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: 8481771
    Abstract: 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: Grant
    Filed: March 21, 2008
    Date of Patent: July 9, 2013
    Assignee: CPS Biofuels, Inc.
    Inventors: David Bradin, Guerry L. Grune
  • Publication number: 20130158277
    Abstract: Provided herein are estolide base oils and oligomeric compounds prepared from processes that include cross metathesis.
    Type: Application
    Filed: December 6, 2012
    Publication date: June 20, 2013
    Inventors: Travis Thompson, Kelly Parson, Jakob Bredsguard, Jeremy Forest
  • Patent number: 8466305
    Abstract: 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: Grant
    Filed: April 5, 2011
    Date of Patent: June 18, 2013
    Assignee: McNeff Research Consultants, Inc.
    Inventor: Clayton V. McNeff
  • Patent number: 8466304
    Abstract: 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: Grant
    Filed: December 22, 2009
    Date of Patent: June 18, 2013
    Assignee: IFP Energies Nouvelles
    Inventors: Arnaud Baudot, Laurent Bournay, Eszter Toth
  • Patent number: 8449629
    Abstract: 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: Grant
    Filed: December 9, 2011
    Date of Patent: May 28, 2013
    Assignee: Endicott Biofuels II, LLC
    Inventor: William Douglas Morgan
  • Patent number: 8445709
    Abstract: 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: Grant
    Filed: June 9, 2010
    Date of Patent: May 21, 2013
    Assignee: McNeff Research Consultants, Inc.
    Inventors: Clayton V. McNeff, Larry C. McNeff, Bingwen Yan, Daniel Thomas Nowlan
  • Patent number: 8445400
    Abstract: 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: Grant
    Filed: October 26, 2007
    Date of Patent: May 21, 2013
    Assignee: Council of Scientific & Industrial Research
    Inventors: Bethala Lakshmi Anu Prabhavathi Devi, Katkam Nadpi Gangadhar, Potharaju Seetharamanjaneya Sai Prasad, Rachapudi Badari Narayana Prasad
  • Publication number: 20130096331
    Abstract: 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: Application
    Filed: December 5, 2012
    Publication date: April 18, 2013
    Applicant: DOW AGROSCIENCES LLC
    Inventor: Dow AgroSciences LLC
  • Patent number: 8420841
    Abstract: 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: Grant
    Filed: September 13, 2010
    Date of Patent: April 16, 2013
    Assignee: Texas Tech University System
    Inventor: Uzi Mann
  • Patent number: 8420840
    Abstract: A method comprising providing a starting composition comprising a polyunsaturated fatty acid, a polyunsaturated fatty ester, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated triglyceride, or a mixture thereof; self-metathesizing the starting composition or cross-metathesizing the starting composition with at least one short-chain olefin in the presence of a metathesis catalyst to form self-/cross-metathesis products comprising: cyclohexadiene; at least one olefin; and one or more acid-, ester-, or salt-functionalized alkene; and reacting cyclohexadiene to produce at least one cycloalkane or cycloalkane derivatives.
    Type: Grant
    Filed: December 2, 2011
    Date of Patent: April 16, 2013
    Inventor: Edwin S. Olson
  • Patent number: 8404005
    Abstract: 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: Grant
    Filed: September 10, 2009
    Date of Patent: March 26, 2013
    Assignee: Board of Regents, The University of Texas System
    Inventors: Brian H. Dennis, Richard E. Billo, Christopher R. Oliver, John W. Priest, Elinor Kolesar
  • Patent number: 8378132
    Abstract: 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: Grant
    Filed: February 15, 2008
    Date of Patent: February 19, 2013
    Inventor: Daniel W. Lemke
  • Patent number: 8361172
    Abstract: 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: Grant
    Filed: December 16, 2009
    Date of Patent: January 29, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventor: Dennis J. O'Rear
  • Patent number: 8362288
    Abstract: 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: Grant
    Filed: September 10, 2010
    Date of Patent: January 29, 2013
    Assignee: IFP Energies Nouvelles
    Inventors: Vincent Coupard, Sylvie Maury, Veronique Pugnet
  • Patent number: 8350069
    Abstract: 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: Grant
    Filed: October 19, 2007
    Date of Patent: January 8, 2013
    Assignee: Renewable Holdings Limited
    Inventors: Owen Matthew Davies, Richard David Jackson
  • Patent number: 8350071
    Abstract: 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: Grant
    Filed: June 9, 2008
    Date of Patent: January 8, 2013
    Assignee: IFP Energies nouvelles
    Inventors: Abdelhakim Koudil, Romain Rousset, Laurent Bournay, Franck Gaviot-Blanc
  • Patent number: 8333905
    Abstract: 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: Grant
    Filed: October 31, 2007
    Date of Patent: December 18, 2012
    Assignee: Tandem Polymers, Inc.
    Inventors: Thomas M. Kurth, Richard A. Kurth, Robert B. Turner, Les P. Kreifels, Todd A. Van Thomme
  • Patent number: 8328997
    Abstract: 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: Grant
    Filed: June 29, 2009
    Date of Patent: December 11, 2012
    Assignee: Aldivia SA
    Inventors: Pierre Charlier De Chily, Mikaële Raynard
  • Patent number: 8324413
    Abstract: 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: Grant
    Filed: December 16, 2009
    Date of Patent: December 4, 2012
    Assignee: Texaco Inc.
    Inventor: Dennis J. O'Rear
  • Publication number: 20120289725
    Abstract: The present invention provides a novel approach for the preparation of fatty alcohol esters of ?-hydroxy carboxylic acids. In one form of the invention, the target fatty alcohol ester of ?-hydroxy carboxylic acid is produced by converting a lower alkyl ester of ?-hydroxy carboxylic acid into a fatty alcohol ester of ?-hydroxy carboxylic acid via alcoholysis (i.e., transesterification). The transesterification process is an equilibrium reaction, catalyzed chemically (i.e., with acids or bases) or enzymatically, that is shifted in the desired direction to produce the desired product. One 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: Application
    Filed: April 11, 2012
    Publication date: November 15, 2012
    Inventors: Gerald S. Jones, JR., Scott A. Goodrich, Joseph P. St. Laurent
  • Patent number: 8304566
    Abstract: 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: Grant
    Filed: March 9, 2012
    Date of Patent: November 6, 2012
    Inventor: Antonio Cantizani
  • Patent number: 8288573
    Abstract: 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: Grant
    Filed: December 15, 2006
    Date of Patent: October 16, 2012
    Assignees: China Petroleum & Chemical Corporation, Research Institute of Petroleum Processing, Sinopec
    Inventors: Haijing Wang, Zexue Du, Enze Min, Guoqiang Gao
  • Patent number: 8288574
    Abstract: 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: Grant
    Filed: September 5, 2008
    Date of Patent: October 16, 2012
    Assignee: Lurgi GmbH
    Inventors: Rudolf Boensch, Helmut Saft, Peter Mitschke, Henning Buchold
  • Patent number: 8252949
    Abstract: 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: Grant
    Filed: June 11, 2008
    Date of Patent: August 28, 2012
    Assignee: Kao Corporation
    Inventors: Yuichiro Seki, Takanobu Katayama, Katsutoshi Yamamoto
  • Patent number: 8242295
    Abstract: 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: Grant
    Filed: December 19, 2006
    Date of Patent: August 14, 2012
    Assignee: Kao Corporation
    Inventors: Yuichiro Seki, Nobuhiro Tatsumi, Takanobu Katayama
  • Patent number: 8227015
    Abstract: 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: Grant
    Filed: September 26, 2007
    Date of Patent: July 24, 2012
    Inventors: Keith Bruinsma, Donald L. Endres
  • Patent number: 8227632
    Abstract: A process of preparing alkyl esters of free fatty acids, including, but not limited to, biodiesel, is described herein.
    Type: Grant
    Filed: June 18, 2010
    Date of Patent: July 24, 2012
    Assignee: Philadelphia Fry-O-Diesel
    Inventors: William Wesley Berry, Brian J. Ratigan
  • Patent number: 8222439
    Abstract: 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: Grant
    Filed: July 24, 2006
    Date of Patent: July 17, 2012
    Assignee: BDI Biodiesel International AG
    Inventors: Wolfgang Glasl, Martin Mittelbach, Matthaeus Siebenhofer, Erich Jeitler, Wilhelm Hammer, Helmut Gossler, Michael Koncar
  • Patent number: 8212062
    Abstract: 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: Grant
    Filed: April 2, 2008
    Date of Patent: July 3, 2012
    Assignee: Inventure Chemical, Inc.
    Inventors: William Wes Berry, Mark G. Tegen, Stephen L. Hillis
  • Patent number: 8207362
    Abstract: A method of producing biodiesel from a source of triglycerides. The source of triglycerides is reacted with a blended alcohol composition in the presence of a catalyst to form a mixture of at least one fatty acid alcohol ester and glycerin. The fatty acid alcohol ester is then separated from the glycerin and is purified to produce a biofuel. The blended alcohol composition comprises at least one lower alcohol, a ketone and ethyl acetate. The use of the blended alcohol composition allows the transesterification process to proceed under ambient temperature and pressure conditions within a relatively short reaction time.
    Type: Grant
    Filed: November 21, 2008
    Date of Patent: June 26, 2012
    Assignee: Bio-Alternative, LLC
    Inventor: Martin Allan Morris
  • Publication number: 20120142953
    Abstract: 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: Application
    Filed: November 10, 2009
    Publication date: June 7, 2012
    Inventors: Jean-Francois Devaux, Georges Martino-Gauchi, Jean-Yves Balouin, Patrice Iafrate
  • Patent number: 8182556
    Abstract: A method for producing biofuels is provided. A method of making biofuels includes dewatering substantially intact algal cells to make an algal biomass, sequentially adding solvent sets to the algal biomass, and sequentially separating solid biomass fractions from liquid fractions to arrive at a liquid fraction comprising neutral lipids. The method also includes esterifying the neutral lipids, separating a water miscible fraction comprising glycerin from a water immiscible fraction comprising fuel esters, carotenoids, and omega-3 fatty acids. The method also includes obtaining a C16 or shorter fuel esters fraction, a C16 or longer fuel ester fraction, and a residue comprising carotenoids and omega-3 fatty acids. The method includes hydrogenating and deoxygenating at least one of (i) the C16 or shorter fuel esters to obtain a jet fuel blend stock and (ii) the C16 or longer fuel esters to obtain a diesel blend stock.
    Type: Grant
    Filed: October 7, 2011
    Date of Patent: May 22, 2012
    Assignee: Haliae Development, LLC
    Inventor: Aniket Kale
  • Patent number: 8178703
    Abstract: 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: Grant
    Filed: June 8, 2011
    Date of Patent: May 15, 2012
    Assignee: Battelle Memorial Institute
    Inventors: Herman Paul Benecke, Daniel B. Garbark, Bhima Rao Vijayendran
  • Patent number: 8163946
    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: Grant
    Filed: May 19, 2009
    Date of Patent: April 24, 2012
    Assignee: Wayne State University
    Inventors: Shuli Yan, Steven O. Salley, K. Y. Simon Ng
  • Patent number: 8152870
    Abstract: A method for producing biofuels is provided. A method of making biofuels includes dewatering substantially intact algal cells to make an algal biomass, sequentially adding solvent sets to the algal biomass, and sequentially separating solid biomass fractions from liquid fractions to arrive at a liquid fraction comprising neutral lipids. The method also includes esterifying the neutral lipids, separating a water miscible fraction comprising glycerin from a water immiscible fraction comprising fuel esters, carotenoids, and omega-3 fatty acids. The method also includes obtaining a C16 or shorter fuel esters fraction, a C16 or longer fuel ester fraction, and a residue comprising carotenoids and omega-3 fatty acids. The method includes hydrogenating and deoxygenating at least one of (i) the C16 or shorter fuel esters to obtain a jet fuel blend stock and (ii) the C16 or longer fuel esters to obtain a diesel blend stock.
    Type: Grant
    Filed: April 6, 2011
    Date of Patent: April 10, 2012
    Assignee: Heliae Development, LLC
    Inventor: Aniket Kale
  • Patent number: 8129553
    Abstract: 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: Grant
    Filed: July 2, 2007
    Date of Patent: March 6, 2012
    Assignees: Wakamatsu Corporation, Toyota Tsusyo Corporation, Toyota Chemical Engineering Co., Ltd.
    Inventors: Mikito Wakamatsu, Teruhiro Isayama, Makoto Hattori, Hiroshi Murakami, Nobuaki Hamanishi, Takeshi Sakakibara
  • Patent number: 8129324
    Abstract: 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: Grant
    Filed: October 18, 2005
    Date of Patent: March 6, 2012
    Assignee: Croda International PLC
    Inventors: Hanamanthsa S Bevinakatti, Alan G Waite
  • Patent number: 8124801
    Abstract: 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: Grant
    Filed: June 24, 2009
    Date of Patent: February 28, 2012
    Assignee: 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
  • Patent number: 8119824
    Abstract: As means for producing a biodiesel oil from a feed oil containing a free fatty acid at high efficiency, the following processes (1) to (3) are provided: (1) a process for producing a higher fatty acid ester, comprising reacting a lower alcohol with a higher fatty acid in the presence of an amorphous carbon having a sulfonate group introduced therein, thereby producing the higher fatty acid ester; (2) a process for producing a higher fatty acid ester, comprising reacting a lower alcohol with a higher fatty acid and a higher fatty acid triglyceride in the presence of an amorphous carbon having a sulfonate group introduced therein, thereby producing the higher fatty acid ester by both of the reaction between the lower alcohol and the higher fatty acid and the reaction between the lower alcohol and the higher fatty acid triglyceride; and (3) a process for producing a higher fatty acid ester, comprising: reacting a lower alcohol with a higher fatty acid and a higher fatty acid triglyceride in the presence of an am
    Type: Grant
    Filed: June 20, 2006
    Date of Patent: February 21, 2012
    Assignee: Tokyo Institute of Technology
    Inventor: Michikazu Hara
  • Patent number: 8070836
    Abstract: 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: Grant
    Filed: October 16, 2008
    Date of Patent: December 6, 2011
    Assignee: Wayne State University
    Inventors: K. Y. Simon Ng, Manhoe Kim, Steven O. Salley
  • Patent number: 8048468
    Abstract: 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: Grant
    Filed: September 5, 2007
    Date of Patent: November 1, 2011
    Assignee: Ilshin Wells Co., Ltd.
    Inventors: Dong-Hun Yoon, Kwang-Hoon Yoon, Gi-Wang Han, Moon-Won Lee, Young-Ho Lee, Sang-Hyuk Park
  • Patent number: 8039652
    Abstract: 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: Grant
    Filed: April 14, 2010
    Date of Patent: October 18, 2011
    Assignee: Carnegie Mellon University
    Inventors: Marc A. Portnoff, David A. Purta, Margaret A. Nasta, Jingfeng Zhang, Faiz Pourarian
  • Patent number: 7994354
    Abstract: 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: Grant
    Filed: April 26, 2006
    Date of Patent: August 9, 2011
    Assignee: Battelle Memorial Institute
    Inventors: Herman Paul Benecke, Daniel B. Garbark, Bhima Rao Vijayendran
  • Patent number: 7910758
    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: Grant
    Filed: December 20, 2007
    Date of Patent: March 22, 2011
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Publication number: 20110060153
    Abstract: 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: Application
    Filed: June 9, 2010
    Publication date: March 10, 2011
    Applicant: MCNEFF RESEARCH CONSULTANTS, INC.
    Inventors: Clayton V. McNeff, Larry C. McNeff, Bingwen Yan, Daniel Thomas Nowlan
  • Publication number: 20110054200
    Abstract: 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: Application
    Filed: August 31, 2010
    Publication date: March 3, 2011
    Inventors: Yang Cai, Jennifer A. Nieweg, Wayne Anthony Turner, Carla Kern Wilkinson
  • Publication number: 20110015417
    Abstract: 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: Application
    Filed: April 30, 2010
    Publication date: January 20, 2011
    Applicant: Solazyme, Inc.
    Inventors: Donald E. Trimbur, Chung-Soon Im, Harrison F. Dillon, Anthony G. Day, Scott Franklin, Anna Coragliotti
  • Patent number: 7872149
    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: Grant
    Filed: September 19, 2007
    Date of Patent: January 18, 2011
    Assignee: Best Energies, Inc.
    Inventors: Donald Leroy Bunning, Louis A. Kapicak, Thomas Arthur Maliszewski, David James Shreck
  • Patent number: 7834203
    Abstract: 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: Grant
    Filed: March 8, 2004
    Date of Patent: November 16, 2010
    Assignee: Korea Institute of Energy Research
    Inventors: Jin-Suk Lee, Deog-Keun Kim, Soon-Chul Park, Joon-Pyo Lee, Sung-Hyun Kim, Keun-Hoo Lee
  • Patent number: 7772414
    Abstract: 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: Grant
    Filed: November 13, 2007
    Date of Patent: August 10, 2010
    Assignee: Aerophase, Inc.
    Inventors: Brooks Michael Hybertson, Brian N. Hansen