Preparing Alicyclic Acid Esters By Carbonylation Patents (Class 560/114)
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Patent number: 12091383Abstract: The invention relates to a method for producing lipids comprising structural units based on glycerides of 3-hydroxybutyric and/or 3-alkoxybutyric acids as well as the products thus obtained and their use.Type: GrantFiled: January 23, 2019Date of Patent: September 17, 2024Assignee: KETOLIPIX THERAPEUTICS GMBHInventors: Dirk Lochmann, Sebastian Reyer, Michael Stehr
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Patent number: 12077494Abstract: Process for the alkoxycarbonylation of trivinylcyclohexane.Type: GrantFiled: March 7, 2023Date of Patent: September 3, 2024Assignee: EVONIK OXENO GMBH & CO. KGInventors: Kaiwu Dong, Robert Franke, Ralf Jackstell, Matthias Beller
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Patent number: 11629115Abstract: Process for the alkoxycarbonylation of trivinylcyclohexane.Type: GrantFiled: December 15, 2020Date of Patent: April 18, 2023Assignee: EVONIK OPERATIONS GMBHInventors: Kaiwu Dong, Robert Franke, Ralf Jackstell, Matthias Beller
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Patent number: 11623912Abstract: The invention relates to triesters of cyclohexanetripropionic acid, preparation thereof and use thereof as plasticizers for polymers wherein examples of the triester of cyclohexanetripropionic acid include tri(nbutyl) cyclohexane-1,2,4-tripropionate, tri(methylpropyl) cyclohexane-1,2,4-tripropionate, tri(npentyl) cyclohexane-1,2,4-tripropionate, tri(isopentyl) cyclohexane-1,2,4-tripropionate, tri(2-methylbutyl) cyclohexane-1,2,4-tripropionate, tri(3-methylbutyl) cyclohexane-1,2,4-tripropionate, tri(nhexyl) cyclohexane-1,2,4-tripropionate, tri(isohexyl) cyclohexane-1,2,4-tripropionate, tri(nheptyl) cyclohexane-1,2,4-tripropionate, tri(isoheptyl) cyclohexane-1,2,4-tripropionate, tri(noctyl) cyclohexane-1,2,4-tripropionate, tri(isooctyl) cyclohexane-1,2,4-tripropionate, tri(2-ethylhexyl) cyclohexane-1,2,4-tripropionate, tri(nnonyl) cyclohexane-1,2,4-tripropionate, tri(isononyl) cyclohexane-1,2,4-tripropionate, tri(ndecyl) cyclohexane-1,2,4-tripropionate, tri(isodecyl) cyclohexane-1,2,4-tripropionate, and tri(2-pType: GrantFiled: December 7, 2020Date of Patent: April 11, 2023Assignee: Evonik Operations GmbHInventors: Imke Schulz, Michael Grass, Robert Franke, Johannes Kraft, Matthias Beller, Ralf Jackstell
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Patent number: 10144699Abstract: The present invention is able to provide a bifunctional compound represented by formula (1). (In the formula, R1 represents COOCH3, COOC2H5, COOC3H7, COOC4H9 or CHO; and R2 represents H, CH3 or C2H5.Type: GrantFiled: April 5, 2018Date of Patent: December 4, 2018Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Takashi Motoi, Mitsuharu Kitamura, Manabu Hirakawa
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Patent number: 8895773Abstract: The present invention relates to the manufacture of alkyl p-toluates from an alkyl p-toluic acid ester and a mono-functional, branched, linear or cyclic medium chain length alkyl alcohol, and their use as a plasticizer in polymers. Additionally, the present invention relates to articles and materials comprising such alkyl p-toluates.Type: GrantFiled: May 8, 2009Date of Patent: November 25, 2014Assignee: Invista North America S.a.r.l.Inventor: Carina Araullo McAdams
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Patent number: 8829228Abstract: There are provided a novel carboxylate compound useful as a blending perfume raw material and having a brisk pine-like odor and a method of producing the same and a perfume composition containing such a carboxylate compound. The carboxylate compound of the invention is represented by a general formula (1): wherein R is an alkyl group having two to four carbon atoms.Type: GrantFiled: November 1, 2011Date of Patent: September 9, 2014Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Mitsuharu Kitamura
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Publication number: 20140087990Abstract: The present invention provides a novel carboxylic acid ester compound useful as a fragrance component or a material for a compound fragrance and a method for producing the same, and provides a fragrance composition including the carboxylic acid ester compound. The present invention also provides an acyl fluorides of a 2,4-dimethyl-bicyclo[2.2.2]octane compound and the esters thereof, useful as the raw materials (inclusive of the intermediates of organic synthesis), for example, for the medicines, agricultural chemicals, fragrances, functional resins, optical functional materials and electronic functional materials. The carboxylic acid ester compound of the present invention is a compound represented by the general formula (1). (In the formula, one of R1 and R2 is a methyl group and the other of R1 and R2 is —COOR, and R is an alkyl group having 1 to 4 carbon atoms.Type: ApplicationFiled: March 23, 2012Publication date: March 27, 2014Applicant: Mitsubishi Gas Chemical, Inc.Inventor: Mitsuharu Kitamura
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Publication number: 20130324688Abstract: The preparation of cyclohexadienes from one or more plant oils is disclosed. The cyclohexadiene can be used to form polymers or derivatized to form other monomers that can be used to form polymeric materials.Type: ApplicationFiled: April 9, 2013Publication date: December 5, 2013Inventor: Robert T. MATHERS
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Patent number: 8519177Abstract: A modified dimethylnaphthalene formaldehyde resin obtained by modifying a polyfunctional dimethylnaphthalene formaldehyde resin having a constituent unit represented by the following general formula [1] in a molecule thereof with at least one member selected from the group consisting of a phenol represented by the following general formula [2], a naphthol represented by the following general formula [3] and a naphthol represented by the following general formula [4] provided that at least any of the naphthol represented by the general formula [3] or the naphthol represented by the general formula [4] must be included.Type: GrantFiled: March 19, 2012Date of Patent: August 27, 2013Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Seiji Kita, Masashi Ogiwara, Mitsuharu Kitamura, Dai Oguro, Gou Higashihara
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Publication number: 20130184486Abstract: There are provided a novel carboxylate compound useful as a blending perfume raw material and having a brisk pine-like odor and a method of producing the same and a perfume composition containing such a carboxylate compound. The carboxylate compound of the invention is represented by a general formula (1): wherein R is an alkyl group having two to four carbon atoms.Type: ApplicationFiled: November 1, 2011Publication date: July 18, 2013Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventor: Mitsuharu Kitamura
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Publication number: 20130171385Abstract: Multi-esters of the formula: wherein each R1 is the hydrocarbon residue of a C4 to C13 OXO-alcohol averaging from 0.2 to 5.0 branches per residue, and R2 is hydrogen or an ester group, processes of making the multi-esters, use of the multi-esters as plasticizers, polymer compositions containing such plasticizers, and articles containing such plasticizers.Type: ApplicationFiled: December 21, 2012Publication date: July 4, 2013Applicant: EXXONMOBIL RESEARCH AND ENGINEERING COMPANYInventor: EXXONMOBIL RESEARCH AND ENGINEERING COMPANY
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Patent number: 8071270Abstract: The present invention provides a polyhydric compound represented by the formula (I): wherein R51 to R67 each independently represent a hydrogen atom etc., at least one selected from the group consisting of R1 to R5 is a group represented by the formula (II): wherein Q1 and Q2 each independently represent a fluorine atom etc., U represents a C1-C20 divalent hydrocarbon group etc., and A+ represents an organic counter ion, and the others are hydrogen atoms or groups represented by the formula (III): wherein X1 to X4 each independently represent a hydrogen atom etc., n represents an integer of 0 to 3, W represents any one of the following groups: Z1 represents a C1-C6 alkyl group etc., and ring Y represents a C3-C20 alicyclic hydrocarbon group, and a chemically amplified resist composition containing the same.Type: GrantFiled: February 23, 2009Date of Patent: December 6, 2011Assignee: Sumitomo Chemical Company, LimitedInventors: Ichiki Takemoto, Nobuo Ando
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Patent number: 7939621Abstract: A cyclic carbonate monomer, including: wherein R1, R2, and R3 are independently selected from the group consisting of H, linear or branched, substituted or unsubstituted alkyl; R10 is a connecting group selected from the group consisting of linear or branched, substituted or unsubstituted alkyl, heteroalkyl, cycloalkyl, heterocyclic, aryl and heteroaryl; R4 is an optional bridging group selected from the group consisting of linear or branched, substituted or unsubstituted alkyl, heteroalkyl, cycloalkyl, heterocyclic, aryl and heteroaryl; Z is selected from the group consisting of O, NH, NR, and S; G is a guanidine group; and P is a protecting group. The cylic carbonate monomer can be reacted with an initiator including a drug, drug candidate, probe or other molecule of interest to form an oligomer with the molecule of interest attached to one end of a carbonate backbone and guanidine groups attached to the carbonate backbone.Type: GrantFiled: April 30, 2009Date of Patent: May 10, 2011Assignees: International Business Machines Corporation, Stanford UniversityInventors: Christina Cooley, James Lupton Hedrick, Matthew Kiesewetter, Fredrik Nederberg, Brian Trantow, Robert Waymouth, Paul Wender
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Publication number: 20110105782Abstract: A process is described for the preparation of carbamates of primary and/or secondary polyamines, which process comprises the steps of vaporising a primary and/or secondary polyamine and reacting said vaporised primary and/or secondary polyamine with gaseous carbon dioxide. In particular, the process relates to the production of the carbamates of hexamethylenediamine, 1,4-diaminocyclohexane and 3-aminomethyl-3,5,5-trimethylcyclohexylamine.Type: ApplicationFiled: April 18, 2005Publication date: May 5, 2011Inventor: Maurizio Masi
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Publication number: 20100158804Abstract: Methods and reagents for photo-initiated carbonylation with carbon-isotope labeled carbon monoxide using alkyl/aryl iodides with alcohols or water treated by photosensitizers are provided. The resultant carbon-isotope labeled esters and acids, and pharmaceutical acceptable salts and solvates are useful as radiopharmaceuticals, especially for use in Positron Emission Tomography (PET). Associated kits and method for PET studies are also provided.Type: ApplicationFiled: March 2, 2010Publication date: June 24, 2010Applicant: GE HEALTHCARE LIMITEDInventors: BENGT LANGSTROM, OLEKSIY ITSENKO
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Patent number: 7626052Abstract: Methods and reagents for photo-initiated carbonylation with carbon-isotope labeled carbon monoxide using alkyl/aryl iodides with alcohols pretreated by a base are provided. The resultant carbon-isotope labeled esters are useful as radiopharmaceuticals, especially for use in Positron Emission Tomography (PET). Associated kits for PET studies are also provided.Type: GrantFiled: December 14, 2005Date of Patent: December 1, 2009Assignee: GE Healthcare LimitedInventors: Bengt Langstrom, Oleksiy Itsenko, Tor Kihlberg
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Patent number: 7495122Abstract: A novel compound represented by a formula [1] wherein R1 and R2 respectively represent a light or heavy hydrogen atom, R3 represents a light or heavy hydrogen atom or a methyl group in which tree hydrogen atoms are respectively light or heavy hydrogen atoms, and R4 is a norbornyl group provided that four or more hydrogen atoms in the norbornyl group are heavy hydrogen atoms; and a novel polymer produced by polymerization of a composition comprising the compound are disclosed.Type: GrantFiled: July 23, 2004Date of Patent: February 24, 2009Assignees: Wako Pure Chemical Industries, Fujifilm CorporationInventors: Hiroki Sasaki, Tsuneaki Maesawa, Nobuhiro Ito, Kazushige Muto
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Patent number: 7494763Abstract: The present invention provides a polyhydric phenol compound represented by the formula (I): wherein at least one selected from R1, R2, R3, R4, and R5 is a group represented by the formula (II): wherein X1, X2, X3 and X4 each independently represent a hydrogen atom or a C1-C4 alkyl group, n represents an integer of 0 to 3, Z1 represents a C1-C6 alkyl group or a C3-C12 cycloalkyl group, and ring Y represents an alicyclic hydrocarbon group, and the others are hydrogen atoms, and a chemically amplified resist composition containing the same.Type: GrantFiled: October 22, 2007Date of Patent: February 24, 2009Assignee: Sumitomo Chemical Company, LimitedInventors: Ichiki Takemoto, Nobuo Ando, Junji Shigematsu
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Patent number: 7432390Abstract: In the production of carboxylic acid or carboxylic acid ester, a reaction product containing the carboxylic acid or carboxylic acid ester which has been produced by the reaction of an olefin, carbon monoxide, and water or an alcohol in the presence of HF is heat-treated in the presence of an acid catalyst and an acid adsorbent. By the heat treatment, the contamination of the carboxylic acid or carboxylic acid ester with HF and/or fluorine compounds such as acyl fluorides can be prevented, to enable the stable production of a high quality and high purity carboxylic acid or carboxylic acid ester without causing troubles such as corrosion of apparatus.Type: GrantFiled: March 9, 2006Date of Patent: October 7, 2008Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Mitsuharu Kitamura, Kinji Kato
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Patent number: 7268250Abstract: A highly efficient process is provided for producing an optically active compound having high optical purity by an asymmetric reaction using as a catalyst a transition metal complex having an optically active nitrogen-containing compound as an asymmetric ligand.Type: GrantFiled: December 31, 2003Date of Patent: September 11, 2007Assignee: Kanto Kagaku Kabushiki KaishaInventors: Masahito Watanabe, Kunihiko Murata, Takao Ikariya
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Patent number: 7256305Abstract: A process for producing a ?-hydroxyester by reacting an epoxide, an alcohol and carbon monoxide in the presence of a cobalt carbonyl compound as catalyst, which is characterized in using as co-catalyst, a pyridine derivative having an amino substituent of formula (1), wherein R1 and R2 are independently hydrogen, formyl, acyl, alkoxycarbonyl, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or R1 and R2 may be taken together with the adjacent nitrogen atom to form a ring, and n is an integer of 1 or 2.Type: GrantFiled: February 20, 2004Date of Patent: August 14, 2007Assignee: Daiso Co., Ltd.Inventors: Kimitaka Igi, Yoshiro Furukawa, Keishi Takenaka
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Patent number: 7253300Abstract: In a process for producing tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester by reacting tricyclo[5.2.1.02,6]deca-3-ene with carbon monoxide and alcohol in the presence of HF, carried out separately are (a) a step in which tricyclo[5.2.1.02,6]deca-3-ene is reacted with carbon monoxide to produce acyl fluoride and (b) a step in which acyl fluoride obtained in the step described above is reacted with alcohol to produce an ester. Also, the reaction conditions at the step (a) described above are selected or a step for carrying out isomerization reaction of tricyclo[5.2.1.02,6]decane-2-carboxylic fluoride obtained at the step (a) is interposed between the step (a) and the step (b). Further, the crude product of tricyclo[5.2.1.02,6]decane-2-carboxylic acid ester thus obtained is subjected to contact treatment with specific glycol in the presence of an acid catalyst and then distilled.Type: GrantFiled: September 17, 2004Date of Patent: August 7, 2007Assignees: Mitsubishi Gas Chemical Company, Inc., Kao CorporationInventors: Mitsuharu Kitamura, Takashi Kojima, Yoshiharu Ataka, Tomoaki Kubota, Kinji Kato, Kazuyuki Fukuda
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Patent number: 6987199Abstract: The present invention relates to a new process for preparing beta-ketoester compound of the following formula (1), which is a useful intermediate for the synthesis of such quinoline antibiotics as Ciprofloxacin, Levofloxacin, Gemifloxacin, Trovafloxacin, etc. The quinoline antibiotics obtained from the above compound of formula (1) show potent antibacterial activity, and so are advantageously used as a therapeutic agent for bacterial infections of humans or animals.Type: GrantFiled: October 14, 2002Date of Patent: January 17, 2006Assignee: LG Life Sciences Ltd.Inventors: Hyun-lk Shin, Bo-Seung Choi, Sang-Chul Choi
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Patent number: 6960682Abstract: Acetyl anhydrides such as acetyl sulfate are produced by a process for comprising contacting methane and carbon dioxide in an anhydrous environment in the presence of effective amounts of a transition metal catalyst and a reaction promoter, and an acid anhydride compound, and optionally an acid. The acetyl anhydride can be contacted with water to produce acetic acid or with an alcohol to produce a product comprising an acetate ester and that may also comprise acetic acid. Optionally, water in stoichiometric amounts or less, with respect to the acetic anhydride, may be fed to a continuous process of this type to produce some acetic acid in situ.Type: GrantFiled: July 22, 2004Date of Patent: November 1, 2005Assignees: The Regents of the University of California, BP Chemicals LimitedInventors: Alexis T. Bell, Sudip Mukhopadhyay, Mark Zerella, John Glenn Sunley, Sander Gaemers, Michael James Muskett
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Patent number: 6806357Abstract: A method of effecting a nucleophilic substitution of an alcohol to produce a target product includes the steps of: reacting the alcohol and a nucleophile with an azodicarboxylate and a phosphine. At least one of the azodicarboxylate and the phosphine includes at least one fluorous tag. In several embodiments, the azodicarboxylate includes at least one fluorous tag, and the phosphine includes at least one fluorous tag. A compound has the formula: In the above formula n1, n2, n3, n4, n5, n6, n7, n8, n9 and n10 are independently 1 or 0. X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, X12, X13, X14, X15, X16, X17, X18, X19 and X20 are independently H, F, Cl, an alkyl group, an aryl group or an alkoxy group.Type: GrantFiled: August 20, 2001Date of Patent: October 19, 2004Assignee: University of PittsburghInventors: Dennis P. Curran, Sivaraman Dandapani
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Patent number: 6787671Abstract: An osmium-assisted process for the oxidative cleavage of oxidizable organic compounds such as unsaturated organic compounds, including alkenes and olefins into aldehydes, carboxylic acids, esters, or ketones. The process uses a metal catalyst comprising osmium and a peroxy compound selected from the group consisting of peroxymonosulfuric acid and salts thereof to oxidatively cleave the oxidizable organic compound. In particular, the process enables aldehydes, carboxylic acids, esters, or ketones to be selectively produced from the corresponding mono-, 1,1-di-, 1,2-di-, tri-, or tetra-substituted olefins in a reaction that produces the result of ozonolysis but with fewer problems. The present invention further provides a process for oxidizing an aldehyde alone or with the osmium in an interactive solvent to produce an ester or carboxylic acid.Type: GrantFiled: January 13, 2003Date of Patent: September 7, 2004Assignee: Board of Trustees of Michigan State UniversityInventors: Babak Borhan, Benjamin R. Travis, Jennifer M. Schomaker
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Patent number: 6737542Abstract: The present invention relates to a process for the carbonylation of conjugated dienes, whereby a conjugated diene is reacted with carbon monoxide and a hydroxyl group containing compound in the presence of a catalyst system including: (a) a source of palladium cations, (b) a phosphorus-containing ligand, (c) a source of anions, wherein the phosphorus-containing ligand is a ligand having the general formula (I): X1—R—X2 wherein X1 and X2 represent a substituted or non-substituted cyclic group with at least 5 ring atoms, of which one is a phosphorus atom, and R represents a bivalent organic bridging group, connecting both phosphorus atoms, containing from 1 to 4 atoms in the bridge, whereby the carbonylation process can be performed batch wise, semi-continuously or continuously.Type: GrantFiled: September 20, 2001Date of Patent: May 18, 2004Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
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Patent number: 6521783Abstract: This invention relates in part to a processes for the conversion of a feedstock stream comprising carbon monoxide and hydrogen to a product stream comprising at least one of an ester, acid, acid anhydride and mixtures thereof. This invention also relates in part to processes for converting an alcohol and/or ether feedstock to oxygenated products, e.g., esters, acids, acid anhydrides and mixtures thereof. The processes and catalysts are especially suitable for the production of acetic acid and methyl acetate from a synthesis gas feedstock or from an alcohol and/or ether feedstock.Type: GrantFiled: July 10, 2000Date of Patent: February 18, 2003Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard William Wegman, David McNeill Somerville, Barry Brent Fish, Raymond Edwin Rooks, Chinsoo Stephen Lee, Paul Frank Bryan, William J. Bartley, David Michael Anthony Minahan, Fungau Ho
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Patent number: 6392086Abstract: The present inventions relate to a (1S,5R,6S)- or (1SR, 5RS, 6SR)-3-fluoro-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylic acid derivative represented by Formula (1): [in the formula, R represents OR1 or NR1R2, wherein R1 and R2 are identical or different, and each represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a (C3-C6 cycloalkyl) (C1-C6 alkyl) group, an aryl group, an aryl (C1-C6 alkyl) group, a (C1-C6 alkoxy) (C1-C6 alkyl) group, a C1-C6 hydroxyalkyl group, a (C1-C6 alkylthio) (C1-C6 alkyl) group, or a C1-C6 mercaptoalkyl group], and a process for producing the same, and a process for efficiently producing a fluorine-containing amino acid compound acting on group 2 metabotropic glutamate receptors, which has treatment effects or prevention effects on psychiatric diseases or neurological diseases, characterized by hydrogenating the derivative, and subsequently, subjecting it to hydantoination or aminocyanidation, followed by hydrolysis.Type: GrantFiled: June 7, 2001Date of Patent: May 21, 2002Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Atsuro Nakazato, Toshihito Kumagai, Kazunari Sakagami, Kazuyuki Tomisawa, Hisanako Ito, Takeo Taguchi
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Patent number: 6353141Abstract: Functionalized cyclopentene-derived oligomer mixtures are prepared by reacting oligomer mixtures which contain ethyleneic double bonds in one or more reaction steps starting from cyclopentene-derived oligomer mixtures of the formula I R1R2C═[═CH—(CH2)3—CH═]n═CR3R4 (I) where n is an integer from 1 to 15, and R1, R2, R3 and R4 are, independently of one another, hydrogen or alkyl, and are used as described.Type: GrantFiled: June 21, 1999Date of Patent: March 5, 2002Assignee: BASF AktiengesellschaftInventors: Edgar Zeller, Gerhard Schulz, Bernhard Geissler, Michael Röper, Guido Voit
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Patent number: 6294688Abstract: A stereospecific method for accomplishing the below reaction: results in the compound of formula 2 having the same stereochemistry at both carbon 1 and carbon 3 as that in the compound of formula 1. Thus, if carbon 3 is in the R-configuration in the compound of formula 1, then carbon 3 will be in the R-configuration in the compound of resulting formula 2. In the above process, R1 is C1-C6 alkyl that can be straight-chain or branched. The process functions using a fluorinated alcohol having a pKa less than about 9, in the presence of a palladium catalyst. The compounds of formula 1, as well as novel intermediates in this process, are useful in manufacturing vitamin D analogs.Type: GrantFiled: August 7, 2000Date of Patent: September 25, 2001Assignee: Hoffman-La Roche Inc.Inventors: Andrzej Robert Daniewski, Marek Michal Kabat, Masami Okabe, Roumen Nikolaev Radinov
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Patent number: 6294687Abstract: The present invention discloses this invention relates to a process for the conversion of olefinically unsaturated compounds to corresponding carboxylic acids and their esters of formula III wherein R1, R2, R3 and R4 may independently be hydrogen, alkyl, aryl, arylalkyl, cycloaliphatic with or without substituents, R and R5 may be H and COOR′ or vice versa wherein R′ may be H in the case of acids and may be alkyl, aryl, arylalkyl, cycloaliphatic with or without substituents, in the case of esters, wherein said conversion is carried out in the presence of a transition metal complex catalyst of the formula.Type: GrantFiled: December 30, 1999Date of Patent: September 25, 2001Assignee: Council of Scientific and Industrial ResearchInventors: Raghunath Vitthal Chaudhari, A. Seayad, Jayasree Seayad
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Patent number: 6268526Abstract: A mixture formed from an aromatic substituted alcohol and/or an aromatic substituted alkyl halide, and a copper-free palladium catalyst is carbonylated with carbon monoxide. Extremely high yields of the desired alpha-substituted carboxylic acid can be obtained in very short reaction periods by use of a palladium catalyst that is formed from a palladium compound with a valence of zero to two and a cycloalkyldiarylphosphine ligand, such as neomenthyldiphenylphosphine.Type: GrantFiled: December 16, 1998Date of Patent: July 31, 2001Assignee: Albemarle CorporationInventor: Tse-Chong Wu
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Patent number: 6127574Abstract: A process for the production of a carboxylic acid and/or a carboxylic acid anhydride which process comprises contacting a reaction composition comprising an alcohol and/or a carboxylic acid ester, optionally water, a first hydrocarbyl halide and/or a hydrocarbyl ether reactant and a second hydrocarbyl halide promoter, the first and second hydrocarbyl halides being the same or different, with carbon monoxide in the presence of a catalyst comprising an insoluble imidazole-containing resin supporting a Group VIII metal species.Type: GrantFiled: June 16, 1998Date of Patent: October 3, 2000Assignee: BP Chemicals LimitedInventors: Mark Julian Howard, Michael David Jones
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Patent number: 6011171Abstract: The present invention provides a process for synthesizing tertiary carboxylic acids or the esters thereof having one or two more carbon atoms than the raw material has, comprising reacting in a strong acid (e.g., sulfuric acid, sulfuric acid-phosphoric acid, hydrogen fluoride, fluorosulfuric acid, boron trifluoride.water complex and trifluoromethanesulfonic acid) a raw material compound (i.e., olefin, alcohol, diene, diol or saturated hydrocarbon) with carbon monoxide in the presence of a specific metal carbonyl catalyst (i.e., platinum carbonyl catalyst, palladium carbonyl catalyst and gold dicarbonyl catalyst).The metal carbonyl catalyst is formed by reacting in a strong acid at least one specific metal compounds (e.g., platinum compound such as platinum (II, IV) oxide, platinum (II, IV) hydroxide, a platinum powder, etc.; palladium compound such as palladium (II, III, IV) oxide, palladium (II) hydroxide, palladium (II) sulfate, palladium (II) carboxylate, a palladium powder, etc.Type: GrantFiled: November 4, 1997Date of Patent: January 4, 2000Assignee: Jiro Hiraishi, Director-General, Agency of Industrial Science and TechnologyInventors: Qiang Xu, Yoshie Souma
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Patent number: 5639894Abstract: A process for the carbonylation of allylic alcohols such as nerolidol, farnesol, or their monocyclic analogues with carbon monoxide at a pressure of at least 30 bar in the presence of a polar solvent and a palladium halide catalyst, optionally an alkali metal halide salt, and optionally an alcoholic solvent. The carbonylated product may then be reduced to the corresponding alcohol, which is cyclized in the presence of Lewis or Bronsted acids to afford an ambergris fragrance compound.Type: GrantFiled: March 23, 1994Date of Patent: June 17, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Jonathan M. Cassel, Steven M. Hoagland, James M. Renga
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Patent number: 5378333Abstract: The disclosure describes photochemical synthesis of halogenated polycarboxycubanes from simple carboxycubanes and an oxalyl halide. It is possible to synthesize 6-Chloro-1,2,4,7-tetracarbomethoxycubane and 2-Chloro-1,3,5,7-tetracarbomethoxycubane. Photochemical synthesis of halogenated polycarboxycubanes from carboxy cubane and an oxalyl halide is reported.Type: GrantFiled: March 5, 1993Date of Patent: January 3, 1995Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Abdollah Bashir-Hashemi
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Patent number: 5324856Abstract: Disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) separating the diastereomers by conventional physical means and (3) hydrolyzing at least one of said separated diastereomers to make at least the .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid.Also disclosed is a process for making an .alpha.Type: GrantFiled: August 17, 1992Date of Patent: June 28, 1994Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 5258546Abstract: The invention relates to a catalyst system, which comprises a source of a Group VIII metal and a polyphosphine. The invention further relates to a process for the preparation of alpha, beta-olefinically unsaturated compounds utilizing this catalyst system.Type: GrantFiled: November 20, 1992Date of Patent: November 2, 1993Assignee: Shell Oil CompanyInventors: Peter A. Klusener, Hans A. Stil, Fit Drent, Peter Arnoldy
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Patent number: 5235119Abstract: An efficient direct functionalization of nitrocubanes has been achieved by irradiation of a solution in an oxalyl halide to yield halogenated and halocarbonylated derivatives of nitrocubanes.Type: GrantFiled: October 1, 1992Date of Patent: August 10, 1993Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Abdollah Bashir-Hashemi
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Patent number: 5216125Abstract: A process for producing an amide or an ester represented by the general formula W-A-B-Y which involves reacting an ester sulfonium salt represented by the general formula: ##STR1## with a nucleophilic agent represented by the general formulaH--B--Ywherein B represents a nucleophilic group, and wherein the members of the formula are further described in detail in the specification.Type: GrantFiled: June 20, 1989Date of Patent: June 1, 1993Assignee: Sanshin Kagaku Kogyo Co. Ltd.Inventor: Katsushige Kouge
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Patent number: 5214221Abstract: An efficient direct functionalization of nitrocubanes has been achieved by rradiation of a solution in an oxalyl halide to yield halogenated and halocarbonylated derivatives of nitrocubanes.Type: GrantFiled: October 1, 1992Date of Patent: May 25, 1993Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Abdollah Bashir-Hashemi
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Patent number: 5158921Abstract: A catalyst system, which containsa) a source of a group VIII metal, andb) a phosphine of general formula: ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are independently selected from an optionally substituted aryl group and a group of general formula: ##STR2## wherein eachh of A, X, Y and Z is independently selected from a nitrogen atom, a CH group and a group of formula CR wherein R represents a hydroxyl group, an amino group, an amido group, a cyano group, an aryl group, an aryloxy group, a halogen atom, an optionally substituted hydrocarbyl group or an optionally substituted hydrocarbyloxy group, it also being possible for two adjacent CR groups to form a ring, provided that at least one of R.sup.1, R.sup.2 and R.sup.3 represents a group of formula (II) in which at least one of A and Z represents a group of formula CR; or an acid addition salt thereof.Also disclosed is the use of the catalyst system in the selective carbonylation of unsaturated hydrocarbons.Type: GrantFiled: February 28, 1990Date of Patent: October 27, 1992Assignee: Shell Oil CompanyInventors: Eit Drent, Petrus H. M. Budzelaar, Willem W. Jager
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Patent number: 5153354Abstract: Cyclohexane derivatives containing carboxyl groups with the general structure of formula (I): ##STR1## alone or in mixtures with one another, in which the substituents on the cyclohexane ring are in the 1-, 2-, and 4-positions, Z is a --CH.sub.2 --CH.sub.2 -- group or a ##STR2## group, R is an alkyl group with 1 to 10 carbon atoms, and n is an integer of 1 to 3, are obtained by the hydrocarboxyalkylation of 1,2,4-trivinylcyclohexane and are useful as monomers for the formation of polymers.Type: GrantFiled: November 19, 1991Date of Patent: October 6, 1992Assignee: Huels AktiengesellschaftInventors: Wolfgang Schroder, Thomas Keil
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Patent number: 5149868Abstract: A process for the carbonylation of olefinically or alkynically unsaturated compounds with carbon monoxide in the presence of water and a catalyst, wherein the catalyst is based ona) a palladium compound,b) a phosphine general formula PR.sup.1 R.sup.2 R.sup.3, wherein R.sup.1, R.sup.2 and R.sup.3 are the same or different each represent an alkyl, cycloalkyl or aryl group, at least one of which carries a substituent selected from the group consisting of a sulphonic acid, phosphonic acid and carboxylic acid groups, or a salt thereof, andc) an anion of an acid having a pK.sub.a <3 (measured in water at 18.degree. C.) except hydrohalogenic acids,and wherein the reaction medium is at least initally a multiphase liquid reaction medium.Type: GrantFiled: March 19, 1991Date of Patent: September 22, 1992Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5145987Abstract: A process is disclosed for preparing cyclohexane tricarboxylic acids and esters thereof comprising contacting carbon monoxide, cis-1,2,3,6-tetrahydrophthalic acid anhydride and water or a lower alkanol at elevated pressure and temperature and in the presence of a palladium complex and an ether solvent wherein the selectivity to cis-1,2-trans-4-cyclohexane tricarboxylic acids and esters thereof is greater than that obtained in the absence of the ether solvent.Type: GrantFiled: May 22, 1991Date of Patent: September 8, 1992Assignee: The Dow Chemical CompanyInventor: David C. Molzahn
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Patent number: 5133903Abstract: Hydrocarboxyalkylation of .alpha.,.omega.-dienes with carbon monoxide and an alcohol in the presence of a cobalt compound and a tertiary amine gives .omega.-enecarboxylic acid esters with high selectivity and in good yields.Type: GrantFiled: February 28, 1989Date of Patent: July 28, 1992Assignee: Huels AktiengesellschaftInventors: Reinhold Gull, Thomas Keil
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Patent number: 5081292Abstract: .beta., .gamma.-Unsaturated carboxylic acids, e.g., 3-hexene-1,6-dioic acid, are selectively prepared by carbonylating (with carbon monoxide) an allyl alcohol, e.g., a butenediol, at an elevated temperature and under superatmospheric pressure, in the presence of a catalytically effective amount of a palladium-based catalyst and at least one quaternary onium chloride of one of the Group VB elements nitrogen or phosphorus, such element being tetracoordinated via carbon atoms and with the proviso that such nitrogen atom may be coordinated to two pentavalent phosphorus atoms.Type: GrantFiled: April 30, 1990Date of Patent: January 14, 1992Assignee: Rhone-Poulenc ChimieInventors: Philippe Denis, Jean Jenck, Robert Perron
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Patent number: 5075492Abstract: A method of manufacturing cyclooctanedicarboxylic acid diesters by hydrocarboxyalkylation of 1,5-cyclooctadiene over a cobalt catalyst in the presence of tertiary amines is disclosed.Type: GrantFiled: May 18, 1990Date of Patent: December 24, 1991Assignee: Huels AktiengesellschaftInventor: Thomas Keil