Including Esterification Or Inter-esterification (e.g., Prior To, Simultaneously With, Or After Hydrogenation, Etc.) Patents (Class 554/142)
  • Patent number: 10508251
    Abstract: 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: Grant
    Filed: January 18, 2019
    Date of Patent: December 17, 2019
    Assignee: MIG Acquisition LLC
    Inventor: Eric E. Lofquist
  • Patent number: 9957465
    Abstract: 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: Grant
    Filed: May 9, 2017
    Date of Patent: May 1, 2018
    Assignee: Magnus International Group, Inc.
    Inventor: Eric E. Lofquist
  • Patent number: 8859795
    Abstract: 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: Grant
    Filed: September 22, 2009
    Date of Patent: October 14, 2014
    Assignee: Sun Pharmaceuticals, Inc.
    Inventors: Zuolin Zhu, Meg M. Sun, Chungao Su, Hongping Ye
  • Patent number: 8841470
    Abstract: 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: Grant
    Filed: August 24, 2011
    Date of Patent: September 23, 2014
    Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research Foundation
    Inventors: Atanu Biswas, Kenneth M. Doll, Huai Nan Cheng, Brajendra K. Sharma
  • Patent number: 8748641
    Abstract: 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: Grant
    Filed: May 5, 2010
    Date of Patent: June 10, 2014
    Assignee: The United States of America, as represented by The Secretary of Agriculture
    Inventors: Helen Ngo, Thomas A. Foglia
  • Patent number: 8729283
    Abstract: 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: Grant
    Filed: January 15, 2013
    Date of Patent: May 20, 2014
    Assignee: Energy & Environmental Research Center Foundation
    Inventor: Edwin S. Olson
  • Publication number: 20130072705
    Abstract: 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: Application
    Filed: November 2, 2012
    Publication date: March 21, 2013
    Applicant: DOW AGROSCIENCES LLC
    Inventor: Dow AgroSciences LLC
  • Publication number: 20120245367
    Abstract: 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: Application
    Filed: September 22, 2009
    Publication date: September 27, 2012
    Applicants: China Fuel (Huaibei) Bioenergy Technology Development Co., Ltd., SUN PHARMACEUTICALS, INC.
    Inventors: Zuolin Zhu, Meg M. Sun, Chungao Su, Hongping Ye
  • Publication number: 20110275844
    Abstract: 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: Application
    Filed: May 5, 2010
    Publication date: November 10, 2011
    Inventors: Helen Ngo, Thomas A. Foglia
  • Publication number: 20100029523
    Abstract: 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: Application
    Filed: August 10, 2005
    Publication date: February 4, 2010
    Inventors: Herman Benecke, Bhima R. Vijayendran, Jeffrey Cafmeyer
  • Patent number: 7252779
    Abstract: 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: Grant
    Filed: August 2, 2001
    Date of Patent: August 7, 2007
    Assignee: MJ Research Limited Partnership
    Inventors: Benjamin Mosier, Bryan J. Duffy
  • Patent number: 7166730
    Abstract: The invention provides a novel process for the preparation of prostaglandins and analogues thereof, and new crystalline intermediates in the process.
    Type: Grant
    Filed: May 10, 2005
    Date of Patent: January 23, 2007
    Assignee: Fine Tech Laboratories, Ltd
    Inventors: Arie Gutman, Gennady Nisnevich, Marina Etinger, Igor Zaltzman, Lev Yudovich, Boris Pertsikov, Boris Tishin
  • Patent number: 7157590
    Abstract: 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: Grant
    Filed: May 3, 2002
    Date of Patent: January 2, 2007
    Assignee: Finetech Laboratories Ltd.
    Inventors: Arie Gutman, Gennady Nisnevich, Marina Etinger, Igor Zaltzman, Lev Yudovitch, Boris Pertsikov
  • Patent number: 6982340
    Abstract: 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: Grant
    Filed: March 11, 2003
    Date of Patent: January 3, 2006
    Assignee: Kao Corporation
    Inventors: Taku Mumura, Hidetoshi Kadowaki, Futoshi Nishigaki
  • Patent number: 6927300
    Abstract: 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: Grant
    Filed: January 26, 2001
    Date of Patent: August 9, 2005
    Assignee: FineTech Laboratories LTD
    Inventors: Arie Gutman, Gennadiy Nisnevich, Marina Etinger, Igor Zaltzman, Lev Judovich, Boris Pertsikov
  • Patent number: 6720438
    Abstract: 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: Grant
    Filed: October 25, 2002
    Date of Patent: April 13, 2004
    Assignee: FineTech Laboratories Ltd.
    Inventors: Arie Gutman, Gennadiy Nisnevich, Marina Etinger, Igor Zaltzman, Lev Judovich, Boris Pertsikov
  • Patent number: 6610869
    Abstract: 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: Grant
    Filed: June 4, 2002
    Date of Patent: August 26, 2003
    Assignee: Cognis Deutschland GmbH & Co. KG
    Inventors: Norbert Huebner, Alfred Westfechtel
  • Patent number: 6235915
    Abstract: 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: Grant
    Filed: May 6, 1999
    Date of Patent: May 22, 2001
    Assignee: Institut Francåis du Petrole
    Inventors: Emmanuelle Guillon, Denis Uzio, Blaise Didillon
  • Patent number: 6229056
    Abstract: The proposal is for unsaturated fatty substances with improved cold behavior obtained by (a) transesterifying a new low stearic (LS) sunflower oil with an oleic acid content of over 85 wt. % and a stearic acid content of under 3 wt. %, and (b) hydrogenating the resultant methyl esters in the prior art manner into the corresponding unsaturated fatty alcohols in the iodine number range from 90 to 100. The fatty substances are also distinguished by improved color and odor and are suitable for making fatty chemical products, e.g. alkoxylates, ether sulphates, sulphates and esters.
    Type: Grant
    Filed: May 8, 1997
    Date of Patent: May 8, 2001
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Achim Ansmann, Guenther Demmering, Georg Assmann, Fritz Schuster, Alfred Westfechtel, Michael Koehler
  • Patent number: 5783247
    Abstract: 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: Grant
    Filed: December 28, 1995
    Date of Patent: July 21, 1998
    Assignee: Van Den Berg Foods Co., Division of Conopco, Inc.
    Inventors: Arnoldus Van Der Heijden, Graham Andrew Cross, Krijn Mostert, David Simon Bot, Matthias Berger
  • Patent number: 5481025
    Abstract: 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: Grant
    Filed: July 24, 1992
    Date of Patent: January 2, 1996
    Assignee: Henkel Kommanditgesellschaft auf Aktien TFP/Patentabteilung
    Inventors: Alfred Laufenberg, Arno Behr
  • Patent number: 5451667
    Abstract: 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: Grant
    Filed: October 8, 1992
    Date of Patent: September 19, 1995
    Inventors: Peter P. Speiser, Rajendra K. Joshi
  • Patent number: 5401865
    Abstract: 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: Grant
    Filed: July 23, 1992
    Date of Patent: March 28, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Alfred Laufenberg, Arno Behr
  • Patent number: 5368776
    Abstract: 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: Grant
    Filed: October 20, 1993
    Date of Patent: November 29, 1994
    Assignee: Rhein Chemie Rheinau GmbH
    Inventors: Volker Schafer, Robert Kohler, Alfred Pauli, Achim Fessenbecker
  • Patent number: 5149695
    Abstract: 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: Grant
    Filed: March 13, 1989
    Date of Patent: September 22, 1992
    Inventors: Peter P. Speiser, Rajendra K. Joshi