Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/814)
  • Patent number: 10570072
    Abstract: A chemoselective process for producing alcohols from ?,?-unsaturated aldehydes and ketones is described.
    Type: Grant
    Filed: June 12, 2017
    Date of Patent: February 25, 2020
    Assignee: GIVAUDAN SA
    Inventors: Roger Wilhelm Geisser, Nathalie Joset
  • Patent number: 9862670
    Abstract: Bicomponent catalysts and methods for making bio-based acrylic acid, acrylic acid derivatives, or mixtures thereof from lactic acid, lactic acid derivatives, or mixtures thereof are provided.
    Type: Grant
    Filed: March 11, 2016
    Date of Patent: January 9, 2018
    Assignee: The Procter & Gamble Company
    Inventors: Dimitris Ioannis Collias, Jeffrey Charles Hayes, William David Laidig
  • Patent number: 9545617
    Abstract: A catalyst is provided. The catalyst includes a carrier and a metal Pd. The carrier is represented by a formula: MxAl(1?x)O(3?x)/2, where M is an alkaline earth metal, and x is between 0.09 and 0.24. The metal Pd is loaded on the carrier. A method for manufacturing the catalyst and a method for manufacturing a hydrogenated bisphenol A or derivatives thereof using the catalyst are also provided.
    Type: Grant
    Filed: December 9, 2015
    Date of Patent: January 17, 2017
    Assignee: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: Kuo-Ching Wu, Chiou-Hwang Lee
  • Patent number: 9255324
    Abstract: The present disclosure is related to an aluminum-containing precursor composition, especially a precursor composition which is vaporized to be used for vapor phase deposition processes such as chemical vapor deposition (CVD) or atomic layer deposition (ALD).
    Type: Grant
    Filed: August 14, 2013
    Date of Patent: February 9, 2016
    Assignee: UP CHEMICAL CO., LTD.
    Inventors: Wonyong Koh, Won Seok Han, Myeong-Ho Park
  • Patent number: 9222056
    Abstract: A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent selected from the group consisting of (i) a salt and/or an ester of a phosphorous oxo acid, (ii) a derivative of the phosphorous oxo acid in which at least one P—H bond has been replaced by a P—C bond, (iii) a salt and/or an ester of the derivative, and (iv) combinations thereof; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product.
    Type: Grant
    Filed: December 22, 2011
    Date of Patent: December 29, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Bruce E. Firth, Sharon E. Kirk
  • Patent number: 9175231
    Abstract: A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent selected from the group consisting of phosphorous acid, phosphinic acid, and a combination thereof; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product. Methods for suppressing isomerization of olefin metathesis products produced in a metathesis reaction, and methods of producing fuel compositions are described.
    Type: Grant
    Filed: December 22, 2011
    Date of Patent: November 3, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Bruce E. Firth, Sharon E. Kirk, Vasudeo S. Gavaskar
  • Patent number: 9169447
    Abstract: A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent that comprises nitric acid; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product. Methods for suppressing isomerization of olefin metathesis products produced in a metathesis reaction, and methods of producing fuel compositions are described.
    Type: Grant
    Filed: December 22, 2011
    Date of Patent: October 27, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Bruce E. Firth, Sharon E. Kirk
  • Patent number: 9090533
    Abstract: The present invention relates to the field of perfumery. More particularly, it concerns a process for the preparation of 2-methyl-4-phenyl-2-butanol, or even 4-cyclohexyl-2-methyl-2-butanol from 4,4-dimethyl-2,6-diphenyl-1,3-dioxane.
    Type: Grant
    Filed: June 24, 2013
    Date of Patent: July 28, 2015
    Assignee: Firmenich SA
    Inventors: Koenraad P. Vanhessche, Jean-Paul Leresche
  • Patent number: 9040755
    Abstract: A process for preparation of 2-phenyl ethanol by catalytic hydrogenation of styrene oxide using a catalyst consisting of Pd (II) on basic inorganic support is investigated. The present invention comprises development of new Pd based catalysts. The present method yields 2-phenyl ethanol in 98% selectivity at total conversion of styrene oxide. The present process represents an environment friendly alternative to conventionally used methods in industry and eliminates the reduction step for catalyst preparation. In the present invention the active catalyst is generated in situ during the hydrogenation of styrene oxide. In addition, Pd (II) supported catalysts do not catch fire (non pyrophoric), can be stored under ambient conditions and produce very less or no dust which makes said catalysts suitable for industrial application.
    Type: Grant
    Filed: December 14, 2012
    Date of Patent: May 26, 2015
    Assignee: Council of Scientific and Industrial Research
    Inventors: Hari Chand Bajaj, Sayed Hasan Razi Abdi, Rukhsana Ilyas Kureshy, Noor-Ul Hasan Khan, Aasif Asharafbhai Dabbawala, Tamal Roy
  • Patent number: 8962852
    Abstract: The invention relates to an asymmetric hydrogenation method for ketone compounds, comprising the step of: under hydrogen atmosphere, in the presence of an in situ catalyst derived from a chiral ligand and a ruthenium salt, adding a ketone compound and a base into a second solvent to carry out an asymmetric hydrogenation for the ketone compound. The invention can obtain a conversion of 100% and a highest asymmetric inducement effect of 99.7% for the ketone compound. The invention has the advantages including simple procedure, high conversion and selectivity, good atom economy and good prospect of industrial application.
    Type: Grant
    Filed: April 16, 2012
    Date of Patent: February 24, 2015
    Assignee: Nippon Chemical Industries Co., Ltd.
    Inventors: Wanbin Zhang, Delong Liu, Hui Guo, Yangang Liu
  • Publication number: 20150031920
    Abstract: [Object] The object of this invention is to provide a method for producing an optically active secondary alcohol at a high optical purity by hydrogenating a substrate carbonyl compound at a high efficiency using as a catalyst a ruthenium complex bearing as a ligand certain optically active diphosphine compound and a readily synthesized amine compound.
    Type: Application
    Filed: July 25, 2014
    Publication date: January 29, 2015
    Inventors: TAKEAKI KATAYAMA, KUNIHIKO TSUTSUMI, KUNIHIKO MURATA, TAKESHI OHKUMA, NORIYOSHI ARAI
  • Publication number: 20150005500
    Abstract: Disclosed are novel ruthenium compounds of formula (Ia) and (Ib): wherein R1 and the moiety are defined herein. Also disclosed is a process for using these novel ruthenium compounds as catalysts for asymmetric hydrogenation and transfer hydrogenation of ketones with high reactivities and excellent selectivities.
    Type: Application
    Filed: June 24, 2014
    Publication date: January 1, 2015
    Applicant: Boehringer Ingelheim International GmbH
    Inventors: Nizar HADDAD, Heewon LEE, Bo QU, Sonia RODRIGUEZ, Chris Hugh SENANAYAKE
  • Publication number: 20140357903
    Abstract: The present invention relates to a process for hydrogenating a substrate including a carbon-heteroatom double bond, the process including the step of reacting the substrate with hydrogen gas in the presence of a hydrogenation catalyst, wherein the hydrogenation catalyst is a complex of formula (I): R1-10, A and Hal are as defined in the specification. The present invention also provides processes for the preparation of the complex of formula (I) and intermediates thereof.
    Type: Application
    Filed: August 13, 2014
    Publication date: December 4, 2014
    Applicant: JOHNSON MATTHEY PUBLIC LIMITED COMPANY
    Inventors: Alan DYKE, Damian Mark GRAINGER, Jonathan Alan MEDLOCK, Hans Guenter NEDDEN, Jacques Jean Marie LE PAIH, Stephen James ROSEBLADE, Andreas SEGER, Vilvanathan SIVAKUMAR, Antonio ZANOTTI-GEROSA
  • Patent number: 8901323
    Abstract: Provided is a ruthenium complex that is represented by general formula (1*) and is useful as an asymmetric reduction catalyst. (In the formula, * is an asymmetric carbon atom; R1 is an arenesulfonyl group, and the like; R2 and R3 are a phenyl group, and the like; R10 through R14 are selected from a hydrogen atom, C1-10 alkyl group, and the like, but R10 through R14 are not simultaneously hydrogen atoms; X is a halogen atom and the like; j and k are each either 0 or 1; and j+k is 0 or 2.
    Type: Grant
    Filed: May 2, 2012
    Date of Patent: December 2, 2014
    Assignee: Takasago International Corporation
    Inventors: Taichiro Touge, Tomohiko Hakamata, Hideki Nara
  • Patent number: 8889920
    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: Grant
    Filed: February 11, 2011
    Date of Patent: November 18, 2014
    Assignee: BASF SE
    Inventors: Florian Stecker, Ulrich Griesbach, Martin Bock, Lucia Königsmann
  • Publication number: 20140330047
    Abstract: A process for preparation of 2-phenyl ethanol by catalytic hydrogenation of styrene oxide using a catalyst consisting of Pd (II) on basic inorganic support is investigated. The present invention comprises development of new Pd based catalysts. The present method yields 2-phenyl ethanol in 98% selectivity at total conversion of styrene oxide. The present process represents an environment friendly alternative to conventionally used methods in industry and eliminates the reduction step for catalyst preparation. In the present invention the active catalyst is generated in situ during the hydrogenation of styrene oxide. In addition, Pd (II) supported catalysts do not catch fire (non pyrophoric), can be stored under ambient conditions and produce very less or no dust which makes said catalysts suitable for industrial application.
    Type: Application
    Filed: December 14, 2012
    Publication date: November 6, 2014
    Inventors: Hari Chand Bajaj, Sayed Hasan Razi Abdi, Rukhsana Ilyas Kureshy, Noor-UI Hasan Khan, Aasif Asharafbhai Dabbawala, Tamal Roy
  • Patent number: 8859815
    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: December 7, 2011
    Date of Patent: October 14, 2014
    Assignee: Bial-Portela & C.A., S.A.
    Inventors: Beatriz Dominguez, Antonio Zanotti-Gerosa, Gabriela Alexandra Grasa, Jonathan Alan Medlock
  • Patent number: 8846983
    Abstract: An object of the present invention is to provide a method for reducing a halogenobenzoic acid ester, in which dehalogenation is inhibited, by using a readily available catalyst. The method comprises reducing an ester with hydrogen gas by using an aromatic hydrocarbon as a solvent in the presence of a ruthenium complex represented by the following general formula (1): RuXY(CO)(L)??(1) where X and Y represent monovalent anionic ligands, and L represents a tridentate aminodiphosphine ligand represented by the following general formula (2): where RZ1 represents an alkyl group having 1 to 4 carbon atoms, each RZ2 represents an alkyl group having 1 to 4 carbon atoms or a halogen atom, any adjacent two RZ2s may form a ring, Hal represents a halogen atom, and n represents 0 to 4.
    Type: Grant
    Filed: December 9, 2013
    Date of Patent: September 30, 2014
    Assignee: Takasago International Corporation
    Inventors: Kiyoto Hori, Osamu Ogata, Wataru Kuriyama
  • Publication number: 20140187809
    Abstract: The present invention provides a novel ruthenium complex which has an excellent catalytic activity in terms of reactivity for an asymmetric reduction of a carbonyl compound and enantioselectivity, a catalyst using the ruthenium complex, and a method for preparing optically active alcohol compounds using the ruthenium complex. The present invention relates to a ruthenium complex having a ruthenacycle structure, a catalyst for an asymmetric reduction consisting of the ruthenium complex, and a method for preparing optically active alcohol compounds using the ruthenium complex.
    Type: Application
    Filed: April 2, 2012
    Publication date: July 3, 2014
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Kiyoto Hori, Kazuhiko Matsumura
  • Publication number: 20140179923
    Abstract: A new class of ligands derived from benzo[h]quinoline are described and these ligands are used to prepare several novel transition metal complexes. The complexes are preferably of the group VIII transition metals iron, ruthenium or osmium, with the benzo[h]quinoline ligands acting as tridentate ligands. The complexes described are proved to be very active catalysts for the reduction of ketones and aldehydes to alcohols, via hydrogen transfer and hydrogenation reactions. These compounds hence can be usefully employed as catalysts in said reduction reactions.
    Type: Application
    Filed: November 19, 2013
    Publication date: June 26, 2014
    Applicant: UNIVERSITA' DEGLI STUDI DI UDINE
    Inventors: Pierluigi Rigo, Walter Baratta, Katia Siega, Giorgio Adolfo Chelucci, Maurizio Ballico, Santo Magnolia
  • Publication number: 20140179946
    Abstract: Phosphoranimide-metal catalysts and their role in hydrogenation and hydrosilylation are disclosed. The catalysts comprise first row transition metals such as nickel, cobalt or iron. The catalysts have a metal to anionic phosphoranimide ratio of 1:1. This disclosure presents a process for catalytic hydrogenation and hydrosilylation of a range of unsaturated organic compounds under lower temperature and pressure conditions than conditions associated with industrial hydrogenation and hydrosilylation.
    Type: Application
    Filed: December 21, 2012
    Publication date: June 26, 2014
    Applicant: GOVERNORS OF THE UNIVERSITY OF ALBERTA
    Inventors: Jeffrey Camacho BUNQUIN, Jeffrey Mark STRYKER
  • Patent number: 8716508
    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 addition salt of an aminophosphine, diaminophosphine, aminodiphosphine or diaminodiphosphine, in the presence of a base.
    Type: Grant
    Filed: October 8, 2009
    Date of Patent: May 6, 2014
    Assignee: Kanata Chemical Technologies Inc.
    Inventors: Kamaluddin Abdur-Rashid, Dino Amoroso, Xuanhua Chen, Rongwei Guo, Shuiming Lu, Chi-Wing Tsang
  • Publication number: 20140051871
    Abstract: Provided is a ruthenium complex that is represented by general formula (1*) and is useful as an asymmetric reduction catalyst. (In the formula, * is an asymmetric carbon atom; R1 is an arenesulfonyl group, and the like; R2 and R3 are a phenyl group, and the like; R10 through R14 are selected from a hydrogen atom, C1-10 alkyl group, and the like, but R10 through R14 are not simultaneously hydrogen atoms; X is a halogen atom and the like; j and k are each either 0 or 1; and j+k is 0 or 2.
    Type: Application
    Filed: May 2, 2012
    Publication date: February 20, 2014
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Taichiro Touge, Tomohiko Hakamata, Hideki Nara
  • Patent number: 8642813
    Abstract: The present invention provides methods, reactor systems, and catalysts for converting in a continuous process biomass to less complex oxygenated compounds for use in downstream processes to produce biofuels and chemicals. The invention includes methods of converting the components of biomass, such as hemicellulose, cellulose and lignin, to water-soluble materials, including lignocellulosic derivatives, cellulosic derivatives, hemicellulosic derivatives, carbohydrates, starches, polysaccharides, disaccharides, monosaccharides, sugars, sugar alcohols, alditols, polyols, diols, alcohols, ketones, cyclic ethers, esters, carboxylic acids, aldehydes, and mixtures thereof, using hydrogen and a heterogeneous liquefaction catalyst.
    Type: Grant
    Filed: December 29, 2011
    Date of Patent: February 4, 2014
    Assignee: Virent, Inc.
    Inventors: Ming Qiao, Randy D. Cortright, John Kania, Elizabeth Woods
  • Publication number: 20130345445
    Abstract: The present invention relates to a method of reducing a C—O bond to the corresponding C—H bond in a substrate which could be a benzylic alcohol, allylic alcohol, ester, or ether or an ether bond beta to a hydroxyl group or alpha to a carbonyl group.
    Type: Application
    Filed: March 8, 2012
    Publication date: December 26, 2013
    Applicant: KAT2BIZ AB
    Inventors: Joseph Samec, Anna Lundstedt, Supaporn Sawadjoon
  • Patent number: 8614345
    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 and/or aldehydes into the corresponding alcohol respectively. Said catalysts are ruthenium complexes comprising a tetradentate ligand (L4) coordinating the ruthenium with: —two nitrogen atoms, each in the form of a primary or secondary amine (i.e. a NH2 or NH group) or N-alkyl imine functional groups (i.e. a C?N group), and —two sulfur atoms, each in the form of thioether functional groups.
    Type: Grant
    Filed: December 19, 2011
    Date of Patent: December 24, 2013
    Assignee: Firmenich SA
    Inventors: Francesco Santoro, Lionel Saudan, Michel Alfred Joseph Saudan, Sylvia Joyeuse Adélaïde Ada Saudan
  • Publication number: 20130274487
    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 and/or aldehydes into the corresponding alcohol respectively. Said catalysts are ruthenium complexes comprising a tetradentate ligand (L4) coordinating the ruthenium with: two nitrogen atoms, each in the form of a primary or secondary amine (i.e. a NH2 or NH group) or N-alkyl imine functional groups (i.e. a C?N group), and two sulfur atoms, each in the form of thioether functional groups.
    Type: Application
    Filed: December 19, 2011
    Publication date: October 17, 2013
    Applicant: FIRMENICH SA
    Inventors: Sylvia Joyeuse Adélaïde Ada Saudan, Michel Alfred Joseph Saudan
  • Patent number: 8524953
    Abstract: Provided is an alcohol production method comprising the step of reducing an ester or a lactone with hydrogen to produce a corresponding alcohol without addition of a base compound by using, as a catalyst, a ruthenium complex represented by the following general formula (1): RuH(X)(L1)(L2)n??(1) wherein X represents a monovalent anionic ligand, L1 represents a tetradentate ligand having at least one coordinating phosphino group and at least one coordinating amino group or a bidentate aminophosphine ligand having one coordinating phosphino group and one coordinating amino group, and L2 represents a bidentate aminophosphine ligand having one coordinating phosphino group and one coordinating amino group, provided that n is 0 when L1 is the tetradentate ligand, and n is 1 when L1 is the bidentate aminophosphine ligand.
    Type: Grant
    Filed: September 12, 2012
    Date of Patent: September 3, 2013
    Assignee: Takasago International Corporation
    Inventors: Wataru Kuriyama, Yasunori Ino, Osamu Ogata
  • Publication number: 20130225822
    Abstract: The present invention relates to a chiral spiro-pyridylamidophosphine ligand compound, synthesis method therefor and application thereof. The chiral spiro-pyridylamidophosphine compound is a compound having a structure of Formula (I), a racemate or optical isomer thereof, or a catalytically acceptable salt thereof, and is mainly characterized by having a chiral spiro-dihydro-indene skeleton in its structure. The chiral spiro-pyridylamidophosphine compound may be synthesized with optical active 7-diaryl/alkylphosphino-7?-amino-1,1?-spiro-dihydro-indene or substituted 7-diaryl/alkylphosphino-7?-amino-1,1?-spiro-dihydro-indene having a spiro-skeleton as chiral starting material. The chiral spiro-pyridylamidophosphine compound may be used as a chiral ligand in asymmetric hydrogenation of a carbonyl compound catalyzed by iridium, in which the reaction activity is very high, the amount of the catalyst may be 0.0001 mol %, and the enantioselectivity of the reaction is up to 99.9% ee.
    Type: Application
    Filed: November 18, 2011
    Publication date: August 29, 2013
    Inventors: Qilin Zhou, Jianhua Xie, Xiaoyan Liu, Jianbo Xie, Lixin Wang
  • Patent number: 8497400
    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: Grant
    Filed: February 9, 2010
    Date of Patent: July 30, 2013
    Assignee: Takasago International Corporation
    Inventors: Hideo Shimizu, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
  • Patent number: 8481791
    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: Grant
    Filed: February 9, 2010
    Date of Patent: July 9, 2013
    Assignee: Takasago International Corporation
    Inventors: Hideo Shimizu, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
  • Patent number: 8471048
    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: Grant
    Filed: June 30, 2010
    Date of Patent: June 25, 2013
    Assignee: Takasago International Corporation
    Inventors: Wataru Kuriyama, Takaji Matsumoto, Yasunori Ino, Osamu Ogata
  • Publication number: 20130158276
    Abstract: Provided is a catalyst for asymmetric reduction, which can be produced by a convenient and safe production method, has a strong catalytic activity, and has excellent stereoselectivity. The present invention relates to a ruthenium complex represented by the following formula (1): wherein R1 represents an alkyl group or the like; Y represents a hydrogen atom; X represents a halogen atom or the like; j and k each represent 0 or 1; R2 and R3 each represent an alkyl group or the like; R11 to R19 each represent a hydrogen atom, an alkyl group or the like; Z represents oxygen or sulfur; n1 represents 1 or 2; and n2 represents an integer from 1 to 3, a method for producing the ruthenium complex, a catalyst for asymmetric reduction formed from the ruthenium complex, and methods for selectively producing an optically active alcohol and an optically active amine using the catalyst for asymmetric reduction.
    Type: Application
    Filed: June 17, 2011
    Publication date: June 20, 2013
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Taichiro Touge, Hideki Nara, Tomohiko Hakamada
  • Publication number: 20130150623
    Abstract: An object is to provide a process for providing hydrogen or heavy hydrogens conveniently without the necessity of large-scale equipment and a process capable of performing hydrogenation (protiation, deuteration or tritiation) reaction conveniently without the use of an expensive reagent and a special catalyst. The production process includes a process for producing hydrogen or heavy hydrogens, containing subjecting water or heavy water to mechanochemical reaction in the presence of a catalyst metal, and a process for producing a hydrogenated (protiated, deuterated or tritiated) organic compound, containing subjecting an organic compound and water or heavy water to mechanochemical reaction in the presence of a catalyst metal.
    Type: Application
    Filed: August 16, 2011
    Publication date: June 13, 2013
    Applicant: Shiono Chemical Co., Ltd.
    Inventors: Hironao Sajiki, Yasunari Monguchi, Yoshinari Sawama, Shinichi Kondo
  • Patent number: 8455700
    Abstract: The present invention relates to a process for preparing phenylalkan-1-ols in three stages, where an ester condensation in the presence of alkali metal or alkaline earth metal alcoholates is carried out in the first stage.
    Type: Grant
    Filed: July 27, 2009
    Date of Patent: June 4, 2013
    Assignee: BASF SE
    Inventors: Martine Weis, Daniel Breuninger, Klaus Ebel, Harald Winsel
  • Publication number: 20130096317
    Abstract: The embodiments described herein provide a reduction of an aldehyde or a ketone, such as a Meerwein-Ponnorf-Verley (MPV) reaction of an aldehyde or ketone. In some embodiments, the reaction occurs in the presence of Al[OC(CH3)3]. In some embodiments, the reaction occurs in the presence of an aprotic solvent. In some embodiments, the aldehyde or ketone is an amino aldehyde or an amino ketone wherein the amine is group is protected such that the nitrogen of the amine has no proton. Other embodiments related to compositions and compounds related to the reduction reaction, or to the preparation or use of the aldehyde, the ketone, or the resulting alcohol.
    Type: Application
    Filed: November 12, 2010
    Publication date: April 18, 2013
    Applicants: GEORGIA TECH RESEARCH CORPORATION, AMERICAN PACIFIC CORPORATION
    Inventors: Charles L. Liotta, Pamela Pollet, Kristen Kitagawa Fisher, William Dubay, Joy Stringer
  • Patent number: 8410320
    Abstract: A method for synthesis of secondary alcohols is provided for pharmaceutical secondary alcohol by addition of organoboronic acids with aldehydes in presence of the cobalt ion and bidentate ligands as the catalyst. In addition, an enantioselective synthesis method for secondary alcohols is also herein provided in the present invention. The present invention has advantages in using less expensive cobalt ion and commercially available chiral ligands as the catalyst, wide scope of organoboronic acids and aldehydes compatible with this catalytic reaction and achieving excellent yields and/or enantiomeric excess.
    Type: Grant
    Filed: March 10, 2011
    Date of Patent: April 2, 2013
    Assignee: National Tsing Hua University
    Inventors: Chien-Hong Cheng, Jaganathan Karthikeyan, Pang-Chi Huang
  • Patent number: 8399710
    Abstract: An alkali metal fluoride dispersion of an alkali metal fluoride and an aprotic organic solvent is obtainable by (A) separating a liquid phase from an alkali metal fluoride dispersion comprising an alcohol solvent and an alkali metal fluoride, and mixing the separated liquid phase with an aprotic organic solvent having a boiling point of 85° C. or higher at normal pressure; (B) obtaining a mixture containing the alkali metal fluoride by (b1) concentrating the mixture containing the alkali metal fluoride to obtain a concentrated fraction and a concentrated residue; (b2) mixing a residue of the alkali metal fluoride dispersion with the concentrated fraction obtained in (b1); and (b3) separating a liquid phase from the mixture containing an alkali metal fluoride obtained in (b2) and mixing the separated liquid phase with the concentrated residue; and (C) removing the alcohol solvent from the mixture containing the alkali metal fluoride.
    Type: Grant
    Filed: August 27, 2008
    Date of Patent: March 19, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Koji Hagiya
  • Publication number: 20130053574
    Abstract: The invention relates to an asymmetric hydrogenation method for ketone compounds, comprising the step of: under hydrogen atmosphere, in the presence of an in situ catalyst derived from a chiral ligand and a ruthenium salt, adding a ketone compound and a base into a second solvent to carry out an asymmetric hydrogenation for the ketone compound. The invention can obtain a conversion of 100% and a highest asymmetric inducement effect of 99.7% for the ketone compound. The invention has the advantages including simple procedure, high conversion and selectivity, good atom economy and good prospect of industrial application.
    Type: Application
    Filed: April 16, 2012
    Publication date: February 28, 2013
    Applicant: NIPPON CHEMICAL INDUSTRIAL CO., LTD.
    Inventors: Wanbin Zhang, Delong Liu, Hui Guo, Yangang Liu
  • Patent number: 8350091
    Abstract: A potassium fluoride dispersion essentially consisting of potassium fluoride and an aprotic organic solvent having a boiling point higher than that of methanol, which is obtainable by mixing a mixture containing potassium fluoride and 5 to 50 parts by weight of methanol per 1 part by weight of potassium fluoride with the aprotic organic solvent followed by concentrating the obtained mixture, and a process for producing a fluorine-containing organic compound comprising contacting an organic compound having at least one group capable of being substituted nucleophilically with a fluorine atom with the potassium fluoride dispersion.
    Type: Grant
    Filed: December 30, 2011
    Date of Patent: January 8, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Hagiya, Kazuaki Sasaki
  • Patent number: 8344187
    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: Grant
    Filed: June 26, 2009
    Date of Patent: January 1, 2013
    Assignees: Tokyo Institute of Technology, Central Glass Company, Limited
    Inventors: Takao Ikariya, Masato Ito, Akira Shiibashi, Takashi Ootsuka
  • Patent number: 8232420
    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: Grant
    Filed: April 12, 2010
    Date of Patent: July 31, 2012
    Assignee: Kanto Kagaku Kabushiki Kaisha
    Inventors: Masahito Watanabe, Junichi Hori
  • Patent number: 8227371
    Abstract: This invention relates to a metathesis catalyst comprising (i) a Group 8 metal hydride-dihydrogen complex represented by the formula: wherein M is a Group 8 metal; X is an anionic ligand; and L1 and L2 are neutral donor ligands; and (ii) a ligand exchange agent represented by the formula J-Y, wherein J is selected from the group consisting of hydrogen, a C1 to C30 hydrocarbyl, and a C1 to C30 substituted hydrocarbyl; and Y is selected from the group consisting of halides, alkoxides, aryloxides, and alkyl sulfonates.
    Type: Grant
    Filed: September 24, 2010
    Date of Patent: July 24, 2012
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Matthew W. Holtcamp, Matthew S. Bedoya, Laughlin G. McCullough
  • Patent number: 8198488
    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: Grant
    Filed: November 22, 2007
    Date of Patent: June 12, 2012
    Assignee: Firmenich SA
    Inventors: Lionel Saudan, Christophe Saudan, Michel Alfred Joseph Saudan, legal representative, Sylvia Joyeuse Adélaide Ada Saudan, legal representative
  • Patent number: 8198487
    Abstract: The present invention relates to a process for lithium exchange reactions comprising mixing at least two fluids in a microreactor having at least two injection points.
    Type: Grant
    Filed: February 1, 2008
    Date of Patent: June 12, 2012
    Assignee: Lonza AG
    Inventors: Dominique Roberge, Wilhelm Quittmann, Markus Eyholzer, Bertin Zimmermann, Fabio Rainone
  • Publication number: 20120136164
    Abstract: The invention relates to a nanoparticulate material comprising long ultrathin metal nanowires, and to processes for making it. The nanoparticulate material may be used as a catalyst and, in the presence of a chiral modifier, can catalyse enantioselective reactions.
    Type: Application
    Filed: March 30, 2010
    Publication date: May 31, 2012
    Applicant: Agency for Science, Technology and Research
    Inventors: Jackie Y. Ying, Nandanan Erathodiyil, Hongwei Gu, Huilin Shao, Jiang Jiang
  • Publication number: 20120129945
    Abstract: 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: Application
    Filed: August 2, 2010
    Publication date: May 24, 2012
    Applicant: Cognition Therapeutics, Inc.
    Inventors: Gilbert M. Rishton, Susan Catalano
  • Publication number: 20120123142
    Abstract: The present invention relates to a process for hydrogenating a substrate comprising a carbon-heteroatom double bond, the process comprising the step of reacting the substrate with hydrogen gas in the presence of a hydrogenation catalyst, wherein the hydrogenation catalyst is a complex of formula (I): R1-10, A and Hal are as defined in the specification. The present invention also provides processes for the preparation of the complex of formula (I) and intermediates thereof.
    Type: Application
    Filed: March 17, 2010
    Publication date: May 17, 2012
    Applicant: JOHNSON MATTHEY PUBLIC LIMITED COMPANY
    Inventors: Alan Dyke, Damian Mark Grainger, Jonathan Alan Medlock, Hans Guenter Nedden, Jacques Jean Marie Le Paih, Stephen James Roseblade, Andreas Seger, Vilvanathan Sivakumar, Antonio Zanotti-Gerosa
  • Patent number: 8124816
    Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of Ru complexes with tetradentate ligands having at least one amino or imino coordinating group and at least one phosphino coordinating group in hydrogenation processes for the reduction of esters or lactones into the corresponding alcohol or diol respectively.
    Type: Grant
    Filed: January 27, 2010
    Date of Patent: February 28, 2012
    Assignee: Firmenich SA
    Inventors: Lionel Saudan, Philippe Dupau, Jean-Jacques Riedhauser, Patrick Wyss
  • 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