Another Reactant Is A Carboxylic Acid Patents (Class 554/165)
  • Patent number: 11441091
    Abstract: A grease base oil, containing: condensation esters of alcohols (A) and carboxylic acids (B), wherein the alcohols (A) include a polyhydric alcohol represented by General Formula (1), the carboxylic acids (B) include a fatty acid having 5 to 9 carbon atoms (B-1), a branched fatty acid having 15 to 20 carbon atoms (B-2), a cycloalkane monocarboxylic acid having 4 to 8 carbon atoms (B-3), and an aromatic carboxylic acid (B-4), and the carboxylic acids (B) have a percentage of (B-1) above of 30 mol % to 50 mol %, a percentage of (B-2) above of 30 mol % to 50 mol %, a percentage of (B-3) above of 10 mol % to 30 mol %, and a percentage of (B-4) above of 1 mol % to 15 mol %. The grease base oil contains condensation esters having heat resistance and low temperature storageability.
    Type: Grant
    Filed: January 30, 2020
    Date of Patent: September 13, 2022
    Assignees: KYODO YUSHI CO., LTD., KAO CORPORATION
    Inventors: Tatsuya Miyazaki, Yuta Kanazawa, Tomonobu Komoriya, Hiroyuki Ishikawa, Yuta Sato
  • Patent number: 10696850
    Abstract: The present invention comprises a crosslinkable polymer compound comprising a fluorinated Unit A, an optional hydrophilic Unit B, an optional acidic or neutralized acid Unit C, a crosslinkable pendant olefin group-containing Unit D, and an optional hydrophobic alkyl Unit E. Such polymeric compounds are useful as coatings additives such that, when the coating is applied to a substrate, the additive compound is allowed to first migrate to the surface and subsequently crosslink to form a durable oil-, dirt-, and water-repellent surface.
    Type: Grant
    Filed: April 28, 2016
    Date of Patent: June 30, 2020
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Anilkumar Raghavanpillai, James J. Hughes, Vincent Franco, John Russell Crompton, Jr., Brad M Rosen, Hau-Nan Lee, Michael Henry Ober, Dan Qing Wu
  • Patent number: 10252972
    Abstract: A method of chemically extending a carbon chain of an unsaturated fatty acid for conversion into a different unsaturated fatty acid has been reported. The present invention shortens reaction steps of conventional methods, and completes a carbon chain extending reaction in a shorter time. The present invention provides a method of extending a carbon chain of an unsaturated fatty acid by two carbons, comprising steps of four stages including a short-path conversion reaction of an unsaturated fatty chain obtained from an unsaturated fatty acid into a malonic ester derivative, and heating of the malonic ester derivative to reflux in a lower fatty acid solution. The method of the present invention can complete a carbon chain extending reaction in a shorter time.
    Type: Grant
    Filed: June 27, 2016
    Date of Patent: April 9, 2019
    Assignee: Bizen Chemical Co., Ltd.
    Inventors: Naomichi Bamba, Yoshihisa Misawa, Hiroshi Tabata, Yoshio Shimizu
  • Patent number: 10030212
    Abstract: The present invention relates to a method for preparing glyceride type polyunsaturated fatty acids. The method comprises: firstly mixing a basic catalyst with glycerol or a glyceride uniformly; then adding the mixture to a polyunsaturated fatty acid material slowly, and carrying out an esterification reaction under certain conditions to obtain glyceride type polyunsaturated fatty acids, wherein the basic catalyst is a lower aliphatic alcohol sodium/potassium or a solution thereof. The procedure of the process is simple, has mild reaction conditions, short reaction time, high yield and good quality of the obtained product.
    Type: Grant
    Filed: October 12, 2015
    Date of Patent: July 24, 2018
    Assignee: ZHEJIANG MEDICINE CO., LTD. XINCHANG PHARMACEUTICAL FACTORY
    Inventors: Xuebing Xiang, Xinde Xu, Bin Shao, Chong Li
  • Patent number: 10030211
    Abstract: This invention generally relates to the isolation of molecules exhibiting vitamin E activity, e.g. tocopherols and/or tocotrienols, from mixed lipid feedstocks. In alternative embodiments, the inventions provides methods and industrial processes for isolating vitamin E molecules, including tocopherols and/or tocotrienols, from mixed lipid feedstocks by combining the feedstock with an alcohol and reacting the mixture at or above the critical point of the alcohol, and then optionally separating the products into discreet fractions.
    Type: Grant
    Filed: August 29, 2014
    Date of Patent: July 24, 2018
    Assignee: Inventure Renewables, INC.
    Inventors: William W. Berry, William Rusty Sutterlin, Mark G. Tegen, Ryan Long
  • Patent number: 9453097
    Abstract: This invention relates to a method for preparing a polycarboxylate superplasticizer by graft copolymerization of fatty acid vinyl ester onto acrylate polymer. In this invention, a type of polycarboxylate superplasticizer by graft copolymerization of fatty acid vinyl ester onto acrylate polymer was synthesized by the processes of polymerization-grafting-alcoholysis-hydrolysis with acrylate and fatty acid vinyl ester as main reactants. In the first polymerization step, the polyacrylate was synthesized by using acrylate as monomer and a certain amount of initiator and molecular weight regulator. In the second graft copolymerization step, the graft polymer with polyacrylate as main chain and poly(fatty acid vinyl ester) as side chain was synthesized by graft copolymerization between polyacrylate and fatty acid vinyl ester. The final polycarboxylate superplasticizer product with polyacrylic acid as main chain and polyvinyl alcohol as side chain was obtained by subsequent alcoholysis and hydrolysis steps.
    Type: Grant
    Filed: August 18, 2015
    Date of Patent: September 27, 2016
    Assignee: BEIJING UNIVERSITY OF TECHNOLOGY
    Inventors: Xiao Liu, Ziming Wang, Ming Zhao, Suping Cui, Mingzhang Lan
  • Patent number: 9174922
    Abstract: The present invention relates to a continuous, catalytic process for preparing a vinyl ester of the formula R—C(O)O—CH?CH2 by reaction of a carboxylic acid of the formula R—C(O)OH with a transvinylating reagent of the formula R1—C(O)O—CH?CH2, wherein the reaction is effected at a temperature of 90 to 160° C. and at a pressure of 0.5 to 15 MPa without withdrawal of a reactant in the presence of a transition metal catalyst containing at least one transition metal from the group of ruthenium, osmium, rhodium, iridium, palladium and platinum, and then the resulting reaction mixture is separated into its constituents.
    Type: Grant
    Filed: January 18, 2013
    Date of Patent: November 3, 2015
    Assignee: OXEA GMBH
    Inventors: Leif Johnen, Heinz Strutz, Kurt Schalapski, Norman Nowotny, Wolfgang Höfs, Sebastian Geisel
  • Publication number: 20150031097
    Abstract: The present invention improves biodiesel production in several ways. Unique combinations of unit operations and flow configurations are disclosed in mobile processing units that are feedstock-flexible and can be dynamically deployed in a distributed way. In some embodiments, a process includes introducing a waste oil and an alcohol into a reactor with an esterification-transesterification enzymatic catalyst. Free fatty acids are reacted with alcohol to produce fatty acid alkyl esters, and glycerides are reacted with alcohol to produce fatty acid alkyl esters and glycerin. A membrane separator removes glycerin, water, and alcohol. Unreacted free fatty acids are then separated and recycled, to generate a product stream with fatty acid alkyl esters. A genset may be provided for combusting glycerin to produce electrical power and thermal heat as co-products. This biodiesel process may be energy self-sufficient, require no external utilities, and avoid direct discharge of wastewater.
    Type: Application
    Filed: January 30, 2013
    Publication date: January 29, 2015
    Inventors: James M. Rethore, Julie E. Wheeler, Luca Zullo
  • Patent number: 8865922
    Abstract: A method of treating tall oil pitch, which comprises sterol esters of fatty acids. According to the present invention, the esters of sterols and fatty acids are broken down, in which case especially formic acid esters or acetic acid esters of sterols are formed instead. The free fatty acids and sterol esters generated are distilled or separated in another way. Use of the present invention increases the yield of fatty acids and also facilitates the separation of sterols from tall oil pitch.
    Type: Grant
    Filed: March 28, 2011
    Date of Patent: October 21, 2014
    Assignee: Forchem Oy
    Inventors: Esko Kiviranta, Juhani Saviainen, Mikko Rintola
  • Publication number: 20130046105
    Abstract: Methods are provided for pelletizing a microbial biomass, extracting a refined lipid composition from the pelletized biomass under supercritical conditions and distilling the refined lipid composition, at least once under short path distillation conditions, to obtain a lipid-containing fraction. Also disclosed are methods of making lipid-containing oil concentrates therefrom, by transesterifying and enriching the lipid-containing fraction.
    Type: Application
    Filed: February 10, 2012
    Publication date: February 21, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Marios Avgousti, Timothy Allan Bell, Richard E. Bockrath, Oliver Walter Gutsche, Keith W. Hutchenson, Shu-Chien Liang, Robert D. Orlandi
  • Patent number: 8288573
    Abstract: The present invention provides a process for preparing a bio-diesel, comprising, in the presence of an alkaline metal compound, reacting an oil-fat with C1-C6 monohydric alcohol in a reactor at a reaction temperature of from 130 to 280° C. and a reaction pressure of from 1 to 12 MPa, separating fatty acid esters from the reacted materials, so as to produce the bio-diesel, wherein said alkaline metal compound is present in an amount of 0.001-0.07 wt %, in terms of the metal thereof, relative to the weight of the oil-fat. The process provided in the present invention has the advantages of great throughput and high yield of the bio-diesel.
    Type: Grant
    Filed: December 15, 2006
    Date of Patent: October 16, 2012
    Assignees: China Petroleum & Chemical Corporation, Research Institute of Petroleum Processing, Sinopec
    Inventors: Haijing Wang, Zexue Du, Enze Min, Guoqiang Gao
  • Publication number: 20120100073
    Abstract: Fatty acid analogue (FAA) molecules comprising positron-emitting radionuclides, salts thereof, and FAA-triglycerides are disclosed. Also disclosed are methods of synthesis, and methods of imaging distribution and metabolism of fatty acids and fatty acid triglycerides.
    Type: Application
    Filed: May 4, 2010
    Publication date: April 26, 2012
    Applicant: WASHINGTON UNIVERSITY
    Inventors: Robert H. Mach, Robert John Gropler, Zhude Tu, Pilar Herrero
  • Patent number: 8063235
    Abstract: Method for improving the performance of a preparative batchwise Super Critical Fluid Chromatographic separation for the recovery of a target fatty acid or derivative thereof, or of a group of target fatty acids or of derivatives thereof from a mixture, characterized in that the said Super Critical Fluid Chromatographic separation employs a chromatographic column charged with a stationary phase chosen from the group consisting of aluminium oxide or aluminium oxides, titanium oxide or titanium oxides, silica gel or silica gels, amino propyl modified silica gels, diol modified silica gels, phenyl modified silica gels and “reversed phase” phases, the former in turn chosen from the group consisting of RP18, RP8 and RP3, and in that the said Super Critical Fluid Chromatographic Separation further employs a mobile phase chosen from the group consisting of ethylene, propane, ammonia, dinitrogen dioxide and CO2, wherein in the said method, during the run of the said mixture on the chromatographic column, a pressure an
    Type: Grant
    Filed: June 19, 2007
    Date of Patent: November 22, 2011
    Assignee: K.D. Pharma Bexbach GmbH
    Inventors: Rudolf Krumbholz, Peter Lembke, Norbert Schirra
  • Publication number: 20110200735
    Abstract: Provided herein are oil compositions comprising an interesterified structured lipid component, the component being an interesterifcation reaction product of an amount of a medium chain triglyceride, an amount of a long chain domestic oil, and an amount of a a source of stearidonic acid. The structured lipid component can be used in edible oil compositions. The oil compositions can contain an amount of a phytosterol ester component. The oil compositions disclosed herein have good stability and also have other properties useful for an edible oil composition.
    Type: Application
    Filed: February 17, 2010
    Publication date: August 18, 2011
    Inventors: Dilip K. Nakhasi, Danielle N. Corbin, Roger L. Daniels
  • Patent number: 7754904
    Abstract: A process is described in which an unsaturated fat is reacted in a homometathesis reaction in the presence of at least one non-aqueous ionic liquid to produce both an olefinic fraction and a composition of monoalcohol diesters or diacids. Particular application to a mixture of esters of an oleic sunflower seed oil or an oleic rapeseed oil, the process producing both an olefinic fraction and a composition of monoalcohol diesters or diacids wherein, in general, more than half of its chains is constituted by unsaturated C18 chains.
    Type: Grant
    Filed: January 23, 2007
    Date of Patent: July 13, 2010
    Assignee: Institut Francais du Petrole
    Inventors: Hélène Olivier-Bourbigou, Gérard Hillion, Christophe Vallee
  • Publication number: 20090156845
    Abstract: The invention relates to acrylate modified, natural fatty acid based hybride polymers, and to a method for their preparation. The invention also relates to the use of the modified natural fatty acid based hybride polymers as binding agents especially in water based coatings, adhesives and composites and as environmentally friendly wood impregnating agents. The acrylate-modified natural fatty acid based hybride polymer is a block polymer formed of acrylate segments and fatty acid segments.
    Type: Application
    Filed: March 2, 2007
    Publication date: June 18, 2009
    Applicant: Valtion teknillinen tutkimuskesus
    Inventors: Nina Heiskanen, Pia Willberg, Salme Koskimies, Janne Hulkko, Pirita Ushanov, Sirkka-Liisa Maunu
  • Patent number: 6420322
    Abstract: A process for modifying an unsaturated triacylglycerol oil, such as an vegetable oil stock, to enhance its fluidity and/or oxidative stability is provided. Lubricants containing a modified an unsaturated triacylglycerol oil and methods for their production and use are also provided.
    Type: Grant
    Filed: April 22, 1997
    Date of Patent: July 16, 2002
    Assignee: Cargill, Incorporated
    Inventor: Dharma R. Kodali
  • Patent number: 5872268
    Abstract: A process for the preparation of a salt of fatty acid ester of hydroxycarboxylic acid, which comprises subjecting a fatty acid ester of lower alcohol and an alkaline metal salt or alkaline earth metal salt of hydroxycarboxylic acid to ester interchange in an organic solvent in the presence of a nonionic or anionic surface active agent and an alkali catalyst. The highly pure salt of fatty acid ester of hydroxycarboxylic acid obtained by the separation and purification of the reaction product exhibits a remarkably excellent surface activating ability as compared with the existing commercial products.
    Type: Grant
    Filed: December 12, 1996
    Date of Patent: February 16, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Yukio Kasori, Tetsuro Yamazaki, Keita Kashiwa
  • Patent number: 5750751
    Abstract: Glycol co-esters of drying-oil fatty acids and polymerizable unsaturated carboxylic acids are formed by a novel bi-phase catalysis in liquid-liquid or liquid-solid dispersions. The co-esters form directly from drying-oil acids and partial glycol esters of vinylic carboxylic acids, or vice versa. Complete removal of the by-produced water by distillation is unnecessary and the commonly encountered side reactions of direct esterification are suppressed since reaction temperatures can be as low as ambient. The expensive acid chlorides or anhydrides combined with acid acceptors, previously used to prepare such co-esters, are circumvented along with the by-produced hydrochlorides or carboxylates which must be recovered and disposed in an environmentally acceptable way. The co-esters formed here are useful in free radical copolymerizations that provide novel film-forming polymers capable of cross-linig when dried in air. They can be formed in bulk, solution or as latexes.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: May 12, 1998
    Assignee: Michigan Molecular Institute
    Inventor: John C. Saam
  • Patent number: 5668244
    Abstract: A liquid polyester obtained by reacting a cyclic acid anhydride (A) containing at least 10 mol % of one of specific cyclic acid anhydrides with an epoxy compound (B) in a cyclic acid anhydride (A):epoxy compound (B) molar ratio of 10:8-10:12, can be applied with a conventionally generally used film-forming machine such as a roll coater or a printing machine, can easily give a film-forming material such as a solvent-free coating composition or ink and a curable liquid resin for use as an adhesive, is a low-temperature curing liquid polyester useful as a compatibilizer, a surface-tension modifier, a pigment dispersing agent and a metal chelating agent, and is curable in air in the presence of a relatively small amount of a catalyst.
    Type: Grant
    Filed: June 16, 1995
    Date of Patent: September 16, 1997
    Assignee: Toyo Ink Manufacturing Co., Ltd.
    Inventors: Miki Kawashima, Takeo Yamaguchi, Kunio Horiuchi, Hiromi Uchida
  • Patent number: 5508457
    Abstract: The invention is directed to a process for the transesterification of carboxylic acid esters, in which process a catalyst is used which is substantially insoluble in the reaction mixture under reaction conditions, said catalyst comprising at least one silicate of the Group IVB elements of the Periodic Table as the active component.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: April 16, 1996
    Assignees: Engelhard De Meern B.V., Fina Research S.A.
    Inventors: Cornelis R. Bayense, Herve Hinnekens, Julien Martens
  • Patent number: 5434278
    Abstract: Acetoglycerides are prepared in a solventless, single phase interesterification between triacetin and triglycerides bearing long C.sub.16 to C.sub.22 fatty acid residues by adding triglycerides bearing saturated C.sub.3 to C.sub.10 acid residues to the reaction mixture. The long acid residues may be hydrogenated before or after interesterification. In one embodiment, the C.sub.3 to C.sub.10 triglycerides are tripropionin, tributyrin, or mixtures of these; in another, these are triglycerides bearing C.sub.8 to C.sub.10 acid residues; and in a third, these are a mixture of tripropionin and/or tributyrin and C.sub.8 to C.sub.10 triglycerides. In preferred embodiments, the molar ratio of C.sub.16 to C.sub.22 triglycerides to triacetin and C.sub.3 to C.sub.10 triglycerides varies between 1:1 and 1:15, more narrowly between 1:3 and 1:12, and high temperatures are employed. The process diminishes catalyst use, obviates the need for high shear mixing, shortens reaction times, and simplifies purification steps.
    Type: Grant
    Filed: February 3, 1993
    Date of Patent: July 18, 1995
    Assignee: Nabisco, Inc.
    Inventors: Turiddu A. Pelloso, Allan D. Roden, Gilbert L. Boldt
  • Patent number: 5434281
    Abstract: 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: Grant
    Filed: May 31, 1994
    Date of Patent: July 18, 1995
    Assignee: L'Oreal
    Inventors: Guy Solladie, Guy Stone, Antonio Urbano-Pujol, Jean Maignan
  • Patent number: 5420317
    Abstract: Olefinically unsaturated adducts of propylene on polyunsaturated fatty acids with 18 to 22 carbon atoms or on esters of these fatty acids with C.sub.1 -C.sub.36 alkanols in molar ratios of propylene to fatty acids or fatty acid esters in the range from 1:1 to 2:1, obtainable by reacting the fatty acids or fatty acid esters with propylene at elevated temperature and pressure in the presence of compounds of the transition metals Ru, Rh, Pd, Ir and Pt as catalysts to form an olefinically unsaturated adduct.
    Type: Grant
    Filed: July 24, 1992
    Date of Patent: May 30, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Alfred Laufenberg, Arno Behr
  • Patent number: 5380894
    Abstract: A process for the production of hydroxy fatty acids and novel estolide compounds, each of which may be used as lubricants, greases, plasticizers and printing inks, as well as in cosmetics. The estolides are of the formula (I): ##STR1## wherein R.sub.1 is selected from C.sub.6 -C.sub.16 hydrocarbons which may be saturated or unsaturated, and branched or straight chain, and optionally substituted, such as with one or more hydroxy groups; R.sub.2 is independently selected from C.sub.2 -C.sub.17 hydrocarbons which may be saturated or unsaturated, and branched or straight chain, and optionally substituted, such as with one or more hydroxy groups; A is selected from C.sub.3 -C.sub.14 hydrocarbons which may be saturated or unsaturated, and branched or straight chain, and optionally substituted; n is greater than or equal to 1; y is an integer from 3-13; x is 1 or 2; and . . . designates a single or double carbon/carbon bond.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: January 10, 1995
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Douglas A. Burg, Robert Kleiman, Selim M. Erhan
  • Patent number: 5223621
    Abstract: Transvinylation process between vinyl acetate or vinyl propionate and a carboxylic acid of general formula (I),RCOOH (I)in which R represents a substituted or non-substituted alkyl, cycloalkyl, aralkyl or aromatic radical, in the presence of a palladium catalyst, in which the catalyst is obtained in situ, by reacting, in the reaction medium, a derivative of palladium chosen from the group constituted by palladium II acetate, nitrate or hydroxide and palladium deposited on charcoal, with a tertiary amine chosen from the group constituted by 2,2'-bipyridyl, orthophenanthroline or tetramethylethylenediamine, that the quantity of palladium used, expressed in gram-atom of palladium II per 100 moles of carboxylic acid of general formula (I) is between 0.005 and 1 and that the quantity of amine is greater than 1 and less than 10 moles per gram-atom of palladium II used and use for the preparation of certain products.
    Type: Grant
    Filed: January 6, 1992
    Date of Patent: June 29, 1993
    Assignee: Societe Francaise Hoechst
    Inventors: Jean-Claude Vallejos, Yani Christidis
  • Patent number: 5214172
    Abstract: Transvinylation of a vinyl ester with either an alcohol to form a vinyl ether or a carboxylic acid to form a vinyl ester of different molecular weight than the starting ester is catalyzed with a palladium catalyst which is introduced to the reaction mixture as a palladium carboxylate complexed with an aryl N-containing ligand and the activity of this reaction is significantly improved with the addition of a strong acid. Also described are phenanthroline compounds and their novel complexes with palladium acetate which are useful as transvinylation catalysts.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: May 25, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Francis J. Waller
  • Patent number: 5210207
    Abstract: The invention provides an improved process for the preparation of a vinyl derivative of a Bronsted acid, wherein a vinyl derivative of a first Bronsted acid is subjected to transvinylation by reactive distillation with a second Bronsted acid.
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Morteza Mokhtarzadeh, Rex E. Murray
  • Patent number: 5149851
    Abstract: Glycerides containing methylene-interrupted polyunsaturated fatty acid moieties are prepared by reacting a lower alkyl ester of the corresponding polyunsaturated fatty acid or desired mixture of fatty acids with glycerol in the presence of alkoxide ion as the catalyst and removing the lower alcohol as it is formed, preferably at a pressure below atmospheric pressure. Triglycerides of omega-3 fatty acids, such as EPA and DHA, were prepared and triglycerides of mixed polyunsaturated and monounsaturated or short or medium chain fatty acids can also be prepared using that approach.
    Type: Grant
    Filed: October 25, 1990
    Date of Patent: September 22, 1992
    Assignee: The United States of America as represented by the Secretary of Commerce
    Inventors: Virginia F. Stout, Erich J. Gauglitz, Jr., William B. Nilsson