Molecular Rearrangement Of The Acid Moieties Of Glyceride Esters (e.g., Random Or Directed Low Temperature Intra- Or Inter-esterification Of Fats, Oils, Etc.) Patents (Class 554/169)
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Patent number: 6833463Abstract: The invention provides reaction mixtures comprising polyols, triglycerides, base initiators and phase-transfer catalysts for performing transesterification reactions. The reaction product comprises a mixture of polyol monoesters, polyol diesters, triglycerides and glycerol.Type: GrantFiled: February 24, 2004Date of Patent: December 21, 2004Assignee: PTC Organics, Inc.Inventors: Marc E. Halpern, Darrell Crick
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Patent number: 6812359Abstract: A method for preparing a fatty acid ester with suppressing the discharge of unreacted reactants and/or intermediate products, which comprises reacting fats and oils with a monohydric alcohol in a reactor under conditions where the monohydric alcohol is in a supercritical state, wherein a reaction mixture containing unreacted reactants and/or intermediate products is recycled to the reactor.Type: GrantFiled: December 31, 2001Date of Patent: November 2, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Fumisato Goto, Toshio Sasaki, Katsuyuki Takagi
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Patent number: 6777213Abstract: A process for recovering carboxylic acids from an aqueous mixture such as a fermentation broth using a solvent containing at least one olefin without the need for first removing the spent microorganism cells is provided. A co-solvent which increases the partition coefficient of the solvent relative to the carboxylic acid may optionally be included. The resulting carboxylic acid is hydrogenated to produce a saturated carboxylic acid.Type: GrantFiled: August 13, 2003Date of Patent: August 17, 2004Assignee: Cognis CorporationInventor: Michael D. Staley
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Patent number: 6770768Abstract: The invention relates to a substance which lowers LDL cholesterol levels in serum and which is fat soluble &bgr;-sitostanol fatty acid ester, and to a method for preparing and using the same. The substance can be taken orally as a food additive, food substitute or supplement. A daily consumption of the &bgr;-sitostanol ester in an amount between about 0.2 and about 20 g/day has been shown to reduce the absorption of biliary and endogenic cholesterol.Type: GrantFiled: November 7, 2002Date of Patent: August 3, 2004Assignee: Raisio Benecol, Ltd.Inventor: Ingmar Wester
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Patent number: 6768015Abstract: A method for making alkyl esters, or methylester specifically, such as biodiesel, from an oil source is described. The method involves simultaneously reacting the free fatty acids and glycerides of the oil source with methanol, under pressure up to 500 psia, into fatty acid alkyl esters. The conversion is catalyzed by an acid at temperatures between about 80° C. to about 200° C.Type: GrantFiled: August 12, 2003Date of Patent: July 27, 2004Assignee: Stepan CompanyInventors: Franz J. Luxem, William M. Troy
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Patent number: 6762313Abstract: Processes for preparing linoleic acid raw materials are described wherein the processes comprise: (a) transesterifying a triglyceride component with an alcohol having from 1 to 4 carbon atoms, at a temperature of from 80 to 120° C., to form a transesterification mixture comprising linoleic acid esters and one or more by-products selected from the group consisting of glycerides, free glycerol, and soaps, wherein the triglyceride component is comprised of at least 60% by weight linoleic acid; and (b) removing the one or more by-products from the transesterification mixture.Type: GrantFiled: March 13, 2003Date of Patent: July 13, 2004Assignee: Cognis Deutschland GmbH & Co. KGInventors: Albert Strube, Uwe Hoemmerich, Bernhard Gutsche
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Patent number: 6723863Abstract: A process of producing a light-colored, high-monoester mixture from a polyol and an oil is provided wherein the process eliminates the use of organic solvents, multiple water washings and/or molecular distillation. The reactants, a polyol and an oil, described herein, condense in the presence of a catalyst, described herein, at a temperature range from about 180° C. to about 280° C. under an inert atmosphere or the vapor pressure of the polyol with a pressure of about 0 to about 500 psig to yield a monoester mixture possessing a desirable monoester composition and color. The present process yields a final product similar to that of processes which require the use of solvents, multiple water washings and/or molecular distillation.Type: GrantFiled: August 7, 2002Date of Patent: April 20, 2004Assignee: Archer-Daniels-Midland CompanyInventors: Inmok Lee, George Poppe
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Patent number: 6696583Abstract: A method for the preparation of fatty acid alkyl esters by transesterification, in particular catalytic transesterification, of a mixture of triglycerides and fatty acids, wherein from a reaction mixture, in which the transesterification is carried out, an ester phase containing fatty acid alkyl esters and a glycerol phase containing fatty acids are formed, which are separated from each other, and the fatty acids are separated from the glycerol phase, whereby a fatty acid phase containing fatty acids is formed, which fatty acids are esterified with an alcohol, which method is characterized in that the fatty acid phase is mixed with a further mixture of triglycerides and fatty acids and the fatty acids contained in the obtained mixture are esterified with an alcohol, whereby an esterification mixture containing triglycerides and fatty acid alkyl esters is obtained, which esterification mixture is transesterified with alcohol so as to form further fatty acid alkyl esters.Type: GrantFiled: June 4, 2002Date of Patent: February 24, 2004Assignees: BDI Anlagenbau Gesellschaft mbHInventors: Michael Koncar, Martin Mittelbach, Helmut Gössler, Wilhelm Hammer
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Patent number: 6664404Abstract: An improved process for the manufacture of monoesters of polyhydroxyalcohols to high yields and high purities.Type: GrantFiled: May 14, 2002Date of Patent: December 16, 2003Assignee: Infineum International Ltd.Inventor: Graham Jackson
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Patent number: 6620952Abstract: Processes for the synthesis of polyol fatty acid polyester by transesterification of a polyol comprise reacting polyol with a first portion of fatty acid lower alkyl ester to provide a first step reaction product in which substantially all of the polyol is reacted with at least one fatty acid lower alkyl ester. The process then employs a multistage column for further transesterification of the first step reaction product. Partially esterified polyol, a second portion of fatty acid lower alkyl ester and catalyst are fed to the column to form a mixture and cause further transesterification of the partially esterified polyol and fatty acid lower alkyl ester, with lower alkyl alcohol being formed as a by product. The resulting liquid mixture of reactants and product is passed in a first direction between adjacent stages through the column for further reaction of partially esterified polyol with fatty acid lower alkyl ester.Type: GrantFiled: September 4, 2001Date of Patent: September 16, 2003Assignee: The Procter & Gamble Co.Inventor: Patrick Joseph Corrigan
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Patent number: 6608223Abstract: Unique structured lipids obtained from interestifying coconut oil with free fatty acids obtained from hydrolysis of triglycerides of an animal source, said structured lipids rich in omega-3-poly unsaturated fatty acid and medium chain fatty acid and a process for the production of said structured lipids.Type: GrantFiled: October 22, 2001Date of Patent: August 19, 2003Assignee: Council of Scientific and Industrial ResearchInventors: Reena Rao, Kari Sambaiah, Belur Ramaswamy Lokesh
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Patent number: 6596886Abstract: The invention relates to a process for manufacturing non-oily emollients with a molecular weight below about 600 Dalton, preferably below 550 Dalton, and still more preferably below about 450 Dalton, based on alcohol and fatty acid esters (wax-esters), which consists of the following steps: a) interesterification of the triglycerides contained in a fatty material by a primary alcohol, in the presence of a catalyst; b) elimination of the catalyst; c) distillation of the residual alcohol preferably in the presence of a bleaching agent followed by elimination of the bleaching agent; d1) either frigelisation of the preferably bleached residue such that residual glycerides are at least partially crystallized, followed by elimination of said crystallized residual glycerides, d2) or hydrogenation of the residue, preferably bleached.Type: GrantFiled: February 15, 2002Date of Patent: July 22, 2003Assignee: SophimInventor: Georges Cecchi
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Patent number: 6570030Abstract: A fatty acid ester prepared by treating botanical seeds or fruits with a monohydric alcohol having 1 to 10 carbon atoms under pressure at a temperature of at least 180° C., preferably under supercritical conditions.Type: GrantFiled: December 14, 2001Date of Patent: May 27, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Fumisato Goto, Toshio Sasaki
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Patent number: 6538146Abstract: The present invention relates to a method for producing fatty acid esters of monovalent alkyl alcohols by base-catalyzed transesterification of fatty acid esters of polyvalent alcohols. In said method, oils are used which contain free fatty acids and phosphatides, in addition to fatty acid esters of polyvalent alcohols. The method consists of several stages. The fatty acids contained in the starting material are treated with a base mixture of glycerine and a catalyst. This mixture is produced as a polar phase in the following transesterification stages and can be separated from the reaction mixture, using phase separation. Calculation procedures are provided for determining the minimum amount of catalyst necessary, depending on the acid number of the oil. The invention also relates to the use of esters produced by this method as diesel fuels.Type: GrantFiled: December 7, 2001Date of Patent: March 25, 2003Assignee: At Agrar-Technik GmbHInventor: Ralf Turck
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Patent number: 6537787Abstract: A process for obtaining polyunsaturated fatty acid concentrates comprising subjecting a fish oil containing docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA), to a selective enzymatic hydrolysis in position 1, 3 or 2, to obtain a mixture of free fatty acids, monoglycerides and diglycerides, separating the constituents of this mixture, collecting the free fatty acids which are purified by crystallization from urea, to increase the EPA and DHA content, decomplexing the isolated fatty acids by an inter-esterification between the free fatty acids concentrated into polyunsaturated fatty acids and the crude oil, in the presence of a lipase specific for position or steric hindrance, to obtain a mixture enriched with polyunsaturated fatty acid triglycerides which is separated and freed from the free fatty acids and a process for enrichment with polyunsaturated fatty acids (EPA, DHA) of phospholipids by an enzymatic route, as well as in the synthesis of monoacylglycerols of polyunsaturated fatty acids of theType: GrantFiled: March 13, 1998Date of Patent: March 25, 2003Inventor: Gildas Breton
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Patent number: 6489496Abstract: The present invention pertains to a process for making an alkyl ester of a carboxylic acid via transesterification comprising the steps of: (1) reacting a carboxylic acid ester with an alcohol and an effective amount of a transesterification catalyst in a reaction zone to form a reaction mixture comprised of a product ester and a product alcohol; (2) passing the reaction mixture from step (1) through a centrifugal separation zone wherein the second alcohol is separated from the second ester. The process according to the invention allows for shorter reaction times and improved product yields.Type: GrantFiled: June 26, 2001Date of Patent: December 3, 2002Assignee: Cognis CorporationInventors: Jeffrey A. Barnhorst, Michael D. Staley, Dean A. Oester
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Patent number: 6407269Abstract: The present invention provides a heterogeneous catalyst which is highly active, excellent in selectivity and free from elution of its catalyst-components during reaction and which has long lifetime. That is, a phosphate of a metal selected from the group consisting of aluminum, gallium and iron is used as the catalyst for transesterification of the present invention.Type: GrantFiled: June 22, 2001Date of Patent: June 18, 2002Assignee: Kao CorporationInventors: Jun Kaita, Taku Mimura, Noriaki Fukuoka, Yasuyuki Hattori
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Patent number: 6359157Abstract: A process for the transesterification of fat and/or oil of biological origin by means of alcoholysis comprises the following steps: provision in a vessel of fat and/or oil of biological origin to be transesterified, and implementation of alcoholysis by addition of an alkanol, in particular of a monohydric alkanol, and of a catalyst to the fat and/or oil that has been provided. with a view to eliminating the disadvantages of traditional transesterification processes, a metal salt of an amino acid or of an amino-acid derivative is used as catalyst, said metal salt being insoluble in alkanols.Type: GrantFiled: June 19, 2001Date of Patent: March 19, 2002Inventors: Siegfried Peter, Eckhard Weidner, Hans-Peter Neuner, Ruth Ganswindt
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Patent number: 6288251Abstract: Provided is a process for producing a fatty acid alkylester through a transesterification of triglyceride contained in a fat and oil by causing the fat and oil and an alcohol to react with each other. In this process, the reaction is performed in an atmosphere in which the alcohol is in super-critical state in the absence of a metal alkali catalyst and an acid catalyst. This makes it possible to eliminate a pre-treatment process for esterifying free fatty acids contained in the fat and oil and, in addition, to eliminate or simplify recovering and refining processes of the reaction product by suppressing the by-production of a fatty acid soap.Type: GrantFiled: August 14, 2000Date of Patent: September 11, 2001Assignee: Lonford Development LimitedInventors: Keiichi Tsuto, Guo-Tang Liu
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Patent number: 6278006Abstract: Oils containing a triacylglycerol polyol ester and a non-glycerol polyol ester are described, as well as methods of making such oils. Methods for improving lubrication properties of a vegetable oil also are described.Type: GrantFiled: January 19, 1999Date of Patent: August 21, 2001Assignee: Cargill, IncorporatedInventors: Dharma R. Kodali, Scott C. Nivens
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Patent number: 6274750Abstract: Mixtures of dimeric and trimeric fatty acid C1-4 alkyl esters and processes for their preparation comprising either A) epoxidizing an unsaturated or partially hydrogenated fatty acid glyceride; B) transesterifying the epoxidized glyceride with a C1-4 alkanol to obtain epoxidized fatty acid C1-4 alkyl esters; and C) ring opening and dimerizing the epoxidized fatty acid C1-4 alkyl esters; or A) transesterifying an unsaturated or partially hydrogenated glyceride with a C1-4 alkanol to obtain olefinically unsaturated fatty acid C1-4 alkyl esters; B) epoxidizing the unsaturated fatty acid C1-4 alkyl esters; and C) ring opening and dimerizing the epoxidized fatty acid C1-4 alkyl esters.Type: GrantFiled: July 21, 1998Date of Patent: August 14, 2001Assignee: Cognis CorporationInventors: Setsuo Sato, Ramiro Carielo Bueno, Wanderson Bueno De Almeida
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Patent number: 6268010Abstract: Reduced calorie fat mimetics comprising fatty acid-esterified alkoxylated polyol compositions having an average number of oxyalkylene groups per molecule of no more than 5 and from 5 percent to 39 percent primary hydroxyl groups based on the total amount of hydroxyl groups on the molecule. These reduced calorie fat mimetics are prepared by alkoxylating a polyol such that the average number of oxyalkylene groups per molecule is no more than 5, and subsequently esterifying with fatty acids. The reduced calorie fat mimetics can be synthesized to mimic the properties of the natural fats which are replaced in numerous food products. The fat mimetics are partially digestible thus obviating undesirable gastrointestinal side effects.Type: GrantFiled: June 15, 1999Date of Patent: July 31, 2001Assignee: BestfoodsInventor: Bernard Charles Sekula
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Patent number: 6262285Abstract: A continuous separation of fatty acid methyl esters (FAME) from glycerol in a low pressure dry transesterification process for vegetable oil is provided. Improved purity of the FAME and the glycerol fractions are achieved via the use of continuous decantation so as to thereby eliminate the need for a water wash step for the FAME fraction. Excess methanol from the FAME and the glycerol fractions is readily recovered in a dry vacuum extraction process. Water which has been inadvertently introduced into the process is removed from the recovered excess methanol by desiccant columns equipped with molecular sieves instead of the traditional energy and capital intensive fractionation processes practiced for this purpose.Type: GrantFiled: June 24, 1999Date of Patent: July 17, 2001Assignee: Crown Iron Works CompanyInventor: William M. McDonald
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Patent number: 6211390Abstract: The invention concerns a method for producing fatty acid esters from fatty acid triglyceride and in particular from animal or vegetable fats and oils by transesterification with a monovalent low-molecular weight alcohol in the presence of a homogeneous or heterogeneous catalyst. In accordance with the invention, the formed fatty acid ester is extracted from the reaction mixture by means of a near-critical extractant. In this way fatty acid esters are obtained at high yield and excellent purity. As the extractant preferably a low pressure gas having a reduced temperature at 20° C. of about 0.7, preferably of equal to or greater than 0.7, is employed. Preferred extractants are carbon dioxide, propane, butane, dimethyl ether, ethyl acetate or mixtures thereof.Type: GrantFiled: December 3, 1999Date of Patent: April 3, 2001Inventors: Siegfried Peter, Ruth Ganswindt, Eckhard Weidner
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Patent number: 6187939Abstract: Fatty acid esters, which are prepared by reacting fats and oils with an alcohol in the absence of a catalyst under a condition under which at least one of the fats and oils and the alcohol is in a supercritical state, are useful as fuels such as diesel fuels, lubrication base oils or fuel additives.Type: GrantFiled: September 9, 1999Date of Patent: February 13, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Toshio Sasaki, Tomoyuki Suzuki, Fumio Okada
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Patent number: 6177580Abstract: A process for making synthetic triglycerides involving: (a) providing a reaction component selected from the group consisting of glycerol, a triglyceride, and mixtures thereof; (b) providing a fatty acid mixture containing at least 50% by weight, based on the weight of the fatty acid mixture, of conjugated linoleic acid; (c) providing an inert gas atmosphere; (d) combining the reaction component with the fatty acid mixture, in the inert atmosphere, to form a reaction mixture; and (e) heating the reaction mixture to a temperature of from 180 to 240° C., at a heating rate of from 0.5 to 3 K per minute, thus forming the synthetic triglyceride.Type: GrantFiled: October 29, 1999Date of Patent: January 23, 2001Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Franz Timmermann, Rolf Gaupp, Juergen Gierke, Rainer Von Kries, Wolfgang Adams, Andreas Sander
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Patent number: 6153773Abstract: A method of preparing purified ester compositions is provided. The process can be utilized to isolate and purify monoglycerides and propylene glycol monoesters, to advantage. It can also be used to isolate preferred diester products. The invention also concerns equipment for conduct of the processes, provision of preferred food additives, and provision of preferred food industry compositions. The process generally involves use of liquid-liquid extractions, to advantage.Type: GrantFiled: June 30, 1999Date of Patent: November 28, 2000Assignee: Cargill, IncorporatedInventors: Jeffrey J. Kolstad, Richard D. Benson, Scott D. Bloomer, Paraskevas Tsobanakis
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Patent number: 6127560Abstract: Comminuted soybeans are heated to high temperatures to condition the soybean oil contained therein. The soybean oil is extracted and filtered to remove solid fines, and then degummed and bleached. The prepared oil is introduced into a stirred reactor where lower aliphatic monohydric alcohol and an alkaline catalyst is introduced. Alcoholysis proceeds to virtual completion. A lower alkyl alcohol ester phase is separated out and washed with water to remove traces of unreacted alcohol and the alkaline catalyst.Type: GrantFiled: December 29, 1998Date of Patent: October 3, 2000Assignee: West Central CooperativeInventors: William D. Stidham, Donald W. Seaman, Myron F. Danzer
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Patent number: 6127561Abstract: The invention discloses a process for the production of monoglycerides by glycerolysis of methyl ester derived from animal or vegetable fat and oils which includes mixing a surplus of 0.1 to 3 moles of glycerols in relation to methyl ester, subjecting the reaction mixture to a reaction temperature between 130 to 160 at a vacuum of 200 to 400 mbar, adding of alkaline catalysts, stopping the reaction by fast cooling of the reaction mixture and the destruction of the alkaline catalyst when the quantity of glycerides has reached a concentration of mono and diglyceride of 40 to 60%, leaving the catalyst in the reaction mixture to catalyse the reaction downstream in a reactor, separating the surplus methyl ester and glycerol by distillation and stopping the reaction by fast cooling of the reaction mixture with reactor and the destruction of the alkaline catalyst when the quantity of glycerides has reached a concentration of 40 to 60% and the ratio of concentrations of mono and diglyceride lies between 3 to 10.Type: GrantFiled: December 12, 1997Date of Patent: October 3, 2000Assignees: Global Palm Products SDN. BHD., Johor Darul TakzimInventors: Lutz Jeromin, Guenter Wozny, Pu Li
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Patent number: 6124486Abstract: The specification discloses a process for making low calorie triglycerides. The process involves interesterifying short triglycerides having C.sub.2 to C.sub.10 fatty acid chains and long triglycerides having C.sub.16 to C.sub.24 fatty acid chains in the presence of a catalyst and without a solvent to produce low calorie triglycerides as an interesterification product of the long and short triglycerides comprising individual triglycerides wherein a substantial is portion of the low calorie triglycerides have two long C.sub.16 to C.sub.24 fatty acid chains and one short C.sub.2 to C.sub.10 fatty acid chain having at least one long C.sub.16 to C.sub.24 fatty acid chain and at least one short C.sub.2 to C.sub.10 fatty acid chain. The process enables continuous production of low calorie triglycerides with recycle of catalyst and unreacted starting materials for an economical mode of operation with improved product yield and quality.Type: GrantFiled: January 31, 1997Date of Patent: September 26, 2000Assignee: Eastman Chemical CompanyInventors: Daniel Eric Cherwin, James William Johnson, Jr.
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Patent number: 6107500Abstract: A process for the preparation of mixtures which comprise mostly sorbitol monoesters, sorbitol diesters and partial glycerides, sorbitol being reacted with triglycerides in the presence of at least one alkaline catalyst, is described, wherein the cocatalyst used for the reaction is:a) a part amount of the product of the above reaction as a self-emulsifier and/orb) an amidoamine of the following formula (I) ##STR1## in which in which: R.sup.1 is an alkyl or alkenyl group having 6 to 13 carbon atoms, R.sup.2 is an alkyl group having 1 to 6 carbon atoms or an H atom, R.sup.3 is an alkyl group having 1 to 6 carbon atoms and n is a number from 1 to 6. The novel process gives purer products and leads to a considerably improved space/time yield.Type: GrantFiled: June 30, 1998Date of Patent: August 22, 2000Assignee: Clariant GmbHInventors: Gunter Prossel, Bernd Papenfuhs
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Patent number: 6090959Abstract: In a method of producing a fatty acid lower alkylester according to the invention, a fat & oil and a lower alcohol are caused to react with each other in the presence of a catalyst, in which triglyceride contained in the fat & oil undergoes a transesterification. The catalyst to be used in the reaction is a solid basic catalyst consisting essentially of a potassium compound and iron oxide, of a calcium compound and iron oxide, or of a potassium compound and zirconium oxide. It is possible to produce the fatty acid lower alkylester at a high reaction efficiency by this method as well as to simplify or eliminate the need of catalyst separation and recovery processes.Type: GrantFiled: September 3, 1998Date of Patent: July 18, 2000Assignee: Lonford Development LimitedInventors: Takenori Hirano, Keiichi Tsuto
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Patent number: 6072064Abstract: The invention relates to a process for the catalytic interesterification of triglycerides, which is characterized in that a heterogeneous catalyst is used, based on one or more oxides and/or oxysalts of metals of the groups IA and IIA of the Periodic System, at least one of the oxides and/or oxysalts having an optical basicity .LAMBDA. which is at least 0.5.Type: GrantFiled: June 5, 1996Date of Patent: June 6, 2000Assignee: Engelhard CorporationInventors: Cornelis Roeland Bayense, Bernard Hendrik Reesink, Pieter Hildegardus Berben
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Patent number: 6069261Abstract: A process carried out in a reaction column for the chemical reaction of substances the reaction of which is affected by an unfavorable equilibrium position of the main reaction or a preceding equilibrium, wherein during the reaction one or more substances to be separated are continuously removed from the reaction mixture by one or more auxiliaries.Type: GrantFiled: May 4, 1998Date of Patent: May 30, 2000Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und ChemieInventors: Ulrich Hoffmann, Ulrich Kunz
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Patent number: 6063946Abstract: This invention relates to a process for the isolation of fatty acids and fatty acid esters from complex naturally occurring mixtures which contain sterols, triglycerides and phospholipids.Type: GrantFiled: January 26, 1996Date of Patent: May 16, 2000Assignee: Eastman Chemical CompanyInventors: Robert Alan Miller, Terrence Bruce Mazer, Scott Donald Barnicki, Charles Edwan Sumner, Jr.
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Patent number: 6004611Abstract: The present invention provides a general-purpose edible oils composition which can prevent an increase of the blood triglyceride level of a person having eaten, is little accumulated in the body, and is excellent in storage stability and flavor. A general-purpose liquid oils composition which comprises oils containing 1,3-diglycerides in an amount of 40% by weight or above and monoglycerides in an amount of less than 1.5% by weight, with unsaturated fatty acids accounting for at least 93% by weight of the fatty acid components constituting the diglycerides.Type: GrantFiled: October 2, 1997Date of Patent: December 21, 1999Assignee: Kao CorporationInventors: Naohiro Gotoh, Hiroyuki Watanabe, Tsutomu Nishide, Takuji Yasukawa
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Patent number: 5986117Abstract: A convenient method of obtaining useful esterified propoxylated glycerin fat substitutes from readily available triglycerides such as fats and oil is provided wherein a triglyceride is reacted with a propoxylated glycerin under conditions effective to remove glycerin during such reaction.Type: GrantFiled: June 18, 1997Date of Patent: November 16, 1999Assignee: Arco Chemical Technology, L.P.Inventor: Charles F. Cooper
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Patent number: 5986119Abstract: The present invention relates to a series of "reconstituted castor oils". The term reconstituted as used hereon refers to a process in which castor oil and one or more oils of natural origin are transesterified under conditions of high temperature and catalyst to make a "reconstituted product" having an altered alkyl distribution and consequently altered chemical and physical properties.Type: GrantFiled: December 24, 1997Date of Patent: November 16, 1999Assignee: Hansotech Inc.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5885946Abstract: The object of the invention is a process for preparing a synthetic ester from a vegetable oil by a two-stage transesterification process. Further objects of the invention are lubricants containing a synthetic ester prepared by the process according to the invention.Type: GrantFiled: March 4, 1997Date of Patent: March 23, 1999Assignee: Raision Tehtaat Oy AbInventor: Merja Lamsa
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Patent number: 5883273Abstract: Fatty acid esters such as those containing arachidonic acid (AA) and docosahexaenoic acid (DHA) derived from lipid mixtures are prepared with reduced levels of sterols and phosphorus. A preferred embodiment of the invention comprises extracting lipids from egg with methanol; separating lipids including sterols from insoluble egg components; submitting the methanolic solution of lipids to transesterification and subsequent neutralization to convert the lipids to methyl esters of said free fatty acids together with sterols; separating the said sterols and esters from an aqueous phase including phosphorus compounds formed in the transesterification; subjecting the said fatty acid esters and sterols to distillation to separate sterols from the fatty acid esters; and subjecting the said esters to transesterification in the presence of glycerol to produce triglycerides of said esters thereof including that of AA and DHA wherein the resulting triglycerides contain reduced quantities of sterols and phosphorus.Type: GrantFiled: January 26, 1996Date of Patent: March 16, 1999Assignee: Abbott LaboratoriesInventors: Robert Alan Miller, Terrence Bruce Mazer, Charles Allan McCombs
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Patent number: 5872269Abstract: Economics of heat are achieved in a process for batch fatty acid esterification of alkoxylated polyol by transferring the reaction mixture to a holding vessel and subsequently heating fresh feed to the batch reaction by indirect heat exchange with the transferred reaction mixture.Type: GrantFiled: May 8, 1998Date of Patent: February 16, 1999Assignee: Arco Chemical Technology, L.P.Inventor: Gary A. Sawyer
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Patent number: 5849939Abstract: A method for the preparation of fatty acid alkyl esters by transesterification, in particular catalytic transesterification, of triglycerides, wherein from a reaction mixture, in which the transesterification is carried out, an ester phase and a glycerol phase containing fatty acids, fatty acid salts and/or other fatty acid compounds are formed, which are separated from each other, characterized in that the fatty acids, the fatty acid salts and/or other fatty acid compounds are separated from the glycerol phase, esterified with an alcohol and recycled to a different reaction mixture, in which a further transesterification is carried out. The method according to the invention allows for a transesterification with a high yield of fatty acid esters.Type: GrantFiled: February 27, 1996Date of Patent: December 15, 1998Assignees: Martin Mittelbach, Michael Koncar, Vogel & Noot Industrieanlagenbau Gesellschaft m.b.H.Inventors: Martin Mittelbach, Michael Koncar
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Patent number: 5844111Abstract: A process for purifying an inert gas stream from a transesterification reaction wherein a lower alkyl alcohol is released during the reaction is claimed. A second use of the process is to make a lower alkyl, e.g., methyl, esters of fatty acids through a transesterification reaction using gaseous alcohols as a source of the lower alkyl alcohols. The alcohol is diluted with nitrogen or other inert gas carrier and reacted with a fatty acid ester, preferably a triglyceride, to form the corresponding methyl or lower alkyl fatty acid ester.Type: GrantFiled: June 7, 1995Date of Patent: December 1, 1998Assignee: The Procter & Gamble CompanyInventors: Eric Paul Granberg, Richard Gerard Schafermeyer, James Anthony Letton
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Patent number: 5773636Abstract: A process for the production of fatty acid lower alkyl esters comprising the steps of:A) treating at least one fatty acid ester of glycerol with from about 0.3 to about 3% by weight, based on the weight of ester, of an acid at an elevated temperature;B) removing said acid from the treated fatty acid ester; andC) reacting the treated fatty acid ester with at least one lower aliphatic alcohol to transesterify the fatty acid ester.Type: GrantFiled: August 5, 1996Date of Patent: June 30, 1998Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Guenther Demmering, Christian Pelzer, Lothar Friesenhagen
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Patent number: 5597934Abstract: The preparation of polyol compounds by (a) condensing glycerine in the presence of lithium compounds; (b) continuously distilling off the water produced by the reaction; (c) optionally subjecting the oligoglycerine mixture obtained to a transesterification reaction with fatty-acid glyceride esters. Such polyol compounds are suitable for use as starting materials in the production of polymers.Type: GrantFiled: June 7, 1995Date of Patent: January 28, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Johann Klein, Peter Daute, Udo Hees, Bernd Beuer
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Patent number: 5532392Abstract: A process for the preparation of methyl fatty acid esters starting from natural oil or fat by transesterification with methanol in the presence of a catalyst of an organotitanate based catalyst, in particular of tetrabutyl orthotitanate, methyl esters as obtained in this way and use thereof as fuel.Type: GrantFiled: January 13, 1994Date of Patent: July 2, 1996Inventor: Mihail Gheorghiu
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Patent number: 5508457Abstract: 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: GrantFiled: May 3, 1994Date of Patent: April 16, 1996Assignees: Engelhard De Meern B.V., Fina Research S.A.Inventors: Cornelis R. Bayense, Herve Hinnekens, Julien Martens
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Patent number: 5508048Abstract: High erucic cruciferae oils are interesterified with C.sub.16 or higher fatty acids or derivatives thereof. The use of a 1,3-selective lipase leads to the introduction of the fatty acid groups in the 1,3-positions. The liberated erucic acid (derivative) can be hydrogenated; the behenyl acid (or derivative) thus formed can be recirculated to provide at least 50% of the behenyl acid (derivative) needed in the process. The products obtainable by these processes, display good anti-blooming properties.Type: GrantFiled: January 7, 1994Date of Patent: April 16, 1996Assignee: Van Den Bergh Foods Co.Inventor: Frederick B. Padley
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Patent number: 5504231Abstract: The present invention relates to a process for preparing reduced calorie triglycerides which contain short or medium chain and long chain fatty acids, but which nevertheless contain low levels of difatty ketones. The process of the present invention comprises the step of adding glycerine to a crude reaction product after a selective esterification reaction of a monoglyceride with short or medium chain fatty acids fatty acids. The glycerin is typically added at a level of from about 0.1 to about 1.0% at a reaction temperature of from about 170.degree. C. to about 215.degree. C. The contact time is about 1 to about 15 minutes. The reduced calorie triglycerides prepared according to this process will contain less than about 100 ppm difatty ketones.Type: GrantFiled: September 16, 1994Date of Patent: April 2, 1996Assignee: The Procter & Gamble CompanyInventor: Gerald J. Guskey
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Patent number: 5468887Abstract: A method of preparing esters and water soluble soaps using intensive mixing. The esters are prepared by reacting fats & oils with methanol containing caustic as a catalyst wherein the glycerin formed is removed. The resulting esters are saponified with caustic along with an additional amount of methanol to form the soap.Type: GrantFiled: March 13, 1992Date of Patent: November 21, 1995Assignee: The Dial Corp.Inventor: Shyam K. Gupta