Oxygen Containing Hetero Ring Reactant (e.g., Succinic Anhydride, Etc.) Patents (Class 554/148)
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Patent number: 10899698Abstract: The invention provides a compound of the formula: wherein Ar is selected from the group consisting of aryl, monosubstituted aryl and polysubstituted aryl, heteroaryl, monosubstituted heteroaryl and polysubstituted heteroaryl; Ar? is selected from the group consisting of aryl, monosubstituted aryl and polysubstituted aryl, heteroaryl, monosubstituted heteroaryl and polysubstituted heteroaryl; R is an alkylene radical having 2-20 carbon atoms; and n=1-20. The compounds of the invention are used with polymer resins to enhance their gas barrier properties.Type: GrantFiled: June 9, 2011Date of Patent: January 26, 2021Assignee: ETHOX CHEMICALS, LLCInventor: James T. Tanner
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Patent number: 9957223Abstract: The invention provides a compound of the formula: wherein Ar is selected from the group consisting of aryl, monosubstituted aryl and polysubstituted aryl, heteroaryl, monosubstituted heteroaryl and polysubstituted heteroaryl; Ar? is selected from the group consisting of aryl, monosubstituted aryl and polysubstituted aryl, heteroaryl, monosubstituted heteroaryl and polysubstituted heteroaryl; R is an alkylene radical having 2-20 carbon atoms; and n=1-20. The compounds of the invention are used with polymer resins to enhance their gas barrier properties.Type: GrantFiled: August 8, 2016Date of Patent: May 1, 2018Assignee: ETHOX CHEMICALS LLCInventor: James T Tanner
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Publication number: 20150045568Abstract: A process of metathesising a feedstock in the presence of a metathesis catalyst and at least one catalyst enhancer. The catalyst enhancer can be selected from a sacrificial catalyst or a non-catalyst enhancer. The process exhibits improved reaction times and/or the metathesis catalyst can be used at very low concentrations.Type: ApplicationFiled: March 18, 2013Publication date: February 12, 2015Applicant: CRODA INTERNATIONAL PLCInventors: Bastiaan Wels, Hans Ridderikhoff, Tanja Van Bergen-Brenkman, Dessy Liminto
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Patent number: 8901329Abstract: Disclosed herein is the production of saturated alkyl esters or acids from furan materials. The starting compounds contain furan, ketone, and ester or acid functional groups and may be biologically-derived. The method includes hydrogenating the starting compound to form a reduced mixture. The method further includes hydrodeoxygenation of the reduced mixture to yield a saturated alkyl ester or acid. The saturated alkyl ester or acid can be unbranched or branched. The ester and acid products have a wide variety of applications and may be further processed into surfactants, solvents, and lubricants suitable for use in consumer products.Type: GrantFiled: September 14, 2012Date of Patent: December 2, 2014Assignee: The Procter & Gamble CompanyInventors: Ryan Michael West, Scott Leroy Cron, Jane Ellen Godlewski
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Publication number: 20140309322Abstract: The present invention relates to the process for production of a polyol from palm oil and of rigid polyurethane foams prepared from said polyol derived from palm oil. On the one hand, this invention provides a method for obtaining monomeric polyols from palm oil that have hydroxyl number between 50 450 mgKOH/g sample. The polyols of the present application may be obtained by means of a procedure based on the following four mother routes: Route 1: maleinisation of the fatty acids of palm oil; Route 2: glycerolysis of palm oil; Route 3: trancesterification of palm oil; and Route 4: epoxidation of unsaturated carbon-carbon links of palm oil. Additionally, other modalities of the invention permit obtaining polyols from the combination of these mother routes. In other realizations of the invention polyurethanes are prepared from polyols obtained through any of the four routes or by combinations of the same.Type: ApplicationFiled: October 3, 2012Publication date: October 16, 2014Inventors: Margarita María Baena Restrepo, Dency Viviana Agudelo Velásquez, Dahiana Toro Álvarez
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Patent number: 8829216Abstract: Provided herein are poly-capped estolides, including those of the Formula IV in which n is an integer equal to or greater than 0; m is an integer equal to or greater than 2; R1 is selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; R2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R3 and R4, independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched. Hydroxy estolides are also described herein, which may be suitable end products, or serve as intermediates to provide poly-capped estolides. Also provided are compositions containing poly-capped estolides and methods of making both said poly-capped estolides and compositions thereof.Type: GrantFiled: August 31, 2012Date of Patent: September 9, 2014Assignee: Biosynthetic Technologies, LLCInventors: Jeremy Forest, Travis Thompson, Jakob Bredsguard
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Publication number: 20140242867Abstract: Lignin compositions, products produced from them or containing them, methods to produce them, spinning methods, methods to convert lignin to a conversion product and conversion products produced by the methods are described.Type: ApplicationFiled: April 4, 2012Publication date: August 28, 2014Inventors: Robert Jansen, Aharon Eyal, Noa Lapidot, Bassem Hallac, Ziv-Vladimir Belman, Shmuel Kenig
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Patent number: 8710252Abstract: The present invention relates to enantiomeric forms of hepoxilin analogs of Formula I-VIII, pharmaceutical compositions thereof, a method for the separation of said enantiomeric forms of hepoxilin analogs comprising applying said hepoxilin to a chiral phase HPLC column and eluting said hepoxilin with an alkane and alcohol solvent mixture. Said enantiomeric forms of hepoxilin analogs of Formula I-VIII were found to be useful in controlling the biological effects of PPAR mediated transcriptional control for the treatment of diseases such as cancer, thromboxane-mediated diseases and for modulating intracellular calcium concentration.Type: GrantFiled: April 19, 2007Date of Patent: April 29, 2014Inventors: Cecil Pace-Asciak, Alexandra SantAna Sorensen, Jean-Philippe Meyer, Peter Denim
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Patent number: 8686169Abstract: The present disclosure relates to methods of preparation of compounds resulting from the reaction of levulinic esters and epoxidized unsaturated fatty acid esters. The compounds are useful as renewable biomass-based plasticizers for a variety of polymers. Mono-, di- and tri-ketal adducts formed in a reaction between alkyl esters of levulinate and epoxidized unsaturated fatty acid esters derived from vegetable oils are also disclosed.Type: GrantFiled: April 8, 2013Date of Patent: April 1, 2014Assignee: Segetis, Inc.Inventor: Sergey Selifonov
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Publication number: 20130237717Abstract: A method and system for producing dispersed waxes, including a high shear mechanical device. In one embodiment, the method comprises forming a dispersion of wax globules in a carrier liquid in a high shear device prior to implementation in a waxy product. In another instance the system for producing waxy products comprises a high shear device for dispersing wax in a carrier liquid.Type: ApplicationFiled: April 24, 2013Publication date: September 12, 2013Applicant: H R D CorporationInventors: Abbas HASSAN, Aziz Hassan, Gregory G. Borsinger
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Patent number: 8436042Abstract: The present disclosure relates to methods of preparation of compounds resulting from the reaction of levulinic esters and epoxidized unsaturated fatty acid esters. The compounds are useful as renewable biomass-based plasticizers for a variety of polymers. Mono-, di- and tri-ketal adducts formed in a reaction between alkyl esters of levulinate and epoxidized unsaturated fatty acid esters derived from vegetable oils are also disclosed.Type: GrantFiled: November 22, 2006Date of Patent: May 7, 2013Assignee: Segetis, Inc.Inventor: Sergey Selifonov
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Publication number: 20130066089Abstract: Disclosed herein is the production of saturated alkyl esters or acids from furan materials. The starting compounds contain furan, ketone, and ester or acid functional groups and may be biologically-derived. The method includes hydrogenating the starting compound to form a reduced mixture. The method further includes hydrodeoxygenation of the reduced mixture to yield a saturated alkyl ester or acid. The saturated alkyl ester or acid can be unbranched or branched. The ester and acid products have a wide variety of applications and may be further processed into surfactants, solvents, and lubricants suitable for use in consumer products.Type: ApplicationFiled: September 14, 2012Publication date: March 14, 2013Inventors: Ryan Michael West, Scott Leroy Cron, Jane Ellen Godlewski
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Patent number: 8357643Abstract: A lubricant from plant and/or animal oils and fats; methods for producing a lubricating oil, and the oil produced thereby. The lubricant is derived from an animal or plant fat or oil having an iodine number above about 7, and produced by epoxi-dising the fat or oil and (1) reacting the epoxidised fat or oil with a carboxylic acid anhydride in the presence of a basic catalyst to produce a diester, or (2) hydrogenating the epoxidised fat or oil to generate mono-alcohols and acylating the alcohol functionality with acid anhydrides, acid chlorides or carboxylic acids to produce a mono-ester.Type: GrantFiled: August 10, 2005Date of Patent: January 22, 2013Assignee: Battelle Memorial InstituteInventors: Herman Benecke, Bhima R. Vijayendran, Jeffrey Cafmeyer
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Patent number: 8334397Abstract: A process for producing a polyoxyethylene sorbitan fatty acid ester in which the bitterness just after the production and the bitterness with the lapse of time is suppressed. The process of the invention includes reacting an ester (component A) of a fatty acid having 10 to 22 carbon atoms and a monohydric alcohol having 1 to 3 carbon atoms with at least either (component B) of sorbitol and sorbitan to form a sorbitan fatty acid ester and adding ethylene oxide to the sorbitan fatty acid ester, thereby producing a polyoxyethylene sorbitan fatty acid ester, which is characterized that the following steps (a) to (d) are contained: (a) the component B is provided in the form of a 50 to 90% by weight aqueous solution and mixed with the component A and dehydration was performed until a water content in the system reaches 1.0% by weight or less based on the total weight of the components A and B; (b) 1 to 10% by weight of a monohydric alcohol having 1 to 3 carbon atoms and 0.1 to 1.Type: GrantFiled: January 28, 2009Date of Patent: December 18, 2012Assignee: NOF CorporationInventors: Kazuaki Wakita, Susumu Tanaka, Keiichi Maruyama
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Publication number: 20120277338Abstract: A method of improving the mechanical strength of polyurethane foams made from bio-based polyols, the polyol-containing compositions utilized in the method of the invention, and the polyurethane foams produced by the method of the invention are provided. The method of the invention involves the incorporation of aromatic polyester polyol in the polyol-containing composition used to manufacture the foams. In one embodiment, the aromatic polyester polyol is utilized in a polyol-containing composition which is employed in the manufacture of flexible polyurethane foam. In another embodiment, the aromatic polyester polyol transesterified with a natural oil-containing composition to form a transesterification reaction product that is utilized in a polyol-containing composition which is employed in the manufacture of flexible polyurethane foam.Type: ApplicationFiled: November 4, 2010Publication date: November 1, 2012Inventors: Warren A. Kaplan, Xiuguang A. Guo, David J. Norberg
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Patent number: 8283482Abstract: To provide a method for performing a cross-coupling reaction of a Grignard compound with an alkyl halide simply, efficiently and in high yield, a method for obtaining a ?-bromo long chain carboxylic acid simply and efficiently using an easily obtainable raw material and a method for producing a useful branched fatty acid simply and efficiently [R1: an alkyl group having 1 to 15 carbon atoms, R2: an alkyl group having 1 to 30 carbon atoms with a carboxyl group and X and X?: a halogen atom] [n: an integer of 9 to 17] [n: an integer of 9 to 17, R1a: a branched alkyl group having 3 to 8 carbon atoms and X: a halogen atom].Type: GrantFiled: February 8, 2008Date of Patent: October 9, 2012Assignee: Kao CorporationInventors: Taketoshi Fujimori, Mio Ishita, Yoshinori Nishizawa
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Publication number: 20120065260Abstract: Compounds of formula (I); wherein R1 and R2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl DHA, alpha-methyl DHA methyl ester, alpha-methyl DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed.Type: ApplicationFiled: September 6, 2011Publication date: March 15, 2012Inventors: Morten Bryhn, Jan Kopecky, Anne Kristin Holmeide
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Patent number: 8097740Abstract: The present invention is generally directed to the synthesis and/or manufacture of ester-based lubricant compositions. The present invention is also directed to methods of making these and other similar lubricant compositions, and to systems for implementing such methods (processes). In some embodiments, the methods for making such ester-based lubricants utilize a biomass precursor (e.g., triglyceride-bearing vegetable oils) such that the lubricant compositions generated by the methods and systems of the present invention can be properly deemed biolubricants. In these or other embodiments, lubricant precursor species can also be sourced or derived from Fischer-Tropsch (FT) and/or long-chain paraffin pyrolysis reaction products. The ester component of the lubricant compositions, produced in accordance with the methods and systems of the present invention, comprises largely diester species.Type: GrantFiled: May 19, 2008Date of Patent: January 17, 2012Assignee: Chevron U.S.A. Inc.Inventor: Stephen Joseph Miller
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Publication number: 20110313090Abstract: An improved method for producing di-isotridecylphthalate (DTDP) is disclosed by esterification using a tetra-alkyl titanate catalyst made from preferably primary alcohols having at least 4 and preferably up to but not more than 10 carbon atoms. In the esterification process, compared to using tetra-isopropyl titanate catalyst, less of the alcohol from the catalyst contributes to the environmental burden associated with discarding the waste water byproduct, and more is incorporated into the prime DTDP product.Type: ApplicationFiled: November 16, 2009Publication date: December 22, 2011Inventors: Nicolaas A. De Munck, Raphael F. Caers, Didier Naert
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Publication number: 20100311996Abstract: An object of the present invention is to provide a process for producing a polyoxyethylene sorbitan fatty acid ester in which the bitterness just after the production is suppressed and also an increase in the bitterness with the lapse of time is suppressed. The process for producing a polyoxyethylene sorbitan fatty acid ester of the invention includes reacting an ester (component A) of a fatty acid having 10 to 22 carbon atoms and a monohydric alcohol having 1 to 3 carbon atoms with at least either (component B) of sorbitol and sorbitan to form a sorbitan fatty acid ester and adding ethylene oxide to the sorbitan fatty acid ester, thereby producing a polyoxyethylene sorbitan fatty acid ester, which is characterized that the following steps (a) to (d) are contained: (a) the component B is provided in the form of a 50 to 90% by weight aqueous solution and mixed with the component A and dehydration was performed until a water content in the system reaches 1.Type: ApplicationFiled: January 28, 2009Publication date: December 9, 2010Applicant: NOF CORPORATIONInventors: Kazuaki Wakita, Susumu Tanaka, Keiichi Maruyama
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Publication number: 20100275507Abstract: Liquid suspensions are disclosed comprising a suspending medium, small particles of biomass, and small particles of an inorganic material. The inorganic material stabilizes the suspension, so that it may be transported by pipeline or tank car without developing a sediment. The suspension may be used in manufacturing a bio-fuel.Type: ApplicationFiled: August 15, 2007Publication date: November 4, 2010Applicant: BIOECON INTERNATIONAL HOLDING N.V.Inventors: Paul O'Connor, Sjoerd Daamen
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Publication number: 20100048929Abstract: To provide a method for performing a cross-coupling reaction of a Grignard compound with an alkyl halide simply, efficiently and in high yield, a method for obtaining a ?-bromo long chaincarboxylic acid simply and efficiently using an easily obtainable raw material and a method for producing a useful branched fatty acid simply and efficiently.Type: ApplicationFiled: February 8, 2008Publication date: February 25, 2010Applicant: KAO CORPORATIONInventors: Taketoshi Fujimori, Mio Ishita, Yoshinori Nishizawa
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Patent number: 7592297Abstract: The present disclosure is directed to compounds and methods of making the compounds (3, 5) having the formula: where X is a functional group chosen from: and wherein R is chosen from hydrogen, n-alkyl, iso-alkyl, aryl, heterocyclic ring, and nitrogen or a sulfur containing group, and n ranges from 0 to 4.Type: GrantFiled: October 31, 2006Date of Patent: September 22, 2009Assignee: Caterpillar Inc.Inventor: Atanu Adhvaryu
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Publication number: 20080119663Abstract: A fatty acid alkyl ester of the general formula I: and acrolein are prepared by reacting a triglyceride of the general formula II: wherein a) the triglyceride is reacted using an alcohol R?—OH in the presence of a catalyst to give said fatty acid alkyl ester and glycerol; and b) the glycerol is dehydrated catalytically to acrolein, wherein R is R1, R2 and R3, and R1, R2 and R3 are all the same or some are the same or all are different and are each a straight-chain or branched, and optionally mono- or polyunsaturated C10-C30-alkyl radical, and R? is a C1-C10-alkyl radical or a C3-C6-cycloalkyl radical.Type: ApplicationFiled: November 20, 2007Publication date: May 22, 2008Applicant: EVONIK DEGUSSA GmbHInventors: Hubert Redlingshoefer, Christoph Weckbecker, Klaus Huthmacher
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Patent number: 6927299Abstract: Disclosed are a fatty acid esters composition of a polyglycerine containing more than 70% of a fatty acid monoester which is defined by a specified analysis method, a process for the preparation thereof, a process for the preparation of a highly purified fatty esters composition of a polyglycerine, and a highly-purified fatty acid esters composition of a polyglycerine having an oxirane oxygen concentration of below 100 ppm which is defined by a specified analysis method. The fatty acid esters compositions of a polyglycerine are useful as additives for a variety of food-stuffs, additives for a variety of thermoplastic resins, and as additives for a variety of cosmetics or detergents.Type: GrantFiled: July 15, 2003Date of Patent: August 9, 2005Assignee: Daicel Chemical Industries, Ltd.Inventor: Toshio Endo
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Publication number: 20030158433Abstract: A process for the hydrogenation of a polyunsaturated oil, wherein said oil is reacted with hydrogen in the presence of a copper-chromium containing catalyst at a temperature of from about 200 to 300° C. and a pressure of from about 300 to 500 psig, for 3-8 hours. The reaction results in a product having a monounsaturated fatty acid percent conversion (i.e., monounsaturated fatty acid content) of from about 60-90%, preferably from about 70-90% and most preferably, from about 80-90%. The copper-chromium catalyst may also be recovered and reused without regeneration or further treatment prior to reuse.Type: ApplicationFiled: December 18, 2002Publication date: August 21, 2003Applicant: Archer-Daniels-Midland CompanyInventor: Ronald Sleeter
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Patent number: 6583302Abstract: Triglyceride oils having unsaturated fatty acid substituents are modified to convert sites of unsaturation to C-2 to C-10 diesters. The resulting derivatives are characterized by thermal and oxidative stability, have low temperature performance properties and are environmentally-friendly. They have utility as hydraulic fluids, lubricants, metal working fluids and other industrial fluids. The triglyceride oils are most easily prepared via epoxidized vegetable oils which are converted to the diesters in either a one- or two-step reaction.Type: GrantFiled: January 25, 2002Date of Patent: June 24, 2003Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Sevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu
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Patent number: 6528668Abstract: Methods for making 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide and derivatives thereof, esters of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid and derivatives thereof, which are useful as a variety of synthetic raw materials and intermediates, and are prepared as intermediates in the production step of &ohgr;-hydroxyaliphatic acid being important intermediates of large cyclic lactone-based perfumes in the perfume industry.Type: GrantFiled: January 14, 2002Date of Patent: March 4, 2003Assignee: Toray Industries, Inc.Inventors: Hideaki Takaoka, Sigeru Wada, Nobuhiko Ito, Akio Hasebe, Shinzo Imamura, Hideo Muraoka
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Patent number: 6225485Abstract: What is shown is a high purity adduct of castor oil and a cyclic carboxylic acid anhydride, charactered by the absence of free acid anhydride, which is used in personal care products. The adduct is made by a process, without side reactions, which includes (a) reacting castor oil and cyclic carboxylic acid anhydride at a temperature of 75-120° C. for 4 to 24 hours, and then (b) continuing the reaction at room temperature for at least 1 week to react any remaining maleic anhydride. Skin and hair care formulations of such adducts are also described.Type: GrantFiled: June 29, 1999Date of Patent: May 1, 2001Assignee: ISP Investments Inc.Inventors: Steven H. Bertz, Frank M. Miksza, Elliott Zucker
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Patent number: 6150543Abstract: The invention relates to a process for the enzymatic preparation of regioselective fatty acid esters of ascorbic acid and selected fatty acid alkyl esters.Ascorbic acid and fatty acid alkyl esters are reacted in a solvent or suspending agent at reduced pressure in relation to the atmosphere and temperatures above the boiling point of the resulting alcohol of reaction.Type: GrantFiled: December 14, 1998Date of Patent: November 21, 2000Assignee: Th. Goldschmidt AgInventors: Burghard Gruning, Geoffrey Hills
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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: 6008391Abstract: A process for making alkoxylated fatty acid alkyl esters involving: (a) providing a fatty acid alkyl ester; (b) providing an alkylene oxide component; (c) providing a catalyst component containing a mixture of: (i) a primary catalyst; and (ii) an alkylene glycol having from 2 to 6 carbon atoms; and (d) reacting (a)-(c) to make the alkoxylated fatty acid alkyl ester.Type: GrantFiled: September 25, 1998Date of Patent: December 28, 1999Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Rafael Pi Subirana, Joaquim Llosas Bigorra
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Patent number: 6008392Abstract: A process for making alkoxylated fatty acid alkyl esters involving: (a) providing a fatty acid alkyl ester; (b) providing an alkylene oxide component; (c) providing a primary catalyst; (d) providing a co-catalyst selected from the group consisting of lithium hydroxide, an alkaline earth metal, a tin salt and mixtures thereof; and (e) reacting (a)-(d) to make the alkoxylated fatty acid alkyl ester.Type: GrantFiled: September 28, 1998Date of Patent: December 28, 1999Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Ansgar Behler, Almud Folge
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Patent number: 6002030Abstract: A process is provided for the fatty acid esterification of propoxylated glycerin wherein fatty acids stripped from the esterifier and/or fatty acids stripped from the esterification product are scrubbed by contact with a scrubbing liquid which is maintained at a temperature above the fatty acid melting point.Type: GrantFiled: May 8, 1998Date of Patent: December 14, 1999Assignee: ARCO Chemical Technology, L.P.Inventor: Jon R. Valbert
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Patent number: 5872149Abstract: The present invention relates to monomeric, oligomeric and polymeric bisesters of alkyl- or alkenyldicarboxylic acid derivatives and polyalcohols, and their use as solubilizers, emulsifiers and/or detergents. In particular, the bisesters are advantageously used in cosmetic compositions, detergents and cleaners, pharmaceutical compositions, foodstuffs and crop protection compositions. The invention furthermore relates to a process for preparing these bisesters.Type: GrantFiled: August 15, 1997Date of Patent: February 16, 1999Assignee: BASF AktiengesellschaftInventors: Gabriele Dralle-Voss, Gunter Oetter, Hans-Ulrich Wekel, Knut Oppenlander
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Patent number: 5849935Abstract: An improved process for the production of high yields of .delta.-lactones and 5-hydroxy fatty acids from unsaturated fatty acids which are free or esterified with glycerol is disclosed. The .delta.-lactones may be produced by reacting one or more .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids in the presence of an acid, clay or zeolite catalyst. Alternatively, the .delta.-lactones may be produced by reacting one or more triglycerides which are esters of glycerol with .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids with the same catalysts. Because the .delta.-lactones may be produced from the triglycerides of unsaturated fatty acids, the process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification. Optionally, the .delta.-lactones so formed may be further reacted with an alkali in an aqueous solution to produce 5-hydroxy fatty acids.Type: GrantFiled: September 27, 1995Date of Patent: December 15, 1998Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Terry A. Isbell, Beth A. Plattner, Robert Kleiman
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Patent number: 5808106Abstract: 2-(.omega.-alkoxycarbonyl alkanoyl)-4-butanolide can be produced unexpectedly with a high selectivity and yield through condensation reaction of .gamma.-butyrolactone with a highly available, lo.omega.-price dicarboxylate as represented by the following general formula:ROOC(CH2)nCOOR(where n denotes an integer of 7-13, and R denotes an alkyl group or an alkenyl group). Furthermore, a long-chain .omega.-hydroxycarboxylic acid can be produced by subjecting 2-(.omega.-alkoxycarbonyl alkanoyl)-4-butanolide to hydrolysis and decarboxylation and reducing the carbonyl groups in the resultant product into methylene groups.Type: GrantFiled: April 30, 1997Date of Patent: September 15, 1998Inventors: Tetsuya Katou, Go Hata, Takeaki Etoh, Nobuhiko Ito
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Patent number: 5571936Abstract: Intermediate compounds represented as formula (I) useful for the synthesis of 16-phenoxy-prostatrienoic acid derivatives and a preparing method thereof are disclosed. ##STR1## wherein R is tetrahydropyranyl, tetrahydrofuranyl, 2-ethoxyethyl, 3-t-butyldimethylsilyl triisopropylsilyl or triethylsilyl group; R.sup.1 and R.sup.2 are independently hydrogen or ester-forming group; P is hydrogen, trimethylsilyl or tri-n-butyltin; and wavy line means epistereoisomeric mixture.Type: GrantFiled: September 30, 1994Date of Patent: November 5, 1996Assignee: Korea Institute of Science and TechnologyInventors: Hokoon Park, Sun Ho Jung, Yong Sup Lee, Ki Hong Nam
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Patent number: 5508048Abstract: High erucic cruciferae oils are interesterified with C.sub.16 or higher fatty acids or derivatives thereof. The use of a 1,3-selective lipase leads to the introduction of the fatty acid groups in the 1,3-positions. The liberated erucic acid (derivative) can be hydrogenated; the behenyl acid (or derivative) thus formed can be recirculated to provide at least 50% of the behenyl acid (derivative) needed in the process. The products obtainable by these processes, display good anti-blooming properties.Type: GrantFiled: January 7, 1994Date of Patent: April 16, 1996Assignee: Van Den Bergh Foods Co.Inventor: Frederick B. Padley
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Patent number: 5466843Abstract: Esterified alkoxylated polyols containing long chain saturated linear acyl groups are obtained by esterification of an alkoxylated polyol such as propoxylated glycerin with a C.sub.12 -C.sub.24 fatty acid such as behenic acid and recovery of excess fatty acid by treatment with an aliphatic hydrocarbon. Esterified alkoxylated polyols prepared in this manner are useful fat substitutes for the formulation of reduced calorie food products.Type: GrantFiled: April 29, 1994Date of Patent: November 14, 1995Assignee: ARCO Chemical Technology, L.P.Inventor: Charles F. Cooper
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Patent number: 5399728Abstract: A convenient method of obtaining useful highly esterified alkoxylated polyol fat substitutes from readily available triglycerides such as fats and oils is provided.Type: GrantFiled: April 5, 1993Date of Patent: March 21, 1995Assignees: ARCO Chemical Technology, L.P., CPC International Inc.Inventor: Charles F. Cooper
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Liquid or flowable derivatives of natural fats and oils a process for their production and their use
Patent number: 5391784Abstract: The present invention relates to derivatives of natural fats and oils that are liquid or flowable, respectively, and to a process for the production of said derivatives, in which oxalkylation is carried out at elevated temperatures in the presence of basic catalysts with at least one compound containing an epoxide group, and sulfation is carried out in a manner known per se, in which a starting material containingA) at least one C.sub.8 -C.sub.24 -fatty acid ester of an aliphatic C.sub.1 -C.sub.5 -monoalcoholThe present invention furthermore relates to the use of said derivatives, optionally in combination with other greasing substances and anionic and/or non-ionic emulsifiers, for the fatliquoring and greasing of leather.Type: GrantFiled: December 6, 1993Date of Patent: February 21, 1995Assignee: Chemische Fabrik Stockhausen GmbHInventors: Helmut Brehn, Helmut Klimmek, Leonhard Strijbos -
Patent number: 5380912Abstract: .omega.-Hydroxy-(.omega.-3)-ketonitrile of the formula NC(CH.sub.2).sub.n --CO--(CH.sub.2).sub.3 OH wherein n is an integer of 7 to 11.Type: GrantFiled: March 31, 1994Date of Patent: January 10, 1995Assignees: Ube Industries, Ltd., Soda Aromatic Co., Ltd.Inventors: Hiroshi Yoshida, Noboru Kakeya, Masanori Kashiwagi
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Patent number: 5350868Abstract: There are disclosed (i) .omega.-hydroxy-(.omega.-3)-ketonitrile represented by the formula ( I ):NC(CH.sub.2).sub.n --CO--(CH.sub.2).sub.3 OH (I)wherein n is an integer of 7 to 11, (ii) a method for preparing the .omega.-hydroxy-(.omega.-3)-ketonitrile which comprises reacting .alpha.-(.omega.-cyanoalkanoyl)-.gamma.-butyrolactone represented by the formula (II): ##STR1## wherein n has the same meaning as defined above, in the presence of 1 to less than 2 mole of an alkali metal hydroxide per mole of the butyrolactone in an aqueous medium, and (iii) a method for preparing .omega.-hydroxy fatty acid represented by the formula (IV):HOOC(CH.sub.2).sub.n+4 --OH (IV)wherein n has the same meaning as defined above, which comprises reacting the above .omega.-hydroxy-(.omega.-3)-ketonitrile of the formula (I) with hydrazine in an aqueous solution of an alkali metal hydroxide.Type: GrantFiled: February 19, 1993Date of Patent: September 27, 1994Assignees: Ube Industries, Ltd., Soda Aromatic Co., Ltd.Inventors: Hiroshi Yoshida, Noboru Kakeya, Masanori Kashiwagi
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Patent number: 5334736Abstract: A method to functionalize carbohydrate derivatives by base-induced .beta.-elimination and subsequent olefination to form biologically active products containing .alpha.-hydroxy-diene or .alpha.,.beta.-dihydroxy-diene subunits. Also disclosed are methods to prepare biologically active derivatives of fatty acids containing .alpha.-hydroxy-diene groups and .alpha.,.beta.-dihydroxy-diene groups from derivatives of 2-deoxyfuranoses and derivatives of 2-deoxypyranoses, respectively.Type: GrantFiled: May 16, 1991Date of Patent: August 2, 1994Assignee: University of Texas System Board of RegentsInventors: Lumin Sun, John R. Falck
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Patent number: 5304665Abstract: A convenient method of obtaining useful highly esterified alkoxylated polyol fat substitutes from readily available triglycerides such as fats and oils is provided.Type: GrantFiled: April 5, 1993Date of Patent: April 19, 1994Assignees: Arco Chemical Technology, L.P., CPC International, Inc.Inventors: Charles F. Cooper, Bernard C. Sekula, Stephen D. Harper
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Patent number: 5292910Abstract: A process for the catalyzed ethoxylation or propoxylation of compounds selected from the group consisting of organic compounds containing active H atoms, esters of fatty acids containing 2 to 22 carbon atoms with monoalkanols containing 1-22 carbon atoms with polyols containing 2 to 12 carbon atoms and 2 to 6 hydroxyl groups, wherein the improvement comprises the use as catalyst for the ethoxylation or propoxylation of hydrophobicized hydrotalcites corresponding to the general formula I:Mg.sub.x Al(OH).sub.y (CO.sub.3).sub.m (A).sub.n.zH.sub.2 O (I),in which A is selected from the group consisting of (i) a dianion of an aliphatic dicarboxylic acid containing 4 to 44 carbon atoms and (ii) two anions of aliphatic monocarboxylic acids containing 2 to 34 carbon atoms; 1<x<5; y.ltoreq.2x+2; {y+2(m+n)}=2x+3; m+n.ltoreq.0.5; m.gtoreq.0; and 0<z<10.Type: GrantFiled: December 2, 1992Date of Patent: March 8, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Hans-Christian Raths, Wolfgang Breuer, Klaus Friedrich, Klaus Herrmann
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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: RE42313Abstract: Triglyceride oils having unsaturated fatty acid substituents are modified to convert sites of unsaturation to C-2 to C-10 diesters. The resulting derivatives are characterized by thermal and oxidative stability, have low temperature performance properties and are environmentally-friendly. They have utility as hydraulic fluids, lubricants, metal working fluids and other industrial fluids. The triglyceride oils are most easily prepared via epoxidized vegetable oils which are converted to the diesters in either a one- or two-step reaction.Type: GrantFiled: June 7, 2005Date of Patent: April 26, 2011Assignees: The United States of America as repesented by the Secretary of Agriculture, The Penn State Research FoundationInventors: Sevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu