Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/814)
  • Publication number: 20120046479
    Abstract: The present disclosure relates to a method for preparing a metal catalyst comprising at least one ligand that is coordinated to the metal through at least one phosphorous (P) atom and at least one nitrogen (N) atom, the method comprising reacting a metal pre-cursor complex with an acid ad salt of an aminophosphine, diaminophosphine, aminodiphosphine or diaminodiphosphine, in the presence of a base.
    Type: Application
    Filed: October 8, 2009
    Publication date: February 23, 2012
    Inventors: Kamaluddin Abdur-Rashid, Dino Amoroso, Xuanhua Chen, Rongwei Guo, Shuiming Lu, Chi-Wing Tsang
  • Publication number: 20120029195
    Abstract: A method for producing an alcohol compound, wherein a carboxylic acid ester compound is reduced with hydrogen in the presence of a ruthenium complex which is obtained by reacting a pyridine compound having at least one optionally substituted amino group with a ruthenium compound.
    Type: Application
    Filed: March 30, 2010
    Publication date: February 2, 2012
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Yasutaka Aoyagi, Hiroshi Souda, Koji Hagiya
  • Publication number: 20120010417
    Abstract: A method for producing an alcohol compound, wherein a carboxylic acid ester compound is reduced with hydrogen in the presence of a ruthenium complex which is obtained by reacting an imidazolium salt (A) having at least one optionally substituted amino group with a ruthenium compound (B) in the presence of a base (C).
    Type: Application
    Filed: March 29, 2010
    Publication date: January 12, 2012
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Koji Hagiya, Yasutaka Aoyagi
  • Publication number: 20110282077
    Abstract: The object of the present invention is to solve the problems in the prior arts, and to find more improved reaction conditions for suppressing the racemization of the product and obtaining an optically active alcohol at a high optical purity. The inventors achieved to solve the above problems by using a solvent system that is capable of resolving both an asymmetric catalyst and a formate salt, allowing the hydrogen source and the asymmetric catalyst to be present in the same phase.
    Type: Application
    Filed: May 10, 2011
    Publication date: November 17, 2011
    Applicant: Kanto Kagaku Kabushiki Kaisha
    Inventors: Taito Hatakeyama, Kunihiko Murata, Kunihiko Tsutsumi, Noriyuki Utsumi
  • Patent number: 8044245
    Abstract: Optically active 2-sulfonyloxy-1-phenylethanol derivative of formula (II) can be prepared easily and selectively by the method of the present invention using an asymmetric reduction of an ?-sulfonyloxy acetophenone compound with a rhodium catalyst having petamethylcyclopentadienyl group and a hydrogen donor, and the compound of formula (II) obtained in the inventive method exhibits a higher e.e. (enantiomer excess) value than that of the products in the conventional methods.
    Type: Grant
    Filed: November 1, 2007
    Date of Patent: October 25, 2011
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kee-In Lee, Do-Min Lee
  • Publication number: 20110237814
    Abstract: The present invention relates to a ruthenium carbonyl complex that is represented by the following Formula (1): RuXY(CO)(L)??(1) (in the Formula (1), X and Y, which may be the same or different from each other, represent an anionic ligand and L represents a tridentate aminodiphosphine ligand which has two phosphino groups and a —NH— group), its production method, and a method for production of alcohols by hydrogenation-reduction of ketones, esters, and lactones using the complex as a catalyst. The ruthenium carbonyl complex of the invention has a high catalytic activity and it can be easily prepared and handled.
    Type: Application
    Filed: June 30, 2010
    Publication date: September 29, 2011
    Applicant: Takasago International Corporation
    Inventors: Wataru Kuriyama, Takaji Matsumoto, Yasunori Ino, Osamu Ogata
  • Patent number: 8013193
    Abstract: Disclosed is a method for producing an alcohol from a lactone or a carboxylic acid ester, which enables to produce an alcohol from a lactone or a carboxylic acid ester under relatively mild conditions with high yield and high catalytic efficiency. This method also enables to produce an optically active alcohol from an optically active lactone or an optically active carboxylic acid ester. Specifically disclosed is a method for producing an alcohol by hydrogen reducing a lactone or a carboxylic acid ester in the presence of a catalyst containing ruthenium and a phosphine compound represented by the following general formula (1): wherein R1 represents a spacer; R2, R3, R4, R5, R6 and R7 independently represent a hydrogen atom, an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group; and R8, R9, R10, R11, R12 and R13 independently represent an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group.
    Type: Grant
    Filed: April 2, 2008
    Date of Patent: September 6, 2011
    Assignees: Kaneka Corporation, Takasago International Corporation
    Inventors: Hirofumi Maeda, Kenji Inoue, Takaji Matsumoto, Izuru Nagasaki, Ryoji Noyori, Susumu Saito
  • Publication number: 20110207968
    Abstract: The present invention relates to a process for preparing 4-isopropylcyclohexylmethanol (IPCHM) from para-cymene. The process for preparing 4-isopropylcyclohexylmethanol (IPCHM) comprises an electrochemical process for preparing a mixture of 4-isopropylbenzaldehyde dimethyl acetal and 4-(1-alkoxy-1-methylethyl)benzaldehyde dimethyl acetal, and intermediates passed through in the process, a hydrolysis step to form the corresponding benzaldehydes and a hydrogenation of this mixture to form 4-isopropylcyclohexylmethanol (IPCHM).
    Type: Application
    Filed: February 11, 2011
    Publication date: August 25, 2011
    Applicant: BASF SE
    Inventors: Florian Stecker, Ulrich Griesbach, Martin Bock, Lucia Königsmann
  • Publication number: 20110201847
    Abstract: A method for the production of nanocrystalline nickel oxides as well as the nickel oxides produced by the method according to the invention and the use thereof as catalyst following reduction to nickel metal, in particular for hydrogenation reactions.
    Type: Application
    Filed: May 29, 2009
    Publication date: August 18, 2011
    Inventors: Hans-Jörg Wölk, Alfred Hagemeyer, Frank Grossmann, Silvia Neumann
  • Publication number: 20110201820
    Abstract: Disclosed is a practical method for efficiently producing an alcohol compound by hydrogenating an aldehyde by using a homogeneous copper catalyst which is an easily-available low-cost metal species. Specifically disclosed is a method for producing an alcohol compound, which is characterized in that a hydrogenation reaction of an aldehyde compound is performed in the presence of a homogeneous copper catalyst, a monophosphine compound and an alcohol selected from the group consisting of primary alcohols, secondary alcohols and mixtures of those.
    Type: Application
    Filed: December 11, 2008
    Publication date: August 18, 2011
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventor: Hideo Shimizu
  • Publication number: 20110201819
    Abstract: Disclosed is a practical method for efficiently producing an alcohol compound by hydrogenating an aldehyde by using a homogeneous copper catalyst which is an easily-available low-cost metal species. Specifically disclosed is a method for producing an alcohol compound, which is characterized in that a hydrogenation reaction of an aldehyde compound is performed in the presence of a homogeneous copper catalyst and a diphosphine compound.
    Type: Application
    Filed: December 11, 2008
    Publication date: August 18, 2011
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventor: Hideo Shimizu
  • Publication number: 20110190523
    Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of specific ruthenium catalysts or pre-catalysts in hydrogenation processes for the reduction of ketones, aldehydes, esters or lactones into their corresponding alcohols or diols respectively. The preferred catalysts are ruthenium complexes comprising a ligand of the type (N—N) type and a ligand of the type (P—PO).
    Type: Application
    Filed: October 1, 2009
    Publication date: August 4, 2011
    Inventors: Lionel Saudan, Christophe Saudan, Michel Alfred Jose Saudan, Sylvia Joyeuse Adélaïde Ada Saudan
  • Patent number: 7973201
    Abstract: A process for the production of a halogen-substituted benzenedimethanol represented by the formula (2): wherein X1, X2, X3 and X4 are the same or different and independently represent a hydrogen atom or a halogen atom, provided that at least one of X1, X2, X3 and X4 represents a halogen atom, comprising reacting a halogen-substituted terephthalic acid diester represented by the formula (1): wherein X1, X2, X3 and X4 are the same meanings as defined above and R1 and R2 are the same or different and independently represent an unsubstituted or substituted alkyl group, a metal borohydride compound and an acid in the presence of an ether solvent, wherein the amount of the acid is 0.2 to 3 moles per 1 mole of the metal borohydride compound based on protons, and the reaction is conducted under the condition where the liquid phase of the reaction mixture is a single layer.
    Type: Grant
    Filed: June 21, 2007
    Date of Patent: July 5, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Koji Hagiya
  • Patent number: 7956182
    Abstract: This invention relates to a process for producing optically active alcohols using asymmetric reduction of aromatic ketones. This process gives optically active alcohols in high enantioselectivity in a large scale production.
    Type: Grant
    Filed: February 13, 2007
    Date of Patent: June 7, 2011
    Assignee: Kotobuki Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Tomiyama, Masayuki Yokota
  • Patent number: 7956223
    Abstract: A method for producing a halogen-substituted benzenedimethanol represented by the formula (2): wherein X1, X2, X3 and X4 are the same or different and each independently represent a hydrogen atom or a halogen atom, provided that X1, X2, X3 and X4 are not hydrogen atoms at the same time, by reacting a halogen-substituted terephthalic acid represented by the formula (1): wherein X1, X2, X3 and X4 are the same meanings as defined above, with a borohydride compound in an organic solvent, followed by contacting the obtained reaction mixture with hydrogen chloride at 40 to 70° C.
    Type: Grant
    Filed: January 16, 2007
    Date of Patent: June 7, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Koji Hagiya
  • Patent number: 7939695
    Abstract: The present invention provides an industrially advantageous process for preparing nucleus-halogenated methylbenzyl alcohol which is a useful substance as a raw material, an intermediate for manufacturing medicines, agricultural chemicals, etc. The process of the present invention for preparing nucleus-halogenated methylbenzyl alcohol represented by the following formula (II) includes hydrogenating nucleus-halogenated benzene dicarbaldehyde represented by the following formula (I); wherein m is an integer of 0 to 3, and n is an integer of 1 to 4, with the proviso that m+n is an integer of 1 to 4, wherein m and n are the same as those in the formula (I).
    Type: Grant
    Filed: June 12, 2006
    Date of Patent: May 10, 2011
    Assignee: Showa Denko K.K.
    Inventors: Haruhiko Ikeda, Hideo Miyata
  • Publication number: 20110105693
    Abstract: Disclosed are cationic ruthenium arene complexes of Formula (I): [Ru(D-Z1—NHR1)(Ar)(LB)n]r+[Y?]r, wherein Ar is optionally substituted aryl, D-Z1—NHR1 is a coordinated bidentate ligand wherein D, Z1, R1 and R2 are as defined herein, and where R1 and Ar, or R2 and Ar may be linked together, n is 0 or 1, r is 1 or 2, LB is a neutral Lewis base, and Y is a non-coordinating anion. The complexes are active catalysts for reduction reactions, including the transfer-hydrogenation of carbon-oxygen (C?O) and carbon-nitrogen (C?N) double bonds.
    Type: Application
    Filed: May 1, 2009
    Publication date: May 5, 2011
    Applicant: KANATA CHEMICAL TECHNOLOGIES INC.
    Inventors: Kamaluddin Abdur-Rashid, Dino Amoroso, Christine Sui-Seng, Wenli Jia, Charles Ewart
  • Publication number: 20110092747
    Abstract: Esters and lactones can be respectively reduced to alcohols and diols in the presence of the Group 8 (VIII) transition metal complex, base and hydrogen gas (H2). An extremely practical reduction method can be provided by preferable combinations of the Group 8 (VIII) transition metal complex, the base, a used amount of the base, a pressure of hydrogen gas and a reaction temperature. This method is used in place of hydride reduction and is a useful method by which design of highly active catalysts can be relatively easily made while a high productivity can be expected.
    Type: Application
    Filed: June 26, 2009
    Publication date: April 21, 2011
    Applicants: TOKYO INSTITUTE OF TECHNOLOGY, CENTRAL GLASS COMPANY, LIMITED
    Inventors: Takao Ikariya, Masato Ito, Akira Shiibashi, Takashi Ootsuka
  • Publication number: 20110065929
    Abstract: Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.
    Type: Application
    Filed: November 18, 2010
    Publication date: March 17, 2011
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Hideo SHIMIZU, Daisuke IGARASHI, Wataru KURIYAMA, Yukinori YUSA
  • Patent number: 7884223
    Abstract: The invention relates to an enantiomerically enriched chiral compound comprising a transition metal M, which comprises four, five or six coordinating groups of which at least one pair is linked together to form a bidentate ligand, in which M is directly bound via one single ?-bond to a carbon atom of an optionally substituted and/or optionally fused (hetero)aromatic ring of said bidentate ligand and in which M is directly bound to a nitrogen atom of a primary or secondary amino group of said bidentate ligand, thereby forming a metallacycle between said bidentate ligand and the metal M, said metal M being selected from the metals of groups 8 and 9 of the Periodic Table of the Elements, in particular iron, ruthenium, osmium, cobalt, rhodium, or iridium. The chiral compound can be used as a catalyst, preferably in an asymmetric transfer hydrogenation process.
    Type: Grant
    Filed: November 10, 2005
    Date of Patent: February 8, 2011
    Assignee: DSM IP Assets B.V.
    Inventors: Johannes Gerardus (Hans) De Vries, Gerardus Karel Maria Verzijl, Andreas Hendrikus Maria De Vries, Vincent Ritleng, Adeline Marie Joseèphe Voelklin
  • Publication number: 20110009646
    Abstract: There are provided a novel ruthenium-diamine complex, and methods for selectively producing an optically active alcohol and an optically active amine, which are important as precursors for the synthesis of medicinal drugs and functional materials, using the ruthenium-diamine complex as a catalyst. A novel ruthenium-diamine complex prepared by introducing a trisubstituted silyl group into an aromatic compound (arene) moiety that is coordinated with a ruthenium complex having an optically active diamine as a ligand, a catalyst for asymmetric reduction formed from the ruthenium-diamine complex, and a method for producing an optically active alcohol or an optically active amine using the catalyst.
    Type: Application
    Filed: July 13, 2010
    Publication date: January 13, 2011
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Taichiro Touge, Hideki Nara
  • Patent number: 7858831
    Abstract: This invention is directed to a method of performing a stereoselective reaction without use of a solvent comprising contacting a reactant with a chiral reagent under sonication conditions to form an excess of an enantiomer.
    Type: Grant
    Filed: December 19, 2008
    Date of Patent: December 28, 2010
    Assignee: The Regents of the University of California
    Inventors: Matthew P. Meyer, Hui Zhu
  • Publication number: 20100311975
    Abstract: The present disclosure includes catiome complexes of iron, ruthenium, and osmium, and their use as catalysts in organic synthesis transformations including the hydrogenation of unsaturated compounds. The complexes are represented by the following formulae I, II, III, IV, and V, wherein M is Fe, Ru or Os, P is a monodentate ligand with a phosphorus donor atom, P2 is a bidentate neutral ligand with two phosphorus donor atoms, N2 is a bidentate neutral ligand with two nitrogen donor atoms, PN is a bidentate neutral ligand with phosphorus and nitrogen donor atoms, PNNP is a tetradentate neutral ligand bonded to M via two phosphorus and two nitrogen atoms, X is any anionic ligand, LB is any neutral Lewis base, Y is any non-coordinating anion, n is 0, 1, or 2, m is 1 or 2, q is 0 or 1, r is 1 or 2 and q+r=2.
    Type: Application
    Filed: October 30, 2008
    Publication date: December 9, 2010
    Inventors: Kamaluddin Abdur-Rashid, Dino Amoroso, Rongwei Guo, Xuanhua Chen, Christine Sui-Seng, Chi-Wing Tsang, Wenli Jia
  • Publication number: 20100286401
    Abstract: Disclosed are iron ligand catalysts for selective hydrogenation of aldehydes, ketones and imines. A catalyst such as dicarbonyl iron hydride hydroxycyclopentadiene) complex uses the OH on the five member ring and hydrogen linked to the iron to facilitate hydrogenation reactions, particularly in the presence of hydrogen gas.
    Type: Application
    Filed: November 20, 2007
    Publication date: November 11, 2010
    Inventors: Charles P. Casey, Hairong Guan
  • Publication number: 20100286452
    Abstract: The present invention relates to processes for the reduction by hydrogenation, using molecular H2, of a substrate containing one or two esters, or lactones, functional groups into the corresponding alcohol, or diol, with the process being carried out in the presence of a base and at least one catalyst or pre-catalyst in the form of a ruthenium complex, wherein the ruthenium is coordinated by a diphosphine bidentate ligand (PP ligand) and a diamino bidentate ligand (NN ligand) that includes at least one substituted ?-carbon and one primary amine as one of the coordinating atoms.
    Type: Application
    Filed: November 22, 2007
    Publication date: November 11, 2010
    Inventors: Lionel Saudan, Christophe Saudan, Michel Alfred Joseph Saudan, Sylvia Joyeuse Adelaide Ada Saudan
  • Publication number: 20100280273
    Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of Ru complexes with bidentate ligands, having one amino or imino coordinating group and one phosphino coordinating group, in hydrogenation processes for the reduction of esters or lactones into the corresponding alcohol or diol respectively.
    Type: Application
    Filed: July 20, 2010
    Publication date: November 4, 2010
    Inventors: Lionel Saudan, Philippe Dupau, Jean-Jacques Riedhauser, Patrick Wyss
  • Publication number: 20100261924
    Abstract: The present invention provides an organic metal compound, a ligand, an asymmetric catalyst, and a process for preparing optically-active alcohols using the asymmetric catalyst.
    Type: Application
    Filed: April 12, 2010
    Publication date: October 14, 2010
    Applicant: Kanto Kagaku Kabushiki Kaisha
    Inventors: Masahito Watanabe, Junichi Hori
  • Patent number: 7807856
    Abstract: A process for producing a 2-benzylphenol compound represented by the following formula (2): wherein, R1, R2, R3 and R4 may be the same or different and are each independently hydrogen atom, alkyl group or the like; and R5, R6, R7, R8 and R9 are the same or different and are each independently hydrogen atom, alkyl group or the like, the process including reacting, in the presence of a dehydrogenating agent, a benzylidenecyclohexanone compound represented by the following formula (1): wherein, R1, R2, R3, R4, R5, R6, R7, R8 and R9 have the same definitions as given above.
    Type: Grant
    Filed: November 7, 2005
    Date of Patent: October 5, 2010
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Kentaro Kawazoe, Yasuo Yoshida
  • Patent number: 7795478
    Abstract: A fluorine-containing benzaldehyde is reacted with an alkyl Grignard reagent to convert it to a magnesium alkoxide of racemic, fluorine-containing, benzyl alcohol, and subsequently the magnesium alkoxide is reacted with phthalic anhydride to obtain a phthalate half ester of racemic, fluorine-containing, benzyl alcohol, and the half ester is optically resolved by optically active 1-phenylethylamine, and then the ester group is hydrolyzed, thereby producing an optically active, fluorine-containing, benzyl alcohol.
    Type: Grant
    Filed: October 4, 2006
    Date of Patent: September 14, 2010
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Koji Ueda, Manabu Yasumoto
  • Patent number: 7777083
    Abstract: A process for the reduction of compounds comprising one or more carbon-oxygen (C?0) double bonds, to provide the corresponding alcohol, comprising contacting the compound with hydrogen gas at a pressure greater than 3 atm and a catalyst comprising an iridium aminodiphosphine complex.
    Type: Grant
    Filed: May 30, 2008
    Date of Patent: August 17, 2010
    Assignee: Kanata Chemical Technologies Inc.
    Inventors: Kamaluddin Abdur-Rashid, Rongwei Guo, Xuanhua Chen, Wenli Jia
  • Patent number: 7772445
    Abstract: The present disclosure relates to a process for the hydrogenation of compounds comprising one or more carbon-oxygen (C?O) double bonds, to provide the corresponding alcohol, comprising contacting the compound with hydrogen gas at and a catalyst comprising a ruthenium-aryl-aminophosphine complex.
    Type: Grant
    Filed: July 7, 2008
    Date of Patent: August 10, 2010
    Assignee: Kanata Chemical Technologies Inc.
    Inventors: Xuanhua Chen, Wenli Jia, Kamaluddin Abdur-Rashid, Rongwei Guo
  • Publication number: 20100197976
    Abstract: Catalysts suitable for asymmetric hydrogenation reactions is described comprising the reaction product of a group 8 transition metal compound a chiral phosphine and a chiral diamine of formula (I) in which R1, R2, R3 and R4 are independently hydrogen, a saturated or unsaturated alkyl or cycloalkyl group, an aryl group or a urethane or sulphonyl group and R5, R6, R7 and R8 are independently hydrogen, a saturated or unsaturated alkyl or cycloalkyl group, or an aryl group, at least one of R1, R2, R3 and R4 is hydrogen and A is a linking group comprising one or two substituted or unsubstituted carbon atoms.
    Type: Application
    Filed: January 29, 2010
    Publication date: August 5, 2010
    Applicant: Johnson Matthey PLC
    Inventors: William Patrick Hems, Gabriela Alexandra Grasa
  • Patent number: 7763758
    Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of Ru complexes with bidentate ligands, having one amino or imino coordinating group and one phosphino coordinating group, in hydrogenation processes for the reduction of esters or lactones into the corresponding alcohol or diol respectively.
    Type: Grant
    Filed: September 12, 2007
    Date of Patent: July 27, 2010
    Assignee: Firmenich SA
    Inventors: Lionel Saudan, Philippe Dupau, Jean-Jacques Riedhauser, Patrick Wyss
  • Publication number: 20100168440
    Abstract: Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.
    Type: Application
    Filed: February 9, 2010
    Publication date: July 1, 2010
    Applicant: Takasago International Corporation
    Inventors: Hideo SHIMIZU, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
  • Publication number: 20100145106
    Abstract: The present invention provides an industrially advantageous process for preparing nuclear halogenated methylbenzyl alcohol which is a useful substance as a raw material, an intermediate for manufacturing medicines, agricultural chemicals, etc. The process of the present invention for preparing nucleus-halogenated methylbenzyl alcohol represented by the following formula (II) comprises hydrogenating nucleus-halogenated benzene carbaldehyde represented by the following formula (I); wherein m is an integer of 0 to 3, and n is an integer of 1 to 4, with the proviso that m+n is an integer of 1 to 4, wherein m and n are the same as those in the formula (I).
    Type: Application
    Filed: June 12, 2006
    Publication date: June 10, 2010
    Applicant: SHOWA DENKO K.K.
    Inventors: Haruhiko Ikeda, Hideo Miyata
  • Publication number: 20100137615
    Abstract: Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.
    Type: Application
    Filed: February 9, 2010
    Publication date: June 3, 2010
    Applicant: Takasago International Corporation
    Inventors: Hideo SHIMIZU, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
  • Patent number: 7718831
    Abstract: Method of asymmetrically hydrosilylating substrates using catalysts having a ligand of the compound of the formula (I) wherein R is optionally substituted alkyl, cycloalkyl, aryl or heteroaryl; R? is hydrogen, optionally substituted lower alkyl; and R? is hydrogen, halogen, optionally substituted alkyl, hydroxy, amino (e.g., primary, secondary or tertiary), alkenyl; or an enantiomer thereof; or an enantiomeric mixture thereof with a transition metal. Particularly suitable reactions include the asymmetric hydrosilylation of ketones.
    Type: Grant
    Filed: February 16, 2006
    Date of Patent: May 18, 2010
    Assignee: The Hong Kong Polytechnic University
    Inventors: Albert S Chan, Jianxin Ji, Jing Wu
  • Publication number: 20100069684
    Abstract: The invention relates to the asymmetric (transfer) hydrogenation of a prochiral keton, prochiral imine, oxime, oxime derivative, hydrazone or hydrazone derivative, using a transition metal catalyst, characterized in that as a catalyst is used a transition metal complex of the general formula [I]: MaL1bL2c(N)dXe wherein a, b, c, d and e are integers; a, b and d can have a value of 1-6; c and e can have a value of 0-6; M is transition metal selected from the group consisting of Ru1 Rh and Ir; L1 is an enantiomerically enriched chiral monodentate phosphor-containing ligand of the general formula [II] or of the general formula [III]; L2 is any monodentate or bidentate neutral or monoanionic ligand, which may be chiral; N is a compound containing at least one primary or secondary amine group; X is a anion.
    Type: Application
    Filed: December 21, 2007
    Publication date: March 18, 2010
    Inventors: Johannes Gerardus De Vries, Bart Stegink
  • Patent number: 7678947
    Abstract: A method for producing a halogen-substituted benzenedimethanol represented by the formula (2): wherein X1 to X4 are the same or different and independently represent a halogen atom or the like, provided that at least one of X1 to X4 is a halogen atom, by reacting a halogen-substituted terephthalic acid diester represented by the formula (1): wherein R1 and R2 are the same or different and independently represent a C1-C20 alkyl group which may have a substitutent or substituents, and X1 to X4 is the same as defined above, with a borohydride compound in the presence of an alcohol which comprises adding the alcohol into a mixture of the halogen-substituted terephthalic acid diester represented by the formula (1), the borohydride compound and a solvent.
    Type: Grant
    Filed: August 2, 2005
    Date of Patent: March 16, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Koji Hagiya
  • Patent number: 7667075
    Abstract: A diamine of formula (I) is described, in which A is hydrogen or a saturated or unsaturated C1-C20 alkyl group or an aryl group; B is a substituted or unsubstituted C1-C20 alkyl, cycloalkyl, alkaryl, alkaryl or aryl group or an alkylamino group and at least one of X1, X2, Y1, Y2 or Z is a C1-C10 alkyl, cycloalkyl, alkaryl, aralkyl or alkoxy substituting group. The chiral diamine may be used to prepare catalysts suitable for use in transfer hydrogenation reactions.
    Type: Grant
    Filed: November 1, 2005
    Date of Patent: February 23, 2010
    Assignee: Bial - Portela & CA, S.A.
    Inventors: Beatriz Dominguez, Antonio Zanotti-Gerosa, Gabriela Alexandra Grasa, Jonathan Alan Medlock
  • Patent number: 7663003
    Abstract: A process for hydrogenating an organic compound which has at least one carbonyl group, in which the organic compound is brought into contact in the presence of hydrogen with a shaped article which can be produced in a process in which (i) an oxidic material comprising copper oxide, aluminum oxide and at least one of the oxides of lanthanum, tungsten, molybdenum, titanium or zirconium is prepared, (ii) powdered metallic copper, copper flakes, powdered cement, graphite or a mixture thereof is added to the oxidic material, and (iii) the mixture resulting from (ii) is shaped to a shaped article.
    Type: Grant
    Filed: November 9, 2007
    Date of Patent: February 16, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Sylvia Huber-Dirr, Michael Hesse, Andrea Haunert, Henrik Junicke
  • Publication number: 20100029985
    Abstract: A process for the preparation of a compound of Formula (1) wherein Ar represents an optionally substituted hydrocarbyl or an optionally substituted heterocyclyl group comprising an aromatic moiety; and R1 and R2 each independently represent an optionally substituted hydrocarbyl or an optionally substituted heterocyclyl group; said process comprising: a) reducing a compound of Formula (2) to form a compound of Formula (3): b) activating the compound of Formula (3) to form a compound of Formula (4): wherein OX represents a leaving group; and c) coupling the compound of Formula (4) to a compound of Formula (5): to form a compound of Formula (1). A stereoselective reduction of ketones to alcohols is also disclosed.
    Type: Application
    Filed: December 14, 2005
    Publication date: February 4, 2010
    Applicant: AVECIA PHARMACEUTICALS LIMITED
    Inventors: George Robert Hodges, Juliette Martin, Noel Anthony Hammil, Ian Nicholas Houson
  • Publication number: 20090326235
    Abstract: The present invention relates to anhydrous solutions of MX3-Z LiA in a solvent, wherein M is a lanthanide including lanthanum, or yttrium or indium; z>0; and X and A are independently or both monovalent anions, preferably Cl, Br or I. The solution is readily prepared by dissolving or suspending MX3 or its hydrate and z equiv LiA in water or hydrophilic solvents, or mixtures thereof, removing the solvent under vacuum and dissolving the resulting powder in another solvent. The solution of MX3-Z LiA can advantageously be used e.g. in addition reactions of Grignard reagents to ketones and imines. Even the catalytic use of MX3-Z LiA is possible.
    Type: Application
    Filed: September 1, 2006
    Publication date: December 31, 2009
    Inventors: Paul Knochel, Arkady Krasovskiy, Felix Kopp
  • Patent number: 7601867
    Abstract: A diamine of formula (I) is described, in which A is hydrogen or a saturated or unsaturated C1-C20 alkyl group or an aryl group; B is a substituted or unsubstituted C1-C20 alkyl, cycloalkyl, alkaryl, alkaryl or aryl group or an alkylamino group and at least one of X1, X2, Y1, Y2 or Z is a C1-C10 alkyl, cycloalkyl, alkaryl, aralkyl or alkoxy substituting group. The chiral diamine may be used to prepare catalysts suitable for use in transfer hydrogenation reactions.
    Type: Grant
    Filed: November 1, 2005
    Date of Patent: October 13, 2009
    Assignee: Bial-Portela & CA, S.A.
    Inventors: Beatriz Dominguez, Antonio Zanotti-Gerosa, Gabriela Alexandra Grasa, Jonathan Alan Medlock
  • Publication number: 20090253919
    Abstract: Chiral thioureas are effective catalysts for the borane reduction of prochiral ketones to optically active alcohols. A prochiral ketone may be reduced to an optically active alcohol in the presence of a substantially sub-stoichiometric amount of chiral thiourea. The asymmetric thiourea compound of the present invention may be produced according to a production method described herein.
    Type: Application
    Filed: April 3, 2008
    Publication date: October 8, 2009
    Applicant: Board of Regents
    Inventors: Derun Li, John R. Falck
  • Patent number: 7569735
    Abstract: A method for producing alcohols which comprises reducing esters or lactones with hydrogen gas in the presence of a catalyst comprising (i) a ruthenium compound, (ii) a monodentate monophosphine or a bidentate bisphosphine, and (iii) an amine. Examples of the catalyst include a ruthenium (Ru) complex represented by the formula:RuX1X2(LP)m(LN)n [X1 and X2 each represent an anionic ligand, LP represents a phosphine ligand, m is 1 when LP is bidentate, while m is 2 when LP is monodentate, LN represents an amine ligand, and n is 1 when LN is bidentate, while n is 2 when LN is monodentate.] and a catalyst comprising an amine and a ruthenium (Ru) complex of the formula: RuX1X2(LP1)r [LP1 represents a monophosphine ligand and r is 3 or 4.].
    Type: Grant
    Filed: March 14, 2008
    Date of Patent: August 4, 2009
    Assignee: Takasago International
    Inventors: Yasunori Ino, Akifumi Yoshida, Wataru Kuriyama
  • Publication number: 20090062573
    Abstract: The present invention provides an asymmetric reduction catalyst effective in preparing optically-active alcohol compounds having various functional groups, and a process for preparing optically-active alcohol compounds using said asymmetric reduction catalyst. The organic metal compound of the present invention is represented by the following general formula (1): wherein R1 and R2 may be mutually identical or different, and are an alkyl group, a phenyl group, a naphthyl group, a cycloalkyl group, or an alicyclic ring formed by binding R1 and R2, which may have a substituent; R3 is a hydrogen atom or an alkyl group; Cp is a cyclopentadienyl group, which may have a substituent, bound to M1 via a ? bond; X1 is a halogen atom or a hydrido group; M1 is rhodium or iridium; and * denotes asymmetric carbon.
    Type: Application
    Filed: July 18, 2008
    Publication date: March 5, 2009
    Applicant: Kanto Kagaku Kabushiki Kaisha
    Inventors: Takashi Miki, Junichi Hori, Toshihide Takemoto, Noriyuki Utsumi, Takeaki Katayama, Masahito Watanabe, Kunihiko Murata
  • Publication number: 20090023961
    Abstract: The present disclosure relates to a process for the hydrogenation of compounds comprising one or more carbon-oxygen (C?O) double bonds, to provide the corresponding alcohol, comprising contacting the compound with hydrogen gas at and a catalyst comprising a ruthenium-aryl-aminophosphine complex.
    Type: Application
    Filed: July 7, 2008
    Publication date: January 22, 2009
    Inventors: Xuanhua Chen, Wenli Jia, Kamaluddin Abdur-Rashid, Rongwei Guo
  • Patent number: 7465839
    Abstract: The invention relates to a process for hydrogenating ketones, wherein the ketone is fed in a mixture with hydrogen to a catalyst bed which comprises a copper chromite catalyst which has a proportion of SiO2 as catalyst.
    Type: Grant
    Filed: November 16, 2005
    Date of Patent: December 16, 2008
    Assignee: Süd-Chemie AG
    Inventor: Jürgen Ladebeck
  • Publication number: 20080300430
    Abstract: The present disclosure relates to a process for the reduction of compounds comprising one or more carbon-oxygen (C?O) double bonds, to provide the corresponding alcohol, comprising contacting the compound with hydrogen gas at a pressure greater than 3 atm and a catalyst comprising an iridium aminodiphosphine complex.
    Type: Application
    Filed: May 30, 2008
    Publication date: December 4, 2008
    Inventors: Kamaluddin Abdur-Rashid, Rongwei Guo, Xuanhua Chen, Wenli Jia