Another Reactant Contains Alcoholic Or Phenolic Hydroxy Patents (Class 554/170)
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Publication number: 20120289727Abstract: The present invention refers to a process for modifying epoxidized or non-modified vegetable oils. More specifically, it refers to the process through which vegetable oils and alcohols are converted into fatty acid alkyl esters through transesterification. The present invention also refers to the products obtained through the process disclosed herein.Type: ApplicationFiled: December 17, 2009Publication date: November 15, 2012Inventors: Milton Sobrosa Cordeiro, Sérgio Teixeira, Ariovaldo Fernandes Junior
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Publication number: 20120288906Abstract: Described is a process for obtaining fatty acid C1-C4 alkyl esters from unrefined fats and oils, wherein: (a) unrefined fats or oils having an acid value of from 1 to 20 are treated with hot steam in a counter-current column to provide a first fraction of free fatty acids and low boiling impurities and a second fraction of de-acidified and de-watered fats or oils; (b) said first fraction is subjected to esterification with lower C1-C4 alcohols to provide a third fraction of fatty acid C1-C4 alkyl esters; (c) said second and said third fraction are combined and subjected to a low pressure transesterification to provide an intermediate fraction of fatty acid C1-C4 alkyl esters, C1-C4 alcohols and glycerol; and (d) said intermediate is subjected to a separation process to remove C1-C4 alcohols and the glycerol to provide a second fraction of C1-C4 alkyl esters.Type: ApplicationFiled: May 12, 2012Publication date: November 15, 2012Applicant: Cognis IP Management GmbHInventors: Horst Josten, Ewelina Sobierska, Adrian Chan, Truc Tran Anh
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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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Publication number: 20120264957Abstract: A method for isolating chlorophylls from intact algal cells is provided. The method includes dewatering intact algal cells from an algal cell culture to make an algal biomass, extracting lipids along with carotenoids and chlorophylls from the algal biomass, and separation of the chlorophylls using adsorption or membrane diafiltration or other methods. The method can include selective extraction of other algal components including polar lipids, neutral lipids, proteins, and carbohydrates. The method may include esterifying the lipids with a catalyst in the presence of an alcohol, and separating a water soluble fraction comprising glycerin from a water insoluble fraction comprising fuel esters and distilling the fuel esters under vacuum to obtain a C16 or shorter fuel esters fraction, a C16 or longer fuel ester fraction, and a residue comprising omega-3 fatty acids esters and remaining carotenoids.Type: ApplicationFiled: June 22, 2012Publication date: October 18, 2012Applicant: HELIAE DEVELOPMENT, LLCInventor: Aniket KALE
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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: 8269028Abstract: 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: February 23, 2011Date of Patent: September 18, 2012Inventor: Michael F. Pelly
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Publication number: 20120219709Abstract: Disclosed is a method of using at least one functionalized hydroxycarboxylic acid oligomer as an adhesive for bonding materials. Also described is a process for manufacturing functionalized hydroxycarboxylic acid oligomers including at least one stage for polycondensation of a hydroxycarboxylic acid and a functional agent, as well as functionalized hydroxycarboxylic acid oligomers that can be obtained and the adhesive compositions that include them.Type: ApplicationFiled: October 27, 2010Publication date: August 30, 2012Applicant: VALAGRO CARBONE RENOUVELABLE POITOU-CHARENTESInventors: Antoine Piccirilli, Cedric Dever
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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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Publication number: 20120209014Abstract: A fiber reaction process whereby reactive components contained in immiscible streams are brought into contact to effect chemical reactions and separations. The conduit reactor utilized contains wettable fibers onto which one stream is substantially constrained and a second stream is flowed over to continuously create a new interface there between to efficiently bring about contact of the reactive species and thus promote reactions thereof or extractions thereby. Co-solvents and phase transfer catalysts may be employed to facilitate the process.Type: ApplicationFiled: March 2, 2012Publication date: August 16, 2012Applicant: CHEMTOR, LPInventor: John Lee Massingill
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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: 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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Publication number: 20120136168Abstract: Prepare an ester of a secondary hydroxy fatty acid oligomer by first partially homopolymerizing a hydroxylated fatty acid compound, reacting the partially homopolymerized hydroxylated fatty acid compound with an alcohol to form an intermediate product, and capping the intermediate product with an acid, acid anhydride or ester. The ester of a secondary hydroxy fatty acid oligomer may be represented as follows: (3) where R is an alkyl group that contains from six to twelve carbon atoms, R1 is hydrogen or a methyl radical, x is an integer within a range of from 8 to 12, n is an integer between 1 and 20, R2 is an alkyl group that contains from one carbon atom to twenty carbon atoms and R3 is an alkyl group that contains from one carbon atom to twelve carbon atoms.Type: ApplicationFiled: July 1, 2010Publication date: May 31, 2012Inventors: Jochem Kersbulck, Daniele Vinci, Johan A. Thoen
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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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Publication number: 20120065416Abstract: The present invention relates to methods useful for converting microbial lipids from an oleaginous microbial biomass into fatty acid alcohol esters, without prior extraction of the lipids from the biomass. The present invention also relates to fatty acid alcohol esters produced by the methods described herein. The fatty acid alcohol esters produced by the methods described herein may be useful as biodiesel, or a component thereof. In embodiments, the converting of microbial lipids to fatty acid alcohol esters may be accomplished by contacting an acid catalyst, an alcohol and an oleaginous microbial biomass containing microbial lipids under sufficient conditions and for a sufficient period of time for in situ transesterification reaction of at least some microbial lipids to their corresponding fatty acid alcohol ester.Type: ApplicationFiled: September 15, 2011Publication date: March 15, 2012Applicant: Utah State UniversityInventors: Lance Seefeldt, Bradley Wahlen, Robert Willis, Alexander McCurdy
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Publication number: 20120055079Abstract: A method of making biofuels and valuable food and neutraceutical products includes dewatering intact algal cells to make an algal biomass, extracting neutral lipids along with carotenoids and chlorophylls from the algal biomass, and separating the carotenoids and chlorophylls. The remaining neutral lipids are esterified with a catalyst in the presence of an alcohol. The method also includes separating a water soluble fraction comprising glycerin from a water insoluble fraction comprising fuel esters and distilling the fuel esters under vacuum to obtain a C16 or shorter fuel esters fraction, a C16 or longer fuel ester fraction, and a residue comprising omega-3 fatty acids esters and remaining carotenoids. The method further 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: ApplicationFiled: October 14, 2011Publication date: March 8, 2012Inventor: Aniket KALE
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Patent number: 8128825Abstract: A fiber reaction process whereby reactive components contained in immiscible streams are brought into contact to effect chemical reactions and separations. The conduit reactor utilized contains wettable fibers onto which one stream is substantially constrained and a second stream is flowed over to continuously create a new interface there between to efficiently bring about contact of the reactive species and thus promote reactions thereof or extractions thereby. Co-solvents and phase transfer catalysts may be employed to facilitate the process.Type: GrantFiled: October 9, 2009Date of Patent: March 6, 2012Assignee: Chemtor, LPInventor: John Lee Massingill
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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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Publication number: 20110313181Abstract: Various embodiments of the present invention are directed to processes and methods for converting lipids comprising fatty acids into fatty esters. According to various embodiments of the invention, the saponifiable lipids are reacted with a base to form alkali soaps. The alkali soaps are then reacted with an acid to form fatty esters. Both the base reaction and the acid reaction may occur in the presence of one or more alcohols. Following the acid reaction, a solvent may be added to effect a separation of the fatty esters, which may then be recovered.Type: ApplicationFiled: April 1, 2011Publication date: December 22, 2011Inventors: Andy Thompson, Jeffrey Hippler, Lea Dulatas, Louis A. Kapicak
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Publication number: 20110313090Abstract: An improved method for producing di-isotridecylphthalate (DTDP) is disclosed by esterification using a tetra-alkyl titanate catalyst made from preferably primary alcohols having at least 4 and preferably up to but not more than 10 carbon atoms. In the esterification process, compared to using tetra-isopropyl titanate catalyst, less of the alcohol from the catalyst contributes to the environmental burden associated with discarding the waste water byproduct, and more is incorporated into the prime DTDP product.Type: ApplicationFiled: November 16, 2009Publication date: December 22, 2011Inventors: Nicolaas A. De Munck, Raphael F. Caers, Didier Naert
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Patent number: 8071799Abstract: 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: January 29, 2009Date of Patent: December 6, 2011Assignee: Energy & Environmental Research Center FoundationInventor: Edwin S. Olson
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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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Publication number: 20110269982Abstract: Methods to convert fatty acids to highly functionalized esters, ester polyols, amides, and amide polyols. The products can be used to make polyurethane and polyester films and foams.Type: ApplicationFiled: December 31, 2009Publication date: November 3, 2011Applicant: Battelle Memorial InstituteInventors: Herman Paul Benecke, Daniel B. Garbark, Bhima Rao Vijayendran
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Publication number: 20110269980Abstract: A process results in oligomerized ester alkoxylate compositions having substantially no unsaturation, which may be useful as lubricants, heat transfer fluids, plasticizers, thickening agents, surfactants, or power transmission fluids. The steps include, in either order, oligomerization of a hydroxylated fatty acid or fatty ester and quantitative reaction of unreacted carboxylic acid or ester groups with an alcohol, with the product of either reaction then being alkoxylated in the presence of a double metal cyanide catalyst. These oligomerized ester alkoxylates may be derived from vegetable oils to ensure high levels of renewable carbons. The compositions may exhibit desirably high viscosity index, low pour point, and high levels of renewable carbons.Type: ApplicationFiled: April 7, 2011Publication date: November 3, 2011Inventors: Daniele Vinci, Jochem Kersbulck
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Publication number: 20110269981Abstract: Methods to pre-esterify primary polyols used in converting biobased oils, oil derivatives, and modified oils to highly functionalized esters, ester polyols, amides, and amide polyols.Type: ApplicationFiled: December 31, 2009Publication date: November 3, 2011Applicant: BATTELLE MEMORIAL INSTITUTEInventors: Herman Paul Benecke, Daniel B. Garbark, Bhima Rao Vijayendran
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Publication number: 20110224451Abstract: The invention relates to a process for producing alkyl esters, the process comprising reacting a feedstock that includes one or more fatty acid glycerol esters or one or more fatty acid or mixture thereof with a C1 to C4 alcohol in the presence of a catalyst at a temperature substantially 100° C. or more, the catalyst including a catalyst composition comprising oxides, mixed oxides, silicates or sulphates of two or more of silica, aluminium, iron, calcium, magnesium, sodium and potassium.Type: ApplicationFiled: June 11, 2008Publication date: September 15, 2011Inventors: Rajiv Kumar Chaturvedi, Nawalkishor Mal, Kyatanahalli Srinivasa Nagabhushana, Debabrata Rautaray, Tushar R. Shinde
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Publication number: 20110195471Abstract: 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: ApplicationFiled: February 10, 2011Publication date: August 11, 2011Applicant: Inventure Chemical, Inc.Inventors: William Wes Berry, Mark G. Tegen, Stephen L. Hillis
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Publication number: 20110189745Abstract: 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 phospholipids, free fatty acids (FFA), glycerides, or combination thereof as well as polysaccharides, cellulose, hemicellulose, lignocellulose, protein polymers, or combination thereof in the presence of an alcohol and an optional acid catalyst.Type: ApplicationFiled: February 1, 2011Publication date: August 4, 2011Applicant: Inventure Chemical, Inc.Inventors: William W. Berry, Mark G. Tegen, William R. Sutterlin
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Publication number: 20110185625Abstract: Solid mixed catalysts and methods for use in conversion of triglycerides and free fatty acids to biodiesel are described. A batch or continuous process may be used with the catalysts for transesterification of triglycerides with an alkyl alcohol to produce corresponding mono carboxylic acid esters and glycerol in high yields and purity. Similarly, alkyl and aryl carboxylic acids and free fatty acids are also converted to corresponding alkyl esters. The described catalysts are thermostable, long lasting, and highly active.Type: ApplicationFiled: August 20, 2009Publication date: August 4, 2011Applicant: SBI Fine Chemicals Inc.Inventors: Inder Pal Singh, Shradha Singh, Ritesh Patel, Bharat Mistry, Manish Mehta, Peter Omolo Otieno
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Publication number: 20110151524Abstract: A method for producing fatty acid alkyl esters from biolipids through transesterification and/or esterification reactions uses a flow-through cavitation device for generating cavitation bubbles in a fluidic reaction medium. The fluidic medium is passed through sequential compartments in the cavitation device having varying diameters and inner surface features to create localized reductions in fluid pressure thus vaporizing volatile alcohols and creating an increased surface area and optimized conditions for the reaction to occur at the gas-liquid interface around the bubbles.Type: ApplicationFiled: June 22, 2010Publication date: June 23, 2011Applicant: CAVITATION TECHNOLOGIES, INC.Inventors: Roman Gordon, Igor Gorodnitsky, Varvara Grichko
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Publication number: 20110151527Abstract: 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 phospholipids, free fatty acids (FFA), glycerides, or combination thereof as well as polysaccharides, cellulose, hemicellulose, lignocellulose, protein polymers, or combination thereof in the presence of an alcohol and an optional acid catalyst.Type: ApplicationFiled: January 26, 2011Publication date: June 23, 2011Applicant: Inventure Chemical, Inc.Inventors: William W. Berry, Mark G. Tegen, William R. Sutterlin
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Publication number: 20110113677Abstract: Methods and apparatus for the production of biodiesel and esters are provided. The methods can include converting a fatty acid rich material to biodiesel using a homogeneous catalyst, and electrodialysis to remove or concentrate the catalyst.Type: ApplicationFiled: January 25, 2011Publication date: May 19, 2011Applicant: PRIMAFUEL, INC.Inventor: Richard R. Woods
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Patent number: 7935840Abstract: An apparatus and method for the continuous production of biofuel by the transesterification of a triglyceride. The apparatus comprises a high shear homogenizer; a reaction chamber; a gravity driven separation device; an evacuated packed thin film stripper; a counter current pack water contactor; and, an evacuated packed spray drier, wherein each component operates with minimal heat and mass transfer resulting in a high capacity process with a reduced footprint.Type: GrantFiled: February 20, 2007Date of Patent: May 3, 2011Assignee: Nextgen Fuel, Inc.Inventors: Philip D. Leveson, John Paul Gaus
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Publication number: 20110065943Abstract: A method for the selective esterification of free fatty acids, alone or in triglycerides, with C1-C8 aliphatic alcohols or diols. The method uses a selective heterogeneous esterification catalyst. The catalyst is contacted with a reaction mixture containing a triglyceride having at least 0.5% free fatty acids, or a reaction mixture containing only free fatty acids, and a C1-C8 aliphatic alcohol or diol under conditions suitable for esterification.Type: ApplicationFiled: September 16, 2009Publication date: March 17, 2011Inventors: Rajiv Manohar Banavali, Alfred Karl Schultz
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Patent number: 7906082Abstract: 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 23, 2009Date of Patent: March 15, 2011Inventor: Michael F. Pelly
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Publication number: 20110054201Abstract: A process for producing fatty acid esters with a high yield from an unrefined natural oil or fat, such as waste oil discarded by restaurant, food industries or common homes. The process comprises reacting an oil or fat with an alcohol in the presence of a titanate catalyst of general formula: Ti(OR)4 in which R means: methyl, ethyl, isopropyl, n-buthyl, 2-ethylhexyl or octoleneglycole rest.Type: ApplicationFiled: August 24, 2007Publication date: March 3, 2011Inventors: Josip Kuftinec, Nikola Blazevic, Marijan Hohnjec, Kata Blazevic
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Patent number: 7897798Abstract: The present invention relates to methods and apparatus for producing alkyl esters from lipid feed stocks, such as plant oils and/or animal fats, and systems including the same. In an embodiment, the invention includes a process for producing alkyl esters including mixing a lipid feed stock with an alcohol to form a reaction mixture; and contacting the reaction mixture with a catalyst under supercritical conditions for the alcohol, the catalyst comprising an unmodified metal oxide selected from the group consisting of alumina, titania, zirconia, and hafnia, and removing residual free fatty acids from the reaction mixture. Other embodiments are included herein.Type: GrantFiled: August 3, 2007Date of Patent: March 1, 2011Assignee: McNeff Research Consultants, Inc.Inventors: Clayton V. McNeff, Larry C. McNeff, Arlin E. Gyberg, Bingwen Yan, Daniel Thomas Nowlan, Brian Krohn
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Patent number: 7851643Abstract: A method of manufacturing an ester composition comprising ethyl esters of linear monocarboxylic acids having 6 to 26 carbon atoms from a vegetable or an animal oil, neutral or acid, virgin or recycled, the method comprising: a stage 1 of reaction of vegetable or animal oil with methanol, in the presence of a heterogeneous catalyst comprising a combination of at least one metallic oxide and alumina or a combination of at least two metallic oxides and possibly alumina, and a stage 2 of reaction of the product from stage 1 with ethanol in the presence of a heterogeneous catalyst as defined for stage 1, so as to obtain from vegetable or animal oils, a mixture of fatty acid esters rich in fatty acid ethyl esters and a glycerin of high purity.Type: GrantFiled: September 15, 2006Date of Patent: December 14, 2010Assignee: IFP Energies NouvellesInventors: Gérard Hillion, Bruno Delfort
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Publication number: 20100305346Abstract: The present invention provides a method for producing a fatty acid monoester product by reacting an animal oil and/or a vegetable oil with an alcohol in the presence of a sulfonic acid group-introduced amorphous carbon catalyst and water. By this method, the production of a fatty acid monoglyceride, which is difficult to separate from the fatty acid monoester, can be suppressed, and the fatty acid monoester can be efficiently produced. Also, the present invention provides a method for producing a fatty acid monoester product by performing the transesterification reaction of an animal oil and/or a vegetable oil with an alcohol, or the esterification reaction of a fatty acid with an alcohol, in the presence of a sulfonic acid group-introduced amorphous carbon catalyst washed with water. By this method, the life of the catalyst can be extended, and the production cost can be reduced.Type: ApplicationFiled: October 27, 2008Publication date: December 2, 2010Applicants: Tokyo Institute of Technology, ASAHI KASEI KABUSHIKI KAISHAInventors: Michikazu Hara, Kunihiko Yamashita
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Publication number: 20100298586Abstract: Multistage process for the preparation of fatty acid alkyl esters.Type: ApplicationFiled: December 16, 2008Publication date: November 25, 2010Applicant: BAYER TECHNOLOGY SERVICES GMBHInventors: Wulf Dietrich, Stefan Grasser, Dieter Heinz, Jürgen Karthaus, Leslaw Mleczko, Heinrich Morhenn, Rafael Watsitz, Ren Wu
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Publication number: 20100298432Abstract: The invention relates to the use of esters of 2-butyloctanol with C2-36 carboxylic acids or C2-36 dicarboxylic acids in cosmetic and/or pharmaceutical preparations. The compounds are characterised by a particularly light feeling.Type: ApplicationFiled: August 9, 2007Publication date: November 25, 2010Applicant: Cognis IP Management GmbHInventors: Achim Ansmann, Markus Dierker, Catherine Weichold
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Publication number: 20100292328Abstract: The invention relates to the use of esters of 2-ethylbutanol with C4-36 carboxylic acids or C4-36 dicarboxylic acids in cosmetics and/or pharmaceutical preparations. The compounds are characterised by a particularly light feeling.Type: ApplicationFiled: August 9, 2007Publication date: November 18, 2010Applicant: Cognis IP Management GmbHInventors: Stefanie Althaus, Markus Dierker, Daniela Prinz, Catherine Weichold
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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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Publication number: 20100240616Abstract: Omega-3 lipid compounds of the general formula (I): wherein R1 and R2 are the same or different and are chosen from a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; P represents a hydrogen atom, (Formula II) wherein P2, P3, and P4 are chosen from a hydrogen atom, an alkyl group, and a C14-C22 alkenyl group, wherein the alkyl and alkenyl groups are optionally substituted with a hydroxy group, (Formula III), (Formula IV), or (Formula V); and Y is a C14-C22 alkenyl group with at least one double bond, having E and/or Z configuration; or any pharmaceutically acceptable complex, solvate, salt or pro-drug thereof, with the proviso that R1 and R2 are not simultaneously a hydrogen atom.Type: ApplicationFiled: November 1, 2007Publication date: September 23, 2010Inventors: Anne Kristin Holmeide, Jenny Rosman
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Publication number: 20100212220Abstract: Improvements to biodiesel compositions, and methods for making those compositions more efficiently, are provided. Some variations of this invention provide processes for producing biodiesel and at least one C1-C4 alcohol, such as ethanol. Other variations provide certain biodiesel compositions containing C2+ alkyl esters. In some embodiments, biodiesel compositions are produced entirely from renewable resources.Type: ApplicationFiled: February 17, 2010Publication date: August 26, 2010Applicant: Range Fuels, Inc.Inventor: Shakeel H. TIRMIZI
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Publication number: 20100209462Abstract: The invention relates to esters of 2-propylheptanoic acid and also to the use of esters of 2-propylheptanoic acid in cosmetic and/or pharmaceutical preparations. The compounds are characterized by the particularly lightweight sensation thereof.Type: ApplicationFiled: April 26, 2008Publication date: August 19, 2010Applicant: COGNIS IP MANAGEMENT GMBHInventor: Markus Dierker
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Publication number: 20100196971Abstract: The invention provides novel mesoporous particles and methods for the selective sequestration of organic compounds from microorganisms, such as from various genera and species of algae that produce important organic compounds. The organic compounds can be selectively sequestered, for example, in favor of biodiesel impurities such as sterols and chlorophyll, to provide substantially pure free fatty acids. The free fatty acids can then be esterified to provide pure biodiesel.Type: ApplicationFiled: February 2, 2010Publication date: August 5, 2010Applicant: Iowa State University Research Foundation, Inc.Inventors: Victor Shang-Yi Lin, Brian G. Trewyn, Po-Wen Chung, Igor Ivan Slowing
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Publication number: 20100191008Abstract: 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: ApplicationFiled: January 29, 2009Publication date: July 29, 2010Applicant: ENERGY & ENVIRONMENTAL RESEARCH CENTER FOUNDATIONInventor: Edwin S. Olson
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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
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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