improved process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine, referred to hereinafter as isophoronediamine or, in abbreviated form, IPDA, by: I. preparation of isophorone by catalyzed aldol condensations with acetone as reactant; II. reaction of isophorone with HCN to form isophoronenitrile (IPN, 3-cyano-3,5,5-trimethylcyclohexanone); III. catalytic hydrogenation and/or catalytic reductive amination (also referred to as aminative hydrogenation) of 3-cyano-3,5,5-trimethylcyclohexanone, hereinafter called isophoronenitrile or, in abbreviated form, IPN, to give the isophoronediamine.
    Type: Application
    Filed: November 18, 2011
    Publication date: September 26, 2013
    Applicant: Evonik Degussa GmbH
    Inventors: Markus Galle, Gerda Grund, Axel Hengstermann, Michael D. Hinton, Rolf Hirsch, Robert Jansen, Cord Knoop, Christian Lettmann, Juergen Lippe, Martin Maier, Joerg-Joachim Nitz, Matthias Orschel, Martina Ortelt, Norbert Richter, Armin Rix, Markus Schwarz, Guido Streukens
  • Publication number: 20130197270
    Abstract: A method for producing trans-1,4-bis(aminomethyl)cyclohexane includes a nuclear hydrogenation step of producing a hydrogenated terephthalic acid or terephthalic acid derivative by nuclear hydrogenation of a terephthalic acid or terephthalic acid derivative, the terephthalic acid or terephthalic acid derivative being at least one selected from the group consisting of terephthalic acid, terephthalic acid ester, and terephthalic acid amide; a cyanation step of treating the hydrogenated terephthalic acid or terephthalic acid derivative with ammonia, thereby producing 1,4-dicyanocyclohexane, and producing trans-1,4-dicyanocyclohexane from the obtained 1,4-dicyanocyclohexane; and an aminomethylation step of treating the trans-1,4-dicyanocyclohexane with hydrogen, thereby producing trans-1,4-bis(aminomethyl)cyclohexane. Metal oxide is used as a catalyst in the cyanation step, and the obtained trans-1,4-dicyanocyclohexane has a metal content of 3000 ppm or less.
    Type: Application
    Filed: October 5, 2011
    Publication date: August 1, 2013
    Inventors: Naritoshi Yoshimura, Shinji Kiyono, Tetsuya Hamada, Eiji Watanabe, Saiko Sawada
  • Publication number: 20130197269
    Abstract: A method for producing bis(aminomethyl)cyclohexanes includes a nuclear hydrogenation step of producing hydrogenated phthalic acids or phthalic acid derivatives by nuclear hydrogenation of phthalic acids or phthalic acid derivatives of at least one selected from the group consisting of phthalic acids, phthalic acid esters, and phthalic acid amides; a cyanation step of treating the hydrogenated phthalic acids or phthalic acid derivatives obtained in the nuclear hydrogenation step with ammonia, thereby producing dicyanocyclohexanes; and an aminomethylation step of treating the dicyanocyclohexanes obtained in the cyanation step with hydrogen, thereby producing bis(aminomethyl)cyclohexanes. In the cyanation step, metal oxide is used as a catalyst, and the obtained dicyanocyclohexanes have a metal content of 3000 ppm or less.
    Type: Application
    Filed: October 5, 2011
    Publication date: August 1, 2013
    Inventors: Naritoshi Yoshimura, Shinji Kiyono, Tetsuya Hamada, Eiji Watanabe, Saiko Sawada
  • Patent number: 8480800
    Abstract: Provided are aminoalcohol compounds for use as neutralizing agents for paints and coatings. The compounds are of the formula (I): or salt thereof, wherein R1, R2, R3, R4, R5, and n are as defined herein. Also provided are precursors of the aminoalcohol compounds and processes for making and using them.
    Type: Grant
    Filed: December 1, 2010
    Date of Patent: July 9, 2013
    Inventors: Ian A. Tomlinson, Asghar A. Peera, George David Green
  • Publication number: 20130172622
    Abstract: Provided is a process for making a tertiary aminoalcohol compound. The process comprises using an excess amount of a carbonyl compound in a condensation step between the carbonyl compound and a nitroalkane, and conducting a hydrogenation/alkylation step to produce the tertiary aminoalcohol. The process uses fewer steps than conventional processes.
    Type: Application
    Filed: September 21, 2011
    Publication date: July 4, 2013
    Applicant: ANGUS CHEMICAL COMPANY
    Inventors: David W. Moore, Raymond J. Swedo, Asghar A. Peera
  • Publication number: 20120245390
    Abstract: The present invention relates to a process for hydrogenating nitriles by means of hydrogen in the presence of a catalyst in a reactor, where the catalyst is arranged in a fixed bed, wherein the cross-sectional loading in the reactor is in the range from 5 kg/(m2s) to 50 kg/(m2s). The present invention further relates to a process for preparing downstream products of isophoronediamine (IPDA) or N,N-dimethylaminopropylamine (DMAPA) from amines prepared according to the invention.
    Type: Application
    Filed: March 22, 2012
    Publication date: September 27, 2012
    Applicant: BASF SE
    Inventors: Christof Wilhelm Wigbers, Christoph Müller, Wolfgang Mägerlein, Petr Kubanek, Thomas Heidemann, Johann-Peter Melder, Thomas Krug, Oliver Bey
  • Publication number: 20120245391
    Abstract: Method of preparing 1-amino-1,3,3,5,5-pentamethylcyclohexane or a pharmaceutically acceptable salt thereof (Neramexane), comprising step (iv): (iv) hydrolyzing a mixture comprising an acid, 1-formamido-1,3,3,5,5-pentamethylcyclohexane and hydrogen cyanide to yield 1-amino-1,3,3,5,5-pentamethylcyclohexane.
    Type: Application
    Filed: September 24, 2010
    Publication date: September 27, 2012
    Applicant: MERZ PHARMA GmbH &CO. KGaA
    Inventors: Markus-Rene Gold, Valerjans Kauss, Aigars Jirgensons
  • Publication number: 20120245389
    Abstract: The present invention relates to a process for hydrogenating organic nitriles by means of hydrogen in the presence of a catalyst in a reactor, where the shaped body catalyst is arranged in a fixed bed, wherein the shaped body in the shape of spheres or rods has in each case a diameter 3 mm or less, in the shape of tablets a height of 4 mm or less, and in the case of all other geometries in each case has an equivalent diameter L=1/a? of 0.70 mm or less, where a? is the external surface area per unit volume (mms2/mmp3), where: a ? = A p V p , where Ap is the external surface area of the catalyst particle (mms2) and Vp is the volume of the catalyst particle (mmp3). The present invention further relates to a process for preparing downstream products of isophoronediamine (IPDA) or N,N-dimethylaminopropylamine (DMAPA) from amines prepared according to the invention.
    Type: Application
    Filed: March 22, 2012
    Publication date: September 27, 2012
    Applicant: BASF SE
    Inventors: Christof Wilhelm Wigbers, Christoph Müller, Wolfgang Mägerlein, Martin Ernst, Thomas Heidemann, Johann-Peter Melder, Lucia Königsmann, Milind Joshi, Oliver Bey, Bernd Stein
  • Patent number: 8212078
    Abstract: This invention provides aromatic diimines where the diimines have imino groups with at least two carbon atoms, and either are in the form of one benzene ring having two imino groups on the ring, which imino groups are meta or para relative to each other, and in which each position ortho to an imino group bears a hydrocarbyl group, or are in the form of two benzene rings connected by an alkylene bridge and having one imino group on each ring, and in which each position ortho to an imino group bears a hydrocarbyl group.
    Type: Grant
    Filed: December 30, 2005
    Date of Patent: July 3, 2012
    Assignee: Albemarle Corporation
    Inventors: John Y. Lee, Paul L. Wiggins, Judit Orgad, Mahmood Sabahi, Vernon O. Brandt, David W. Owens
  • Publication number: 20110313187
    Abstract: The present invention relates to a process for improving the catalytic properties of 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, by contacting the catalyst with one or more basic compounds selected from the group of the alkali metals, alkaline earth metals and rare earth metals. The invention further relates to a process for hydrogenating compounds which comprise at least one unsaturated carbon-carbon, carbon-nitrogen or carbon-oxygen bond in the presence of 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, by contacting the catalyst with one or more basic compounds selected from the group of the alkali metals, alkaline earth metals and rare earth metals.
    Type: Application
    Filed: February 1, 2010
    Publication date: December 22, 2011
    Inventors: Christof Wilhelm Wigbers, Jochen Steiner, Martin Ernst, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder
  • 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: 20110146536
    Abstract: Provided are aminoalcohol compounds for use as neutralizing agents for paints and coatings. The compounds are of the formula (I): or salt thereof, wherein R1, R2, R3, R4, R5, and n are as defined herein. Also provided are precursors of the aminoalcohol compounds and processes for making and using them.
    Type: Application
    Filed: December 1, 2010
    Publication date: June 23, 2011
    Inventors: Ian A. Tomlinson, Asghar A. Peera, George D. Green
  • Patent number: 7863486
    Abstract: The present invention relates to a process for preparing an amine, which comprises the step cathodic reduction of a corresponding oxime derivative of the general formula (I) where R is C1-6-alkyl or C2-6-alkenyl which is optionally substituted by one or more substituents selected independently from the group consisting of phenyl, O—C1-6-alkyl, NH—C1-6-alkyl, N(C1-6-alkyl)2, OH and NH2; R1 is H; C1-6-alkyl or C(O)—C1-6-alkyl and A is a 5-, 6- or 7-membered hydrocarbon ring which is saturated or has a double bond and in which at least one CH2 group may, if appropriate, be replaced by —O—, —S— —NH—, —N? or —N(C1-6-alkyl)- and which may optionally be substituted by one or more further substituents selected independently from the group consisting of phenyl, C1-6-alkyl, O—C1-6-alkyl, NH—C1-6-alkyl, N(C1-6-alkyl)2, OH and NH2; wherein, based on the ring carbon bearing the substituent R, the oxime derivative has an excess of the R or S form of at least 10%.
    Type: Grant
    Filed: June 27, 2007
    Date of Patent: January 4, 2011
    Assignee: BASF SE
    Inventors: Ulrich Griesbach, Siegfried R. Waldvogel, Itamar Michael Malkowsky, Joern Kulisch
  • Patent number: 7790927
    Abstract: This invention relates to processes for the production of optically active 2-(disubstituted aryl)cyclopropylamine compounds and optically active 2-(disubstituted aryl)cyclopropane carboxamide compounds which are useful intermediates for the preparation of pharmaceutical agents, and in particular the compound [1S-(1?,2?,3?(1S*,2R*),5?)]-3-[7-[2-(3,4-difluorophenyl)-cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol.
    Type: Grant
    Filed: August 3, 2007
    Date of Patent: September 7, 2010
    Assignee: AstraZeneca AB
    Inventors: Masaru Mitsuda, Tadashi Moroshima, Kentaro Tsukuya, Kazuhiko Watabe, Masahiko Yamada
  • Patent number: 7767858
    Abstract: This invention provides aromatic diimines which have imino hydrocarbylidene groups with at least two carbon atoms, and aromatic secondary diamines which have amino hydrocarbyl groups with at least two carbon atoms. Both the aromatic diimines and the aromatic secondary diamines either are in the form of one phenyl ring, or are in the form of two phenyl rings connected by an alkylene bridge; each position ortho to an imino group or an amino group bears a hydrocarbyl group. When in the form of one phenyl ring, there are two imino groups on the ring or two amino groups on the ring; the imino groups or amino groups are meta or para relative to each other. When in the form of two phenyl rings connected by an alkylene bridge, there is either one imino group or one amino group on each phenyl ring. Also provided are processes for forming diimines and secondary diamines.
    Type: Grant
    Filed: September 14, 2007
    Date of Patent: August 3, 2010
    Assignee: Albemarle Corporation
    Inventors: Paul L. Wiggins, Judit Orgad, John Y. Lee, Mahmood Sabahi
  • Publication number: 20100191008
    Abstract: A method comprising providing a starting composition comprising a polyunsaturated fatty acid, a polyunsaturated fatty ester, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated triglyceride, or a mixture thereof; self-metathesizing the starting composition or cross-metathesizing the starting composition with at least one short-chain olefin in the presence of a metathesis catalyst to form self-/cross-metathesis products comprising: cyclohexadiene; at least one olefin; and one or more acid-, ester-, or salt-functionalized alkene; and reacting cyclohexadiene to produce at least one cycloalkane or cycloalkane derivatives.
    Type: Application
    Filed: January 29, 2009
    Publication date: July 29, 2010
    Applicant: ENERGY & ENVIRONMENTAL RESEARCH CENTER FOUNDATION
    Inventor: Edwin S. Olson
  • Patent number: 7683216
    Abstract: A process for the preparation of alkyleneimines by subjecting sulfuric acid monoesters of aminoalkanols to an at least two-stage reaction with aqueous bases at a temperature of at least 110° C. under pressure, relieving the pressure of the reaction mixture and distilling off the alkyleneimines from the reaction mixture after each reaction stage, wherein the conversion in the first stage is from 40 to 90% and that in the second stage is from more than 90% to 99.99%.
    Type: Grant
    Filed: April 18, 2008
    Date of Patent: March 23, 2010
    Assignee: BASF SE
    Inventors: Thomas Knebel, Gerd Saas, Wolfgang Schreieck, Horst Schroeder, Manfred Winter
  • Publication number: 20100036168
    Abstract: The present invention relates to a continuous process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine by reacting a feed stream comprising 3-cyano-3,5,5-trimethylcyclohexylimine with hydrogen and ammonia over hydrogenation catalysts, wherein the basicity of the reaction mixture is increased during the reaction by bringing the reaction mixture into contact with a basic compound which is not ammonia and/or a basic catalyst after part of the 3-cyano-3,5,5-trimethylcyclohexylimine has been reacted.
    Type: Application
    Filed: December 19, 2007
    Publication date: February 11, 2010
    Applicant: BASF SE
    Inventors: Martin Ernst, Thomas Hill, Piotr Makarczyk, Johann-Peter Melder
  • Publication number: 20090253937
    Abstract: The present invention relates to a process for preparing an amine, which comprises the step cathodic reduction of a corresponding oxime derivative of the general formula (I) where R is C1-6-alkyl or C2-6-alkenyl which is optionally substituted by one or more substituents selected independently from the group consisting of phenyl, O—C1-6-alkyl, NH—C1-6-alkyl, N(C1-6-alkyl)2, OH and NH2; R1 is H; C1-6-alkyl or C(O)—C1-6-alkyl and A is a 5-, 6- or 7-membered hydrocarbon ring which is saturated or has a double bond and in which at least one CH2 group may, if appropriate, be replaced by —O—, —S— —NH—, —N? or —N(C1-6-alkyl)- and which may optionally be substituted by one or more further substituents selected independently from the group consisting of phenyl, C1-6-alkyl, O—C1-6-alkyl, NH—C1-6-alkyl, N(C1-6-alkyl)2, OH and NH2; wherein, based on the ring carbon bearing the substituent R, the oxime derivative has an excess of the R or S form of at least 10%.
    Type: Application
    Filed: June 27, 2007
    Publication date: October 8, 2009
    Applicant: BASF SE
    Inventors: Ulrich Griesbach, Siegfried R. Waldvogel, Itamar Michael Malkowsky, Jörn Kulisch
  • Publication number: 20090198082
    Abstract: The present invention is to provide a process for producing dicyanonorbornane characterized by causing hydrogen cyanide to undergo addition reaction with cyanonorbornene (bicyclo[2.2.1]-5-heptene-2-carbonitrile) in the presence of a zerovalent nickel complex catalyst which is produced by using a phosphite represented by P(x)(y)(z) (wherein P is a phosphorus atom, and x, y and z are each OR, where R represents an aryl group having not more than 18 carbon atoms) as a ligand to reduce a nickel halide with at least one metal selected among zinc, cadmium, beryllium, aluminum, iron and cobalt, wherein the phosphite is one which has a phosphate content of 1.0 weight % or lower based on the whole phosphite.
    Type: Application
    Filed: June 22, 2007
    Publication date: August 6, 2009
    Applicant: MITSUI CHEMICALS , INC.
    Inventors: Norihiko Fukatsu, Hiroyuki Morijiri, Chitoshi Shimakawa, Koichi Tokunaga, Seiichi Kobayashi
  • Publication number: 20090048466
    Abstract: The invention relates to a process for preparing amines by conditioning the catalyst with ammonia.
    Type: Application
    Filed: November 29, 2006
    Publication date: February 19, 2009
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Christian Lettmann, Juergen Lippe
  • Publication number: 20080242861
    Abstract: This invention relates to methods of preparing the compounds of formula (V): Each variable in this formula is defined in the specification.
    Type: Application
    Filed: April 2, 2007
    Publication date: October 2, 2008
    Inventors: Chi-Feng Yen, Chang-Pin Huang, Cheng-Kung Hu, Ming-Chen Chou, Chi-Hsin Richard King
  • Patent number: 7411094
    Abstract: Process for preparing primary amines having a cyclopropyl unit and a primary amino group bound to an aliphatic or cycloaliphatic carbon atom (amine A) by cathodically reducing oximes having a cyclopropyl unit or oxime derivatives in which the hydrogen atom in the oxime group has been replaced by an alkyl or acyl group (oxime O) at a temperature of from 50 to 100° C. in an essentially anhydrous electrolyte solution in a divided electrolysis cell.
    Type: Grant
    Filed: July 8, 2005
    Date of Patent: August 12, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Griesbach, Harald Winsel, Hermann Putter
  • Patent number: 7405324
    Abstract: The present invention concerns a new process for synthesising aminoadamantanes of formula I in which R1 and R2 are identical or different and are H or a straight or branched alkyl group comprising from 1 to 6 carbon atoms, and addition salts thereof with inorganic or organic acids, in particular memantine hydrochloride (1-amino-3,5-dimethyladamantane hydrochloride).
    Type: Grant
    Filed: May 10, 2006
    Date of Patent: July 29, 2008
    Assignee: A.M.S.A. Anonima Materie Sintetiche E. Afini S.p.A.
    Inventors: Enrico Vigano′, Ernesto Landonio, Simona Lanfranconi, Renato Molteni
  • Publication number: 20080167488
    Abstract: The present invention relates to a process of preparing a compound of formula II, wherein R1, n, m and p are defined in the specification.
    Type: Application
    Filed: July 26, 2006
    Publication date: July 10, 2008
    Applicant: ASTRAZENECA AB
    Inventor: Maxime Tremblay
  • Patent number: 7342135
    Abstract: 3(4),7(8)-bis(aminomethyl)bicyclo[4.3.0]nonane and a process for its preparation, wherein bicyclo[4.3.0]nona-3,7-diene is reacted with synthesis gas in a homogeneous organic phase in the presence of transition metal compounds of Group VIII of the Periodic Table containing complex-bound organophosphorus compounds, and excess organophosphorus compound, at temperatures of 70 to 160° C. and pressures of 5 to 35 MPa, and the 3(4),7(8)-bisformylbicyclo[4.3.0]nonane thus obtained is reductively aminated.
    Type: Grant
    Filed: January 25, 2007
    Date of Patent: March 11, 2008
    Assignee: Celanese Chemicals Europe GmbH
    Inventors: Helmut Springer, Paolo Bavaj
  • Patent number: 7256313
    Abstract: The invention relates to processes for preparing 3-aminomethyl-3,5,5-trimethylcyclo-hexylamine (isophoronediamine, IPDA) having a high cis/trans isomer ratio. IPDA having a cis/trans isomer ratio in the range from 63/37 to 66/34 can be obtained in any desired cis/trans isomer ratio, irrespective of temperature, by reacting IPDA with H2 and NH3 in the presence of a hydrogenation catalyst. IPDA having a cis/trans isomer ratio of at least 73/27 which is an important starting material for the synthesis of polyurethanes and polyamides can be obtained by combining this isomerization process with distillative processes.
    Type: Grant
    Filed: August 6, 2003
    Date of Patent: August 14, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Funke, Thomas Hill, Jobst Rüdiger Von Watzdorf, Wolfgang Mattmann, Wolfgang Harder, Erhard Henkes, Gerd Littmann, Manfred Julius
  • Patent number: 7060857
    Abstract: In a process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine, IPDA) having a cis/trans isomer ratio of at least 70/30 from 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile, IPN), NH3 and H2, the hydrogenation is carried out at from 50 to 200° C. and a pressure of from 50 to 300 bar in the presence of a hydrogenation catalyst having an alkali metal content of ?0.03% by weight, calculated as alkali metal oxide referring to the total weight of the catalyst. The alkali metal content is made up of the contents of Li, Na, K, Rb and Cs; in particular, the alkali metal content is the Na content. A process for producing hydrogenation catalysts having an alkali metal content (in particular a sodium content) of ?0.03% by weight, calculated as alkali metal oxide/sodium oxide referring to the total weight of the catalyst, and the hydrogenation catalysts themselves are also provided by the invention.
    Type: Grant
    Filed: August 28, 2002
    Date of Patent: June 13, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Funke, Thomas Hill, Johann-Peter Melder, Ekkehard Schwab, Walter Himmel, Erhard Henkes, Hermann Petersen, Reinhard Körner
  • Patent number: 7026514
    Abstract: N,N?-bis(3-aminopropyl)cyclohexane-1,4-diamine, of formula (I), is a new compound that is prepared by hydrogenation with Raney nickel catalyst of N,N?-bis(2-cyanoethyl)-cyclohexane-1,4-diamine, the latter being prepared by reaction between 1,4-cyclohexanediamine and acrylonitrile. The oral administration to genetically alcoholic rats (from the strain UChB of the University of Chile) of the tetrametanesulfonate monohydrate of (I) causes a significant reduction in the alcohol consumption. The activity lasts for some time after the treatment period. Besides, there is a virtually null disulfiram-like adverse effect, what constitutes an advantage over the unpleasant use of some anti-alcoholism agents, such as calcium cyanamide or disulfiram itself.
    Type: Grant
    Filed: July 1, 2002
    Date of Patent: April 11, 2006
    Assignee: Garbil Pharma Investigacion Chile Ltda.
    Inventors: Norberto Bilbeny Lojo, Hernan Garcia Madrid, Maria Belen Font Arellano
  • Patent number: 6962964
    Abstract: This invention relates to improved polyepoxide resins cured with a mixture of methylene bridged poly(cycloaliphatic-aromatic)amines and a process for preparing such polyepoxide resins as well as to the methylene bridged poly(cycloaliphatic-aromatic)amine compositions and a method of making them. The improvement resides in using a curative (herein referred to as “Heavy MPCA”) comprised of the partially hydrogenated condensation product of formaldehyde and aniline or methyl substituted aniline containing a substantial amount (from 35 to 85% by weight, preferably 40 to 60% by weight) of oligomers in the form of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 and 15 aniline or methyl substituted aniline derivatives.
    Type: Grant
    Filed: February 6, 2003
    Date of Patent: November 8, 2005
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael Ulman, Gamini Ananda Vedage, David Alan Dubowik, Stephen Michael Boyce
  • Patent number: 6900355
    Abstract: The invention relates to a process for the cis-selective preparation of cyclic amines of the sertralin type by reductive alkylation of cyclic imines or their precursors and catalytic hydrogenation in the presence of copper-containing catalysts and in the presence of a protic solvent.
    Type: Grant
    Filed: March 5, 2004
    Date of Patent: May 31, 2005
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Heinz Steiner, Marc Thommen, Hans-Peter Jalett, Markus Benz
  • Publication number: 20040249214
    Abstract: Disclosed herein is a process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine by low-pressure hydrogenation of 1-amino-2-cyano-1-cyclopentene using a combination catalyst system of nickel with palladium on carbon, or a single palladium-doped Raney-type catalyst.
    Type: Application
    Filed: June 5, 2003
    Publication date: December 9, 2004
    Inventors: Ronald L. Amey, Ronald H. Mattson
  • Publication number: 20040225156
    Abstract: In a process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine, IPDA) having a cis/trans isomer ratio of at least 70/30 from 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile, IPN), NH3 and H2, the hydrogenation is carried out at from 50 to 200° C. and a pressure of from 50 to 300 bar in the presence of a hydrogenation catalyst having an alkali metal content of ≦0.03% by weight, calculated as alkali metal oxide referring to the total weight of the catalyst.
    Type: Application
    Filed: February 24, 2004
    Publication date: November 11, 2004
    Inventors: Frank Funke, Thomas Hill, Johann-Peter Melder, Ekkehard Schwab, Walter Himmel, Erhard Henkes, Hermann Petersen, Reinhard Korner
  • 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: 6710210
    Abstract: Novel N-substituted-aminomethyl cyclopropyl ketone derivatives are represented by following Formula (1): wherein R1, R2 and R3 are each a hydrogen atom or an aliphatic hydrocarbon group; and R4 and R5 are each a hydrogen atom or an arylmethyl group which may have a substituent, where at least one hydrogen atom or aryl group as a substituent is combined with a carbon atom in the methyl moiety of the arylmethyl group, and at least one of R4 and R5 is an arylmethyl group which may have a substituent. These compounds are useful for the preparation of aminomethyl cyclopropyl ketone derivatives and 2-amino-1-cyclopropylethanol derivatives or salts thereof.
    Type: Grant
    Filed: April 8, 2002
    Date of Patent: March 23, 2004
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hiroki Tanaka, Li Rui Pan, Kiyoshi Ikura
  • Patent number: 6683216
    Abstract: Disclosed is a process for the preparation of amines by continuously feeding a carboxamide, aqueous alkaline hypohalite, and aqueous alkaline hydroxide to a first reaction zone to form a N-halocarboxamide, measuring the concentration of at least one reaction component in the effluent from the first reaction zone, and using the result of that measurement to control the feed rate of at least one of the feed components of to achieve at least 90% conversion of the carboxamide in the first reaction zone. The effluent from the first reaction zone is fed continuously to a second reaction zone where it further reacts to form an aqueous solution of an amine. The effluent from the second reaction zone may be fed continuously to a distillation column. The process is particularly useful for the preparation of cyclopropylamine.
    Type: Grant
    Filed: November 6, 2002
    Date of Patent: January 27, 2004
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Norma Lindsey Buchanan, Elizabeth Celia Sharkey, Daniel Latham Terrill, Steven Paul Bellner
  • Patent number: 6552217
    Abstract: Disclosed is a 4-step process for the preparation of alkyl esters of 1-methylcyclopropanecarboxylic acid which comprises the steps of (1) converting &ggr;-butyrolactone to &agr;-methyl-&ggr;-butyrolactone; (2) converting the &agr;-methyl-&ggr;-butyrolactone from step (1) to an alkyl 4-halo-2-methylbutyrate; (3) producing a xylene solution of the alkyl 4-halo-2-methylbutyrate; and (4) contacting the xylene solution of an alkyl 4-halo-2-methylbutyrate from step (3) with an alkali metal alkoxide under conditions of temperature and pressure which causes vaporization of (i) an alkanol as it is formed and (ii) an alkyl 1-methylcyclopropanecarboxylate as it is formed from the alkyl 4-halo-2-methylbutyrate. Also disclosed are processes whereby the alkyl 1-methylcyclopropanecarboxylate, prepared as described above, is converted to 1-methylcyclopropylamine.
    Type: Grant
    Filed: July 2, 2001
    Date of Patent: April 22, 2003
    Assignee: Eastman Chemical Company
    Inventors: John Clark Hubbs, David Carl Attride, Neil Warren Boaz, James Charles Ciula, John Thorton Maddox, Thomas Nabih, William Dell Nottingham, David Chris Spencer