Forming Carbon To Carbon Unsaturation (i.e., Forming A Double Or Triple Bond) Patents (Class 554/127)
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Patent number: 11365171Abstract: The invention relates to a process for preparing an ester by alkoxycarbonylation of a C2 to C20 hydrocarbon having at least one multiple bond, preferably having at least one olefinic double bond, in which the homogeneous catalyst system used is separated from the product mixture by means of membrane separation and recycled into the reaction zone. In a development of the present invention, the ester thus formed is converted into another ester by transesterification.Type: GrantFiled: June 5, 2020Date of Patent: June 21, 2022Assignee: Evonik Operations GmbHInventors: Peter Kucmierczyk, Robert Franke, Dirk Fridag, Johannes Knossalla, Marc Schäpertöns, Frederik Gluth
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Patent number: 10280132Abstract: A carboxylic acid is transvinylated with vinyl ester to give a vinyl ester product and the corresponding acid of the vinyl ester in the presence of a catalyst, at a temperature of 100° C. to 170° C. and a pressure of 2 bar abs. to 15 bar abs., wherein the vinyl ester, the carboxylic acid and the catalyst are supplied to a reactor, the transvinylation reaction is conducted, and, on the completion of the transvinylation, the vinyl ester product is separated from the reaction mixture by distillation, characterized in that the reaction mixture is decompressed in a decompression vessel, the gaseous phase obtained is condensed and recycled into the reactor without further purification, and the liquid phase obtained is freed of vinyl ester and corresponding acid with a first distillation, and the vinyl ester product is separated from the reaction mixture in a further distillation step.Type: GrantFiled: August 3, 2016Date of Patent: May 7, 2019Assignee: WACKER CHEMIE AGInventors: Peter Schultheiss, Volker Hoellein, Brigitte Patsch
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Patent number: 9518277Abstract: Genetically engineered microbial, e.g., Chlorella protothecoides, cells producing microbial oils are useful as a food additive and a source of renewable fuels and industrial chemicals. Lipid biosynthesis genes for Auxenochlorella protethecoides are disclosed that are useful for increasing lipid production and altering fatty acid and triacylglycerol profiles in recombinant microrganisms including cells of the genus Auxenochlorella or Prototheca.Type: GrantFiled: December 6, 2013Date of Patent: December 13, 2016Assignee: TerraVia Holdings, Inc.Inventors: Scott Franklin, Shane Brubaker, George N. Rudenko, Riyaz Bhat, Matthew Shoa-Azar, Aravind Somanchi, Aren Ewing
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Patent number: 9227907Abstract: The present invention relates to new organic compounds, to their synthesis as well as to their use in organic synthesis, especially in processes forming intermediates (building blocks) for the synthesis of vitamin A or ?-carotene or other carotenoids.Type: GrantFiled: June 14, 2012Date of Patent: January 5, 2016Assignee: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Thomas Netscher, Jan Schütz, Bettina Wüstenberg
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Publication number: 20150112087Abstract: According to embodiments of present disclosure, a method to produce a compound of Formula 19 is provided. Using this method, the compound of Formula 19 may be produced effectively.Type: ApplicationFiled: August 8, 2014Publication date: April 23, 2015Inventor: YONG XU
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Patent number: 8802222Abstract: The present invention relates to a radiation curable composition comprising (a) from 1 to 99% by weight of a (meth)acrylated natural oil which is the reaction product of an unsaturated natural oil with an unsaturated anhydride and a hydroxyl functional (meth)acrylate, and (b) from 1 to 99% by weight of a (meth)acrylated oligomer and/or monomer, and optionally an inert resin and/or filler, as well as their use for making inks and coatings.Type: GrantFiled: July 31, 2013Date of Patent: August 12, 2014Assignee: Allnex Belgium S.A.Inventors: Jeff Vanderlip, Karen Shuler, Rosalyn Waldo, Thierry Randoux
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Patent number: 8314262Abstract: The invention broadly relates to the use of ?,?-unsaturated fatty acids to inhibit the filamentous growth of fungi and yeasts and to a method for producing same. In particular the invention relates to the use of optionally substituted C8 to C15 ?,?-unsaturated fatty acids or salts, esters or amides thereof for inhibiting or retarding the yeast-to-mycelium transition of organisms having a dimorphic life cycle.Type: GrantFiled: April 12, 2010Date of Patent: November 20, 2012Assignee: Agency for Science, Technology and ResearchInventors: Lian-Hui Wang, Lian-Hui Zhang
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Patent number: 8203012Abstract: A process for preparing conjugated linoleic acid (CLA) or derivatives thereof from ricinoleic acid, lower alkyl esters of ricinoleic acid, or salts thereof. The CLA is formed by reacting a carboxylic acid, or anhydride, anhydride equivalent, or ester thereof with the ricinoleic acid or derivative to form an intermediate having a carboxylic ester at the 12-hydroxy position of the ricinoleic acid or derivative, and reacting the intermediate with a base to form a cis-9, trans-11 conjugated linoleic acid.Type: GrantFiled: December 5, 2006Date of Patent: June 19, 2012Assignee: Stepan CompanyInventors: Joseph C. Rongione, Jenifer Heydinger Galante, Randal J. Bernhardt
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Patent number: 7928254Abstract: The invention concerns a method for preparing a compound of formula (I), wherein: R3 and R1 represent in particular H and n is greater than 4, said preparation method including performing a Wittig-Horner reaction with a phosphonate on a lactol, so as to obtain a hydroxyester and, optionally a saponification reaction of said hydroxyester.Type: GrantFiled: October 10, 2006Date of Patent: April 19, 2011Assignee: Pierre Fabre Dermo-CosmetiqueInventors: Natacha Frison, Benoit Folleas, Jean-Louis Brayer
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Publication number: 20110015417Abstract: The invention provides methods of cultivating oil-bearing microbes using xylose alone or in combination with other depolymerized cellulosic material. Also provided are microorganisms comprising an exogenous gene encoding a polysaccharide degrading enzyme, such as a cellulase, a hemicellulase, a pectinase, or a driselase. Some methods of microbial fermentation are provided that comprise the use of xylose and depolymerized cellulosic materials for the production of oil-bearing microorgansims.Type: ApplicationFiled: April 30, 2010Publication date: January 20, 2011Applicant: Solazyme, Inc.Inventors: Donald E. Trimbur, Chung-Soon Im, Harrison F. Dillon, Anthony G. Day, Scott Franklin, Anna Coragliotti
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Publication number: 20100197948Abstract: The invention broadly relates to the use of ?,?-unsaturated fatty acids to inhibit the filamentous growth of fungi and yeasts and to a method for producing same. In particular the invention relates to the use of optionally substituted C8 to C15 ?,?-unsaturated fatty acids or salts, esters or amides thereof for inhibiting or retarding the yeast-to-mycelium transition of organisms having a dimorphic life cycle.Type: ApplicationFiled: April 12, 2010Publication date: August 5, 2010Inventors: Lian-Hui WANG, Lian-Hui ZHANG
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Patent number: 7745651Abstract: The present invention provides compositions comprising cationic lipids, liposomes and nucleic acid-lipid particles comprising the cationic lipids, and methods of using such compositions, liposomes, and nucleic acid-lipid particles.Type: GrantFiled: June 7, 2005Date of Patent: June 29, 2010Assignee: Protiva Biotherapeutics, Inc.Inventors: James Heyes, Ian MacLachlan, Lorne R. Palmer
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Publication number: 20100036142Abstract: A process for preparing conjugated linoleic acid (CLA) or derivatives thereof from ricinoleic acid, lower alkyl esters of ricinoleic acid, or salts thereof. The CLA is formed by reacting a carboxylic acid, or anhydride, anhydride equivalent, or ester thereof with the ricinoleic acid or derivative to form an intermediate having a carboxylic ester at the 12-hydroxy position of the ricinoleic acid or derivative, and reacting the intermediate with a base to form a cis-9, trans-11 conjugated linoleic acid.Type: ApplicationFiled: December 5, 2006Publication date: February 11, 2010Inventors: Joseph C. Rongione, Jenifer Heydinger Galante, Randal J. Bernhardt
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Publication number: 20080281114Abstract: The invention concerns a method for preparing a compound of formula (I), wherein: R3 and R1 represent in particular H and n is greater than 4, said preparation method including performing a Wittig-Horner reaction with a phosphonate on a lactol, so as to obtain a hydroxyester and, optionally a saponification reaction of said hydroxyester.Type: ApplicationFiled: October 10, 2006Publication date: November 13, 2008Applicant: Pierre Fabre Dermo-CosmetiqueInventors: Natacha Frison, Benoit Folleas, Jean-Louis Brayer
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Patent number: 7399879Abstract: A process for the preparation of a monoalkylidene substituted 1,4-dions derivatives of formula (Ia) or (Ib) or a mixture of (Ia) and (Ib): wherein: R1, R2 and R3, equal to or different from each other, are hydrogen atoms or C1–C20 hydrocarbon groups: T1 and T2, equal to or different from each other, are OR4, R4, NR42, SR4 or PR42; or T1 and T2 can be fused in an oxygen atom or a NR4 group; said process comprises the step of reacting a compound of formula (II) with a compound of formula (IIIa) or (IIIb) in the presence of at least one equivalent with respect to the compound of formula (IIIa) or (IIIb) of a carbonate of metal M or of a compound of formula MTj such as K2CO3 or KHCO3Type: GrantFiled: July 25, 2003Date of Patent: July 15, 2008Assignee: Basell Poliolefine Italia S.p.A.Inventors: Yuri V. Gulevich, Giampiero Morini
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Patent number: 7253296Abstract: The invention relates to novel acylated aminopropanediols and the nitrogen and sulfur analogues thereof, pharmaceutical compositions comprising same, therapeutic uses thereof, in particular for the treatment of cerebral ischemia. The invention also provides a method of preparing said derivatives.Type: GrantFiled: February 12, 2004Date of Patent: August 7, 2007Assignee: GenfitInventors: Raphaël Darteil, Karine Caumont-Bertrand, Jamila Najib
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Publication number: 20040242690Abstract: A method for preparing a polyprenyl compound wherein an aldehyde represented by the following general formula [I]: 1Type: ApplicationFiled: April 16, 2004Publication date: December 2, 2004Applicant: NIKKEN CHEMICALS CO., LTD.Inventors: Shin Tanikawa, Mao Yamashita
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Publication number: 20030181743Abstract: A process for the preparation of alkylidene substituted succinates comprising a step (a) in which is carried out the reaction of a carbonilic compound, a succinic and a base in a reaction medium and a step (b) in which the alkylidene substituted product obtained in (a) is esterified, characterized in that the succinic ester is used in a molar amount substantially equal to, or lower than, the amount of compound carbonilic compound, (ii) the base is used in a molar amount substantially equal to the succinic ester and is selected from metal hydrides and metal and alkoxides, and (iii) the reaction medium comprises an aprotic liquid medium or a protic liquid medium having a Ka, measured in water, lower than that of iPrOH.Type: ApplicationFiled: February 5, 2003Publication date: September 25, 2003Inventors: Giampiero Morini, Yuri Gulevich, Marco Fachini, Giansiro Prini, Antonio Cristofori
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Patent number: 6610868Abstract: Novel compositions containing conjugated linoleic acids are efficacious as animal feed additives and human dietary supplements. Linoleic acid is converted to its conjugated forms in which the resulting composition is low in certain unusual isomers compared to conventional conjugated linoleic products.Type: GrantFiled: April 18, 2002Date of Patent: August 26, 2003Assignee: Natural CorporationInventors: Asgeir Saebo, Carl Skarie, Daria Jerome, Gudmunder Haroldsson
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Publication number: 20010049451Abstract: A synthesis process is disclosed for producing a conjugated fatty acid at specified temperature in high yield, including providing an ester of a fatty acid having somewhere in its carbon chain a chain of four carbon atoms such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogen atoms, and a double bond is positioned between carbon three and carbon four and reacting with a chloride selected from the group consisting of toluenesulfonyl chloride, methanesulfonyl chloride, benzenesulfonyl chloride, alkylsulfonyl chloride, and aryl-sulfonyl chloride at a temperature in the range of 10° C.-100° C., preferably 20° C.-50° C. The synthesis process provides a conjugated fatty acid formed from the ester reacted with diazabicyclo-undecene. In one aspect, the ester is formed in a pyridine solvent. In one aspect, a mesylate is formed with mesyl chloride in acetonitrile and triethyl amine.Type: ApplicationFiled: December 7, 2000Publication date: December 6, 2001Inventor: Michael C. Seidel
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Patent number: 6215009Abstract: The invention provides a process for the manufacture of a retinyl acylate of the formula I: wherein R1 is an optionally substituted C1-23-alkyl, a C2-23-alkenyl having 1 to 5 double bonds, an optionally aromatically substituted phenyl-C1-6-alkyl, or an optionally substituted phenyl. This process includes treating a compound of formula II: wherein R1 is defined above and R2 is hydrogen or COR1, with an agent that is an acid anhydride or a complex of sulfur trioxide in the presence of dimethylformamide. In addition to dimethylformamide, an aprotic organic solvent may optionally be present in the reaction. The products of the present invention are useful as intermediates for the manufacture of compounds of the vitamin A group or in certain cases as the compounds themselves.Type: GrantFiled: January 18, 2000Date of Patent: April 10, 2001Assignee: Roche Vitamins Inc.Inventors: Stefan Bischof, David Carl Burdick, Bernard Orsat
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Patent number: 6153772Abstract: A cobalt catalytic system that makes it possible to obtain branched compounds from fatty substances by reacting simple olefins on polyunsaturated esters, which may or may not be conjugated, is described.The compounds that are obtained may be hydrogenated and used as lubricant bases.Type: GrantFiled: July 24, 1998Date of Patent: November 28, 2000Assignee: Institut Francais du PetroleInventors: Gerard Hillion, Helene Olivier, Katja Siepen, Robert Stern
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Patent number: 5434281Abstract: Process for the stereospecific synthesis of leukotriene B.sub.4 (LTB.sub.4) of 6Z, 8E, 10E configuration of formula ##STR1## in which a dibenzoate triether is prepared which is subjected to a reductive elimination according to the diagram ##STR2## so as to obtain a triether which is converted in order to obtain the leukotriene B.sub.4.Type: GrantFiled: May 31, 1994Date of Patent: July 18, 1995Assignee: L'OrealInventors: Guy Solladie, Guy Stone, Antonio Urbano-Pujol, Jean Maignan
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Patent number: 5292907Abstract: The invention relates to a process for the manufacture of 6-trans-leukotriene B.sub.4 (LTB.sub.4) of formula ##STR1## in which a butadienediol is prepared; the hydroxyl groups are esterified to produce a diester and this diester is subjected to a stereospecific reductive elimination using low valency titanium [Ti(0)] to produce a 6-trans triether of formula: ##STR2## the groups --OA in positions 5 and 12 of which are then converted to --OH groups and the group --CH.sub.2 OA in position of which is then converted to a --COOH group, to produce 6-trans-LTB.sub.4.The invention also relates to intermediates obtained in the said manufacturing process.Type: GrantFiled: July 20, 1993Date of Patent: March 8, 1994Assignee: L'OrealInventors: Jean Maignan, Guy Solladie, Guy Stone
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Patent number: 5225580Abstract: A two-stage separation process for separating highly unsaturated triglycerides from an interesterification reaction product by sequential chromatographic separations wherein triglycerides are separated from saturated fatty acids in the first stage and unsaturated fatty acids are recovered in the second stage for recycle to the interesterification reaction zone. In a preferred embodiment using silica gel and silicalite in the two stages, respectively, and heptanone as desorbent in both stages, triglyceride product is removed as the first stage raffinate and the unsaturated fatty acid recycle product stream is removed as the raffinate in the second stage. In another embodiment, using silicalite adsorbent in both stages and 2-heptanone and acetone in the first and second stages, respectively, saturated fatty acids are removed as the extract in the first stage and triglycerides and unsaturated fatty acids are separated as raffinate product and extract product for recycle, respectively.Type: GrantFiled: August 16, 1990Date of Patent: July 6, 1993Assignee: UOPInventor: Hermann A. Zinnen
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Patent number: 5216023Abstract: The compounds of the Formula (I) ##STR1## wherein R.sub.1 is a C.sub.18-24 alkenyl containing at least two double bonds, or --(CH2)n --CH(NH2)m --COOHX is 0, NH or C.sub.1-4 alkyl-N,Y is CONH.sub.2, COOH or COOMe, wherein Me is hydrogen metal, andR.sub.2 is a side chain of a any amino acid except L-GLU or L-ASP at .alpha.-position or a group of Formula--(CH.sub.2).sub.k --C.sub.6 H.sub.3 --(A).sub.2 (II),--(CH.sub.2).sub.n --X--(CH.sub.2).sub.m --X--M (III)whereink is zero or an integer of 1,n is zero or an integer of 1 to 3,m is zero or an integer of 1 to 4,A is hydroxyl or one A is hydroxyl and the other A is hydrogen.M is H or R.sub.1 --CO andX and R.sub.1 are as defined aboveand their salts having tyrosine kinase inhibitor activity can be used as antitumor agents.Type: GrantFiled: September 12, 1990Date of Patent: June 1, 1993Assignee: Folligen Budapest Ltd.Inventors: Peter N. Literati, Gyorgy Keri, Maria Boross, Gabor Nemeth, Jeno Szilbereky, Ildiko Szilagyi
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Patent number: 5210227Abstract: Compounds of formula I, ##STR1## wherein R.sup.1 represents H, OH, protected OH or alkoxy; R.sup.2 represents H; R.sup.3 represents O or (H,OH); R.sup.4 represents methyl, ethyl, propyl or allyl; R.sup.5 represents OH, protected OH or alkoxy; R.sup.6 represents OH; R.sup.7 represents OH, alkoxy or NR.sup.8 R.sup.9 where R.sup.8 and R.sup.9 independently represent H, alkyl or aryl; in addition, R.sup.1 and R.sup.2 may together represent a second bond between the carbon atoms to which they are attached; and R.sup.6 and R.sup.7 may together represent O; and pharmaceutically acceptable salts thereof; are useful inter alia as immunosuppressive agents. The invention also provides the novel compounds of formula I.Type: GrantFiled: February 27, 1991Date of Patent: May 11, 1993Assignees: Fisons plc, Fujisawa Pharmaceutical Company LimitedInventors: Hirokazu Tanaka, Martin E. Cooper, David K. Donald