Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/814)
  • Patent number: 6476278
    Abstract: Alcohols are produced in a practical and advantageous method, by the hydrogenation of a carbonyl compound under mild conditions, by reacting the carbonyl compounds with hydrogen in the presence of a bipyridyl derivative, a group VIII transition metal complex, and a base, or by reducing a carbonyl compound in the presence of a bipyridyl derivative, a group VIII transition metal complex, a base, and an alcoholic solvent.
    Type: Grant
    Filed: October 25, 2001
    Date of Patent: November 5, 2002
    Assignees: Japan Science and Technology Corporation, Takasago International Corporation
    Inventors: Hideyuki Ikehira, Kunihiko Murata, Eiji Katayama, Masami Kozawa, Toru Yokozawa, Takeshi Ohkuma, Takao Ikariya, Ryoji Noyori
  • Patent number: 6472571
    Abstract: Process for the production of organic compounds in a membrane reactor. Inorganic membranes composed of an inorganic backing layer and an inorganic interlayer are used in the membrane reactor. The inorganic interlayer may be modified with organic groups.
    Type: Grant
    Filed: October 2, 2000
    Date of Patent: October 29, 2002
    Assignee: Degussa-Huls AG
    Inventors: Andreas Karau, Jens Wöltinger, Olaf Burkhardt, Andreas Bommarius, Kai Boldt, Jean-Louis Philippe, Hans Henniges, Karlheinz Drauz
  • Patent number: 6462242
    Abstract: Benzyl alcohols, particularly those which bear fluorine substituents or fluoroalkyl substituents on the benzyl ring, can be obtained by formylation of corresponding aryl bromides to form benzaldehydes and reduction of the latter using further formate, wherein the benzaldehydes formed do not have to be isolated.
    Type: Grant
    Filed: June 5, 2000
    Date of Patent: October 8, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Torsten Neugebauer, Albrecht Marhold
  • Patent number: 6462206
    Abstract: Ketones and aldehydes are hydrogenated to the corresponding alcohol or alkyl group, using H2 gas as the stoichiometric reductant, and organometallic ruthenium complexes as the catalysts.
    Type: Grant
    Filed: June 20, 2001
    Date of Patent: October 8, 2002
    Assignees: E. I. du Pont de Nemours and Company, Brookhaven Science Associates
    Inventors: R. Morris Bullock, Marcel Schlaf, Elisabeth M. Hauptman
  • Publication number: 20020115884
    Abstract: A process for producing a hydrogenation product of aromatic carboxylic acid which comprises continuously producing the hydrogenation product of aromatic carboxylic acid by hydrogenating an aromatic carboxylic acid having a melting point of 250° C. or higher in a solvent in the presence of a solid catalyst, wherein the hydrogenation is conducted in a condition such that substantially the entire amount of the aromatic carboxylic acid of a raw material is dissolved in the solvent by recycling a portion of a reaction liquid taken out of a reactor into the reactor.
    Type: Application
    Filed: December 19, 2001
    Publication date: August 22, 2002
    Inventors: Hiroshi Machida, Ko Kedo, Fumiya Zaima
  • Publication number: 20020115889
    Abstract: The present invention relates to a process for preparing hydroxy-aromatics by oxidizing aromatics with dinitrogen monoxide in the gas phase in the presence of nanocrystalline zeolites.
    Type: Application
    Filed: July 24, 2001
    Publication date: August 22, 2002
    Inventors: Bernd Vogel, Elias Klemm, Mathias Seitz, Jochen Heller, Jorg Reiser
  • Patent number: 6410806
    Abstract: A reduction-treated copper-based catalyst obtained by reducing a copper-based catalyst with hydrogen in the presence of a liquid phase and a process for producing &agr;-phenylethyl alcohol, which comprises hydrogenating acetophenone in the presence of the same.
    Type: Grant
    Filed: January 18, 2001
    Date of Patent: June 25, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriaki Oku, Masaru Ishino
  • Patent number: 6399787
    Abstract: Novel transition metal catalysts with conformationally rigid chiral phosphines and phosphites are developed for asymmetric carbon-hydrogen and carbon—carbon bond formation. The invention emphasizes synthesis of chiral amines, &bgr;-amino acids and related compounds via catalytic asymmetric hydrogenation based on chiral monodentate and bidentate phosphines with cyclic ring structures. The ligands contain rigid ring structures.
    Type: Grant
    Filed: October 10, 2000
    Date of Patent: June 4, 2002
    Assignee: Penn State Research Foundation
    Inventor: Xumu Zhang
  • Patent number: 6392103
    Abstract: A process for the enantioselective reduction of prochiral ketones to chiral alcohols by (a) the reaction of a prochiral ketone with a silane agent, which is present in a stoichiometric quantity, in the presence of a catalyst derived from a Zn, Co or Cd precursor compound and from a chiral amine, imine, alcohol or amino alcohol ligand; (b) the hydrolysis of the siloxane obtained using an appropriate agent; and (c) the separation and purification of the optically active alcohol formed. Polymethylhydrosiloxane (PMHS) is a preferred silane agent, zinc is a preferred metal, and the precursor compound is produced by reacting a salt or complex of the respective metal with the reducing agent. In another embodiment, an appropriate salt of the chosen metal is used directly in the reaction with the chiral ligand to produce the catalytic form after reaction with the ligand. The process enables high enantiomeric excesses (ee) to be obtained in chiral alcohols.
    Type: Grant
    Filed: February 9, 2000
    Date of Patent: May 21, 2002
    Assignee: Firmenich SA
    Inventor: Hubert Mimoun
  • Patent number: 6362344
    Abstract: Chiral aminoalcohol catalysts and methods for their preparation are provided. The first catalyst is prepared via selective hydrogenation of one of two benzene rings in a precursor. The aminoalcohol promotes the asymmetric addition of organozinc reagents to aldehydes to afford optically active alcohols or their esters. The second catalyst is prepared by selective dialkylation of 3-exo-aminoisoborneol with a 2-haloethyl ether. The aminoalcohol promotes the addition of organozinc reagents to aliphatic aldehydes containing a &bgr;-branch with greatly enhanced enantioselectivity relative to DAIB.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: March 26, 2002
    Assignee: Bristol-Myers Squibb Pharma Company
    Inventor: William A. Nugent
  • Patent number: 6258909
    Abstract: A polymerizable vinylester composition is described which comprises at least three monomers and oligomers, said composition comprising: 2-95% by weight of: diaryl compounds comprising at least two aryl groups linked directly together or bridged by a linking group, each of said at least two aryl groups having a vinyl group attached thereto, 2-65% by weight of: a methacrylic acid ester of a vinyl-substituted sec-ethylol-diaryl oxide or its thioether or methine or biphenyl counterpart, and 1-35% by weight of: dimethacrylic acid esters of bis-[4-(1-hydroxyethyl)aryl] ether, thioether or methine, or their counterparts where aromatic rings are linked together directly, and 2-95% by weight of: unsaturated oligomers, and said reactive composition has less than 1% mol basis of monoaryl phenolic compounds.
    Type: Grant
    Filed: October 7, 1998
    Date of Patent: July 10, 2001
    Inventor: Boris A. Zaitsev
  • Patent number: 6245952
    Abstract: The present invention relates to a process for the preparation of alcohols by reduction of the carbonyl function in substrates belonging to the class of aldehydes, ketones, esters or lactones, which substrates may contain unsaturated functions other than carbonyl. This process includes the steps of reacting the carbonyl substrate with stoichiometric amounts of a silane in the presence of catalytic amounts of an active zinc compound which is monomeric and not a hydride, hydrolyzing the thus-obtained siloxane with a basic agent, and separating and purifying, if necessary, the thus-obtained alcohol. The catalytically active compound is generally obtained by the reaction of an oligomeric or polymeric precursor compound of zinc with a complexing agent.
    Type: Grant
    Filed: March 1, 1999
    Date of Patent: June 12, 2001
    Assignee: Firmenich SA
    Inventor: Hubert Mimoun
  • Patent number: 6218581
    Abstract: The present invention relates to a process of producing optically active alcohol having high optical purity by performing an enzyme conversion reaction on a raw material serving as the substrate, examples of which include racemic alcohol, ketone and the acylated form of a racemic alcohol, followed by hydrolysis as necessary, using as an optical separation catalyst a immobilized water-soluble protein extracted from inexpensive and safe grains or beans in order to solve the problems of the reaction process consisting of low yield due to the occurrence of side reactions, detrimental effects on the ecosystem and their accompanying cost burden, the need for aseptic procedures and the extended amount of time of subculturing, all of which are problems associated with production processes of optically active alcohols of the prior art that use microorganisms, microorganism enzymes, animal tissue enzymes and cultured plant cells.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: April 17, 2001
    Assignee: Sanyo Shokuhin Co., Ltd.
    Inventor: Hiroyuki Nagaoka
  • Patent number: 6218585
    Abstract: A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species (for example, a borohydride stabilized borane-tetrahydrofuran complex) catalyzed by a chiral catalyst includes the step of maintaining the concentration of borohydride species in the borane reagent below approximately 0.005 M during the reduction of the prochiral substrate. A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species that is catalyzed by a chiral catalyst includes the step of reducing the detrimental effect the borohydride species has on enantioselectivity by adding a Lewis acid. For example, the prochiral substrate can be a ketone and the chiral catalyst can be a chiral oxazaborolidine.
    Type: Grant
    Filed: April 20, 2000
    Date of Patent: April 17, 2001
    Assignee: Mine Safety Appliances Company
    Inventors: Karl Matos, Joseph A. Corella, II, Elizabeth R. Burkhardt, Shawn M. Nettles
  • Patent number: 6215030
    Abstract: Noble metal, particularly ruthenium, Raney catalysts which can hydrogenate (1) aromaticity-exhibiting ring portions of organic compounds, (2) carboxylic acids and their ester portions (carbonyl ester groups), (3) ring portions and carboxylic acid or their ester groups in compounds having such ring portions and carboxylic acid or their ester portions, and (4) ring portions and nitrile groups of aromatic nitrile compounds and methods for the preparation of corresponding hydrogenated compounds. The methods allow preparation of hydrogenated compounds having hydrogenated aromatic ring portions, hydrogenated carbonyl ester groups, hydrogenated aromatic ring and carbonyl ester groups, or hydrogenated aromatic rings and nitrile groups under milder hydrogen pressure and temperature conditions than the conventional catalysts.
    Type: Grant
    Filed: November 30, 1999
    Date of Patent: April 10, 2001
    Assignee: Showa Denko K.K.
    Inventors: Kouhei Morikawa, Shuuji Hirayama, Yoshimasa Ishimura, Yuseki Suyama, Tsutomu Nozawa, Hiroyuki Monzen, Motoo Miura, Kuniomi Marumo, Taketoshi Naito
  • Patent number: 6207865
    Abstract: A carbonyl compound or a mixture of two or more carbonyl compounds is catalytically hydrogenated in the presence of a Raney copper catalyst in the form of nuggets.
    Type: Grant
    Filed: January 11, 2000
    Date of Patent: March 27, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Boris Breitscheidel, Marc Walter, Detlef Kratz, Gerhard Schulz, Manfred Sauerwald
  • Patent number: 6207868
    Abstract: This invention is to develop novel transition metal catalysts for the practical synthesis of important chiral molecules. The invention emphasizes asymmetric catalysis based on chiral bidentate phosphine ligands with cyclic ring structures which could be used to restrict conformational flexibility of the ligands and thus the efficiency of chiral transfer can be enhanced through the ligand rigidity.
    Type: Grant
    Filed: November 12, 1998
    Date of Patent: March 27, 2001
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Patent number: 6187966
    Abstract: A process for preparing optically active alcoholic compounds wherein a carbonyl compound is assymmetrically reduced in an economical and practical manner. The process comprises treating a prochiral carbonyl compound represented by the general formula (1) with an optically active organoaluminum compound represented by the general formula (2) to conduct asymmetric reduction, thereby preparing an optically active alcoholic compound represented by the general formula (3).
    Type: Grant
    Filed: July 15, 1999
    Date of Patent: February 13, 2001
    Assignee: Kaneka Corporation
    Inventors: Tadashi Sugawa, Kenji Inoue, Kazunori Kan
  • Patent number: 6184381
    Abstract: This document describes a novel and practically excellent process for the preparation of optically active compounds, such as optically active alcohols or amines which are useful for various applications, for example, as synthetic intermediates of pharmaceuticals, liquid crystal materials, and reagents for optical resolution, wherein a hydrogen transfer type asymmetric reduction is carried out in the presence of both a transition metal complex and an optically active nitrogen compound or a transition metal complex having an optically active nitrogen compounds as an asymmetric ligand, and a hydrogen-donating organic or inorganic compound.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: February 6, 2001
    Assignees: Japan Science & Technology Corp., NKK Corp., Takeda Chemical Industries, Asahi Kasei Kogyo Kabushiki Kaisha, Takasago Intl. Corp.
    Inventors: Takao Ikariya, Shohei Hashiguchi, Jun Takehara, Nobuyuki Uematsu, Kazuhiko Matsumura, Ryoji Noyori, Akio Fujii
  • Patent number: 6180837
    Abstract: The invention involves a procedure for the catalytic enantioselective reduction of ketones to chiral alcohols. Heretofore, this reaction was carried out batch-wise. Because, in this procedure, one utilizes a catalyst increased in size with polymer, it is possible to carry out the reaction in a quasi-continuous manner in a membrane reactor. In contrast to the state of the art, one thus dramatically increases the operative life of the catalyst.
    Type: Grant
    Filed: July 13, 1999
    Date of Patent: January 30, 2001
    Assignees: Degussa-Huels AG, Forschungszentrum Julich GmbH
    Inventors: Guido Giffels, Marcel Felder, Udo Kragl, Christian Wandrey, Andreas Bommarius, Carsten Bolm, Nadine Derrien, Karlheinz Drauz
  • Patent number: 6166269
    Abstract: The present invention provides an improved process for the preparation of 2-phenyl ethanol [CAS 60-12-8] by catalytic hydrogenation of styrene oxide [CAS 96-09-3] with supported platinum group metal catalysts in the presence of an organic as well as inorganic base as a promoter, using alcohol as a solvent. The reaction is carried out at a temperature ranging between 40-120.degree. C. and the hydrogen pressure of 50-800 psig, under stirring conditions. After the reaction is complete, the reaction mixture is cooled to room temperature, catalyst is separated from the product by conventional methods like filtration. This invention is particularly useful as an alternative to the conventional methods like Grignard synthesis and Friedel-Craft alkylation for manufacture of 2-phenyl ethanol. This invention eliminates the handling of dangerous diethyl ether solvent, ethylene oxide and the use of AlCl.sub.3 which poses serious effluent problems.
    Type: Grant
    Filed: February 24, 1999
    Date of Patent: December 26, 2000
    Assignee: Council of Scientific and Industrial Resesearch
    Inventors: Raghunath Vitthal Chaudhari, Manisha Madhukar Telkar, Chandrashekhar Vasant Rode
  • Patent number: 6166260
    Abstract: The present invention relates to a tandem process of reduction and host-guest complexation using metal-hydride complexes to reduce chemical entities bearing carbonyl groups or their equivalents, and host-guest complexation to achieve improved optical resolution of the reduction product. In the complexation step, the reduction product is optically resolved via inclusion into the crystalline complex where it resides as guest and another complex component acts as host. Additional crystallization stages are performed if further improvements in the enantiomeric excess is desired.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: December 26, 2000
    Assignee: Zeeland Chemicals, Inc.
    Inventor: Glenn L. Heise
  • Patent number: 6166257
    Abstract: The present invention relates to a process for the asymmetric hydrogenation of a ketonic compound and derivative.The invention relates to the use of optically active metal complexes as catalysts for the asymmetric hydrogenation of a ketonic compound and derivative.
    Type: Grant
    Filed: March 24, 1999
    Date of Patent: December 26, 2000
    Assignee: Rhodia Chimie
    Inventors: Francois Mathey, Frederic Robin, Francois Mercier, Michel Spagnol
  • Patent number: 6156940
    Abstract: The present invention relates to a process for producing optically active halomethyl phenyl carbinols of the formula (1), comprising reducing halomethyl phenyl ketones of the formula (2) using an asymmetric reducing agent obtained from boranes and optically active .alpha.-phenyl-substituted-.beta.-amino alcohols of the formula (3) or optically active .alpha.-non-substituted-.beta.-amino alcohols of the formula (4).The present invention further relates to a process for producing optically active carbinols, comprising reacting a prochiral ketone with, an asymmetric reducing agent obtained from optically active .beta.-amino alcohols of the formula (5), a metal boron hydride and Lewis acid or lower dialkyl sulfuric acid. All of the formulas (1) to (5) are the same as shown in the specification.
    Type: Grant
    Filed: April 8, 1998
    Date of Patent: December 5, 2000
    Assignees: Sumika Fine Chemicals Company, Limited, Sumitomo Chemical Company, Limited
    Inventors: Kenji Saito, Norio Kometani, Azusa Fujiwara, Yukio Yoneyoshi, Gohfu Suzukamo
  • Patent number: 6150567
    Abstract: The present invention provides a process for reducing carbonyl compounds to hydroxy compounds, in particular stereoselectively reducing .alpha.-aminohaloketone derivatives, under mild conditions in an easy and simple manner, which comprises reacting a carbonyl compound of the general formula (1) with an organoaluminum compound of the general formula (4) to provide the corresponding alcohol compound of the general formula (5).
    Type: Grant
    Filed: December 29, 1997
    Date of Patent: November 21, 2000
    Assignee: Kaneka Corporation
    Inventors: Tadashi Sugawa, Tadashi Moroshima, Kenji Inoue, Kazunori Kan
  • Patent number: 6127581
    Abstract: Fluorinated benzaldehydes are obtainable in a simple and inexpensive manner and in significantly improved yields when chlorinated benzaldehydes are reacted with alkali metal fluorides at temperatures in the range from about 130 to 200.degree. C. in the presence of less than about 2 mol % of quaternary phosphonium salts, based on chlorine atoms to be replaced, at initial concentrations of more than 2.5 mol of the chlorinated benzaldehydes per kg of dipolar aprotic solvent. Fluorinated benzaldehydes obtained in this way can advantageously be hydrogenated with hydrogen in the presence of noble metal catalysts to give fluorinated benzyl alcohols.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: October 3, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Wiedemann, Albrecht Marhold, Claus Dreisbach
  • Patent number: 6124509
    Abstract: The present invention is a process for the catalytic hydrogenation of ketones and aldehydes to alcohols at low temperatures and pressures using organometallic molybdenum and tungsten complexes. The functional group is selected from groups represented by the formulas R(C.dbd.O)R' and R(C.dbd.O)H, wherein R and R' are selected from hydrogen or any alkyl or aryl group. The active catalyst for the process has the form: [CpM(CO).sub.2 (PR*.sub.3) L].sup.+ A.sup.-, where Cp=.eta..sup.5 -R.sup..tangle-solidup..sub.m C.sub.5 H.sub.5-m and R.sup..tangle-solidup. represents an alkyl group or a halogen (F, Cl, Br, I) or R.sup..tangle-solidup. =OR' (where R'=H, an alkyl group or an aryl group) or R.sup..tangle-solidup. =CO.sub.2 R' (where R'=H, an alkyl group or an aryl group) and m=0 to 5; M represents a molybdenum atom or a tungsten atom; R*.sub.3 represents three hydrocarbon groups selected from a cyclohexyl group (C.sub.6 H.sub.11), a methyl group (CH.sub.3), and a phenyl group (C.sub.6 H.sub.
    Type: Grant
    Filed: January 22, 1999
    Date of Patent: September 26, 2000
    Assignee: Brookhaven Science Associates
    Inventors: Mark Voges, R. Morris Bullock
  • Patent number: 6090950
    Abstract: Novel chiral boron and aluminum hydride complexes, compositions comprising the chiral hydride complexes, and methods for their synthesis and use are described. The novel chiral hydride complexes are of the formulas:MBH.sub.4-n-a (R*).sub.n (R').sub.a ;MBH.sub.2-b (R**) (R').sub.b ;MBH(R***);MBH(R*) (R");MAlH.sub.4-n-a (R*).sub.n (R').sub.a ;MAlH.sub.2-b (R**)(R').sub.b ;MAlH(R***); andMAlH(R*) (R"),whereinM is Na.sup.+, Li.sup.+ or K.sup.+ ;each R* is independently a monodentate chiral ligand;R** is a bidentate chiral ligand;R*** is a tridentate chiral ligand;R' is a monodentate achiral ligand;R" is a bidentate achiral ligand;n is 1-3;a is 0-2; andb is 0-1,with the proviso that n+a.ltoreq.3, and with the further proviso that when R** is S-BINOL, M is not Li.sup.+.
    Type: Grant
    Filed: August 23, 1996
    Date of Patent: July 18, 2000
    Assignee: Zeeland Chemicals, Inc.
    Inventor: Glenn L. Heise
  • Patent number: 6046127
    Abstract: Aldehydes, ketones, esters and lactones may be reduced using a reductant system consisting of a silane derivative and a metal hydride to give good yields of the corresponding alcohols. The reductant system used in the method enables preferential reduction of the carbonyl function. In one embodiment, the reductant system consists of polymethylhydroxysilane and a metal hydride, the hydride being prepared in situ or ex situ from a metal salt or complex by means of a reaction with a reducing agent.
    Type: Grant
    Filed: July 15, 1998
    Date of Patent: April 4, 2000
    Assignee: Firmenich SA
    Inventor: Hubert Mimoun
  • Patent number: 6046369
    Abstract: A process for producing .alpha.-phenylethyl alcohol, which comprises hydrogenating acetophenone by a fixed bed flow reaction in the presence of a catalyst, wherein the reaction is conducted in the state where the liquid hold up ratio in a reactor is in the range of from 30% to 90%.
    Type: Grant
    Filed: July 10, 1998
    Date of Patent: April 4, 2000
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Noriaki Oku, Masaru Ishino
  • Patent number: 6037505
    Abstract: The anantoselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the precence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulas (I) and (II). The compounds of formulas (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulas (I) and (II) may be generated in situ.
    Type: Grant
    Filed: April 26, 1999
    Date of Patent: March 14, 2000
    Assignee: Pfizer Inc.
    Inventor: George Joseph Quallich
  • Patent number: 6025531
    Abstract: A process for preparing an optically active alcohol by reacting a prochiral ketone corresponding to the optically active alcohol and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride; or obtained from the optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine and (2) a metal borohydride; and a process for preparing an optically active amine by reacting an oxime derivative and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride, or obtained from said optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine, and (2) a metal borohydride.
    Type: Grant
    Filed: June 3, 1998
    Date of Patent: February 15, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukio Yoneyoshi, Naoto Konya, Gohfu Suzukamo
  • Patent number: 6020517
    Abstract: A process for producing a fluorinated benzonitrile comprising hydrogenolyzing a fluorinated dicyanobenzene substituted with 1 to 4 fluorine atoms and having the remainder which may be substituted with a chlorine atom in the presence of a catalyst to cause hydrodecyanation of only the cyano group of one side and a process for producing a fluorinated benzyl alcohol comprising reducing the fluorinated benzonitrile and hydrolyzing the fluorinated benzonitrile and reducing the resultant corresponding fluorinated benzoic acid to convert the cyano group to a hydroxymethyl group.
    Type: Grant
    Filed: April 27, 1998
    Date of Patent: February 1, 2000
    Assignee: Showa Denko K.K.
    Inventors: Hiroyuki Monzen, Katsutoshi Morinaka, Hideo Miyata, Tsutomu Nozawa, Haruaki Ito, Kohei Morikawa
  • Patent number: 6015927
    Abstract: Substituted or unsubstituted cyclohexanones are advantageously prepared by hydrogenation of the corresponding phenols in the presence of a palladium-on-carbon catalyst at from 100 to 250.degree. C. and from 1 to 20 bar of hydrogen pressure if the reaction is carried out in the presence of straight-chain, branched or cyclic alkanes having a boiling point at atmospheric pressure of over 70.degree. C. as solvents. This makes it possible to obtain substituted or unsubstituted cyclohexanones in short hydrogenation times and in high yields using low-toxicity, physically problem-free solvents which are easy to handle from a safety point of view.
    Type: Grant
    Filed: June 29, 1998
    Date of Patent: January 18, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wolfgang Kiel
  • Patent number: 6005133
    Abstract: The enantioselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the presence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulae (I) and (II). The compounds of formulae (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulae (I) and (II) may be generated in situ.
    Type: Grant
    Filed: October 10, 1995
    Date of Patent: December 21, 1999
    Assignee: Pfizer Inc.
    Inventor: George Joseph Quallich
  • Patent number: 6002054
    Abstract: A method for producing an alcohol comprising the steps of continuously feeding starting materials of an alcohol; and carrying out catalytic reduction reaction of the starting materials in the presence of a hydrogenation catalyst, wherein said starting materials of an alcohol and a hydrogen gas are fed in a gaseous state or a mixture of liquid and gaseous states in a reduction reactor, and wherein said catalytic reduction reaction of the starting materials is carried out under temperature conditions, pressure conditions, and conditions of a molar ratio of hydrogen ((hydrogen molecules/(acyl groups in the starting materials)), sufficient to give an evaporation ratio of the starting materials of from 20 to 80% by weight, and wherein a ratio of VG to VL satisfies the following relationship in the reduction reactor: 100.ltoreq.VG/VL.ltoreq.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: December 14, 1999
    Assignee: Kao Corporation
    Inventors: Hideaki Ueoka, Futoshi Nishigaki, Osamu Tabata
  • Patent number: 5929284
    Abstract: Processes for efficiently producing .alpha.-halo ketones, .alpha.-halohydrins and epoxides on an industrial scale. The prosesses include one for producing an .alpha.-halo ketone of general formula (3) by decarboxylating a product of reaction between a carboxilic acid derivative of general formula (1) and a metal enolate prepared from an .alpha.-haloacetic acid of general formula (2) or an acceptable salt thereof, one for producing an by reducing the .alpha.-halo ketone (3), and one for producing an epoxide (13) by treating the .alpha.-halohydrin (11) with a base to effect ring closure. The above prosesses are particularly suitable for producing optically active .alpha.-halo ketones, .alpha.-halohydrins and epoxides from the corresponding .alpha.-amino acid derivatives.
    Type: Grant
    Filed: December 18, 1996
    Date of Patent: July 27, 1999
    Assignee: Kaneka Corporation
    Inventors: Akira Nishiyama, Tadashi Sugawa, Hajime Manabe, Kenji Inoue, Noritaka Yoshida
  • Patent number: 5852221
    Abstract: An optically active .beta.-aminoalkoxyborane complex of the formula (I): ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.11 aralkyl or C.sub.6 -C.sub.10 aryl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.7 -C.sub.11 aralkyl, or R.sup.1 and R.sup.2 together form (CH.sub.2)n wherein n is 3 or 4, and Ar is naphthyl, anthryl or phenanthryl, which may be substituted by from 1 to 3 substituents selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, C.sub.1 -C.sub.6 alkoxy and styrene polymer substituents.
    Type: Grant
    Filed: April 29, 1997
    Date of Patent: December 22, 1998
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Hiroshi Kashihara, Mikio Suzuki, Yoshio Ohara
  • Patent number: 5831132
    Abstract: The present invention relates to a process for producing optically active halomethyl phenyl carbinols of the formula (1), comprising reducing halomethyl phenyl ketones of the formula (2) using an asymmetric reducing agent obtained from boranes and optically active .alpha.-phenyl-substituted-.beta.-amino alcohols of the formula (3) or optically active .alpha.-non-substituted-.beta.-amino alcohols of the formula (4).The present invention further relates to a process for producing optically active carbinols, comprising reacting a prochiral keytone with an asymmetric reducing agent obtained from optically active .beta.-amino alcohols of the formula (5), a metal boron hydride and Lewis acid or lower dialkyl sulfuric acid. All of the formulas (1) to (5) are the same as shown in the specification.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: November 3, 1998
    Assignees: Sumika Fine Chemicals Company, Ltd., Sumitomo Chemical Company, Ltd.
    Inventors: Kenji Saito, Norio Kometani, Azusa Fujiwara, Yukio Yoneyoshi, Gohfu Suzukamo
  • Patent number: 5831133
    Abstract: Aldehydes, ketones, esters and lactones may be reduced using a reductant system consisting of polymethylhydroxysilane (PMHS) and a metal hydride to give good yields of the corresponding alcohols. The reductant system used in the method enables preferential reduction of the carbonyl function.
    Type: Grant
    Filed: May 15, 1996
    Date of Patent: November 3, 1998
    Assignee: Firmenich SA
    Inventor: Hubert Mimoun
  • Patent number: 5780692
    Abstract: A process for producing a benzhydrol compound (II) which comprises hydrogenating a benzophenone compound (I) in the presence of a hydrogenation catalyst consisting of a transition metal complex, a base and an optically active diamine compound: ##STR1## wherein R.sup.1 to R.sup.10 each represents H, OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkanoyl, etc., R.sup.2 and R.sup.3, and R.sup.8 and R.sup.9 may form --CH.dbd.CH--CH.dbd.CH--, or any two of R.sup.1 to R.sup.9 adjacent to each other may be bonded to thereby form --OCH.sub.2 O-- or --(CH.sub.2).sub.3 --. By using this process, optically active benzhydrol compounds which have a high purity and are useful as, for example, intermediates in the synthesis of drugs can be produced by simple procedures.
    Type: Grant
    Filed: December 24, 1996
    Date of Patent: July 14, 1998
    Assignee: Takasago International Corporation
    Inventors: Minzo Sakaguchi, Takashi Imai, Takashi Miura, Tetsuro Yamazaki
  • Patent number: 5763688
    Abstract: The present invention provides a method for producing a alcohol including an optically active alcohol by hydrogenating a carbonyl compound in the presence of a homogeneous catalyst, a base and a nitrogen-containing organic compound. Thus, the reaction employs an inexpensive catalyst and proceeds in high yield and high efficiency.
    Type: Grant
    Filed: December 7, 1995
    Date of Patent: June 9, 1998
    Assignee: Research Development Corporation of Japan
    Inventors: Takao Ikariya, Takeshi Ohkuma, Hirohito Ooka, Shohei Hashiguchi, Nobuo Seido, Ryoji Noyori
  • Patent number: 5756863
    Abstract: A process for producing an optically active cyclohexanol derivative represented by formula (I): ##STR1## wherein R.sup.1 represents an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, or a protected hydroxyl group, comprising asymmetrically hydrogenating a cyclohexanone derivative in the presence of a catalyst system composed of a transition metal compound (e.g., transition metal complex), a base (e.g., KOH), and a nitrogen compound (e.g., an amine compound).
    Type: Grant
    Filed: October 11, 1996
    Date of Patent: May 26, 1998
    Assignee: Takasago International Corporation
    Inventors: Toshiyuki Murayama, Takaji Matsumoto, Takashi Miura
  • Patent number: 5750802
    Abstract: A 1-phenyl-2-nitroalcohol of the formula I ##STR1## having a (1R*,2S*) stereoisomer and a (1R*2R*) stereoisomer is produced by reacting benzaldehyde with a nitroalkane in the presence of an amine catalyst. The resulting 1-phenyl-2-nitroalcohol includes at least 50% of the (1R*,2S*) stereoisomer.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: May 12, 1998
    Assignee: Amvac Chemical Corporation
    Inventor: C. Edward Baxter, Jr.
  • Patent number: 5750794
    Abstract: A process for preparing the chiral (4S)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is disclosed wherein racemic 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is asymmetrically reduced by contacting the racemic tetralone with an asymmetric reagent to produce a mixture of cis and trans alcohols, separating the cis from the trans alcohols, and oxidizing the (4S) enantiomer of the resulting cis and trans alcohols. Also disclosed are novel intermediates used in the synthesis of the above chiral tetralone.
    Type: Grant
    Filed: May 29, 1996
    Date of Patent: May 12, 1998
    Assignee: Pfizer Inc.
    Inventor: George J. Quallich
  • Patent number: 5731479
    Abstract: Optically active alcohols are prepared by reducing optically active carboxylic acids with hydrogen in the presence of ruthenium catalysts.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: March 24, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Stefan Antons
  • Patent number: 5663458
    Abstract: According to a process for producing .alpha.-phenylethyl alcohol by hydrogenation of acetophenone, which uses a copper-based catalyst containing at least one alkaline earth metal carbonate and/or at least one alkali metal compound, the hydrogenolysis of starting acetophenone is inhibited, and hence the production of ethylbenzene as a by-product is reduced, so that it becomes possible to produce .alpha.-phenylethyl alcohol useful as a starting material for styrene with high selectivity.
    Type: Grant
    Filed: November 29, 1995
    Date of Patent: September 2, 1997
    Assignee: Sumitomo Chemical Company, Limited.
    Inventors: Shinya Ito, Takuo Hibi
  • Patent number: 5639922
    Abstract: A process is described for the selective decomposition of aromatic primary hydroperoxides by contacting a hydroperoxide mixture containing aromatic primary hydroperoxides and aromatic tertiary hydroperoxides obtained by oxidation of alkylaromatic compounds under non-aqueous conditions with an alkali and an organic aromatic carboxylic acid salt.
    Type: Grant
    Filed: July 14, 1995
    Date of Patent: June 17, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoichi Ikeda, Motoo Hazama, Nobuhiro Kawara, Maki Okumura, Takanori Ito
  • Patent number: 5495054
    Abstract: A method for the enantioselective reduction of prochiral ketones using catalytic amounts of tetrahydroindeno[1,2-d][1,3,2] oxazaboroles of formula II is disclosed. ##STR1## The oxazaboroles can be generated in situ from the corresponding cis-1-amino-2-indanols or imino indanols (III) ##STR2## Novel compounds of formulas II and III are also disclosed.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: February 27, 1996
    Assignee: Sepracor, Inc.
    Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
  • Patent number: 5481048
    Abstract: A copper-containing hydrogenation reaction catalyst is prepared by reducing a precursor of a copper-containing catalyst usable in hydrogenation reaction with hydrogen gas or a mixture of hydrogen and an inert gas by liquid phase reduction in a stream of a solvent in the temperature range of from 50.degree. to 140.degree. C. An alcohol is produced using the catalyst thus obtained in a fixed bed continuous reaction system.
    Type: Grant
    Filed: December 13, 1994
    Date of Patent: January 2, 1996
    Assignee: Kao Corporation
    Inventors: Kiyoshi Tsukada, Yasuyuki Hattori, Taku Mimura