Another Reactant Contains Alcoholic Or Phenolic Hydroxy (e.g., Methy Ricinoleate, Etc.) Patents (Class 554/167)
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Patent number: 8080679Abstract: Disclosed is the direct conversion process for producing biodiesel from a biomass. The direct conversion process for producing biodiesel from a biomass comprises reacting a feed stock comprising a biomass and an alkylation reagent in a substantially oxygen free environment at a temperature sufficient to hydrolyze one or more lipid glycerides in the biomass and alkylated one or more fatty acids in the reaction. The process may comprise reacting a feed stock comprising an algal biomass and tetramethylammonium hydroxide in a substantially oxygen free environment at a temperature between 250° C. and 500° C. The direct conversion process for producing biodiesel may further comprise reacting oil containing lipid glycerides with an alkylation reagent at a sufficient temperature to esterify the oil. The fatty acid alkyl esters produced from the reacted feed stock are recovered. The recovered fatty acid alkyl esters, as an essential component of biodiesel, may be formulated into biodiesel.Type: GrantFiled: December 17, 2008Date of Patent: December 20, 2011Assignee: Old Dominion University Research FoundationInventors: Patrick G. Hatcher, Zhanfei Liu
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Patent number: 8030505Abstract: A process for producing lower alkyl esters of higher fatty acids from an oil phase and lower alcohols, in a catalytic transesterification process in the presence of an alkaline catalyst. A reaction mixture is provided by mixing oil-phase fatty acids with a solution comprising methanol and an alkaline catalyst comprising sodium methylate. The transesterification reaction of the reaction mixture is accelerated by subjecting the reaction mixture to a temperature above the boiling point of methanol and pressurizing the reaction mixture sufficiently to prevent boil-off. A centrifugal separator separates glycerin phase from biodiesel phase of a resulting reaction product stream. The biodiesel phase is washed by counter-current extraction.Type: GrantFiled: December 21, 2007Date of Patent: October 4, 2011Assignee: B&P Process Equipment and Systems, LLCInventors: Abbey Martin, Joseph E. Flynn, Harold Lange
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Patent number: 8022236Abstract: A process is described for producing fatty acid alkyl esters for both diesel fuel and non-fuel uses. The feed material includes whole oleaginous seeds slurried in a liquid triglyceride oil containing at least two weight percent free fatty acid, wherein oil from inside the seeds is first extracted with concurrent esterification of free fatty acids from all sources in an acidic environment. Following sufficient free fatty acid reaction, the intermediate product is subjected to base-catalyzed concurrent extraction and transesterification. Decanting of the byproduct glycerin is followed by water washing. Subsequently, the fatty acid ester product is concurrently purified and fractionated into a biodiesel fuel stream and a non-fuel fraction, each of which undergoes post treatment as needed. The process is optionally integrated with glycerin purification and/or methanol recovery.Type: GrantFiled: October 14, 2008Date of Patent: September 20, 2011Inventor: John E. Aiken
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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: 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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Patent number: 7964639Abstract: A method of minimizing or reducing the toxicity of a retinoid having a free carboxyl group and the resulting modified retinoids are described. The method comprises the step of esterifying the carboxyl group of the retinoid with a highly sterically hindered compound, which is preferably a secondary or tertiary alcohol. The resulting retinoid esters are rendered much less toxic than the starting or parent retinoid. This process provides a retinoid ester analog of reduced toxicity so that it may be administered orally with minimal side effects and with a much greater therapeutic window. The modified retinoid compounds are useful in the treatment and prophylaxis of all diseases and disorders where retinoid compounds have been shown effective.Type: GrantFiled: January 16, 2004Date of Patent: June 21, 2011Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Margaret Clagett-Dame, Sumithra Gowlugari
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Publication number: 20110144364Abstract: The present invention relates to a method of producing alkyl esters and glycerin from a crude or semi-refined vegetable oil and an aliphatic monoalcohol, comprising a deep pretreatment purification stage to eliminate the species based on phosphorus, calcium, magnesium, zinc or iron, insoluble under the temperature conditions of the heterogeneous catalytic reactor.Type: ApplicationFiled: December 15, 2010Publication date: June 16, 2011Applicant: IFP ENERGIES NOUVELLESInventors: Aurelie DANDEU, Vincent Coupard, Laurent Bournay, Charlotte Rouquette
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Publication number: 20110105775Abstract: The present invention provides a method of converting free fatty acid (FFA) from oil to methyl ester, the method includes the steps (a) esterifying the FFA using an acidic catalyst dissolved in an alcohol, (b) separating excess alcohol, solid acid catalyst, water, glycerol, soap and other non-lipid soluble impurities from oil obtained from step (a), (c) neutralizing the oil from step (b), (d) drying the oil from step (c) and (e) transesterifying the oil from step (d) using an alkaline catalyst and an alcohol.Type: ApplicationFiled: September 29, 2010Publication date: May 5, 2011Applicant: Malaysian Palm Oil Board (MPOB)Inventors: Harrison Lau Lik Nang, Nur Sulihatimarsyila Bt. Abd. Wafti, Choo Yuen May, Mohd. Basri B. Wahid
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Patent number: 7906665Abstract: The invention provides efficient, inexpensive, and environmental friendly catalysts and catalyst systems. The catalysts can be used to catalyze esterification and/or transesterification reactions, for example, for the preparation of biodiesel. Kiln dust, such as cement kiln dust (CKD) or lime kiln dust (LKD) can be used to convert a variety of feedstock acids and/or esters to biodiesel in high yield under mild conditions. The CKD and LKD catalyst systems are recyclable esterification or transesterification catalysts that can be used to prepare biodiesel, such as methyl soyate, from various feedstocks, including vegetable oils and animal fats.Type: GrantFiled: May 16, 2008Date of Patent: March 15, 2011Assignees: Iowa State University Research Foundation, Inc., Claytec, Inc.Inventors: Victor Shang-Yi Lin, Yang Cai, Carla Kern, Joel I. Dulebohn, Jennifer A. Nieweg
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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: 20110060152Abstract: 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: ApplicationFiled: September 10, 2009Publication date: March 10, 2011Applicant: Board of Regents, The University of Texas SystemInventors: Brian H. Dennis, Richard E. Billo, Christopher R. Oliver, John W. Priest, Edward S. Kolesar, Elinor Kolesar
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Patent number: 7871448Abstract: A system and method for the conversion of free fatty acids to glycerides and the subsequent conversion of glycerides to glycerin and biodiesel includes the transesterification of a glyceride stream with an alcohol. The fatty acid alkyl esters are separated from the glycerin to produce a first liquid phase containing a fatty acid alkyl ester rich (concentrated) stream and a second liquid phase containing a glycerin rich (concentrated) stream. The fatty acid alkyl ester rich stream is then subjected to distillation, preferably reactive distillation, wherein the stream undergoes both physical separation and chemical reaction. The fatty acid alkyl ester rich stream is then purified to produce a purified biodiesel product and a glyceride rich residue stream. Biodiesel may be further recovered from the glyceride rich residue stream, by further separation of and/or processing of glycerides/free fatty acids contained therein.Type: GrantFiled: August 14, 2007Date of Patent: January 18, 2011Assignee: Seneca Landlord, LLCInventors: John P. Jackam, Joel M. Pierce, Jeffrey D. Jones, Richard H. Talley
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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: 20100311997Abstract: 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 C2H5(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: ApplicationFiled: September 5, 2008Publication date: December 9, 2010Applicant: LURGI GMBHInventors: Rudolf Boensch, Helmut Saft, Peter Mitschke, Henning Buchold
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Patent number: 7842653Abstract: The present invention provides an improved process for the preparation of lubricants from vegetable oil or fat obtained from animal source. The present invention involves a reaction of vegetable oil or fat with an alcohol in the presence of a double metal cyanide catalyst, at a temperature in the range of 150° to 200° C. for a period of 3-6 hrs to obtain the desired bio-lubricant.Type: GrantFiled: May 26, 2006Date of Patent: November 30, 2010Assignee: Council of Scientific & Industrial ResearchInventors: Srinivas Darbha, Rajendra Srivastava, Paul Ratnasamy
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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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Patent number: 7828978Abstract: Simultaneous synthesis and purification of a fatty acid monoester biodiesel fuel from a triacylglycerol feedstock is described. In an exemplary method, the triacylglycerol feedstock is continuously contacted with a catalytic chromatographic bed comprising a first (solid phase) basic catalyst through a first port of a simulated moving bed chromatographic apparatus. A monohydric alcohol and optional second (mobile phase) basic catalyst is continuously contacted with the catalytic chromatographic bed through a second port and pumped in a first direction toward the triacylglycerol feedstock to contact the triacylglycerol in a reaction zone of the catalytic chromatographic bed where the fatty acid monoester and glycerol coproduct are formed. The fatty acid monoester is removed from the reaction zone through a product port of the simulated moving bed apparatus.Type: GrantFiled: June 8, 2006Date of Patent: November 9, 2010Inventors: Doug Geier, John G. Soper
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Publication number: 20100274034Abstract: The present invention provides a method of producing a fatty acid alkyl ester and/or glycerin by bringing an oil and an alcohol into contact with each other, the method including: reacting the oil and alcohol with each other; performing solid-liquid separation for removing a solid sterol from a reaction liquid obtained in the step of reacting; and performing phase separation for separating the reaction liquid into a hydrophobic phase and a hydrophilic phase after the reaction liquid is subjected to the step of performing the solid-liquid separation, the hydrophobic phase containing the fatty acid alkyl ester, and the hydrophilic phase containing glycerin. Thereby, the present invention provides a method allowing stable continuous operation for a long time period for production of a fatty acid alkyl ester and/or glycerin.Type: ApplicationFiled: December 18, 2008Publication date: October 28, 2010Applicants: NIPPON SHOKUBAI CO., LTD, RESEARCH INSTITUTE OF INNOVATIVE TECHNOLOGY FOR THInventors: Izuho Okada, Tomoharu Oku, Hironori Horie, Masanori Nonoguchi, Atsushi Tachibana
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Process for production of fatty acid alkyl ester and production apparatus for fatty acid alkyl ester
Patent number: 7812187Abstract: An object of the present invention is to provide a method for producing an alkyl ester of a fatty acid from a fat or oil, of which main component is a triglyceride, and an alkyl alcohol under mild conditions in a high reaction efficiency, and the alkyl ester of a fatty acid can be effectively utilized as a diesel fuel oil, an industrial raw material or the like, the method further being capable of utilizing on an industrial scale, in which post-treatment steps for removing a catalyst component can be simplified or omitted. For this purpose, the method for producing an alkyl ester of a fatty acid of this invention includes the step of carrying out a transesterification reaction between a fat or oil and an alcohol in the presence of a base catalyst containing calcium oxide, characterized in that the method includes the step of contacting the base catalyst with the alcohol, to carry out an activation treatment thereof in advance of the reaction.Type: GrantFiled: January 26, 2007Date of Patent: October 12, 2010Assignees: Revo International Inc., Ehime UniversityInventors: Ayato Kawashima, Hideo Yamamoto, Tetsuya Koshikawa -
Patent number: 7806945Abstract: A system and method for converting a high free fatty acid grease feedstock to biodiesel. The process comprises a glycerolysis reaction to convert free fatty acids to glycerides and a base catalyzed transesterification reaction to produce fatty acid methyl esters and glycerin in the absence of solvents. In preferred embodiments, both glycerin and methanol are recycled. The process can process a feedstock containing up to 100 percent free fatty acid content to produce biodiesel and glycerin with minimal waste generation.Type: GrantFiled: January 26, 2004Date of Patent: October 5, 2010Assignee: Seneca Landlord, LLCInventors: John P Jackam, Joel M Pierce, Frank S Fahrenbruck
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Patent number: 7795460Abstract: Methods of making alkyl esters are described herein. The methods are capable of using raw, unprocessed, low-cost feedstocks and waste grease. Generally, the method involves converting a glyceride source to a fatty acid composition and esterifying the fatty acid composition to make alkyl esters. In an embodiment, a method of making alkyl esters comprises providing a glyceride source. The method further comprises converting the glyceride source to a fatty acid composition comprising free fatty acids and less than about 1% glyceride by mass. Moreover, the method comprises esterifying the fatty acid composition in the presence of a solid acid catalyst at a temperature ranging firm about 70° C. to about 120° C. to produce alkyl esters, such that at least 85% of the free fatty acids are converted to alkyl esters. The method also incorporates the use of packed bed reactors for glyceride conversion and/or fatty acid esterification to make alkyl esters.Type: GrantFiled: May 5, 2006Date of Patent: September 14, 2010Assignee: TDA Research, Inc.Inventor: Brian Elliott
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Patent number: 7767837Abstract: A method comprising contacting an alcohol, a feed comprising one or more glycerides and equal to or greater than 2 wt % of one or more free fatty acids, and a solid acid catalyst, a nanostructured polymer catalyst, or a sulfated zirconia catalyst in one or more reactors, and recovering from the one or more reactors an effluent comprising equal to or greater than about 75 wt % alkyl ester and equal to or less than about 5 wt % glyceride.Type: GrantFiled: May 4, 2007Date of Patent: August 3, 2010Assignee: TDA Research, Inc.Inventor: Brian Elliott
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Patent number: 7754905Abstract: A method comprising applying a controlled flow cavitation apparatus to a biodiesel production process in order to increase fatty acid alkyl ester yield. A feedstock comprising free fatty acids can be passed through a controlled flow cavitation apparatus at a velocity capable of generating a hydrodynamic cavitation zone where the free fatty acids can be esterified. One or more controlled flow cavitation apparatuses can be applied at various points of a biodiesel production process.Type: GrantFiled: July 3, 2008Date of Patent: July 13, 2010Assignee: Arisdyne Systems, Inc.Inventor: Oleg V. Kozyuk
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Patent number: 7750043Abstract: A method of minimizing or reducing the toxicity of a retinoid having a free carboxyl group and the resulting modified retinoids are described. The method comprises the step of esterifying the carboxyl group of the retinoid with a highly sterically hindered compound, which is preferably a secondary or tertiary alcohol. The resulting retinoid esters are rendered much less toxic than the starting or parent retinoid. This process provides a retinoid ester analog of reduced toxicity so that it may be administered orally with minimal side effects and with a much greater therapeutic window. The modified retinoid compounds are useful in the treatment and prophylaxis of all diseases and disorders where retinoid compounds have been shown effective.Type: GrantFiled: April 2, 2008Date of Patent: July 6, 2010Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Margaret Clagett-Dame, Sumithra Gowlugari
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Patent number: 7741502Abstract: A method of manufacturing a composition of alcohol esters of linear monocarboxylic acids with 6 to 26 carbon atoms from a vegetable or animal oil, neutral or acid, virgin or recycled, with monoalcohols having 1 to 18 carbon atoms, in the presence of a phosphate type catalyst or of an organophosphorous compound of a metal selected from the group made up of zirconium, hafnium and titanium, allows to directly produce, in one or more stages, an ester that can be used as fuel and a pure glycerin.Type: GrantFiled: April 11, 2008Date of Patent: June 22, 2010Assignee: Institut Francais du PetroleInventors: Vincent Lecocq, Sylvie Maury, Delphine Bazer-Bachi
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Publication number: 20100130763Abstract: The present invention provides processes for the formation of fatty acid alkyl esters, which may be used as biodiesel. In particular, the invention provides an esterification process in which a lipid material is contacted with an alcohol in the presence of a metal halide or metal alkoxide conjugated to a solid support. Also provided is a transesterification process in which a lipid material is contacted with an alcohol in the presence of an N-heterocyclic carbene. Also provided is a combination esterification and transesterification process in which a lipid material is contacted with a metal halide or metal alkoxide conjugated to a solid support, and then is contacted with an N-heterocyclic carbene or an alkaline catalyst.Type: ApplicationFiled: December 6, 2007Publication date: May 27, 2010Applicant: SOUTHERN ILLINOIS UNIVERSITY CARBONDALEInventor: Yong Gao
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Publication number: 20100125145Abstract: The trans-esterification system for trans-esterifying a triglyceride includes a reaction tank, a separation tank, a first pipe and a second pipe. The reaction tank is inputted with the triglyceride and a monohydric alcohol for undergoing a trans-esterification reaction to produce a mixture. The separation tank is inputted with the mixture for a phase separation to generate an ester phase solution and a glycerol phase solution having a first part and a second part. The first pipe connects the reaction tank and the separation tank, and transports the mixture from the reaction tank to the separation tank. The second pipe connects the reaction tank and the separation tank, and transports the first part of the glycerol phase solution from the separation tank to the reaction tank for undergoing the trans-esterification reaction.Type: ApplicationFiled: May 13, 2009Publication date: May 20, 2010Applicant: National Taiwan UniversityInventors: Cheng-Ching Yu, Hsiao-Ping Huang, Ming-Jer Lee, Yin-Heng Shen, Jian-Kai Cheng
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Publication number: 20100121087Abstract: A method for esterification of free fatty acids with methanol. The method has steps of: (a) contacting a heterogeneous esterification catalyst in a reactor with a reaction mixture containing: (i) methanol and (ii) a triglyceride mixture containing 70-99.8 wt % triglycerides and 0.2-30 wt % free fatty acids, under conditions suitable for esterification, to produce a product stream; (b) separating water and methanol from the product stream to produce a dried product stream; (c) contacting the dried product stream with methanol to produce a methanol-rich phase and a triglyceride-rich phase; and (d) separating the methanol-rich phase and recycling it to the reactor.Type: ApplicationFiled: May 21, 2009Publication date: May 13, 2010Inventors: Rajiv Manohar Banavali, Robert Tryon Hanlon, Alfred Karl Schultz
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Publication number: 20100105935Abstract: In a process for producing fatty acid methyl ester (FAME) from fats or oils by transesterification with methanol in the presence of an alkaline catalyst in at least two reaction stages traversed in succession, each consisting of a stirred-tank reactor and a downstream separator, a phase containing FAME and a phase containing glycerol are generated, which are separated in the separator, wherein the phase containing FAME is recirculated into the stirred-tank reactor of the next succeeding reaction stage and the phase containing glycerol is recirculated into the stirred-tank reactor of the first reaction stage, and the crude FAME withdrawn from the separator of the last reaction stage is transferred into a separator and the FAME withdrawn is dried.Type: ApplicationFiled: July 31, 2007Publication date: April 29, 2010Applicant: LURGI GMBHInventors: Helmut Saft, Klaus Hohmann, Rudolph Bönsch
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Patent number: 7705170Abstract: The present invention is directed to a method or preparing fatty acid alkyl esters from fatty acids contained in co-product streams, or waste or recycled fatty acid stock. The present method utilizes an acidic resin to convert the fatty acid stock into esters. The present method encompasses the use of reactive simulated moving bed chromatography, wherein above about 95 percent of the fatty acid stock is converted to fatty acid alkyl esters. The present method has been optimized to separate the ester product from the raffinate stream formed during the chromatographic process, thereby improving the yield of the esterification and preventing acid hydrolysis of the ester.Type: GrantFiled: April 11, 2005Date of Patent: April 27, 2010Assignee: Archer-Daniels-Midland CompanyInventors: Douglas F. Geier, Ahmad K. Hilaly, John G. Soper
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Patent number: 7652156Abstract: A method allowing, from natural fat or oils, vegetable or animal, or from other glyceride mixtures, to obtain in a quasi-quantitative way fatty acid ethyl esters that can be used as gas oil substitutes, comprises the succession of stages as follows: a stage (a) wherein the oil, the fat or the glyceride mixture is transesterified by ethanol using a soluble catalyst or a catalyst that becomes soluble during the reaction, a stage (b) wherein the glycerin formed is decanted and removed, without requiring an excess ethanol evaporation operation, a stage (c) wherein a second transesterification reaction is carried out so as to obtain a product whose ester content is at least 97% by mass, a stage (d) wherein controlled neutralization of the catalyst is carried out, a stage (e) wherein the excess ethanol is removed by distillation, a stage (f) wherein the ester undergoes purification by means of water wash sequences, and a stage (g) wherein the ester mixture is dried under reduced pressure.Type: GrantFiled: September 20, 2006Date of Patent: January 26, 2010Assignee: Institut Francais du PetroleInventors: Gérard Hillion, Bruno Delfort
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Patent number: 7622600Abstract: A continuous biofuel production process includes the steps of introducing a feedstock containing fatty acids and triglycerides into a first reaction vessel, in which alkyl esters are produced through esterification of free fatty acids. The alkyl esters and triglycerides are introduced into a second reaction vessel, in which at least a portion of the triglycerides are converted to alkyl esters and glycerin through transesterification. The alkyl esters, glycerin, and remaining triglycerides are introduced into a third reaction vessel, in which at least a portion of the remaining triglycerides are converted to alkyl esters and glycerin through transesterification.Type: GrantFiled: January 5, 2007Date of Patent: November 24, 2009Assignee: Redland Industries, Inc.Inventor: Wesley Drew Marr
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Patent number: 7566794Abstract: A method allowing, from natural fat or oils, or from other glyceride mixtures, to obtain fatty acid ethyl esters that can be used as gas oil substitutes, comprises: stage (a) oil, fat or a glyceride mixture is transesterified by ethanol using a soluble catalyst or a catalyst that becomes soluble during the reaction; stage (b) resultant glycerin is decanted and removed, without requiring an excess ethanol evaporation operation, stage (c) a second transesterification is conducted to obtain a product whose ester content is at least 97% by mass, stage (d) evaporation of excess ethanol is carried out in the presence of the catalyst under suitable conditions preventing a reverse transesterification reaction, the resultant ethanol being practically anhydrous, stage (e) the ester undergoes purification by water wash sequences, and stage (f) the ester is dried under reduced pressure.Type: GrantFiled: September 20, 2006Date of Patent: July 28, 2009Assignee: Institut Francais du PetroleInventors: Gérard Hillion, Bruno Delfort
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Patent number: 7563915Abstract: Methods for improved manufacture of green biodiesel focus on the selection and use of one or more solid metallic oxide base catalyst(s) selected from the group consisting of calcium oxide (CaO), calcium aluminum oxide (CaO—Al2O3), calcium titanate (CaTiO3), barium titanate (BaTiO3), magnesium aluminum oxide (MgO—Al2O3), zinc oxide (ZnO), copper (II) oxide (CuO), nickel oxide (NiO), manganese oxide (MnO), titanium oxide (TiO), vanadium oxide (VO), cobalt oxide (CoO), iron oxide (FeO), chromite (FeCr2O4), hydrotalcite (Mg6Al2(CO3)(OH)16.4(H2O), magnetite (Fe3O4), magnesium silicate and calcium silicate.Type: GrantFiled: May 29, 2007Date of Patent: July 21, 2009Assignee: The Penn State Research FoundationInventors: Jack Vincent Matson, Dheeban Chakravarthi Kannan
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Patent number: 7557228Abstract: Wax esters are prepared by reacting a solution of palm oil in an organic solvent with oleyl alcohol in the presence of an immobilized lipase wherein molar ratio of palm oil to oleyl alcohol is between 1:2 and 1:4. Immobilized lipase used is present in an amount which is equivalent to not less than 1000 ?g of protein per milli-mole of palm oil used and the reaction is carried out at 40° C. to 50° C. for a period of not less than 5 hours. The organic solvent used has a value of log P not less than 3.5.Type: GrantFiled: December 30, 2004Date of Patent: July 7, 2009Assignee: Universiti Putra MalaysiaInventors: Mahiran Basri, Mohd. Basyaruddin Abd. Rahman, Abu Bakar Salleh, Raja Noor Zaliha Abd. Rahman
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Patent number: 7553982Abstract: A method of producing biodiesel from a source of triglycerides. The source of triglycerides is reacted with a blended alcohol composition in the presence of a catalyst to form a mixture of at least one fatty acid alcohol ester and glycerin. The fatty acid alcohol ester is then separated from the glycerin and is purified to produce a biofuel. The blended alcohol composition comprises at least one lower alcohol, a ketone and ethyl acetate. The use of the blended alcohol composition allows the esterfication process to proceed under ambient temperature and pressure conditions within a relatively short reaction time.Type: GrantFiled: August 13, 2007Date of Patent: June 30, 2009Assignee: Bio-Alternative, LLCInventor: Martin Allan Morris
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PROCESS FOR PRODUCING BIODIESEL WITH IMPROVED FILTRATION CHARACTERISTICS AND BIODIESEL THUS PRODUCED
Publication number: 20090158640Abstract: A process for the production and purification of fatty acid esters of lower alkyl alcohols with improved filtration characteristics comprising the steps of: a) transesterifying a mixture of fatty acid esters of glycerol with a lower alkyl alcohol while using an alkaline catalyst; b) separating the reaction mixture resulting from step (a) into a glycerol phase and a fatty acid lower alkyl ester phase; c) inactivating the catalytic intermediates present in said fatty acid lower alkyl ester phase; d) removing the lower alkyl alcohol from the mixture resulting from step (c) by evaporation at reduced pressure to a value of less than 2% by weight; e) treating the evaporation residue resulting from step (d) with water; and f) isolating the fatty acid esters of lower alcohols by drying the product resulting from step (e); and biodiesel containing FAME produced according to this process.Type: ApplicationFiled: December 23, 2008Publication date: June 25, 2009Applicant: N.V. Desmet Ballestra Engineering S.A.Inventors: Marc Kellens, Francesco Soragna, Wim De Greyt -
Publication number: 20090163731Abstract: A process for producing lower alkyl esters of higher fatty acids from an oil phase and lower alcohols, in a catalytic transesterification process in the presence of an alkaline catalyst. A reaction mixture is provided by mixing oil-phase fatty acids with a solution comprising methanol and an alkaline catalyst comprising sodium methylate. The transesterification reaction of the reaction mixture is accelerated by subjecting the reaction mixture to a temperature above the boiling point of methanol and pressurizing the reaction mixture sufficiently to prevent boil-off. A centrifugal separator separates glycerin phase from biodiesel phase of a resulting reaction product stream. The biodiesel phase is washed by counter-current extraction.Type: ApplicationFiled: December 21, 2007Publication date: June 25, 2009Applicant: B&P Process Equipment and Systems, LLCInventors: Abbey Martin, Joseph E. Flynn, Harold Lange
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Patent number: 7541480Abstract: The present invention relates to a process for the preparation of a composition comprising unsaturated compounds, in particular polyunsaturated compounds, which comprises concentrating and purifying the compounds by contact with silicon and/or aluminum derivatives. The process of the invention represents an advantageous substitute of the usual distillation processes, coupled or not to chromatographic processes, and allows to isolate and remove polar byproducts.Type: GrantFiled: November 18, 2004Date of Patent: June 2, 2009Assignee: Pro Aparts-Investimentos E Consultoria LDAInventor: Tiberio Bruzzese
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Patent number: 7540889Abstract: The process for preparing a refinery feedstock from black liquor soap comprising adding excess alcohol (preferably methanol) to black liquor soap. Acid is then added to the mixture to drop the pH of the mixture to approximately 2 to convert carboxylate salt of fatty and resin acids to the free fatty and resin acids. In the reaction process, the free fatty and resin acids react with the alcohol, with the aid of the acid catalyst, to yield the desired ester products. The resulting feedstock can be distilled or refined to yield sterols and related alcohols, biodiesel and other fuels.Type: GrantFiled: July 11, 2006Date of Patent: June 2, 2009Assignee: Bluekey Energy Inc.Inventors: Mark James Logan, Phillip Richard Pearce, David George Dick
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Publication number: 20090112007Abstract: The invention provides efficient, inexpensive, and environmental friendly catalysts and catalyst systems. The catalysts can be used to catalyze esterification and/or transesterification reactions, for example, for the preparation of biodiesel. Kiln dust, such as cement kiln dust (CKD) or lime kiln dust (LKD) can be used to convert a variety of feedstock acids and/or esters to biodiesel in high yield under mild conditions. The CKD and LKD catalyst systems are recyclable esterification or transesterification catalysts that can be used to prepare biodiesel, such as methyl soyate, from various feedstocks, including vegetable oils and animal fats.Type: ApplicationFiled: May 16, 2008Publication date: April 30, 2009Inventors: Victor Shang-Yi Lin, Yang Cai, Carla Kern, Joel I. Dulebohn, Jennifer A. Nieweg
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Publication number: 20090099380Abstract: A process is described for producing fatty acid alkyl esters for both diesel fuel and non-fuel uses. The feed material includes whole oleaginous seeds slurried in a liquid triglyceride oil containing at least two weight percent free fatty acid, wherein oil from inside the seeds is first extracted with concurrent esterification of free fatty acids from all sources in an acidic environment. Following sufficient free fatty acid reaction, the intermediate product is subjected to base-catalyzed concurrent extraction and transesterification. Decanting of the byproduct glycerin is followed by water washing. Subsequently, the fatty acid ester product is concurrently purified and fractionated into a biodiesel fuel stream and a non-fuel fraction, each of which undergoes post treatment as needed. The process is optionally integrated with glycerin purification and/or methanol recovery.Type: ApplicationFiled: October 14, 2008Publication date: April 16, 2009Inventor: John E. Aiken
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Patent number: 7507846Abstract: Method and apparatus for producing biodiesel fuel, i.e., alkyl ester, from vegetable and/or animal oil. A transesterification catalyst is prepared in a base catalyst tank by spraying alkyl alcohol under pressure through jets at metal hydroxide pellets until the pellets have fully reacted with the alcohol. The oil is heated and transesterified in the presence of alkyl alcohol and the transesterification catalyst in a closed, recirculating transesterification flow system under slight cavitation to yield product alkyl ester and product glycerol. Cavitation is achieved by permitting air to enter the transesterification flow system through an adjustable air inlet valve. When permitted to stand, product alkyl ester forms an upper layer that is decanted and subjected to purification steps, to remove particulates and alkyl alcohol from the product alkyl ester, and a lower layer of product glycerol is drained away.Type: GrantFiled: March 17, 2004Date of Patent: March 24, 2009Inventor: Michael F. Pelly
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Patent number: 7482480Abstract: The present invention provides a process for the preparation of hydrocarbon fuels, which comprises contacting fatty acid glycerides with alcohols in the presence of a solid, double metal cyanide catalyst at a temperature in the range of 150° to 200° C. for a period of 2-6 hrs and separating the catalyst from the above said reaction mixture to obtain the desired hydrocarbon fuel.Type: GrantFiled: March 30, 2006Date of Patent: January 27, 2009Assignee: Council of Scientific & Industrial ResearchInventors: Darbha Srinivas, Rajendra Srivastava, Paul Ratnasamy
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Publication number: 20090023808Abstract: The present invention includes methods for producing and purifying esters of polyunsaturated fatty acids that include reacting a composition having triglycerides with polyunsaturated fatty acid residues in the presence of an alcohol and a base to produce an ester of a polyunsaturated fatty acid from the triglycerides. The composition can be a polyunsaturated fatty acid-containing composition that has not been conventionally processed. The reacted composition can be further processed by distillation.Type: ApplicationFiled: June 27, 2008Publication date: January 22, 2009Applicant: MARTEK BIOSCIENCES CORPORATIONInventors: Krishna Raman, Jung Lee, Neil Leininger, Chris Luigart
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Publication number: 20090005582Abstract: Vessels and methods for esterification and transesterification of fatty acids under near critical or supercritical reaction conditions are disclosed herein. Alkyl esters produced in the vessel with the disclosed methods are used to create biofuel, such as biodiesel.Type: ApplicationFiled: June 20, 2008Publication date: January 1, 2009Inventor: Greg Anderson
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Patent number: 7468450Abstract: The invention relates to a process for the preparation of fatty acid esters from fats and oils of biological origin by transesterification with monohydric alcohols in the presence of basic catalysts, the catalysts being salts of a basic organic compound and carbonic acid.Type: GrantFiled: March 22, 2005Date of Patent: December 23, 2008Inventors: Siegfried Peter, Eckhard Weidner
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Patent number: 7456305Abstract: The present invention is directed to a method of producing fuel from vegetable or animal fat having a free fatty acid content by means of catalytic esterification reactions. The method includes esterification of free fatty acids at a higher temperature in a vacuum with one or more multivalent alcohols accompanied by solid neutral catalysts, which are present in a packing bed inside a reactor, whereby the fat travels from top to bottom in the reactor with the alcohol(s) running counter current and a mixture containing alcohol and water being removed from an upper part of the reactor by means of a vacuum effect. The present invention is also directed to the apparatus for implementing the methods disclosed.Type: GrantFiled: March 23, 2007Date of Patent: November 25, 2008Assignee: GMK-Gesellschaft fur Motoren und Kraftanlagen mbHInventors: Aldo Piacentini, Rene Niesner