Plural Alcoholic Or Phenolic Hydroxys (e.g., Glycerol, Castor Oil, Etc.) Patents (Class 554/168)
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Patent number: 10457892Abstract: This invention relates to a wax composition comprising one or more fatty acid diester compounds having the formula of R1 and R2 are each independently a substituted or unsubstituted C4 to C50 alkyl or aryl; and n1 is an integer from 2 to 10. This invention also relates to a wax composition comprising: a) one or more fatty acid monoester or diester compounds having the formula of: and b) one or more hydroxylated fatty acid diester compounds having the formula of In these formulae, R is H or COR1?; R1? and R2? are each independently a substituted or unsubstituted C4 to C50 alkyl or aryl; n2 is an integer from 2 to 24; m is an integer from 2 to 12; and .(OH)m represents 2 to 12 hydroxyl groups substituting for 2 to 12 hydrogen atoms in the alkyl groups R1? and/or R2?. Uses of the compositions are also disclosed.Type: GrantFiled: January 3, 2019Date of Patent: October 29, 2019Assignee: Iowa State University Research Foundation, Inc.Inventors: Tong Wang, Tao Fei
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Patent number: 9873843Abstract: A process for the conversion of a feedstock containing one or more fatty acid triglycerides to a mixture containing one or more fatty acid alkyl esters and t-alkyl glycerols, including reacting the feedstock with a compound of formula (I): R—O—RI??(I) wherein: RI is an alkyl, alkenyl or alkynyl having 1-18 carbon atoms; R is H or a tertiary alkyl group, wherein the reaction takes place in the presence of an acid transesterification catalyst by irradiation with microwaves and/or ultrasound and/or radio waves.Type: GrantFiled: February 4, 2014Date of Patent: January 23, 2018Assignee: CONSIGLIO NAZIONALE DELLE RICERCHEInventors: Giovanni Nicolosi, Carmelo Drago, Leonarda Francesca Liotta, Valeria La Parola, Maria Luisa Testa
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Patent number: 9591861Abstract: Provided is a fat or oil composition, comprising 50 mass % or more of diacylglycerols whose constituent fatty acids comprise 12 mass % or more of fatty acids having 20 or more carbon atoms and 5 mass % or less of a total content of eicosapentaenoic acid and docosahexaenoic acid, and having an iodine value of a fat or oil of 120 or less.Type: GrantFiled: August 21, 2012Date of Patent: March 14, 2017Assignee: KOA CORPORATIONInventors: Rika Homma, Yoshihide Asabu
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Patent number: 9273257Abstract: A method of producing biodiesel comprising the steps of collecting a raw material comprising a fatty acid and an oil; contacting the raw material with glycerol and a Lewis acid catalyst in a first reaction chamber at a selected pressure and temperature; separating water from the mixture product in a gas phase; and contacting the mixture product with a second alcohol and an alkali catalyst in a second reaction chamber to form a product comprising a fatty acid ester.Type: GrantFiled: June 4, 2010Date of Patent: March 1, 2016Inventors: Tara C. Mancini, David Bradley
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Patent number: 9193662Abstract: The present invention relates to a method for producing a mixture containing fatty acid monoglyceride from glycerin and a compound having at least one acyl group, selected from fatty acids and fatty acid glycerides, including: (i) a step of obtaining a mixture containing fatty acid monoglyceride by heating and reacting glycerin and a compound having at least one acyl group, selected from fatty acids and fatty acid glycerides in the presence of a catalyst; (ii) a step including adding glycerin, which is liquid and has a lower temperature than the temperature of the mixture, to the mixture to cool the mixture; and (iii) a step of separating the mixture containing fatty acid monoglyceride from glycerin, obtained in the step (ii), by separating layers.Type: GrantFiled: December 7, 2012Date of Patent: November 24, 2015Assignee: KAO CORPORATIONInventors: Yasukazu Kumita, Takeshi Shirasawa
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Patent number: 9174919Abstract: The invention discloses an improved process for preparing fatty acid esters with 100 mol % selectivity suitable as biodegradable lubricant base oils, comprising contacting a fatty compound with an alcohol in presence of a solid, phosphonate catalyst having molecular formula: M(X)2-nYn.mH2O where X refers to phenyl phosphonate, Y refers to HPO42? or HPO32?, M refers to a metal or metalloid ion preferably taken from the group consisting of Zr, Zn, Cd, Al, Sn, La and Ce, the value of n varies from 0.2 to 1.8 and the value of m varies from 0 to 5, wherein the fatty compound is a fatty acid or fatty acid methyl or ethyl ester or vegetable oil or animal fat or their mixture thereof and alcohol is a monohydric alcohol with 6 to 22 carbon atoms or a polyol with at least two hydroxyl groups.Type: GrantFiled: May 22, 2013Date of Patent: November 3, 2015Assignee: Council of Scientific and Industrial ResearchInventors: Darbha Srinivas, Mehejabeen Kotwal
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Patent number: 9157039Abstract: The present invention relates to a process for obtaining simultaneously several compositions comprising fatty acid alkyl esters (biodiesel), glycerol formal and fatty acid glycerol formal esters.Type: GrantFiled: November 8, 2013Date of Patent: October 13, 2015Assignee: INSTITUT UNIV. DE CIÈNCIA I TECHNOLOGIA, S.A.Inventors: Carles Estevez Company, Natividad Bayarri Ferrer, Josep Castells Boliart
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Publication number: 20150148554Abstract: The invention discloses an improved process for preparing fatty acid esters with 100 mol % selectivity suitable as biodegradable lubricant base oils, comprising contacting a fatty compound with an alcohol in presence of a solid, phosphonate catalyst having molecular formula: M(X)2-nYn.mH2O where X refers to phenyl phosphonate, Y refers to HPO42? or HPO32?, M refers to a metal or metalloid ion preferably taken from the group consisting of Zr, Zn, Cd, Al, Sn, La and Ce, the value of n varies from 0.2 to 1.8 and the value of m varies from 0 to 5, wherein the fatty compound is a fatty acid or fatty acid methyl or ethyl ester or vegetable oil or animal fat or their mixture thereof and alcohol is a monohydric alcohol with 6 to 22 carbon atoms or a polyol with at least two hydroxyl groups.Type: ApplicationFiled: May 22, 2013Publication date: May 28, 2015Inventors: Darbha Srinivas, Mehejabeen Kotwal
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Patent number: 9029494Abstract: Novel compounds of formula (1) wherein: A is especially a linear or branched divalent alkylene radical having between 1 and 10 carbon atoms, and Y is especially a hydrogen atom.Type: GrantFiled: September 10, 2010Date of Patent: May 12, 2015Assignee: Centre National de la Recherche Scientifique (C.N.R.S)Inventors: Henri Cramail, Aurélie Boyer, Eric Cloutet, Carine Alfos
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Patent number: 8993793Abstract: The present invention provides bifunctional silica mesoporous materials, including mesoporous silica nanoparticles (“MSN”), having pores modified with diarylammonium triflate and perfluoroaryl moieties, that are useful for the acid-catalyzed esterification of organic acids with organic alcohols.Type: GrantFiled: January 30, 2012Date of Patent: March 31, 2015Assignee: Iowa State University Research Foundation, Inc.Inventors: Chih-Hsiang Tsai, Hung-Ting Chen, Marek Pruski, Takeshi Kobayashi, Show-Ling Lee
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Publication number: 20150087850Abstract: A method for producing an ester polyol, comprising transesterifying a first ester polyol with a primary polyol to produce a second ester polyol, wherein the second ester polyol has a higher hydroxyl value than the first ester polyol.Type: ApplicationFiled: February 28, 2013Publication date: March 26, 2015Inventors: Herman Paul Benecke, Daniel B. Garbark
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Patent number: 8853436Abstract: Method for transesterification of fatty acid esters. The method includes contacting (i) a catalyst comprising at least one of barium oxide and apatite with (ii) a reaction medium comprising at least one of vegetable oil and fats.Type: GrantFiled: October 18, 2013Date of Patent: October 7, 2014Assignee: Petroleo Brasileiro S.A.-PetrobrasInventors: Márcio de Figueiredo Portilho, Alexander Rangel Bastos
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Patent number: 8802877Abstract: The present invention refers to a process for modifying epoxidized or non-modified vegetable oils. More specifically, it refers to the process through which vegetable oils and alcohols are converted into fatty acid alkyl esters through transesterification. The present invention also refers to the products obtained through the process disclosed herein.Type: GrantFiled: December 17, 2009Date of Patent: August 12, 2014Assignee: NPC Industrias Quimicas LtdaInventors: Milton Sobrosa Cordeiro, Sérgio Teixeira, Ariovaldo Fernandes Junior
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Patent number: 8658813Abstract: A new class of oleochemical based polyol esters of general formula 1 are prepared by esterification of different polyols having 5-6 carbon atoms and 2-4 hydroxyl groups with 10-undecenoic acid or/and undecanoic acid with a hydroxyl value of ?1.0 mg KOH/g. Wherein R1, R2, R3 is selected from a group consisting of CH3—, CH3CH2—, —CH2OCOR4 wherein R4 is selected from CH2?CH—(CH2)8— or CH3—(CH2)9—, individually or in combination thereof. The resulting esters were characterized for lubricant properties like viscosity, viscosity index, pour point, flash point and copper corrosion tests. The properties indicate their potential as promising lubricant base stocks for automotive lubricants, metal working oil, hydraulic oil and other industrial applications. Vegetable oils provide most of the desirable lubricant properties such as good boundary lubrication, high viscosity index, high flash point and low volatility.Type: GrantFiled: May 14, 2009Date of Patent: February 25, 2014Assignee: Council of Scientific & Industrial ResearchInventors: Venkata Padmaja Korlipara, Venkata Surya Koppeswara Rao Bhamidipati, Satya Bhaskar Potula, Badari Narayana Prasad Rachapudi, Arun Kumar Singh
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Patent number: 8491857Abstract: Processes and apparatus produce economically feasible biodiesel without subsidies. Toward that end, integrated small plants process materials containing lipids with anhydrous bioethanol as solvent and reactant, and sulfuric acid and potassium hydroxide mainly as catalysts to produce up to 3 million gallons of biodiesel per plant per year. The product is predominantly fatty acids ethyl esters (FAEE) and a chemically-enhanced organic fertilizer as byproduct. The raw material may include a wide variety of non-edible solid matter that contains lipids, which normally have from 0.5% to 80% by weight of free fatty acids in total oils. Multiple apparatus makes this process feasible. In addition to not competing with food production, since they supply fertilizer for small scale farmers, the processes and apparatus allow sustainable liquid fuel production.Type: GrantFiled: September 5, 2012Date of Patent: July 23, 2013Inventor: Antonio Cantizani
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Patent number: 8481771Abstract: Processes for producing biodiesel compositions are disclosed. FFAs present in the triglycerides can be removed by reaction with isobutylene, or by Kolbe electrolysis. The Kolbe electrolysis can be performed on the starting material, or on the crude glycerol. The triglycerides are transesterified to form alkyl esters of the fatty acids and glycerol. The transesterification reaction can be catalyzed by an alkoxide, rather than a hydroxide, to help keep the glycerol by-product dry. The alkoxide salt can be neutralized by reaction with a dry acid, such as gaseous hydrogen chloride or sulfuric acid, and the resulting alcohol removed by distillation, and at least a portion of the neutralized salt can be removed by filtration or decantation. The process can provide improved biodiesel yields, and glycerol pure enough for use directly in glycerol ether manufacture.Type: GrantFiled: March 21, 2008Date of Patent: July 9, 2013Assignee: CPS Biofuels, Inc.Inventors: David Bradin, Guerry L. Grune
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Patent number: 8426621Abstract: Methods for producing refined rice bran oil that include caustic treatment step(s) in an amount that is less than or equal to a theoretical amount of caustic required to neutralize practically all of the free fatty acids in the rice bran oil, but avoiding addition of excess caustic. An objective is to retain a high level of oryzanol in the refined oil.Type: GrantFiled: February 22, 2010Date of Patent: April 23, 2013Assignee: Riceland Foods, Inc.Inventors: Nahid Rutherford, Don R. McCaskill, Gary E. Nelms, Larry D. Corley
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Patent number: 8383846Abstract: A method of preparing a composition of alcohol esters of linear monocarboxylic acids with 6 to 26 carbon atoms from a vegetable or animal oil, neutral or acid, virgin or recycled, with monoalcohols having 1 to 18 carbon atoms, in the presence of a catalyst combining at least a solid solution of ZnxAl2O(3+x) type, wherein x ranges between 0 and 1 (end points excluded), and free ZnO present between 7 and 30 mass %, allows to directly obtain, in one or more stages, an ester that can be used as fuel and a pure glycerin.Type: GrantFiled: December 23, 2009Date of Patent: February 26, 2013Assignee: IFP Energies NouvellesInventors: Delphine Bazer-Bachi, Vincent Coupard, Sylvie Maury, Bernadette Rebours
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Publication number: 20130005936Abstract: Novel compounds of formula (1) wherein: A is especially a linear or branched divalent alkylene radical having between 1 and 10 carbon atoms, and Y is especially a hydrogen atom.Type: ApplicationFiled: September 10, 2010Publication date: January 3, 2013Applicant: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.)Inventors: Henri Cramail, Aurélie Boyer, Eric Cloutet, Carine Alfos
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Patent number: 8328997Abstract: This invention relates to the design of a process by intermittent dielectric heating combined with a recycling system. This process consists in subjecting reagents to electromagnetic waves selected in the frequencies ranging between 300 GHz and 3 MHz intermittently using a recycling system. This process enables the treatment of oils that are hardly absorbent as well as great investment savings. This process enables operation on different scales, whether in laboratories, on a semi-industrial or industrial scale, without forfeiting the advantages of continuous dielectric heating.Type: GrantFiled: June 29, 2009Date of Patent: December 11, 2012Assignee: Aldivia SAInventors: Pierre Charlier De Chily, Mikaële Raynard
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Patent number: 8324413Abstract: In the present invention, a fuel composition and a process for making the same are disclosed. Specifically, in the present invention, triglycerides useful for distillate fuels are described along with their method for preparation from Fischer-Tropsch acid by-products and the glycerol by-product from biodiesel generation. By using these two by-product streams, the overall efficiency of both processes is improved and a new source of distillate fuels is created. These triglycerides can be used to improve the lubricity of Fischer-Tropsch derived distillate fuels. In addition, these triglycerides also have low melting points and have viscosities compatible with distillate fuels.Type: GrantFiled: December 16, 2009Date of Patent: December 4, 2012Assignee: Texaco Inc.Inventor: Dennis J. O'Rear
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Patent number: 8308975Abstract: A polyol includes the reaction product of an epoxidized oil and an organic acid. The epoxidized oil and the organic acid are reacted in the presence of a Lewis base catalyst including at least one of a phosphorous atom or a nitrogen atom. The polyol is formed by a method that includes the step of reacting the epoxidized oil with the organic acid in the presence of the Lewis base catalyst.Type: GrantFiled: October 25, 2011Date of Patent: November 13, 2012Assignee: BASF SEInventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore Michael Smiecinski
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Patent number: 8304566Abstract: Processes and apparatus produce economically feasible biodiesel without subsidies. Toward that end, integrated small plants process materials containing lipids with anhydrous bioethanol as solvent and reactant, and sulfuric acid and potassium hydroxide mainly as catalysts to produce up to 3 million gallons of biodiesel per plant per year. The product is predominantly fatty acids ethyl esters (FAEE) and a chemically-enhanced organic fertilizer as byproduct. The raw material may include a wide variety of non-edible solid matter that contains lipids, which normally have from 0.5% to 80% by weight of free fatty acids in total oils. Multiple apparatus makes this process feasible. In addition to not competing with food production, since they supply fertilizer for small scale farmers, the processes and apparatus allow sustainable liquid fuel production.Type: GrantFiled: March 9, 2012Date of Patent: November 6, 2012Inventor: Antonio Cantizani
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Patent number: 8288573Abstract: 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: GrantFiled: December 15, 2006Date of Patent: October 16, 2012Assignees: China Petroleum & Chemical Corporation, Research Institute of Petroleum Processing, SinopecInventors: Haijing Wang, Zexue Du, Enze Min, Guoqiang Gao
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Patent number: 8227632Abstract: A process of preparing alkyl esters of free fatty acids, including, but not limited to, biodiesel, is described herein.Type: GrantFiled: June 18, 2010Date of Patent: July 24, 2012Assignee: Philadelphia Fry-O-DieselInventors: William Wesley Berry, Brian J. Ratigan
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Publication number: 20120174473Abstract: A methodology for separation and subsequent handling of FAME fractions of biodiesel, comprising of the steps, providing a biodiesel containing several different FAME fractions mixed together, the biodiesel being at a first temperature wherein at the first temperature none of the FAME fractions of the biodiesel have crystallized; bringing the biodiesel to a first crystallizing temperature, wherein when the biodiesel reaches the first crystallizing temperature, a first FAME fraction remains in a non-crystallized, liquid phase while the remaining FAME fractions crystallize; and separating the liquid first FAME fraction from the remaining crystallized FAME fractions.Type: ApplicationFiled: January 6, 2012Publication date: July 12, 2012Applicant: GREEN FUELS, LIMITEDInventor: Duane Johnson
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Publication number: 20120172439Abstract: The present disclosure provides methods for generating percarboxylic acid compositions and/or peroxycarboxylic acid compositions formed external to a point of use in non-equilibrium reactions for use in certain bleaching and antimicrobial applications, in particular laundry applications. The compositions are generated external to a point of use, at alkaline pH levels, viz. greater than about pH 12, and optionally suitable for use with detergents and/or surfactants for synergistic bleaching efficacy. Methods of bleaching and/or disinfecting are further provided.Type: ApplicationFiled: December 20, 2011Publication date: July 5, 2012Applicant: Ecolab USA Inc.Inventors: Jonathan P. Fast, Robert D.P. Hei, Richard Staub, Thomas J. Dürrschmidt, Peter J. Forth, Junzhong Li, David D. McSherry, Thomas Merz, Johannes G. Winter
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Patent number: 8188305Abstract: A method is disclosed for obtaining an alkyl ester fuel, i.e., a biodiesel, and alcohol from a feedstock mixture of free fatty acids and/or glycerides mixed with a simple alcohol, such as methanol. The method uses an electrostatic probe to provide an electrical field within the reactor. This causes the glycerin molecules to precipitate out of the feedstock mixture. A drain is provided in the reactor, to drain the glycerin from the reactor. When the precipitated glycerin reaches a level to make contact with the electrostatic probe, an electrical circuit is closed, which causes the drain to open. When the level drops, the drain closes. Glycerin absorbs water and draining glycerin from the reactor naturally dehydrates the fuel.Type: GrantFiled: February 1, 2010Date of Patent: May 29, 2012Inventor: David Miller
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Patent number: 8153746Abstract: Methods of making unsaturated modified vegetable oil-based polyols are described. Also described are methods of making oligomeric modified vegetable oil-based polyols. An oligomeric composition having a modified fatty acid triglyceride structure is also described. Also, methods of making a polyol including hydroformylation and hydrogenation of oils in the presence of a catalyst and support are described.Type: GrantFiled: June 2, 2010Date of Patent: April 10, 2012Assignee: Cargill, IncorporatedInventors: Zoran S. Petrovic, Ivan X. Javni, Alisa Zlatanic, Andrew Xiuguang Guo
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Publication number: 20120022165Abstract: The present invention is directed to transdermal compositions and the uses thereof. These compositions include at least one of the following components: a C1-C6 dialkyl, C12-C30 dialkyl quaternary ammonium salt, a C12-C30 fatty acid, a nitrogenous organic base, C12-30 fatty alcohol, monoglyceride or the reaction products thereof.Type: ApplicationFiled: September 30, 2011Publication date: January 26, 2012Applicant: MICRODERMIS CORPORATIONInventors: Griscom Bettle, III, William S. Coury
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Patent number: 8084631Abstract: A polyol includes the reaction product of an epoxidized oil and an organic acid. The epoxidized oil and the organic acid are reacted in the presence of a Lewis base catalyst including at least one of a phosphorous atom or a nitrogen atom. The polyol is formed by a method that includes the step of reacting the epoxidized oil with the organic acid in the presence of the Lewis base catalyst.Type: GrantFiled: May 15, 2008Date of Patent: December 27, 2011Assignee: BASF SEInventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore M. Smiecinski
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Publication number: 20110312044Abstract: In an alcohol fermentation process, oil derived from biomass is chemically converted into an extractant available for in situ removal of a product alcohol such as butanol from a fermentation broth. The glycerides in the oil can be chemically converted into a reaction product, such as fatty acids, fatty alcohols, fatty amides, fatty acid methyl esters, fatty acid glycol esters, and hydroxylated triglycerides, and mixtures thereof, which forms a fermentation product extractant having a partition coefficient for a product alcohol greater than a partition coefficient of the oil of the biomass for the product alcohol. Oil derived from a feedstock of an alcohol fermentation process can be chemically converting into the fermentation product extractant.Type: ApplicationFiled: June 17, 2011Publication date: December 22, 2011Applicant: BUTAMAX(TM) ADVANCED BIOFUELS LLCInventors: DOUGLAS ROBERT ANTON, JELENA CIRAKOVIC, BRUCE A. DINER, MICHAEL CHARLES GRADY, FRANCIS J. WOERNER
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Patent number: 8030505Abstract: A process for producing lower alkyl esters of higher fatty acids from an oil phase and lower alcohols, in a catalytic transesterification process in the presence of an alkaline catalyst. A reaction mixture is provided by mixing oil-phase fatty acids with a solution comprising methanol and an alkaline catalyst comprising sodium methylate. The transesterification reaction of the reaction mixture is accelerated by subjecting the reaction mixture to a temperature above the boiling point of methanol and pressurizing the reaction mixture sufficiently to prevent boil-off. A centrifugal separator separates glycerin phase from biodiesel phase of a resulting reaction product stream. The biodiesel phase is washed by counter-current extraction.Type: GrantFiled: December 21, 2007Date of Patent: October 4, 2011Assignee: B&P Process Equipment and Systems, LLCInventors: Abbey Martin, Joseph E. Flynn, Harold Lange
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Patent number: 7960575Abstract: A process for forming an ester from 1,3-propanediol comprising providing 1,3-propanediol with at least 90% biobased carbon, contacting the 1,3-propanediol with an acid, thereby forming the ester, and recovering the ester is provided. The acid can be an organic acid. Additionally, a process for producing an ester, either or both a monoester and a diester, from biologically-produced 1,3-propanediol is provided. This process includes providing 1,3-propanediol produced biologically through fermentation and catalytic conversion of atmospheric carbon, contacting the 1,3-propanediol with an organic acid, wherein said ester is produced; and recovering the ester. In this process the 1,3-propanediol can have has at least 95% biobased carbon, or can have 100% biobased carbon.Type: GrantFiled: February 12, 2007Date of Patent: June 14, 2011Assignee: DuPont Tate & Lyle Bio Products Company, LLCInventors: Gyorgyi Fenyvesi, Raja Hari Prasad R. Poladi
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Publication number: 20110061289Abstract: A method of manufacturing a biodiesel fuel that comprises generating micro-droplets of a first reactant and mixing the micro-droplets of the first reactant with a second reactant that is substantially immiscible with the first reactant. The method also comprises transferring the mixture of the first reactant and second reactant into a transesterification reaction vessel. The first reactant is one of an alcohol or oil, and the second reactant is the other of the oil or the alcohol.Type: ApplicationFiled: September 13, 2010Publication date: March 17, 2011Applicant: TEXAS TECH UNIVERSITY SYSTEMInventor: Uzi Mann
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Patent number: 7851643Abstract: A method of manufacturing an ester composition comprising ethyl esters of linear monocarboxylic acids having 6 to 26 carbon atoms from a vegetable or an animal oil, neutral or acid, virgin or recycled, the method comprising: a stage 1 of reaction of vegetable or animal oil with methanol, in the presence of a heterogeneous catalyst comprising a combination of at least one metallic oxide and alumina or a combination of at least two metallic oxides and possibly alumina, and a stage 2 of reaction of the product from stage 1 with ethanol in the presence of a heterogeneous catalyst as defined for stage 1, so as to obtain from vegetable or animal oils, a mixture of fatty acid esters rich in fatty acid ethyl esters and a glycerin of high purity.Type: GrantFiled: September 15, 2006Date of Patent: December 14, 2010Assignee: IFP Energies NouvellesInventors: Gérard Hillion, Bruno Delfort
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Patent number: 7786239Abstract: Methods of making unsaturated modified vegetable oil-based polyols are described. Also described are methods of making oligomeric modified vegetable oil-based polyols. An oligomeric composition having a modified fatty acid triglyceride structure is also described. Also, methods of making a polyol including hydroformylation and hydrogenation of oils in the presence of a catalyst and support are described.Type: GrantFiled: June 24, 2005Date of Patent: August 31, 2010Assignee: Pittsburg State UniversityInventors: Zoran S. Petrovic, Ivan Javni, Alisa Zlatanic, Andrew Guo
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Patent number: 7767838Abstract: The invention provides a process for producing a monoglyceride-containing composition by reacting glycerin with at least one kind of acyl-containing compound selected from fatty acid and glycerin ester, the reaction being conducted with a catalyst containing at least one metal selected from iron, cobalt and manganese in an amount of 0.1 to 60 ppm in terms of metal (weight ratio to the total weight of glycerin and the acyl-containing compound), as well as a process for producing a monoglyceride-containing composition by reacting glycerin with at least one kind of acyl-containing compound selected from fatty acid and glycerin ester, including a step of maintaining the amount of water at 500 to 5000 ppm in the reaction system after the degree of conversion in the reaction of glycerin with fatty acid reaches 90% or more based on the fatty acid, or during the ester exchange reaction of glycerin with glycerin ester.Type: GrantFiled: June 3, 2004Date of Patent: August 3, 2010Assignee: Kao CorporationInventors: Hiroki Sawada, Jiro Hashimoto, Haruya Mino, Toshitsugu Maeda
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Publication number: 20100168255Abstract: The present invention relates to a process for preparing a compound having at least one ether group, at least one ester group, at least one amino group or at least one urethane group by a1) preparing 1,2-propanediol by means of a process wherein glycerol is hydrogenated in the presence of a catalyst, glycerol being reacted to at most 95% and a 1,2-propanediol phase obtained and a2) reacting the 1,2-propanediol phase with a compound having at least one active hydrogen atom, at least one epoxide group, at least one ester group or at least one isocyanate group. The present invention relates to the compounds which can be obtained using this process and the chemical products, emulsions, cosmetic formulations, plastics material compositions and drilling compositions prepared using the compound and the use and preparations thereof.Type: ApplicationFiled: June 11, 2008Publication date: July 1, 2010Inventors: Alfred Westfechtel, Elke Grundt, Peter Daute, Norbert Klein
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Patent number: 7629478Abstract: A process for preparing palm-based polyol monomer includes reacting unsaturated fatty acids or its corresponding triglycerides with polyhydric alcohol. In particular, one example uses oleic acid with about 70% purity as the starting material for preparing the polyol monomer. Moreover, another example uses refined, bleached, and deodorized (RBD) palm olein as an alternative to oleic acid as the starting material. The preparation of the polyol monomer involves the production of monoglyceride of unsaturated fatty acids, which was further epoxidized with peracid and finally ring opened with polyhydric alcohols. Such polyol monomer is used as a raw material for the production of various types of polyurethane products.Type: GrantFiled: November 6, 2006Date of Patent: December 8, 2009Assignee: Malaysian Palm Oil Board (MPOB)Inventors: Hoong Seng Soi, Nur Musyahadah Mazalan, Mohd Nurhisham Sattar, Tuan Noor Mazne Tuan Ismail, Hazimah Abu Hassan, Ooi Tian Lye, Salmiah Ahmad, Mohd Basri Wahid, Tan Sri Datuk Yusof Basiron
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Patent number: 7622600Abstract: A continuous biofuel production process includes the steps of introducing a feedstock containing fatty acids and triglycerides into a first reaction vessel, in which alkyl esters are produced through esterification of free fatty acids. The alkyl esters and triglycerides are introduced into a second reaction vessel, in which at least a portion of the triglycerides are converted to alkyl esters and glycerin through transesterification. The alkyl esters, glycerin, and remaining triglycerides are introduced into a third reaction vessel, in which at least a portion of the remaining triglycerides are converted to alkyl esters and glycerin through transesterification.Type: GrantFiled: January 5, 2007Date of Patent: November 24, 2009Assignee: Redland Industries, Inc.Inventor: Wesley Drew Marr
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Patent number: 7566794Abstract: A method allowing, from natural fat or oils, or from other glyceride mixtures, to obtain fatty acid ethyl esters that can be used as gas oil substitutes, comprises: stage (a) oil, fat or a glyceride mixture is transesterified by ethanol using a soluble catalyst or a catalyst that becomes soluble during the reaction; stage (b) resultant glycerin is decanted and removed, without requiring an excess ethanol evaporation operation, stage (c) a second transesterification is conducted to obtain a product whose ester content is at least 97% by mass, stage (d) evaporation of excess ethanol is carried out in the presence of the catalyst under suitable conditions preventing a reverse transesterification reaction, the resultant ethanol being practically anhydrous, stage (e) the ester undergoes purification by water wash sequences, and stage (f) the ester is dried under reduced pressure.Type: GrantFiled: September 20, 2006Date of Patent: July 28, 2009Assignee: Institut Francais du PetroleInventors: Gérard Hillion, Bruno Delfort
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Publication number: 20090187035Abstract: A system and method for producing fatty acid alkyl esters is provided. The method includes forming a reactant stream, which includes triacylglycerides, alkanol, basic transesterification catalyst and, optionally, glycerol, and mixing the reactant stream under high shear mixing conditions to provide a mixed stream comprising fatty acid alkyl ester.Type: ApplicationFiled: January 22, 2008Publication date: July 23, 2009Inventors: Myong Ko, Krishna Kumar N.S., John Hahn, Harapanahalli S. Muralidhara
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Publication number: 20090163731Abstract: A process for producing lower alkyl esters of higher fatty acids from an oil phase and lower alcohols, in a catalytic transesterification process in the presence of an alkaline catalyst. A reaction mixture is provided by mixing oil-phase fatty acids with a solution comprising methanol and an alkaline catalyst comprising sodium methylate. The transesterification reaction of the reaction mixture is accelerated by subjecting the reaction mixture to a temperature above the boiling point of methanol and pressurizing the reaction mixture sufficiently to prevent boil-off. A centrifugal separator separates glycerin phase from biodiesel phase of a resulting reaction product stream. The biodiesel phase is washed by counter-current extraction.Type: ApplicationFiled: December 21, 2007Publication date: June 25, 2009Applicant: B&P Process Equipment and Systems, LLCInventors: Abbey Martin, Joseph E. Flynn, Harold Lange
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Patent number: 7544763Abstract: The present invention relates to a manufacturing process for producing a polyol from a fatty acid ester in-situ. The process does not use any added organic or inorganic acid catalyst. The polyol produced by the process is essentially free of any cation or anion. The fatty acid ester oil epoxidation and hydroxylation reactions can occur progressively in the same reactor for essentially a one-pot reaction. The polyol produced by the process is essentially free of any cation or anion. The polyol can be used to produce polyurethanes having improved properties.Type: GrantFiled: November 7, 2006Date of Patent: June 9, 2009Assignee: Arkema Inc.Inventor: Mohammad Kazemizadeh
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Patent number: 7501393Abstract: A composition is described herein comprising cyclosporin A, polysorbate 80, a polyoxyethylene stearate, and an oil; wherein the composition is an emulsion which is ophthalmically acceptable. Methods of treating diseases or conditions using said compositions, and medicaments related thereto, are also disclosed herein.Type: GrantFiled: July 27, 2005Date of Patent: March 10, 2009Assignee: Allergan, Inc.Inventors: Walter L. Tien, Richard Graham, James N. Chang
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Patent number: 7501533Abstract: Process for preparing lysophosphatidylcholine by selective monoacylation of glycerophosphorylcholine (1), in the presence of an acylating agent and of a dialkyltin derivative, according to the following diagram: The process is particularly simple and has high overall yields.Type: GrantFiled: December 6, 2005Date of Patent: March 10, 2009Assignee: Chem SpAInventors: Lorenzo De Ferra, Stefano Servi, Ezio Fasoli, Mauro Anibaldi, Daniele Scorretti
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Patent number: 7473791Abstract: This invention provides a process for synthesizing biodiesel from renewable oils, comprising: carrying out a transesterification reaction, in the presence of an enzyme catalyst, between a low carbon fatty acid ester RCOOR? as an acyl acceptor and a renewable oil, wherein the molar ratio of the low carbon fatty acid ester to the renewable oil is in the range of from 3:1 to 20:1, the transesterification reaction producing a glycerine tri-(low carbon) carboxylic ester by-product, and reacting the glycerine tri-(low carbon) carboxylic ester by-product with a low carbon alcohol R?OH to obtain the low carbon fatty acid ester, wherein the low carbon fatty acid ester is capable of being recycled in a further round of biodiesel synthesis, wherein R and R? are independently selected from the group consisting of alkyls with one to four carbon atoms.Type: GrantFiled: January 15, 2004Date of Patent: January 6, 2009Assignee: Tsinghua UniversityInventors: Wei Du, Yuanyuan Xu, Dehua Liu
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Publication number: 20090005583Abstract: A method for the preparation of a polyol fatty acid ester utilizes a combination of methyl soyate and a polyol in a molar ratio of approximately 2:1 in the presence of a basic catalyst to produce a fatty acid ester. Methanol is removed during a distillation process to drive the reaction process. Optionally, gas sparging can be utilized to aide in methanol recovery. In one embodiment, the method is employed to produce a propylene glycol disoyate product that does not require further purification or distillation to remove a relatively high boiling methyl soyate reactant.Type: ApplicationFiled: June 30, 2008Publication date: January 1, 2009Inventor: Herman P. Benecke
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Patent number: 7411079Abstract: A process for preparing a mixture of cetyl myristate and cetyl palmitate comprising reacting both myristic and palmitic acid with cetyl alcohol with an acid catalyst and one aromatic hydrocarbon at an elevated temperature and recovering from the aromatic hydrocarbon fraction the cetyl myristate and cetyl palmitate.Type: GrantFiled: August 31, 2001Date of Patent: August 12, 2008Assignee: Meracol Corporation LimitedInventors: Dianne Cadwallader, Parag Jhaveri