Of Aldehyde Or Ketone Containing Compound Patents (Class 564/446)
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Patent number: 9962645Abstract: The invention relates to an absorbent solution for absorbing acid compounds, such as hydrogen sulfide and carbon dioxide, in a gaseous effluent, containing water and a mixture of amines comprising 1,2-bis-(2-dimethylaminoethoxy)-ethane and 2-[2-(2-dimethylaminoethoxy)-ethoxy]-ethanol, of respective formulas (I) and (II) below, and to a method of removing acid compounds contained in a gaseous effluent using this solution.Type: GrantFiled: May 12, 2015Date of Patent: May 8, 2018Assignee: IFP Energies nouvellesInventors: Bruno Delfort, Dominique Le Pennec, Julien Grandjean, Thierry Huard, Laetitia Giraudon, Aurelie Wender
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Patent number: 9233908Abstract: The instant invention provides cycloaliphatic diamines and a method of making the same. The cycloaliphatic diamines according to the instant invention comprise the reaction product of one or more cycloaliphatic cyanoaldehydes selected from the group consisting of 1,3-cyanocyclohexane carboxaldehyde, 1,4-cyanocyclohexane carboxaldehyde, mixtures thereof, and combinations thereof, hydrogen, and ammonia fed into a continuous reductive amination reactor system; wherein the one or more cycloaliphatic cyanoaldehydes, hydrogen, and ammonia are contacted with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80° C. to about 160° C. and a pressure in the range of from 700 to 3500 psig; and wherein one or more cycloaliphatic diamines are formed; and wherein said one or more cycloaliphatic diamines are selected from the group consisting of 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, combinations thereof, and mixtures thereof.Type: GrantFiled: July 30, 2010Date of Patent: January 12, 2016Assignee: Dow Global Technologies LLCInventors: Abraham D. Schuitman, Shawn D. Feist, Barry B. Fish, Daniel A. Hickman, Erich J. Molitor, Michael L. Tulchinsky
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Patent number: 9024072Abstract: A process for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines comprising (1) providing a mixture of 1,3-cyanocyclohexane carboxaldehyde and/or 1,4-cyanocyclohexane carboxaldehyde; (2) contacting said mixture with a metal carbonate based solid bed or a weak base anion exchange resin bed at a temperature from 15 to 40 ° C. for a period of at least 1 minute; (3) thereby treating said mixture, wherein said treated mixture has a pH in the range of 6 to 9; (4) feeding said treated mixture, hydrogen, and ammonia into a continuous reductive amination reactor system; (6) contacting said treated mixture, hydrogen, and ammonia with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature from 80 ° C. to 160 ° C. and a pressure from 700 to 3500 psig; (7) thereby producing one or more cycloaliphatic diamines is provided.Type: GrantFiled: July 30, 2010Date of Patent: May 5, 2015Assignee: Dow Global Technologies LLCInventors: Erich J. Molitor, Daniel A. Hickman, Shawn D. Feist, David C. Molzahn, Stacie Santhany, Abraham D. Schuitman
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Patent number: 8993819Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.Type: GrantFiled: July 10, 2012Date of Patent: March 31, 2015Assignee: BASF SEInventors: Joaquim Henrique Teles, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
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Patent number: 8877976Abstract: 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: GrantFiled: November 17, 2011Date of Patent: November 4, 2014Assignee: Evonik Degussa GmbHInventors: Christian Lettmann, Guido Streukens, Matthias Orschel, Gerda Grund
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Publication number: 20140296575Abstract: The present invention relates to a multi-branched Mannich base corrosion inhibitor and the method for preparing thereof. The method comprises (1) adding 3˜7 moles ketone and 3˜7 moles aldehyde to reaction kettle, adjusting pH to 2˜6 with acid, controlling temperature to 20˜50° C. and stirring for 20˜30 mins; (2) adding 1 mole organic polyamine to the reaction kettle under stirring, or adding the pH-adjusted ketone, aldehyde and organic solvent to organic polyamine, controlling temperature to 60˜90° C. and reacting for 1˜3 hrs, and after completion of the reaction, heating the system to 110° C. under nitrogen to remove water; the organic polyamine is organic compound comprising three or more primary amine groups and/or secondary amine groups.Type: ApplicationFiled: April 27, 2012Publication date: October 2, 2014Applicant: PetroChina Company LimitedInventors: Ling Ma, Lei Li, Xiangjun Kong, Malike Dilibai, Xinping Zhen, Chunge Niu, Shengjun Bai
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Publication number: 20140088321Abstract: A process for producing an aldehyde compound of the invention comprising: reacting a compound represented by the following formula (a1) or (a2) with a hydrogen and a carbon monoxide in a presence of a compound containing a metal belonging to Groups 8 to 10 and a phosphorous compound so as to satisfy the following conditions (1) and (2) to synthesize an aldehyde compound; wherein the condition (1) is that a content of a metal included in the compound containing a metal belonging to Groups 8 to 10 is 0.Type: ApplicationFiled: May 7, 2012Publication date: March 27, 2014Applicant: Mitsui Chemicals, Inc.Inventors: Shigetoshi Kuma, Michiharu Sakata, Kouichi Tokunaga, Chitoshi Shimakawa, Naoyuki Kakinuma, Masayuki Furuya, Mamoru Tanaka
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Patent number: 8592632Abstract: The present invention relates to a process for preparing a cyclic diamine, comprising the reaction of at least one cyclic alkene with a gas mixture (G) comprising dinitrogen the subsequent conversion of monoxide to give at least one cyclic ketone and then converting the at least one cyclic ketone to a cyclic diamine. The invention also relates to the use of a cyclic diamine with primary and secondary amine functions thus obtained to prepare polyamides and polyurethanes.Type: GrantFiled: November 6, 2009Date of Patent: November 26, 2013Assignee: BASF SEInventors: Kirsten Dahmen, Martin Ernst, Michael Limbach, Johann-Peter Melder, Beatrice Rössler-Feigel, Joaquim Henrique Teles
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Patent number: 8586794Abstract: The present invention relates to 5-isopropyl-3-aminomethyl-2-methyl-1-aminocyclohexane (carvonediamine) and to a process for preparation thereof by a) reacting carvone with hydrogen cyanide, b) then reacting the carvonenitrile obtained in stage a) with ammonia in the presence of an imine formation catalyst and c) then reacting the carvonenitrile imine-containing reaction mixture obtained in stage b) with hydrogen and ammonia over hydrogenation catalysts. The present invention further relates to the use of carvonediamine as a hardener for epoxy resins, as an intermediate in the preparation of diisocyanates, as a starter in the preparation of polyetherols and/or as a monomer for polyamide preparation.Type: GrantFiled: July 13, 2009Date of Patent: November 19, 2013Assignee: BASF SEInventors: Martin Ernst, Alfred Oftring, Kathrin Wissel-Stoll, Oemer Uensal, Stephan Freyer, Ansgar Gereon Altenhoff, Wolfgang Staffel
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Patent number: 8586793Abstract: Aldehyde or ketone compounds having more than one carbonyl group are reductively aminated to form a product amine compound having more than one primary amino group. The aldehyde or ketone compound is reacted with the product amine compound, to form a reaction mixture that contains one or more intermediates. The intermediate is then reductively aminated to form the desired product. This process produces the desired product in very high yields with low levels of secondary amine impurities.Type: GrantFiled: June 29, 2006Date of Patent: November 19, 2013Assignee: Dow Global Technologies LLCInventors: Michael Leo Tulchinsky, Barry B. Fish
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Patent number: 8461391Abstract: The present invention relates to a process for preparing N,N-substituted 1,3-propanediamine by a) reacting secondary amine with acrolein at a temperature of from (?50) to 100° C. and a pressure of from 0.01 to 300 bar, and b) reacting the reaction mixture obtained in stage a) with hydrogen and ammonia in the presence of a hydrogenation catalyst at a temperature of from 40 to 400° C. and a pressure of from 1 to 400 bar, wherein the molar ratio of secondary amine to acrolein in stage a) is 2:1 or more and the hydrogenation catalyst used in stage b) comprises cobalt. In a preferred embodiment, acrolein which has been obtained from glycerol based on renewable raw materials is used. The invention further relates to the use of N,N-dimethyl-1,3-propanediamine (DMAPA) based on renewable raw materials as a feedstock for lubricant soaps and other detergents, coagulants, polymers and comb polymers. In a further preferred embodiment, stage b) is performed in the presence of water.Type: GrantFiled: May 11, 2009Date of Patent: June 11, 2013Assignee: BASF SEInventors: Martin Ernst, Johann-Peter Melder, Christof Wilhelm Wigbers
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Patent number: 8450530Abstract: The present invention relates to a process for preparing unsymmetric secondary tert-butylamines by continuous amination in the gas phase, wherein tert-butylamine is converted over hydrogenation catalysts in the presence of an alcohol or aldehyde and hydrogen.Type: GrantFiled: April 6, 2011Date of Patent: May 28, 2013Assignee: BASF SEInventors: Christoph Mueller, Christof Wilhelm Wigbers, Johann-Peter Melder, Gerd Haderlein, Norbert Gutfrucht
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Patent number: 8445726Abstract: The present application relates to a process for preparing unsymmetric secondary tert-butylamines which, as well as the tert-butyl radical, also comprise an alkyl, cycloalkyl or benzyl radical. They are prepared by reacting corresponding aldehydes with tert-butylamine and hydrogen in the presence of hydrogenation catalysts (reductive amination) in the liquid phase.Type: GrantFiled: April 5, 2011Date of Patent: May 21, 2013Assignee: BASF SEInventors: Christof Wilhelm Wigbers, Christoph Mueller, Johann-Peter Melder, Bernd Stein, Harald Meissner, Gerd Haderlein, Norbert Gutfrucht
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Publication number: 20130018205Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.Type: ApplicationFiled: July 10, 2012Publication date: January 17, 2013Applicant: BASF SEInventors: Joaquim Henrique TELES, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
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Publication number: 20120142942Abstract: The invention disclosed in this document is related to the field of processes for the preparation of enamines wherein R1, R2, R3, R4, R5, and further information are disclosed herein.Type: ApplicationFiled: November 23, 2011Publication date: June 7, 2012Inventors: Douglas C. Bland, Todd W. Toyzan
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Publication number: 20120142943Abstract: The invention disclosed in this document is related to the field of processes for the preparation of enamines wherein R1, R2, R3, R4, R5, and further information are disclosed herein.Type: ApplicationFiled: November 23, 2011Publication date: June 7, 2012Applicant: DOW AGROSCIENCES LLCInventors: Douglas C. Bland, Todd W. Toyzan
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Publication number: 20120136173Abstract: The instant invention provides a process for improving catalytic activity of catalyst systems for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines. The process for improving catalytic activity of catalyst systems for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines comprises the steps of: (1) feeding ammonia, optionally hydrogen, and optionally one or more solvents over one or more heterogeneous metal based catalyst systems having a reduced catalytic activity for a period of greater than 1 hour at a temperature in the range of from 50° C. to 500° C.; wherein said one or more heterogeneous metal based catalyst systems have a yield of less than 90 percent based on the molar conversion of cyanoaldehydes to diamines; and (2) thereby improving the catalytic activity of said one or more heterogeneous metal based catalyst systems.Type: ApplicationFiled: July 30, 2010Publication date: May 31, 2012Applicant: Dow Global Technologies LLCInventors: Daniel A. Hickman, Shawn D. Feist, Erich J. Molitor, David C. Molzahn, Stacie Santhany, Abraham D. Schuitman
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Publication number: 20120129945Abstract: Compounds that are central nervous system drug candidates for the treatment of cognitive decline and, more particularly, Alzheimer's disease are provided. Methods of treating, inhibiting, and/or abatement of cognitive decline and/or Alzheimer's disease with a compound or pharmaceutically acceptable salt of the invention are also provided. Also provided are methods of preparing the compounds/compositions of the invention.Type: ApplicationFiled: August 2, 2010Publication date: May 24, 2012Applicant: Cognition Therapeutics, Inc.Inventors: Gilbert M. Rishton, Susan Catalano
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Publication number: 20120123165Abstract: The instant invention provides cycloaliphatic diamines and a method of making the same. The cycloaliphatic diamines according to the instant invention comprise the reaction product of one or more cycloaliphatic cyanoaldehydes selected from the group consisting of 1,3-cyanocyclohexane carboxaldehyde, 1,4-cyanocyclohexane carboxaldehyde, mixtures thereof, and combinations thereof, hydrogen, and ammonia fed into a continuous reductive amination reactor system; wherein the one or more cycloaliphatic cyanoaldehydes, hydrogen, and ammonia are contacted with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80° C. to about 160° C. and a pressure in the range of from 700 to 3500 psig; and wherein one or more cycloaliphatic diamines are formed; and wherein said one or more cycloaliphatic diamines are selected from the group consisting of 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, combinations thereof, and mixtures thereof.Type: ApplicationFiled: July 30, 2010Publication date: May 17, 2012Applicant: DOW GLOBAL TECHNOLOGIES LLCInventors: Abraham D. Schuitman, Shawn D. Feist, Barry B. Fish, Daniel A. Hickman, Erich J. Molitor, Michael L. Tulchinsky
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Publication number: 20120116123Abstract: The instant invention provides a process for separating one or more aliphatic diamines from reductive amination reaction solvents and impurities, and aliphatic diamines obtained via such a process. The process for separating one or more aliphatic diamines from reductive amination reaction solvents and impurities according to the instant invention comprises the steps of: (1) feeding one or more cycloaliphatic cyanoaldehydes, hydrogen, ammonia, and optionally one or more solvents into a continuous reductive amination reactor system; (2) contacting said one or more cycloaliphatic cyanoaldehydes, hydrogen, and ammonia with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80° C. to about 160° C.Type: ApplicationFiled: July 30, 2010Publication date: May 10, 2012Applicant: DOW GLOBAL TECHNOLOGIES LLCInventors: Stacie Santhany, Patrick Ho Sing Au-Yeung, Gerald W. Dare, Shawn D. Feist, Barry B. Fish, Daniel A. Hickman, David Jean, Erich J. Molitor, Abraham D. Schuitman, Todd William Toyzan
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Publication number: 20120116124Abstract: The instant invention provides a process for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines, and aliphatic diamines produced via such method. The process for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines comprises the steps of: (1) providing a mixture of one or more cycloaliphatic cyanoaldehydes, optionally water, and optionally one or more solvents, wherein said one or more cycloaliphatic cyanoaldehydes are selected from the group consisting of 1,3-cyanocyclohexane carboxaldehyde, 1,4-cyanocyclohexane carboxaldehyde, mixtures thereof, and combinations thereof; (2) contacting said mixture with a metal carbonate based solid bed or a weak base anion exchange resin bed at a temperature in the range of 15 to 40° C.Type: ApplicationFiled: July 30, 2010Publication date: May 10, 2012Applicant: Dow Global Technologies LLCInventors: Erich J. Molitor, Erich J. Molitor, Daniel A. Hickman, Shawn D. Feist, David C. Molzahn, Stacie Santhany, Abraham d. Schuitman
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Publication number: 20120065426Abstract: The present invention aims to provide a practical process for preparing amine compounds through a generalized highly-diastereoselective reductive amination reaction.Type: ApplicationFiled: September 14, 2011Publication date: March 15, 2012Applicant: Kanto Kagaku Kabushiki KaishaInventors: Masahito Watanabe, Kouichi Tanaka, Takashi Miki, Kunihiko Murata
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Patent number: 8034978Abstract: Process for preparing an amine by reacting an aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group consisting of primary and secondary amines in the presence of a heterogeneous catalyst, wherein the reaction is carried out using a suspended catalyst as heterogeneous catalyst and is carried out in the semibatch mode in which the nitrogen compound as one reactant is placed in the reaction vessel and the aldehyde and/or the ketone as the other reactant is added during the course of the reaction and the aldehyde and/or the ketone is added in portions or continuously to the reaction mixture during the course of the reaction as a function of the achieved conversion of the nitrogen compound until a conversion of the nitrogen compound of at least 95% results, and all or part of the catalyst remains in the reaction vessel after the reaction batch and is reused for the next reaction batch.Type: GrantFiled: May 24, 2007Date of Patent: October 11, 2011Assignee: BASF SEInventors: Jan Eberhardt, Harald Meiβner, Bram Willem Hoffer, Johann-Peter Melder, Ekkehard Schwab
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Publication number: 20110218323Abstract: The present invention relates to a process for preparing a cyclic diamine, comprising the reaction of at least one cyclic alkene with a gas mixture (G) comprising dinitrogen the subsequent conversion of monoxide to give at least one cyclic ketone and then converting the at least one cyclic ketone to a cyclic diamine. The invention also relates to the use of a cyclic diamine with primary and secondary amine functions thus obtained to prepare polyamides and polyurethanes.Type: ApplicationFiled: November 6, 2009Publication date: September 8, 2011Applicant: Basf SEInventors: Kirsten Dahmen, Martin Ernst, Michael Limbach, Johann-Peter Melder, Beatrice Rössler-Feigel, Joaquim Henrique Teles
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Patent number: 7985881Abstract: Compositions and methods relating to aromatic imine compounds and methods of their use are described. The compounds are formed from aromatic aldehydes and amino or amino derivatives. The compounds and their derivatives are useful, for example, as hydrogen sulfide and mercaptan scavengers for use in both water and petroleum products.Type: GrantFiled: September 12, 2007Date of Patent: July 26, 2011Assignee: Guard Products LLCInventors: Gary Westlund, David Weller
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Publication number: 20110124918Abstract: The present invention relates to 5-isopropyl-3-aminomethyl-2-methyl-1-aminocyclohexane (carvonediamine) and to a process for preparation thereof by a) reacting carvone with hydrogen cyanide, b) then reacting the carvonenitrile obtained in stage a) with ammonia in the presence of an imine formation catalyst and c) then reacting the carvonenitrile imine-containing reaction mixture obtained in stage b) with hydrogen and ammonia over hydrogenation catalysts. The present invention further relates to the use of carvonediamine as a hardener for epoxy resins, as an intermediate in the preparation of diisocyanates, as a starter in the preparation of polyetherols and/or as a monomer for polyamide preparation.Type: ApplicationFiled: July 13, 2009Publication date: May 26, 2011Applicant: BASF SEInventors: Martin Ernst, Alfred Oftring, Kathrin Wissel-Stoll, Oemer Uensal, Stephan Freyer, Ansgar Gereon Altenhoff, Wolfgang Staffel
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Publication number: 20100267948Abstract: Process for preparing an amine by reacting an aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group consisting of primary and secondary amines in the presence of a heterogeneous catalyst, wherein the reaction is carried out using a suspended catalyst as heterogeneous catalyst and is carried out in the semibatch mode in which the nitrogen compound as one reactant is placed in the reaction vessel and the aldehyde and/or the ketone as the other reactant is added during the course of the reaction and the aldehyde and/or the ketone is added in portions or continuously to the reaction mixture during the course of the reaction as a function of the achieved conversion of the nitrogen compound until a conversion of the nitrogen compound of at least 95% results, and all or part of the catalyst remains in the reaction vessel after the reaction batch and is reused for the next reaction batch.Type: ApplicationFiled: May 24, 2007Publication date: October 21, 2010Applicant: BASF SEInventors: Jan Eberhardt, Harald Meissner, Bram Willem Hoffer, Johann-Peter Melder, Ekkehard Schwab
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Publication number: 20100234596Abstract: [Problem] The present invention aims to provide a novel organometallic compound that can be used as a general-use highly active catalyst with superior selectivity for functional groups. [Means for Solving Problem] The present invention relates to an organometallic compound having a novel specific structure of general formula (1): and to a general-use highly active catalyst used in reductive amination reaction with superior selectivity for functional groups that comprises said organometallic compound, and to a process for preparing amine compounds by reductive amination reaction using said catalyst.Type: ApplicationFiled: March 12, 2010Publication date: September 16, 2010Applicant: Kanto Kagaku Kabushiki KaishaInventors: Masahito Watanabe, Junichi Hori, Kunihiko Murata
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Publication number: 20100222611Abstract: Aldehyde or ketone compounds having more than one carbonyl group are reductively aminated to form a product amine compound having more than one primary amino group. The aldehyde or ketone compound is reacted with the product amine compound, to form a reaction mixture that contains one or more intermediates. The intermediate is then reductively aminated to form the desired product. This process produces the desired product in very high yields with low levels of secondary amine impurities.Type: ApplicationFiled: June 29, 2006Publication date: September 2, 2010Inventors: Michael Leo Tulchinsky, Barry B. Fish
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Publication number: 20090082562Abstract: A process for preparing an amine by reacting an aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group of primary and secondary amines in the presence of a heterogeneous catalyst, wherein the catalyst is a coated catalyst which comprises at least one metal of group VIII of the Periodic Table of the Elements as a hydrogenating metal and additionally a promoter on an oxidic support, at least 80% of the metal of group VIII of the Periodic Table of the Elements being present in a layer between the surface of the catalyst and a penetration depth which is not more than 80% of the radius of the catalyst, calculated from the surface of the catalyst.Type: ApplicationFiled: March 13, 2007Publication date: March 26, 2009Applicant: BASF SEInventors: Jan Eberhardt, Bram Willem Hoffer, Frank Haese, Johann-Peter Melder, Bernd Stein, Michael Stang, Thomas Hill, Ekkehard Schwab
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Patent number: 7405327Abstract: Process for the continuous preparation of an amine by reaction of a primary or secondary alcohol, aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group consisting of ammonia, primary and secondary amines at a temperature in the range from 60 to 300° C.Type: GrantFiled: May 4, 2005Date of Patent: July 29, 2008Assignee: BASF AktiengesellschaftInventors: Frank Haese, Arnd Bottcher, Bernd Stein, Wolfgang Reif, Johann-Peter Melder, Karl-Heinz Roβ, Heinz Rutter, Shelue Liang, Stefan Rittinger
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Patent number: 7405324Abstract: 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: GrantFiled: May 10, 2006Date of Patent: July 29, 2008Assignee: A.M.S.A. Anonima Materie Sintetiche E. Afini S.p.A.Inventors: Enrico Vigano′, Ernesto Landonio, Simona Lanfranconi, Renato Molteni
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Publication number: 20080167499Abstract: Aldehyde or ketone compounds having more than one carbonyl group are reductively aminated to form a product amine compound having more than one primary amino group. The aldehyde or ketone compound is reacted with the product amine compound in the presence of an alcohol solvent, to form a reaction mixture that contains one or more intermediates. The intermediate is then reductively aminated to form the desired product. This process may produce the desired product in very high yields with low levels of secondary amine impurities.Type: ApplicationFiled: December 14, 2007Publication date: July 10, 2008Applicant: DOW GLOBAL TECHNOLOGIES INC.Inventors: Erich J. Molitor, Todd W. Toyzan
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Patent number: 7342135Abstract: 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: GrantFiled: January 25, 2007Date of Patent: March 11, 2008Assignee: Celanese Chemicals Europe GmbHInventors: Helmut Springer, Paolo Bavaj
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Patent number: 7321068Abstract: Process for preparing tricyclodecanedialdehyde by hydroformylation of dicyclopentadiene by means of a CO/H2 mixture at elevated temperature and under superatmospheric pressure in the presence of a rhodium catalyst which has not been modified by means of a ligand and is homogeneously dissolved in the hydroformylation medium, wherein the hydroformylation is carried out at a pressure of from 200 to 350 bar in at least two reaction zones, with a reaction temperature of from 80 to 120° C. being set in a first reaction zone and a reaction temperature of from 120 to 150° C. being set in a reaction zone following this reaction zone, with the proviso that the reaction temperature in the subsequent reaction zone is at least 5° C. higher than in the preceding reaction zone.Type: GrantFiled: December 14, 2004Date of Patent: January 22, 2008Assignee: BASF AktiengesellschaftInventors: Rainer Papp, Rocco Paciello, Christoph Benisch
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Patent number: 7317128Abstract: A process for preparing 3(4),8(9)-bis(aminomethyl)tricycle-[5.2.1.02,6]decane by hydroformylating dicyclopentadiene with subsequent reductive amination wherein the hydroformylation of dicyclopentadiene is carried out in two stages, and, in a first hydroformylation stage, the reaction is effected in a heterogeneous reaction system using an aqueous solution of transition metal compounds, containing water-soluble organic phosphorus (III) compounds in complex-bound form, of group VIII of the Periodic Table to give 8(9)-formyltricyclo[5.2.1.02,6]dec-3-ene, and, in a second hydroformylation stage, the thus obtained 8(9)-formyltricyclo[5.2.1.02,6]dec-3-ene is converted, in a homogeneous organic phase in the presence of transition metal compounds of group VIII of the Periodic Table of the Elements to 3(4),8(9)-bisformyltricyclo[5.2.1.Type: GrantFiled: October 18, 2004Date of Patent: January 8, 2008Assignee: Oxea Deutschland GmbHInventors: Peter Lappe, Helmut Springer, Rainer Lukas
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Publication number: 20070179319Abstract: 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: ApplicationFiled: January 25, 2007Publication date: August 2, 2007Inventors: Helmut Springer, Paolo Bavaj
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Patent number: 6900355Abstract: 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: GrantFiled: March 5, 2004Date of Patent: May 31, 2005Assignee: Ciba Specialty Chemicals CorporationInventors: Heinz Steiner, Marc Thommen, Hans-Peter Jalett, Markus Benz
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Patent number: 6884887Abstract: The invention relates to the preparation of chiral or achiral amines by reaction of aldehydes or ketones with ammonia or primary or secondary amines in the presence of hydrogen and in the presence of homogeneous metal catalysts under mild conditions. Metal catalysts which can be used are complexes of late transition metals with chiral or achiral phosphorus-containing ligands.Type: GrantFiled: June 29, 2000Date of Patent: April 26, 2005Assignee: Degussa AGInventors: Thomas Riermeier, Karl-Josef Haack, Uwe Dingerdissen, Armin Boerner, Vitali Tararov, Renat Kadyrov
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Publication number: 20040171883Abstract: 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: ApplicationFiled: March 5, 2004Publication date: September 2, 2004Inventors: Heinz Steiner, Marc Thommen, Hans-Peter Jalett, Markus Benz
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Publication number: 20040171882Abstract: The present invention provides a process for the preparation of a bicyclic aminoalcohol which comprises reacting a starting compound, nopinone (I), with XCH2COOR1 wherein X is halogen, and R1 is alkyl, in the presence of an additive and a base to produce a compound (II), converting it to oxime derivative (III), and reducing it with an aluminum hydride.Type: ApplicationFiled: February 25, 2004Publication date: September 2, 2004Inventors: Tsunetoshi Honma, Yoshiharu Hiramatsu, Susumu Mitsumori
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Patent number: 6710210Abstract: 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: GrantFiled: April 8, 2002Date of Patent: March 23, 2004Assignee: Daicel Chemical Industries, Ltd.Inventors: Hiroki Tanaka, Li Rui Pan, Kiyoshi Ikura
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Publication number: 20040015016Abstract: Disclosed herein is a process for the reductive alkylation of primary amines to form secondary amines, by high pressure reaction of the primary amine with an alkylating agent and hydrogen in the presence of a catalyst which comprises metallic palladium. A process of the present invention is characterized in having high conversion rates and high selectivities, both greater than 95% on a first pass through the reactor. According to a preferred embodiment, the secondary amine produced comprises at least one 2-alkyl group bonded to the nitrogen atom of the primary amine product.Type: ApplicationFiled: July 22, 2002Publication date: January 22, 2004Applicant: Huntsman Petrochemical CorporationInventors: Wei-Yaug Su, Christopher H. Nelli
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Patent number: 6525222Abstract: Amines are prepared by reacting aldehydes or ketones at elevated temperature under elevated pressure with nitrogen compounds selected from the group of ammonia, primary and secondary amines, and with hydrogen in the presence of a catalyst, wherein the catalytically active mass of the catalyst contains, after its preparation and before the treatment with hydrogen, 22 to 45% by weight of oxygen-containing compounds of zirconium, calculated as ZrO2, 1 to 30% by weight of oxygen-containing compounds of copper, calculated as CuO, 5 to 50% by weight of oxygen-containing compounds of nickel, calculated as NiO, where the molar ratio of nickel to copper is greater than 1, 5 to 50% by weight of oxygen-containing compounds of cobalt, calculated as CoO, 0 to 5% by weight of oxygen-containing compounds of molybdenum, calculated as MoO3, and 0 to 10% by weight of oxygen-containing compounds of aluminum and/or manganese, calculated as Al2O3 or MnO2.Type: GrantFiled: December 5, 2000Date of Patent: February 25, 2003Assignee: BASF AktiengesellschaftInventors: Jan Nouwen, Arthur Höhn, Horst Neuhauser, Frank Funke, Stephan Andreas Schunk, Johann-Peter Melder, Knut Eger, Michael Hesse, Joachim Wulff-Döring
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Publication number: 20020156323Abstract: Novel N-substituted-aminomethyl cyclopropyl ketone derivatives are represented by following Formula (1): 1Type: ApplicationFiled: April 8, 2002Publication date: October 24, 2002Inventors: Hiroki Tanaka, Li Rui Pan, Kiyoshi Ikura
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Patent number: 6448445Abstract: The invention relates to a method for disubstituting carboxylic acid amides on the geminal carbonyl-C-atom using at least one grignard reagent in the presence of a metal alcoholate compound used as a catalyst and in the presence of another organometallic compound used as a co-catalyst.Type: GrantFiled: February 23, 2001Date of Patent: September 10, 2002Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Herwig Buchholz, Urs Welz-biermann, Armin Meijere
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Patent number: 6340772Abstract: Three processes are described for preparing (hetero)aromatic substituted benzene derivatives which comprise aromatization of cyclohexenone derivatives via (chloro)cyclohexadiene derivatives.Type: GrantFiled: April 24, 2001Date of Patent: January 22, 2002Assignee: Nippon Kayaku Co., Ltd.Inventors: Tetsuya Toya, Hidetoshi Shirakura, Junichi Kon
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Patent number: 6323370Abstract: The present invention relates to methods for the reductive amination of a carbonyl-containing compound. R1R2CO where R1 and R2 are either H, alkyl, aryl or heterocyclic etc with an amine NHR3R4 where R3 and R4 arm H, alkyl, aryl, or heterocyclic in the presence of a homogeneous iridium catalyst and gaseous hydrogen.Type: GrantFiled: August 25, 2000Date of Patent: November 27, 2001Assignee: Johnson Matthey Public Limited CompanyInventors: Penelope Ann Chaloner, Simon Collard, Richard David Ellis, Ann Kathleen Keep
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Patent number: 6271418Abstract: Three processes are described for preparing (hetero)aromatic substituted benzene derivatives which comprise aromatization of cyclohexenone derivatives via (chloro)cyclohexadiene derivatives.Type: GrantFiled: February 22, 2000Date of Patent: August 7, 2001Assignee: Nippon Kayaku Co., Ltd.Inventors: Tetsuya Toya, Hidetoshi Shirakura, Junichi Kon
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Publication number: 20010003136Abstract: Amines are prepared by reacting aldehydes or ketones at elevated temperature under elevated pressure with nitrogen compounds selected from the group of ammonia, primary and secondary amines, and with hydrogen in the presence of a catalyst, wherein the catalytically active mass of the catalyst contains, after its preparation and before the treatment with hydrogen, 22 to 45% by weight of oxygen-containing compounds of zirconium, calculated as ZrO2,Type: ApplicationFiled: December 5, 2000Publication date: June 7, 2001Inventors: Jan Nouwen, Arthur Hohn, Horst Neuhauser, Frank Funke, Stephan Andreas Schunk, Johann-Peter Melder, Knut Eger, Michael Hesse, Joachim Wulff-Doring