Another Reactant Contains Alcoholic Or Phenolic Hydroxy Patents (Class 554/170)
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Publication number: 20090217573Abstract: There is disclosed a method for manufacturing fatty acid alkyl esters from tall oil comprising the steps of a) esterifying tall oil in at least one esterification reactor in the presence of an acidic catalyst and an C1 to C8 alcohol to form a crude product stream comprising fatty acid alkyl esters and H2O, b) separating H2O and alcohol from the crude product stream formed in step a) to form a dehydrated fatty acid alkyl ester product stream, and c) separating dehydrated fatty acid alkyl ester product stream from step b) into at least two product streams wherein one product stream is enriched in fatty acid alkyl esters and one product stream is enriched in resin acid compounds. There are disclosed fatty acid alkyl esters and resin acids manufactured by the method. Moreover there is disclosed a fuel composition and its use as an automotive fuel, said fuel composition comprises the fatty acid alkyl esters produced according to the present invention.Type: ApplicationFiled: October 19, 2006Publication date: September 3, 2009Applicant: Kiram ABInventor: Lars Stigsson
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Publication number: 20090198077Abstract: The present invention relates to a method for producing fatty acid alkyl esters as well as cellulosic simplified sugars, shortened protein polymers, amino acids, or combination thereof resulting from the simultaneous esterification and hydrolysis, alcoholysis, or both of algae and other oil containing materials containing phospholipids, free fatty acids (FFA), glycerides, or combination thereof as well as polysaccharides, cellulose, hemicellulose, lignocellulose, protein polymers, or combination thereof in the presence of an alcohol and an optional acid catalyst.Type: ApplicationFiled: October 1, 2008Publication date: August 6, 2009Applicant: Inventure Chemical, Inc.Inventors: William W. Berry, Mark G. Tegen, William R. Sutterlin
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Patent number: 7563915Abstract: Methods for improved manufacture of green biodiesel focus on the selection and use of one or more solid metallic oxide base catalyst(s) selected from the group consisting of calcium oxide (CaO), calcium aluminum oxide (CaO—Al2O3), calcium titanate (CaTiO3), barium titanate (BaTiO3), magnesium aluminum oxide (MgO—Al2O3), zinc oxide (ZnO), copper (II) oxide (CuO), nickel oxide (NiO), manganese oxide (MnO), titanium oxide (TiO), vanadium oxide (VO), cobalt oxide (CoO), iron oxide (FeO), chromite (FeCr2O4), hydrotalcite (Mg6Al2(CO3)(OH)16.4(H2O), magnetite (Fe3O4), magnesium silicate and calcium silicate.Type: GrantFiled: May 29, 2007Date of Patent: July 21, 2009Assignee: The Penn State Research FoundationInventors: Jack Vincent Matson, Dheeban Chakravarthi Kannan
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Publication number: 20090182159Abstract: A nano-cavitational generator for generating cavitational features in a fluidic medium. The generator is a static device that includes a series of chambers having varying diameters and flow areas to create variations in fluid velocity and pressure. The variations in fluid pressure create cavitational bubbles and eddies of internal pressure, which result in long-term, stable and ultra-thin emulsions and dispersions of the fluidic medium. The gas-liquid interface around the cavitational bubbles provides increased surface are for process reactions.Type: ApplicationFiled: June 23, 2008Publication date: July 16, 2009Inventors: Roman Gordon, Igor Gorodnitsky, Sergio J. Lebid
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Publication number: 20090156846Abstract: Disclosed is a process for producing a fatty alkyl ester and glycerin, including step 1 of reacting fats and oils with C1 to C5 lower alcohols, step 2 of removing the lower alcohols discharged from the outlet of a rector in step 1 until the lower alcohol content is reduced to 8 wt % or less, step 3 of separating the product obtained in step 2 into oil and aqueous phases, step 4 of reacting the oil phase obtained in step 3 with lower alcohols in the presence of an acid catalyst, and step 5 of separating the product discharged from the outlet of a reactor in step 4 into oil and aqueous phases thereby giving fatty acid alkyl esters and glycerin, as well as a process for producing fatty alcohols from hydrogen and the fatty acid alkyl esters obtained in the above process.Type: ApplicationFiled: December 19, 2006Publication date: June 18, 2009Applicant: KAO CORPORATIONInventors: Yuichiro Seki, Nobuhiro Tatsumi, Takanobu Katayama
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Publication number: 20090131700Abstract: The present invention concerns a process for forming a fatty acid, a fatty acid ester or a mixture thereof from a soap-comprising starting material, in which process a metal-ion forming agent is added to the starting material, whereby a mixture is formed, which contains an insoluble phase and a liquid phase, the insoluble phase is separated from the liquid phase, and an acid is added into the insoluble phase to form a fatty acid, or a monohydric alcohol and an acid catalyst are added to form a fatty acid ester, whereby two phases are formed, an aqueous phase and an organic phase, or, first, an acid is added and then a monohydric alcohol and an acid catalyst are added into at least a portion of the formed fatty acid to esterify the fatty acid.Type: ApplicationFiled: September 8, 2008Publication date: May 21, 2009Applicant: Helsinki University of TechnologyInventors: Ossi Pastinen, Simo Laakso, Sanna Hokkanen, Marjatta Vahvaselka
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Patent number: 7507846Abstract: Method and apparatus for producing biodiesel fuel, i.e., alkyl ester, from vegetable and/or animal oil. A transesterification catalyst is prepared in a base catalyst tank by spraying alkyl alcohol under pressure through jets at metal hydroxide pellets until the pellets have fully reacted with the alcohol. The oil is heated and transesterified in the presence of alkyl alcohol and the transesterification catalyst in a closed, recirculating transesterification flow system under slight cavitation to yield product alkyl ester and product glycerol. Cavitation is achieved by permitting air to enter the transesterification flow system through an adjustable air inlet valve. When permitted to stand, product alkyl ester forms an upper layer that is decanted and subjected to purification steps, to remove particulates and alkyl alcohol from the product alkyl ester, and a lower layer of product glycerol is drained away.Type: GrantFiled: March 17, 2004Date of Patent: March 24, 2009Inventor: Michael F. Pelly
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Publication number: 20090069586Abstract: To provide: a production method using a catalyst which can substantially suppress leaching of active metal components and exhibit high activity for both reactions of transesterification of glycerides and esterification of free fatty acids each contained in a fat or oil; and the catalyst.Type: ApplicationFiled: February 20, 2006Publication date: March 12, 2009Applicants: Nippon Shokubai Co., Ltd., Research Institute of Innovative Technology For the EarthInventors: Tomoharu Oku, Toshimitsu Moriguchi, Takeo Akatsuka, Masanori Nonoguchi
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Patent number: 7481981Abstract: The apparatus for the esterification of a fatty acid F includes a column with a packing. In addition to functioning as a catalytic reactor, the packing functions as a stripping section. A heteregenous catalysis of a fatty acid is carried out with an alcohol used in the same molar ratio or in excess. A gaseous alcohol-rich counter-flow is produced in a sump of the column by vaporization. Water is removed from the reaction zone by means of the counter-flow acting as a stripping gas. The loaded stripping gas is at least partially liquefied at the head of the column. The head product is separated into a water-rich fraction as well as an alcohol-rich fraction. The alcohol-rich fraction is returned to the process as a starting material for the esterification and for the production of the stripping gas.Type: GrantFiled: April 17, 2006Date of Patent: January 27, 2009Assignee: Sulzer Chemtech AGInventors: Peter Moritz, Peter Faessler, Claudia von Scala, Oliver Bailer
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PROCESS FOR PRODUCTION OF FATTY ACID ALKYL ESTER AND PRODUCTION APPARATUS FOR FATTY ACID ALKYL ESTER
Publication number: 20090023938Abstract: An object of the present invention is to provide a method for producing an alkyl ester of a fatty acid from a fat or oil, of which main component is a triglyceride, and an alkyl alcohol under mild conditions in a high reaction efficiency, and the alkyl ester of a fatty acid can be effectively utilized as a diesel fuel oil, an industrial raw material or the like, the method further being capable of utilizing on an industrial scale, in which post-treatment steps for removing a catalyst component can be simplified or omitted. For this purpose, the method for producing an alkyl ester of a fatty acid of this invention includes the step of carrying out a transesterification reaction between a fat or oil and an alcohol in the presence of a base catalyst containing calcium oxide, characterized in that the method includes the step of contacting the base catalyst with the alcohol, to carry out an activation treatment thereof in advance of the reaction.Type: ApplicationFiled: January 26, 2007Publication date: January 22, 2009Applicants: REVO INTERNATIONAL INC., EHIME UNIVERSITYInventors: Ayato Kawashima, Hideo Yamamoto, Tetsuya Koshikawa -
Publication number: 20090005582Abstract: Vessels and methods for esterification and transesterification of fatty acids under near critical or supercritical reaction conditions are disclosed herein. Alkyl esters produced in the vessel with the disclosed methods are used to create biofuel, such as biodiesel.Type: ApplicationFiled: June 20, 2008Publication date: January 1, 2009Inventor: Greg Anderson
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Publication number: 20080241902Abstract: The present invention relates to a method for producing fatty acid alkyl esters as well as cellulosic simplified sugars, shortened protein polymers, amino acids, or combination thereof resulting from the simultaneous esterification and hydrolysis, alcoholysis, or both of algae and other oil containing materials containing free fatty acids (FFA), glycerides, or combination thereof as well as polysaccharides, cellulose, hemicellulose, lignocellulose, protein polymers, or combination thereof in presences of an alcohol and an acid catalyst.Type: ApplicationFiled: April 2, 2008Publication date: October 2, 2008Applicant: Inventure Chemical, Inc.Inventors: William Wes Berry, Mark G. Tegen, Stephen L. Hillis
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Publication number: 20080227994Abstract: The invention relates to a process for the production of carboxylic acid esters by esterification of carboxylic acids and/or transesterification of carboxylic acid esters with alcohols in the presence of a liquid metal catalyst, characterized in that the liquid metal catalyst is the alkaline earth metal salt of a carboxylic acid.Type: ApplicationFiled: July 24, 2006Publication date: September 18, 2008Applicant: BDI BIODIESEL INTERNATIONAL AGInventors: Wolfgang Glasl, Martin Mittelbach, Matthaeus Siebenhofer, Erich Jeitler, Wilhelm Hammer, Helmut Gossler, Michael Koncar
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Patent number: 7151187Abstract: A new process for the production of linear monocarboxylic acid esters with 6 to 26 carbon atoms, by reaction of vegetable oils or animal oils that may or may not be neutral, with monoalcohols of 1 to 18 carbon atoms, uses a catalyst that is selected from among: the combinations of zinc oxides and titanium oxides; the combinations of zinc oxide, titanium oxide and alumina; the combinations of bismuth and titanium oxides; and the combinations of bismuth oxide, titanium oxide and alumina. The process makes it possible to produce directly, in one or more stages, an ester that can be used as a fuel and a pure glycerin.Type: GrantFiled: May 2, 2005Date of Patent: December 19, 2006Inventors: Bruno Delfort, Gérard Hillion, Dominique Le Pennec, Christophe Lendresse
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Patent number: 7091367Abstract: The method for the esterification of a fatty acid F is carried out in a column with a packing. In addition to functioning as a catalytic reactor, the packing functions as a stripping section. A heteregenous catalysis of a fatty acid is carried out with an alcohol used in the same molar ratio or in excess. A gaseous alcohol-rich counter-flow is produced in a sump of the column by vaporization. Water is removed from the reaction zone by means of the counter-flow acting as a stripping gas. The loaded stripping gas is at least partially liquefied at the head of the column. The head product is separated into a water-rich fraction as well as an alcohol-rich fraction. The alcohol-rich fraction is returned to the process as a starting material for the esterification and for the production of the stripping gas.Type: GrantFiled: November 12, 2003Date of Patent: August 15, 2006Assignee: Sulzer ChemtechInventors: Peter Moritz, Peter Faessler, Claudia von Scala, Oliver Bailer
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Patent number: 6939980Abstract: A method for producing an ester comprising the steps of reacting an alcohol with a carboxylic acid to obtain a crude esterfied product, adding 5 to 100 parts by weight of a hydrocarbon solvent with respect to 100 parts by weight of the crude esterified product and performing neutralization with an alkali aqueous solution. An alcohol solvent can be added, if necessary. Thus, a method for producing an ester is provided in which a high-quality ester is obtained at a high yield.Type: GrantFiled: September 10, 2001Date of Patent: September 6, 2005Assignee: NOF CorporationInventors: Michimasa Memita, Keiji Hirao
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Patent number: 6887283Abstract: A process for producing alkyl esters useful in biofuels and lubricants by transesterifying glyceride- or esterifying free fatty acid-containing substances in a single critical phase medium is disclosed. The critical phase medium provides increased reaction rates, decreases the loss of catalyst or catalyst activity and improves the overall yield of desired product. The process involves the steps of dissolving an input glyceride- or free fatty acid-containing substance with an alcohol or water into a critical fluid medium; reacting the glyceride- or free fatty acid-containing substance with the alcohol or water input over either a solid or liquid acidic or basic catalyst and sequentially separating the products from each other and from the critical fluid medium, which critical fluid medium can then be recycled back in the process.Type: GrantFiled: July 22, 1999Date of Patent: May 3, 2005Assignee: Bechtel BWXT Idaho, LLCInventors: Daniel M. Ginosar, Robert V. Fox
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Patent number: 6841691Abstract: Method for the preparation of an enantiomerically enriched ester, in which a mixture of the enantiomers of the corresponding secondary alcohol is subjected, in the presence of an acyl donor, to an enantioselective conversion in the presence of a racemisation catalyst upon which the ester is formed and an acyl donor residue is obtained, and in which the acyl donor residue is irreversibly removed from the phase in which the enantioselective conversion takes place. Preferably the enantioselective conversion is carried out enzymatically and a transfer hydrogenation catalyst is used as racemisation catalyst. The secondary alcohol can be formed in situ from the corresponding ketone, in the presence of a hydrogen donor. It is also possible to use a mixture of the secondary alcohol and the corresponding ketone as substrate. Preferably the acyl donor is chosen so that the acyl donor residue is converted in situ into another compound and/or the acyl donor residue is removed via distillation under reduced pressure.Type: GrantFiled: May 21, 2001Date of Patent: January 11, 2005Assignee: DSM N.V.Inventors: Gerardus Karel Maria Verzijl, Johannes Gerardus Vries De, Quirinus Bernardus Broxterman
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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: 6797753Abstract: Compositions and methods for plasticizing polyvinyl chloride polymers where the plasticizers contain fatty acids derived from vegetable oils and the fatty acids are substantially fully esterified with an alcohol (monool or polyol), the fatty acids having unsaturated bonds that are substantially fully epoxidized, and wherein the fatty acids are added substantially randomly to one or more hydroxyl sites on the alcohol. The plasticizers may be added in amounts between about 10 to 230 pph of PVC resin.Type: GrantFiled: May 4, 2001Date of Patent: September 28, 2004Assignee: Battelle Memorial InstituteInventors: Herman P. Benecke, Bhima R. Vijayendran, Joel D. Elhard
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Patent number: 6713221Abstract: An ester wax is obtained by a condensation reaction of carboxylic acid and alcohol; wherein the carboxylic acid contains a single kind of saturated linear monocarboxylic acid having 14 to 30 carbon atoms as a main component, and the single kind of carboxylic acid is contained in a ratio of 60 wt % or more of the entire carboxylic acid; the alcohol contains a single kind of saturated linear monohydric alcohol having 14 to 30 carbon atoms or a single kind of polyhydric alcohol having 2 to 6 hydroxyl groups and having 2 to 30 carbon atoms as a main component, and when the monohydric alcohol is the main component, the monohydric alcohol is contained in a ratio of 60 wt % or more of the entire alcohol, and when the polyhydric alcohol is the main component, the polyhydric alcohol is contained in a ratio of 80 wt % or more of the entire alcohol; and the ester wax has an acid value of 3 mgKOH/g or less, and a hydroxyl value of 5 mgKOH/g or less, and a maximum peak temperature in a differential thermal curve is in a rType: GrantFiled: January 11, 2002Date of Patent: March 30, 2004Assignee: NOF CorporationInventors: Koji Kada, Kouhei Sawada, Show Onodera
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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: 6548609Abstract: The present invention is related to an improved process for obtaining oleochemical polyols from oils, principally of a vegetable origin. The polyols obtained consist of a mixture of ethers, esters, primary and secondary alcohols and have the characteristic of being self-compatible with the new blowing agents: hydrochlorofluorocarbons, HCFC's, hydrofluorocarbons, HFC's and hydrocarbons, HC's of a low molecular weight and low boiling point. The process of this invention is characterized because it uses Lewis type acids in such a way that they do not form precipitates and therefore it is not necessary to remove precipitates from the polyol. The process of the present invention makes it possible to obtain polyols with high functionality and controlled reactivity. These characteristics render the product suitable for use as a raw material in the production process of rigid foams, such as polyurethane for spraying, refrigeration and imitation wood, coatings, among others.Type: GrantFiled: November 21, 2001Date of Patent: April 15, 2003Assignee: Resinas Y Materiales S.A. De C.V.Inventors: Nicolás Ramírez-de-Arellano-Aburto, Andrés Cohen-Barki, M. Javier Cruz-Gómez
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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: 6361980Abstract: The present invention provides a process for preparing a diglyceride, which includes: in an enzyme-packed tower which includes an immobilized lipase preparation, carrying out an esterification reaction between: (1) an acyl group donor selected from the group including a fatty acid, a lower alcohol ester thereof, and a mixture thereof; and (2) an acyl group acceptor selected from the group including glycerol, a monoglyceride, and a mixture thereof; to obtain a reaction fluid from the enzyme-packed tower; reducing a water content or a lower alcohol content in the reaction fluid; and subsequent to the reducing, recirculating the reaction fluid to the enzyme-packed tower, wherein a residence time of the reaction fluid in the enzyme-packed tower is 120 seconds or less; to obtain a diglyceride. According to the present invention, a high-purity glyceride can be provided at a high yield in a short period of time.Type: GrantFiled: November 30, 2000Date of Patent: March 26, 2002Assignee: Kao CorporationInventors: Masakatsu Sugiura, Hiroaki Yamaguchi, Naoto Yamada
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Patent number: 6355817Abstract: The present invention provides a process for the production of an ester, including reacting an alcohol with a carbonyl-like compound in the presence of a first esterification catalyst; and adding a second esterification catalyst to the reaction mixture at some time after initiation of the esterification reaction. The staged addition of the esterification catalyst according to the present invention provides a reduced reaction time to achieve a targeted conversion to esters.Type: GrantFiled: July 15, 2000Date of Patent: March 12, 2002Assignee: ExxonMobil Chemical Patents Inc.Inventors: David G. Woods, Larry O. Jones, Pei-Yi Lo
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Patent number: 6342199Abstract: The invention relates to a process for conducting a chemical reaction characterized by an equilibrium in a reaction system designed as a loop reactor, said loop reactor comprising a reactor vessel (1), at least one loop connected to said reactor vessel (1) each by means of an outlet and an inlet, said loop comprising means (3) for pumping over a fluid reaction material, at least one he exchanger (4), optionally means (5) for feeding said reaction material into Me reactor vessel (1) and a separate gas loop (8) which is connected to the gas space of the reactor vessel (1) above the reaction mixture and has separate means for feeding a gas into the gas loop (8), for withdrawing gas from the gas loop (8) and/or for treating said gas circulating in the gas loop (8), said process comprising the steps of circulating and/or treating said gas in said gas loop (8), feeding said gas into the reactor vessel (1) for influencing the equilibrium of a reaction conducted in said reactor vessel (1) and being characterized by tType: GrantFiled: June 18, 1999Date of Patent: January 29, 2002Inventor: Vincent Simon Ellis
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Patent number: 6320065Abstract: The invention relates to a process for the preparation of fatty acid partial esters of polyols, the fatty acid partial esters thus obtainable, and their use. The fatty acid partial esters (I) of polyols having at least 4 C atoms, at least one primary and at least one secondary alcohol group of the starting polyols are obtained in a process, where in a first process step the polyols are reacted with a fatty acid or a fatty acid derivative to give a fatty acid partial ester (II) and in a second process step the fatty acid partial esters (II) obtained are subjected to a selective enzymatic cleavage of primary ester groups.Type: GrantFiled: May 7, 1999Date of Patent: November 20, 2001Assignee: Goldschmidt AGInventors: Burghard Gruning, Geoffrey Hills
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Patent number: 6274749Abstract: High-temperature resistant sulfonated aromatic polyether ketone cation exchangers and sulfonated poly(phenylene sulfide) cation exchangers are revealed as catalysts for various reactions at reaction temperatures above 150° C. The invention relates to the use of sulfonated aromatic polyether ketone cation exchangers and sulfonated poly(phenylene sulfide) cation exchangers as catalysts for such reactions. The preferred reaction is esterification to make octyl palmitate.Type: GrantFiled: July 23, 1998Date of Patent: August 14, 2001Assignee: Hoechst Research & Technology GmbH & Co. KGInventors: Werner Sievers, Ulrich Daiminger, Harald Bönsel, Wolfgang Bauer, Joachim Semel
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Patent number: 6242620Abstract: Sulfur and soap contaminants are removed from carboxylic acid esters by a process comprising the steps of: (1) contacting a carboxylic acid ester with an aqueous base at a temperature of from about 225° F. to about 280° F. while removing water to form a dry, crude ester; (2) contacting the dry, crude ester with an absorbent selected from the group consisting of silica gel, hydro-silica gel and mixtures thereof; (3) separating the absorbent from the ester.Type: GrantFiled: March 5, 1998Date of Patent: June 5, 2001Assignee: Henkel CorporationInventors: A. Fred Elsasser, C. William Blewett, Charles M. White
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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: 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: 5866710Abstract: A process for the preparation of an ester comprises carrying out an esterification in the presence of a catalyst comprising the reaction product of an orthoester or a condensed orthoester of titanium or zirconium, an alcohol containing at least two hydroxyl groups, a 2-hydroxy acid and a base. The process can be a direct esterification or a transesterification and can be a polyesterification. The catalyst can effectively produce esters without leading to a haze in the final product and there is a reduced amount of yellowing of polyesters in comparison to known catalysts.Type: GrantFiled: June 5, 1997Date of Patent: February 2, 1999Assignee: Tioxide Specialties LimitedInventors: John Ridland, Iain Wesley Hepplewhite, Brian Steven Jolly
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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: 5646321Abstract: The present invention deals with the certain novel esters which are prepared by the reaction of a guerbet alcohol and meadowfoam fatty, methyl ester or triglyceride. These materials are useful as cosmetic ingredients where outstanding liquidity, resistance to oxidation, and minimal taste and odor variation are required. This combination of properties make these compounds excellent candidates as additives to personal care products like skin care oils and lipsticks.Type: GrantFiled: August 17, 1995Date of Patent: July 8, 1997Assignee: Siltech Inc.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5571938Abstract: The present invention provides for an esterification process comprising a catalyst source of stannous tin and an alkali metal aluminate. In one preferred embodiment the catalyst comprises about 92 parts sand, about 5 parts stannous oxalate, and about 3 parts of a sodium aluminate, by weight, dry basis. This catalyst is particularly useful in making phthalates, adipates, sebacates and azelates which esters are chiefly used plasticizers.Type: GrantFiled: July 31, 1995Date of Patent: November 5, 1996Inventor: Stan Jakubowycz
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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: 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: 5466843Abstract: Esterified alkoxylated polyols containing long chain saturated linear acyl groups are obtained by esterification of an alkoxylated polyol such as propoxylated glycerin with a C.sub.12 -C.sub.24 fatty acid such as behenic acid and recovery of excess fatty acid by treatment with an aliphatic hydrocarbon. Esterified alkoxylated polyols prepared in this manner are useful fat substitutes for the formulation of reduced calorie food products.Type: GrantFiled: April 29, 1994Date of Patent: November 14, 1995Assignee: ARCO Chemical Technology, L.P.Inventor: Charles F. Cooper
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Patent number: 5426199Abstract: Esters may be produced with a minimum formation of ether by-product by reacting an organic acid or ester with an alcohol at elevated temperatures in the presence of vinylaromatic polymer beads which are surface functionalized with strongly acidic functional groups, the inner volume of the polymer beads remaining unfunctionalized.Type: GrantFiled: December 14, 1992Date of Patent: June 20, 1995Assignee: Rohm and Haas CompanyInventor: Eric G. Lundquist
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Patent number: 5424469Abstract: A process for preparing polyglycerol fatty acid ester mixtures in which a polyglycerol mixture of 0.1 to 20 wt % monoglycerol, 20 to 35 wt % diglycerol, 30 to 40 wt % triglycerol and 49.9 to 5 wt % tetra- and higher polyglycerols is reacted with one or more fatty acids, selected from the saturated C.sub.8 - to C.sub.18 -fatty acids (containing 0 to 15 wt % unsaturated fatty acids), in a molar ratio of the polyglycerol to the fatty acid component of 0.3:1.5 to 1.5:0.5 in the presence of at least one catalyst and at reduced pressure, by initially heating the reaction mixture to at least 140.degree. C. and reducing the pressure to at least 600 mbar and then heating the reaction mixture at a temperature from 140.degree. to 220.degree. C. and reducing the pressure from 600 to 10 mbar. After completion of the reaction, the resulting polyglycerol fatty acid ester mixture is cooled and optionally worked up and/or purified.Type: GrantFiled: July 12, 1993Date of Patent: June 13, 1995Assignee: Solvay Fluor und Derivate GmbHInventors: Gerald Jakobson, Werner Siemanowski, Karl-Heinz Uhlig
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Patent number: 5405980Abstract: Condensates (K) of(A) oligohydroxy-C.sub.3-8 -alkanes containing at least 3 hydroxy groups and (B) KOH,that contain at least 5% by weight of K.sup.+ and at least one alcoholic hydroxy groupare eminently suitable as oxyalkylation catalysts, in particular for the oxyalkylation of ester group-containing substrates, before all of natural, vegetable or animal fats or oils or their modification products.Type: GrantFiled: February 24, 1993Date of Patent: April 11, 1995Assignee: Sandoz Ltd.Inventor: Hans-Peter Baumann
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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: 5349075Abstract: The invention provides a process for the esterification of a C.sub.2 -C.sub.24 monocarboxylic acid with a C.sub.1 -C.sub.5 monoalcohol in a reactor at an increased reaction temperature and increased pressure which is carried out in the absence of any esterification catalyst while continuously feeding in the alcohol during the reaction and removing a gaseous alcohol/water mixture. Preferably the process is carried out in countercurrent in column reactor which is packed or contains plates. The reaction temperature is usually between 200.degree. C. and 260.degree. C. at a pressure between 0.5 and 1.5 MPa. There is a C.sub.6 -C.sub.20 monocarboxylic acid and monoalcohol a C.sub.1 -C.sub.3 monoalcohol. More preferably the process is carried in two steps with a first step as described above and a second step in which further reaction to a conversion of at least 99% is carried out in the presence of an esterification catalyst at a temperature below 100.degree. C.Type: GrantFiled: December 21, 1990Date of Patent: September 20, 1994Assignee: Unilever Patent Holdings B.V.Inventors: Hendrikus J. van den Berg, Robbert Klok
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Patent number: 5324846Abstract: The present invention relates to a partial ester derived from the reaction product of an oxirane containing acid or derivative thereof, and a reactive hydroxyl compound selected from the group consisting of diols, triols, di-diols and 1,4-dihydroxy butane and a halogen containing polymer compositon thereof. The oxirane compound can be derived from the group consisting of epoxidized vegetable oil, epoxidized fish oil, an aliphatic or arylaliphatic containing craboxyl compound having an oxirane group in the aliphatic chain.Type: GrantFiled: January 30, 1992Date of Patent: June 28, 1994Assignee: Elf Atochem North America, Inc.Inventors: Justin L. Hirshman, Dana S. Garcia, Mohammad R. Kazemizadeh
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Patent number: 5149852Abstract: This invention provides a process for concentration and separation of an eicosapentaenoic acid ester comprising:(1) a step in which a solution, in a nonpolar solvent, of a mixture of fatty acid esters containing an eicosapentaenoic acid ester is allowed to contact with a zeolite, so as to allow said eicosapentaenoic ester to be adsorbed on said zeolite;(2) a step in which said zeolite is allowed to contact with a nonpolar solvent, so as to desorb impurities; and(3) a step in which said zeolite is allowed to contact with a polar solvent, so as to allow said eicosapentaenoic acid ester to be desorbed.This process makes it possible to obtain a highly pure eicosapentaenoic acid ester on a commercial scale.Type: GrantFiled: March 27, 1991Date of Patent: September 22, 1992Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Makoto Arai, Hideki Fukuda