Oxygen Containing Hetero Ring Reactant (e.g., Succinic Anhydride, Etc.) Patents (Class 554/148)
  • Patent number: 10899698
    Abstract: 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: Grant
    Filed: June 9, 2011
    Date of Patent: January 26, 2021
    Assignee: ETHOX CHEMICALS, LLC
    Inventor: James T. Tanner
  • Patent number: 9957223
    Abstract: 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: Grant
    Filed: August 8, 2016
    Date of Patent: May 1, 2018
    Assignee: ETHOX CHEMICALS LLC
    Inventor: James T Tanner
  • Publication number: 20150045568
    Abstract: 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: Application
    Filed: March 18, 2013
    Publication date: February 12, 2015
    Applicant: CRODA INTERNATIONAL PLC
    Inventors: Bastiaan Wels, Hans Ridderikhoff, Tanja Van Bergen-Brenkman, Dessy Liminto
  • Patent number: 8901329
    Abstract: 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: Grant
    Filed: September 14, 2012
    Date of Patent: December 2, 2014
    Assignee: The Procter & Gamble Company
    Inventors: Ryan Michael West, Scott Leroy Cron, Jane Ellen Godlewski
  • Publication number: 20140309322
    Abstract: 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: Application
    Filed: October 3, 2012
    Publication date: October 16, 2014
    Inventors: Margarita María Baena Restrepo, Dency Viviana Agudelo Velásquez, Dahiana Toro Álvarez
  • Patent number: 8829216
    Abstract: 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: Grant
    Filed: August 31, 2012
    Date of Patent: September 9, 2014
    Assignee: Biosynthetic Technologies, LLC
    Inventors: Jeremy Forest, Travis Thompson, Jakob Bredsguard
  • Publication number: 20140242867
    Abstract: 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: Application
    Filed: April 4, 2012
    Publication date: August 28, 2014
    Inventors: Robert Jansen, Aharon Eyal, Noa Lapidot, Bassem Hallac, Ziv-Vladimir Belman, Shmuel Kenig
  • Patent number: 8710252
    Abstract: 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: Grant
    Filed: April 19, 2007
    Date of Patent: April 29, 2014
    Inventors: Cecil Pace-Asciak, Alexandra SantAna Sorensen, Jean-Philippe Meyer, Peter Denim
  • Patent number: 8686169
    Abstract: 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: Grant
    Filed: April 8, 2013
    Date of Patent: April 1, 2014
    Assignee: Segetis, Inc.
    Inventor: Sergey Selifonov
  • Publication number: 20130237717
    Abstract: 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: Application
    Filed: April 24, 2013
    Publication date: September 12, 2013
    Applicant: H R D Corporation
    Inventors: Abbas HASSAN, Aziz Hassan, Gregory G. Borsinger
  • Patent number: 8436042
    Abstract: 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: Grant
    Filed: November 22, 2006
    Date of Patent: May 7, 2013
    Assignee: Segetis, Inc.
    Inventor: Sergey Selifonov
  • Publication number: 20130066089
    Abstract: 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: Application
    Filed: September 14, 2012
    Publication date: March 14, 2013
    Inventors: Ryan Michael West, Scott Leroy Cron, Jane Ellen Godlewski
  • Patent number: 8357643
    Abstract: 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: Grant
    Filed: August 10, 2005
    Date of Patent: January 22, 2013
    Assignee: Battelle Memorial Institute
    Inventors: Herman Benecke, Bhima R. Vijayendran, Jeffrey Cafmeyer
  • Patent number: 8334397
    Abstract: 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: Grant
    Filed: January 28, 2009
    Date of Patent: December 18, 2012
    Assignee: NOF Corporation
    Inventors: Kazuaki Wakita, Susumu Tanaka, Keiichi Maruyama
  • Publication number: 20120277338
    Abstract: 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: Application
    Filed: November 4, 2010
    Publication date: November 1, 2012
    Inventors: Warren A. Kaplan, Xiuguang A. Guo, David J. Norberg
  • Patent number: 8283482
    Abstract: 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: Grant
    Filed: February 8, 2008
    Date of Patent: October 9, 2012
    Assignee: Kao Corporation
    Inventors: Taketoshi Fujimori, Mio Ishita, Yoshinori Nishizawa
  • Publication number: 20120065260
    Abstract: 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: Application
    Filed: September 6, 2011
    Publication date: March 15, 2012
    Inventors: Morten Bryhn, Jan Kopecky, Anne Kristin Holmeide
  • Patent number: 8097740
    Abstract: 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: Grant
    Filed: May 19, 2008
    Date of Patent: January 17, 2012
    Assignee: Chevron U.S.A. Inc.
    Inventor: Stephen Joseph Miller
  • Publication number: 20110313090
    Abstract: 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: Application
    Filed: November 16, 2009
    Publication date: December 22, 2011
    Inventors: Nicolaas A. De Munck, Raphael F. Caers, Didier Naert
  • Publication number: 20100311996
    Abstract: 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: Application
    Filed: January 28, 2009
    Publication date: December 9, 2010
    Applicant: NOF CORPORATION
    Inventors: Kazuaki Wakita, Susumu Tanaka, Keiichi Maruyama
  • Publication number: 20100275507
    Abstract: 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: Application
    Filed: August 15, 2007
    Publication date: November 4, 2010
    Applicant: BIOECON INTERNATIONAL HOLDING N.V.
    Inventors: Paul O'Connor, Sjoerd Daamen
  • Publication number: 20100048929
    Abstract: 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: Application
    Filed: February 8, 2008
    Publication date: February 25, 2010
    Applicant: KAO CORPORATION
    Inventors: Taketoshi Fujimori, Mio Ishita, Yoshinori Nishizawa
  • Patent number: 7592297
    Abstract: 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: Grant
    Filed: October 31, 2006
    Date of Patent: September 22, 2009
    Assignee: Caterpillar Inc.
    Inventor: Atanu Adhvaryu
  • Publication number: 20080119663
    Abstract: 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: Application
    Filed: November 20, 2007
    Publication date: May 22, 2008
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Hubert Redlingshoefer, Christoph Weckbecker, Klaus Huthmacher
  • Patent number: 6927299
    Abstract: 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: Grant
    Filed: July 15, 2003
    Date of Patent: August 9, 2005
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Toshio Endo
  • Publication number: 20030158433
    Abstract: 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: Application
    Filed: December 18, 2002
    Publication date: August 21, 2003
    Applicant: Archer-Daniels-Midland Company
    Inventor: Ronald Sleeter
  • Patent number: 6583302
    Abstract: 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: Grant
    Filed: January 25, 2002
    Date of Patent: June 24, 2003
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Sevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu
  • Patent number: 6528668
    Abstract: 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: Grant
    Filed: January 14, 2002
    Date of Patent: March 4, 2003
    Assignee: Toray Industries, Inc.
    Inventors: Hideaki Takaoka, Sigeru Wada, Nobuhiko Ito, Akio Hasebe, Shinzo Imamura, Hideo Muraoka
  • Patent number: 6225485
    Abstract: 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: Grant
    Filed: June 29, 1999
    Date of Patent: May 1, 2001
    Assignee: ISP Investments Inc.
    Inventors: Steven H. Bertz, Frank M. Miksza, Elliott Zucker
  • Patent number: 6150543
    Abstract: 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: Grant
    Filed: December 14, 1998
    Date of Patent: November 21, 2000
    Assignee: Th. Goldschmidt Ag
    Inventors: Burghard Gruning, Geoffrey Hills
  • Patent number: 6140512
    Abstract: 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: Grant
    Filed: May 12, 1999
    Date of Patent: October 31, 2000
    Assignee: ASTA Medica Aktiengesellschaft
    Inventors: Brian Michael Adger, Raymond McCague, Stanley Michael Roberts
  • Patent number: 6124485
    Abstract: 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: Grant
    Filed: March 25, 1998
    Date of Patent: September 26, 2000
    Assignee: Abbott Laboratories
    Inventors: Xiu C. Wang, Ashok V. Bhatia, Azad Hossain, Timothy B. Towne
  • Patent number: 6008391
    Abstract: 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: Grant
    Filed: September 25, 1998
    Date of Patent: December 28, 1999
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Rafael Pi Subirana, Joaquim Llosas Bigorra
  • Patent number: 6008392
    Abstract: 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: Grant
    Filed: September 28, 1998
    Date of Patent: December 28, 1999
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Ansgar Behler, Almud Folge
  • Patent number: 6002030
    Abstract: 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: Grant
    Filed: May 8, 1998
    Date of Patent: December 14, 1999
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Jon R. Valbert
  • Patent number: 5872149
    Abstract: 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: Grant
    Filed: August 15, 1997
    Date of Patent: February 16, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Gabriele Dralle-Voss, Gunter Oetter, Hans-Ulrich Wekel, Knut Oppenlander
  • Patent number: 5849935
    Abstract: 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: Grant
    Filed: September 27, 1995
    Date of Patent: December 15, 1998
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Terry A. Isbell, Beth A. Plattner, Robert Kleiman
  • Patent number: 5808106
    Abstract: 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: Grant
    Filed: April 30, 1997
    Date of Patent: September 15, 1998
    Inventors: Tetsuya Katou, Go Hata, Takeaki Etoh, Nobuhiko Ito
  • Patent number: 5571936
    Abstract: 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: Grant
    Filed: September 30, 1994
    Date of Patent: November 5, 1996
    Assignee: Korea Institute of Science and Technology
    Inventors: Hokoon Park, Sun Ho Jung, Yong Sup Lee, Ki Hong Nam
  • Patent number: 5508048
    Abstract: 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: Grant
    Filed: January 7, 1994
    Date of Patent: April 16, 1996
    Assignee: Van Den Bergh Foods Co.
    Inventor: Frederick B. Padley
  • Patent number: 5466843
    Abstract: 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: Grant
    Filed: April 29, 1994
    Date of Patent: November 14, 1995
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Charles F. Cooper
  • Patent number: 5399728
    Abstract: A convenient method of obtaining useful highly esterified alkoxylated polyol fat substitutes from readily available triglycerides such as fats and oils is provided.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: March 21, 1995
    Assignees: ARCO Chemical Technology, L.P., CPC International Inc.
    Inventor: Charles F. Cooper
  • Patent number: 5391784
    Abstract: 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: Grant
    Filed: December 6, 1993
    Date of Patent: February 21, 1995
    Assignee: Chemische Fabrik Stockhausen GmbH
    Inventors: Helmut Brehn, Helmut Klimmek, Leonhard Strijbos
  • Patent number: 5380912
    Abstract: .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: Grant
    Filed: March 31, 1994
    Date of Patent: January 10, 1995
    Assignees: Ube Industries, Ltd., Soda Aromatic Co., Ltd.
    Inventors: Hiroshi Yoshida, Noboru Kakeya, Masanori Kashiwagi
  • Patent number: 5350868
    Abstract: 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: Grant
    Filed: February 19, 1993
    Date of Patent: September 27, 1994
    Assignees: Ube Industries, Ltd., Soda Aromatic Co., Ltd.
    Inventors: Hiroshi Yoshida, Noboru Kakeya, Masanori Kashiwagi
  • Patent number: 5334736
    Abstract: 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: Grant
    Filed: May 16, 1991
    Date of Patent: August 2, 1994
    Assignee: University of Texas System Board of Regents
    Inventors: Lumin Sun, John R. Falck
  • Patent number: 5304665
    Abstract: A convenient method of obtaining useful highly esterified alkoxylated polyol fat substitutes from readily available triglycerides such as fats and oils is provided.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: April 19, 1994
    Assignees: Arco Chemical Technology, L.P., CPC International, Inc.
    Inventors: Charles F. Cooper, Bernard C. Sekula, Stephen D. Harper
  • Patent number: 5292910
    Abstract: 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: Grant
    Filed: December 2, 1992
    Date of Patent: March 8, 1994
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hans-Christian Raths, Wolfgang Breuer, Klaus Friedrich, Klaus Herrmann
  • Patent number: 5292907
    Abstract: 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: Grant
    Filed: July 20, 1993
    Date of Patent: March 8, 1994
    Assignee: L'Oreal
    Inventors: Jean Maignan, Guy Solladie, Guy Stone
  • Patent number: RE42313
    Abstract: 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: Grant
    Filed: June 7, 2005
    Date of Patent: April 26, 2011
    Assignees: The United States of America as repesented by the Secretary of Agriculture, The Penn State Research Foundation
    Inventors: Sevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu