Preparing By Reduction Or Dehydrogenation (e.g., By Hydrogenation, Etc.) Patents (Class 568/772)
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Patent number: 10252995Abstract: 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: GrantFiled: March 25, 2016Date of Patent: April 9, 2019Assignee: OTSUKA PHARMACEUTICAL CO., LTD.Inventors: Masahiro Miyake, Aya Asahina, Takahiro Okada
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Patent number: 9035107Abstract: 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: GrantFiled: December 17, 2010Date of Patent: May 19, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Teng Xu, Stuart L. Soled, Edward A. Lemon, Joseph E. Baumgartner, Sabato Miseo, George H. Gamble
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Patent number: 9029611Abstract: 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: GrantFiled: December 17, 2010Date of Patent: May 12, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Teng Xu, Jihad M. Dakka, Christopher L. Becker, Keith H. Kuechler, Francisco M. Benitez, Charles M. Smith, Hari Nair
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Patent number: 8822738Abstract: 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: GrantFiled: February 25, 2014Date of Patent: September 2, 2014Assignee: Wacker Chemie AGInventors: Benno Krueger, Gerald Fleischmann, Hermann Petersen
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Patent number: 8637713Abstract: 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: GrantFiled: December 5, 2012Date of Patent: January 28, 2014Assignee: Novartis AGInventors: Christian Mathes, Michael Foulkes, Martin Kesselgruber
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Patent number: 8604253Abstract: 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: GrantFiled: April 27, 2010Date of Patent: December 10, 2013Assignee: Mitsui Chemicals, Inc.Inventors: Hideo Kitagawa, Junya Kiyosu, Susumu Saito, Takaomi Hayashi, Naritoshi Yoshimura, Aya Nakagawa
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Publication number: 20130225870Abstract: 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: ApplicationFiled: August 25, 2010Publication date: August 29, 2013Applicant: SYNTA PHARMACEUTICALS CORP.Inventors: Chi-Wan Lee, Steven Bloom
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Publication number: 20130096337Abstract: 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: ApplicationFiled: December 5, 2012Publication date: April 18, 2013Applicant: Novartis AGInventor: Novartis AG
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Patent number: 8415508Abstract: 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: GrantFiled: December 17, 2009Date of Patent: April 9, 2013Assignee: Novartis AGInventors: Christian Mathes, Michael Foulkes, Martin Kesselgruber
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Publication number: 20130053574Abstract: 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: ApplicationFiled: April 16, 2012Publication date: February 28, 2013Applicant: NIPPON CHEMICAL INDUSTRIAL CO., LTD.Inventors: Wanbin Zhang, Delong Liu, Hui Guo, Yangang Liu
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Publication number: 20120046498Abstract: 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: ApplicationFiled: April 27, 2010Publication date: February 23, 2012Applicant: MITSUI CHEMICALS, INC.Inventors: Hideo Kitagawa, Junya Kiyosu, Susumu Saito, Takaomi Hayashi, Naritoshi Yoshimura, Aya Nakagawa
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Patent number: 7718754Abstract: 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: GrantFiled: July 3, 2008Date of Patent: May 18, 2010Assignee: Kao CorporationInventors: Eiji Shirai, Yoshitomo Kimura, Yasunori Inagaki, Takashi Kubo, Naoki Morita, Ryo Koike, Hiromi Iida
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Patent number: 7230141Abstract: 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: GrantFiled: January 20, 2003Date of Patent: June 12, 2007Assignee: BASF AktiengesellschaftInventors: Nils Bottke, Rolf-Hartmuth Fischer, Thomas Nöbel, Markus Rösch
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Patent number: 6911562Abstract: 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: GrantFiled: July 8, 2004Date of Patent: June 28, 2005Assignee: Unilever Home & Personal Care USA division of Conopco, Inc.Inventors: Ramachandra Bhat, Vinodkumar Ramniranjan Dhanuka, Bijan Harichian
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Patent number: 6806395Abstract: 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: GrantFiled: March 18, 2003Date of Patent: October 19, 2004Assignee: Kowa Co., Ltd.Inventors: Kimiyuki Shibuya, Tadaaki Ohgiya, Toru Miura, Kazuhiro Onogi
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Patent number: 6680414Abstract: 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: GrantFiled: December 14, 2001Date of Patent: January 20, 2004Assignee: Oxeno Olefinchemie GmbHInventors: Cord Knoop, Bernhard Scholz, Alfred Kaizik, Dietmar Gubisch, Joachim Schuler, Walter Tötsch, Wilfried Büschken
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Patent number: 6653509Abstract: 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: GrantFiled: April 15, 2002Date of Patent: November 25, 2003Assignee: Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.Inventors: Robert Schlögl, Michael Wohlers, Thilo Belz, Thomas Braun
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Patent number: 6600078Abstract: 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: GrantFiled: August 12, 2002Date of Patent: July 29, 2003Assignee: Saudi Basic Industries CorporationInventors: Meftahuddin Mahmud, Ahmad Kamal Faizi, Vidyasagar Anchoori, Abdullah Al-Qahtani
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Publication number: 20020142409Abstract: 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: ApplicationFiled: March 15, 2002Publication date: October 3, 2002Inventors: John W. Frost, Karen M. Frost
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Patent number: 6420613Abstract: 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: GrantFiled: December 11, 2000Date of Patent: July 16, 2002Assignee: Tokuyama CorporationInventors: Fumiaki Iwasaki, Yoshihiro Matsumura, Osamu Onomura, Kenji Tanaka
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Patent number: 6417409Abstract: 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: GrantFiled: February 11, 2000Date of Patent: July 9, 2002Assignee: Degussa-Huls AGInventors: Steffen Krill, Klaus Huthmacher
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Publication number: 20020004619Abstract: 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: ApplicationFiled: April 4, 2001Publication date: January 10, 2002Inventors: Steffen Krill, Klaus Huthmacher
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Patent number: 6329535Abstract: 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: GrantFiled: October 20, 2000Date of Patent: December 11, 2001Assignee: Degussa Dental GmbH & Co. KGInventors: Horst Weigel, Steffen Krill, Hans Joachim Hasselbach, Klaus Huthmacher
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Patent number: 6211418Abstract: 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: GrantFiled: July 28, 1998Date of Patent: April 3, 2001Assignee: Nippon Petrochemicals Company LimitedInventors: Kazuharu Suyama, Noboru Kiyota, Tomohiro Konishi, Yasuo Matsumura
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Patent number: 6191323Abstract: 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: GrantFiled: April 25, 2000Date of Patent: February 20, 2001Assignee: UOP LLCInventors: Laszlo T. Nemeth, Avelino Corma Canos, Susana Valencia Valencia, Jaime G. Moscoso, Marcelo Eduardo Domine
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Patent number: 6063968Abstract: 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: GrantFiled: May 14, 1997Date of Patent: May 16, 2000Assignee: Degussa AktiengesellschaftInventors: Frank Hubner, Steffen Krill, Bernd Drapal, Hermann Schmitt, Klaus Huthmacher, Herbert Tanner
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Patent number: 6013844Abstract: 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: GrantFiled: July 15, 1998Date of Patent: January 11, 2000Assignee: BASF AktiengesellschaftInventors: Daniel Heineke, Uwe Dingerdissen, Joachim Wulff-Doring, Michael Hesse
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Patent number: 5817890Abstract: 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: GrantFiled: March 9, 1995Date of Patent: October 6, 1998Assignee: Rhone-Poulenc ChimieInventors: Lucette Duhamel, Pierre Duhamel, Bertrand Leblond, Jean-Marie Poirier
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Patent number: 5583268Abstract: 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: GrantFiled: December 15, 1995Date of Patent: December 10, 1996Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Dennis A. Hucul, Tracy L. Young, Kenneth A. Burdett
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Patent number: 5563300Abstract: 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: GrantFiled: December 7, 1995Date of Patent: October 8, 1996Assignee: Hoechst Celanese CorporationInventors: James R. Sounik, Graham N. Mott, Charles B. Hilton, Mohammad Aslam
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Patent number: 5545388Abstract: 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: GrantFiled: March 29, 1995Date of Patent: August 13, 1996Inventors: Charles J. Rogers, Alfred Kornel
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Patent number: 5478548Abstract: 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: GrantFiled: February 4, 1994Date of Patent: December 26, 1995Inventors: Charles J. Rogers, Alfred Kornel
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Patent number: 5435985Abstract: 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: GrantFiled: February 8, 1994Date of Patent: July 25, 1995Assignee: Kemira OyInventors: Arto Pukkinen, Lauri Heikkinen, Rauni Ruuska
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Patent number: 5399785Abstract: 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: GrantFiled: August 4, 1993Date of Patent: March 21, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Yasutaka Miura, Yasuhiro Kinoshita, Yoshikazu Yamamoto, Kunio Takahashi, Kiyotaka Koyama, Kaoru Takatori
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Patent number: 5319148Abstract: 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: GrantFiled: March 2, 1993Date of Patent: June 7, 1994Assignee: BASF AktiengesellschaftInventors: Michael Karcher, Horst Zimmermann, Jochem Henkelmann
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Patent number: 5276198Abstract: 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: GrantFiled: August 21, 1992Date of Patent: January 4, 1994Assignees: Sumitomo Chemical Company, Limited, Sumika Fine Chemicals Co., Ltd.Inventors: Toshio Nakamatsu, Yasuhiro Nishida, Norio Kometani
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Patent number: 5245084Abstract: 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: GrantFiled: October 17, 1991Date of Patent: September 14, 1993Assignee: Luperox GmbHInventors: Jurgen Groepper, Harald Hofmann
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Patent number: 5233095Abstract: 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: GrantFiled: July 16, 1991Date of Patent: August 3, 1993Assignee: Catalytica, Inc.Inventors: Jere D. Fellmann, Robert J. Saxton, Paul Tung
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Patent number: 4886891Abstract: 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: GrantFiled: December 18, 1987Date of Patent: December 12, 1989Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
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Patent number: 4861921Abstract: 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: GrantFiled: March 3, 1987Date of Patent: August 29, 1989Assignee: Catalytica AssociatesInventors: Jere D. Fellmann, Robert J. Saxton, Paul Tung
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Patent number: 4847429Abstract: 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: GrantFiled: August 3, 1987Date of Patent: July 11, 1989Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, Bruce L. Gustafson, Dale E. Van Sickle, Joseph S. Bowers, Jr.
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Patent number: 4835278Abstract: 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: GrantFiled: January 28, 1987Date of Patent: May 30, 1989Assignee: Glaxo Group LimitedInventors: Roger Barrett, Clive A. Meerholz, Brian D. Judkins
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Patent number: 4798911Abstract: 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: GrantFiled: July 20, 1987Date of Patent: January 17, 1989Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, Bruce L. Gustafson, Paul S. Wehner
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Patent number: 4769500Abstract: 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: GrantFiled: September 24, 1987Date of Patent: September 6, 1988Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomoyuki Yui, Akira Ito
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Patent number: 4600799Abstract: 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: GrantFiled: February 7, 1985Date of Patent: July 15, 1986Assignee: BASF AktiengesellschaftInventors: Franz J. Broecker, Peter Tavs, Harald Laas, Wolf-Karlo Aders
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Patent number: 4538009Abstract: 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: GrantFiled: April 12, 1984Date of Patent: August 27, 1985Assignee: BASF AktiengesellschaftInventors: Norbert Goetz, Harald Laas, Peter Tavs, Leopold Hupfer, Karl Baer
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Patent number: 4536347Abstract: 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: GrantFiled: March 19, 1984Date of Patent: August 20, 1985Assignee: BASF AktiengesellschaftInventors: Michael Horner, Matthias Irgang
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Patent number: 4503249Abstract: Iron (II) hexacyanocobaltate and ruthenium (III) hexacyanocobaltate have been found to be useful in the catalytic hydrogenation of organic materials.Type: GrantFiled: September 21, 1982Date of Patent: March 5, 1985Assignee: Phillips Petroleum CompanyInventors: Gerhard P. Nowack, Marvin M. Johnson, Donald C. Tabler
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Patent number: 4482756Abstract: 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: GrantFiled: July 5, 1983Date of Patent: November 13, 1984Assignee: Sun Tech, Inc.Inventors: Chao-Yang Hsu, James E. Lyons
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Patent number: 4453025Abstract: 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: GrantFiled: November 23, 1982Date of Patent: June 5, 1984Assignee: Shell Oil CompanyInventors: Antonius J. C. Van Seters, Freddy Wattimena