Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/814)
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Publication number: 20120046479Abstract: 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: ApplicationFiled: October 8, 2009Publication date: February 23, 2012Inventors: Kamaluddin Abdur-Rashid, Dino Amoroso, Xuanhua Chen, Rongwei Guo, Shuiming Lu, Chi-Wing Tsang
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Publication number: 20120029195Abstract: 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: ApplicationFiled: March 30, 2010Publication date: February 2, 2012Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Yasutaka Aoyagi, Hiroshi Souda, Koji Hagiya
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Publication number: 20120010417Abstract: 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: ApplicationFiled: March 29, 2010Publication date: January 12, 2012Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Koji Hagiya, Yasutaka Aoyagi
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Publication number: 20110282077Abstract: 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: ApplicationFiled: May 10, 2011Publication date: November 17, 2011Applicant: Kanto Kagaku Kabushiki KaishaInventors: Taito Hatakeyama, Kunihiko Murata, Kunihiko Tsutsumi, Noriyuki Utsumi
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Patent number: 8044245Abstract: 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: GrantFiled: November 1, 2007Date of Patent: October 25, 2011Assignee: Korea Research Institute of Chemical TechnologyInventors: Kee-In Lee, Do-Min Lee
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Publication number: 20110237814Abstract: 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: ApplicationFiled: June 30, 2010Publication date: September 29, 2011Applicant: Takasago International CorporationInventors: Wataru Kuriyama, Takaji Matsumoto, Yasunori Ino, Osamu Ogata
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Patent number: 8013193Abstract: 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: GrantFiled: April 2, 2008Date of Patent: September 6, 2011Assignees: Kaneka Corporation, Takasago International CorporationInventors: Hirofumi Maeda, Kenji Inoue, Takaji Matsumoto, Izuru Nagasaki, Ryoji Noyori, Susumu Saito
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Publication number: 20110207968Abstract: 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: ApplicationFiled: February 11, 2011Publication date: August 25, 2011Applicant: BASF SEInventors: Florian Stecker, Ulrich Griesbach, Martin Bock, Lucia Königsmann
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Publication number: 20110201847Abstract: 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: ApplicationFiled: May 29, 2009Publication date: August 18, 2011Inventors: Hans-Jörg Wölk, Alfred Hagemeyer, Frank Grossmann, Silvia Neumann
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Publication number: 20110201820Abstract: 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: ApplicationFiled: December 11, 2008Publication date: August 18, 2011Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventor: Hideo Shimizu
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Publication number: 20110201819Abstract: 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: ApplicationFiled: December 11, 2008Publication date: August 18, 2011Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventor: Hideo Shimizu
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Publication number: 20110190523Abstract: 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: ApplicationFiled: October 1, 2009Publication date: August 4, 2011Inventors: Lionel Saudan, Christophe Saudan, Michel Alfred Jose Saudan, Sylvia Joyeuse Adélaïde Ada Saudan
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Patent number: 7973201Abstract: 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: GrantFiled: June 21, 2007Date of Patent: July 5, 2011Assignee: Sumitomo Chemical Company, LimitedInventor: Koji Hagiya
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Patent number: 7956182Abstract: 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: GrantFiled: February 13, 2007Date of Patent: June 7, 2011Assignee: Kotobuki Pharmaceutical Co., Ltd.Inventors: Hiroshi Tomiyama, Masayuki Yokota
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Patent number: 7956223Abstract: 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: GrantFiled: January 16, 2007Date of Patent: June 7, 2011Assignee: Sumitomo Chemical Company, LimitedInventor: Koji Hagiya
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Patent number: 7939695Abstract: 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: GrantFiled: June 12, 2006Date of Patent: May 10, 2011Assignee: Showa Denko K.K.Inventors: Haruhiko Ikeda, Hideo Miyata
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Publication number: 20110105693Abstract: 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: ApplicationFiled: May 1, 2009Publication date: May 5, 2011Applicant: KANATA CHEMICAL TECHNOLOGIES INC.Inventors: Kamaluddin Abdur-Rashid, Dino Amoroso, Christine Sui-Seng, Wenli Jia, Charles Ewart
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Publication number: 20110092747Abstract: 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: ApplicationFiled: June 26, 2009Publication date: April 21, 2011Applicants: TOKYO INSTITUTE OF TECHNOLOGY, CENTRAL GLASS COMPANY, LIMITEDInventors: Takao Ikariya, Masato Ito, Akira Shiibashi, Takashi Ootsuka
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Publication number: 20110065929Abstract: 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: ApplicationFiled: November 18, 2010Publication date: March 17, 2011Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Hideo SHIMIZU, Daisuke IGARASHI, Wataru KURIYAMA, Yukinori YUSA
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Patent number: 7884223Abstract: 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: GrantFiled: November 10, 2005Date of Patent: February 8, 2011Assignee: 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
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Publication number: 20110009646Abstract: 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: ApplicationFiled: July 13, 2010Publication date: January 13, 2011Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Taichiro Touge, Hideki Nara
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Patent number: 7858831Abstract: 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: GrantFiled: December 19, 2008Date of Patent: December 28, 2010Assignee: The Regents of the University of CaliforniaInventors: Matthew P. Meyer, Hui Zhu
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Publication number: 20100311975Abstract: 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: ApplicationFiled: October 30, 2008Publication date: December 9, 2010Inventors: Kamaluddin Abdur-Rashid, Dino Amoroso, Rongwei Guo, Xuanhua Chen, Christine Sui-Seng, Chi-Wing Tsang, Wenli Jia
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Publication number: 20100286401Abstract: 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: ApplicationFiled: November 20, 2007Publication date: November 11, 2010Inventors: Charles P. Casey, Hairong Guan
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Publication number: 20100286452Abstract: 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: ApplicationFiled: November 22, 2007Publication date: November 11, 2010Inventors: Lionel Saudan, Christophe Saudan, Michel Alfred Joseph Saudan, Sylvia Joyeuse Adelaide Ada Saudan
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Publication number: 20100280273Abstract: 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: ApplicationFiled: July 20, 2010Publication date: November 4, 2010Inventors: Lionel Saudan, Philippe Dupau, Jean-Jacques Riedhauser, Patrick Wyss
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Publication number: 20100261924Abstract: 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: ApplicationFiled: April 12, 2010Publication date: October 14, 2010Applicant: Kanto Kagaku Kabushiki KaishaInventors: Masahito Watanabe, Junichi Hori
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Patent number: 7807856Abstract: 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: GrantFiled: November 7, 2005Date of Patent: October 5, 2010Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Kentaro Kawazoe, Yasuo Yoshida
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Patent number: 7795478Abstract: 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: GrantFiled: October 4, 2006Date of Patent: September 14, 2010Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Koji Ueda, Manabu Yasumoto
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Patent number: 7777083Abstract: 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: GrantFiled: May 30, 2008Date of Patent: August 17, 2010Assignee: Kanata Chemical Technologies Inc.Inventors: Kamaluddin Abdur-Rashid, Rongwei Guo, Xuanhua Chen, Wenli Jia
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Patent number: 7772445Abstract: 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: GrantFiled: July 7, 2008Date of Patent: August 10, 2010Assignee: Kanata Chemical Technologies Inc.Inventors: Xuanhua Chen, Wenli Jia, Kamaluddin Abdur-Rashid, Rongwei Guo
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Publication number: 20100197976Abstract: 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: ApplicationFiled: January 29, 2010Publication date: August 5, 2010Applicant: Johnson Matthey PLCInventors: William Patrick Hems, Gabriela Alexandra Grasa
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Patent number: 7763758Abstract: 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: GrantFiled: September 12, 2007Date of Patent: July 27, 2010Assignee: Firmenich SAInventors: Lionel Saudan, Philippe Dupau, Jean-Jacques Riedhauser, Patrick Wyss
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Publication number: 20100168440Abstract: 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: ApplicationFiled: February 9, 2010Publication date: July 1, 2010Applicant: Takasago International CorporationInventors: Hideo SHIMIZU, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
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Publication number: 20100145106Abstract: 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: ApplicationFiled: June 12, 2006Publication date: June 10, 2010Applicant: SHOWA DENKO K.K.Inventors: Haruhiko Ikeda, Hideo Miyata
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Publication number: 20100137615Abstract: 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: ApplicationFiled: February 9, 2010Publication date: June 3, 2010Applicant: Takasago International CorporationInventors: Hideo SHIMIZU, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
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Patent number: 7718831Abstract: 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: GrantFiled: February 16, 2006Date of Patent: May 18, 2010Assignee: The Hong Kong Polytechnic UniversityInventors: Albert S Chan, Jianxin Ji, Jing Wu
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Publication number: 20100069684Abstract: 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: ApplicationFiled: December 21, 2007Publication date: March 18, 2010Inventors: Johannes Gerardus De Vries, Bart Stegink
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Patent number: 7678947Abstract: 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: GrantFiled: August 2, 2005Date of Patent: March 16, 2010Assignee: Sumitomo Chemical Company, LimitedInventor: Koji Hagiya
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Patent number: 7667075Abstract: 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: GrantFiled: November 1, 2005Date of Patent: February 23, 2010Assignee: Bial - Portela & CA, S.A.Inventors: Beatriz Dominguez, Antonio Zanotti-Gerosa, Gabriela Alexandra Grasa, Jonathan Alan Medlock
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Patent number: 7663003Abstract: 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: GrantFiled: November 9, 2007Date of Patent: February 16, 2010Assignee: BASF AktiengesellschaftInventors: Sylvia Huber-Dirr, Michael Hesse, Andrea Haunert, Henrik Junicke
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Publication number: 20100029985Abstract: 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: ApplicationFiled: December 14, 2005Publication date: February 4, 2010Applicant: AVECIA PHARMACEUTICALS LIMITEDInventors: George Robert Hodges, Juliette Martin, Noel Anthony Hammil, Ian Nicholas Houson
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Publication number: 20090326235Abstract: 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: ApplicationFiled: September 1, 2006Publication date: December 31, 2009Inventors: Paul Knochel, Arkady Krasovskiy, Felix Kopp
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Patent number: 7601867Abstract: 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: GrantFiled: November 1, 2005Date of Patent: October 13, 2009Assignee: Bial-Portela & CA, S.A.Inventors: Beatriz Dominguez, Antonio Zanotti-Gerosa, Gabriela Alexandra Grasa, Jonathan Alan Medlock
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Publication number: 20090253919Abstract: 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: ApplicationFiled: April 3, 2008Publication date: October 8, 2009Applicant: Board of RegentsInventors: Derun Li, John R. Falck
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Patent number: 7569735Abstract: 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: GrantFiled: March 14, 2008Date of Patent: August 4, 2009Assignee: Takasago InternationalInventors: Yasunori Ino, Akifumi Yoshida, Wataru Kuriyama
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Publication number: 20090062573Abstract: 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: ApplicationFiled: July 18, 2008Publication date: March 5, 2009Applicant: Kanto Kagaku Kabushiki KaishaInventors: Takashi Miki, Junichi Hori, Toshihide Takemoto, Noriyuki Utsumi, Takeaki Katayama, Masahito Watanabe, Kunihiko Murata
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Publication number: 20090023961Abstract: 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: ApplicationFiled: July 7, 2008Publication date: January 22, 2009Inventors: Xuanhua Chen, Wenli Jia, Kamaluddin Abdur-Rashid, Rongwei Guo
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Patent number: 7465839Abstract: 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: GrantFiled: November 16, 2005Date of Patent: December 16, 2008Assignee: Süd-Chemie AGInventor: Jürgen Ladebeck
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Publication number: 20080300430Abstract: 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: ApplicationFiled: May 30, 2008Publication date: December 4, 2008Inventors: Kamaluddin Abdur-Rashid, Rongwei Guo, Xuanhua Chen, Wenli Jia