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)
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Patent number: 8481771Abstract: Processes for producing biodiesel compositions are disclosed. FFAs present in the triglycerides can be removed by reaction with isobutylene, or by Kolbe electrolysis. The Kolbe electrolysis can be performed on the starting material, or on the crude glycerol. The triglycerides are transesterified to form alkyl esters of the fatty acids and glycerol. The transesterification reaction can be catalyzed by an alkoxide, rather than a hydroxide, to help keep the glycerol by-product dry. The alkoxide salt can be neutralized by reaction with a dry acid, such as gaseous hydrogen chloride or sulfuric acid, and the resulting alcohol removed by distillation, and at least a portion of the neutralized salt can be removed by filtration or decantation. The process can provide improved biodiesel yields, and glycerol pure enough for use directly in glycerol ether manufacture.Type: GrantFiled: March 21, 2008Date of Patent: July 9, 2013Assignee: CPS Biofuels, Inc.Inventors: David Bradin, Guerry L. Grune
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Publication number: 20130158277Abstract: Provided herein are estolide base oils and oligomeric compounds prepared from processes that include cross metathesis.Type: ApplicationFiled: December 6, 2012Publication date: June 20, 2013Inventors: Travis Thompson, Kelly Parson, Jakob Bredsguard, Jeremy Forest
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Patent number: 8466305Abstract: The present invention relates to systems and methods of using fatty acid alkyl ester solutions to refine feed stocks before converting the feed stocks into fatty acid fatty acid alkyl esters. In an embodiment, the invention includes a method for producing fatty acid alkyl esters. The method can include mixing a crude lipid feed stock with a refining solution to form a crude product mixture, the refining solution comprising greater than about 10 wt. % fatty acid alkyl esters. The method can include extracting the liquid phase from the crude product mixture to obtain a purified lipid feed stock. The method can also include reacting the purified lipid feed stock with an alcohol to form a product mixture comprising fatty acid alkyl esters. In an embodiment, the invention includes a method of making a fatty acid alkyl ester composition.Type: GrantFiled: April 5, 2011Date of Patent: June 18, 2013Assignee: McNeff Research Consultants, Inc.Inventor: Clayton V. McNeff
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Patent number: 8466304Abstract: The present invention describes a method of producing fatty acid alkyl esters and glycerin implementing a set of transesterification reactions between a vegetable or animal oil and an aliphatic monoalcohol in the presence of a heterogeneous solid catalyst so as to obtain an effluent comprising at least alkyl esters, free glycerol, bonded glycerol and alcohol, wherein at least one stage of separation of at least a portion of the effluent is carried out in order to separate the ester produced and the bonded glycerol, said separation occurring through a membrane.Type: GrantFiled: December 22, 2009Date of Patent: June 18, 2013Assignee: IFP Energies NouvellesInventors: Arnaud Baudot, Laurent Bournay, Eszter Toth
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Patent number: 8449629Abstract: The present invention relates to a process and apparatus for the production of carboxylic acid esters and/or biodiesel fuel from feedstocks containing fatty acids, glycerated fatty acids, and glycerin by reactive distillation. Specifically, in one embodiment, the present invention relates to the production of biodiesel fuels having low glycerin, water, and sulfur content on an industrial scale.Type: GrantFiled: December 9, 2011Date of Patent: May 28, 2013Assignee: Endicott Biofuels II, LLCInventor: William Douglas Morgan
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Patent number: 8445709Abstract: The present invention relates to systems and methods for producing and/or refining alkyl ester compositions. In an embodiment the invention includes a method of producing a refined fatty acid alkyl ester composition. The method can include contacting a fatty acid feedstock and an alcohol with a first metal oxide catalyst at a temperature of greater than 200 degrees Celsius and a pressure of greater than 500 psi to form an unrefined fatty acid alkyl ester composition. The method can further include combining the unrefined fatty acid alkyl ester composition with dimethyl carbonate to form a refining mixture. The method can also include contacting the refining mixture with a second metal oxide catalyst at a temperature of greater than 100 degrees Celsius to form a refined fatty acid alkyl ester composition. Other embodiments are also described herein.Type: GrantFiled: June 9, 2010Date of Patent: May 21, 2013Assignee: McNeff Research Consultants, Inc.Inventors: Clayton V. McNeff, Larry C. McNeff, Bingwen Yan, Daniel Thomas Nowlan
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Patent number: 8445400Abstract: The present invention provides a novel glycerol-based heterogeneous solid acid catalyst by simultaneous partial carbonization and sulfonation of crude glycerol obtained as a by-product during the biodiesel process. Solid acid catalyst with similar activity is also prepared from glycerol pitch (by-product of fat splitting) and technical grade glycerol. These glycerol-based solid acid catalysts are employed for esterification of fatty acids and fatty acid present in the high and low free fatty acid (FFA) containing vegetable oils like rice bran, karanja and jatropha; fatty acid distillate; deodorizer distillate and acid oil which are being used as raw materials for the preparation of biodiesel. These catalysts are highly active, reusable and simplify the biodiesel process particularly for fatty acids or high FFA containing vegetable oils by replacing the traditional homogeneous mineral acid catalysts.Type: GrantFiled: October 26, 2007Date of Patent: May 21, 2013Assignee: Council of Scientific & Industrial ResearchInventors: Bethala Lakshmi Anu Prabhavathi Devi, Katkam Nadpi Gangadhar, Potharaju Seetharamanjaneya Sai Prasad, Rachapudi Badari Narayana Prasad
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Publication number: 20130096331Abstract: A method of producing a interesterified oil includes providing sunflower oil comprising no more than about 4% total saturated fat and interesterifying the sunflower oil. Another method of producing a interesterified oil includes providing sunflower oil comprising about 3.3% or less total combined palmitic acid (16:0) and stearic acid (18:0), and interesterifying the sunflower oil.Type: ApplicationFiled: December 5, 2012Publication date: April 18, 2013Applicant: DOW AGROSCIENCES LLCInventor: Dow AgroSciences LLC
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Patent number: 8420841Abstract: A method of manufacturing a biodiesel fuel that comprises generating micro-droplets of a first reactant and mixing the micro-droplets of the first reactant with a second reactant that is substantially immiscible with the first reactant. The method also comprises transferring the mixture of the first reactant and second reactant into a transesterification reaction vessel. The first reactant is one of an alcohol or oil, and the second reactant is the other of the oil or the alcohol.Type: GrantFiled: September 13, 2010Date of Patent: April 16, 2013Assignee: Texas Tech University SystemInventor: Uzi Mann
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Patent number: 8420840Abstract: A method comprising providing a starting composition comprising a polyunsaturated fatty acid, a polyunsaturated fatty ester, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated triglyceride, or a mixture thereof; self-metathesizing the starting composition or cross-metathesizing the starting composition with at least one short-chain olefin in the presence of a metathesis catalyst to form self-/cross-metathesis products comprising: cyclohexadiene; at least one olefin; and one or more acid-, ester-, or salt-functionalized alkene; and reacting cyclohexadiene to produce at least one cycloalkane or cycloalkane derivatives.Type: GrantFiled: December 2, 2011Date of Patent: April 16, 2013Inventor: Edwin S. Olson
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Patent number: 8404005Abstract: In a method and system to produce biodiesel using an improved catalytic transesterification process, a first reactant and a second reactant are dispersed to form a laminar slug flow pattern within a microchannel of a microreactor, the first reactant and the second reactant being immiscible. The first reactant and the second reactant are mixed, thereby triggering a reaction between them to produce the biodiesel and glycerol, the mixing being convection-enhanced by shear stress induced circulation occurring within each slug of the reactants. The reaction takes place under a pressure that is less than 5 psi and under a temperature that is less than 70 degrees Celsius. Separation of the glycerol from the biodiesel occurs simultaneously with the mixing. Several microreactors are coupled in parallel to improve throughput of the biodiesel.Type: GrantFiled: September 10, 2009Date of Patent: March 26, 2013Assignee: Board of Regents, The University of Texas SystemInventors: Brian H. Dennis, Richard E. Billo, Christopher R. Oliver, John W. Priest, Elinor Kolesar
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Patent number: 8378132Abstract: Transesterification systems and methods for producing methyl ester are disclosed. In one embodiment, a method for producing methyl ester includes introducing a first charge into a reactor. The first charge contains a triglyceride-containing fat and an alcohol. The method can also include performing a first transesterification reaction in which the triglyceride-containing fat is reacted with the alcohol to produce a first product. The method can further include settling the first product into a methyl ester-containing layer and a glycerol-containing layer, decanting the glycerol-containing layer after settling from the reactor, mixing a second charge with the first product, and performing a second transesterification reaction after mixing the second charge with the first product.Type: GrantFiled: February 15, 2008Date of Patent: February 19, 2013Inventor: Daniel W. Lemke
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Patent number: 8361172Abstract: In the present invention, a fuel composition and a process for making the same are disclosed. Specifically, in the present invention, triglycerides useful for distillate fuels are described along with their method for preparation from Fischer-Tropsch acid by-products and the glycerol by-product from biodiesel generation. By using these two by-product streams, the overall efficiency of both processes is improved and a new source of distillate fuels is created. These triglycerides can be used to improve the lubricity of Fischer-Tropsch derived distillate fuels. In addition, these triglycerides also have low melting points and have viscosities compatible with distillate fuels.Type: GrantFiled: December 16, 2009Date of Patent: January 29, 2013Assignee: Chevron U.S.A. Inc.Inventor: Dennis J. O'Rear
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Patent number: 8362288Abstract: A process for preparing a composition of alcoholic esters of straight chain monocarboxylic acids containing 6 to 26 carbon atoms and glycerin, starting from a vegetable or animal oil, neutral or acidic, virgin or recycled with mono-alcohols containing 1 to 18 atoms, in the presence of a zinc aluminate catalyst and in the presence of a controlled quantity of water, can directly produce, in one or more steps, an ester which can be used as a propellant or fuel along with glycerin having improved purity containing a reduced quantity of ethers by using a partially dried catalyst.Type: GrantFiled: September 10, 2010Date of Patent: January 29, 2013Assignee: IFP Energies NouvellesInventors: Vincent Coupard, Sylvie Maury, Veronique Pugnet
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Patent number: 8350069Abstract: The present invention provides a method and apparatus for reacting a natural oil with a short chain alcohol in the presence of alkaline catalyst, in which a mixture of natural oil, short chain alcohol and alkaline catalyst is fed in one direction along a pipe reactor under transitional or turbulent conditions, so that the reactants are mixed in a direction normal to the flow direction to a greater degree than in a direction parallel to the flow direction or so that the reactants are mixed in a direction normal to the flow direction, such that the time taken for 90% of the elements of fluid to pass through the reactor is within 20% of the mean residence time of reactant in the reactor. There is also provided a ship, comprising means for storing a raw material used in the synthesis of biodiesel, a plant for the synthesis of biodiesel and means for storing the biodiesel synthesized.Type: GrantFiled: October 19, 2007Date of Patent: January 8, 2013Assignee: Renewable Holdings LimitedInventors: Owen Matthew Davies, Richard David Jackson
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Patent number: 8350071Abstract: The present invention describes a method of producing fatty acid alkyl esters and glycerin implementing, in a reaction section, a set of transesterification reactions between a vegetable or animal oil and an aliphatic monoalcohol, and using a heterogeneous solid catalyst, comprising: a) a stage of recontacting the effluent coming from the reaction section, and separated from the excess alcohol, with a glycerin phase, b) a stage of mixing said effluent with said glycerin phase, and c) a glycerin phase decantation stage. The supernatent ester phase obtained after decantation is then optionally sent to a coalescer, also allowing separation of the glycerin, then to a purification stage by adsorption on solids.Type: GrantFiled: June 9, 2008Date of Patent: January 8, 2013Assignee: IFP Energies nouvellesInventors: Abdelhakim Koudil, Romain Rousset, Laurent Bournay, Franck Gaviot-Blanc
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Patent number: 8333905Abstract: The present invention includes a polyol produced according to the process comprising reacting a multifunctional alcohol with a first multifunctional component to form a reaction product and reacting the reaction product with a vegetable oil to form a polyol. The present invention also relates to the material comprising the reaction product of an A-side and a B-side, wherein the A-side comprises an isocyanate and the B-side comprises the product formed by the process comprising the steps of reacting a multifunctional alcohol with a first multifunctional component to form a precursor polyol and then reacting the precursor polyol with a vegetable oil to form a vegetable based polyol with selectable functionality.Type: GrantFiled: October 31, 2007Date of Patent: December 18, 2012Assignee: Tandem Polymers, Inc.Inventors: Thomas M. Kurth, Richard A. Kurth, Robert B. Turner, Les P. Kreifels, Todd A. Van Thomme
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Patent number: 8328997Abstract: This invention relates to the design of a process by intermittent dielectric heating combined with a recycling system. This process consists in subjecting reagents to electromagnetic waves selected in the frequencies ranging between 300 GHz and 3 MHz intermittently using a recycling system. This process enables the treatment of oils that are hardly absorbent as well as great investment savings. This process enables operation on different scales, whether in laboratories, on a semi-industrial or industrial scale, without forfeiting the advantages of continuous dielectric heating.Type: GrantFiled: June 29, 2009Date of Patent: December 11, 2012Assignee: Aldivia SAInventors: Pierre Charlier De Chily, Mikaële Raynard
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Patent number: 8324413Abstract: In the present invention, a fuel composition and a process for making the same are disclosed. Specifically, in the present invention, triglycerides useful for distillate fuels are described along with their method for preparation from Fischer-Tropsch acid by-products and the glycerol by-product from biodiesel generation. By using these two by-product streams, the overall efficiency of both processes is improved and a new source of distillate fuels is created. These triglycerides can be used to improve the lubricity of Fischer-Tropsch derived distillate fuels. In addition, these triglycerides also have low melting points and have viscosities compatible with distillate fuels.Type: GrantFiled: December 16, 2009Date of Patent: December 4, 2012Assignee: Texaco Inc.Inventor: Dennis J. O'Rear
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Publication number: 20120289725Abstract: 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 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 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.Type: ApplicationFiled: April 11, 2012Publication date: November 15, 2012Inventors: Gerald S. Jones, JR., Scott A. Goodrich, Joseph P. St. Laurent
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Patent number: 8304566Abstract: Processes and apparatus produce economically feasible biodiesel without subsidies. Toward that end, integrated small plants process materials containing lipids with anhydrous bioethanol as solvent and reactant, and sulfuric acid and potassium hydroxide mainly as catalysts to produce up to 3 million gallons of biodiesel per plant per year. The product is predominantly fatty acids ethyl esters (FAEE) and a chemically-enhanced organic fertilizer as byproduct. The raw material may include a wide variety of non-edible solid matter that contains lipids, which normally have from 0.5% to 80% by weight of free fatty acids in total oils. Multiple apparatus makes this process feasible. In addition to not competing with food production, since they supply fertilizer for small scale farmers, the processes and apparatus allow sustainable liquid fuel production.Type: GrantFiled: March 9, 2012Date of Patent: November 6, 2012Inventor: Antonio Cantizani
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Patent number: 8288573Abstract: The present invention provides a process for preparing a bio-diesel, comprising, in the presence of an alkaline metal compound, reacting an oil-fat with C1-C6 monohydric alcohol in a reactor at a reaction temperature of from 130 to 280° C. and a reaction pressure of from 1 to 12 MPa, separating fatty acid esters from the reacted materials, so as to produce the bio-diesel, wherein said alkaline metal compound is present in an amount of 0.001-0.07 wt %, in terms of the metal thereof, relative to the weight of the oil-fat. The process provided in the present invention has the advantages of great throughput and high yield of the bio-diesel.Type: GrantFiled: December 15, 2006Date of Patent: October 16, 2012Assignees: China Petroleum & Chemical Corporation, Research Institute of Petroleum Processing, SinopecInventors: Haijing Wang, Zexue Du, Enze Min, Guoqiang Gao
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Patent number: 8288574Abstract: Method for producing C3H5(OH)3 and at least one of fatty acid methyl ester (FAME) and fatty acid ethyl ester (FAEE) includes mixing vegetable oils and animal fats, at least one of CH3OH and C2H5OH and at least one first catalyst to transesterify a portion of triglycerides and provide a first mixture. The first mixture is separated, with a first light phase being withdrawn and fed into a second mixer where it is mixed with at least one second catalyst to transesterify a further portion of the triglycerides to provide a second mixture. The second mixture is separated, with a second light phase being withdrawn and mixed with soapless C3H5(OH)3 to provide a dispersion which is separated by density difference. A phase containing at least one of raw FAME and raw FAEE is mixed with an aqueous acid, washed with water, with the water being expelled to provide FAME and FAEE product.Type: GrantFiled: September 5, 2008Date of Patent: October 16, 2012Assignee: Lurgi GmbHInventors: Rudolf Boensch, Helmut Saft, Peter Mitschke, Henning Buchold
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Patent number: 8252949Abstract: The present invention relates to a process for producing fatty acid alkyl esters from fats/oils and a C1 to C5 lower alcohol as reaction starting materials with a solid catalyst, wherein the starting materials and reaction products in a reaction system where the degree of conversion of fats/oils is 50 mol % or more are reacted in such a state as to be in one-liquid phase, or the starting materials and reaction products in a reaction system at a stage with the highest degree of conversion of fats/oils are reacted in such a state as to be in one-liquid phase.Type: GrantFiled: June 11, 2008Date of Patent: August 28, 2012Assignee: Kao CorporationInventors: Yuichiro Seki, Takanobu Katayama, Katsutoshi Yamamoto
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Patent number: 8242295Abstract: Disclosed is a process for producing a fatty alkyl ester and glycerin, including step 1 of reacting fats and oils with C1 to C5 lower alcohols, step 2 of removing the lower alcohols discharged from the outlet of a rector in step 1 until the lower alcohol content is reduced to 8 wt % or less, step 3 of separating the product obtained in step 2 into oil and aqueous phases, step 4 of reacting the oil phase obtained in step 3 with lower alcohols in the presence of an acid catalyst, and step 5 of separating the product discharged from the outlet of a reactor in step 4 into oil and aqueous phases thereby giving fatty acid alkyl esters and glycerin, as well as a process for producing fatty alcohols from hydrogen and the fatty acid alkyl esters obtained in the above process.Type: GrantFiled: December 19, 2006Date of Patent: August 14, 2012Assignee: Kao CorporationInventors: Yuichiro Seki, Nobuhiro Tatsumi, Takanobu Katayama
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Patent number: 8227015Abstract: A process for extraction of crude oil from DDGS and producing corn distillers meal that may be used as a livestock supplement is disclosed. For example, the corn distillers meal may be used as a crude protein supplement for use in a livestock feed diet or a poultry feed diet.Type: GrantFiled: September 26, 2007Date of Patent: July 24, 2012Inventors: Keith Bruinsma, Donald L. Endres
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Patent number: 8227632Abstract: A process of preparing alkyl esters of free fatty acids, including, but not limited to, biodiesel, is described herein.Type: GrantFiled: June 18, 2010Date of Patent: July 24, 2012Assignee: Philadelphia Fry-O-DieselInventors: William Wesley Berry, Brian J. Ratigan
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Patent number: 8222439Abstract: The invention relates to a process for the production of carboxylic acid esters by esterification of carboxylic acids and/or transesterification of carboxylic acid esters with alcohols in the presence of a liquid metal catalyst, characterized in that the liquid metal catalyst is the alkaline earth metal salt of a carboxylic acid.Type: GrantFiled: July 24, 2006Date of Patent: July 17, 2012Assignee: BDI Biodiesel International AGInventors: Wolfgang Glasl, Martin Mittelbach, Matthaeus Siebenhofer, Erich Jeitler, Wilhelm Hammer, Helmut Gossler, Michael Koncar
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Patent number: 8212062Abstract: The present invention relates to a method for producing fatty acid alkyl esters as well as cellulosic simplified sugars, shortened protein polymers, amino acids, or combination thereof resulting from the simultaneous esterification and hydrolysis, alcoholysis, or both of algae and other oil containing materials containing free fatty acids (FFA), glycerides, or combination thereof as well as polysaccharides, cellulose, hemicellulose, lignocellulose, protein polymers, or combination thereof in presences of an alcohol and an acid catalyst.Type: GrantFiled: April 2, 2008Date of Patent: July 3, 2012Assignee: Inventure Chemical, Inc.Inventors: William Wes Berry, Mark G. Tegen, Stephen L. Hillis
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Patent number: 8207362Abstract: 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: GrantFiled: November 21, 2008Date of Patent: June 26, 2012Assignee: Bio-Alternative, LLCInventor: Martin Allan Morris
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Publication number: 20120142953Abstract: The present invention relates to a method for the transesterification of a hydroxylated oil including two consecutive transesterification steps performed in the presence of a light alcohol (methanol or ethanol) and a basic catalyst under temperature, pressure and alcohol/oil weight ratio conditions enabling the nearly total conversion of the hydroxylated oil into fatty acid esters. Characteristically, a resulting directly from the first transestrefication step in order to obtain a reaction mixture including, in particular, hydroxylated fatty acid esters and glycerol. Said reaction mixture is subjected to a separation step that makes it possible to obtain a less dense phase predominantly consisting of fatty esters and a denser phase predominantly consisting of glycerol and water and fatty acid soaps. The second transesterification step is performed on the less dense phase, with said light alcohol and said basic catalyst are added thereto.Type: ApplicationFiled: November 10, 2009Publication date: June 7, 2012Inventors: Jean-Francois Devaux, Georges Martino-Gauchi, Jean-Yves Balouin, Patrice Iafrate
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Patent number: 8182556Abstract: 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: GrantFiled: October 7, 2011Date of Patent: May 22, 2012Assignee: Haliae Development, LLCInventor: Aniket Kale
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Patent number: 8178703Abstract: Methods to convert biobased oils, oil derivatives, and modified oils to highly functionalized esters, ester polyols, amides, and amide polyols. The products can be used to make polyurethane and polyester films and foams.Type: GrantFiled: June 8, 2011Date of Patent: May 15, 2012Assignee: Battelle Memorial InstituteInventors: Herman Paul Benecke, Daniel B. Garbark, Bhima Rao Vijayendran
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Patent number: 8163946Abstract: 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: GrantFiled: May 19, 2009Date of Patent: April 24, 2012Assignee: Wayne State UniversityInventors: Shuli Yan, Steven O. Salley, K. Y. Simon Ng
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Patent number: 8152870Abstract: 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: GrantFiled: April 6, 2011Date of Patent: April 10, 2012Assignee: Heliae Development, LLCInventor: Aniket Kale
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Patent number: 8129553Abstract: Provided is a method of producing fatty acid alkyl esters at high reaction efficiency, wherein the impurities inhibiting the reaction such as water are removed sufficiently. The fatty acid alkyl esters are produced efficiently, by a method of producing fatty acid alkyl esters, at least comprising (A) a step of removing at least water from an oil/fat raw material, (B) a step of converting the fatty acid glycerides contained in the oil/fat raw material into fatty acid alkyl esters and reducing the triglyceride content in the fatty acid alkyl esters obtained to 0.1 wt % or less by fine-particle dispersion and agitation, and (C) a step of separating at least glycerol from the mixture containing fatty acid alkyl esters.Type: GrantFiled: July 2, 2007Date of Patent: March 6, 2012Assignees: Wakamatsu Corporation, Toyota Tsusyo Corporation, Toyota Chemical Engineering Co., Ltd.Inventors: Mikito Wakamatsu, Teruhiro Isayama, Makoto Hattori, Hiroshi Murakami, Nobuaki Hamanishi, Takeshi Sakakibara
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Patent number: 8129324Abstract: Fatty esters of oligoesters of a dicarboxylic acid and a polyol retaining at least one free hydroxyl group, particularly of the formula (I): R1—[OR2O—C(O)—R3—(O)C—]m—R4 (I), where R1 is H, a monocarboxylic acid group, or R6O—[C(O)—R3—(O)C]—; R2s are residues of polyols having at least one substituent free hydroxyl; R3s are hydrocarbylene; R4 is —OH, —OM where M is a salt forming metal, amine or ammonium, —OR6, or —OR2O—R7; R5 is C7 to C21 hydrocarbyl; R6 is C8 to C22 hydrocarbyl; R7 is H, or —C(O)R5; and m is 1 to 20; provided that at least one of R1 and R4 is or includes a C8 to C22 group, are surfactants. A range of surfactant properties can be obtained by varying the molecules within these ranges. Especially where R2 is derived from a higher polyol e.g. sorbitol, R3 is C2 to C6, and the fatty terminal group is C8 to C14, the products can be highly water soluble and effective oil in water emulsifiers.Type: GrantFiled: October 18, 2005Date of Patent: March 6, 2012Assignee: Croda International PLCInventors: Hanamanthsa S Bevinakatti, Alan G Waite
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Patent number: 8124801Abstract: Processes for preparation of fatty acid alkyl esters are described herein. The processes include contacting fatty acid glycerides with alcohols in the presence of a catalyst separating the reaction products from the catalyst, and separating the fatty acid alkyl esters from the reaction products. The catalyst includes a metal from Group VIB of the Periodic Table and an element from Group VA of the Periodic Table.Type: GrantFiled: June 24, 2009Date of Patent: February 28, 2012Assignee: Benefuel Inc.Inventors: Darbha Srinivas, Paul Ratnassamy, Sanjeevani Amrit Pardhy, Thirumalaiswamy Raja, Shilpa Shirish Deshpande, Vijay Vasant Bokade, Kashinath Joti Wagmare, Arshia Altaf Lalljee, Surya Prakash Babu, Karukappadath Kunjimoideen Abdul Rashid, Khaliji Anas, Chennampilly Ummer Aniz
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Patent number: 8119824Abstract: 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 amType: GrantFiled: June 20, 2006Date of Patent: February 21, 2012Assignee: Tokyo Institute of TechnologyInventor: Michikazu Hara
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Patent number: 8070836Abstract: In one aspect, a process for producing a biofuel comprises reacting a feed material that comprises a glyceride with an alcohol in the presence of a catalytic composition such that at least some of the glyceride in the feed material is converted into a biofuel mixture that comprises glycerol and the corresponding alcoholic ester of the glyceride. The catalytic composition comprises a heterogeneous catalyst and a homogeneous catalyst. The heterogeneous catalyst and the homogeneous catalyst have a synergistic effect in catalyzing the reaction of the glyceride in the feed material with the alcohol.Type: GrantFiled: October 16, 2008Date of Patent: December 6, 2011Assignee: Wayne State UniversityInventors: K. Y. Simon Ng, Manhoe Kim, Steven O. Salley
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Patent number: 8048468Abstract: Provided are a glyceride oil composition derived from a fish oil and a preparation method thereof. The composition includes docosahexaenoic acid (DHA) and docosapentaenoic acid (DPA) with a content of 45 to 95% by weight and eicosapentaenoic acid (EPA) with a content of 0.001 to 13% by weight among constituent fatty acids, and a saturated fatty acid having 16 to 18 carbon atoms, which is bonded at 1- and 3-positions, with a content of 0.001 to 5% by weight among constituent fatty acids, in which a weight ratio of docosahexaenoic acid (DHA)/docosapentaenoic acid (DPA) is 0.5 to 8 and a weight ratio of docosahexaenoic acid (DHA)/eicosapentaenoic acid (EPA) is 3.5 to 15. The glyceride oil composition derived from fish oil has nutritional and physiological superiority due to containing a great amount of polyunsaturated fatty acids such as DHA and DPA in a form of glyceride, and can minimize disadvantages of EPA such as inhibition of ?-6 fatty acid metabolism by containing a low amount of EPA.Type: GrantFiled: September 5, 2007Date of Patent: November 1, 2011Assignee: Ilshin Wells Co., Ltd.Inventors: Dong-Hun Yoon, Kwang-Hoon Yoon, Gi-Wang Han, Moon-Won Lee, Young-Ho Lee, Sang-Hyuk Park
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Patent number: 8039652Abstract: Transesterification, esterification, and esterification-transesterification (both one-step and two-step) for producing biofuels. The process may be enhanced by one or more of the following: 1) applying microwave or RF energy; 2) passing reactants over a heterogeneous catalyst at sufficiently high velocity to achieve high shear conditions; 3) emulsifying reactants with a homogeneous catalyst; or 4) maintaining the reaction at a pressure at or above autogeneous pressure. Enhanced processes using one or more of these steps can result in higher process rates, higher conversion levels, or both.Type: GrantFiled: April 14, 2010Date of Patent: October 18, 2011Assignee: Carnegie Mellon UniversityInventors: Marc A. Portnoff, David A. Purta, Margaret A. Nasta, Jingfeng Zhang, Faiz Pourarian
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Patent number: 7994354Abstract: Methods to convert biobased oils, oil derivatives, and modified oils to highly functionalized esters, ester polyols, amides, and amide polyols. The products can be used to make polyurethane and polyester films and foams.Type: GrantFiled: April 26, 2006Date of Patent: August 9, 2011Assignee: Battelle Memorial InstituteInventors: Herman Paul Benecke, Daniel B. Garbark, Bhima Rao Vijayendran
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Patent number: 7910758Abstract: 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: GrantFiled: December 20, 2007Date of Patent: March 22, 2011Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20110060153Abstract: The present invention relates to systems and methods for producing and/or refining alkyl ester compositions. In an embodiment the invention includes a method of producing a refined fatty acid alkyl ester composition. The method can include contacting a fatty acid feedstock and an alcohol with a first metal oxide catalyst at a temperature of greater than 200 degrees Celsius and a pressure of greater than 500 psi to form an unrefined fatty acid alkyl ester composition. The method can further include combining the unrefined fatty acid alkyl ester composition with dimethyl carbonate to form a refining mixture. The method can also include contacting the refining mixture with a second metal oxide catalyst at a temperature of greater than 100 degrees Celsius to form a refined fatty acid alkyl ester composition. Other embodiments are also described herein.Type: ApplicationFiled: June 9, 2010Publication date: March 10, 2011Applicant: MCNEFF RESEARCH CONSULTANTS, INC.Inventors: Clayton V. McNeff, Larry C. McNeff, Bingwen Yan, Daniel Thomas Nowlan
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Publication number: 20110054200Abstract: Described herein are systems and processes for the transesterification of a variety of feedstocks, such as in the form of glyceride-containing vegetable oils, glyceride-containing animal oils, and glyceride-containing algal oils, into biodiesel products using solid, heterogeneous catalysts.Type: ApplicationFiled: August 31, 2010Publication date: March 3, 2011Inventors: Yang Cai, Jennifer A. Nieweg, Wayne Anthony Turner, Carla Kern Wilkinson
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Publication number: 20110015417Abstract: The invention provides methods of cultivating oil-bearing microbes using xylose alone or in combination with other depolymerized cellulosic material. Also provided are microorganisms comprising an exogenous gene encoding a polysaccharide degrading enzyme, such as a cellulase, a hemicellulase, a pectinase, or a driselase. Some methods of microbial fermentation are provided that comprise the use of xylose and depolymerized cellulosic materials for the production of oil-bearing microorgansims.Type: ApplicationFiled: April 30, 2010Publication date: January 20, 2011Applicant: Solazyme, Inc.Inventors: Donald E. Trimbur, Chung-Soon Im, Harrison F. Dillon, Anthony G. Day, Scott Franklin, Anna Coragliotti
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Patent number: 7872149Abstract: 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: GrantFiled: September 19, 2007Date of Patent: January 18, 2011Assignee: Best Energies, Inc.Inventors: Donald Leroy Bunning, Louis A. Kapicak, Thomas Arthur Maliszewski, David James Shreck
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Patent number: 7834203Abstract: The object of this invention is to provide a method of producing a bio-diesel oil in a great amount in a relatively short time, in which oil/fat and alcohol, used as reactants, are homogeneously mixed with each other to form a single liquid phase mixture which effectively react with each other. The method includes transesterifying the oil/fat and alcohol in the presence of alkyl ester. Additionally, in the method, alkyl ester is added to a mixture of the oil/fat and alcohol by recycling alkyl ester as a product to the mixture. Furthermore, the method includes (a) an acidic catalyst, and (b) transesterifying the pre-esterified oil/fat with alcohol in the presence of alkyl ester.Type: GrantFiled: March 8, 2004Date of Patent: November 16, 2010Assignee: Korea Institute of Energy ResearchInventors: Jin-Suk Lee, Deog-Keun Kim, Soon-Chul Park, Joon-Pyo Lee, Sung-Hyun Kim, Keun-Hoo Lee
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Patent number: 7772414Abstract: A method for producing a biodiesel fuel product from biological material is disclosed which comprises extracting lipids from the biological material with a pure or alcohol-modified supercritical fluid in an extractor, passing the extract directly into a reactor wherein a transesterification reaction is induced between the extracted lipids and alcohol with additional alcohol added if needed, forming glycerol and fatty acid alkyl esters, passing the mixture into one or more separators to remove the glycerol and fatty acid alkyl ester products, removing wastes, and recycling the critical fluid solvent and unreacted alcohol to the extractor. An improvement to biodiesel preparation is afforded by the simplification of the extraction and reaction processes into a single flowing system. According to the invention, a biodiesel fatty acid alkyl ester product can be prepared directly from biological material feedstock, such as oil-containing seeds, without the need for prior isolation of the oil.Type: GrantFiled: November 13, 2007Date of Patent: August 10, 2010Assignee: Aerophase, Inc.Inventors: Brooks Michael Hybertson, Brian N. Hansen