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: 7754905Abstract: 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: GrantFiled: July 3, 2008Date of Patent: July 13, 2010Assignee: Arisdyne Systems, Inc.Inventor: Oleg V. Kozyuk
-
Patent number: 7722755Abstract: 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: GrantFiled: November 12, 2004Date of Patent: May 25, 2010Assignee: ECR Technologies, Inc.Inventors: J. Alan Lawson, Ahmed A. Baosman
-
Patent number: 7691270Abstract: 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: GrantFiled: July 13, 2005Date of Patent: April 6, 2010Assignee: Battelle Energy Alliance, LLCInventors: Daniel M. Ginosar, Robert V. Fox
-
Publication number: 20100063309Abstract: 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: ApplicationFiled: September 19, 2007Publication date: March 11, 2010Applicant: Best Energies, Inc.Inventors: Donald Leroy Bunning, Louis A. Kapicak, Thomas Arthur Maliszewski, David James Schreck
-
Patent number: 7667060Abstract: 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: GrantFiled: April 25, 2008Date of Patent: February 23, 2010Assignee: Sichuan Gushan Oil Chemical Co. Ltd.Inventors: Jianqiu Yu, Deyu Chen, Junxiong Li, Zihong Chen, Gonghao Chen
-
Patent number: 7667059Abstract: 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: GrantFiled: March 6, 2006Date of Patent: February 23, 2010Assignee: Kao CorporationInventors: Toru Sakamoto, Nobuhiro Tatsumi, Hideaki Ueoka
-
Patent number: 7652156Abstract: 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: GrantFiled: September 20, 2006Date of Patent: January 26, 2010Assignee: Institut Francais du PetroleInventors: Gérard Hillion, Bruno Delfort
-
Publication number: 20100010246Abstract: 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: ApplicationFiled: May 19, 2009Publication date: January 14, 2010Inventors: Shuli Yan, Steven O. Salley, K.Y. Simon Ng
-
Patent number: 7622600Abstract: 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: GrantFiled: January 5, 2007Date of Patent: November 24, 2009Assignee: Redland Industries, Inc.Inventor: Wesley Drew Marr
-
Patent number: 7605281Abstract: 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: GrantFiled: August 30, 2004Date of Patent: October 20, 2009Assignee: Nippon Shokubai Co., Ltd.Inventors: Tomoharu Oku, Masanori Nonoguchi, Toshimitsu Moriguchi
-
Patent number: 7592470Abstract: 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: GrantFiled: May 26, 2004Date of Patent: September 22, 2009Assignee: Institut Francais du PetroleInventors: Thierry Lacome, Gerard Hillion, Bruno Delfort, Renaud Revel, Serge Leporq, Gustave Acakpo
-
Patent number: 7582784Abstract: 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: GrantFiled: July 12, 2007Date of Patent: September 1, 2009Assignee: Rohm and Haas CompanyInventors: Rajiv Manohar Banavali, Abraham Benderly
-
Patent number: 7563915Abstract: 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: GrantFiled: May 29, 2007Date of Patent: July 21, 2009Assignee: The Penn State Research FoundationInventors: Jack Vincent Matson, Dheeban Chakravarthi Kannan
-
Patent number: 7553982Abstract: 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: GrantFiled: August 13, 2007Date of Patent: June 30, 2009Assignee: Bio-Alternative, LLCInventor: Martin Allan Morris
-
Patent number: 7550278Abstract: 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: GrantFiled: November 29, 2004Date of Patent: June 23, 2009Assignee: Tsinghua UniversityInventors: Wei Du, Dehua Liu, Lilin Li
-
Patent number: 7550614Abstract: 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: GrantFiled: October 19, 2007Date of Patent: June 23, 2009Assignee: Rohm and Haas CompanyInventors: Rajiv Manohar Banavali, Gregory C. Pierce
-
Patent number: 7514575Abstract: 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: GrantFiled: May 6, 2005Date of Patent: April 7, 2009Assignee: Battelle Energy Allicance, LLCInventors: Daniel M. Ginosar, Robert V. Fox, Lucia M. Petkovic
-
Patent number: 7507846Abstract: 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: GrantFiled: March 17, 2004Date of Patent: March 24, 2009Inventor: Michael F. Pelly
-
Publication number: 20090062559Abstract: 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: ApplicationFiled: August 28, 2008Publication date: March 5, 2009Applicant: SAUBER TECHNOLOGIES, LLCInventors: Michael Philip Doyle, Steve Smith
-
Patent number: 7488837Abstract: 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 mixtureType: GrantFiled: June 28, 2005Date of Patent: February 10, 2009Assignee: Revo International Inc.Inventors: Keiichi Tsuto, Tetsuya Koshikawa
-
Patent number: 7473791Abstract: 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: GrantFiled: January 15, 2004Date of Patent: January 6, 2009Assignee: Tsinghua UniversityInventors: Wei Du, Yuanyuan Xu, Dehua Liu
-
Patent number: 7468450Abstract: 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: GrantFiled: March 22, 2005Date of Patent: December 23, 2008Inventors: Siegfried Peter, Eckhard Weidner
-
Publication number: 20080293956Abstract: 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: ApplicationFiled: April 25, 2008Publication date: November 27, 2008Applicant: Sichuan Gushan Oil Chemical Co. Ltd.Inventors: Jianqiu Yu, Deyu Chen, Junxiong Li, Zihong Chen, Gonghao Chen
-
Patent number: 7452448Abstract: 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: GrantFiled: March 28, 2002Date of Patent: November 18, 2008Assignee: Fuji Oil Company, LimitedInventors: Tadayuki Okada, Kotaro Yamaguchi
-
Patent number: 7420073Abstract: 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: GrantFiled: March 17, 2004Date of Patent: September 2, 2008Assignee: Institut Francais du PetroleInventors: Gérard Hillion, Dominique Le Pennec
-
Patent number: 7420072Abstract: 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: GrantFiled: April 26, 2007Date of Patent: September 2, 2008Assignee: Orbitek, Inc.Inventor: Christian A. Fleisher
-
Publication number: 20080167485Abstract: 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: ApplicationFiled: January 7, 2008Publication date: July 10, 2008Inventor: Rajiv Manohar Banavali
-
Publication number: 20080161588Abstract: 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: ApplicationFiled: December 20, 2007Publication date: July 3, 2008Applicant: HRD CORP. D/B/A MARCUS OIL & CHEMICALInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
-
Patent number: 7367995Abstract: 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: GrantFiled: February 27, 2006Date of Patent: May 6, 2008Assignee: Board of Trustees of Michigan State UniversityInventors: Ramani Narayan, Daniel Graiver, Kenneth W. Farminer
-
Patent number: 7271275Abstract: 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: GrantFiled: October 13, 2004Date of Patent: September 18, 2007Assignee: Kao CorporationInventors: Takanobu Katayama, Nobuhiro Tatsumi, Osamu Tabata
-
Patent number: 7252779Abstract: This invention is a composition that includes a transesterified fatty acid ester resulting from the reaction of a fatty acid ester, in the presence of an acid, with a hydroxyl-containing compound. The fatty acid esters of the invention are selected from those with a carbon number of eight to twenty. The hydroxyl-containing compound is an alcohol having a carbon number between one and eighteen. The resulting composition is useful as a lubricant, as a heat transfer agent, as a rheological modifier and as a corrosion/moisture inhibitor, among other uses.Type: GrantFiled: August 2, 2001Date of Patent: August 7, 2007Assignee: MJ Research Limited PartnershipInventors: Benjamin Mosier, Bryan J. Duffy
-
Patent number: 7227030Abstract: 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: GrantFiled: June 12, 2003Date of Patent: June 5, 2007Inventor: Shiro Saka
-
Patent number: 7145026Abstract: 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: GrantFiled: April 11, 2003Date of Patent: December 5, 2006Assignee: Biodiesel Technologies, Inc.Inventor: Christian A. Fleisher
-
Patent number: 7128766Abstract: 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: GrantFiled: September 25, 2001Date of Patent: October 31, 2006Assignee: Cargill, IncorporatedInventors: Timothy A. Murphy, Robert E. Wainwright
-
Patent number: 7122688Abstract: 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: GrantFiled: September 20, 2004Date of Patent: October 17, 2006Assignee: Iowa State University Research FoundationInventors: Victor Shang-Yi Lin, Daniela Rodica Radu
-
Patent number: 7115760Abstract: 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: GrantFiled: October 31, 2003Date of Patent: October 3, 2006Assignee: Danisco A/SInventors: Flemming Vang Sparsø, Ulrik Engelrud
-
Patent number: 7109363Abstract: 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: GrantFiled: November 29, 2001Date of Patent: September 19, 2006Assignee: Westfalia Separator AGInventors: Karlheinz Brunner, Rainer Frische, Rainer Ricker
-
Patent number: 7091367Abstract: 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: GrantFiled: November 12, 2003Date of Patent: August 15, 2006Assignee: Sulzer ChemtechInventors: Peter Moritz, Peter Faessler, Claudia von Scala, Oliver Bailer
-
Patent number: 7081542Abstract: 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: GrantFiled: October 3, 2002Date of Patent: July 25, 2006Assignee: Archer-Daniels-Midland CompanyInventors: Lewis Jacobs, Immok Lee, George Poppe
-
Patent number: 7074948Abstract: 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: GrantFiled: December 3, 2004Date of Patent: July 11, 2006Assignee: Zenitech LLCInventor: Kenneth Klein
-
Patent number: 7067684Abstract: 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: GrantFiled: December 16, 2004Date of Patent: June 27, 2006Assignee: Cognis Deutschland GmbH & Co. KGInventors: Alfred Westfechtel, Stefan Busch, Elke Grundt, Peter Horlacher
-
Patent number: 7002030Abstract: 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: GrantFiled: October 6, 2003Date of Patent: February 21, 2006Assignee: Raisio Benecol Ltd.Inventors: Tatu Miettenen, Ingmar Wester, Hannu Vanhanen
-
Patent number: 6969771Abstract: 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: GrantFiled: June 21, 2002Date of Patent: November 29, 2005Assignee: Fuji Oil Company, LimitedInventors: Tadayuki Okada, Kotaro Yamaguchi
-
Patent number: 6965044Abstract: 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: GrantFiled: July 5, 2002Date of Patent: November 15, 2005Assignee: Iowa State University Research FoundationInventors: Earl G. Hammond, Tong Wang
-
Patent number: 6960672Abstract: 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: GrantFiled: March 28, 2002Date of Patent: November 1, 2005Assignee: Revo International Inc.Inventors: Masahide Nakayama, Keiichi Tsuto, Takenori Hirano, Tsutomu Sakai, Ayato Kawashima, Hirohisa Kitagawa
-
Patent number: 6943262Abstract: 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: GrantFiled: September 24, 2002Date of Patent: September 13, 2005Assignee: Cargill, IncorporatedInventors: Dharma R. Kodali, Scott C Nivens
-
Patent number: 6933398Abstract: 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: GrantFiled: September 24, 2003Date of Patent: August 23, 2005Inventors: Siegfried Peter, Eckhard Weidner
-
Patent number: 6905850Abstract: 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: GrantFiled: July 2, 2001Date of Patent: June 14, 2005Assignee: Nippon Suisan Kaisha, Ltd.Inventors: Roxana Irimescu, Kiyomi Furihata, Kazuhiko Hata, Tsuneo Yamane
-
Patent number: 6884900Abstract: 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: GrantFiled: October 6, 2003Date of Patent: April 26, 2005Assignee: Cosmo Engineering Co., Ltd.Inventors: Yasuaki Maeda, Mircea Vinatoru, Carmen Eugenia Stavarach, Kunio Iwai, Hideki Oshige
-
Patent number: 6878837Abstract: 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: GrantFiled: April 11, 2003Date of Patent: April 12, 2005Assignee: Institut Francais du PetroleInventors: Laurent Bournay, Gerard Hillion, Pierre Boucot, Jean-Alain Chodorge, Charles Bronner, Alain Forestiere