The -c(=o)o- Is Part Of An Ester Group Patents (Class 554/163)
  • Publication number: 20120178951
    Abstract: The invention relates to an apparatus for continuously carrying out heterogeneously catalyzed chemical reactions, comprising a microwave-transparent tube, the longitudinal axis of which extends in the direction of propagation of the microwaves of a single-mode microwave applicator and which is filled with an open-cell foam that carries or is made of catalytically active species.
    Type: Application
    Filed: September 3, 2010
    Publication date: July 12, 2012
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Matthias Krull, Roman Morschhaeuser, Hans-Juergen Scholz
  • Patent number: 8207362
    Abstract: A method of producing biodiesel from a source of triglycerides. The source of triglycerides is reacted with a blended alcohol composition in the presence of a catalyst to form a mixture of at least one fatty acid alcohol ester and glycerin. The fatty acid alcohol ester is then separated from the glycerin and is purified to produce a biofuel. The blended alcohol composition comprises at least one lower alcohol, a ketone and ethyl acetate. The use of the blended alcohol composition allows the transesterification process to proceed under ambient temperature and pressure conditions within a relatively short reaction time.
    Type: Grant
    Filed: November 21, 2008
    Date of Patent: June 26, 2012
    Assignee: Bio-Alternative, LLC
    Inventor: Martin Allan Morris
  • Patent number: 8202712
    Abstract: A process for producing triglycerides which comprises: (a) subjecting a first triglyceride comprising at least 40% by moles of oleic acid residues, based on total acyl groups in the triglyceride, to an alcoholysis reaction with an alcohol having from 1 to 6 carbon atoms to obtain a composition comprising 2-oleoyl monoglyceride and at least one acyl ester of said alcohol; (b) reacting the 2-oleoyl monoglyceride with an acylating agent comprising at least one C12 to C24 saturated fatty acid, at least one ester of said fatty acid or a mixture thereof, to obtain a 1,3-saturated fatty acid acyl 2-oleoyl glyceride; and (c) separating at least a part of the at least one acyl ester after or during step (a) or step (b); (d) reacting the acyl ester with a second glyceride to form 1,3-dioleoyl 2-palmitoyl glyceride.
    Type: Grant
    Filed: September 8, 2006
    Date of Patent: June 19, 2012
    Assignee: Loders Croklaan B.V.
    Inventors: John Bernard Harris, Ulrike Schmid, Frederick William Cain
  • Patent number: 8183021
    Abstract: A process for producing triglycerides comprises: (a) subjecting a first triglyceride comprising at least 40% by moles of oleic acid residues, based on total acyl groups in the triglyceride, to a reaction with stearic acid, at least one ester of stearic acid or a mixture thereof, to obtain a composition comprising 1,3-distearoyl 2-oleoyl glyceride and trioleoyl glyceride; (b) treating the composition to form a first fraction having an increased amount by weight of oleoyl groups compared to said composition and a second fraction having an increased amount by weight of stearoyl groups compared to said composition; (c) hydrolysing the first fraction to form oleic acid; and (d) reacting said oleic acid or an ester thereof with a triglyceride comprising at least 50% by moles of palmitic acid residues, based on total acyl groups, to form a composition comprising 1,3-dioleoyl 2-palmitoyl glyceride.
    Type: Grant
    Filed: September 8, 2006
    Date of Patent: May 22, 2012
    Assignee: Loders Croklaan B.V.
    Inventors: Frederick William Cain, Ulrike Schmid
  • Patent number: 8182556
    Abstract: A method for producing biofuels is provided. A method of making biofuels includes dewatering substantially intact algal cells to make an algal biomass, sequentially adding solvent sets to the algal biomass, and sequentially separating solid biomass fractions from liquid fractions to arrive at a liquid fraction comprising neutral lipids. The method also includes esterifying the neutral lipids, separating a water miscible fraction comprising glycerin from a water immiscible fraction comprising fuel esters, carotenoids, and omega-3 fatty acids. The method also includes obtaining a C16 or shorter fuel esters fraction, a C16 or longer fuel ester fraction, and a residue comprising carotenoids and omega-3 fatty acids. The method includes hydrogenating and deoxygenating at least one of (i) the C16 or shorter fuel esters to obtain a jet fuel blend stock and (ii) the C16 or longer fuel esters to obtain a diesel blend stock.
    Type: Grant
    Filed: October 7, 2011
    Date of Patent: May 22, 2012
    Assignee: Haliae Development, LLC
    Inventor: Aniket Kale
  • Patent number: 8178706
    Abstract: 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: Grant
    Filed: September 8, 2008
    Date of Patent: May 15, 2012
    Assignee: Aalto University Foundation
    Inventors: Ossi Pastinen, Simo Laakso, Sanna Hokkanen, Marjatta Vahvaselkä
  • Publication number: 20120116043
    Abstract: Methods of one-pot synthesis of high molecular weight natural oil polyols having a functionality of at least two are provided. The resultant polyols may be directly reacted with polyisocyanates to produce polyurethanes.
    Type: Application
    Filed: December 16, 2011
    Publication date: May 10, 2012
    Inventors: Thomas M Garrett, Xian Xian Du
  • Publication number: 20120116042
    Abstract: Methods of one-pot synthesis of high molecular weight natural oil polyols having a functionality of between about 4 and about 8 are provided. The resultant polyols may be directly reacted with polyisocyanates to produce polyurethanes.
    Type: Application
    Filed: December 16, 2011
    Publication date: May 10, 2012
    Inventors: Thomas M Garrett, Xian Xian Du
  • Publication number: 20120100073
    Abstract: Fatty acid analogue (FAA) molecules comprising positron-emitting radionuclides, salts thereof, and FAA-triglycerides are disclosed. Also disclosed are methods of synthesis, and methods of imaging distribution and metabolism of fatty acids and fatty acid triglycerides.
    Type: Application
    Filed: May 4, 2010
    Publication date: April 26, 2012
    Applicant: WASHINGTON UNIVERSITY
    Inventors: Robert H. Mach, Robert John Gropler, Zhude Tu, Pilar Herrero
  • Patent number: 8152870
    Abstract: A method for producing biofuels is provided. A method of making biofuels includes dewatering substantially intact algal cells to make an algal biomass, sequentially adding solvent sets to the algal biomass, and sequentially separating solid biomass fractions from liquid fractions to arrive at a liquid fraction comprising neutral lipids. The method also includes esterifying the neutral lipids, separating a water miscible fraction comprising glycerin from a water immiscible fraction comprising fuel esters, carotenoids, and omega-3 fatty acids. The method also includes obtaining a C16 or shorter fuel esters fraction, a C16 or longer fuel ester fraction, and a residue comprising carotenoids and omega-3 fatty acids. The method includes hydrogenating and deoxygenating at least one of (i) the C16 or shorter fuel esters to obtain a jet fuel blend stock and (ii) the C16 or longer fuel esters to obtain a diesel blend stock.
    Type: Grant
    Filed: April 6, 2011
    Date of Patent: April 10, 2012
    Assignee: Heliae Development, LLC
    Inventor: Aniket Kale
  • Patent number: 8153407
    Abstract: A process for the production of a composition comprising 1,3-dioleyl-2-palmitoyl glyceride (OPO) comprises subjecting a palm oil stearin, with an iodine value (IV) between about 2 and about 12 to enzymic transesterification, with oleic acid or a non-glyceride ester thereof.
    Type: Grant
    Filed: September 8, 2006
    Date of Patent: April 10, 2012
    Assignee: Loders Croklaan B.V.
    Inventors: Erik Johannes Anton Schweitzer, Frederick William Cain, Ulrike Schmid
  • Publication number: 20120065260
    Abstract: Compounds of formula (I); wherein R1 and R2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl DHA, alpha-methyl DHA methyl ester, alpha-methyl DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed.
    Type: Application
    Filed: September 6, 2011
    Publication date: March 15, 2012
    Inventors: Morten Bryhn, Jan Kopecky, Anne Kristin Holmeide
  • Patent number: 8119824
    Abstract: As means for producing a biodiesel oil from a feed oil containing a free fatty acid at high efficiency, the following processes (1) to (3) are provided: (1) a process for producing a higher fatty acid ester, comprising reacting a lower alcohol with a higher fatty acid in the presence of an amorphous carbon having a sulfonate group introduced therein, thereby producing the higher fatty acid ester; (2) a process for producing a higher fatty acid ester, comprising reacting a lower alcohol with a higher fatty acid and a higher fatty acid triglyceride in the presence of an amorphous carbon having a sulfonate group introduced therein, thereby producing the higher fatty acid ester by both of the reaction between the lower alcohol and the higher fatty acid and the reaction between the lower alcohol and the higher fatty acid triglyceride; and (3) a process for producing a higher fatty acid ester, comprising: reacting a lower alcohol with a higher fatty acid and a higher fatty acid triglyceride in the presence of an am
    Type: Grant
    Filed: June 20, 2006
    Date of Patent: February 21, 2012
    Assignee: Tokyo Institute of Technology
    Inventor: Michikazu Hara
  • Patent number: 8093416
    Abstract: The present invention has an object to provide the following method for producing fatty acid alkyl esters and/or glycerin and the following catalyst used in the production method. According to the production method, a fat or oil is reacted with an alcohol to give a fatty acid alkyl ester and/or glycerin suitably used in a food or fuel application, etc., with high efficiency, and complicated steps such as a step of recovering a catalyst can be simplified or omitted. According to the catalyst, an active metal component is not eluted even if the catalyst is used repeatedly or for a long period of time, and further, such a catalyst can maintain an excellent catalyst activity for a long time even in the presence of water and exhibit a high activity to both of transesterification of a glyceride contained in the fat or oil and esterification of free fatty acid.
    Type: Grant
    Filed: October 17, 2008
    Date of Patent: January 10, 2012
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Takeo Akatsuka, Masanori Nonoguchi, Tomoharu Oku
  • Publication number: 20110312044
    Abstract: In an alcohol fermentation process, oil derived from biomass is chemically converted into an extractant available for in situ removal of a product alcohol such as butanol from a fermentation broth. The glycerides in the oil can be chemically converted into a reaction product, such as fatty acids, fatty alcohols, fatty amides, fatty acid methyl esters, fatty acid glycol esters, and hydroxylated triglycerides, and mixtures thereof, which forms a fermentation product extractant having a partition coefficient for a product alcohol greater than a partition coefficient of the oil of the biomass for the product alcohol. Oil derived from a feedstock of an alcohol fermentation process can be chemically converting into the fermentation product extractant.
    Type: Application
    Filed: June 17, 2011
    Publication date: December 22, 2011
    Applicant: BUTAMAX(TM) ADVANCED BIOFUELS LLC
    Inventors: DOUGLAS ROBERT ANTON, JELENA CIRAKOVIC, BRUCE A. DINER, MICHAEL CHARLES GRADY, FRANCIS J. WOERNER
  • Patent number: 8071799
    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 29, 2009
    Date of Patent: December 6, 2011
    Assignee: Energy & Environmental Research Center Foundation
    Inventor: Edwin S. Olson
  • Publication number: 20110295027
    Abstract: Catalytic isomerisation of fatty acid esters to form branched fatty acid esters comprises the steps of contacting a feedstock having at least one fatty acid ester with a catalyst and isolating from other reaction products branched fatty acid esters that are produced. The catalyst is a crystalline porous silicoaluminophosphate catalyst having silicon, aluminum, and phosphorous atoms in lattice framework positions. The branched fatty acid esters formed thereby demonstrate properties suitable for use in various applications.
    Type: Application
    Filed: June 1, 2011
    Publication date: December 1, 2011
    Applicant: UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC.
    Inventors: Paul Ratnasamy, Moises A. Carreon
  • Patent number: 8034842
    Abstract: Compounds of formula (I); wherein R1 and R2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl-DHA, alpha-methyl DHA methyl ester, alpha-methyl-DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed.
    Type: Grant
    Filed: April 29, 2008
    Date of Patent: October 11, 2011
    Assignee: Pronova BioPharma Norge AS
    Inventors: Morten Bryhn, Jan Kopecky, Anne Kristin Holmeide
  • Patent number: 8013088
    Abstract: A polymerization reaction mixture for the cationic polymerization of unsaturated biological oils (e.g. vegetable oils and animals oils) based on the cationic reaction of double bonds initiated by superacids is provided. The polymerized oils have a viscosity about 10 to 200 times higher than the initial oil and relatively high unsaturation (only about 10-30% lower than that of initial oils).
    Type: Grant
    Filed: March 9, 2009
    Date of Patent: September 6, 2011
    Assignee: Pittsburg State University
    Inventors: Mihail Ionescu, Zoran S. Petrovic
  • Publication number: 20110213040
    Abstract: A method of producing volatilized fatty acids by heating a feedstock comprising at least one fat or oil in a reactor under inert vacuum to volatilize fatty acids, and removing volatilized fatty acids from bottoms residue comprising cross-linked oil. A system for stripping fatty acids from triglycerides, the system comprising a reactor, heating apparatus and a vacuum pump capable of pulling a vacuum in the range of from 1 kPa to 50 kPa on the reactor. A system for producing a hydrogenated product including a reactor comprising an inlet for a stream comprising triglycerides, an outlet for volatilized fatty acids, and an outlet for a cross-linked product, heating apparatus, a vacuum pump capable of pulling a vacuum in the range of from 1 kPa to 50 kPa on the reactor, and a hydrogenation reactor, wherein an inlet of the hydrogenation reactor is fluidly connected to the outlet for cross-linked product.
    Type: Application
    Filed: May 10, 2011
    Publication date: September 1, 2011
    Applicant: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Publication number: 20110200731
    Abstract: A tube reactor having a substantially tubular body portion including a conical section, an entry port, an opposing exit port, and an axis extending between the ports through the body portion. The tubular body portion being rotatable about the axis. At least one reactant can be fed into the tubular body portion and directed toward the conical section. An inner surface of the tubular body portion receives the reactants from the conical section, and processes the reactants. An insert may be positioned within the tubular body portion to further process the reactants along the inner surface. A rotating reservoir having a damper can be coupled to the rotating tubular body portion. The damper receives the processed reactants from the inner surface of the tubular body portion, and guides the processed reactants into the rotating reservoir to minimize turbulence. The rotating reservoir then separates the processed reactants by density.
    Type: Application
    Filed: January 21, 2011
    Publication date: August 18, 2011
    Inventor: ROSHAN JACHUCK
  • Patent number: 7989411
    Abstract: The present invention relates to a composition which contains a mixture of alkoxylated mono-, di-, and triglycerides and glycerine of formula wherein R? represents H or CH3, and each one of m, n, or l represents, independently, a number from 0 to 20, the sum of m, n, and l being in the range of 1.5 to 20, characterized in that in the acyl group represented by —CO—R, R represents an alkyl or alkenyl group, linear or branched, of 6 to 11 carbon atoms, and the proportion by weight (i)+(ii)+(iii)/(iv) is in the range of 2.0:0.5 to 0.5:3; and to a method for the preparation of said composition, the detergent compositions which contain said compositions, and the use of said composition as surfactant or co-surfactant in the detergent compositions, particularly in detergent compositions, especially, but not exclusively, suitable for washing fabrics, suitable for manual dishwashing, for washing the hair or for personal hygiene.
    Type: Grant
    Filed: April 3, 2007
    Date of Patent: August 2, 2011
    Assignee: Kao Corporation, S.A.
    Inventors: Carmen Ma Pey Gutiérrez, Blanca Nogués López, Maria José Bermejo Osés, Hiroshi Abe
  • Publication number: 20110174734
    Abstract: The development and application of a novel non-polar oil recovery process utilizing a non-dispersive solvent extraction method to coalesce and recover oil from a bio-cellular aqueous slurry is described herein. The process could apply to recovery of algal oil from a lysed algae slurry, recovery of Omega fatty acids from a bio-cellular aqueous feed, recovery of Beta-carotene from a bio-cellular aqueous feed and for the removal from produced water in oil production and similar type applications. The technique of the present invention utilizes a microporous hollow fiber (MHF) membrane contactor. The novel non-polar oil recovery process described herein can be coupled to a collecting fluid (a non-polar solvent such as heptane, a biodiesel mixture or the previously extracted oil) that is circulated through the hollow fiber membrane. In cases where the biodiesel mixture or the previously extracted oil is used the solvent recovery step (e.g. distillation) can be eliminated.
    Type: Application
    Filed: January 13, 2011
    Publication date: July 21, 2011
    Applicant: Board of Regents, The University of Texas System
    Inventors: Frank Seibert, Martin Poenie
  • Publication number: 20110136188
    Abstract: The present invention provides a novel approach for the preparation of fatty alcohol esters of ?-hydroxy carboxylic acids. In one form of the invention, the target fatty alcohol ester of ?-hydroxy carboxylic acid is produced by converting a lower alkyl ester of ?-hydroxy carboxylic acid into a fatty alcohol ester of ?-hydroxy carboxylic acid via alcoholysis (i.e., transesterification). The transesterification process is an equilibrium reaction, catalyzed chemically (i.e., with acids or bases) or enzymatically, that is shifted in the desired direction to produce the desired product. One preferred way of shifting the reaction in the direction of the desired product is by reducing the concentration of one of the products (e.g., distillation of a lower-boiling alcohol as soon as it is formed). Another preferred way of shifting the reaction in the direction of the desired product is by increasing the concentration of one of the reactants (e.g., adding more of the starting ester).
    Type: Application
    Filed: November 24, 2010
    Publication date: June 9, 2011
    Inventors: Gerald S. Jones, JR., Scott A. Goodrich, Joseph P. St. Laurent
  • Publication number: 20110098356
    Abstract: The present invention includes methods for producing and purifying esters of polyunsaturated fatty acids that include reacting a composition having triglycerides with polyunsaturated fatty acid residues in the presence of an alcohol and a base to produce an ester of a polyunsaturated fatty acid from the triglycerides. The composition can be a polyunsaturated fatty acid-containing composition that has not been conventionally processed. The reacted composition can be further processed by distillation.
    Type: Application
    Filed: December 29, 2009
    Publication date: April 28, 2011
    Applicant: MARTEK BIOSCIENCES CORPORATION
    Inventors: Neil Leininger, Chris Luigart, Krishna Raman, Jung Lee
  • Publication number: 20110092725
    Abstract: A process that employs hydrolysis of fats and oils as a pretreatment step to prevent or drastically reduce the formation of glycerin decomposition products that occur in systems that use fixed bed or heterogeneous catalysts for simultaneous trans-esterification and esterification of fats and oils to alkyl esters of fatty acids for use as Biofuels, soaps, detergents, solvents or other applications of fatty acid alkyl esters. The pretreatment step is particularly effective for processes using fixed bed catalytic reactors operating at elevated temperatures and pressures sufficient to cause formation of decomposition products of glycerin which is known to be a problem associated with these processes. The pretreatment hydrolysis step allows the formation, separation and recovery of better quality glycerin by-product and minimizing the formation of glycerin decomposition products in the reactors.
    Type: Application
    Filed: October 19, 2009
    Publication date: April 21, 2011
    Applicant: Lurgi PSI, Inc.
    Inventor: Ray Jones
  • Publication number: 20110071309
    Abstract: Systems and methods are disclosed for generating a proton removing agent and an acidic solution in a low voltage electrochemical system and utilizing the proton removing agent to sequester carbon dioxide from a waste gas in a carbon dioxide sequestration system and utilizing the acidic solution to catalyze at least one step of a chemical syntheses in combination with a plant based material.
    Type: Application
    Filed: September 23, 2010
    Publication date: March 24, 2011
    Inventors: Brent R. CONSTANTZ, Brian Curtis
  • Patent number: 7906664
    Abstract: The invention relates to polyglycerol partial esters of polyricinoleic acid and polyfunctional carboxylic acids, obtainable by esterification of a a) polyglycerol mixture with b) at least one polyricinoleic acid and c) at least one di- and/or tricarboxylic acid and optionally d) at least one fatty acid having 6 to 22 carbon atoms by methods known per se, and to the use thereof for producing cosmetic or pharmaceutical emulsions or dispersions.
    Type: Grant
    Filed: January 19, 2006
    Date of Patent: March 15, 2011
    Assignee: Evonik Goldschmidt GmbH
    Inventors: Petra Allef, Wolfgang Berkels, Hannelore Fötsch, Jürgen Meyer
  • Patent number: 7906663
    Abstract: In order to produce both an olefinic fraction and a composition of diacids or diesters of fats, a process is carried out which comprises, in succession: a) metathesis of an unsaturated fat with ethylene in the presence of at least one non-aqueous ionic liquid; b) separating and recycling the ionic liquid used in the first step; c) separating, by distillation, the olefinic fraction (fraction A) from the unsaturated fat mono-ester or mono-basic acid fraction (fraction B) formed in step a); d) homometathesis of the mono-unsaturated fat ester or acid cut (fraction B) which allows the co-production of unsaturated fat diesters or diacids (fraction C) and ethylene which is recycled to the first methathesis step of the process; and e) optionally, recycling the ionic liquid containing the catalyst used in step d).
    Type: Grant
    Filed: January 23, 2007
    Date of Patent: March 15, 2011
    Assignee: IFP Energies Nouvelles
    Inventors: Hélène Olivier-Bourbigou, Christophe Vallee, Gérard Hillion
  • Publication number: 20100286420
    Abstract: The present invention has an object to provide the following method for producing fatty acid alkyl esters and/or glycerin and the following catalyst used in the production method. According to the production method, a fat or oil is reacted with an alcohol to give a fatty acid alkyl ester and/or glycerin suitably used in a food or fuel application, etc., with high efficiency, and complicated steps such as a step of recovering a catalyst can be simplified or omitted. According to the catalyst, an active metal component is not eluted even if the catalyst is used repeatedly or for a long period of time, and further, such a catalyst can maintain an excellent catalyst activity for a long time even in the presence of water and exhibit a high activity to both of transesterification of a glyceride contained in the fat or oil and esterification of free fatty acid.
    Type: Application
    Filed: October 17, 2008
    Publication date: November 11, 2010
    Applicant: Nippon Shokubai Co., Ltd.
    Inventors: Takeo Akatsuka, Masanori Nonoguchi, Tomoharu Oku
  • Patent number: 7828978
    Abstract: Simultaneous synthesis and purification of a fatty acid monoester biodiesel fuel from a triacylglycerol feedstock is described. In an exemplary method, the triacylglycerol feedstock is continuously contacted with a catalytic chromatographic bed comprising a first (solid phase) basic catalyst through a first port of a simulated moving bed chromatographic apparatus. A monohydric alcohol and optional second (mobile phase) basic catalyst is continuously contacted with the catalytic chromatographic bed through a second port and pumped in a first direction toward the triacylglycerol feedstock to contact the triacylglycerol in a reaction zone of the catalytic chromatographic bed where the fatty acid monoester and glycerol coproduct are formed. The fatty acid monoester is removed from the reaction zone through a product port of the simulated moving bed apparatus.
    Type: Grant
    Filed: June 8, 2006
    Date of Patent: November 9, 2010
    Inventors: Doug Geier, John G. Soper
  • Publication number: 20100261921
    Abstract: The present invention relates to an integrated method and system for the simultaneous production of biodiesel from free fatty acids (via esterification) and from triglycerides (via transesterification) within the same reaction chamber. More specifically, one preferred embodiment of the invention relates to a method and system for the production of biodiesel using an electrodeionization stack, wherein an ion exchange resin matrix acts as a heterogeneous catalyst for simultaneous esterification and transesterification reactions between a feedstock and a lower alcohol to produce biodiesel, wherein the feedstock contains significant levels of free fatty acid. In addition, because of the use of a heterogeneous catalyst, the glycerol and biodiesel have much lower salt concentrations than raw biodiesel produced by conventional transesterification processes. The present invention makes it much easier to purify glycerol and biodiesel.
    Type: Application
    Filed: April 26, 2010
    Publication date: October 14, 2010
    Inventors: YuPo J. Lin, Edward J. St. Martin
  • Publication number: 20100222606
    Abstract: The present invention relates to a method of producing pure or enriched bisabolol by separating substance mixtures comprising bisabolol and farnesol by selective esterification of farnesol and subsequent distillative separation. The invention relates specifically to a method as specified above comprising the selective transesterification of mixtures comprising formyl-bisabolol and formyl-farnesol and subsequent distillative separation. The present invention furthermore relates to a method of producing farnesol esters.
    Type: Application
    Filed: January 12, 2007
    Publication date: September 2, 2010
    Applicant: BASF SE
    Inventors: Hansgeorg Ernst, Klaus-Peter Pfaff, Karl Beck, Jürgen Schubert, Günther Gottwald, Wolfgang Krause
  • Publication number: 20100217022
    Abstract: Enhanced oligomeric polyols are reported. The enhanced oligomeric polyols may be prepared by a method comprising the steps of: (a) providing an oligomeric polyol that comprises at least one glycerol fatty acid ester having at least one glycerol fatty acid ester bond; wherein at least 5% of the ethyldenyl groups (*C?C*) in the glycerol fatty acid ester are substituted with a bonding structure selected from the group consisting of: C—*C—C*—C; O—*C—C*—O; C?*C—C*—C, and mixtures thereof, where * is used to denote the original carbon atoms in the ethylidenyl group; and (b) cleaving at least a portion of the glycerol fatty acid ester bonds to form the enhanced oligomeric polyol. The enhanced oligomeric polyols are useful in making polymers such as polyurethanes.
    Type: Application
    Filed: April 27, 2007
    Publication date: August 26, 2010
    Inventors: Timothy W. Abraham, Jeff Malsam, Xiuguang A. Guo, Milhail Ionescu, Ivan J. Javni, Zoran S. Petrovic
  • Patent number: 7662982
    Abstract: Process of making alkyl-capped alkoxylated esters. More specifically, a process of making alkyl-capped alkoxylated esters that are comprised substantially of triethylene alkoxy ester and substantially free from ethylene glycol monoalkoxy monoester and diethylene glycol monoalkoxy monoester.
    Type: Grant
    Filed: March 28, 2006
    Date of Patent: February 16, 2010
    Assignee: The Procter & Gamble Company
    Inventors: Lon Montgomery Gray, Jeffrey John Scheibel, Phillip Kyle Vinson, Christopher James Binski
  • 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: 7553982
    Abstract: A method of producing biodiesel from a source of triglycerides. The source of triglycerides is reacted with a blended alcohol composition in the presence of a catalyst to form a mixture of at least one fatty acid alcohol ester and glycerin. The fatty acid alcohol ester is then separated from the glycerin and is purified to produce a biofuel. The blended alcohol composition comprises at least one lower alcohol, a ketone and ethyl acetate. The use of the blended alcohol composition allows the esterfication process to proceed under ambient temperature and pressure conditions within a relatively short reaction time.
    Type: Grant
    Filed: August 13, 2007
    Date of Patent: June 30, 2009
    Assignee: Bio-Alternative, LLC
    Inventor: Martin Allan Morris
  • Publication number: 20090156845
    Abstract: The invention relates to acrylate modified, natural fatty acid based hybride polymers, and to a method for their preparation. The invention also relates to the use of the modified natural fatty acid based hybride polymers as binding agents especially in water based coatings, adhesives and composites and as environmentally friendly wood impregnating agents. The acrylate-modified natural fatty acid based hybride polymer is a block polymer formed of acrylate segments and fatty acid segments.
    Type: Application
    Filed: March 2, 2007
    Publication date: June 18, 2009
    Applicant: Valtion teknillinen tutkimuskesus
    Inventors: Nina Heiskanen, Pia Willberg, Salme Koskimies, Janne Hulkko, Pirita Ushanov, Sirkka-Liisa Maunu
  • Publication number: 20090131700
    Abstract: 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: Application
    Filed: September 8, 2008
    Publication date: May 21, 2009
    Applicant: Helsinki University of Technology
    Inventors: Ossi Pastinen, Simo Laakso, Sanna Hokkanen, Marjatta Vahvaselka
  • Publication number: 20090123982
    Abstract: A process for producing triglycerides which comprises: (a) subjecting a first triglyceride comprising at least 40% by moles of oleic acid residues, based on total acyl groups in the triglyceride, to an alcoholysis reaction with an alcohol having from 1 to 6 carbon atoms to obtain a composition comprising 2-oleoyl monoglyceride and at least one acyl ester of said alcohol; (b) reacting the 2-oleoyl monoglyceride with an acylating agent comprising at least one C12 to C24 saturated fatty acid, at least one ester of said fatty acid or a mixture thereof, to obtain a 1,3-saturated fatty acid acyl 2-oleoyl glyceride; and (c) separating at least a part of the at least one acyl ester after or during step (a) or step (b); (d) reacting the acyl ester with a second glyceride to form 1,3-dioleoyl 2-palmitoyl glyceride.
    Type: Application
    Filed: September 8, 2006
    Publication date: May 14, 2009
    Inventors: John Bernard Harris, Ulrike Schmid, Frederick William Cain
  • Patent number: 7501479
    Abstract: A method for the cationic polymerization of unsaturated biological oils (e.g., vegetable oils and animal oils) based on the cationic reaction of double bonds initiated by superacids is provided. The process occurs under very mild reaction conditions (about 70-110° C. and atmospheric pressure) and with short reaction times. The polymerized oils have a viscosity about 10 to 200 times higher than the initial oil and relatively high unsaturation (only about 10-30% lower than that of initial oils).
    Type: Grant
    Filed: May 7, 2007
    Date of Patent: March 10, 2009
    Assignee: Pittsburg State University
    Inventors: Mihail Ionescu, Zoran S. Petrovic
  • Publication number: 20080300306
    Abstract: Compounds of formula (I); wherein R1 and R2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl-DHA, alpha-methyl DHA methyl ester, alpha-methyl-DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed.
    Type: Application
    Filed: April 29, 2008
    Publication date: December 4, 2008
    Inventors: Morten Bryhn, Jan Kopecky, Anne Kristin Holmeide
  • Publication number: 20080281071
    Abstract: A method for the cationic polymerization of unsaturated biological oils (e.g., vegetable oils and animal oils) based on the cationic reaction of double bonds initiated by superacids is provided. The process occurs under very mild reaction conditions (about 70-110° C. and atmospheric pressure) and with short reaction times. The polymerized oils have a viscosity about 10 to 200 times higher than the initial oil and relatively high unsaturation (only about 10-30% lower than that of initial oils).
    Type: Application
    Filed: May 7, 2007
    Publication date: November 13, 2008
    Inventors: Mihail Ionescu, Zoran S. Petrovic
  • Patent number: 7420072
    Abstract: A continuous method and apparatus for making biodiesel fuel from glycerides such as vegetable oil employs a two-stage reactor provided with recycle. Yields of 95% and greater are readily achieved in a continuous mode of operation.
    Type: Grant
    Filed: April 26, 2007
    Date of Patent: September 2, 2008
    Assignee: Orbitek, Inc.
    Inventor: Christian A. Fleisher
  • Publication number: 20080206820
    Abstract: The present invention provides methods for labeling One or two oxygen atom(s) in a carboxyl group of a carboxyl-containing compound with an oxygen isotope selected from oxygen-17 (17O) or oxygen-18 (18O). The methods of the present invention are characterized in that an activated ester of the carboxyl-containing compound (carboxylic acid) is reacted with H217O or H218O in the presence of an activator. In the methods of the present invention, the reaction between the activated ester of a carboxylic acid and H217O or H218O can be allowed to proceed without including drastic conditions such as strongly acidic conditions or alkaline hydrolysis because an activator is used.
    Type: Application
    Filed: May 20, 2005
    Publication date: August 28, 2008
    Inventors: Shigeyuki Yokoyama, Kazuhiko Yamada, Toshio Yamazaki
  • Publication number: 20080182901
    Abstract: This invention is directed to a crystalline acid of a lipoxin A4 analog of Formula (II): wherein: R1 is —O—, —S(O)t— (where t is 0, 1 or 2), or a straight or branched alkylene chain; and R2 is aryl (optionally substituted by one or more substituents selected from alkyl, alkoxy, halo, haloalkyl and haloalkoxy) or aralkyl (optionally substituted by one or more substituents selected from f alkyl, alkoxy, halo, haloalkyl and haloalkoxy); and wherein the compound of Formula (II) is a single stereoisomer or any mixture of stereoisomers. This crystalline acid is useful in treating disease-states characterized by inflammation, such as inflammatory and autoimmune disorders or pulmonary or respiratory tract inflammations in humans. Methods of preparing the crystalline acid are also described.
    Type: Application
    Filed: December 3, 2007
    Publication date: July 31, 2008
    Applicant: Bayer Schering Pharma Aktiengesellschaft
    Inventors: Klaus Bartel, Danja Grossbach, William J. Guilford, Michael Sander, Gabriele Winter
  • Patent number: 7126018
    Abstract: The present invention is directed to a process of producing polyol esters possessing desirable composition and color. Preferably, such a process does not require molecular distillations or decoloration steps to yield a light-colored polyol ester composition. Materials that are dark in color are often produced during the esterification of polyols with vegetable oil fatty acids. It has been discovered that the present process yields the desired ester products that are light in color. The present process comprises an esterification of a polyol, such as propylene glycol, and a fatty acid ester, such as a vegetable oil fatty acid methyl ester, in the presence of a catalyst and borohydride, wherein a polyol ester having a Lovibond color below about 0.6 Red and below about 1.5 Yellow is produced.
    Type: Grant
    Filed: January 16, 2004
    Date of Patent: October 24, 2006
    Assignee: Archer-Daniels-Midland Company
    Inventor: George B. Poppe
  • Patent number: 7119216
    Abstract: An olefin metathesis process involving contacting an unsaturated fatty acid ester or unsaturated fatty acid, such as methyloleate or oleic acid, with a lower olefin, preferably ethylene, in the presence of a metathesis catalyst so as to prepare a first product olefin, preferably, a reduced chain ?-olefin, such as methyl-9-decenoate or 9-decenoic acid, respectively. The metathesis catalyst contains ruthenium or osmium and a chelating ligand, preferably, a chelating ligand containing a carbene moiety and a second donor moiety of a Group 15 or 16 element Optionally, the catalyst can be supported on a catalyst support, such as, a cross-linked polymeric resin.
    Type: Grant
    Filed: February 27, 2002
    Date of Patent: October 10, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Thomas H. Newman, Cynthia L. Rand, Kenneth A. Burdett, Bob R. Maughon, Donald L. Morrison, Eric P. Wasserman
  • Patent number: 7053127
    Abstract: A quaternary surfactant comprising a cyclic diamine group, compositions comprising the quaternized amido cyclic amine surfactant, a gelled aqueous composition comprising the quaternized amido cyclic amine surfactant, use of the gelled aqueous well treatment applications and methods of preparation and intermediates used to prepare the quaternized amido cyclic amine surfactant.
    Type: Grant
    Filed: September 16, 2002
    Date of Patent: May 30, 2006
    Assignee: Nalco Company
    Inventors: Duane S Treybig, Kin-Tai Chang
  • Patent number: 6841691
    Abstract: 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: Grant
    Filed: May 21, 2001
    Date of Patent: January 11, 2005
    Assignee: DSM N.V.
    Inventors: Gerardus Karel Maria Verzijl, Johannes Gerardus Vries De, Quirinus Bernardus Broxterman