Geometric Isomer Formation (e.g., Cis-trans, Syn-anti, Etc.) Patents (Class 554/125)
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Patent number: 10773250Abstract: The present invention relates to a catalyst composition comprising a modified crystalline aluminosilicate of the Framework Type FER having Si/Al framework molar/ratio greater than 20 characterized in that in said modified crystalline aluminosilicate the ratio between the strong acid sites and the weak acid sites, S/W, is lower than 1.0 and having the extra framework aluminum (EFAL) content lowered to less than 10 wt % preferably 5 wt % even more preferably less than 2 wt % measured by 27Al MAS NMR. The present invention further relates to a process for producing olefins from alcohols in presence of said catalyst composition.Type: GrantFiled: November 12, 2019Date of Patent: September 15, 2020Assignee: Total Research & Technology FeluyInventors: Nikolai Nesterenko, Delphine Minoux, Nadiya Danilina, Jean-Pierre Dath, Vincent Coupard, Sylvie Maury
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Patent number: 10512903Abstract: The present invention relates to a catalyst composition comprising a modified crystalline aluminosilicate of the Framework Type FER having Si/Al framework molar ratio greater than 20 characterized in that in said modified crystalline aluminosilicate the ratio between the strong acid sites and the weak acid sites, S/W, is lower than 1.0 and having the extra framework aluminum (EFAL) content lowered to less than 10 wt % preferably 5 wt % even more preferably less than 2 wt % measured by 27 Al MAS NMR. The present invention further relates to a process for producing olefins from alcohols in presence of said catalyst composition.Type: GrantFiled: September 24, 2015Date of Patent: December 24, 2019Assignees: TOTAL RESEARCH & TECHNOLOGY FELUY, IFP ENERGIES NOUVELLESInventors: Nikolai Nesterenko, Delphine Minoux, Nadiya Danilina, Jean-Pierre Dath, Vincent Coupard, Sylvie Maury
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Patent number: 10112186Abstract: Disclosed are a beta molecular sieve, a preparation method therefor, and a hydrogenation catalyst containing same. The properties of the beta molecular sieve are as follows: the molar ratio of SiO2/Al2O3 is 30-150, the non-framework aluminum accounts for not more than 2% of the total aluminum, and the silicon atoms coordinated in a Si(OAl) structure account for not less than 95% of the silicon atoms in the framework structure. The preparation method comprises: contacting the raw material powder of the beta molecular sieve with normal pressure and dynamic water vapor, and then with ammonium fluosilicate. The beta molecular sieve of the present invention has the features of a uniform skeleton structure of silicon and aluminum, an appropriate acidity, and a reasonable pore structure, and is suitable as an acidic component of a hydro-upgrading catalyst and a hydro-cracking catalyst for diesel oil.Type: GrantFiled: October 28, 2014Date of Patent: October 30, 2018Assignees: CHINA PETROLEUM & CHEMICAL CORPORATION, FUSHUN RESEARCH INSTITUTE OF PETROLEUM AND PETROCHEMICALS, SINOPEC CORP.Inventors: Chang Liu, Fenglai Wang, Keqi Wang, Yanze Du, Hong Zhao, Minghua Guan
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Patent number: 9518002Abstract: Methods of carrying out metathesis reactions of natural oil-derived polyenes (e.g., dienes and trienes), including functionalized polyenes, are generally disclosed herein. In some embodiments, the dienes or trienes contain a terminal carbon-carbon double bond, and the metathesis reaction is selective toward reaction of the terminal carbon-carbon double bonds in the polyene. Compounds made by such methods are also generally disclosed herein.Type: GrantFiled: October 19, 2015Date of Patent: December 13, 2016Assignee: Elevance Renewable Sciences, Inc.Inventors: Keith M. Wampler, Jane Uy, Steven A. Cohen
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Patent number: 9382502Abstract: Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fatty acid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having unsaturated esters.Type: GrantFiled: March 14, 2013Date of Patent: July 5, 2016Assignee: Elevance Renewable Sciences, Inc.Inventors: Thomas E. Snead, Steven A. Cohen, Demond L. Gildon, Leslie V. Beltran, Linda A. Kunz, Tessa M. Pals, Jordan R. Quinn, Raymond T. Behrends, Jr., Randal J. Bernhardt
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Publication number: 20140336100Abstract: Chemically modified lipids and methods for their preparation are provided.Type: ApplicationFiled: July 22, 2014Publication date: November 13, 2014Inventors: Anthony G. Day, Geoffrey Brooks, Scott Franklin
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Patent number: 8853434Abstract: The invention relates to a process for the isomerization of unsaturated fatty acids or esters or amides thereof, said process comprising reacting: (a) an unsaturated fatty acid or ester or amide thereof; (b) a source of Pd; (c) a bidentate diphosphine of formula I, R1R2>P1-R—P2<R3R4??(I) wherein P1 and P2 represent phosphorus atoms; R1, R2, R3 and R4 represent tert-butyl; and wherein R represents an optionally substituted aromatic group spanning P1 and P2; (d) a lower alcohol; and (e) an acid co-catalyst, under conditions for isomerization to take place. The process is particularly advantageous for the isomerization of substituted alkenes harboring a hydroxy group when the desired end product has a keto group, such as ricinoleic acid or ester thereof.Type: GrantFiled: July 12, 2012Date of Patent: October 7, 2014Assignee: DSM IP Assets B.V.Inventors: Natascha Sereinig, Michèle Catherine Christianne Janssen, Johannes Gerardus De Vries
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Patent number: 8809560Abstract: This invention relates generally to trans-,trans-conjugated linoleic acid compositions and use thereof, and in particular to trans-,trans-conjugated linoleic acid produced from photoisomerization of soy oil in the presence of an antioxidant, and used in pharmaceutical, nutraceutical and human and animal food compositions for improved health. The invention also relates generally to a method for treatment and prevention of health-related disorders of obesity by administration of pharmaceutical, nutraceutical and/or food compositions containing and/or prepared from trans-,trans-conjugated linoleic acid-rich soy oil.Type: GrantFiled: May 15, 2012Date of Patent: August 19, 2014Assignee: Board of Trustees of the University of ArkansasInventors: Andrew Proctor, Reddy Yettella Yenkata Ramesh, Latha Devareddy, Robert R. Beitle
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Publication number: 20140187803Abstract: The invention provides a new method for the preparation of the dimeric Pd(l) tri-tert.-butylphosphine bromide complex, characterized by the chemical formula [Pd(?-Br)(PtBu3)]2. The method is based on a comproportionation reaction in which a Pd(ll) compound (=PdBr2) is reacted with a Pd(0) compound (=Pd(PtBu3)2) in organic solvents to yield the [Pd(?-Br)(PtBu3)]2 compound having the Pd atoms in the formal oxidation state +1. Unreacted PdBr2 may be reused in the process. The method is straightforward and applicable for industrial scale production and provides high product yields. Further, a new process for the isomerization of allyl ethers of the general type R1—C(O)—O—CH(R2)—C(R3)?CH2 employing the compound Pd?-Br)(PtBu3)]2 as a catalyst is disclosed.Type: ApplicationFiled: June 25, 2012Publication date: July 3, 2014Applicant: Umicore AG & Co. KGInventors: Lukas Goossen, Matthias Arndt, Patrizia Mamone, Matthias Gruenberg
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Patent number: 8748641Abstract: A process for preparing saturated branched chain fatty acids or alkyl esters thereof involving subjecting unsaturated fatty acids having 10 to 25 carbon atoms, alkyl esters thereof or mixtures thereof to a skeletal isomerization reaction in the presence of water or a lower alcohol at a temperature of about 240° C. to about 280° C. using a combination of a stericly hindered Lewis base and zeolite as a Brönsted or Lewis acid catalyst, and isolating saturated branched chain fatty acids or alkyl esters thereof or mixtures thereof from the reaction mixture obtained by the skeletal isomerization reaction. The yield of said saturated branched chain fatty acids is ?70 wt %. The stericly hindered Lewis base is a tertiary amine or phosphine with linear or branched C1 to C6 alkyl or phenyl groups attached thereto.Type: GrantFiled: May 5, 2010Date of Patent: June 10, 2014Assignee: The United States of America, as represented by The Secretary of AgricultureInventors: Helen Ngo, Thomas A. Foglia
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Publication number: 20140046081Abstract: The invention relates to a method for producing compositions containing unsaturated compounds, wherein (A) one or more unsaturated monocarboxylic acids having 10 to 24 C-atoms or esters of said monocarboxylic acids and optionally (B) one or more compounds having at least one C?C double bond (wherein the compounds (B) are different from the compounds (A)) are subjected to a tandem isomerization/metathesis reaction sequence in the presence of a palladium catalyst and a ruthenium catalyst, providing that the palladium catalysts used are compounds that contain at least one structural element Pd—P(R1R2R3), wherein the radicals R1 to R3, independently of one another, each comprise 2 to 10 C-atoms, which may be aliphatic, alicyclic, aromatic or heterocyclic respectively, providing that at least one of the radicals R1 to R3 contains a beta-hydrogen, wherein the palladium catalyst is used as such or is produced in situ, providing that the method is carried out in the absence of substances that have a pKa value of 3 orType: ApplicationFiled: February 25, 2012Publication date: February 13, 2014Applicant: COGNIS IP MANAGEMENT GmbHInventors: Lukas J. Goossen, Dominik Ohlmann, Markus Dierker
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Patent number: 8536373Abstract: Improved method of production of 9-(Z)-retinoic acid, in which a) a ?-formyl-crotonic acid C1-C10 alkyl or phenyl ester is reacted with an isolated 9-(Z)—C15-triarylphosphonium salt by the Wittig reaction in the presence of a base to the corresponding 9-(Z)-retinoic acid ester; which b) is then saponified with a base to the corresponding 9-(Z)-retinoic acid carboxylate and then, following protonation with an acid, the desired 9-(Z)-retinoic acid is obtained, and improved method for the enrichment and isolation of the 9-(Z)—C15-triarylphosphonium salt.Type: GrantFiled: September 27, 2007Date of Patent: September 17, 2013Assignee: DSM IP Assets B.V.Inventors: Michael Stanek, Stefan Essl, Monika Knopp, Erwin Kübel
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Publication number: 20130204022Abstract: Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fatty acid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having unsaturated esters.Type: ApplicationFiled: March 14, 2013Publication date: August 8, 2013Applicant: ELEVANCE RENEWABLE SCIENCES, INC.Inventor: ELEVANCE RENEWABLE SCIENCES, INC.
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Patent number: 7619103Abstract: The present invention generally relates to a process for the arylation of unsaturated linear fatty acids and/or alkyl esters thereof to their aryl branched counterparts. Said arylation process comprises contacting said unsaturated linear fatty acids and/or alkyl esters thereof and one or more aromatic compounds with at least one metal ion exchanged solid material catalyst. The invention also relates to various derivatives prepared from the aryl branched fatty acids and/or alkyl esters prepared in accordance with the present invention.Type: GrantFiled: July 16, 2004Date of Patent: November 17, 2009Assignee: Akzo Nobel N.V.Inventors: Zongchao Zhang, Shuguang Zhang, James F. Gadberry
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Publication number: 20090107034Abstract: A method of producing a fatty acid alkyl ester, containing: conducting an transesterification reaction of an oil or/and fat with a straight-chain or branched alcohol having 1 to 4 carbon atoms, in the presence of a phosphoric acid alkali-metal salt; and a fuel containing the fatty acid alkyl ester produced by the method in a given ratio.Type: ApplicationFiled: September 13, 2006Publication date: April 30, 2009Applicant: FUJIFILM CORPORATIONInventor: Hirofumi Fukunaga
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Patent number: 7485738Abstract: This invention has disclosed a method for preparation of food-grade zeaxanthin through chemical isomerizaton reaction from lutein. The technical issues to be solved in this invention are quite low product yield obtained with existing methods, need of purification treatment process, and inadaptability to industrialized production. The technical schemes of this invention are: a. Mix xanthophyll crystal or its fatty acid ester with food-grade glycol or propylene glycol, for full dissolution under 60-90° C. temperature. Add organic alkali into the mixed liquor acquired from step 1, for isomerization reaction to take place under inertial environment. c. Dilute the reaction solution gained from step b with the mixed solution of deionized water and ethanol, and separate the obtained crystal with conventional separating method. d. Vacuum dries the acquired crystal from step c, to get the zeaxanthin crystal.Type: GrantFiled: September 18, 2007Date of Patent: February 3, 2009Assignee: Zhejiang Medicine Co., Ltd., XinChang Pharmaceutical FactoryInventors: Xinde Xu, Lihua Zhang, Boqiu Chen, Di Zhou, Shuangming Ye, Chiyu Ding, Hongping Lv, Bin Shao
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Patent number: 7423163Abstract: An easy and inexpensive process by which a concentrate of a given unsaturated fatty acid can be obtained from a mixture which has conventionally been difficult to concentrate. The process, which is for producing a concentrate of a desired isomer (a) from a conjugated fatty acid mixture (A), is characterized by comprising: a step in which the conjugated fatty acid mixture (A) is mixed with at least one unsaturated fatty acid (B) to obtain a mixture solution containing the isomer (a) dissolved therein; a crystallization step in which either crystals rich in the isomer (a) or crystals poor in the isomer (a) are precipitated from the mixture solution; and a solid-liquid separation step for obtaining the crystals rich in the isomer (a) or for obtaining a solution rich in the isomer (a) by removing the crystals poor in the isomer (a).Type: GrantFiled: September 20, 2007Date of Patent: September 9, 2008Assignee: The Nisshin Oillio Group, Ltd.Inventors: Hidetaka Uehara, Tomomi Suganuma, Satoshi Negishi, Toshihisa Suzuki
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Patent number: 7071345Abstract: The claimed method for preparing conjugated polyunsaturated fatty acid esters consisting of an alcohol radical R1 having from 1 to 5 carbon atoms and a fatty acid radical R2 having from 10 to 24 carbon atoms, together with alkoxides having from 1 to 5 carbon atoms, comprises carrying out the reaction solvent-free using a phase-transfer catalyst. In this method, the contents of the fatty acid ester should be from 85 to 99.9% by weight, those of the alkoxide component from 0.05 to 10% by weight, and those of the phase-transfer catalyst from 0.05 to 5.0% by weight, in each case based on the total reaction mixture. Esters of linoleic acid and linolenic acid are preferred as starting material, just as sodium or potassium methoxide or sodium or potassium ethoxide are preferred as alkoxide. Suitable phase-transfer catalysts are, for example, polyethylene glycols, polyethylene glycol monomethyl ethers or polyethylene glycol dimethyl ethers, crown ethers and quaternary ammonium or phosphonium salts.Type: GrantFiled: October 25, 2004Date of Patent: July 4, 2006Assignee: Bioghurt Biogarde GmbH & Co. KGInventors: Hans Henning Wenk, Katrin Haeser
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Patent number: 7057058Abstract: A process for the preparation of 13-cis-retinoic acid (I) from 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl)-triphenylphosphonium chloride (IIa) and 5-hydroxy-4-methyl-2(5H)-furanone (III) is herein disclosed. Compounds (IIa) and (III) are reacted in ethanol as the solvent and KOH as the base at a temperature ranging from ?5 to 0° C. to give a mixture of retinoic acids which is isomerized to (I) by treatment with a palladium complex.Type: GrantFiled: February 16, 2005Date of Patent: June 6, 2006Assignee: Helsinn Advanced Synthesis SAInventors: Waldo Mossi, Patrizio Aspari, Enrico Braglia, Riccardo Braglia
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Patent number: 6946567Abstract: The present invention relates to a process for the skeletal isomerization of unsaturated linear fatty acids to branched fatty acids which comprises contacting said unsaturated linear fatty acids with at least one large pore zeolite catalyst wherein said at least one zeolite catalyst comprises a material having a three dimensional channel structure having a pore diameter of at least 6.0 ?. In another embodiment, the invention relates to a process for the skeletal isomerization and hydrogenation of unsaturated linear fatty acids to saturated branched fatty acids which comprises contacting said unsaturated linear fatty acids in the presence of an acidic catalyst, wherein said acidic catalyst comprises a mesoporous crystalline phase having pore walls containing primary and secondary crystalline building unit structures.Type: GrantFiled: January 9, 2003Date of Patent: September 20, 2005Assignee: Akzo Nobel N.V.Inventors: Shuguang Zhang, Zongchao Zhang, Dale Steichen
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Publication number: 20040204598Abstract: The present invention generally relates to a process for the skeletal isomerization of unsaturated linear fatty acids and/or alkyl esters thereof to their branched counterparts. Said skeletal isomerization process comprises contacting said unsaturated linear fatty acids and/or alkyl esters thereof with at least one metal ion exchanged solid material catalyst. The present invention also relates to a process for the preparation of branched fatty acids and/or alkyl esters thereof from their straight chain counterparts. Finally, the invention also relates to various derivatives prepared from the branched fatty acids and/or alkyl esters prepared in accordance with the present invention.Type: ApplicationFiled: April 11, 2003Publication date: October 14, 2004Inventors: Zongchao Zhang, Shuguang Zhang
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Patent number: 6723862Abstract: The present invention generally relates to a process for the preparation of branched fatty acids from straight chain unsaturated fatty acid feedstocks with a strongly acidic and hydrothermally stable mesoporous aluminosilicate and/or aluminophosphate catalyst materials having mesopores of 15-500 Å and contain primary and secondary nanosized zeolite structural units in the walls that separate mesopores.Type: GrantFiled: March 18, 2003Date of Patent: April 20, 2004Assignee: Akzo Nobel N.V.Inventors: Zhang Shuguang, Zhang Zongchao
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Publication number: 20030191331Abstract: The present invention generally relates to a process for the preparation of branched fatty acids from straight chain unsaturated fatty acid feedstocks with a strongly acidic and hydrothermally stable mesoporous aluminosilicate and/or aluminophosphate catalyst materials having mesopores of 15-500 Å and contain primary and secondary nanosized zeolite structural units in the walls that separate mesopores.Type: ApplicationFiled: March 18, 2003Publication date: October 9, 2003Inventors: Zhang Shuguang, Zhang Zongchao
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Publication number: 20030100780Abstract: The present invention relates to a process for the skeletal isomerization of unsaturated linear fatty acids to branched fatty acids which comprises contacting said unsaturated linear fatty acids with at least one large pore zeolite catalyst wherein said at least one zeolite catalyst comprises a material having a three dimensional channel structure having a pore diameter of at least 6.0 Å. In another embodiment, the invention relates to a process for the skeletal isomerization and hydrogenation of unsaturated linear fatty acids to saturated branched fatty acids which comprises contacting said unsaturated linear fatty acids with at least one metal-zeolite catalyst.Type: ApplicationFiled: June 21, 2002Publication date: May 29, 2003Inventors: Shuguang Zhang, Zongchao Zhang, Dale Steichen
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Patent number: 6479683Abstract: This invention relates to a process for producing conjugated fatty acid esters. More particularly, this invention relates to a process for producing conjugated fatty acid esters comprising subjecting one or a mixture of unconjugated fatty acid esters to a base-catalyzed isomerization reaction in the presence of only small amounts of catalyst and solvent in a closed vessel at an elevated temperature and under the corresponding autogenic pressure.Type: GrantFiled: March 6, 2001Date of Patent: November 12, 2002Assignee: Ag Processing IncInventors: Curt Abney, John Anderson
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Patent number: 6380409Abstract: Novel compositions containing conjugated linoleic acid isomers can be used for controls in gas chromatography and for animal feeding studies. Purified isomers of conjugated linoleic acid can be treated to produce a preparation containing two isomers of CLA. The preparation can be used as is or further processed to separate the two isomers. The isomers can be used in their free fatty acid form or converted to alkylesters or triglycerides. Furthermore, the isomers are useful as supplements for food products or feed.Type: GrantFiled: April 24, 2000Date of Patent: April 30, 2002Assignee: Conlin Co., Inc.Inventors: Asgeir Saebo, Per Christian Saebo
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Publication number: 20010044550Abstract: A process for the branching of saturated and/or unsaturated fatty acids and/or alkyl esters thereof comprises subjecting the fatty acids and/or alkyl esters to a skeletal isomerization reaction using a catalyst comprising a crystalline porous structure having incorporated therein a metal to form metal sites on said catalyst and isolating branched fatty acids, alkyl esters thereof, or mixtures thereof, from a reaction mixture obtained by said skeletal isomerization reaction. The catalyst used in the isomerization reaction is preferably a zeolite catalyst containing metal sites of a Group VIII metal. The process produces a mixture of fatty acids and/or alkyl esters that contain significant quantities of branched molecules.Type: ApplicationFiled: March 2, 2001Publication date: November 22, 2001Inventors: Corey James Kenneally, Daniel Stedman Connor
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Publication number: 20010018533Abstract: The process of the present invention relates to a process for producing 1 3-cis retinoic acid. The process of the present invention involves reacting a Wittig salt in a solvent with a butenolide in the presence of a weak base and optionally, a Lewis acid.Type: ApplicationFiled: January 18, 2000Publication date: August 30, 2001Inventors: Xiu C. Wang, Ashok V. Bhatia, Azad Hossain, Timothy B. Towne
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Patent number: 6177579Abstract: A process for the synthesis of 13-cis-retinoic acid with high purity and stability, without using heavy metals at any steps, starting from vinyl-beta-ionol prepared from ionone and vinyl magnesium halides.Type: GrantFiled: May 17, 1999Date of Patent: January 23, 2001Assignee: Laboratori Mag S.p.A.Inventor: Angelo Magnone Grato
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Production of materials rich in conjugated isomers of long chain polyunsaturated fatty acid residues
Patent number: 6160140Abstract: The invention concerns an isomerisation process, wherein materials comprising non-congugated long chain polyunsaturated fatty acids are subjected to base in the presence of an alcohol with .gtoreq.3 C-atoms and .gtoreq.2 OH groups and having ratio C-atoms: OH-groups of .gtoreq.1.25. The resulting reaction product, containing the conjugated isomers is obtained in higher yield at lower temperatures and are not contaminated by presence of non food grade solvent.Type: GrantFiled: September 11, 1998Date of Patent: December 12, 2000Assignee: Unilever Patent Holdings BVInventors: Krish Bhaggan, Frederick William Cain, John Bernard Harris, Victoria Taran -
Patent number: 6140512Abstract: A process for the preparation of lipolic acid (thioctic acid), or a derivative thereof, is one in which a 2-substituted cyclohexanone is transformed in an oxidation reaction to a lactone having formula (I), wherein X is a heteroatom substituent.Type: GrantFiled: May 12, 1999Date of Patent: October 31, 2000Assignee: ASTA Medica AktiengesellschaftInventors: Brian Michael Adger, Raymond McCague, Stanley Michael Roberts
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Patent number: 6124485Abstract: The process of the present invention relates to a process for producing 1 3-cis retinoic acid. The process of the present invention involves reacting a Wittig salt in a solvent with a butenolide in the presence of a weak base and a Lewis acid.Type: GrantFiled: March 25, 1998Date of Patent: September 26, 2000Assignee: Abbott LaboratoriesInventors: Xiu C. Wang, Ashok V. Bhatia, Azad Hossain, Timothy B. Towne
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Patent number: 5917067Abstract: A process for producing an omega-functionalized aliphatic carboxylic acid starting from cyclohexanone and omega-functionalized .alpha.-olefins or acrylic esters. The process comprises an addition step, an oxidation step, an isomerization step, and one or more hydrogenation steps. The process allows to use raw materials that are available at low cost and to achieve high selectivity and high yield with industrially simple steps. The process includes the production of new intermediate products, including 2-oxepanone-7-substituted products.Type: GrantFiled: April 18, 1996Date of Patent: June 29, 1999Assignee: Industrie Chimiche Caffaro S.P.A.Inventors: Livius Cotarca, Paolo Maggioni, Alfonso Nardelli, Stefano Sguassero
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Patent number: 5892073Abstract: Photochemical isomerization of 11-cis-, 13-cis-retinoic acid to 13-cis-retinoic acid characterized in that it is performed in an aqueous solution of an alkaline salt of said 11-cis-, 13-cis-retinoic acid.Type: GrantFiled: December 22, 1997Date of Patent: April 6, 1999Assignee: Laboratori Mag S.p.A.Inventor: Angelo Grato Magnone
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Patent number: 5856539Abstract: It was found that the conversion (by isomerisation or branching) of unsaturated fatty acids into branched fatty acids can be catalysed by materials having a microporous structure. Such a process gives high conversion rates and a high selectivity towards branched fatty acids, whilst a low amount of undesired by-products is obtained. Zeolites are preferred materials for catalysing said reaction.Type: GrantFiled: November 18, 1996Date of Patent: January 5, 1999Assignee: Unichema Chemie B.V.Inventors: William R. Hodgson, Wicher Tijmen Koetsier, Cornelis Martinus Lok, Glyn Roberts
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Patent number: 5677473Abstract: A process for preparing branched chain fatty acids or alkyl esters thereof comprising at least a step wherein unsaturated fatty acids having 10 to 25 carbon atoms, alkyl esters thereof or mixtures thereof are subjected to skeletal isomerization reaction in the presence of water or a lower alcohol at a temperature of 150.degree. to 350.degree. C. using a zeolite as a catalyst, the zeolite having a linear pore structure of pore size that is small enough to retard dimerization and large enough to allow diffusion of the branched chain fatty acids or alkyl esters thereof.Type: GrantFiled: May 17, 1995Date of Patent: October 14, 1997Assignee: Kao CorporationInventors: Takeshi Tomifuji, Hiroshi Abe, Yoshihisa Matsumura, Yasumitsu Sakuma
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Patent number: 5532421Abstract: An object of the present invention is to provide a method for the preparation of geometrical isomers which are important as constituents of synthetic pheromones, synthetic perfumes, terpenes and the like (i.e., a method for the isomerization of cis-alkenyl compounds to their trans-isomers). In this method, the above-described object is accomplished by reacting a cis-alkenyl compound in the presence of nitric acid used as the sole catalyst.Type: GrantFiled: July 19, 1994Date of Patent: July 2, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takanobu Terauchi, Toyohisa Sakurada, Takehiko Fukumoto, Hiroshi Suzuki
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Patent number: 5424465Abstract: 13-(Z)-Retinoic acid is prepared bya) reacting 5-hydroxy-4-methyl-2(5H)-furanone with a [3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl]triarylpho sphonium salt andb) subsequently partially isomerizing the resulting mixture of 13-(Z)- and 11,13-di-(Z)-retinoic acid,where the reaction in step a) is carried out in the presence of lithium hydroxide as alkali metal hydroxide and in dimethylformamide as solvent at from +10.degree. to -9.degree. C. and/or the isomerization in step b) is carried out by irradiating the mixture of isomers obtained in a) in an organic solvent in the presence of a photosensitizer with light in the wavelength range from 200 to 600 nm.Type: GrantFiled: March 31, 1994Date of Patent: June 13, 1995Assignee: BASF AktiengesellschaftInventors: Michael John, Joachim Paust
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Patent number: 5218138Abstract: This invention is directed to a method for stereoselectively preparing a syn-dihydroxylated compound comprising reacting a 3-hydroxyket-1-one and a sterically hindered dialkylated borane to form a complex at about -50.degree. C. to about 0.degree. C., and reducing the complex with hydride at about -25.degree. C. to about 50.degree. C.Type: GrantFiled: September 2, 1992Date of Patent: June 8, 1993Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Fang-Ting Chiu, William L. Studt
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Patent number: 5196571Abstract: Unsaturated monoesters of the formula (I) ##STR1## are prepared from diesters of the formula (II) ##STR2## where the radicals R.sup.1 to R.sup.5 in the formulae (I) and (II) are identical to each other and each is hydrogen, straight-chain or branched alkyl or alkenyl of from 1 to 10 carbon atoms, cycloalkyl or cycloalkylene of from 5 to 8 carbon atoms, aryl, alkylaryl or aralkyl, by reaction in the presence of a zeolite and/or phosphate as a catalyst with the elimination of a carboxylic acid R.sup.6 COOH where R.sup.6 is hydrogen or alkyl of from 1 to 6 carbon atoms, n being an integer from 1 to 10.Type: GrantFiled: December 30, 1991Date of Patent: March 23, 1993Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Hardo Siegel