Plural Hydroxys In The Hydroxy Containing Reactant Patents (Class 554/172)
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Publication number: 20150148554Abstract: The invention discloses an improved process for preparing fatty acid esters with 100 mol % selectivity suitable as biodegradable lubricant base oils, comprising contacting a fatty compound with an alcohol in presence of a solid, phosphonate catalyst having molecular formula: M(X)2-nYn.mH2O where X refers to phenyl phosphonate, Y refers to HPO42? or HPO32?, M refers to a metal or metalloid ion preferably taken from the group consisting of Zr, Zn, Cd, Al, Sn, La and Ce, the value of n varies from 0.2 to 1.8 and the value of m varies from 0 to 5, wherein the fatty compound is a fatty acid or fatty acid methyl or ethyl ester or vegetable oil or animal fat or their mixture thereof and alcohol is a monohydric alcohol with 6 to 22 carbon atoms or a polyol with at least two hydroxyl groups.Type: ApplicationFiled: May 22, 2013Publication date: May 28, 2015Inventors: Darbha Srinivas, Mehejabeen Kotwal
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Publication number: 20150119594Abstract: The invention provides a method of preparing ?-erythritol fatty acid monoester, including: subjecting a fatty acid and erythritol to esterification reaction in the presence of an acid catalyst, a water carrier and an optional phase transfer catalyst, wherein the molar ratio of the fatty acid to erythritol is 1:2 to 1:3, and the temperature of the esterification reaction is 80-100° C. In addition, the invention further provides a method of preparing 2,3-erythritol fatty acid diester, including: subjecting a fatty acid and erythritol to esterification reaction in the presence of an acid catalyst and a water carrier, wherein the molar ratio of the fatty acid to erythritol is 2:1 to 3:1, and the temperature of the esterification reaction is 120-160° C.Type: ApplicationFiled: May 24, 2013Publication date: April 30, 2015Applicant: Wilmar (Shanghai) Biotechnology Research & Development Center Co., LTDInventors: Zonghui Ma, Yan Zheng, Tiankui Yang, Xuebing Xu
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Patent number: 8759559Abstract: Provided are processes for preparing polytrimethylene ether glycol monoester or diesters composition wherein polytrimethylene ether glycol containing less than about 1 weight % of unreacted diol monomer is reacted with an equivalent excess of a monocarboxylic acid.Type: GrantFiled: April 18, 2012Date of Patent: June 24, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Hari Babu Sunkara, Sam Cotterill
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Publication number: 20140105843Abstract: The present invention relates to a process for the preparation of an ester comprising an after-treatment of the ester to give an ester in granule form of defined particle size distribution, a device for carrying out this process, a process for the preparation of a thermoplastic composition comprising the ester prepared according to the invention, a process for the production of a shaped article comprising the ester according to the invention or the thermoplastic composition according to the invention, a process for the production of a packed product, a process for the production of an at least partly coated object, and uses of the esters according to the invention as an additive in various compositions.Type: ApplicationFiled: February 21, 2012Publication date: April 17, 2014Inventors: Peter Daute, Wilhelm Reiners, Martin Schäfer, Udo Frerichs, Hinrich Hildebrandt, Joern Ellerbrake
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Patent number: 8623916Abstract: The present invention relates to compounds of the following formula (I): where n is an integer between 1 and 15, m is 0, 1, 2 or 3, and R is the hydrocarbon chain of a polyunsaturated fatty acid selected from among omega 3 and omega 6, as well as to pharmaceutical or cosmetic compositions containing same, to a method for preparing and using same, in particular for treating acne and seborrhoeic dermatitis.Type: GrantFiled: December 21, 2009Date of Patent: January 7, 2014Assignee: Pierre Fabre Dermo-CosmetiqueInventors: Daniel Redoules, Sylvie Daunes-Marion, Marie-Françoise Aries
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Patent number: 8624047Abstract: Solvent-less methods to convert oil derivatives, and modified oils to highly functionalized esters, ester polyols, amides, and amide polyols. The products can be used to make polyurethane and polyester films and foams.Type: GrantFiled: December 31, 2009Date of Patent: January 7, 2014Assignee: Battelle Memorial InstituteInventors: Daniel B. Garbark, Herman Paul Benecke
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Publication number: 20130345330Abstract: A process for the preparation of polyricinoleic acid esters comprising the step of reaction of ricinoleic acid with an alcohol component which comprises mono- and/or polyfunctional alcohols having a molecular weight of ?32 g/mol to ?40 g/mol, wherein the reaction is carried out at least partly in the presence of a catalyst. The amount of catalyst, based on the total weight of the ricinoleic acid and the alcohol component, is in a range of from ?10 ppm to ?100 ppm. The reaction is ended when the acid number of the reaction product obtained is ?5 mg of KOH/g to ?100 mg of KOH/g. The invention furthermore relates to a polyurethane polymer, in particular a flexible polyurethane foam, which is obtainable using these polyricinoleic acid esters.Type: ApplicationFiled: November 18, 2011Publication date: December 26, 2013Applicant: BAYER INTELLECTUAL PROPERTY GMBHInventors: Hartmut Nefzger, Erika Bauer, Bert Klesczewski, Jüergen Schlossmacher, Sven Meyer-Ahrens, Manfred Schmidt
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Patent number: 8603959Abstract: Fatty esters of oligoesters of a dicarboxylic acid and a polyol retaining at least one free hydroxyl group, particularly of the formula (I): R1—[OR2O—C(O)—R3—(O)C—]m—R4 (I), where R1 is H, a monocarboxylic acid group, or R6O—[C(O)—R3—(O)C]—; R2s are residues of polyols having at least one substituent free hydroxyl; R3s are hydrocarbylene; R4 is —OH, —OM where M is a salt forming metal, amine or ammonium, —OR6, or —OR2O—R7; R5 is C7 to C21 hydrocarbyl; R6 is C8 to C22 hydrocarbyl; R7 is H, or —C(O)R5; and m is 1 to 20; provided that at least one of R1 and R4 is or includes a C8 to C22 group, are surfactants. A range of surfactant properties can be obtained by varying the molecules within these ranges. Especially where R2 is derived from a higher polyol e.g. sorbitol, R3 is C2 to C6, and the fatty terminal group is C8 to C14, the products can be highly water soluble and effective oil in water emulsifiers.Type: GrantFiled: October 18, 2005Date of Patent: December 10, 2013Assignee: Croda International PLCInventors: Hanamanthsa S Bevinakatti, Alan G Waite
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Publication number: 20130289291Abstract: A process to prepare an estolide derivative composition comprises reacting a triglyceride having an unsaturation level of less than 0.1 m Eq/g and an alcohol having from 2 to 22 carbon atoms, under conditions such that a product including an oligomerized ester having residual hydroxyl groups is formed; and reacting the product with a capping agent under conditions such that an estolide derivative composition is formed. The compositions may exhibit desirably low pour point, desirable viscosity and thermoxidative stability, and a high level of renewable carbons, making them suitable for use as biolubricants, process fluids, plasticizers, or starting materials for polyurethane polymers.Type: ApplicationFiled: September 20, 2011Publication date: October 31, 2013Applicant: DOW GLOBAL TECHNOLOGIES LLCInventors: Sreejit Nair, Saurabh Kaujalgikar, Daniele Vinci
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Publication number: 20130281723Abstract: Provided are processes for preparing polytrimethylene ether glycol monoester or diesters composition wherein polytrimethylene ether glycol containing less than about 1 weight % of unreacted diol monomer is reacted with an equivalent excess of a monocarboxylic acid.Type: ApplicationFiled: April 18, 2012Publication date: October 24, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: Hari Babu Sunkara, Sam Cotterill
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Publication number: 20130274494Abstract: A method for preparing polyols from fatty acid substrates such as free fatty acids, alkyl esters of fatty acids, mono-glycerides, diglycerides, and triglycerides. The method comprises the steps of (a) epoxidizing an unsaturated fatty acid substrate and (b) hydroxylating the epoxidized fatty acid substrate with at least one diol to produce a polyol or a blend of polyols. The method may be varied to produce polyols with desired functionality, molecular weights, or viscosity.Type: ApplicationFiled: July 21, 2011Publication date: October 17, 2013Applicant: THE GOVERNORS OF THE UNIVERSITY OF ALBERTAInventors: Jonathan Curtis, Guoguang Liu, Tolibjon Omonov, Ereddad Kharraz
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Patent number: 8541536Abstract: Methods of coupling plant oil based polyols so as to synthesis high molecular weight plant oil polyols having a hydroxyl number between from about 40 to about 60. The resultant polyols may be directly reacted with polyisocyanates to produce polyurethanes.Type: GrantFiled: November 5, 2010Date of Patent: September 24, 2013Assignee: MCPU Polymer Engineering LLCInventors: Thomas M. Garrett, Xian Xian Du
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Publication number: 20130210951Abstract: Polyols are produced by an alkoxylation process in which a vegetable oil containing hydroxyl functional groups is combined with a DMC catalyst to form a mixture, the DMC catalyst is then activated by adding ethylene oxide and/or propylene oxide to the vegetable oil/catalyst mixture, and ethylene oxide and propylene oxide are added to the mixture containing activated DMC catalyst in amounts such that the total of percentage of ethylene oxide in the polyol plus percentage of primary hydroxyl groups in the polyol produced is from 50 to 77% and the percentage of primary hydroxyl groups is at least 30% but less than 50%. These polyols are useful for the production of molded polyurethane foams, particularly, hot-cure molded polyurethane foams.Type: ApplicationFiled: April 15, 2011Publication date: August 15, 2013Inventors: Stanley L. Hager, Micah N. Moore, Jack R. Reese, Brian L. Neal
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Patent number: 8471047Abstract: The present invention relates to a series of mixed esters of glycerin esters having two distinct alkyl groups present thereon. One is a low melting product, having a melting point of below 70° C. and the other having a melting point of above 90° C. The presence of the two different melting point groups on the glycerin results in a modification of the hardness, spredability and aesthetics of the resulting mixed ester. This ability to alter hardness and skin aesthetics makes the products of the present invention useful in personal care products ranging as additives to pigmented products to minimize syneresis, to stick products alter the hardness, shrinkability and aesthetics of the stick, to pressed powders where they act to modify the compressability of the powders to which they are added as well as the feel achieved when they are applied to the skin.Type: GrantFiled: January 10, 2011Date of Patent: June 25, 2013Assignee: Surfatech CorporationInventor: Kevin A. O'Lenick
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Patent number: 8455670Abstract: The present invention relates to a series of mixed esters of complex esters having two distinct alkyl groups present thereon. One is a low melting product, having a melting point of below 70° C. and the other having a melting point of above. 90° C. The presence of the two different melting point groups on the polyol results in a modification of the hardness, spreadability and aesthetics of the resulting mixed ester. This ability to alter hardness and skin aesthetics makes the products of the present invention useful in personal care products ranging as additives to pigmented products to minimize syneresis, to stick products alter the hardness, shrinkability and aesthetics of the stick, to pressed powders where they act to modify the compressibility of the powders to which they are added as well as the feel achieved when they are applied to the skin.Type: GrantFiled: January 10, 2011Date of Patent: June 4, 2013Assignee: SuriaTech CorporationInventor: Kevin A. O'Lenick
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Publication number: 20120264955Abstract: Embodiments of the invention include processing lipid feedstocks into various products. Embodiments of the invention include processing lipid feedstocks into various products. In an embodiment, the invention includes a method of processing a lipid feedstock comprising combining triglycerides from the lipid feedstock with water to form a first reaction mixture, contacting the first reaction mixture with a first metal oxide catalyst at a temperature of greater than 200 degrees Celsius to form a first product mixture including free fatty acids and glycerin, combining the free fatty acids with a diol to form a second reaction mixture, and contacting the second reaction mixture with a second metal oxide catalyst at a temperature of greater than 200 degrees Celsius to form a second product mixture. Other embodiments are also included herein.Type: ApplicationFiled: April 13, 2012Publication date: October 18, 2012Applicant: SARTEC CORPORATIONInventors: Clayton V. McNeff, Daniel Thomas Nowlan, Larry C. McNeff, Peter G. Greuel, Bingwen Yan
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Patent number: 8288574Abstract: Method for producing C3H5(OH)3 and at least one of fatty acid methyl ester (FAME) and fatty acid ethyl ester (FAEE) includes mixing vegetable oils and animal fats, at least one of CH3OH and C2H5OH and at least one first catalyst to transesterify a portion of triglycerides and provide a first mixture. The first mixture is separated, with a first light phase being withdrawn and fed into a second mixer where it is mixed with at least one second catalyst to transesterify a further portion of the triglycerides to provide a second mixture. The second mixture is separated, with a second light phase being withdrawn and mixed with soapless C3H5(OH)3 to provide a dispersion which is separated by density difference. A phase containing at least one of raw FAME and raw FAEE is mixed with an aqueous acid, washed with water, with the water being expelled to provide FAME and FAEE product.Type: GrantFiled: September 5, 2008Date of Patent: October 16, 2012Assignee: Lurgi GmbHInventors: Rudolf Boensch, Helmut Saft, Peter Mitschke, Henning Buchold
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Patent number: 8212062Abstract: 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: GrantFiled: April 2, 2008Date of Patent: July 3, 2012Assignee: Inventure Chemical, Inc.Inventors: William Wes Berry, Mark G. Tegen, Stephen L. Hillis
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Publication number: 20120096763Abstract: A method of formulating a fuel composition for use in internal-combustion engines includes the step of providing a fuel. In addition, there is the step of forming the fuel composition by adding to the fuel a polar fluid and an emulsifier. The emulsifier is present in an amount effective for the biodiesel fuel, alcohol, water, and emulsifier to form an emulsion. The emulsifier includes an active surfactant mixture of oleic acid and ammonium oleate, wherein the ratio of oleic acid to ammonium oleate is no more than 60:40.Type: ApplicationFiled: August 24, 2011Publication date: April 26, 2012Applicant: WILLIAM H. KLAUSMEIER FAMILY TRUSTInventor: William H. Klausmeier
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Patent number: 8129324Abstract: Fatty esters of oligoesters of a dicarboxylic acid and a polyol retaining at least one free hydroxyl group, particularly of the formula (I): R1—[OR2O—C(O)—R3—(O)C—]m—R4 (I), where R1 is H, a monocarboxylic acid group, or R6O—[C(O)—R3—(O)C]—; R2s are residues of polyols having at least one substituent free hydroxyl; R3s are hydrocarbylene; R4 is —OH, —OM where M is a salt forming metal, amine or ammonium, —OR6, or —OR2O—R7; R5 is C7 to C21 hydrocarbyl; R6 is C8 to C22 hydrocarbyl; R7 is H, or —C(O)R5; and m is 1 to 20; provided that at least one of R1 and R4 is or includes a C8 to C22 group, are surfactants. A range of surfactant properties can be obtained by varying the molecules within these ranges. Especially where R2 is derived from a higher polyol e.g. sorbitol, R3 is C2 to C6, and the fatty terminal group is C8 to C14, the products can be highly water soluble and effective oil in water emulsifiers.Type: GrantFiled: October 18, 2005Date of Patent: March 6, 2012Assignee: Croda International PLCInventors: Hanamanthsa S Bevinakatti, Alan G Waite
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Patent number: 8067625Abstract: The present invention relates to fatty acid esters of polyols or sulfonated fatty acid esters or sulfonated fatty acid amides containing at least one group Y, where Y stands for CF3—(CH2)a—O—, SF5—, CF3—(CH2)a—S—, CF3CF2S—, [CF3—(CH2)a]2N— or [CF3—(CH2)a]NH—, where a stands for an integer selected from the range from 0 to 5, or formula (I), where Rf stands for CF3—(CH2)r—, CF3—(CH2)r—O—, CF3—(CH2)r—S—, CF3CF2—S—, SF5—(CH2)t— or [CF3—(CH2)r]2N—, [CF3—(CH2)r]NH— or (CF3)2N—(CH2)r—, B stands for a single bond, O, NH, NR, CH2, C(O)—O, C(O), S, CH2—O, O—C(O), N—C(O), C(O)—N, O—C(O)—N, N—C(O)—N, O—SO2 or SO2—O, R stands for alkyl having 1 to 4 C atoms, b stands for 0 or 1 and c stands for 0 or 1, q stands for 0 or 1, where at least one radical from b and q stands for 1, and r stands for 0, 1, 2, 3, 4 or 5, to processes for the preparation of these compounds, and to uses of these surface-active compounds.Type: GrantFiled: July 2, 2007Date of Patent: November 29, 2011Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Wolfgang Hierse, Nikolai (Mykola) Ignatyev, Martin Seidel, Elvira Montenegro, Peer Kirsch, Andreas Bathe
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Publication number: 20110269978Abstract: Solvent-less methods to convert oil derivatives, and modified oils to highly functionalized esters, ester polyols, amides, and amide polyols. The products can be used to make polyurethane and polyester films and foams.Type: ApplicationFiled: December 31, 2009Publication date: November 3, 2011Applicant: BATTELLE MEMORIAL INSTITUTEInventors: Daniel B. Garbark, Herman Paul Benecke
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Publication number: 20110263885Abstract: A new class of oleochemical based polyol esters of general formula 1 are prepared by esterification of different polyols having 5-6 carbon atoms and 2-4 hydroxyl groups with 10-undecenoic acid or/and undecanoic acid with a hydroxyl value of ?1.0 mg KOH/g. Wherein R1, R2, R3 is selected from a group consisting of CH3—, CH3CH2—, —CH2OCOR4 wherein R4 is selected from CH2?CH—(CH2)8— or CH3—(CH2)9—, individually or in combination thereof. The resulting esters were characterized for lubricant properties like viscosity, viscosity index, pour point, flash point and copper corrosion tests. The properties indicate their potential as promising lubricant base stocks for automotive lubricants, metal working oil, hydraulic oil and other industrial applications. Vegetable oils provide most of the desirable lubricant properties such as good boundary lubrication, high viscosity index, high flash point and low volatility.Type: ApplicationFiled: May 14, 2009Publication date: October 27, 2011Inventors: Venkata Padmaja Korlipara, Venkata Surya Koppeswara Rao Bhamidipati, Satya Bhaskar Potula, Badari Narayana Prasad Rachapudi, Arun Kumar Singh
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Publication number: 20110230557Abstract: The present invention relates to compounds of the following formula (I): where n is an integer between 1 and 15, m is 0, 1, 2 or 3, and R is the hydrocarbon chain of a polyunsaturated fatty acid selected from among omega 3 and omega 6, as well as to pharmaceutical or cosmetic compositions containing same, to a method for preparing and using same, in particular for treating acne and seborrhoeic dermatitis.Type: ApplicationFiled: December 21, 2009Publication date: September 22, 2011Applicant: PIERRE FABRE DERMO-COSMETIQUEInventors: Daniel Redoules, Sylvie Daunes-Marion, Marie-Francoise Aries
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Publication number: 20110166315Abstract: Methods of coupling plant oil based polyols so as to synthesis high molecular weight plant oil polyols having a hydroxyl number between from about 40 to about 60. The resultant polyols may be directly reacted with polyisocyanates to produce polyurethanes.Type: ApplicationFiled: November 5, 2010Publication date: July 7, 2011Applicant: MCPU Polymer Engineering LLC, a California Limited Liability CompanyInventors: Thomas M. Garrett, Xian Xian Du
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Publication number: 20110065943Abstract: A method for the selective esterification of free fatty acids, alone or in triglycerides, with C1-C8 aliphatic alcohols or diols. The method uses a selective heterogeneous esterification catalyst. The catalyst is contacted with a reaction mixture containing a triglyceride having at least 0.5% free fatty acids, or a reaction mixture containing only free fatty acids, and a C1-C8 aliphatic alcohol or diol under conditions suitable for esterification.Type: ApplicationFiled: September 16, 2009Publication date: March 17, 2011Inventors: Rajiv Manohar Banavali, Alfred Karl Schultz
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Patent number: 7767838Abstract: The invention provides a process for producing a monoglyceride-containing composition by reacting glycerin with at least one kind of acyl-containing compound selected from fatty acid and glycerin ester, the reaction being conducted with a catalyst containing at least one metal selected from iron, cobalt and manganese in an amount of 0.1 to 60 ppm in terms of metal (weight ratio to the total weight of glycerin and the acyl-containing compound), as well as a process for producing a monoglyceride-containing composition by reacting glycerin with at least one kind of acyl-containing compound selected from fatty acid and glycerin ester, including a step of maintaining the amount of water at 500 to 5000 ppm in the reaction system after the degree of conversion in the reaction of glycerin with fatty acid reaches 90% or more based on the fatty acid, or during the ester exchange reaction of glycerin with glycerin ester.Type: GrantFiled: June 3, 2004Date of Patent: August 3, 2010Assignee: Kao CorporationInventors: Hiroki Sawada, Jiro Hashimoto, Haruya Mino, Toshitsugu Maeda
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Publication number: 20090275769Abstract: A continuous process for esterification of fatty acids in glyceryl esters with C1-C8 aliphatic alcohols in a tubular reactor. The method uses an expanded resin catalyst bed in the tubular reactor.Type: ApplicationFiled: April 30, 2009Publication date: November 5, 2009Inventors: Rajiv Manohar Banavali, Robert Tryon Hanlon, Aaron Sarafinas, Alfred Karl Schultz, Cheryl Irene Teich, Jose Antonio Trejo
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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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Publication number: 20040075079Abstract: The invention relates to compositions comprising an ester of a polyol and a mixture of fatty acids, wherein at least a part (I) of the esterified fatty acids has a chain length of 5-12 carbon atoms and another part (II) of the esterified fatty acids has a chain length of 16-22 carbon atoms, and wherein the composition has a viscosity of 7000 mm 2 /s or less, when tested according to ASTM (D2531). Such compositions have unexpected good low temperature properties, in particular a good rheology after having been kept for a prolonged time at a low temperature (e.g. at −30° C.). These compositions are suitable for use as (part of) hydraulic fluid in applications at low temperatures.Type: ApplicationFiled: September 26, 2003Publication date: April 22, 2004Applicant: UNICHEMA CHEMIE BVInventors: Thomas Friedrich Bunemann, Arie Dick Kardol, Abraham Comelis de Mooij
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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: 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: 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: 6121440Abstract: A process for preparing esterified polyol fatty acid polyesters is provided, where the polyol has n hydroxyl groups. The process provides for independent control of the level of fully esterified polyols, on the one hand, and the level of n-3 and lower esters, on the other hand. The process is especially suited for preparing sucrose polyester, wherein the process provides for independent control of the level of octaesters, on the one hand, and penta and lower level esters, on the other hand. The process can be used to reduce the level of undesirable reaction byproducts, such as difatty ketone and beta ketoester.Type: GrantFiled: February 12, 1998Date of Patent: September 19, 2000Assignee: The Procter & Gamble CompanyInventors: Corey James Kenneally, Gary Allen Busch, Patrick Joseph Corrigan, Eric Paul Granberg, John Keeney Howie, Richard Gerard Schafermeyer, James Earl Trout
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Patent number: 5770750Abstract: Phenolic aralkylation polymers modified by esterification with fatty acids, transesterification with glyceride oils, or other modifications to reactive hydroxyl moieties to improve the characteristics and properties of coating systems in which the modified materials are incorporated. At least a portion of the hydroxyl moieties of the polyol is esterified or otherwise modified. The hydroxyl moieties include those that have been "chain-extended," if desired.Type: GrantFiled: January 10, 1997Date of Patent: June 23, 1998Assignee: Georgia-Pacific Resins, Inc.Inventors: David A. Hutchings, Rajan Hariharan, Edward Lucas, Jr., Syed A. Elahi, Alan K. Randall, Kenneth Bourlier
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Patent number: 5523433Abstract: Disclosed is a process for making di(acyloxyalkyl) di(alkyl) ammonium compounds useful as fabric softeners. The corresponding di(hydroxyalkyl) tertiary amine is diesterified under conditions determined to minimize the formation of monoester side product and then the diester is quaternized under conditions effective to minimize degradation of the quaternized diester.Type: GrantFiled: September 29, 1994Date of Patent: June 4, 1996Assignee: Witco CorporationInventors: Christopher J. Toney, Phillip S. Welte, Robert K. Lagerman
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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: 5466719Abstract: Polyglycerol fatty acid ester mixtures of mono- di- and polyesters of polyglycerols having a degree of polymerization of 2 to 8 and at least one saturated and/or unsaturated fatty acid, the mixtures having an HLB of greater than 8 and containing 0 to less than 5 wt-% diglycerol fatty acid esters, 20 to 65 wt-% triglycerol fatty acid esters, 20 to 50 wt-% tetraglycerol fatty acid esters and 5 to 40 wt-% higher polyglycerol fatty acid esters, in which the fatty acid component consists of one or more fatty acids selected from the saturated and/or unsaturated, branched and/or unbranched C.sub.6 - to C.sub.14 -fatty acids containing less than 10 wt-% fatty acids having more than 14 carbon atoms; bath additive preparations containing such polyglycerol fatty acid ester mixtures; methods of using such polyglycerol fatty acid ester mixtures, and a process for preparing such mixtures.Type: GrantFiled: August 4, 1993Date of Patent: November 14, 1995Assignee: Solvay Fluor und Derivate GmbHInventors: Gerald Jakobson, Werner Siemanowski, Karl-Heinz Uhlig
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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: 5399729Abstract: Reduced calorie food compositions are prepared using fatty acid esterified alkoxylated polyol fat substitutes derived from C.sub.3 and higher epoxides and having a high proportion of primary ester linkages. The fat substitutes may be obtained by alkoxylation of a polyol such as glycerin with the epoxide in the presence of a cationic/ring-opening polymerization catalyst, followed by esterification with a fatty acid or a fatty acid equivalent.Type: GrantFiled: August 31, 1993Date of Patent: March 21, 1995Assignees: Arco Chemical Technology, L.P., CPC International Inc.Inventors: Charles F. Cooper, Stephen H. Harris
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Patent number: 5387705Abstract: A fast, three-stage, low temperature process for the conversion of fatty acids into food grade-anhydrides is disclosed. The process comprises as a first step the reaction of a higher fatty acid with a dehydrating agent under mild conditions. A second process step comprises the further conversion of mixed anhydrides to symmetrical anhydrides by continuous removal of the dehydrating agent and by-product acid from the reaction mixture under vacuum. In a third process step, the symmetrical anhydrides are purified under mild conditions, preferably using thin-film short path evaporation. The resulting anhydrides have minimal by-products and good color and odor.Type: GrantFiled: August 13, 1993Date of Patent: February 7, 1995Assignee: The Procter & Gamble CompanyInventors: Gordon K. Stipp, Bernard W. Kluesener
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Patent number: 5371253Abstract: Esterified alkoxylated mono- and diglycerides suitable for use as reduced calorie fat substitutes in food products may be produced by alkoxylating a tertiary alkyl partial ether of glycerin with an epoxide and then reacting the alkoxylated glycerin tertiary alkyl partial ether thereby obtained with a fatty acid under acid-catalyzed conditions. Separate deprotection and esterification steps are not required, resulting in a considerably streamlined process as compared to alternative methods of synthesizing alkoxylated fat substitutes having one or two fatty acid acyl groups attached directly to glycerin.Type: GrantFiled: December 14, 1993Date of Patent: December 6, 1994Assignee: Arco Chemical Technology, L.P.Inventor: Charles F. Cooper
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Patent number: 5288884Abstract: A convenient method of obtaining a reduced calorie esterified alkoxylated polyol containing both long chain saturated linear acyl groups and shorter chain unsaturated acyl groups is provided.Type: GrantFiled: October 22, 1992Date of Patent: February 22, 1994Assignees: Arco Chemical Technology, L.P., CPC International, Inc.Inventor: Charles F. Cooper
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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
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Patent number: 5142072Abstract: A process for the selective esterification of long chain length fatty acid monoglycerides, particularly monobehenin, with medium chain length fatty acid anhdyrides, particularly a mixture of C.sub.8 and C.sub.10 saturated fatty acid anhdyrides is disclosed. In this process, an at least about 60% pure C.sub.18 -C.sub.24 fatty acid monoglyceride or mixture thereof is esterified with an at least about 50% pure C.sub.6 -C.sub.10 fatty acid anhydride or mixture thereof at a temperature of from about 90.degree. to aobut 190.degree. C. in the substantial absence of an esterificastion catalyst. The mole ratio of fatty acid anhydride to monoglyceride used in this monoglyceride esterification is at least about 2:1.Type: GrantFiled: December 19, 1989Date of Patent: August 25, 1992Assignee: The Procter & Gamble CompanyInventors: Gordon K. Stipp, Bernard W. Kluesener
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Patent number: 5142071Abstract: A process for the selective esterification of long chain length fatty acid monoglycerides, particularly monobehenin, with medium chain length fatty acids, particularly a mixture of C.sub.8 and C.sub.10 saturated fatty acids, is disclosed. In this process, an at least about 60% pure C.sub.18 -C.sub.24 fatty acid monoglyceride or mixture thereof is esterified with an at least about 90% pure C.sub.6 -C.sub.10 fatty acid or mixture thereof at a temperature of from about 140.degree. to about 250.degree. C. in the substantial absence of an esterification catalyst. The mole ratio of fatty acid to monoglyceride used in this monoglyceride esterification is at least about 3:1. Water generated during this monoglyceride esterification is also continuously removed.Type: GrantFiled: December 19, 1989Date of Patent: August 25, 1992Assignee: The Procter & Gamble CompanyInventors: Bernard W. Kluesener, Gordon K. Stipp, David K. Yang
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Patent number: 5135683Abstract: An improved process for the hydrolysis and purification of an alkoxylated polyol containing a ketal protective functionality is described. The process may be employed to prepare reduced calorie esterified alkoxylated polyol fat mimetics useful in cooking and in food compositions.Type: GrantFiled: March 28, 1991Date of Patent: August 4, 1992Assignees: Arco Chemical Technology, L.P., CPC International Inc.Inventor: Charles F. Cooper
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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