Another Reactant Contains Alcoholic Or Phenolic Hydroxy (e.g., Methy Ricinoleate, Etc.) Patents (Class 554/167)
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Patent number: 6271405Abstract: The present invention provides a method for preparing betulin-3-acetate including alcoholyzing betulin 3,28-dibenzoate; a process for preparing betulin-3-acetate including: (1) acylating betulin to provide betulin 3,28-dibenzoate and (2) alcoholyzing betulin 3,28-dibenzoate to provide betulin-3-acetate; and a process for preparing betulinic acid including: (1) acylating betulin to provide betulin 3,28-dibenzoate; (2) alcoholyzing betulin 3,28-dibenzoate to provide betulin-3-acetate; (3) oxidizing betulin-3-acetate to provide betulinic aldehyde-3-acetate; (4) oxidizing betulinic aldehyde-3-acetate to provide betulinic acid-3-acetate; and (5) deprotecting betulinic acid-3 -acetate to provide betulinic acid.Type: GrantFiled: January 16, 2001Date of Patent: August 7, 2001Assignees: Regents of the University of Minnesota, Naturtek, LLCInventors: Pavel A. Krasutsky, Robert M. Carlson, Vitaliy V. Nesterenko
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Patent number: 6232481Abstract: The present invention provides a method for preparing betulin-3-acetate including alcoholyzing betulin 3,28-dibenzoate; a process for preparing betulin-3-acetate including: (1) acylating betulin to provide betulin 3,28-dibenzoate and (2) alcoholyzing betulin 3,28-dibenzoate to provide betulin-3-acetate; and a process for preparing betulinic acid including: (1) acylating betulin to provide betulin 3,28-dibenzoate; (2) alcoholyzing betulin 3,28-dibenzoate to provide betulin-3-acetate; (3) oxidizing betulin-3-acetate to provide betulinic aldehyde-3-acetate; (4) oxidizing betulinic aldehyde-3-acetate to provide betulinic acid-3-acetate; and (5) deprotecting betulinic acid-3-acetate to provide betulinic acid.Type: GrantFiled: January 11, 2000Date of Patent: May 15, 2001Assignees: Regents of the University of Minnesota, Naturtek, LLCInventors: Pavel A. Krasutsky, Robert M. Carlson, Vitaliy V. Nesterenko
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Patent number: 6229056Abstract: The proposal is for unsaturated fatty substances with improved cold behavior obtained by (a) transesterifying a new low stearic (LS) sunflower oil with an oleic acid content of over 85 wt. % and a stearic acid content of under 3 wt. %, and (b) hydrogenating the resultant methyl esters in the prior art manner into the corresponding unsaturated fatty alcohols in the iodine number range from 90 to 100. The fatty substances are also distinguished by improved color and odor and are suitable for making fatty chemical products, e.g. alkoxylates, ether sulphates, sulphates and esters.Type: GrantFiled: May 8, 1997Date of Patent: May 8, 2001Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Achim Ansmann, Guenther Demmering, Georg Assmann, Fritz Schuster, Alfred Westfechtel, Michael Koehler
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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: 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: 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: 6013817Abstract: For the production of ethyl esters of fatty acids from fatty acid glycerides such as vegetable or animal oil or fat or other mixtures of glycerides, the process comprises the following stages: (a) transesterifying fatty acid glycerides with hydrated ethyl alcohol using an alkaline catalyst to form a medium comprising ethyl esters and excess ethyl alcohol; (b) adding a glycerine phase to said medium, and evaporating the excess ethyl alcohol to produce two immiscible phases, an ester phase and a glycerine phase A, and recycling said excess ethyl alcohol to stage (a); (c) separating said glycerine phase A and said ester phase to obtain the desired ethyl esters; (d) neutralizing said glycerine phase A with acid, and separating resultant "fatty acids+esters" phase and a glycerine phase B, and drying the latter phase; (e) subjecting the "fatty acids+esters" phase to glycerolysis with at least a fraction of the dried glycerine phase B in the presence of an alkaline catalyst to form a mixture of glycerides and estersType: GrantFiled: May 7, 1997Date of Patent: January 11, 2000Assignee: Institut Francais du PetroleInventors: Robert Stern, Gerard Hillion, Mohammed Neguib Eisa
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Patent number: 6002030Abstract: A process is provided for the fatty acid esterification of propoxylated glycerin wherein fatty acids stripped from the esterifier and/or fatty acids stripped from the esterification product are scrubbed by contact with a scrubbing liquid which is maintained at a temperature above the fatty acid melting point.Type: GrantFiled: May 8, 1998Date of Patent: December 14, 1999Assignee: ARCO Chemical Technology, L.P.Inventor: Jon R. Valbert
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Patent number: 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: 5908946Abstract: For the production of linear monocarboxylic acid esters with 6 to 26 carbon atoms vegetable oils or animal oils, which may or may not be neutral, are reacted with monoalcohols having a low molecular weight, for example 1 to 5 carbon atoms, in the presence of a catalyst that is selected from among zinc oxide, mixtures of zinc oxide and aluminum oxide, and the zinc aluminates that correspond to the formula:ZnAl.sub.2 O.sub.4, x ZnO, y Al.sub.2 O.sub.3(with x and y each being in the range of 0-2) and having more particularly a spinel type structure, thereby enabling the direct production in one or more stages, of an ester that can be used as a fuel or combustible and a pure glycerine.Type: GrantFiled: August 8, 1997Date of Patent: June 1, 1999Assignee: Institut Francais du PetroleInventors: Robert Stern, Gerard Hillion, Jean-Jacques Rouxel, Serge Leporq
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Patent number: 5898077Abstract: The present invention provides a process for preparing an ester comprising the step of reacting a carboxylic acid and an alcohol in the presence of an esterifying catalyst comprising at least one compound having the formula:O.dbd.M(RCOO).sub.2 wherein M represents Sn or Zn and R represents a saturated or unsaturated hydrocarbon group having 1-21 carbon atoms with or without side chains. According to the present process, substantially equal equivalents of the alcohol and the acid can be reacted completely. In addition, the present invention further provides a purification process to eliminate the catalyst from a homogeneous reaction system completely.Type: GrantFiled: October 7, 1997Date of Patent: April 27, 1999Assignee: Matsumoto Yushi-Seiyaku Co., Ltd.Inventors: Ichiro Takahara, Masumi Kadobayashi, Noriaki Kaminaka
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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: 5874643Abstract: Fatty alcohol containing admixed therewith a small amount on the order of up to 1.0 wt. % of hypophosphorous acid, exhibits markedly reduced oxidation and oxidation-related deterioration such as discoloration and other side effects. This discovery is particularly useful when the fatty alcohol is subjected to reactions such as esterification under conditions which could cause or accelerate undesired oxidation.Type: GrantFiled: December 1, 1995Date of Patent: February 23, 1999Assignee: Witco CorporationInventors: Garrett Mineo, Michael Denoux
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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: 5710296Abstract: A method for preparing phenyl esters in high yields under mild reaction conditions is provided. Particularly preferred phenyl esters prepared in accordance with the inventive method are alkanyloxy-benzene compounds having a C.sub.2-18 alkyl. The method is practiced by reacting a carboxylic acid with an acid halide either in the presence of or followed by the addition of a phenol.Type: GrantFiled: May 25, 1995Date of Patent: January 20, 1998Assignee: The Clorox CompanyInventors: LaFayette D. Foland, Thomas B. Ottoboni
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Patent number: 5679809Abstract: A composition concentrated in ethyl esters of polyunsaturated fatty acids is prepared by mixing a refined oil rich in polyunsaturated fatty acids with ethanol in the presence of a catalyst to obtain an ethanolyzate containing a glycerol phase and fatty acid ethyl ester phase. The fatty acid ethyl ester phase is separated from the glycerol phase and mixed with urea and ethanol to form a mixture, which is cooled to form a liquid phase containing fatty acid ethyl esters and a solid phase containing insoluble inclusion complexes. The liquid phase is separated from the solid phase to obtain a fraction enriched in ethyl esters of polyunsaturated fatty acids.Type: GrantFiled: April 6, 1995Date of Patent: October 21, 1997Assignee: Nestec S.A.Inventors: Constantin Bertoli, Rene Fumeaux, Marie-Claude Perrenoud Ferreira, Junkuan Wang
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Patent number: 5648483Abstract: Polyol polyesters can be made by a transesterification reaction of a polyol with a lower alkyl fatty acid ester. A by product of that reaction are the alcohols from the lower alkyl esters. These are usually removed from the transesterification reaction by inert gas stripping. The process herein links the transesterification reaction with a lower alkyl ester formation reaction. The transesterification reaction acts as a the source of the lower alkyl alcohols for the formation of the lower alkyl esters used in the polyol fatty acid polyester synthesis. A preferred method for both reactions uses a reactive absorption column.Type: GrantFiled: June 7, 1995Date of Patent: July 15, 1997Assignee: The Procter & Gamble CompanyInventors: Eric Paul Granberg, Richard Gerard Schafermeyer, James Anthony Letton
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Patent number: 5639791Abstract: The present invention deals with the utilization of certain novel di-guerbet esters which are prepared by the reaction of a guerbet alcohol and a guerbet acid in personal care applications. These esters provide lubrication, solvent and dry feel attributes to personal care applications.Type: GrantFiled: October 26, 1995Date of Patent: June 17, 1997Assignee: Siltech IncInventor: Anthony J. O'Lenick, Jr.
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Patent number: 5571935Abstract: Esterified alkoxylated polyols, particularly a fatty acid-esterified propoxylated glycerol, which exhibit improved flavor and oxidative stability by the addition of antioxidants to the alkoxylated polyols, either prior to or subsequent to steam stripping, fatty acids or combinations thereof prior to fatty acid esterification, and the products thereof.Type: GrantFiled: January 14, 1994Date of Patent: November 5, 1996Assignee: CPC International Inc.Inventors: Bernard C. Sekula, Thaddeus R. Ziegert, Michael R. Ferenz
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Patent number: 5539135Abstract: Hydrophobicized double-layer hydroxide compounds may be produced if double-layer hydroxide compounds of the general formula (I): [M.sup.(II).sub.1-x M.sup.(III).sub.x (OH).sub.2 ] A.sub.x.n H.sub.2 O, in which M.sup.(II) is a divalent metal cation, M.sup.(III) is a trivalent metal cation, A is an equivalent of a monobasic and/or multibasic inorganic acid, x is a number from 0.2 to 0.5 and n is a number from 0 to 10, are reacted at elevated temperature and under autogenous pressure with at least one carboxylic acid or its salt and the reaction product is then dried. The hydrophobicized double-layer hydroxide compounds obtained by this process are suitable as catalysts for the alkoxylation of compounds with active hydrogen atoms or of fatty acid esters.Type: GrantFiled: October 4, 1993Date of Patent: July 23, 1996Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Wolfgang Breuer, Claudia Mai, Hans-Christian Raths, Elvira Scholz
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Patent number: 5536856Abstract: Esterification is carried out in a column reactor (14) in which there is a plurality of esterification trays (15) each having predetermined liquid hold-up and containing a charge of a solid esterification catalyst thereon. e.g. an ion exchange resin containing a --SO.sub.3 H and/or --COOH groups. A liquid phase containing the carboxylic acid component, e.g. a fatty acid mixture, flows down the column reactor from one esterification tray to the next downward one against an upflowing alcohol vapour stream, e.g. methanol vapour. Relatively dry alcohol vapour is injected (21) into the bottom of the column reactor. Water of esterification is removed from the top of the column reactor in the vapour stream (26), whilst ester product is recovered (23) from the sump of the reactor. As the liquid flows down the trays it encounters progressively drier alocohol and the esterification equilibrium reaction is driven further and further towards 100% ester formation.Type: GrantFiled: February 23, 1994Date of Patent: July 16, 1996Assignee: Davy Process Technology LimitedInventors: George E. Harrison, John Scarlett, Michael A. Wood, Donald H. McKinley
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Patent number: 5532393Abstract: The wax ester is prepared from a liquid mixture which contains at least one fatty acid and at least one fatty alcohol. The fatty acid and the fatty alcohol contain 6 to 30 carbon atoms per molecule. The mixture is agitated at temperatures in the range from about 105.degree.to 300.degree. C. and is sprayed into a spraying zone. An atmosphere which contains water vapor is formed in the spraying zone and is removed at least in part. The mixture of fatty acid and fatty alcohol may be agitated in at least one stirred vessel preceding the spraying zone. A catalyst is preferably not added.Type: GrantFiled: December 16, 1994Date of Patent: July 2, 1996Assignee: Metallgesellschaft AktiengesellschaftInventors: Eberhard Schlichting, Henning Buchold, Gerd Mallok, Fritz-Jurgen Gartner, Hans-Martin Stonner
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Patent number: 5525126Abstract: The present invention includes a process for producing esters from a feedstock that includes a fat or an oil. The process includes mixing the feedstock with an alcohol and a catalyst. The catalyst includes a mixture of calcium acetate and barium acetate The reaction mixture is heated at a temperature effective to make esters.Type: GrantFiled: October 31, 1994Date of Patent: June 11, 1996Assignee: Agricultural Utilization Research InstituteInventors: Hemendra N. Basu, Max E. Norris
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Patent number: 5514820Abstract: The invention relates to a continuous process for the production of lower alkyl esters at temperatures of up to 100.degree. C. and under pressures of up to 10 bar by reaction of fatty acid triglycerides containing less than 1% free fatty acid with a lower alcohol in two stages in the presence of a homogeneous alkaline catalyst, the glycerol formed being removed after the first stage. To enable the process to be carried out with high yields and with lower maintenance, investment and energy costs than in the prior art, the reaction mixture is passed through a reactor and a following static separator only once in each stage, tube reactors are used as the reactors and the Reynolds number of the flow of the reaction mixture is greater than 2,300.Type: GrantFiled: February 3, 1994Date of Patent: May 7, 1996Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Georg Assmann, Gerhard Blasey, Bernhard Gutsche, Lutz Jeromin, Jean Rigal, Rene Armengaud, Bernard Cormary
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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: 5488121Abstract: The present invention deals with the certain novel di-guerbet esters which are prepared by the reaction of a guerbet alcohol and a guerbet acid. These materials are useful as lubricating oils where outstanding liquidity, resistance to oxidation, and minimal variation in viscosity as a function of temperature is required. This combination of properties make these compounds excellent candidates as additives to synthetic lubricating oil and extreme pressure additives.Type: GrantFiled: October 31, 1994Date of Patent: January 30, 1996Assignee: Siltech Inc.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5473089Abstract: Ammonium fatty acid hydroxyalkanesulfonates are made by a process in which (a) ammonium hydroxyalkanesulfonate corresponding to general formula (I):HO--(C.sub.n H.sub.2n)--SO.sub.3 NH.sub.4 (I)wherein n=2 to 4, is subjected to the esterification reaction with a fatty acid corresponding to the formula (II)R--COOH (II)wherein RCO is an aliphatic, linear or branched acyl radical containing 6 to 18 carbon atoms, in the presence of an esterification catalyst, characterized in that (a) before the esterification reaction, the starting compounds corresponding to formulae (I) and (II) are dried at a temperature of 120.degree. C. to 160.degree. C. and under a pressure of 100 to 700 mbar; (b) the esterification reaction is carried out at a temperature above 160.degree. C. to 195.degree. C. and under a pressure of 250 mbar to atmospheric pressure; (c) water of solution and water of reaction formed are directly removed from the reaction mixture; (d) the catalyst is neutralized with a base on completion of the reaction.Type: GrantFiled: April 14, 1994Date of Patent: December 5, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Bernhard Gutsche, Timothy J. Cassady, Lutz Jeromin, Gerhard Wollmann, Norman Milstein, Hans-Christian Raths
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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
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Patent number: 5442081Abstract: Process for the production of oligomeric fatty acids and lower alkyl esters thereof in which fatty acids containing 16 to 24 carbon atoms and 2, 3, 4 or 5 double bonds and/or lower alkyl esters thereof are oligomerized with C.sub.1-4 alcohols at an elevated temperature in the presence of a tin halide catalyst, optionally in combination with a halide of titanium, iron, cobalt, nickel, lead, and/or germanium.Type: GrantFiled: October 4, 1993Date of Patent: August 15, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Arno Behr, Hans-Peter Handwerk
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Patent number: 5434279Abstract: A process is disclosed for preparing fatty acid esters of short-chain monohydric aliphatic alcohols or monoalkylated diols by basically catalyzed esterification of natural, partially or totally synthetic fatty acid glycerides, as well as fatty acid glyceride-based waste products, such as used frying oils. The process is characterized in that the unpurified fatty acid glycerides, containing in particular high proportions of free fatty acids and phosphatides, (a) are esterified in one or several steps in the presence of a basic catalyst with an excess of short-chain alcohol or monoalkylated diol; (b) the glycerin phase produced after the first esterification step is at least partially added to the second or following step, after sterification has been carried out, and the mixture is stirred; (c) the glycerin phase is again separated, the supernatant fatty acid ester is cleared of excess alcohol or diol, then treated with a possibly diluted organic or anorganic acid, and if necessary filtered.Type: GrantFiled: May 6, 1994Date of Patent: July 18, 1995Inventor: Theodor Wimmer
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Patent number: 5399730Abstract: This invention relates to a purified wool fat essentially free from low molecular weight volatile acids, water soluble aliphatic alcohols and water. This purified wool fat is produced by effecting the esterification of free alcohols and fatty acid contained in the wool fat followed by solvent extraction and chromatographical purification of the extracted solvent. The purified wool fat can be used as a lubricant enhancer in lubricating oils.Type: GrantFiled: August 1, 1991Date of Patent: March 21, 1995Assignee: Development Products, Inc.Inventors: Boris I. Koupchinov, Viktor P. Parkalov, Vladimir G. Rodnenkov, Sergey F. Ermakov, Vitaly G. Tischenco, Lenoid A. Sarkisov, Feliks E. Gulijaev, Vladimir N. Kestelman, Anatoly I. Sviridenok
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Patent number: 5399731Abstract: The invention relates to a process for the production of the fatty acid esters of lower monovalent alcohols by transesterification of fatty acid glycerides in the presence of basic catalysts. The process according to the invention is characterized in that the transesterification is carried out in the presence of 0.025 to 0.045 mols of an alkali or alkaline earth metal compound, preferably sodium hydroxide, potassium hydroxide, sodium or potassium alcoholate, based on 100 g of fatty acid glyceride and the subsequent purification of the fatty acid esters is effected by the addition of 0.3 to 3.0 percent of water by hydration and separation of the catalyst residues and other impurities.Type: GrantFiled: March 10, 1992Date of Patent: March 21, 1995Assignee: Vogel & Noot Industrieanlagenbau Gesellschaft m.b.H.Inventor: Theodor Wimmer
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Patent number: 5362894Abstract: A method of obtaining a fatty acid-esterified alkoxylated polyol useful as a reduced calorie fat substitute is provided. The method utilizes a C.sub.1 -C.sub.4 alkyl ester of a C.sub.8 -C.sub.24 fatty acid such as methyl stearate or methyl oleate and a short chain acid-esterified alkoxylated polyol such as the acetate of propoxylated glycerin as reactants.Type: GrantFiled: November 12, 1993Date of Patent: November 8, 1994Assignees: Arco Chemical Technology, L.P., CPC International, Inc.Inventors: Beth M. Handwerker, Charles F. Cooper, Bernard C. Sekula
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Patent number: 5354878Abstract: Production of lower alkyl esters of higher fatty acids from an oil phase and lower alcohols by catalytic transesterification at reaction temperatures of up to 100.degree. C.Type: GrantFiled: March 26, 1993Date of Patent: October 11, 1994Inventors: Joosten Connemann, Anton Krallmann, Erich Fischer
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Patent number: 5214172Abstract: 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: GrantFiled: May 6, 1991Date of Patent: May 25, 1993Assignee: Air Products and Chemicals, Inc.Inventor: Francis J. Waller
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Patent number: 5210227Abstract: Compounds of formula I, ##STR1## wherein R.sup.1 represents H, OH, protected OH or alkoxy; R.sup.2 represents H; R.sup.3 represents O or (H,OH); R.sup.4 represents methyl, ethyl, propyl or allyl; R.sup.5 represents OH, protected OH or alkoxy; R.sup.6 represents OH; R.sup.7 represents OH, alkoxy or NR.sup.8 R.sup.9 where R.sup.8 and R.sup.9 independently represent H, alkyl or aryl; in addition, R.sup.1 and R.sup.2 may together represent a second bond between the carbon atoms to which they are attached; and R.sup.6 and R.sup.7 may together represent O; and pharmaceutically acceptable salts thereof; are useful inter alia as immunosuppressive agents. The invention also provides the novel compounds of formula I.Type: GrantFiled: February 27, 1991Date of Patent: May 11, 1993Assignees: Fisons plc, Fujisawa Pharmaceutical Company LimitedInventors: Hirokazu Tanaka, Martin E. Cooper, David K. Donald
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Patent number: 5177229Abstract: Alcohols and acids are esterified by means of liquid-phase equilibrium reactions on ion exchangers in an apparatus comprising a prereactor and a rectifying column with external reactors. The process is characterized by the fact that a portion of one of the starting compounds is fed directly to the external reactors.Type: GrantFiled: July 10, 1991Date of Patent: January 5, 1993Assignee: Huls AktiengesellschaftInventors: John Kahsnitz, Alfred Oberholz, Udo Knippenberg, Michael Zolffel
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Patent number: 5159092Abstract: An alkylene oxide is reacted in a loop reactor with an organic compound having a reactive hydrogen atom, a gas circulation and a liquid circulation around the reactor being provided and being coupled with one another via an ejector mixing nozzle. To ensure completeness of the reaction and suppression of the formation of by-products such as dioxane, it is essential to reduce the temperature of the entire alkylene oxide gas phase to a temperature below that of the liquid phase, and this is effected by feeding and evaporating liquid alkylene oxide and by cooling of the gas phase on the unit walls.Type: GrantFiled: September 12, 1990Date of Patent: October 27, 1992Assignee: Buss AGInventor: Gunter M. Leuteritz
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Patent number: 5157132Abstract: A process and apparatus is disclosed for separation of fatty acid alkyl esters, carotenoids and tocotrienols from oil. Fatty acids in a vegetable oil are subjected to alcoholic esterification to form an ester-rich layer including fatty acid alkyl esters, carotenoids and tocotrienols. The ester-rich layer is exposed to solvolytic micellization to form a carotenoid-rich layer. The ester-rich layer is separated from the carotenoid-rich layer. The carotenoids in the carotenoid-rich layer are concentrated and can be adsorptively separated from the carotenoid-rich layer. Fatty acid alkyl esters are separated from the ester-rich layer to form a tocotrienol-rich layer. Individual tocotrienols in the tocotrienol-rich layer are adsorptively separated and concentrated.Type: GrantFiled: May 18, 1990Date of Patent: October 20, 1992Assignee: Carotech AssociatesInventors: Barrie Tan, Mohammed H. Saleh
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Patent number: 5130061Abstract: A process for the extraction of eicosapentaenoic (EPA) and docosahexaenoic (DHA) acid esters from crude fish oils, by means of transesterification with ethanol and H.sub.2 SO.sub.4 and two-step molecular distillation.Type: GrantFiled: May 24, 1989Date of Patent: July 14, 1992Assignee: Innova di Ridolfi Flora & C. s.a.s.Inventors: Franco Cornieri, Walter Di Fulvio
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Patent number: 5118448Abstract: Esterified alkoxylated polyols useful as fat mimetics may be prepared by alkoxylating a benzylated polyol with an epoxide under basic conditions, reacting the benzyl ether group with hydrogen to convert it to a hydroxy group, and then esterifying with a fatty acid compound. The resulting product has at least one fatty acid ester group attached directly to the polyol residue.Type: GrantFiled: October 19, 1990Date of Patent: June 2, 1992Assignee: Arco Chemical Technology, L.P.Inventor: Charles F. Cooper
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Patent number: 5116546Abstract: The invention pertains to the production of high-purity fatty-acid lower-alkyl mono-esters which comprises a first transesterification step between glycerol fatty-acid esters and a lower alcohol, a separation step wherein the reaction product of the esterification step is separated into glycerol-rich and fatty-acid lower-alkyl mono-ester rich fractions, a second esterification step in which all glycerol and fatty-acid glycerolesters of the fatty-acid lower-alkyl mono-ester rich fraction are esterified to the corresponding fatty-acid triglycerolesters, and a recovery step wherein said fatty-acid lower-alkyl mono-esters are recovered.Type: GrantFiled: April 3, 1990Date of Patent: May 26, 1992Assignee: Van den Bergh Foods Co., Division of Conopco, Inc.Inventors: Robbert Klok, Herbert H. Verveer
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Patent number: 5110508Abstract: The invention relates to a process, more especially a discontinuous process, for conducting a reaction taking place at elevated temperature in which heat-sensitive products are formed. To increase the volume-time yield, a heat transfer unit independent of the reactor is used for heating. The invention also relates to an apparatus for the production of heat-sensitive products at elevated temperatures. This apparatus comprises a reactor and a heating system. To increase the volume-time yield, the heating system comprises at least one heat transfer unit arranged outside and connected to the reactor.Type: GrantFiled: April 20, 1989Date of Patent: May 5, 1992Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Karl-Heinz Buettgen, Bernhard Gutsche, Friedrich Hommers, Wilhelm Johannisbauer, Eberhard Peukert, Reinhold Sedelies