Molecular Rearrangement Of The Acid Moieties Of Glyceride Esters (e.g., Random Or Directed Low Temperature Intra- Or Inter-esterification Of Fats, Oils, Etc.) Patents (Class 554/169)
  • Patent number: 7754905
    Abstract: A method comprising applying a controlled flow cavitation apparatus to a biodiesel production process in order to increase fatty acid alkyl ester yield. A feedstock comprising free fatty acids can be passed through a controlled flow cavitation apparatus at a velocity capable of generating a hydrodynamic cavitation zone where the free fatty acids can be esterified. One or more controlled flow cavitation apparatuses can be applied at various points of a biodiesel production process.
    Type: Grant
    Filed: July 3, 2008
    Date of Patent: July 13, 2010
    Assignee: Arisdyne Systems, Inc.
    Inventor: Oleg V. Kozyuk
  • Patent number: 7722755
    Abstract: Methods, systems, and devices are provided for synthesizing one or more chemical products from a renewable oil, comprising the step of flowing a fluid which comprises a renewable oil through a high voltage electrical field effective to catalyze a chemical reaction involving the renewable oil. Examples of renewable oils include vegetable oils, animal fats, bio-oils, and combinations thereof. In one embodiment, the fluid further comprises an alcohol mixed with the oil, and the chemical reaction produces biodiesel and an etherified glycerin. In one embodiment, the biodiesel is further reacted to produce acetic acid.
    Type: Grant
    Filed: November 12, 2004
    Date of Patent: May 25, 2010
    Assignee: ECR Technologies, Inc.
    Inventors: J. Alan Lawson, Ahmed A. Baosman
  • Patent number: 7691270
    Abstract: A method of removing at least one polar component from a fluid stream. The method comprises providing a fluid stream comprising at least one nonpolar component and at least one polar component. The fluid stream is contacted with a supercritical solvent to remove the at least one polar component. The at least one nonpolar component may be a fat or oil and the at least one polar component may be water, dirt, detergents, or mixtures thereof. The supercritical solvent may decrease solubility of the at least one polar component in the fluid stream. The supercritical solvent may function as a solvent or as a gas antisolvent. The supercritical solvent may dissolve the nonpolar components of the fluid stream, such as fats or oils, while the polar components may be substantially insoluble. Alternatively, the supercritical solvent may be used to increase the nonpolarity of the fluid stream.
    Type: Grant
    Filed: July 13, 2005
    Date of Patent: April 6, 2010
    Assignee: Battelle Energy Alliance, LLC
    Inventors: Daniel M. Ginosar, Robert V. Fox
  • Publication number: 20100063309
    Abstract: Glyceride-containing feed for a base catalyzed transesterification with lower alkanol to make biodiesel is pretreated with glycerin separated during the transesterification to partially convert glycerides with lower alkanol contained in the separated glycerin using base catalyst in the separated glycerin while reducing the free fatty acid and phosphorus compound concentrations in the glyceride-containing feed. Unique producer compositions are provided by the pretreatment processes.
    Type: Application
    Filed: September 19, 2007
    Publication date: March 11, 2010
    Applicant: Best Energies, Inc.
    Inventors: Donald Leroy Bunning, Louis A. Kapicak, Thomas Arthur Maliszewski, David James Schreck
  • Patent number: 7667060
    Abstract: This invention involves a kind of fatty acid methyl ester (bio-diesel fuel), especially the method of obtaining ester-like substances by means of chemical alterations of oil.
    Type: Grant
    Filed: April 25, 2008
    Date of Patent: February 23, 2010
    Assignee: Sichuan Gushan Oil Chemical Co. Ltd.
    Inventors: Jianqiu Yu, Deyu Chen, Junxiong Li, Zihong Chen, Gonghao Chen
  • Patent number: 7667059
    Abstract: The invention relates to a process for producing a fatty alcohol and glycerin by hydrogenation reaction of fats and oils in the presence of a catalyst, wherein the reaction is carried out in the coexistence of an organic solvent.
    Type: Grant
    Filed: March 6, 2006
    Date of Patent: February 23, 2010
    Assignee: Kao Corporation
    Inventors: Toru Sakamoto, Nobuhiro Tatsumi, Hideaki Ueoka
  • Patent number: 7652156
    Abstract: A method allowing, from natural fat or oils, vegetable or animal, or from other glyceride mixtures, to obtain in a quasi-quantitative way fatty acid ethyl esters that can be used as gas oil substitutes, comprises the succession of stages as follows: a stage (a) wherein the oil, the fat or the glyceride mixture is transesterified by ethanol using a soluble catalyst or a catalyst that becomes soluble during the reaction, a stage (b) wherein the glycerin formed is decanted and removed, without requiring an excess ethanol evaporation operation, a stage (c) wherein a second transesterification reaction is carried out so as to obtain a product whose ester content is at least 97% by mass, a stage (d) wherein controlled neutralization of the catalyst is carried out, a stage (e) wherein the excess ethanol is removed by distillation, a stage (f) wherein the ester undergoes purification by means of water wash sequences, and a stage (g) wherein the ester mixture is dried under reduced pressure.
    Type: Grant
    Filed: September 20, 2006
    Date of Patent: January 26, 2010
    Assignee: Institut Francais du Petrole
    Inventors: Gérard Hillion, Bruno Delfort
  • Publication number: 20100010246
    Abstract: A method of forming a biodiesel product and a heterogeneous catalyst system used to form said product that has a high tolerance for the presence of water and free fatty acids (FFA) in the oil feedstock is disclosed. This catalyst system may simultaneously catalyze both the esterification of FAA and the transesterification of triglycerides present in the oil feedstock. The catalyst system according to one aspect of the present disclosure represents a class of zinc and lanthanum oxide heterogeneous catalysts that include different ratios of zinc oxide to lanthanum oxides (Zn:La ratio) ranging from about 10:0 to 0:10. The Zn:La ratio in the catalyst is believed to have an effect on the number and reactivity of Lewis acid and base sites, as well as the transesterification of glycerides, the esterification of fatty acids, and the hydrolysis of glycerides and biodiesel.
    Type: Application
    Filed: May 19, 2009
    Publication date: January 14, 2010
    Inventors: Shuli Yan, Steven O. Salley, K.Y. Simon Ng
  • Patent number: 7622600
    Abstract: A continuous biofuel production process includes the steps of introducing a feedstock containing fatty acids and triglycerides into a first reaction vessel, in which alkyl esters are produced through esterification of free fatty acids. The alkyl esters and triglycerides are introduced into a second reaction vessel, in which at least a portion of the triglycerides are converted to alkyl esters and glycerin through transesterification. The alkyl esters, glycerin, and remaining triglycerides are introduced into a third reaction vessel, in which at least a portion of the remaining triglycerides are converted to alkyl esters and glycerin through transesterification.
    Type: Grant
    Filed: January 5, 2007
    Date of Patent: November 24, 2009
    Assignee: Redland Industries, Inc.
    Inventor: Wesley Drew Marr
  • Patent number: 7605281
    Abstract: The method of producing fatty acid alkyl esters and/or glycerine of the present invention is a method of producing high-purity fatty acid alkyl esters and/or glycerine advantageously from the energy viewpoint while reducing the energy consumption of the production, and the products can be used in various fields of application, for example in biodiesel fuels, foods, cosmetics and pharmaceuticals.
    Type: Grant
    Filed: August 30, 2004
    Date of Patent: October 20, 2009
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Tomoharu Oku, Masanori Nonoguchi, Toshimitsu Moriguchi
  • Patent number: 7592470
    Abstract: A novel process is described for producing esters of linear monocarboxylic acids containing 6 to 26 carbon atoms, by reacting vegetable or animal oils, neutral or otherwise, with monoalcohols containing 1 to 18 carbon atoms in the presence of a catalyst selected from: mixtures of titanium oxide and alumina having formula: (TiOx)y(Al2O3)1-y where x has the value 1.5 to 2.2 and y, representing the weight ratio of the two oxides, has a value of 0.005 to 0.995; mixtures of zirconium oxide and alumina having formula: (ZrOx)y(Al2O3)1-y where x has the value 1.5 to 2.2 and y has a value of 0.005 to 0.995; and mixtures of antimony oxide and alumina having formula: (SbOx)y(Al2O3)1-y where x has the value 1.2 to 2.6 and y has a value of 0.005 to 0.995, in order to directly produce, in one or more steps, an ester for use as a fuel and a pure glycerin.
    Type: Grant
    Filed: May 26, 2004
    Date of Patent: September 22, 2009
    Assignee: Institut Francais du Petrole
    Inventors: Thierry Lacome, Gerard Hillion, Bruno Delfort, Renaud Revel, Serge Leporq, Gustave Acakpo
  • Patent number: 7582784
    Abstract: A method for transesterification of triglycerides, especially those containing free fatty acids, with methanol. The method uses a catalyst derived from an acidic ion exchange resin. The catalyst is contacted with a reaction mixture containing a triglyceride and methanol under conditions suitable for transesterification.
    Type: Grant
    Filed: July 12, 2007
    Date of Patent: September 1, 2009
    Assignee: Rohm and Haas Company
    Inventors: Rajiv Manohar Banavali, Abraham Benderly
  • Patent number: 7563915
    Abstract: Methods for improved manufacture of green biodiesel focus on the selection and use of one or more solid metallic oxide base catalyst(s) selected from the group consisting of calcium oxide (CaO), calcium aluminum oxide (CaO—Al2O3), calcium titanate (CaTiO3), barium titanate (BaTiO3), magnesium aluminum oxide (MgO—Al2O3), zinc oxide (ZnO), copper (II) oxide (CuO), nickel oxide (NiO), manganese oxide (MnO), titanium oxide (TiO), vanadium oxide (VO), cobalt oxide (CoO), iron oxide (FeO), chromite (FeCr2O4), hydrotalcite (Mg6Al2(CO3)(OH)16.4(H2O), magnetite (Fe3O4), magnesium silicate and calcium silicate.
    Type: Grant
    Filed: May 29, 2007
    Date of Patent: July 21, 2009
    Assignee: The Penn State Research Foundation
    Inventors: Jack Vincent Matson, Dheeban Chakravarthi Kannan
  • 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
  • Patent number: 7550278
    Abstract: The present invention provides a new process for producing biodiesel from renewable oil under lipase catalysis in an organic medium reaction system. In this process, a short chain alcohol ROH is used as an acyl acceptor, a relatively hydrophilic organic solvent having no negative effect on the reactivity of lipase is used as the reaction medium, and a renewable oil raw material is catalyzed by a lipase to synthesize biodiesel through a transesterification reaction. In the process of the present invention, the renewable oil raw material can be almost completely converted into biodiesel and a byproduct glycerin, and the yield of the biodiesel is 94% or more. This new type organic medium reaction system promotes the solubility of the short chain alcohol in the renewable oil raw material, and dissolves part of the byproduct glycerin.
    Type: Grant
    Filed: November 29, 2004
    Date of Patent: June 23, 2009
    Assignee: Tsinghua University
    Inventors: Wei Du, Dehua Liu, Lilin Li
  • Patent number: 7550614
    Abstract: A method for esterification of free fatty acids in triglycerides, with C1-C8 aliphatic alcohols. The method uses an acidic ion exchange resin as a catalyst. The catalyst is contacted with a reaction mixture containing a triglyceride having at least 1% free fatty acids and a C1-C8 aliphatic alcohol under conditions suitable for esterification.
    Type: Grant
    Filed: October 19, 2007
    Date of Patent: June 23, 2009
    Assignee: Rohm and Haas Company
    Inventors: Rajiv Manohar Banavali, Gregory C. Pierce
  • Patent number: 7514575
    Abstract: A method of producing an alkyl ester. The method comprises providing an alcohol and a triglyceride or fatty acid. An expanding gas is dissolved into the alcohol to form a gas expanded solvent. The alcohol is reacted with the triglyceride or fatty acid in a single phase to produce the alkyl ester. The expanding gas may be a nonpolar expanding gas, such as carbon dioxide, methane, ethane, propane, butane, pentane, ethylene, propylene, butylene, pentene, isomers thereof, and mixtures thereof, which is dissolved into the alcohol. The gas expanded solvent may be maintained at a temperature below, at, or above a critical temperature of the expanding gas and at a pressure below, at, or above a critical pressure of the expanding gas.
    Type: Grant
    Filed: May 6, 2005
    Date of Patent: April 7, 2009
    Assignee: Battelle Energy Allicance, LLC
    Inventors: Daniel M. Ginosar, Robert V. Fox, Lucia M. Petkovic
  • Patent number: 7507846
    Abstract: Method and apparatus for producing biodiesel fuel, i.e., alkyl ester, from vegetable and/or animal oil. A transesterification catalyst is prepared in a base catalyst tank by spraying alkyl alcohol under pressure through jets at metal hydroxide pellets until the pellets have fully reacted with the alcohol. The oil is heated and transesterified in the presence of alkyl alcohol and the transesterification catalyst in a closed, recirculating transesterification flow system under slight cavitation to yield product alkyl ester and product glycerol. Cavitation is achieved by permitting air to enter the transesterification flow system through an adjustable air inlet valve. When permitted to stand, product alkyl ester forms an upper layer that is decanted and subjected to purification steps, to remove particulates and alkyl alcohol from the product alkyl ester, and a lower layer of product glycerol is drained away.
    Type: Grant
    Filed: March 17, 2004
    Date of Patent: March 24, 2009
    Inventor: Michael F. Pelly
  • Publication number: 20090062559
    Abstract: Alkyl esters boiling largely within the specification range for jet fuel may be made from triglycerides without a water-washing step, by centrifugation in a timely manner and at a sufficiently high time/G-force/distance product so as to bring about separation of a transitory second phase containing the residual catalyst. The esters or fractions thereof may be combined with jet or diesel fuels to lower the freezing and cloud points respectively.
    Type: Application
    Filed: August 28, 2008
    Publication date: March 5, 2009
    Applicant: SAUBER TECHNOLOGIES, LLC
    Inventors: Michael Philip Doyle, Steve Smith
  • Patent number: 7488837
    Abstract: The present invention relates to a process for preparing an alkyl ester of a fatty acid, including the steps of carrying out an esterification reaction between a free fatty acid contained in a fat or oil and an alcohol; carrying out a transesterification reaction between a fat or oil and an alcohol; and refining an alkyl ester of a fatty acid, wherein at least any one of three steps is carried out in a corresponding step selected from the steps of (a) contacting a fat or oil and an alcohol with a resin foamed article to which a catalyst containing fine strongly acidic particles is supported or a resin foamed article modified to be strongly acidic, and carrying out an esterification reaction between a free fatty acid in the fat or oil and the alcohol; (b) contacting a fat or oil and an alcohol with a resin foamed article to which a catalyst containing fine alkali particles is supported, and carrying out a transesterification reaction between the fat or oil and the alcohol; and (c) contacting a reaction mixture
    Type: Grant
    Filed: June 28, 2005
    Date of Patent: February 10, 2009
    Assignee: Revo International Inc.
    Inventors: Keiichi Tsuto, Tetsuya Koshikawa
  • Patent number: 7473791
    Abstract: This invention provides a process for synthesizing biodiesel from renewable oils, comprising: carrying out a transesterification reaction, in the presence of an enzyme catalyst, between a low carbon fatty acid ester RCOOR? as an acyl acceptor and a renewable oil, wherein the molar ratio of the low carbon fatty acid ester to the renewable oil is in the range of from 3:1 to 20:1, the transesterification reaction producing a glycerine tri-(low carbon) carboxylic ester by-product, and reacting the glycerine tri-(low carbon) carboxylic ester by-product with a low carbon alcohol R?OH to obtain the low carbon fatty acid ester, wherein the low carbon fatty acid ester is capable of being recycled in a further round of biodiesel synthesis, wherein R and R? are independently selected from the group consisting of alkyls with one to four carbon atoms.
    Type: Grant
    Filed: January 15, 2004
    Date of Patent: January 6, 2009
    Assignee: Tsinghua University
    Inventors: Wei Du, Yuanyuan Xu, Dehua Liu
  • Patent number: 7468450
    Abstract: The invention relates to a process for the preparation of fatty acid esters from fats and oils of biological origin by transesterification with monohydric alcohols in the presence of basic catalysts, the catalysts being salts of a basic organic compound and carbonic acid.
    Type: Grant
    Filed: March 22, 2005
    Date of Patent: December 23, 2008
    Inventors: Siegfried Peter, Eckhard Weidner
  • Publication number: 20080293956
    Abstract: This invention involves a kind of fatty acid methyl ester (bio-diesel fuel), especially the method of obtaining ester-like substances by means of chemical alterations of oil.
    Type: Application
    Filed: April 25, 2008
    Publication date: November 27, 2008
    Applicant: Sichuan Gushan Oil Chemical Co. Ltd.
    Inventors: Jianqiu Yu, Deyu Chen, Junxiong Li, Zihong Chen, Gonghao Chen
  • Patent number: 7452448
    Abstract: A method for producing a fat by distillation and purification while preventing isomerization. The distillation and purification is conducted under an acidic condition to prevent isomerization.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: November 18, 2008
    Assignee: Fuji Oil Company, Limited
    Inventors: Tadayuki Okada, Kotaro Yamaguchi
  • Patent number: 7420073
    Abstract: A process that employs a heterogeneous catalyst comprising a zinc aluminate mixed oxide and having the following formula: ZnAl2O4, xZnO, yAl2O3 in which x and y each represent a number in the range 0 to 2, and in which the zinc aluminate is more particularly of the spinel type, makes it possible, by means of C1 to C5 monoalcohols, to: transesterify vegetable or animal oils having a natural free acidity, such as unrefined degummed rapeseed, soya, sunflower oils or exotic oils of the African oil, palm nut oil or coconut oil type, which are naturally rich in fatty acids; and simultaneously esterify their free acidity; so as to use phospholipid free and/or degummed unrefined acid oil with an acid number in the range 0.5 to 20, for example 1 to 15 and preferably 2 to 12, to produce esters, for example methyl esters, for use as fuels.
    Type: Grant
    Filed: March 17, 2004
    Date of Patent: September 2, 2008
    Assignee: Institut Francais du Petrole
    Inventors: Gérard Hillion, Dominique Le Pennec
  • 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: 20080167485
    Abstract: A method for heterogeneous catalysis of organic reactions having at least one reactant and a product; said method comprising steps of: (a) providing a catalyst comprising a gel-type acidic ion exchange resin; and (b) contacting said catalyst with said at least one reactant; wherein said organic reaction is selected from among esterification, alkene addition or isomerization, Friedel-Crafts acylation, alcohol or alkene carbonylation, nitration, and Ritter reaction.
    Type: Application
    Filed: January 7, 2008
    Publication date: July 10, 2008
    Inventor: Rajiv Manohar Banavali
  • Publication number: 20080161588
    Abstract: Hydrogenated vegetable oil exhibiting superior thermal stability and containing reduced levels of saturates and trans fatty acids are produced using an activated hydrogenation catalyst and/or an improved hydrogenation process incorporating high shear. The use of a high shear mechanical device incorporated into the hydrogenation process as a reactor device is shown to be capable of enabling reactions that would normally not be feasible under a given set of reaction pressure and temperature conditions. For example, the hydrogenation process described herein enables a reduction of hydrogenation time, and operation at lower temperatures than current processes. The resulting hydrogenated vegetable oil is particularly useful in frying, confectionery baking, and other applications where a product with a low trans fat content or higher thermal stability is desirable. The hydrogenated oil produced may comprise less than 10 weight % of trans fatty acids with less than 5 weight % of linolenic acid (C18:3).
    Type: Application
    Filed: December 20, 2007
    Publication date: July 3, 2008
    Applicant: HRD CORP. D/B/A MARCUS OIL & CHEMICAL
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Patent number: 7367995
    Abstract: Fuel oxygenates comprised of fatty acid or fatty acid ester derivatives which have been reacted with ozone; a base; and a lower alkanol (1 to 8 carbon atoms) are described. The oxygenates comprise ester groups at a point of cleavage by the ozone which provide oxygen in the oxygenate.
    Type: Grant
    Filed: February 27, 2006
    Date of Patent: May 6, 2008
    Assignee: Board of Trustees of Michigan State University
    Inventors: Ramani Narayan, Daniel Graiver, Kenneth W. Farminer
  • Patent number: 7271275
    Abstract: The present invention relates to a process for producing a fatty acid ester by using a fatty acid and an alcohol as starting materials, including reducing the acid value of a raw material supplied to a catalyst layer to an acid value lower than the acid value of a raw material fatty acid and then esterifying the raw material in the presence of a solid catalyst.
    Type: Grant
    Filed: October 13, 2004
    Date of Patent: September 18, 2007
    Assignee: Kao Corporation
    Inventors: Takanobu Katayama, Nobuhiro Tatsumi, Osamu Tabata
  • 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: 7227030
    Abstract: An object of the present invention is to solve a problem of separation and recovery of catalysts present in an alkali metal catalytic method currently often used, a problem of excess consumption of a catalyst by a free fatty acid in a raw material, and other problems, and to solve a problem of the presence of a large excess amount of alcohol in a conventional supercritical methanol method, and to provide a method for producing a fatty acid alkyl ester composition in a reaction system containing water and free fatty acid present. The present invention has attained the above-mentioned object by provided a method for producing a fatty acid alkyl ester composition using fats and oils containing a fatty acid glyceride and/or fatty acid, wherein alcohol and/or water is allowed to co-exist with the above-mentioned fats and oils and the reaction is conducted under conditions of a temperature of 100° C. to 370° C. and a pressure of 1 to 100 MPa.
    Type: Grant
    Filed: June 12, 2003
    Date of Patent: June 5, 2007
    Inventor: Shiro Saka
  • Patent number: 7145026
    Abstract: A process for converting at least one triglyceride feedstock to at least one fatty-acid methyl ester product is disclosed. The process includes a continuous, plug-flow environment with a single-pass residence time as low as about 10 seconds, and a conversion of at least 70 percent.
    Type: Grant
    Filed: April 11, 2003
    Date of Patent: December 5, 2006
    Assignee: Biodiesel Technologies, Inc.
    Inventor: Christian A. Fleisher
  • Patent number: 7128766
    Abstract: Wax compositions that have a high triacylglycerol content are provided. The wax compositions can be used to produce candle and are particularly useful in the production of container candles. The wax compositions commonly have a melting point of about 50° C. to 57° C. and include a triacylglycerol component which has a fatty acid composition including about 14 to 25 wt. % 16:0 fatty acid; about 20 to 30 wt. % 18:0 fatty acid; and about 45 to 60 wt. % 18:1 fatty acid. Methods of producing candles from a triacylglycerol-based wax and kits, which include the triacylglycerol-based wax, are also provided.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: October 31, 2006
    Assignee: Cargill, Incorporated
    Inventors: Timothy A. Murphy, Robert E. Wainwright
  • Patent number: 7122688
    Abstract: The present invention provides a method to prepare a fatty acid lower alkyl esters from a feedstock, such as a vegetable or an animal oil, comprising one or more fatty acid glycerol esters such as mono-, di- or tri-glycerides, and free fatty acids, comprising combining the feedstock, a lower alcohol and an acidic mesoporous silicate under conditions wherein the mesoporous silicate catalyzes the formation of the corresponding fatty acid lower alkyl ester of the free fatty acids an optionally glycerol.
    Type: Grant
    Filed: September 20, 2004
    Date of Patent: October 17, 2006
    Assignee: Iowa State University Research Foundation
    Inventors: Victor Shang-Yi Lin, Daniela Rodica Radu
  • Patent number: 7115760
    Abstract: The present invention relates to a process for controlling the fatty acid chain composition of triglycerides wherein a feed stream comprises a mixture of triglycerides containing at least one long chain. Said mixture is substantially free of trishort chain triglycerides and it is treated in at least two fractionation steps to fractionate between long chain triglycerides at temperatures above 200° C. and pressures between 0.01 and 10 Pa, wherein one of said steps fractionates between trilong chain triglycerides and mono- and dilong chain triglycerides and the other one of said steps fractionates between monolong chain triglycerides and dilong chain triglycerides. The process can be used for the providing of target triglycerides having a controlled fatty acid chain distribution.
    Type: Grant
    Filed: October 31, 2003
    Date of Patent: October 3, 2006
    Assignee: Danisco A/S
    Inventors: Flemming Vang Sparsø, Ulrik Engelrud
  • Patent number: 7109363
    Abstract: A method for the production of fatty acid esters of primary and/or secondary alcohols from raw, unpurified oils or fats containing free fatty acids and slimy substances or from waste oils loaded with free fatty acids from the food industry. Acidic catalytic esterification is performed on the free fatty acids along with extensive deactivation of the slimy substances present with respect to the disadvantageous emulsion-forming property thereof, whereby a water-free primary and/or secondary alcohol and a highly acidic hygroscopic catalyst are added to the starting substance in the form of crude oil or fat or waste oil, the reaction product is rinsed with glycol from a prior alkaline transesterification, whereupon alkaline transesterification occurs for the unmodified remaining glyceridically bound fatty acids in the reaction product of the acidic-catalytic esterification process.
    Type: Grant
    Filed: November 29, 2001
    Date of Patent: September 19, 2006
    Assignee: Westfalia Separator AG
    Inventors: Karlheinz Brunner, Rainer Frische, Rainer Ricker
  • Patent number: 7091367
    Abstract: The method for the esterification of a fatty acid F is carried out in a column with a packing. In addition to functioning as a catalytic reactor, the packing functions as a stripping section. A heteregenous catalysis of a fatty acid is carried out with an alcohol used in the same molar ratio or in excess. A gaseous alcohol-rich counter-flow is produced in a sump of the column by vaporization. Water is removed from the reaction zone by means of the counter-flow acting as a stripping gas. The loaded stripping gas is at least partially liquefied at the head of the column. The head product is separated into a water-rich fraction as well as an alcohol-rich fraction. The alcohol-rich fraction is returned to the process as a starting material for the esterification and for the production of the stripping gas.
    Type: Grant
    Filed: November 12, 2003
    Date of Patent: August 15, 2006
    Assignee: Sulzer Chemtech
    Inventors: Peter Moritz, Peter Faessler, Claudia von Scala, Oliver Bailer
  • Patent number: 7081542
    Abstract: A method for producing 1,3-diglyceride oils from triglyceride containing oils is disclosed. The method uses alkali metal salts or alkali earth metal salts of mono-carboxylic or di-carboxylic acids to drive glycerolysis under conditions such that commercial, food-quality 1,3-diglyceride oils are produced.
    Type: Grant
    Filed: October 3, 2002
    Date of Patent: July 25, 2006
    Assignee: Archer-Daniels-Midland Company
    Inventors: Lewis Jacobs, Immok Lee, George Poppe
  • Patent number: 7074948
    Abstract: The present invention relates to the cosmetic use of certain esters, prepared by the reaction of a Guerbet alcohol and lanolin. The result is a cosmetically elegant ester and lanolin alcohol which is a highly functional material in skin care. These compositions provide conditioning effects when applied to the hair and skin.
    Type: Grant
    Filed: December 3, 2004
    Date of Patent: July 11, 2006
    Assignee: Zenitech LLC
    Inventor: Kenneth Klein
  • Patent number: 7067684
    Abstract: Processes for preparing conjugated linoleic acid triglycerides are described which comprise: (a) providing a conjugated linoleic acid alkyl ester, wherein the alkyl group is linear or branched and has from 1 to 5 carbon atoms; and (b) subjecting conjugated linoleic acid alkyl ester to transesterification with triacetin to provide a conjugated linoleic acid triglyceride.
    Type: Grant
    Filed: December 16, 2004
    Date of Patent: June 27, 2006
    Assignee: Cognis Deutschland GmbH & Co. KG
    Inventors: Alfred Westfechtel, Stefan Busch, Elke Grundt, Peter Horlacher
  • Patent number: 7002030
    Abstract: The invention relates to a substance which lowers LDL cholesterol levels in serum and which is fat soluble ?-sitostanol fatty acid ester, and to a method for preparing and using the same. The substance can be taken orally as a food additive, food substitute or supplement. A daily consumption of the ?-sitostanol ester in an amount between about 0.2 and about 20 g/day has been shown to reduce the absorption of biliary and endogenic cholesterol.
    Type: Grant
    Filed: October 6, 2003
    Date of Patent: February 21, 2006
    Assignee: Raisio Benecol Ltd.
    Inventors: Tatu Miettenen, Ingmar Wester, Hannu Vanhanen
  • Patent number: 6969771
    Abstract: A process for producing a processed glyceride having a satisfactory color tone and having high purity without the need of a fractionation step, by mitigating the deterioration in a color tone caused by the processing and recycling of a fatty acid ester recovered after an interesterification reaction. The process comprises subjecting a glyceride fat and a fatty acid ester and/or a free fatty acid to interesterification, distilling the reaction product to recover a part or all of fatty acid esters and/or free fatty acids therein, subjecting the distillation fraction recovered to hydrogenation, and to re-distillation or mixing with the fresh fatty acid ester and/or fresh free fatty acid in any order, re-reacting the resultant fraction or mixture with the distillation residue, and separating a fat fraction from the final reaction product, and is characterized in that the content of components other than the fatty acid ester and/or free fatty acid is controlled to 3.0 wt. % or lower.
    Type: Grant
    Filed: June 21, 2002
    Date of Patent: November 29, 2005
    Assignee: Fuji Oil Company, Limited
    Inventors: Tadayuki Okada, Kotaro Yamaguchi
  • Patent number: 6965044
    Abstract: A method for converting free fatty acids in acid oil or acid fat into fatty acid methyl esters is disclosed. The method involves adding a small amount of methanol and an acid catalyst to the acid oil or acid fat and subjecting the mixture to conditions that allow the fatty acid methyl esters to form. A lipid phase containing the fatty acid methyl esters and triglycerides can from and be separated from the rest of the reaction mixture. The lipid phase can then be subjected to conditions suitable for converting the triglycerides into fatty acid methyl esters. The method of present invention is especially useful for a process of generating biodiesel using a starting material of vegetable and animal oils and fats that contain a relatively high level of free fatty acids.
    Type: Grant
    Filed: July 5, 2002
    Date of Patent: November 15, 2005
    Assignee: Iowa State University Research Foundation
    Inventors: Earl G. Hammond, Tong Wang
  • Patent number: 6960672
    Abstract: The present invention relates to a process for preparing an alkyl ester of a fatty acid wherein a transesterification reaction is carried out between a fat or oil and an alcohol in the presence of a catalyst comprising a composite metal oxide having a perovskite structure; and a process for preparing an alkyl ester of a fatty acid wherein a transesterification reaction is carried out between a fat or oil and an alcohol in the presence of a catalyst comprising at least one member selected from the group consisting of oxides, hydroxides and carbonates of alkaline earth metals is used as the catalyst, with the alcohol made into a supercritical state or subcritical state. According to the present invention, the alkyl ester of a fatty acid which can be effectively utilized as a diesel fuel oil or the like can be prepared at high efficiency and on an industrial scale mainly from triglyceride contained in a fat or oil, especially a waste oil.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: November 1, 2005
    Assignee: Revo International Inc.
    Inventors: Masahide Nakayama, Keiichi Tsuto, Takenori Hirano, Tsutomu Sakai, Ayato Kawashima, Hirohisa Kitagawa
  • Patent number: 6943262
    Abstract: Oils containing a triacylglycerol polyol ester and a non-glycerol polyol ester are described, as well as methods of making such oils. Methods for improving lubrication properties of a vegetable oil also are described.
    Type: Grant
    Filed: September 24, 2002
    Date of Patent: September 13, 2005
    Assignee: Cargill, Incorporated
    Inventors: Dharma R. Kodali, Scott C Nivens
  • Patent number: 6933398
    Abstract: The present invention relates to a process for obtaining fatty acid esters from triglycerides by means of alcoholysis. In particular, the invention relates to a process for the transesterification of fat and/or oil by alcoholysis wherein, in order to accelerate the process in the initial stage, at least one alkanol fatty acid ester is added in a quantity such that the reaction mixture produced thereby consists of one phase. A high reaction rate can thereby be maintained in the process from the beginning.
    Type: Grant
    Filed: September 24, 2003
    Date of Patent: August 23, 2005
    Inventors: Siegfried Peter, Eckhard Weidner
  • Patent number: 6905850
    Abstract: The invention provides a process for producing 2-monoglycerides (2-MG) or triglycerides (TG), particularly triglycerides having polyunsaturated fatty acid (PUFA) residues in the sn-2 positions, at an extremely high purity and a high efficiency. The 2-MG is produced by conducting alcoholysis of a starting TG with a first 1,3-lipase. Then, the TG is produced by introducing fatty acid residues to the 1- and 3-positions of the produced 2-MG by using a second 1,3-lipase. The fatty acid residue in the 2-posiiton is preferably a residue of DHA, EPA or ARA. The “first lipase” refers to one which is selective for the 1- and 3-positions and can act even on a long-chain fatty acid in alcoholysis, while the “second lipase” refers to one which is selective for the 1- and 3-positions and can produce a TG through the reaction of a 2-MG with a fatty acid ester or a free fatty acid.
    Type: Grant
    Filed: July 2, 2001
    Date of Patent: June 14, 2005
    Assignee: Nippon Suisan Kaisha, Ltd.
    Inventors: Roxana Irimescu, Kiyomi Furihata, Kazuhiko Hata, Tsuneo Yamane
  • Patent number: 6884900
    Abstract: There is provided a method for producing fatty acid alcohol ester useful as a substitute fuel for light oil in which an ester interchange reaction between fats or oils and alcohol is carried out in a reactor 1 by applying ultrasonic irradiation at a frequency of 15 to 100 kHz and irradiation intensity of 0.5 to 20 W/cm2 in the presence of a catalyst, followed by an application of ultrasonic irradiation at a frequency of 200 to 3,000 kHz and irradiation intensity of 0.5 to 20 W/cm2 to the reaction product in a separation tank 4 to separate fatty acid alcohol ester and glycerol. Such ultrasonic irradiation in the separation tank 4 may be applied to an interface between fatty acid alcohol ester and glycerol.
    Type: Grant
    Filed: October 6, 2003
    Date of Patent: April 26, 2005
    Assignee: Cosmo Engineering Co., Ltd.
    Inventors: Yasuaki Maeda, Mircea Vinatoru, Carmen Eugenia Stavarach, Kunio Iwai, Hideki Oshige
  • Patent number: 6878837
    Abstract: Alkyl esters of fatty acids, and high purity glycerin, are produced using a process comprising a set of transesterification reactions between a vegetable or animal oil and an aliphatic monoalcohol employing a heterogeneous catalyst, for example based on zinc aluminate, the water content in the reaction medium being controlled to a value that is below a given limiting value.
    Type: Grant
    Filed: April 11, 2003
    Date of Patent: April 12, 2005
    Assignee: Institut Francais du Petrole
    Inventors: Laurent Bournay, Gerard Hillion, Pierre Boucot, Jean-Alain Chodorge, Charles Bronner, Alain Forestiere