Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/830)
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Patent number: 11207276Abstract: A pharmaceutical dosage form includes an effective amount of L-menthol for treating a gastrointestinal disorder. The L-menthol is within a plurality of particulates having a core including crystalline L-menthol dissolved in a terpene-based essential oil. A proteinaceous coating of a continuous film of proteinaceous material is over the core.Type: GrantFiled: June 6, 2017Date of Patent: December 28, 2021Assignee: Société des Produits Nestlé S.A.Inventors: Syed M. Shah, Fred Hassan, Daniel Hassan, Sarah Hassan
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Hydrogenation catalyst and process for production thereof by the use of uncalcined starting material
Patent number: 10035137Abstract: The invention relates to a process for preparing a shaped Cu—Al catalyst body for the hydrogenation of organic compounds containing a carbonyl function. More particularly, the shaped catalyst body is suitable for the hydrogenation of aldehydes, ketones and of carboxylic acids or esters thereof, specifically of fatty acids or esters thereof, such as fatty acid methyl esters, to the corresponding alcohols such as butanediol. The present invention further relates to Cu—Al catalysts obtainable by the preparation process.Type: GrantFiled: September 25, 2013Date of Patent: July 31, 2018Assignee: CLARIANT INTERNATIONAL LTD.Inventors: Martin Paulus, Frank Grossmann, Karl-Heinz Stadler -
Patent number: 9790157Abstract: The present invention is directed towards a catalyst which is obtainable by contacting in situ a ruthenium precursor and a phenol derivative. Furthermore, the present invention is directed towards the use of said catalyst in transfer hydrogenation reactions. In particular, the present invention is directed to a method for preparing menthone starting from isopulegol.Type: GrantFiled: March 4, 2015Date of Patent: October 17, 2017Assignee: BASF SE (REITSTÖTTER, KINZEBACH & PARTNER)Inventors: Carolin Limburg, Rocco Paciello
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Publication number: 20140066665Abstract: The invention relates to a process for the preparation of 2-isopropyl-5-methylcyclohexanol (D,L-menthol) via the hydrogenation of thymol to menthone and subsequent further hydrogenation to give D,L-menthol.Type: ApplicationFiled: August 29, 2013Publication date: March 6, 2014Applicant: LANXESS DEUTSCHLAND GMBHInventors: Martin MECHELHOFF, Claus DREISBACH, Joerg-Dietrich JENTSCH, Lutz HEUER, Peter WASSERSCHEID, Anne RITTSTEIGER
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Patent number: 8642813Abstract: The present invention provides methods, reactor systems, and catalysts for converting in a continuous process biomass to less complex oxygenated compounds for use in downstream processes to produce biofuels and chemicals. The invention includes methods of converting the components of biomass, such as hemicellulose, cellulose and lignin, to water-soluble materials, including lignocellulosic derivatives, cellulosic derivatives, hemicellulosic derivatives, carbohydrates, starches, polysaccharides, disaccharides, monosaccharides, sugars, sugar alcohols, alditols, polyols, diols, alcohols, ketones, cyclic ethers, esters, carboxylic acids, aldehydes, and mixtures thereof, using hydrogen and a heterogeneous liquefaction catalyst.Type: GrantFiled: December 29, 2011Date of Patent: February 4, 2014Assignee: Virent, Inc.Inventors: Ming Qiao, Randy D. Cortright, John Kania, Elizabeth Woods
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Publication number: 20130253228Abstract: An object of the present invention is to provide a method for manufacturing an optically active menthol having fewer steps, which generates less environmentally polluting waste because a catalytic reaction is involved in all of the steps, and is capable of saving a production cost. The present invention relates to a method for manufacturing an optically active menthol, including the following steps: A-1) asymmetrically hydrogenating at least one of geranial and neral to thereby obtain an optically active citronellal, B-1) conducting a ring-closure reaction of the optically active citronellal in the presence of an acid catalyst to thereby obtain an optically active isopulegol, and C-1) hydrogenating the optically active isopulegol to thereby obtain an optically active menthol.Type: ApplicationFiled: December 1, 2011Publication date: September 26, 2013Inventors: Toshiro Tsuda, Noriaki Senba, Takahiro Uratani
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Publication number: 20130046118Abstract: The present invention relates to a particularly economic overall method for producing menthol, specifically for producing optically active, essentially enantiomerically and diastereomerically pure L-menthol and racemic menthol, starting from the starting material citral which is available inexpensively on an industrial scale. The method comprises the following steps a.1) catalytic hydrogenation of neral and/or geranial to give citronellal, b.1) cyclization of citronellal to isopulegol in the presence of an acidic catalyst, c.1) purification of isopulegol by crystallization and d.1) catalytic hydrogenation of isopulegol to give menthol.Type: ApplicationFiled: October 23, 2012Publication date: February 21, 2013Applicant: BASF SEInventors: Gunnar Heydrich, Gabriele Gralla, Matthias Rauls, Joachim Schmidt-Leithoff, Klaus Ebel, Wolfgang Krause, Steffen Oehlenschläger, Christoph Jäkel, Marko Friedrich, Eike Johannes Bergner, Nawid Kashani-Shirazi, Rocco Paciello
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Patent number: 8318985Abstract: The present invention relates to a particularly economic overall method for producing menthol, specifically for producing optically active, essentially enantiomerically and diastereomerically pure L-menthol and racemic menthol, starting from the starting material citral which is available inexpensively on an industrial scale. The method comprises the following steps a) catalytic hydrogenation of neral and/or geranial to give citronellal, b) cyclization of citronellal to isopulegol in the presence of an acidic catalyst, c) purification of isopulegol by crystallization and d) catalytic hydrogenation of isopulegol to give menthol.Type: GrantFiled: November 13, 2008Date of Patent: November 27, 2012Assignee: BASF SEInventors: Gunnar Heydrich, Gabriele Gralla, Matthias Rauls, Joachim Schmidt-Leithoff, Klaus Ebel, Wolfgang Krause, Steffen Oehlenschläger, Christoph Jäkal, Marko Friedrich, Eike Johannes Bergner, Nawid Kashani-Shirazi, Rocco Paciello
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Patent number: 8304583Abstract: A process of hydrogenating an aliphatic dialdehyde, preferably, a C6-C16 alicyclic dicarboxaldehyde, to form an aliphatic diol, preferably, a C6-C16 alicyclic diol, most preferably, cis/trans-(1,3)(1,4)-cyclohexanedimethanol. The process involves contacting one or more aliphatic dialdehydes in a liquid phase with hydrogen in the presence of a hydrogenation catalyst in a hydrogenation zone and in the presence of water in an amount equal to or greater than 10 weight percent, based on the weight of the total liquid feed to the hydrogenation. The alicyclic dicarboxaldehyde is preferably prepared via hydroformylation of an olefin with subsequent extraction of the alicyclic dicarboxaldehyde product from the hydroformylation product fluid.Type: GrantFiled: August 21, 2008Date of Patent: November 6, 2012Inventors: Glenn A. Miller, Jeffrey S. Sawrey, Christopher W. Derstine
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Patent number: 8134034Abstract: The present invention relates to a method of working up an aluminium-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where Ar1, Ar2, Ar3, Ar4 are chosen from C6-C15-aryl or C2-C15-hetero; R1, R2, R3, R4 are chosen from H, C1-C6-alkyl, C1-C6-perfluoroalkyl, C1-C6-alkoxy, C7-C12-aralkyl, halogen, SiR5bR6bR7b, C6-C10-aryl, NR8bR9b, SR10b, NO2; and where R1 or R2 and/or R3 or R4, together with A, can form an aromatic or nonaromatic cycle; etc.; in which a) the aluminum-containing reaction product is subjected to distillative separation, b) the isopulegol-depleted bottom product is brought into close contact with an aqueous base and c) the ligand of the formula (I) is separated off from the organic phase, preferably by crystallization. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.Type: GrantFiled: August 31, 2007Date of Patent: March 13, 2012Assignee: BASF SEInventors: Gunnar Heydrich, Gabriele Gralla, Klaus Ebel
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Patent number: 8067217Abstract: The present invention has its object to provide a method for stably preserving a capsule containing reduced coenzyme Q10, which is useful as foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, animal drugs, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. The present invention relates to a method for preserving reduced coenzyme Q10 which comprises producing or obtaining a capsule containing reduced coenzyme Q10, and controlling environment surrounding the capsule to a relative humidity of not less than 0% but not more than 60%. According to this method, reduced coenzyme Q10 can be preserved stably, without requiring huge cost and labor, or special equipment.Type: GrantFiled: December 23, 2005Date of Patent: November 29, 2011Assignee: Kaneka CorporationInventors: Takahiro Ueda, Tadao Ono, Shiro Kitamura, Yasuyoshi Ueda
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Patent number: 8013193Abstract: Disclosed is a method for producing an alcohol from a lactone or a carboxylic acid ester, which enables to produce an alcohol from a lactone or a carboxylic acid ester under relatively mild conditions with high yield and high catalytic efficiency. This method also enables to produce an optically active alcohol from an optically active lactone or an optically active carboxylic acid ester. Specifically disclosed is a method for producing an alcohol by hydrogen reducing a lactone or a carboxylic acid ester in the presence of a catalyst containing ruthenium and a phosphine compound represented by the following general formula (1): wherein R1 represents a spacer; R2, R3, R4, R5, R6 and R7 independently represent a hydrogen atom, an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group; and R8, R9, R10, R11, R12 and R13 independently represent an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group.Type: GrantFiled: April 2, 2008Date of Patent: September 6, 2011Assignees: Kaneka Corporation, Takasago International CorporationInventors: Hirofumi Maeda, Kenji Inoue, Takaji Matsumoto, Izuru Nagasaki, Ryoji Noyori, Susumu Saito
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Patent number: 8003829Abstract: The present invention relates to a method of working up an aluminum-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where R1, R2, R3 are chosen from hydrogen, halogen, nitro, C1-C8-alkyl, C1-C8-alkoxy, di(C1-C4-alkyl)amino and aryl; R4, R5 are chosen from halogen, nitro, C1-C8-alkyl, C1-C8-alkoxy, di(C1-C4-alkyl)amino, aryl or heteroaryl; in which a) the reaction product is subjected to distillative separation to obtain an isopulegol-enriched top product and an isopulegol-depleted bottom product and b) the ligand of the formula (I) is separated off from the bottom product. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.Type: GrantFiled: August 31, 2007Date of Patent: August 23, 2011Assignee: BASF SEInventors: Gunnar Heydrich, Gabriele Gralla, Klaus Ebel, Marko Friedrich
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Publication number: 20110201819Abstract: Disclosed is a practical method for efficiently producing an alcohol compound by hydrogenating an aldehyde by using a homogeneous copper catalyst which is an easily-available low-cost metal species. Specifically disclosed is a method for producing an alcohol compound, which is characterized in that a hydrogenation reaction of an aldehyde compound is performed in the presence of a homogeneous copper catalyst and a diphosphine compound.Type: ApplicationFiled: December 11, 2008Publication date: August 18, 2011Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventor: Hideo Shimizu
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Patent number: 7960593Abstract: The present invention relates to a process for preparing racemic or optically active menthol by catalytically hydrogenating racemic or optically active isopulegol in the presence of hydrogen and catalysts which comprise nickel-, copper-, zirconium- and molybdenum-containing compounds. The present invention relates specifically to a corresponding process far continuously catalytically hydrogenating L-isopulegol to L-menthol.Type: GrantFiled: July 16, 2008Date of Patent: June 14, 2011Assignee: BASF SEInventors: Gabriele Gralla, Gunnar Heydrich, Eike Johannes Bergner, Klaus Ebel
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Patent number: 7868211Abstract: The present invention relates to a process for preparing enriched isopulegol by crystallization from a melt comprising isopulegol. The invention relates specifically to a process for preparing enantiomerically enriched n-isopulegol proceeding from optically active isopulegol having a relatively low enantiomeric excess by crystallization from the melt. The invention further relates to a process for preparing menthol proceeding from enantiomerically and/or diastereomerically enriched n-isopulegol prepared by crystallization from the melt.Type: GrantFiled: August 15, 2006Date of Patent: January 11, 2011Assignee: BASF SEInventors: Matthias Rauls, Christoph Jaekel, Nawid Kashani-Shirazi, Klaus Ebel
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Publication number: 20100324338Abstract: This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an ?,?-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound.Type: ApplicationFiled: June 2, 2010Publication date: December 23, 2010Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Hironori MAEDA, Yoji HORI
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Publication number: 20100249467Abstract: The present invention relates to a particularly economic overall method for producing menthol, specifically for producing optically active, essentially enantiomerically and diastereomerically pure L-menthol and racemic menthol, starting from the starting material citral which is available inexpensively on an industrial scale. The method comprises the following steps a.1) catalytic hydrogenation of neral and/or geranial to give citronellal, b.1) cyclization of citronellal to isopulegol in the presence of an acidic catalyst, c.1) purification of isopulegol by crystallization and d.1) catalytic hydrogenation of isopulegol to give menthol.Type: ApplicationFiled: November 13, 2008Publication date: September 30, 2010Applicant: BASF SEInventors: Gunnar Heydrich, Gabriele Gralla, Matthias Rauls, Joachim Schmidt-Leithoff, Klaus Ebel, Wolfgang Krause, Steffen Oehlenschläger, Christoph Jäkel, Marko Friedrich, Eike Johannes Bergner, Nawid Kashani-Shirazi, Rocco Paciello
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Publication number: 20100191021Abstract: The present invention relates to a process for preparing racemic or optically active menthol by catalytically hydrogenating racemic or optically active isopulegol in the presence of hydrogen and catalysts which comprise nickel-, copper-, zirconium- and molybdenum-containing compounds. The present invention relates specifically to a corresponding process far continuously catalytically hydrogenating L-isopulegol to L-menthol.Type: ApplicationFiled: July 16, 2008Publication date: July 29, 2010Applicant: BASF SEInventors: Gabriele Gralla, Gunnar Heydrich, Eike Johannes Bergner, Klaus Ebel
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Publication number: 20100152494Abstract: The present invention relates to a process for preparing optically active carbonyl compounds by asymmetrically hydrogenating ?,?-unsaturated carbonyl compounds in the presence of optically active transition metal catalysts which are soluble in the reaction mixture and have at least one carbon monoxide ligand, the optically active catalyst which has at least one carbon monoxide ligand and is to be used in each case being prepared by pretreating a catalyst precursor with a gas mixture comprising carbon monoxide and hydrogen and the asymmetric hydrogenation being performed in the presence of carbon monoxide supplied additionally to the reaction mixture.Type: ApplicationFiled: April 17, 2008Publication date: June 17, 2010Applicant: BASF SEInventors: Joachim Schmidt-Leithoff, Christoph Jäkel, Rocco Paciello
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Patent number: 7709688Abstract: Processes comprising: (a) enantioselectively hydrogenating a staffing material comprising a component selected from geraniol, nerol and mixtures thereof to form optically active citronellol; (b) converting the optically active citronellol to optically active citronellal; (c) cyclizing the optically active citronellal to form a mixture comprising optically active isopulegol; and (d) subjecting the mixture to further processing comprising: (i) separating the optically active isopulegol from the mixture and hydrogenating the separated optically active isopulegol to form optically active menthol; or (ii) hydrogenating the optically active isopulegol in the mixture to form optically active menthol and separating the optically active menthol from the mixture.Type: GrantFiled: November 24, 2005Date of Patent: May 4, 2010Assignee: BASF SEInventors: Eike Johannes Bergner, Klaus Ebel, Thorsten Johann, Oliver Löber
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Publication number: 20100016642Abstract: The present invention relates to a method of working up an aluminum-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where R1, R2, R3 are chosen from hydrogen, halogen, nitro, C1-C8-alkyl, C1-C8-alkoxy, di(C1-C4-alkyl)amino and aryl; R4, R5 are chosen from halogen, nitro, C1-C8-alkyl, C1-C8-alkoxy, di(C1-C4-alkyl)amino, aryl or heteroaryl; in which a) the reaction product is subjected to distillative separation to obtain an isopulegol-enriched top product and an isopulegol-depleted bottom product and b) the ligand of the formula (I) is separated off from the bottom product. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.Type: ApplicationFiled: August 31, 2007Publication date: January 21, 2010Applicant: BASF SEInventors: Gunnar Heydrich, Gabriele Gralla, Klaus Ebel, Marko Friedrich
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Publication number: 20100010253Abstract: The present invention relates to a method of working up an aluminium-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where Ar1, Ar2, Ar3, Ar4 are chosen from C6-C15-aryl or C2-C15-hetero; R1, R2, R3, R4 are chosen from H, C1-C6-alkyl, C1-C6-perfluoroalkyl, C1-C6-alkoxy, C7-C12-aralkyl, halogen, SiR5bR6bR7b, C6-C10-aryl, NR8bR9b, SR10b, NO2; and where R1 or R2 and/or R3 or R4, together with A, can form an aromatic or nonaromatic cycle; etc.; in which a) the aluminum-containing reaction product is subjected to distillative separation, b) the isopulegol-depleted bottom product is brought into close contact with an aqueous base and c) the ligand of the formula (I) is separated off from the organic phase, preferably by crystallization. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.Type: ApplicationFiled: August 31, 2007Publication date: January 14, 2010Applicant: BASF SEInventors: Gunnar Heydrich, Gabriele Gralla, Klaus Ebel
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Publication number: 20090253919Abstract: Chiral thioureas are effective catalysts for the borane reduction of prochiral ketones to optically active alcohols. A prochiral ketone may be reduced to an optically active alcohol in the presence of a substantially sub-stoichiometric amount of chiral thiourea. The asymmetric thiourea compound of the present invention may be produced according to a production method described herein.Type: ApplicationFiled: April 3, 2008Publication date: October 8, 2009Applicant: Board of RegentsInventors: Derun Li, John R. Falck
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Patent number: 7569735Abstract: A method for producing alcohols which comprises reducing esters or lactones with hydrogen gas in the presence of a catalyst comprising (i) a ruthenium compound, (ii) a monodentate monophosphine or a bidentate bisphosphine, and (iii) an amine. Examples of the catalyst include a ruthenium (Ru) complex represented by the formula:RuX1X2(LP)m(LN)n [X1 and X2 each represent an anionic ligand, LP represents a phosphine ligand, m is 1 when LP is bidentate, while m is 2 when LP is monodentate, LN represents an amine ligand, and n is 1 when LN is bidentate, while n is 2 when LN is monodentate.] and a catalyst comprising an amine and a ruthenium (Ru) complex of the formula: RuX1X2(LP1)r [LP1 represents a monophosphine ligand and r is 3 or 4.].Type: GrantFiled: March 14, 2008Date of Patent: August 4, 2009Assignee: Takasago InternationalInventors: Yasunori Ino, Akifumi Yoshida, Wataru Kuriyama
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Patent number: 7550633Abstract: The present invention relates to a process for the preparation of isopulegol of formula (I): comprising the cyclization of citronellal of formula (II): in the presence of a tris(aryloxy)aluminum catalyst, wherein the cyclization is carried out in the presence of I. at least one acid and/or II. at least one compound selected from the group comprising carboxylic anhydrides, aldehydes, ketones and vinyl ethers.Type: GrantFiled: December 17, 2005Date of Patent: June 23, 2009Assignee: BASF SEInventors: Marko Friedrich, Klaus Ebel, Norbert Götz
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Publication number: 20090036699Abstract: Processes for the preparation of a compound of the formula (B) having the following steps: provision of a compound of the formula (A), intramolecular reaction of the compound of the formula (A) in the presence of an aluminium siloxide of the formula (I) wherein in formula (I) the radicals Ra?, Ra?, Ra??, Rb?, Rb?, Rb??, Rc?, Rc?, Rc?? independently of one another denote hydrogen or an organic radical, are described.Type: ApplicationFiled: September 4, 2006Publication date: February 5, 2009Applicant: SYMRISE GmbH & Co. KGInventor: Markus Nobis
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Publication number: 20080300430Abstract: The present disclosure relates to a process for the reduction of compounds comprising one or more carbon-oxygen (C?O) double bonds, to provide the corresponding alcohol, comprising contacting the compound with hydrogen gas at a pressure greater than 3 atm and a catalyst comprising an iridium aminodiphosphine complex.Type: ApplicationFiled: May 30, 2008Publication date: December 4, 2008Inventors: Kamaluddin Abdur-Rashid, Rongwei Guo, Xuanhua Chen, Wenli Jia
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Publication number: 20080269528Abstract: The present invention relates to a process for preparing optically active carbonyl compounds by asymmetrically hydrogenating ?,?-unsaturated carbonyl compounds in the presence of optically active transition metal catalysts which are soluble in the reaction mixture and have at least one carbon monoxide ligand. The present invention especially relates to a process for preparing optically active aldehydes or ketones, in particular citronellal, by asymmetrically hydrogenating the corresponding optically active ?,?-unsaturated aldehydes or ketones.Type: ApplicationFiled: October 8, 2005Publication date: October 30, 2008Inventors: Christoph Jakel, Rocco Paciello
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Publication number: 20080214877Abstract: The present invention relates to a process for preparing enriched isopulegol by crystallization from a melt comprising isopulegol. The invention relates specifically to a process for preparing enantiomerically enriched n-isopulegol proceeding from optically active isopulegol having a relatively low enantiomeric excess by crystallization from the melt. The invention further relates to a process for preparing menthol proceeding from enantiomerically and/or diastereomerically enriched n-isopulegol prepared by crystallization from the melt.Type: ApplicationFiled: August 15, 2006Publication date: September 4, 2008Applicant: BASF SEInventors: Matthias Rauls, Christoph Jakel, Nawid Kashani-Shirazi, Klaus Ebel
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Publication number: 20080207957Abstract: The present invention relates to a process for the preparation of isopulegol of formula (I): comprising the cyclization of citronellal of formula (II): in the presence of a tris(aryloxy)aluminum catalyst, wherein the cyclization is carried out in the presence of I. at least one acid and/or II. at least one compound selected from the group comprising carboxylic anhydrides, aldehydes, ketones and vinyl ethers.Type: ApplicationFiled: December 17, 2005Publication date: August 28, 2008Applicant: BASF AktiengesellschaftInventors: Marko Friedrich, Klaus Ebel, Norbert Gotz
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Publication number: 20080139852Abstract: Processes comprising: (a) enantioselectively hydrogenating a starting material comprising a component selected from geraniol, nerol and mixtures thereof to form optically active citronellol; (b) converting the optically active citronellol to optically active citronellal; (c) cyclizing the optically active citronellal to form a mixture comprising optically active isopulegol; and (d) subjecting the mixture to further processing comprising: (i) separating the optically active isopulegol from the mixture and hydrogenating the separated optically active isopulegol to form optically active menthol; or (ii) hydrogenating the optically active isopulegol in the mixture to form optically active menthol and separating the optically active menthol from the mixture.Type: ApplicationFiled: November 24, 2005Publication date: June 12, 2008Applicant: BASF AktiengesellschaftInventors: Eike Johannes Bergner, Klaus Ebel, Thorsten Johann, Oliver Lober
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Patent number: 7301057Abstract: The present invention relates to a process for preparing 3(4),8(9)-dihydroxymethyltricyclo[5.2.102.6]decane by hydrogenating the hyd roformylation products of d icyclopentad lene. The process comprises carrying out the hydrogenation in the presence of water, optionally after addition of water.Type: GrantFiled: May 25, 2005Date of Patent: November 27, 2007Assignee: Oxea Deutschland GmbHInventors: Wolfgang Dukat, Edgar Storm, Klaus Schmid
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Patent number: 7250537Abstract: The present invention provides a novel method of hydrogenating a phenol for hydrogenating a phenol industrially advantageously. The present invention relates, in the case of phenol hydrogenation in which carbon dioxide is made to participate in the reaction, to a method of hydrogenating a phenol characterized by using a supported rhodium and/or ruthenium catalyst, whereby the phenol is hydrogenated efficiently at a lower reaction temperature than with prior art; such a method characterized in that carbon dioxide having a temperature of 20 to 250° C. and a pressure of 0.1 to 50 MPa is used as the carbon dioxide; and such a method characterized in that hydrogen under conditions of a temperature of 20 to 250° C. and a pressure of 0.1 to 50 MPa is used. An environmentally friendly phenol hydrogenation process that uses no harmful organic solvents can be realized.Type: GrantFiled: March 30, 2004Date of Patent: July 31, 2007Assignee: National Institute of Advanced Industrial Science and TechnologyInventors: Masayuki Shirai, Chandrashekhar Vasant Rode, Uday Dattopant Joshi, Kazuo Torii, Takafumi Sato
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Patent number: 7145041Abstract: The invention relates to a method for catalytically oxidizing unsaturated hydrocarbons to form oxidation products, and to the production of saturated alcohols, ketones, aldehydes or carboxylic acids by subsequently hydrogenating the oxidation product. A compound of formula (I) is used as a catalyst during oxidizing in which: R1, R2=H, an aliphatic or aromatic alkoxy radical, carboxyl radical, alkoxycarbonyl radical or hydrocarbon radical, each having 1 to 20 carbon atoms, SO3H, NH2, OH, F, Cl, Br, I and/or NO2, whereby R1 and R2 signify identical or different radicals or R1 and R2 can be coupled to one another via a covalent bond, with Q1, Q2=the same or different, C, CH, N; X, Z=C, S or CH2; Y=O or OH; k=0, 1 or 2; 1=0, 1 or 2; m=1 to 100 in the presence of a radical initiator. Peroxy compounds or azo compounds can be used as radical initiators. Preferred substrates are cyclic aliphatic or aromatic compounds.Type: GrantFiled: June 12, 2002Date of Patent: December 5, 2006Assignee: Degussa AGInventors: Adolf Kuehnle, Carsten Jost, Roger Arthur Sheldon, Sandrine M. M. Chatel, Isabella W. C. E. Arends
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Patent number: 7145044Abstract: The present invention relates to a method of conveniently and efficiently producing reduced coenzyme Q10 having excellent qualities which is useful in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, drinks, feeds, animal drugs, cosmetics, medicines, remedies, preventive drugs, etc. This method is suitable for industrial production thereof. In a method of synthesizing reduced coenzyme Q10 by reducing oxidized coenzyme Q10, followed by crystallization, at least one species selected from among hydrocarbons, fatty acid esters, ethers and nitrites is used as a solvent. Thus, the reduced coenzyme Q10 can be protected from oxidation, and as a result, the formation of the oxidized coenzyme Q10 as a by-product can be minimized, thereby giving reduced coenzyme Q10 having excellent qualities.Type: GrantFiled: July 15, 2002Date of Patent: December 5, 2006Assignee: Kaneka CorporationInventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
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Patent number: 7105709Abstract: The present invention relates to a method of conveniently and efficiently producing high-quality reduced coenzyme Q10 which is useful as an ingredient in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, animal drugs, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. This method is suitable for industrial production thereof. A method of producing a reduced coenzyme Q10 which comprises reducing an oxidized coenzyme Q10 in an aqueous medium with the use of dithionous acid or a salt thereof, said reduction being carried out in the coexistence of a salt and/or under deoxygenated atmosphere, and at pH of 7 or below. Thus, the formation of the oxidized coenzyme Q10 as a by-product due to oxidation can be minimized, thereby giving reduced coenzyme Q10 having excellent qualities in a high yield.Type: GrantFiled: July 15, 2002Date of Patent: September 12, 2006Assignee: Kaneka CorporationInventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
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Patent number: 7084312Abstract: A process for the hydrogenation of an organic compound containing at least one carbonyl group comprises bringing the organic compound in the presence of hydrogen into contact with a shaped body which can be produced by a process in which (i) an oxidic material comprising copper oxide, zinc oxide and aluminum oxide is made available, (ii) pulverulent metallic copper or pulverulent cement or a mixture thereof is added to the oxidic material, and (iii) the mixture resulting from (ii) is shaped to form a shaped body.Type: GrantFiled: August 22, 2000Date of Patent: August 1, 2006Assignee: BASF AktiengesellschaftInventors: Sylvia Huber, Michael Jolyon Sprague, Boris Breitscheidel, Joachim Wulff-Döring, Michael Hesse, Rolf Pinkos, Shelue Liang, Otto Kumberger, Marc Walter
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Patent number: 7015014Abstract: The present invention relates to a crystalline carotenoid compound, such as ?-carotene, with a purity of at least 95% and with substantially no solvent enclosed in the crystal lattice. The present invention further describes a process to prepare such a highly pure crystalline carotenoid compound from microbial biomass, without the use of a solvent extraction and/or an anti-solvent crystallization process.Type: GrantFiled: January 29, 2001Date of Patent: March 21, 2006Assignee: DSM IP Assets B.V.Inventors: Albert Schaap, Mieke Sibeijn, Johannes Hendrik Wolf
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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: 6660890Abstract: A process for the heterogeneous and enantioselective hydrogenation of prochiral organic &agr;-keto compounds with platinum as the catalyst in the presence of a soluble or immobilized chiral aromatic nitrogen base with at least one basic nitrogen atom adjacent to stereogenic carbon atoms, whereby prochiral &agr;-ketoacetals are hydrogenated to optically active &agr;-hydroxyacetals.Type: GrantFiled: December 19, 2001Date of Patent: December 9, 2003Assignee: Solvias AGInventor: Martin Studer
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Patent number: 6576787Abstract: Hydroxymethyl-group-containing alicyclic compounds that are useful for making photosensitive resins and other functional polymers. Processes for producing the hydroxymethyl-group-containing alicyclic compounds. Polymerizable alicyclic compounds. The alicyclic moieties in all of these compounds may be a polycyclic ring such as a perhydroindene ring, a decalin ring, a perhydrofluorene ring, a perhydroanthracene ring, a perhydrophenanthrene ring, a tricyclo[5.2.1.02.6]decane ring, a perhydroacenaphthene ring, or a perhydrophenalene ring.Type: GrantFiled: October 6, 2000Date of Patent: June 10, 2003Assignee: Daicel Chemical Industries, Ltd.Inventors: Tatsuya Nakano, Hiroshi Shimojitosyo
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Patent number: 6429344Abstract: The invention relates to a process for the preparation of d,l-menthol by catalytic hydrogenation of compounds which have the carbon skeleton of menthane containing at least one double bond and are 3-substituted by oxygen and/or of menthone or isomenthone or mixtures of such compounds using hydrogen at temperatures of 100 to 200° C. and at hydrogen partial pressures between 2 and 50 bar and/or by rearrangement of menthol stereoisomers in the presence of hydrogen at temperatures of 0 to 140° C. and at hydrogen partial pressures between 0.1 and 20 bar in the presence of noble-metal-containing catalysts.Type: GrantFiled: November 15, 1999Date of Patent: August 6, 2002Assignee: Bayer AktiengesellschaftInventors: Reinhard Langer, Gerd-Michael Petruck
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Patent number: 6407294Abstract: A process for producing 1,6-hexanediol by hydrogenation of adipic esters and/or 6-hydroxycaproic esters in the gas phase at elevated temperature and elevated pressure in the presence of chromium-free catalysts comprises hydrogenating a) over a catalyst comprising copper, manganese and aluminum as essential constituents or over Raney copper, b) at a temperature of from 150 to 230° C. and a pressure of from 10 to 70 bar, c) at a molar ratio of hydrogen to ester to be hydrogenated within the range from 150:1 to 300:1, and d) at a catalyst space velocity of from 0.01 to 0.3 kg of C6 ester per liter of catalyst per hour.Type: GrantFiled: April 20, 2000Date of Patent: June 18, 2002Assignee: BASF AktiengesellschaftInventors: Boris Breitscheidel, Rolf Pinkos, Frank Stein, Shelue Liang, Rolf Hartmuth Fischer
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Patent number: 6342644Abstract: Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.Type: GrantFiled: May 7, 2001Date of Patent: January 29, 2002Assignee: Takasago International CorporationInventors: Noboru Sayo, Takaji Matsumoto
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Publication number: 20020007094Abstract: Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.Type: ApplicationFiled: May 7, 2001Publication date: January 17, 2002Inventors: Noboru Sayo, Takaji Matsumoto
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Patent number: 6262284Abstract: A process for simultaneously extracting, saponifying, and isolating lutein and zeaxanthin, and a mixture of several rare carotenoids in high purity from plants without the use of harmful organic solvents. Lutein crystals containing 5% zeaxanthin were obtained from the dried petals of Marigold flowers Tagete erecla while zeaxanthin was isolated and purified from the berries of Lycium Chinese Mill (LCM berries). Similarly, this process has been employed to isolate and purify a mixture of lutein, beta-carotene, neoxanthin, violaxanthin, and lutein epoxide from green plants, preferably, kale, collard green, and spinach. These plants, to a lesser extent, also serve as a source of several rare carotenoids such as alpha-cryptoxanthin (Marigolds) and beta-cryptoxanthin (LCM berries). The purified carotenoids isolated by this process are free from impurities and serve as a safe source of nutritional supplement for human consumption as well as providing a suitable and effective color additive for human foods.Type: GrantFiled: April 20, 2000Date of Patent: July 17, 2001Assignee: University of MarylandInventor: Frederick Khachik
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Patent number: 5942645Abstract: A process for hydrogenating aromatic compounds in which at least one hydroxyl group is bonded to an aromatic ring comprises bringing at least one of these compounds into contact with free hydrogen in the presence of a catalyst, wherein the catalyst comprises ruthenium and, if desired, at least one metal of transition groups I, VII and VIII in an amount of from 0.01 to 30% by weight, preferably from 0.2 to 15% by weight, based on the total weight of the catalyst, applied to a support, where the support has a mean pore diameter of at least 0.1 .mu.m, preferably at least 0.5 .mu.m, and a surface area of at most 15 m.sup.2 /g, preferably at most 10 m.sup.2 /g.Type: GrantFiled: February 3, 1997Date of Patent: August 24, 1999Assignee: BASF AktiengesellschaftInventors: Heinz Rutter, Thomas Ruhl, Boris Breitscheidel, Jochem Henkelmann, Thomas Wettling
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Patent number: 5756864Abstract: A process is described for preparing D,L-menthol by catalytic rearrangement of optically active D-menthol in the presence of hydrogen at temperatures of from 200 to 350.degree. C. and under pressures of from 50 to 350 bar over fixed-bed catalysts comprising support-free reduced shaped bodies of pressed powders of nickel, manganese, alkaline earth metal (hydr)oxides and optionally (hydr)oxides of elements of transition groups V and/or VI of the Periodic Table.Type: GrantFiled: May 10, 1996Date of Patent: May 26, 1998Assignee: Bayer AktiengesellschaftInventors: Gerhard Darsow, Gerd-Michael Petruck
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Patent number: 5750803Abstract: A continuous process is described for the preparation of D,L-menthol by catalytic hydrogenation of compounds which have the carbon skeleton of p-menthane containing at least one double bond and are 3-substituted by oxygen using hydrogen and/or by rearrangement of stereoisomers of menthol in the presence of hydrogen at temperatures of 150.degree. to 230.degree. C. and at pressures of 25 to 350 bar on fixed-bed catalysts made of support-free reduced shaped bodies made of pressed powders of cobalt (hydr)oxide, manganese (hydr)oxide, alkaline earth metal (hydr)oxides and, optionally, (hydr)oxides of elements of subgroup V and/or VI of the Periodic Table of the Elements.Type: GrantFiled: May 10, 1996Date of Patent: May 12, 1998Assignee: Bayer AktiengesellschaftInventors: Gerhard Darsow, Gerd-Michael Petruck