Preparing By Reduction Or Dehydrogenation (e.g., By Hydrogenation, Etc.) Patents (Class 568/772)
  • Patent number: 10252995
    Abstract: The present invention provides a method for producing 1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine or a salt thereof, the method including the step of heating hydroquinone and 4-(4-trifluoromethoxyphenoxy)piperidine. This method can produce 1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine or a salt thereof in an industrially advantageous manner.
    Type: Grant
    Filed: March 25, 2016
    Date of Patent: April 9, 2019
    Assignee: OTSUKA PHARMACEUTICAL CO., LTD.
    Inventors: Masahiro Miyake, Aya Asahina, Takahiro Okada
  • Patent number: 9035107
    Abstract: In a process for the dehydrogenation of dehydrogenatable hydrocarbons, a feed comprising dehydrogenatable hydrocarbons is contacted with a catalyst comprising a support and a dehydrogenation component under dehydrogenation conditions effective to convert at least a portion of the dehydrogenatable hydrocarbons in the feed. The catalyst is produced by a method comprising treating the support with a liquid composition comprising the dehydrogenation component or a precursor thereof and at least one organic dispersant selected from an amino alcohol and an amino acid.
    Type: Grant
    Filed: December 17, 2010
    Date of Patent: May 19, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Teng Xu, Stuart L. Soled, Edward A. Lemon, Joseph E. Baumgartner, Sabato Miseo, George H. Gamble
  • Patent number: 9029611
    Abstract: In a process for the dehydrogenation of cyclohexanone to produce phenol, a feed comprising cyclohexanone is contacted with a dehydrogenation catalyst under dehydrogenation conditions comprising a temperature of less than 400° C. and a pressure of less than 690 kPa, gauge, such 0.1 to 50 wt % of the cyclohexanone in said feed is converted to phenol and the dehydrogenation product contains less than 100 ppm by weight of alkylbenzenes.
    Type: Grant
    Filed: December 17, 2010
    Date of Patent: May 12, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Teng Xu, Jihad M. Dakka, Christopher L. Becker, Keith H. Kuechler, Francisco M. Benitez, Charles M. Smith, Hari Nair
  • Patent number: 8822738
    Abstract: A process for preparing hydroxytyrosol, wherein a compound where X is CH2OH or CH2OM (M=Li, Na, K, Mg, Ca), R1 and R2 are identical or different and are C1-C8 alkyl radical, benzyl radical, alkyl- or halogen-substituted benzyl radical or arylalkyl radical, where R1 and R2 can also be linked via to give a ring, R3, R4, R5 and R6 are identical or different and are hydrogen or C1-C6 alkyl radical, aryl radical, alkyl-substituted aryl radical, where R5 and R6 can also be linked via —(CH2)4—, —(CH2)5— or —(CH2)6— to give a ring, is reacted with an aluminum compound AlR7R8R9 (2), where R7, R8 and R9 are identical or different and are H or C1-C8 alkyl radical, and then an aqueous solution of a hydroxycarboxylic acid is added to form a clear homogeneous acidic solution with a pH<3, and hydroxytyrosol is extracted therefrom.
    Type: Grant
    Filed: February 25, 2014
    Date of Patent: September 2, 2014
    Assignee: Wacker Chemie AG
    Inventors: Benno Krueger, Gerald Fleischmann, Hermann Petersen
  • Patent number: 8637713
    Abstract: A catalytic process for the preparation of optically active compounds and their conversion thereafter to desired drug substances. In particular, the process relates to the preparation of (S)-3-(1-Dimethylamino-ethyl)-phenol using asymmetric catalytic reduction and transfer hydrogenation, thereby providing an improved route to forming drug substances such as rivastigimine and rivastigimine hydrogen tartrate.
    Type: Grant
    Filed: December 5, 2012
    Date of Patent: January 28, 2014
    Assignee: Novartis AG
    Inventors: Christian Mathes, Michael Foulkes, Martin Kesselgruber
  • Patent number: 8604253
    Abstract: The present invention is a method for producing a polyhydric phenol, including the following steps (a) to (d): (a) a first step of producing (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexcene-1-one from 2-deoxy-scyllo-inosose by a dehydration reaction; (b) a second step of producing 1,2,4-trihydroxybenzene from the (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one obtained in the first step by a dehydration reaction; (c) a third step of producing 4-hydroxycyclohexane-1,3-dione from the 1,2,4-trihydroxybenzene by a catalytic hydrogenation reaction with the use of a metal catalyst; and (d) a fourth step of producing hydroquinone by heating the 4-hydroxycyclohexane-1,3-dione.
    Type: Grant
    Filed: April 27, 2010
    Date of Patent: December 10, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hideo Kitagawa, Junya Kiyosu, Susumu Saito, Takaomi Hayashi, Naritoshi Yoshimura, Aya Nakagawa
  • Publication number: 20130225870
    Abstract: Methods of synthesizing 4-alkyl resorcinols and other substituted phenol compounds, according to formula (IV): or salts thereof, are disclosed, wherein the variables are defined herein.
    Type: Application
    Filed: August 25, 2010
    Publication date: August 29, 2013
    Applicant: SYNTA PHARMACEUTICALS CORP.
    Inventors: Chi-Wan Lee, Steven Bloom
  • Publication number: 20130096337
    Abstract: A catalytic process for the preparation of optically active compounds and their conversion thereafter to desired drug substances. In particular, the process relates to the preparation of (S)-3-(1-Dimethylamino-ethyl)-phenol using asymmetric catalytic reduction and transfer hydrogenation, thereby providing an improved route to forming drug substances such as rivastigimine and rivastigimine hydrogen tartrate.
    Type: Application
    Filed: December 5, 2012
    Publication date: April 18, 2013
    Applicant: Novartis AG
    Inventor: Novartis AG
  • Patent number: 8415508
    Abstract: A catalytic process for the preparation of optically active compounds and their conversion thereafter to desired drug substances. In particular, the process relates to the preparation of (S)-3-(1-Dimethylamino-ethyl)-phenol using asymmetric catalytic reduction and transfer hydrogenation, thereby providing an improved route to forming drug substances such as rivastigimine and rivastigimine hydrogen tartrate.
    Type: Grant
    Filed: December 17, 2009
    Date of Patent: April 9, 2013
    Assignee: Novartis AG
    Inventors: Christian Mathes, Michael Foulkes, Martin Kesselgruber
  • 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
  • Publication number: 20120046498
    Abstract: The present invention is a method for producing a polyhydric phenol, including the following steps (a) to (d): (a) a first step of producing (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexcene-1-one from 2-deoxy-scyllo-inosose by a dehydration reaction; (b) a second step of producing 1,2,4-trihydroxybenzene from the (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one obtained in the first step by a dehydration reaction; (c) a third step of producing 4-hydroxycyclohexane-1,3-dione from the 1,2,4-trihydroxybenzene by a catalytic hydrogenation reaction with the use of a metal catalyst; and (d) a fourth step of producing hydroquinone by heating the 4-hydroxycyclohexane-1,3-dione.
    Type: Application
    Filed: April 27, 2010
    Publication date: February 23, 2012
    Applicant: MITSUI CHEMICALS, INC.
    Inventors: Hideo Kitagawa, Junya Kiyosu, Susumu Saito, Takaomi Hayashi, Naritoshi Yoshimura, Aya Nakagawa
  • Patent number: 7718754
    Abstract: A promoter for a polycondensation reaction used together with a catalyst in a polycondensation reaction, the promoter for a polycondensation reaction comprising a pyrogallol compound having a benzene ring of which three hydrogen atoms adjacent to each other are substituted by hydroxyl groups; and a polycondensation resin obtained by polycondensing raw material monomers using the promoter as defined above and the catalyst. A polycondensation resin can be produced using the promoter of the present invention together with a catalyst in a polycondensation reaction, and the polycondensation resin can be used in various applications including, for example, films, sheets, fibers, toner materials for electrophotography, and the like.
    Type: Grant
    Filed: July 3, 2008
    Date of Patent: May 18, 2010
    Assignee: Kao Corporation
    Inventors: Eiji Shirai, Yoshitomo Kimura, Yasunori Inagaki, Takashi Kubo, Naoki Morita, Ryo Koike, Hiromi Iida
  • Patent number: 7230141
    Abstract: A process for preparing toluene derivatives of the formula I, where R1, R2 and R3 independently of one another are hydrogen, halogen, C1–C6-alkyl, hydroxyl or C1–C6-alkoxy, by hydrogenating benzaldehydes and/or benzyl alcohols of the formula II, with hydrogen in the presence of a catalyst, which is described in more detail in the description.
    Type: Grant
    Filed: January 20, 2003
    Date of Patent: June 12, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Nils Bottke, Rolf-Hartmuth Fischer, Thomas Nöbel, Markus Rösch
  • Patent number: 6911562
    Abstract: A process for the preparation of a compound of formula I: wherein R is a hydrogen or a C1-6 alkyl group which is straight chain, branched or cyclic, with or without an oxygen, nitrogen or sulphur heteroatom anywhere in the chain or ring by reacting a compound of formula II: with a source of hydrogen selected from either hydrogen or water in the presence of a mixture of at least two catalysts selected from nickel, raney nickel, and palladium, at a pH below 7.0 in a solvent medium comprising an alcohol having a carbon chain length of up to 3.
    Type: Grant
    Filed: July 8, 2004
    Date of Patent: June 28, 2005
    Assignee: Unilever Home & Personal Care USA division of Conopco, Inc.
    Inventors: Ramachandra Bhat, Vinodkumar Ramniranjan Dhanuka, Bijan Harichian
  • Patent number: 6806395
    Abstract: A process for producing a 3,5-bisalkylphenol (2) according to the following reaction scheme: (wherein R1 represents a hydrogen atom, an alkali metal atom, an alkaline earth metal atom, or a hydroxyl-protecting group (other than methyl group); R2 represents a C1 to C5 lower alkyl group or an optionally substituted phenyl group; and each of R3 and R4, which may be identical to or different from each other, represents a lower alkyl group, an aralkyl group, or an aryl group); a carbinol compound (1); and a process for producing the carbinol compound. The production process of the present invention enables efficient and safe production of a variety of 3,5-bisalkylphenols including 3,5-diisopropylphenol, which are important as synthesis intermediates for drugs and agricultural chemicals, in shorter steps at high purity in high yield, thus contributing to consistent supply of drugs and agricultural chemicals.
    Type: Grant
    Filed: March 18, 2003
    Date of Patent: October 19, 2004
    Assignee: Kowa Co., Ltd.
    Inventors: Kimiyuki Shibuya, Tadaaki Ohgiya, Toru Miura, Kazuhiro Onogi
  • Patent number: 6680414
    Abstract: The present invention provides a process, which includes: in a homogeneous liquid phase including water, and over a fixed-bed catalyst, continuously hydrogenating at least one hydroformylation product obtained from a hydroformylation of one or more C4-16 olefins to produce at least one output mixture; wherein the fixed-bed catalyst includes at least one element of transition group eight of the Periodic Table of the Elements; wherein the output mixture includes at least one corresponding alcohol and from 0.05 to 10% by weight of water; and wherein in a steady-state operation of the process, from 3 to 50% more hydrogen is fed to the hydrogenation than is consumed by the hydrogenation.
    Type: Grant
    Filed: December 14, 2001
    Date of Patent: January 20, 2004
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Cord Knoop, Bernhard Scholz, Alfred Kaizik, Dietmar Gubisch, Joachim Schuler, Walter Tötsch, Wilfried Büschken
  • Patent number: 6653509
    Abstract: A catalyst which consists of amorphous carbon with molecular planes that have curved surfaces and contain six-membered and non-six-membered carbon rings, optionally having at least one catalytically active, low-valency metal covalently bound thereto. Methods of producing the catalyst and applications thereof are included.
    Type: Grant
    Filed: April 15, 2002
    Date of Patent: November 25, 2003
    Assignee: Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.
    Inventors: Robert Schlögl, Michael Wohlers, Thilo Belz, Thomas Braun
  • Patent number: 6600078
    Abstract: A heterogeneous liquid-phase process for the hydrogenation of aldehydes of Formula (I) and (III) to the corresponding alcohols of Formula (II) and (IV) which process comprises contacting alcoholic or aqueous-alcoholic solution of aldehydes and hydrogen gas with a catalyst comprising a reduced mixture of CuO and ZnO in presence of a metal of group IIIA of the Periodic Table, such as aluminium, as a promoter at a temperature of between about 110° and 180° C. and a pressure of between about 20 and 500 psig.
    Type: Grant
    Filed: August 12, 2002
    Date of Patent: July 29, 2003
    Assignee: Saudi Basic Industries Corporation
    Inventors: Meftahuddin Mahmud, Ahmad Kamal Faizi, Vidyasagar Anchoori, Abdullah Al-Qahtani
  • Publication number: 20020142409
    Abstract: A bioengineered synthesis scheme for the production of quinic acid from a carbon source is provided. Methods of producing quinic acid from a earbon source based on the synthesis scheme as well as conversion of quinic acid to hydroquinone are also provided.
    Type: Application
    Filed: March 15, 2002
    Publication date: October 3, 2002
    Inventors: John W. Frost, Karen M. Frost
  • Patent number: 6420613
    Abstract: A method of preparing a reduced product by efficiently reducing an unsaturated organic compound by using, as a reducing agent, a trichlorosilane which is industrially cheaply available and is easy to handle, and a reducing agent therefor. A reduced product of an unsaturated organic compound is obtained by mixing the unsaturated organic compound and a trichlorosilane together to reduce the unsaturated organic compound in the presence of a compound that forms a silicon complex having five coordinations upon acting on the trichlorosilane such as an N-formylated product of a secondary amine having not less than 3 carbon atoms. The invention further provides a reducing agent comprising a particular silicon complex.
    Type: Grant
    Filed: December 11, 2000
    Date of Patent: July 16, 2002
    Assignee: Tokuyama Corporation
    Inventors: Fumiaki Iwasaki, Yoshihiro Matsumura, Osamu Onomura, Kenji Tanaka
  • Patent number: 6417409
    Abstract: The invention relates to an improved process for the production of 2,3,5-trimethylhydroquinone diesters by rearrangement of 2,6,6-trimethyl-2-cyclohexene-1,4-dione (4-oxoisophorone, ketoisophorone) in the presence of a dissolved, acidic catalyst and an acylating agent, such as for example carboxylic anhydrides or carboxylic acid halides. The 2,3,5-trimethylhydroquinone diester can optionally then be saponified to give free 2,3,5-trimethylhydroquinone (TMHQ), which is a valuable building block in the synthesis of vitamin E.
    Type: Grant
    Filed: February 11, 2000
    Date of Patent: July 9, 2002
    Assignee: Degussa-Huls AG
    Inventors: Steffen Krill, Klaus Huthmacher
  • Publication number: 20020004619
    Abstract: A process for preparing trimethylhydroquinone diacetate, with subsequent hydrolysis to give trimethylhydroquinone, the process including reacting 2,2,6-trimethylcyclohexane-1,4-dione under oxidative conditions, in the presence of a sulfonating agent and a strong acid, and in the presence of an acylating agent.
    Type: Application
    Filed: April 4, 2001
    Publication date: January 10, 2002
    Inventors: Steffen Krill, Klaus Huthmacher
  • Patent number: 6329535
    Abstract: A process for preparing esterified chroman compounds from 2,6,6-trimethylcylohex-2-ene-1,4-dione, wherein the esterified intermediates are reacted directly to give the desired chroman derivatives without an additional purification step.
    Type: Grant
    Filed: October 20, 2000
    Date of Patent: December 11, 2001
    Assignee: Degussa Dental GmbH & Co. KG
    Inventors: Horst Weigel, Steffen Krill, Hans Joachim Hasselbach, Klaus Huthmacher
  • Patent number: 6211418
    Abstract: An inexpensive method for producing trimethylhydroquinone free from the problem of the disposal of waste catalyst, which method comprises the steps of: (1) reacting isophorone in the presence of an acid catalyst and recovering &bgr;-isophorone by distillation, (2) oxidizing the &bgr;-isophorone in the presence of amorphous carbon and a base to obtain 4-oxoisophorone, (3) reacting the 4-oxoisophorone with an acid anhydride in a liquid phase or with a carboxylic acid in a vapor phase in the presence of a solid acid catalyst to obtain trimethylhydroquinones, and (4) hydrolyzing the trimethylhydroquinones to obtaining trimethylhydroquinone.
    Type: Grant
    Filed: July 28, 1998
    Date of Patent: April 3, 2001
    Assignee: Nippon Petrochemicals Company Limited
    Inventors: Kazuharu Suyama, Noboru Kiyota, Tomohiro Konishi, Yasuo Matsumura
  • Patent number: 6191323
    Abstract: A process for the reduction of ketones or aldehydes to alcohols has been developed. The process involves contacting the ketone or aldehyde with a primary or secondary alcohol and a catalyst at reduction conditions. The catalyst is a molecular sieve having the empirical formula: (MwSnxTiySi1-x-y-zGez)O2 where M is a trivalent metal such as aluminum or boron. These molecular sieves have a microporous three dimensional framework structure of at least SiO2 and SnO2 tetrahedral units, a crystallographically regular pore system and the characteristic x-ray diffraction pattern of zeolite beta.
    Type: Grant
    Filed: April 25, 2000
    Date of Patent: February 20, 2001
    Assignee: UOP LLC
    Inventors: Laszlo T. Nemeth, Avelino Corma Canos, Susana Valencia Valencia, Jaime G. Moscoso, Marcelo Eduardo Domine
  • Patent number: 6063968
    Abstract: The invention relates to an improved method for the production of 2,3,5-trimethylhydroquinone by rearranging 4-oxo-isophorone (keto-isophorone, 3,5,5-trimethylcyclohex-2-en[e]-1,4-dione) to a trimethylhydroquinone diester and by its subsequent saponification.
    Type: Grant
    Filed: May 14, 1997
    Date of Patent: May 16, 2000
    Assignee: Degussa Aktiengesellschaft
    Inventors: Frank Hubner, Steffen Krill, Bernd Drapal, Hermann Schmitt, Klaus Huthmacher, Herbert Tanner
  • Patent number: 6013844
    Abstract: A process for preparing catechol monoethers or catechols of the formula Ia or Ib ##STR1## where R.sup.1 and R.sup.2 are, independently of one another, hydrogen or C.sub.1 -C.sub.8 hydrocarbon radicals, and R.sup.3 is a C.sub.1 -C.sub.8 hydrocarbon radical, which comprises a 2-hydroxycyclohexanone dialkyl ketal of the formula II or a 2-alkoxycyclohexanone of the formula III ##STR2## a) being reacted in the gas phase in the presence of palladium on zirconium oxide as catalyst to obtain compounds Ia orb) carrying out stage a) in the presence of water to obtain compounds Ib.
    Type: Grant
    Filed: July 15, 1998
    Date of Patent: January 11, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Daniel Heineke, Uwe Dingerdissen, Joachim Wulff-Doring, Michael Hesse
  • Patent number: 5817890
    Abstract: The present invention relates to new fluorinated hexane compounds corresponding to the following general formula (II): ##STR1## in which X'.sub.2, X'.sub.3, and X'.sub.4 are the same or different, and denote a halogen or a pseudohalogen, preferably a halogen, more preferably chlorine and fluorine, with the condition that, when R.sub.1 is hydroxyl, cyano, amido, imido, ethoxy, benzyloxy, cyclohexyloxy and tert-butoxy, not all the halogens can simultaneously be chlorine and R.sub.4, R.sub.3 and R.sub.5 are simultaneously equal to H;R.sub.1 denotes a hydrogen, a hydrocarbon chain such as an alkyl chain, alkoxy, cycloalkyl ether, an aromatic group, aromatic ether or an alkoxy, carbonyl, carboxyl or acyloxy, cyano, amido, imido or hydroxyl group;R.sub.
    Type: Grant
    Filed: March 9, 1995
    Date of Patent: October 6, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Lucette Duhamel, Pierre Duhamel, Bertrand Leblond, Jean-Marie Poirier
  • Patent number: 5583268
    Abstract: A process of catalytically reacting a 3-18 carbon mono-olefin such as cyclohexene with an arylhydroxide such as phenol in the liquid phase forming an ortho-alkylated arylhydroxide which is subsequently catalytically dehydrogentated to form an ortho-alkenylarylhydroxide or ortho-arylarylhydroxide such as ortho-phenylphenol.
    Type: Grant
    Filed: December 15, 1995
    Date of Patent: December 10, 1996
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Dennis A. Hucul, Tracy L. Young, Kenneth A. Burdett
  • Patent number: 5563300
    Abstract: The present invention provides a unique and novel way of producing carbinols such as 4-hydroxyphenylmethylcarbinol (HPMC). In this new process, a ketone such as 4-hydroxyacetophenone (4-HAP) is heated under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable catalyst and a basic material, and for a sufficient period of time to form HPMC.
    Type: Grant
    Filed: December 7, 1995
    Date of Patent: October 8, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, Graham N. Mott, Charles B. Hilton, Mohammad Aslam
  • Patent number: 5545388
    Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: August 13, 1996
    Inventors: Charles J. Rogers, Alfred Kornel
  • Patent number: 5478548
    Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: December 26, 1995
    Inventors: Charles J. Rogers, Alfred Kornel
  • Patent number: 5435985
    Abstract: The invention relates to a hydrogenation catalyst for use in the preparation of hydrogen peroxide and to a method for the preparation of the catalyst. The hydrogenation catalyst contains in the main platinum group metal, of which more than 50 wt % is palladium. According to the invention, at least one additional metal is added to the platinum group metal.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: July 25, 1995
    Assignee: Kemira Oy
    Inventors: Arto Pukkinen, Lauri Heikkinen, Rauni Ruuska
  • Patent number: 5399785
    Abstract: Disclosed is a chemically stable tyrosinase activity inhibitor having high tyrosinase activity inhibition effect and low toxicity. The tyrosinase activity inhibitor has a structure of the formula: ##STR1## wherein R.sub.1, R.sub.3 and R.sub.4 are a hydrogen atom or an alkyl or alkenyl group having 1 to 9 carbon atoms, and R.sub.2 is an alkyl or alkenyl group having 2 to 9 carbon atoms.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: March 21, 1995
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Yasutaka Miura, Yasuhiro Kinoshita, Yoshikazu Yamamoto, Kunio Takahashi, Kiyotaka Koyama, Kaoru Takatori
  • Patent number: 5319148
    Abstract: The preparation of pyrocatechol monoethers or pyrocatechols of the formula Ia or Ib respectively ##STR1## ( R.sup.1 and R.sup.2 =H or C.sub.1 --C.sub.8 -hydrocarbon radicals; R.sup.3 =C.sub.1 --C.sub.8 -hydrocarbon radical ) by rearranging a 2-hydroxycyclohexanone dialkyl ketal II ##STR2## a) in the gas phase in the presence of a platinmetal or in the presence of a compound of one of these metals as catalyst in order to obtain a compound Ia, orb) carrying out step a) in the presence of water in order to obtain a compound Ib. The products are used as intermediates in the synthesis of pharmaceuticals, fragrances and flavors.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: June 7, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Karcher, Horst Zimmermann, Jochem Henkelmann
  • Patent number: 5276198
    Abstract: A process for producing 2-methyl-1,3-cyclohexanedione which comprises subjecting 1,3-cyclohexanedione, formaldehyde and a dialkylamine to Mannich reaction to obtain a 2-dialkylaminomethyl-1,3-cyclohexanedione, and subjecting the 2-dialkylaminomethyl to hydrogenolysis, and a process for producing 2-methylresorcinol which comprises aromatizing 2-methyl-1,3-cyclohexanedione obtained. According to these processes, it is possible to produce high-purity 2-methylresorcinol and 2-methyl-1,3-cyclohexanedione commercially easily and advantageously.
    Type: Grant
    Filed: August 21, 1992
    Date of Patent: January 4, 1994
    Assignees: Sumitomo Chemical Company, Limited, Sumika Fine Chemicals Co., Ltd.
    Inventors: Toshio Nakamatsu, Yasuhiro Nishida, Norio Kometani
  • Patent number: 5245084
    Abstract: The mixture consists of at least one organic peroxide, at least one hydroquinone derivative of the general formulae I and/or II and/or III ##STR1## wherein R and R.sup.1, which may be identical or different, stand for H or t-alkyl, and X stands, for example, for C.sub.1-18 -alkylene, and a crosslinkage promoter, and permits the crosslinkage of polymers and at the same time extends the scorch time, which must be understood as the processing time.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: September 14, 1993
    Assignee: Luperox GmbH
    Inventors: Jurgen Groepper, Harald Hofmann
  • Patent number: 5233095
    Abstract: A process for the manufacture of resorcinol is described which relies upon the intermediacy of a .alpha.,.beta.-unsaturated ketone which can be reacted with a hydroxy moiety-containing compound to obtain a resorcinol precursor which is subsequently converted to resorcinol. In a specific embodiment, 2-cyclohexenone is reacted with water to obtain 3-hydroxycyclohexanone which is dehydrogenated to resorcinol. In another embodiment, 2-cyclohexenone is oxidized to cyclohexane-1,3-dione which is dehydragenated obtain resorcinol.
    Type: Grant
    Filed: July 16, 1991
    Date of Patent: August 3, 1993
    Assignee: Catalytica, Inc.
    Inventors: Jere D. Fellmann, Robert J. Saxton, Paul Tung
  • Patent number: 4886891
    Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
  • Patent number: 4861921
    Abstract: A process for the manufacture of resorcinol is described which relies upon the intermediacy of a .alpha.,.beta.-unsaturated ketone which can be reacted with a hydroxy moiety-containing compound to obtain a resorcinol precursor which is subsequently converted to resorcinol. In a specific embodiment, 2-cyclohexenone is reacted dehydrogenated to resorcinol. In antoher embodiment, 2-cyclohexenone is oxidized to cyclohexane-1,3-dione which is dehydragenated obtain resorcinol.
    Type: Grant
    Filed: March 3, 1987
    Date of Patent: August 29, 1989
    Assignee: Catalytica Associates
    Inventors: Jere D. Fellmann, Robert J. Saxton, Paul Tung
  • Patent number: 4847429
    Abstract: Process is disclosed for the preparation of phenylhydroquinones by the alkylation of hydroquinone (or derivatives thereof) with the cyclohexyl moieties, cyclohexanol or cyclohexene (or derivatives thereof), followed by dehydrogenation of the intermediate cyclohexylhydroquinone.
    Type: Grant
    Filed: August 3, 1987
    Date of Patent: July 11, 1989
    Assignee: Eastman Kodak Company
    Inventors: Carl M. Lentz, Bruce L. Gustafson, Dale E. Van Sickle, Joseph S. Bowers, Jr.
  • Patent number: 4835278
    Abstract: A process is described for the preparation of a compound of formula (2) ##STR1## (wherein R is a C.sub.1-6 alkyl or a C.sub.7-20 aralkyl group) and the salts thereof, which comprises reducing a compound of formula (3) ##STR2## (or a salt thereof), using a reducing system comprising borohydride ions and metal ions selected from lanthanide ions, alkaline earth metal ions or yttrium ions in solution. The reduction system may be provided by a borohydride (e.g. NaBH.sub.4) and a metal salt (e.g. CeCl.sub.3).The ester (2) may then if desired be hydrolyzed to give the parent acid.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: May 30, 1989
    Assignee: Glaxo Group Limited
    Inventors: Roger Barrett, Clive A. Meerholz, Brian D. Judkins
  • Patent number: 4798911
    Abstract: A method for selective dehydrogenation of a compound, comprising contacting a compound of the formula ##STR1## wherein each R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is independently selected from the group consisting of H, (C.sub.1 -C.sub.20) alkyl, (C.sub.3 -C.sub.20) cycloalkyl, (C.sub.6 -C.sub.20) aryl, (C.sub.7 -C.sub.20) alkylaryl, (C.sub.7 -C.sub.20) aralkyl groups, as well as substituted (C.sub.1 -C.sub.20) alkyl, (C.sub.3 -C.sub.20) cycloalkyl, (C.sub.6 -C.sub.20) aryl, (C.sub.7 -C.sub.20) aralkyl and (C.sub.7 -C.sub.20) arylalkyl moieties, optionally further substituted with --OR, wherein R is R.sup.1, R.sup.2, R.sup.3 or R.sup.4 ; and wherein R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 may be joined as part of a ring structure, at a dehydrogenation temperature in the presence of a catalyst comprising about 0.01 wt %-19.9 wt % Pd and about 0.01 wt %-19.9 wt % Cu on a carbon support, wherein the total amount of (Pd+Cu) on the support is about 0.
    Type: Grant
    Filed: July 20, 1987
    Date of Patent: January 17, 1989
    Assignee: Eastman Kodak Company
    Inventors: Carl M. Lentz, Bruce L. Gustafson, Paul S. Wehner
  • Patent number: 4769500
    Abstract: A process for preparation of 2,3,5-trimethylhydroquinone (TMHQ) from 2,3,5-trimethylbenzoquinone (TMBQ) is disclosed, comprising reducing TMBQ with hydrogen in the presence of a platinum group metal catalyst with a silica alumina support containing an alkali metal component. This process permits preparation of TMHQ of purity as high as more than 99%.
    Type: Grant
    Filed: September 24, 1987
    Date of Patent: September 6, 1988
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomoyuki Yui, Akira Ito
  • Patent number: 4600799
    Abstract: 2,3,6-Trimethylhydroquinone is prepared by catalytic hydrogenation of 2,3,6-trimethylquinone with hydrogen in the presence of a solvent by a continuous process in which the reaction is carried out over a platinum/alumina catalyst.
    Type: Grant
    Filed: February 7, 1985
    Date of Patent: July 15, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz J. Broecker, Peter Tavs, Harald Laas, Wolf-Karlo Aders
  • Patent number: 4538009
    Abstract: Substituted phenols of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each hydrogen or an aliphatic or aromatic hydrocarbon radical, are prepared by dehydrogenating a cyclic alcohol of the general formula II ##STR2## or a cyclic ketone of the general formula III ##STR3## where one of the broken lines can be an additional C-C bond, in the gas phase at from 150.degree. to 380.degree. C. over a supported noble metal catalyst, by a process in which the dehydrogenation catalyst used is palladium or platinum on an aluminum spinel carrier, in particular an aluminum spinel which has a BET specific surface area of from 5 to 150 m.sup.2 /g or, for the dehydrogenation of cyclohexenones, preferably from 10 to 50 m.sup.2 /g. Particularly suitable aluminum spinels are those which, in addition to aluminum, contain magnesium, zinc, cobalt or nickel.
    Type: Grant
    Filed: April 12, 1984
    Date of Patent: August 27, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Goetz, Harald Laas, Peter Tavs, Leopold Hupfer, Karl Baer
  • Patent number: 4536347
    Abstract: Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha., .beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing.The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the soughtafter fragrances geraniol and nerol.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: August 20, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Matthias Irgang
  • Patent number: 4503249
    Abstract: Iron (II) hexacyanocobaltate and ruthenium (III) hexacyanocobaltate have been found to be useful in the catalytic hydrogenation of organic materials.
    Type: Grant
    Filed: September 21, 1982
    Date of Patent: March 5, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Gerhard P. Nowack, Marvin M. Johnson, Donald C. Tabler
  • Patent number: 4482756
    Abstract: A process for making a hydroquinone from phenol or substituted phenol wherein the phenol is oxidized in the presence of a copper catalyst to a p-benzoquinone compound and the p-benzoquinone compound is directly hydrogenated without additional catalyst to the corresponding hydroquinone.
    Type: Grant
    Filed: July 5, 1983
    Date of Patent: November 13, 1984
    Assignee: Sun Tech, Inc.
    Inventors: Chao-Yang Hsu, James E. Lyons
  • Patent number: 4453025
    Abstract: Isophorone is converted to 3,5-xylenol in the vapor phase in the presence of a heterogeneous catalyst comprising a particular combination of multiple rare earth metals on an alumina support or one or more rare earth metals in combination with one or more transition metals and/or one or more alkali or alkaline earth metals. Particularly good results are obtained with a catalyst comprising a naturally-occurring mixture of rare earth metals known as didymium in combination with potassium and cobalt promoters.
    Type: Grant
    Filed: November 23, 1982
    Date of Patent: June 5, 1984
    Assignee: Shell Oil Company
    Inventors: Antonius J. C. Van Seters, Freddy Wattimena