Another Reactant Contains Alcoholic Or Phenolic Hydroxy (e.g., Methy Ricinoleate, Etc.) Patents (Class 554/167)
  • Patent number: 6271405
    Abstract: 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: Grant
    Filed: January 16, 2001
    Date of Patent: August 7, 2001
    Assignees: Regents of the University of Minnesota, Naturtek, LLC
    Inventors: Pavel A. Krasutsky, Robert M. Carlson, Vitaliy V. Nesterenko
  • Patent number: 6232481
    Abstract: 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: Grant
    Filed: January 11, 2000
    Date of Patent: May 15, 2001
    Assignees: Regents of the University of Minnesota, Naturtek, LLC
    Inventors: Pavel A. Krasutsky, Robert M. Carlson, Vitaliy V. Nesterenko
  • Patent number: 6229056
    Abstract: 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: Grant
    Filed: May 8, 1997
    Date of Patent: May 8, 2001
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Achim Ansmann, Guenther Demmering, Georg Assmann, Fritz Schuster, Alfred Westfechtel, Michael Koehler
  • Patent number: 6127560
    Abstract: 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: Grant
    Filed: December 29, 1998
    Date of Patent: October 3, 2000
    Assignee: West Central Cooperative
    Inventors: William D. Stidham, Donald W. Seaman, Myron F. Danzer
  • Patent number: 6107500
    Abstract: 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: Grant
    Filed: June 30, 1998
    Date of Patent: August 22, 2000
    Assignee: Clariant GmbH
    Inventors: Gunter Prossel, Bernd Papenfuhs
  • Patent number: 6069261
    Abstract: 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: Grant
    Filed: May 4, 1998
    Date of Patent: May 30, 2000
    Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Ulrich Hoffmann, Ulrich Kunz
  • Patent number: 6063946
    Abstract: 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: Grant
    Filed: January 26, 1996
    Date of Patent: May 16, 2000
    Assignee: Eastman Chemical Company
    Inventors: Robert Alan Miller, Terrence Bruce Mazer, Scott Donald Barnicki, Charles Edwan Sumner, Jr.
  • Patent number: 6013817
    Abstract: 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 esters
    Type: Grant
    Filed: May 7, 1997
    Date of Patent: January 11, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Robert Stern, Gerard Hillion, Mohammed Neguib Eisa
  • Patent number: 6002030
    Abstract: A process is provided for the fatty acid esterification of propoxylated glycerin wherein fatty acids stripped from the esterifier and/or fatty acids stripped from the esterification product are scrubbed by contact with a scrubbing liquid which is maintained at a temperature above the fatty acid melting point.
    Type: Grant
    Filed: May 8, 1998
    Date of Patent: December 14, 1999
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Jon R. Valbert
  • Patent number: 5986117
    Abstract: 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: Grant
    Filed: June 18, 1997
    Date of Patent: November 16, 1999
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Charles F. Cooper
  • Patent number: 5908946
    Abstract: 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: Grant
    Filed: August 8, 1997
    Date of Patent: June 1, 1999
    Assignee: Institut Francais du Petrole
    Inventors: Robert Stern, Gerard Hillion, Jean-Jacques Rouxel, Serge Leporq
  • Patent number: 5898077
    Abstract: 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: Grant
    Filed: October 7, 1997
    Date of Patent: April 27, 1999
    Assignee: Matsumoto Yushi-Seiyaku Co., Ltd.
    Inventors: Ichiro Takahara, Masumi Kadobayashi, Noriaki Kaminaka
  • Patent number: 5885946
    Abstract: 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: Grant
    Filed: March 4, 1997
    Date of Patent: March 23, 1999
    Assignee: Raision Tehtaat Oy Ab
    Inventor: Merja Lamsa
  • Patent number: 5883273
    Abstract: 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: Grant
    Filed: January 26, 1996
    Date of Patent: March 16, 1999
    Assignee: Abbott Laboratories
    Inventors: Robert Alan Miller, Terrence Bruce Mazer, Charles Allan McCombs
  • Patent number: 5874643
    Abstract: 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: Grant
    Filed: December 1, 1995
    Date of Patent: February 23, 1999
    Assignee: Witco Corporation
    Inventors: Garrett Mineo, Michael Denoux
  • Patent number: 5872269
    Abstract: 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: Grant
    Filed: May 8, 1998
    Date of Patent: February 16, 1999
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Gary A. Sawyer
  • Patent number: 5710296
    Abstract: 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: Grant
    Filed: May 25, 1995
    Date of Patent: January 20, 1998
    Assignee: The Clorox Company
    Inventors: LaFayette D. Foland, Thomas B. Ottoboni
  • Patent number: 5679809
    Abstract: 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: Grant
    Filed: April 6, 1995
    Date of Patent: October 21, 1997
    Assignee: Nestec S.A.
    Inventors: Constantin Bertoli, Rene Fumeaux, Marie-Claude Perrenoud Ferreira, Junkuan Wang
  • Patent number: 5648483
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: July 15, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Eric Paul Granberg, Richard Gerard Schafermeyer, James Anthony Letton
  • Patent number: 5639791
    Abstract: 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: Grant
    Filed: October 26, 1995
    Date of Patent: June 17, 1997
    Assignee: Siltech Inc
    Inventor: Anthony J. O'Lenick, Jr.
  • Patent number: 5571935
    Abstract: 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: Grant
    Filed: January 14, 1994
    Date of Patent: November 5, 1996
    Assignee: CPC International Inc.
    Inventors: Bernard C. Sekula, Thaddeus R. Ziegert, Michael R. Ferenz
  • Patent number: 5539135
    Abstract: 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: Grant
    Filed: October 4, 1993
    Date of Patent: July 23, 1996
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Wolfgang Breuer, Claudia Mai, Hans-Christian Raths, Elvira Scholz
  • Patent number: 5536856
    Abstract: 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: Grant
    Filed: February 23, 1994
    Date of Patent: July 16, 1996
    Assignee: Davy Process Technology Limited
    Inventors: George E. Harrison, John Scarlett, Michael A. Wood, Donald H. McKinley
  • Patent number: 5532393
    Abstract: 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: Grant
    Filed: December 16, 1994
    Date of Patent: July 2, 1996
    Assignee: Metallgesellschaft Aktiengesellschaft
    Inventors: Eberhard Schlichting, Henning Buchold, Gerd Mallok, Fritz-Jurgen Gartner, Hans-Martin Stonner
  • Patent number: 5525126
    Abstract: 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: Grant
    Filed: October 31, 1994
    Date of Patent: June 11, 1996
    Assignee: Agricultural Utilization Research Institute
    Inventors: Hemendra N. Basu, Max E. Norris
  • Patent number: 5514820
    Abstract: 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: Grant
    Filed: February 3, 1994
    Date of Patent: May 7, 1996
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Georg Assmann, Gerhard Blasey, Bernhard Gutsche, Lutz Jeromin, Jean Rigal, Rene Armengaud, Bernard Cormary
  • Patent number: 5508457
    Abstract: The invention is directed to a process for the transesterification of carboxylic acid esters, in which process a catalyst is used which is substantially insoluble in the reaction mixture under reaction conditions, said catalyst comprising at least one silicate of the Group IVB elements of the Periodic Table as the active component.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: April 16, 1996
    Assignees: Engelhard De Meern B.V., Fina Research S.A.
    Inventors: Cornelis R. Bayense, Herve Hinnekens, Julien Martens
  • Patent number: 5488121
    Abstract: 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: Grant
    Filed: October 31, 1994
    Date of Patent: January 30, 1996
    Assignee: Siltech Inc.
    Inventor: Anthony J. O'Lenick, Jr.
  • Patent number: 5473089
    Abstract: 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: Grant
    Filed: April 14, 1994
    Date of Patent: December 5, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Bernhard Gutsche, Timothy J. Cassady, Lutz Jeromin, Gerhard Wollmann, Norman Milstein, Hans-Christian Raths
  • Patent number: 5468887
    Abstract: 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: Grant
    Filed: March 13, 1992
    Date of Patent: November 21, 1995
    Assignee: The Dial Corp.
    Inventor: Shyam K. Gupta
  • Patent number: 5442081
    Abstract: 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: Grant
    Filed: October 4, 1993
    Date of Patent: August 15, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Arno Behr, Hans-Peter Handwerk
  • Patent number: 5434279
    Abstract: 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: Grant
    Filed: May 6, 1994
    Date of Patent: July 18, 1995
    Inventor: Theodor Wimmer
  • Patent number: 5399730
    Abstract: 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: Grant
    Filed: August 1, 1991
    Date of Patent: March 21, 1995
    Assignee: 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
  • Patent number: 5399731
    Abstract: 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: Grant
    Filed: March 10, 1992
    Date of Patent: March 21, 1995
    Assignee: Vogel & Noot Industrieanlagenbau Gesellschaft m.b.H.
    Inventor: Theodor Wimmer
  • Patent number: 5362894
    Abstract: 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: Grant
    Filed: November 12, 1993
    Date of Patent: November 8, 1994
    Assignees: Arco Chemical Technology, L.P., CPC International, Inc.
    Inventors: Beth M. Handwerker, Charles F. Cooper, Bernard C. Sekula
  • Patent number: 5354878
    Abstract: 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: Grant
    Filed: March 26, 1993
    Date of Patent: October 11, 1994
    Inventors: Joosten Connemann, Anton Krallmann, Erich Fischer
  • Patent number: 5214172
    Abstract: Transvinylation of a vinyl ester with either an alcohol to form a vinyl ether or a carboxylic acid to form a vinyl ester of different molecular weight than the starting ester is catalyzed with a palladium catalyst which is introduced to the reaction mixture as a palladium carboxylate complexed with an aryl N-containing ligand and the activity of this reaction is significantly improved with the addition of a strong acid. Also described are phenanthroline compounds and their novel complexes with palladium acetate which are useful as transvinylation catalysts.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: May 25, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Francis J. Waller
  • Patent number: 5210227
    Abstract: 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: Grant
    Filed: February 27, 1991
    Date of Patent: May 11, 1993
    Assignees: Fisons plc, Fujisawa Pharmaceutical Company Limited
    Inventors: Hirokazu Tanaka, Martin E. Cooper, David K. Donald
  • Patent number: 5177229
    Abstract: 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: Grant
    Filed: July 10, 1991
    Date of Patent: January 5, 1993
    Assignee: Huls Aktiengesellschaft
    Inventors: John Kahsnitz, Alfred Oberholz, Udo Knippenberg, Michael Zolffel
  • Patent number: 5159092
    Abstract: 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: Grant
    Filed: September 12, 1990
    Date of Patent: October 27, 1992
    Assignee: Buss AG
    Inventor: Gunter M. Leuteritz
  • Patent number: 5157132
    Abstract: 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: Grant
    Filed: May 18, 1990
    Date of Patent: October 20, 1992
    Assignee: Carotech Associates
    Inventors: Barrie Tan, Mohammed H. Saleh
  • Patent number: 5130061
    Abstract: 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: Grant
    Filed: May 24, 1989
    Date of Patent: July 14, 1992
    Assignee: Innova di Ridolfi Flora & C. s.a.s.
    Inventors: Franco Cornieri, Walter Di Fulvio
  • Patent number: 5118448
    Abstract: 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: Grant
    Filed: October 19, 1990
    Date of Patent: June 2, 1992
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Charles F. Cooper
  • Patent number: 5116546
    Abstract: 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: Grant
    Filed: April 3, 1990
    Date of Patent: May 26, 1992
    Assignee: Van den Bergh Foods Co., Division of Conopco, Inc.
    Inventors: Robbert Klok, Herbert H. Verveer
  • Patent number: 5110508
    Abstract: 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: Grant
    Filed: April 20, 1989
    Date of Patent: May 5, 1992
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Karl-Heinz Buettgen, Bernhard Gutsche, Friedrich Hommers, Wilhelm Johannisbauer, Eberhard Peukert, Reinhold Sedelies