Including Esterification Or Inter-esterification (e.g., Prior To, Simultaneously With, Or After Hydrogenation, Etc.) Patents (Class 554/142)
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Patent number: 10508251Abstract: One or more techniques are disclosed for a process of preparing a concentrated form of a vegetable-based stearic acid from a plant source. The process may comprise drying and deodorizing a vegetable based emulsion; and further concentrating the resulting fatty acid and triglyceride mix. The process may further comprise distillation of the resulting concentrated fatty acid and triglyceride mix, to separate the free fatty acids from the triglycerides. Additionally, the process may comprise fractional distillation of the free fatty acid distillate, to produce a concentrated from of the stearic acid, separating it from other fatty acids.Type: GrantFiled: January 18, 2019Date of Patent: December 17, 2019Assignee: MIG Acquisition LLCInventor: Eric E. Lofquist
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Patent number: 9957465Abstract: One or more techniques are disclosed for a process of preparing stearic acid from animal and/or plant sources may comprise: 1) deodorizing and distilling a fat; 2) concentrating fatty acids of the fat; and 3) hydrogenating the fatty acid to provide stearic acid. The process may include the use of co-products from plant and/or animal sources. The process may also include distilling the stearic acid to provide palmitic acid and/or fully hydrogenated fatty acid. Tallow fatty acid, vegetable fatty acid, stearic acid, and palmitic acid prepared from the process described are also disclosed.Type: GrantFiled: May 9, 2017Date of Patent: May 1, 2018Assignee: Magnus International Group, Inc.Inventor: Eric E. Lofquist
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Patent number: 8859795Abstract: The invention discloses a technology for producing ester of carboxylic acid using cellulosic biomass as starting material. This technology comprises the following key steps: converting all of the organic polymers, including such high molecular-weight polymers as carbohydrate components and lignin, in cellulosic biomass into water soluble, small molecular organics completely in relatively short time under relatively mild conditions; separating the resultant water soluble compounds containing aromatic rings by adjusting the acidity/basicity of the reaction solution or by using adsorption resin; and converting the water soluble compounds containing aromatic rings into ester of carboxylic acid by hydrogenation and esterification in a corresponding alcohol solution.Type: GrantFiled: September 22, 2009Date of Patent: October 14, 2014Assignee: Sun Pharmaceuticals, Inc.Inventors: Zuolin Zhu, Meg M. Sun, Chungao Su, Hongping Ye
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Patent number: 8841470Abstract: Chemically-modified fatty acids are prepared by reacting epoxidized fatty acids, their esters or triglyceride oils with amines of cyclic or aromatic hydrocarbons. The fatty acid derivatives produced are of the formula: wherein R is an H, branched or straight chain alkyl or alkenyl group, aromatic-containing group, glycerol, or glyceride, R? is a C3 to C29 aliphatic chain comprising one or more of the derivatized methylene groups of the formula: wherein R1 and R2 are independently selected from the group consisting of H, cyclic hydrocarbons, substituted cyclic hydrocarbons, and aryl groups, with the proviso that only one of said R1 and R2 may be H. These fatty acid derivatives have utility as antiwear/antifriction additives for industrial oils and automotive applications.Type: GrantFiled: August 24, 2011Date of Patent: September 23, 2014Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research FoundationInventors: Atanu Biswas, Kenneth M. Doll, Huai Nan Cheng, Brajendra K. Sharma
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Patent number: 8748641Abstract: A process for preparing saturated branched chain fatty acids or alkyl esters thereof involving subjecting unsaturated fatty acids having 10 to 25 carbon atoms, alkyl esters thereof or mixtures thereof to a skeletal isomerization reaction in the presence of water or a lower alcohol at a temperature of about 240° C. to about 280° C. using a combination of a stericly hindered Lewis base and zeolite as a Brönsted or Lewis acid catalyst, and isolating saturated branched chain fatty acids or alkyl esters thereof or mixtures thereof from the reaction mixture obtained by the skeletal isomerization reaction. The yield of said saturated branched chain fatty acids is ?70 wt %. The stericly hindered Lewis base is a tertiary amine or phosphine with linear or branched C1 to C6 alkyl or phenyl groups attached thereto.Type: GrantFiled: May 5, 2010Date of Patent: June 10, 2014Assignee: The United States of America, as represented by The Secretary of AgricultureInventors: Helen Ngo, Thomas A. Foglia
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Patent number: 8729283Abstract: A method comprising providing a starting composition comprising a polyunsaturated fatty acid, a polyunsaturated fatty ester, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated triglyceride, or a mixture thereof; self-metathesizing the starting composition or cross-metathesizing the starting composition with at least one short-chain olefin in the presence of a metathesis catalyst to form self-/cross-metathesis products comprising: cyclohexadiene; at least one olefin; and one or more acid-, ester-, or salt-functionalized alkene; and reacting cyclohexadiene to produce at least one cycloalkane or cycloalkane derivatives.Type: GrantFiled: January 15, 2013Date of Patent: May 20, 2014Assignee: Energy & Environmental Research Center FoundationInventor: Edwin S. Olson
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Publication number: 20130072705Abstract: This disclosure concerns methods for producing a high purity stearin comprising, for example, providing a sunflower oil comprising no more than about 4% total saturated fat and hydrogenating the sunflower oil. By way of further example, a method for producing a high purity tristearin may comprise providing sunflower oil comprising at least about 88% oleic acid and hydrogenating the sunflower oil. High purity stearin produced by methods, such as the foregoing, are also disclosed.Type: ApplicationFiled: November 2, 2012Publication date: March 21, 2013Applicant: DOW AGROSCIENCES LLCInventor: Dow AgroSciences LLC
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Publication number: 20120245367Abstract: The invention discloses a technology for producing ester of carboxylic acid using cellulosic biomass as starting material. This technology comprises the following key steps: converting all of the organic polymers, including such high molecular-weight polymers as carbohydrate components and lignin, in cellulosic biomass into water soluble, small molecular organics completely in relatively short time under relatively mild conditions; separating the resultant water soluble compounds containing aromatic rings by adjusting the acidity/basicity of the reaction solution or by using adsorption resin; and converting the water soluble compounds containing aromatic rings into ester of carboxylic acid by hydrogenation and esterification in a corresponding alcohol solution.Type: ApplicationFiled: September 22, 2009Publication date: September 27, 2012Applicants: China Fuel (Huaibei) Bioenergy Technology Development Co., Ltd., SUN PHARMACEUTICALS, INC.Inventors: Zuolin Zhu, Meg M. Sun, Chungao Su, Hongping Ye
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Publication number: 20110275844Abstract: A process for preparing saturated branched chain fatty acids or alkyl esters thereof involving subjecting unsaturated fatty acids having 10 to 25 carbon atoms, alkyl esters thereof or mixtures thereof to a skeletal isomerization reaction in the presence of water or a lower alcohol at a temperature of about 240° C. to about 280° C. using a combination of a stericly hindered Lewis base and zeolite as a Brönsted or Lewis acid catalyst, and isolating saturated branched chain fatty acids or alkyl esters thereof or mixtures thereof from the reaction mixture obtained by the skeletal-isomerization reaction. The yield of said saturated branched chain fatty acids is ?70 wt %. The stericly hindered Lewis base is a tertiary amine or phosphine with linear or branched C1 to C6 alkyl or phenyl groups attached thereto.Type: ApplicationFiled: May 5, 2010Publication date: November 10, 2011Inventors: Helen Ngo, Thomas A. Foglia
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Publication number: 20100029523Abstract: A lubricant from plant and/or animal oils and fats; a method for producing a lubricating oil, and the oil produced thereby. The lubricant comprises a diester produced by epoxidising an animal or plant fat or oil having an iodine number above about 7 and reacting the epoxidised oil or fat with a carboxylic acid anhydride in the presence of a basic catalyst.Type: ApplicationFiled: August 10, 2005Publication date: February 4, 2010Inventors: Herman Benecke, Bhima R. Vijayendran, Jeffrey Cafmeyer
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Patent number: 7252779Abstract: This invention is a composition that includes a transesterified fatty acid ester resulting from the reaction of a fatty acid ester, in the presence of an acid, with a hydroxyl-containing compound. The fatty acid esters of the invention are selected from those with a carbon number of eight to twenty. The hydroxyl-containing compound is an alcohol having a carbon number between one and eighteen. The resulting composition is useful as a lubricant, as a heat transfer agent, as a rheological modifier and as a corrosion/moisture inhibitor, among other uses.Type: GrantFiled: August 2, 2001Date of Patent: August 7, 2007Assignee: MJ Research Limited PartnershipInventors: Benjamin Mosier, Bryan J. Duffy
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Patent number: 7166730Abstract: The invention provides a novel process for the preparation of prostaglandins and analogues thereof, and new crystalline intermediates in the process.Type: GrantFiled: May 10, 2005Date of Patent: January 23, 2007Assignee: Fine Tech Laboratories, LtdInventors: Arie Gutman, Gennady Nisnevich, Marina Etinger, Igor Zaltzman, Lev Yudovich, Boris Pertsikov, Boris Tishin
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Patent number: 7157590Abstract: The present invention provides a new and effective process for the synthesis of 17-phenyl-18,19,20-trinor-PGF2? and its derivatives, including the anti-glaucoma drugs Bimatoprost and Latanoprost. The benefit of the present invention rises inter alia from the fact that a major intermediate involved in the synthesis of the above compounds may be isolated from a mixture containing also an undesired isomer, by crystallization. In addition, the undesired isomer may be oxidized to give the starting compound, which is then recycled.Type: GrantFiled: May 3, 2002Date of Patent: January 2, 2007Assignee: Finetech Laboratories Ltd.Inventors: Arie Gutman, Gennady Nisnevich, Marina Etinger, Igor Zaltzman, Lev Yudovitch, Boris Pertsikov
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Patent number: 6982340Abstract: There is provided a process wherein a lower alkyl ester of a fatty acid derived from natural fats and oils and a lower alcohol containing 1 to 4 carbon atoms is produced in a lower sulfur content at lower costs without causing a reduction in yield and a deterioration in selectivity, as well as a process for producing an alcohol without reducing the activity of a catalyst. The process comprises the step of adsorption treatment of an ester with at least one adsorbent selected from clay and activated carbon. Further are provided a process for producing an ester which further comprises adsorption treatment with a hydrogenating decomposition-type adsorbent containing Ni and/or Cu, in hydrogen or a mixed gas atmosphere of hydrogen and an inert gas, and a process for producing an alcohol which comprises hydrogenation reaction with an ester produced by any one of these processes as the starting material.Type: GrantFiled: March 11, 2003Date of Patent: January 3, 2006Assignee: Kao CorporationInventors: Taku Mumura, Hidetoshi Kadowaki, Futoshi Nishigaki
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Patent number: 6927300Abstract: Disclosed is a process for the preparation of the anti-glaucoma drug Latanoprost, in good yield, in large amounts and with desired purity. Also disclosed are novel intermediates for the above process.Type: GrantFiled: January 26, 2001Date of Patent: August 9, 2005Assignee: FineTech Laboratories LTDInventors: Arie Gutman, Gennadiy Nisnevich, Marina Etinger, Igor Zaltzman, Lev Judovich, Boris Pertsikov
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Patent number: 6720438Abstract: Disclosed is a process for the preparation of the anti-glaucoma drug Latanoprost, in good yield, in large amounts and with desired purity. Also disclosed are novel intermediates for the above process.Type: GrantFiled: October 25, 2002Date of Patent: April 13, 2004Assignee: FineTech Laboratories Ltd.Inventors: Arie Gutman, Gennadiy Nisnevich, Marina Etinger, Igor Zaltzman, Lev Judovich, Boris Pertsikov
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Patent number: 6610869Abstract: A process for making branched, substantially unsaturated ester oils involving: (a) providing an unsaturated C16-22 fatty acid; (b) dimerizing the unsaturated C16-22 fatty acid; (c) removing a monomer fraction accumulating during dimerization, the monomer fraction containing branched, substantially unsaturated fatty acids; (d) converting the branched, substantially unsaturated fatty acids contained in the monomer fraction into corresponding branched, substantially unsaturated fatty acid methyl esters having double bonds; (e) hydrogenating the branched, substantially unsaturated fatty acid methyl esters, with their double bonds intact, to form corresponding branched, substantially unsaturated fatty alcohols; and (f) esterifying the branched, substantially unsaturated fatty alcohols to form the branched, substantially unsaturated ester oils.Type: GrantFiled: June 4, 2002Date of Patent: August 26, 2003Assignee: Cognis Deutschland GmbH & Co. KGInventors: Norbert Huebner, Alfred Westfechtel
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Patent number: 6235915Abstract: A catalyst for hydrogenating aromatic compounds contained in feeds containing sulfur-containing compounds comprises platinum, palladium, fluorine and chlorine, on a support principally comprising alumina. This catalyst is of particular application to hydrogenating aromatic compounds with boiling points of more than 100° C. in hydrocarbon-containing feeds containing sulfur-containing compounds.Type: GrantFiled: May 6, 1999Date of Patent: May 22, 2001Assignee: Institut Francåis du PetroleInventors: Emmanuelle Guillon, Denis Uzio, Blaise Didillon
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Patent number: 6229056Abstract: The proposal is for unsaturated fatty substances with improved cold behavior obtained by (a) transesterifying a new low stearic (LS) sunflower oil with an oleic acid content of over 85 wt. % and a stearic acid content of under 3 wt. %, and (b) hydrogenating the resultant methyl esters in the prior art manner into the corresponding unsaturated fatty alcohols in the iodine number range from 90 to 100. The fatty substances are also distinguished by improved color and odor and are suitable for making fatty chemical products, e.g. alkoxylates, ether sulphates, sulphates and esters.Type: GrantFiled: May 8, 1997Date of Patent: May 8, 2001Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Achim Ansmann, Guenther Demmering, Georg Assmann, Fritz Schuster, Alfred Westfechtel, Michael Koehler
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Patent number: 5783247Abstract: Process for preparing a flavoring composition suitable as a butter flavor block by subjecting triglyceride fats, fatty acids or fatty acid derivatives to oxidizing conditions, comprising:(a) admixing an anti-oxidant to triglyceride fats, fatty acids or fatty acid derivatives at least to a concentration which is sufficient to increase the induction period of the fat by a factor of 1.5,(b) heating the mixture for 0.5 hours-1 week at 50.degree.-150.degree. C. under access of atmospheric oxygen and in the presence of water,under the condition that the triglyceride fats, fatty acids or fatty acid derivatives contain at least one poly-unsaturated fatty acid with an omega-3 non-conjugatable double bond system in an amount of >0.01 wt. %. Such fatty acids or derivatives of fatty acid are preferably obtained by partially hydrogenating a natural vegetable glyceride fat.Type: GrantFiled: December 28, 1995Date of Patent: July 21, 1998Assignee: Van Den Berg Foods Co., Division of Conopco, Inc.Inventors: Arnoldus Van Der Heijden, Graham Andrew Cross, Krijn Mostert, David Simon Bot, Matthias Berger
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Patent number: 5481025Abstract: Saturated, branched C.sub.20-28 fatty acids or esters thereof esterified with C.sub.1-36 alkanols produced by the process comprising: (a) reacting unsaturated fatty acids containing 18 to 22 carbon atoms and more than one olefinic bond or esters thereof esterified with C.sub.1-36 alkanols with ethylene at a temperature of from about 50.degree. C. to about 140.degree. C. and at a pressure of from about 5 to about 60 bar in the presence of transition metal compounds selected from the group consisting of Ru, Rh, Pd, Ir, or Pt wherein the molar ratio of ethylene to fatty acid or fatty acid ester is from about 1:1 to about 3:1 to form an olefinically unsaturated adduct and, (2) hydrogenating said adduct in the presence of a hydrogenation catalyst at a temperature of from about 70.degree. C. to about 120.degree. C. and under a hydrogen pressure of from 10 to about 30 bar.Type: GrantFiled: July 24, 1992Date of Patent: January 2, 1996Assignee: Henkel Kommanditgesellschaft auf Aktien TFP/PatentabteilungInventors: Alfred Laufenberg, Arno Behr
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Patent number: 5451667Abstract: Fumaric acid derivatives of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group or a metallic cation, andR.sub.2 is a saturated or unsaturated aliphatic C.sub.6 -C.sub.24 alkyl group, psoralen-9-yl, retinyl, .alpha.-tocopheryl (vitamin E), calciferyl, corticosteroid-21-yl or monosaccharid-.omega.-yl; a group of fumaric acid derivatives based on glycerol, alkane diol or polyol molecules; and fumaric acid derivatives of the formula ##STR2## wherein n is an integer from to 30 to 260,R.sub.3 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group,R.sub.4 is one of the R.sub.3 groups and n is the number of molecule repetitions, processes for their production and compositions containing same are described. These compounds are useful as drugs for the treatment of cryptogenically-caused diseases and have antisporiatic as well as antimicrobial action.Type: GrantFiled: October 8, 1992Date of Patent: September 19, 1995Inventors: Peter P. Speiser, Rajendra K. Joshi
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Patent number: 5401865Abstract: Saturated, branched C.sub.21-28 fatty acids or esters thereof esterified with C.sub.1-36 alkanols produced by the process comprising: (a) reacting unsaturated fatty acids containing 18 to 22 carbon atoms and more than one olefinic bond or esters thereof esterified with C.sub.1-36 alkanols with propylene at a temperature of from about 50.degree. C. to about 140.degree. C. and at a pressure of from about 5 to about 40 bar in the presence of transition metal compounds selected from the group consisting of Ru, Rh, Pd, Ir, or Pt wherein the molar ratio of propylene to fatty acid or fatty acid ester is from about 1:1 to about 2:1 to form an olefinically unsaturated adduct and, (2) hydrogenating said adduct in the presence of a hydrogenation catalyst at a temperature of from about 70.degree. C. to about 120.degree. C.Type: GrantFiled: July 23, 1992Date of Patent: March 28, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Alfred Laufenberg, Arno Behr
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Patent number: 5368776Abstract: A method for improving the corrosion inhibition of lubricating oils especially those of vegetable origin which comprises adding an efficient amount of the reaction product of an epoxidized fatty acid ester, especially an epoxidized methyl ester of an unsaturated fatty acid and a sulphonic acid and a process for producing these reaction products.Type: GrantFiled: October 20, 1993Date of Patent: November 29, 1994Assignee: Rhein Chemie Rheinau GmbHInventors: Volker Schafer, Robert Kohler, Alfred Pauli, Achim Fessenbecker
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Patent number: 5149695Abstract: Fumaric acid derivatives of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group or a metallic cation, andR.sub.2 is a saturated or unsaturated aliphatic C.sub.6 -C.sub.24 alkyl group, psoralen-9-yl, retinyl, .alpha.-tocopheryl (vitamin E), calciferyl, corticosteroid-21-yl or monosaccharid-.omega.-yl; a group of fumaric acid derivatives based on glycerol, alkane diol or polyol molecules; and fumaric acid derivatives of the formula ##STR2## wherein n is an integer from to 30 to 260,R.sub.3 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group,R.sub.4 is one of the R.sub.3 groups and n is the number of molecule repetitions, processes for their production and compositions containing same are described. These compounds are useful as drugs for the treatment of cryptogenically-caused diseases and have antisporiatic as well as antimicrobial action.Type: GrantFiled: March 13, 1989Date of Patent: September 22, 1992Inventors: Peter P. Speiser, Rajendra K. Joshi