Another Reactant Contains Alcoholic Or Phenolic Hydroxy (e.g., Methy Ricinoleate, Etc.) Patents (Class 554/167)
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Patent number: 8686170Abstract: A method of preparing 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 catalyst of nitrogen-containing metallophosphate type.Type: GrantFiled: June 1, 2011Date of Patent: April 1, 2014Assignee: IFP Energies NouvellesInventors: Delphine Bazer-Bachi, Francois Chevire, Vincent Lecocq, Erwan Ray, Pascal Raybaud, Franck Tessier
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Patent number: 8663345Abstract: 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. Neutralization of the alkaline stream, formed during the alkali-catalyzed transesterfication process, may proceed by the addition of a mineral or an organic acid.Type: GrantFiled: November 30, 2011Date of Patent: March 4, 2014Assignee: Seneca Landlord, L.L.C.Inventors: John P. Jackam, Joel M. Pierce, Jeffrey D. Jones
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Patent number: 8624048Abstract: 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: GrantFiled: December 15, 2010Date of Patent: January 7, 2014Assignee: IFP Energies NouvellesInventors: Aurelie Dandeu, Vincent Coupard, Laurent Bournay, Charlotte Rouquette
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Publication number: 20140005424Abstract: 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. The glycerin rich second liquid phase stream may further be purified to produce a purified glycerin product and a (second) wet alcohol stream.Type: ApplicationFiled: June 21, 2013Publication date: January 2, 2014Applicant: REG Seneca, LLCInventors: John P. Jackam, Derek J. Winkel, Jared A. Downey
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Patent number: 8614074Abstract: A process for the preparation of a composition comprising the cis9, trans11 and trans10, cis12 isomers of conjugated linoleic acid (CLA) comprises: providing a mixture comprising cis9, trans11 and trans10, cis12 isomers of conjugated linoleic acid (CLA) in which one of the cis9, trans11 and trans10, cis12 isomers is present in a first weight ratio X of at least 1.3:1 with respect to the other isomer; and subjecting the mixture to crystallization to form a composition comprising the cis9, trans11 and trans10, cis12 isomers in which one of the cis9, trans11 and trans10, cis12 isomers is present at a second weight ratio Y with respect to the other isomer, wherein Y is greater than X.Type: GrantFiled: April 4, 2007Date of Patent: December 24, 2013Assignee: Stepan Specialty Products, LLCInventors: Victoria Taran, Krishnadath Bhaggan, Jeroen Monster
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Publication number: 20130331587Abstract: This invention relates to an improved process for the preparation of green fatty acid methyl esters (FAME; commonly called as biodiesel) from different triglyceride oils using mixed metal oxides derived from layered double hydroxides (referred here as LDHs) as reusable solid heterogeneous base catalysts. This process uses very low alcohohoil molar ratio and catalyst and/or products are easily separable after the reaction through simple physical processes. The properties of thus obtained biodiesel meet the standard biodiesel values and can directly be used as transport fuel.Type: ApplicationFiled: February 10, 2012Publication date: December 12, 2013Inventors: Kannan Srinivasan, Sivashunmugam Sankaranarayanan, Churchil Angel Antonyraj
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Patent number: 8580988Abstract: A method for producing a high viscosity, low volatiles blown stripped plant-based oil is provided. The method may include the steps of: (i) obtaining a plant-based oil; (ii) heating the oil to at least 90° C.; (iii) passing air through the heated oil to produce a blown oil having a viscosity of at least 50 cSt at 40° C.; (iv) stripping the blown oil from step (iii) to reduce an acid value of the blown oil to from 5 mg KOH/g to about 9 mg KOH/g; (v) adding a polyol to the stripped oil from (iv); and (vi) stripping the oil from step (v) to reduce the acid value of the oil to less than 5.0 mg KOH/g or less.Type: GrantFiled: May 20, 2011Date of Patent: November 12, 2013Assignee: Cargill, IncorporatedInventors: Michael John Hora, Patrick Thomas Murphy
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Patent number: 8507702Abstract: A method for the continuous production of ester based organic compounds from renewable natural products via supercritical solvent processing in the presence of heterogeneous nano-structured catalysts. Fatty acid triglycerides may therefore be transesterified using heterogeneous nano-structured catalysts in the presence of supercritical alcohols to provide alkyl ester compounds and glycerine.Type: GrantFiled: March 29, 2011Date of Patent: August 13, 2013Assignee: Southwest Research InstituteInventors: Maoqi Feng, Chee-Kai Tan
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Patent number: 8481771Abstract: Processes for producing biodiesel compositions are disclosed. FFAs present in the triglycerides can be removed by reaction with isobutylene, or by Kolbe electrolysis. The Kolbe electrolysis can be performed on the starting material, or on the crude glycerol. The triglycerides are transesterified to form alkyl esters of the fatty acids and glycerol. The transesterification reaction can be catalyzed by an alkoxide, rather than a hydroxide, to help keep the glycerol by-product dry. The alkoxide salt can be neutralized by reaction with a dry acid, such as gaseous hydrogen chloride or sulfuric acid, and the resulting alcohol removed by distillation, and at least a portion of the neutralized salt can be removed by filtration or decantation. The process can provide improved biodiesel yields, and glycerol pure enough for use directly in glycerol ether manufacture.Type: GrantFiled: March 21, 2008Date of Patent: July 9, 2013Assignee: CPS Biofuels, Inc.Inventors: David Bradin, Guerry L. Grune
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Publication number: 20130131363Abstract: A surfactant composition for agricultural chemicals, containing fatty acid polyoxyalkylene alkyl ether expressed by the following general formula (I), R1CO(EO)m(PO)nOR2??(I) wherein the fatty acid polyoxyalkylene alkyl ether has a narrow ratio of 55% by mass or more, where the narrow ratio is expressed by the following formula (A): Narrow ratio=?i=nMAX?2i=nMAX+2Yi??(A)Type: ApplicationFiled: January 15, 2013Publication date: May 23, 2013Applicant: Lion CorporationInventor: Lion Corporation
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Patent number: 8445709Abstract: The present invention relates to systems and methods for producing and/or refining alkyl ester compositions. In an embodiment the invention includes a method of producing a refined fatty acid alkyl ester composition. The method can include contacting a fatty acid feedstock and an alcohol with a first metal oxide catalyst at a temperature of greater than 200 degrees Celsius and a pressure of greater than 500 psi to form an unrefined fatty acid alkyl ester composition. The method can further include combining the unrefined fatty acid alkyl ester composition with dimethyl carbonate to form a refining mixture. The method can also include contacting the refining mixture with a second metal oxide catalyst at a temperature of greater than 100 degrees Celsius to form a refined fatty acid alkyl ester composition. Other embodiments are also described herein.Type: GrantFiled: June 9, 2010Date of Patent: May 21, 2013Assignee: McNeff Research Consultants, Inc.Inventors: Clayton V. McNeff, Larry C. McNeff, Bingwen Yan, Daniel Thomas Nowlan
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Patent number: 8440847Abstract: 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: GrantFiled: September 29, 2010Date of Patent: May 14, 2013Assignee: 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: 8404005Abstract: In a method and system to produce biodiesel using an improved catalytic transesterification process, a first reactant and a second reactant are dispersed to form a laminar slug flow pattern within a microchannel of a microreactor, the first reactant and the second reactant being immiscible. The first reactant and the second reactant are mixed, thereby triggering a reaction between them to produce the biodiesel and glycerol, the mixing being convection-enhanced by shear stress induced circulation occurring within each slug of the reactants. The reaction takes place under a pressure that is less than 5 psi and under a temperature that is less than 70 degrees Celsius. Separation of the glycerol from the biodiesel occurs simultaneously with the mixing. Several microreactors are coupled in parallel to improve throughput of the biodiesel.Type: GrantFiled: September 10, 2009Date of Patent: March 26, 2013Assignee: Board of Regents, The University of Texas SystemInventors: Brian H. Dennis, Richard E. Billo, Christopher R. Oliver, John W. Priest, Elinor Kolesar
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Publication number: 20130072706Abstract: Tricyglycerols that may be converted to biofuel are recovered from oleaginous organisms in the natural and induced foam of wastewater treatment process plants. Growing oleaginous organisms in the form of comparatively dry foam simplifies harvest and is more efficient and efficacious than skimming the biomass off the top of the liquids that rely on less efficient centrifugation or filtration methods typically required to concentrate cells grown in liquids.Type: ApplicationFiled: March 16, 2012Publication date: March 21, 2013Applicant: PHASE BIOCONTROL RESEARCH, LLCInventors: Elizabeth J. Summer, Mei Liu, Sarah Dugleby
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Publication number: 20130036713Abstract: The present invention relates to a process for the preparation of an ester in a reactor, wherein at least a portion of the process components is led in a delivery stream outside the reactor over a heat transfer surface as a film, the ratio of the delivery stream to the heat transfer surface being in a range of from 0.25 to 3 m/h, a device, a process for the preparation of a thermoplastic composition comprising the ester prepared according to the invention, a process for the production of a shaped article comprising the ester according to the invention or the thermoplastic composition according to the invention, a process for the production of a packed product, a process for the production of an at least partly coated object, and uses of the esters according to the invention as an additive in various compositions.Type: ApplicationFiled: December 30, 2010Publication date: February 14, 2013Inventors: Peter Daute, Wilhelm Reiners, Martin Schäfer, Udo Frerichs, Hinrich Hildebrandt, Joern Ellerbrake
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Publication number: 20130041167Abstract: A method of treating tall oil pitch, which comprises sterol esters of fatty acids. According to the present invention, the esters of sterols and fatty acids are broken down, in which case especially formic acid esters or acetic acid esters of sterols are formed instead. The free fatty acids and sterol esters generated are distilled or separated in another way. Use of the present invention increases the yield of fatty acids and also facilitates the separation of sterols from tall oil pitch.Type: ApplicationFiled: March 28, 2011Publication date: February 14, 2013Applicant: FORCHEM OYInventors: Esko Kiviranta, Juhani Saviainen, Mikko Rintola
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Publication number: 20130019520Abstract: The present invention is directed to methods of making fatty acid esters from glycerides and free fatty acids.Type: ApplicationFiled: January 31, 2012Publication date: January 24, 2013Applicant: Brown UniversityInventors: Jason K. Sello, Aaron M. Socha
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Patent number: 8350069Abstract: The present invention provides a method and apparatus for reacting a natural oil with a short chain alcohol in the presence of alkaline catalyst, in which a mixture of natural oil, short chain alcohol and alkaline catalyst is fed in one direction along a pipe reactor under transitional or turbulent conditions, so that the reactants are mixed in a direction normal to the flow direction to a greater degree than in a direction parallel to the flow direction or so that the reactants are mixed in a direction normal to the flow direction, such that the time taken for 90% of the elements of fluid to pass through the reactor is within 20% of the mean residence time of reactant in the reactor. There is also provided a ship, comprising means for storing a raw material used in the synthesis of biodiesel, a plant for the synthesis of biodiesel and means for storing the biodiesel synthesized.Type: GrantFiled: October 19, 2007Date of Patent: January 8, 2013Assignee: Renewable Holdings LimitedInventors: Owen Matthew Davies, Richard David Jackson
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Publication number: 20130005005Abstract: Chemically modified lipids and methods for their preparation are provided.Type: ApplicationFiled: August 31, 2012Publication date: January 3, 2013Applicant: Solazyme, Inc.Inventors: Anthony G. Day, Geoffrey Brooks, Scott Franklin
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Patent number: 8328997Abstract: This invention relates to the design of a process by intermittent dielectric heating combined with a recycling system. This process consists in subjecting reagents to electromagnetic waves selected in the frequencies ranging between 300 GHz and 3 MHz intermittently using a recycling system. This process enables the treatment of oils that are hardly absorbent as well as great investment savings. This process enables operation on different scales, whether in laboratories, on a semi-industrial or industrial scale, without forfeiting the advantages of continuous dielectric heating.Type: GrantFiled: June 29, 2009Date of Patent: December 11, 2012Assignee: Aldivia SAInventors: Pierre Charlier De Chily, Mikaële Raynard
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Publication number: 20120297507Abstract: A method for producing leafy biomass from undifferentiated plant cells, the method comprising providing undifferentiated plant cells, contacting them with an agent that promotes differentiation of the cells into leafy tissue and growing the cells in a temporary liquid immersion culture system. This method of the invention may be used to produce polypeptides, and natural medicinal products, and can be used to capture carbon dioxide. A method of producing a polypeptide in plant cells in vitro comprising: providing undifferentiated plant cells containing chloroplasts that carry a transgenic nucleic acid molecule encoding the polypeptide, wherein the plant cells display homoplastomy; and propagating the cells according to the above method to produce leafy biomass containing the polypeptide.Type: ApplicationFiled: August 12, 2010Publication date: November 22, 2012Applicant: Imperial Innovations LimitedInventors: Franck Michoux, Peter Nixon, James Gerard McCarthy
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Publication number: 20120289725Abstract: The present invention provides a novel approach for the preparation of fatty alcohol esters of ?-hydroxy carboxylic acids. In one form of the invention, the target fatty alcohol ester of ?-hydroxy carboxylic acid is produced by converting a lower alkyl ester of ?-hydroxy carboxylic acid into a fatty alcohol ester of ?-hydroxy carboxylic acid via alcoholysis (i.e., transesterification). The transesterification process is an equilibrium reaction, catalyzed chemically (i.e., with acids or bases) or enzymatically, that is shifted in the desired direction to produce the desired product. One way of shifting the reaction in the direction of the desired product is by reducing the concentration of one of the products (e.g., distillation of a lower-boiling alcohol as it is formed). Another preferred way of shifting the reaction in the direction of the desired product is by increasing the concentration of one of the reactants.Type: ApplicationFiled: April 11, 2012Publication date: November 15, 2012Inventors: Gerald S. Jones, JR., Scott A. Goodrich, Joseph P. St. Laurent
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Publication number: 20120283460Abstract: Disclosed herein are methods of manufacturing renewable chemicals through the manufacture of novel triglyceride oils followed by chemical modification of the oils. Methods such as transesterification, hydrogenation, hydrocracking, deoxygenation, isomerization, interesterification, hydroxylation, hydrolysis and saponification are disclosed. Novel oils containing fatty acid chain lengths of C8, C10, C12 or C14 are also disclosed and are useful as feedstocks in the methods of the invention.Type: ApplicationFiled: July 16, 2012Publication date: November 8, 2012Applicant: Solazyme, Inc.Inventors: Scott Franklin, Aravind Somanchi, Karen Espina, George Rudenko, Penelope Chua
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Publication number: 20120283459Abstract: Mixed metal oxide catalysts (ZnO, CeO, La2O3, NiO, Al203, Si02, TiO2, Nd2O3, Yb2O3, or any combination of these) supported on zirconia (ZrO2) or hydrous zirconia are provided. These mixed metal oxide catalysts can be prepared via coprecipitation, impregnation, or sol-gel methods from metal salt precursors with/without a Zirconium salt precursor. Metal oxides/ZrO2 catalyzes both esterification and transesterification of oil containing free fatty acids in one batch or in single stage. In particular, these mixed metal oxides supported or added on zirconium oxide exhibit good activity and selectivity for esterification and transesterification. The low acid strength of this catalyst can avoid undesirable side reaction such as alcohol dehydration or cracking of fatty acids. Metal oxides/ZrO2 catalysts are not sensitive to any water generated from esterification. Thus, esterification does not require a water free condition or the presence of excess methanol to occur when using the mixed metal oxide catalyst.Type: ApplicationFiled: November 8, 2010Publication date: November 8, 2012Applicant: Wayne State UniversityInventors: Manhoe Kim, Steven O. Salley, K.Y. Simon Ng
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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: 20120277357Abstract: Presently disclosed are high purity unsaturated fatty acid esters with an ester moiety characterized by having from five to seven members in a ring structure, which esters when epoxidized find particular utility as primary plasticizers in flexible polyvinyl halide applications. Also disclosed are processes for making the high purity esters.Type: ApplicationFiled: January 4, 2011Publication date: November 1, 2012Applicant: ARCHER DANIELS MIDLAND COMPANYInventors: Erik Hagberg, Stephen Howard, George Poppe, Stephen D. Horton
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Publication number: 20120260929Abstract: A method for producing glycerin from one or more plants of genus Nicotiana is provided. The glycerin can be derived inter alia from Nicotiana species biomass or from seed. In certain embodiments, the glycerin is produced by either acid-catalyzed hydrolysis or base-catalyzed hydrolysis of acylglycerol-containing starting material derived from tobacco biomass or seed. The invention also provides articles and compositions including smoking articles and smokeless tobacco compositions that include glycerin produced from one or more plants of genus Nicotiana.Type: ApplicationFiled: April 18, 2011Publication date: October 18, 2012Inventors: William Coleman, Michael Francis Dube
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Patent number: 8288573Abstract: The present invention provides a process for preparing a bio-diesel, comprising, in the presence of an alkaline metal compound, reacting an oil-fat with C1-C6 monohydric alcohol in a reactor at a reaction temperature of from 130 to 280° C. and a reaction pressure of from 1 to 12 MPa, separating fatty acid esters from the reacted materials, so as to produce the bio-diesel, wherein said alkaline metal compound is present in an amount of 0.001-0.07 wt %, in terms of the metal thereof, relative to the weight of the oil-fat. The process provided in the present invention has the advantages of great throughput and high yield of the bio-diesel.Type: GrantFiled: December 15, 2006Date of Patent: October 16, 2012Assignees: China Petroleum & Chemical Corporation, Research Institute of Petroleum Processing, SinopecInventors: Haijing Wang, Zexue Du, Enze Min, Guoqiang Gao
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Patent number: 8288574Abstract: Method for producing C3H5(OH)3 and at least one of fatty acid methyl ester (FAME) and fatty acid ethyl ester (FAEE) includes mixing vegetable oils and animal fats, at least one of CH3OH and C2H5OH and at least one first catalyst to transesterify a portion of triglycerides and provide a first mixture. The first mixture is separated, with a first light phase being withdrawn and fed into a second mixer where it is mixed with at least one second catalyst to transesterify a further portion of the triglycerides to provide a second mixture. The second mixture is separated, with a second light phase being withdrawn and mixed with soapless C3H5(OH)3 to provide a dispersion which is separated by density difference. A phase containing at least one of raw FAME and raw FAEE is mixed with an aqueous acid, washed with water, with the water being expelled to provide FAME and FAEE product.Type: GrantFiled: September 5, 2008Date of Patent: October 16, 2012Assignee: Lurgi GmbHInventors: Rudolf Boensch, Helmut Saft, Peter Mitschke, Henning Buchold
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Publication number: 20120253057Abstract: A method for the continuous production of ester based organic compounds from renewable natural products via supercritical solvent processing in the presence of heterogeneous nano-structured catalysts. Fatty acid triglycerides may therefore be transesterified using heterogeneous nano-structured catalysts in the presence of supercritical alcohols to provide alkyl ester compounds and glycerine.Type: ApplicationFiled: March 29, 2011Publication date: October 4, 2012Applicant: SOUTHWEST RESEARCH INSTITUTEInventors: Maoqi FENG, Chee-Kai TAN
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Publication number: 20120232300Abstract: Processes for continuous preparation of bioproducts are described herein. The processes include contacting fatty acid glycerides with alcohols in the presence of an acidic heterogeneous catalyst and separating the fatty acid alkyl esters from the reaction products.Type: ApplicationFiled: March 7, 2012Publication date: September 13, 2012Inventors: William A. Summers, Rebecca Williams, Danny Gulledge, Robert Barrie Tripp
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Patent number: 8246699Abstract: The processes of producing the low pour point palm diesel particularly but not exclusively via esterification of C18, C18:1 and C18:2 mixed fatty acids with methanol or ethanol, or fractional distillation of methyl or ethyl esters of palm oil, palm kernel oil and palm oil products, or fractional distillation of methyl or ethyl esters of palm oil, palm kernel oil and palm oil products, followed by crystallization, or crystallization of methyl or ethyl esters of palm oil, palm kernel oil and palm oil products, or crystallization of methyl or ethyl esters of palm oil, palm kernel oil and palm oil products, followed by fractional distillation.Type: GrantFiled: April 20, 2009Date of Patent: August 21, 2012Assignee: Malaysian Palm Oil BoardInventors: Choo Yuen May, Cheng Sit Foon, Yung Chee Liang, Harrison Lau Nik Nang, Ma Ah Ngan, Yusof Basiron
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Publication number: 20120197031Abstract: A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent selected from the group consisting of phosphorous acid, phosphinic acid, and a combination thereof; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product. Methods for suppressing isomerization of olefin metathesis products produced in a metathesis reaction, and methods of producing fuel compositions are described.Type: ApplicationFiled: December 22, 2011Publication date: August 2, 2012Inventors: Bruce E. Firth, Sharon E. Kirk, Vasudeo S. Gavaskar
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Publication number: 20120184758Abstract: The invention relates to a continuous method for producing esters, in which at least one polyol ester of formula (I) (R1—COO)mR2 (I), where R1 represents hydrogen or an optionally substituted hydrocarbon group containing 1 to 50 carbon atoms, R2 represents an optionally substituted hydrocarbon group containing 2 to 10 carbon atoms, and m represents a number from 2 to 10 and is smaller than or equal to the number of carbon atoms in R2, is reacted with at least one monohydric alcohol of formula (II) R3—OH (II), where R3 represents an optionally substituted hydrocarbon group containing 1 to 30 C atoms, using microwave radiation in a reaction tube, the longitudinal axis of which extends in the direction of propagation of the microwaves of a single-mode microwave applicator, so as to obtain at least one ester of formula (III) R1—COO—R3 (III), where R1 and R3 have the meanings indicated above.Type: ApplicationFiled: September 3, 2010Publication date: July 19, 2012Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Matthias Krull, Roman Morschhaeuser
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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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Publication number: 20120167648Abstract: 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: ApplicationFiled: March 9, 2012Publication date: July 5, 2012Inventor: Antonio Cantizani
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Publication number: 20120157699Abstract: A multi-stage reactor system for preparing biodiesel is used to increase efficiency and yield and reduce impurities. A three-stage transesterification reaction for preparing biodiesel can include one high-shear cavitation reactor and two low-shear cavitation reactors, preferably in series, and optionally one or more separation vessels for removing waste and recycling triglyceride feedstock, catalyst and alcohol to the high-shear cavitation reactor.Type: ApplicationFiled: December 14, 2011Publication date: June 21, 2012Applicant: ARISDYNE SYSTEMS, INC.Inventors: Oleg Kozyuk, Peter Reimers, Paul A. Reinking
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Publication number: 20120142952Abstract: In one embodiment, a method for the production of alkyl esters comprises: introducing liquid biomass and an alcohol to a first transesterification reactor at a point in a lower 25% of the reactor; reacting the liquid biomass and the alcohol to form a liquid glycerol and a liquid alkyl ester, wherein greater than or equal to about 75 mass % of the liquid glycerol moves towards a bottom of the first transesterification reactor; removing a liquid alkyl ester stream from the first transesterification reactor; and removing the liquid glycerol from the first transesterification reactor. The liquid biomass and the alcohol form a combined liquid stream that flows through the first transesterification reactor in a laminar flow.Type: ApplicationFiled: February 15, 2012Publication date: June 7, 2012Applicant: UNIVERSITY OF CONNECTICUTInventors: Richard Parnas, Clifford Weed, Nicholas Leadbeater, Matthew Boucher
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Patent number: 8193383Abstract: 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: GrantFiled: July 31, 2007Date of Patent: June 5, 2012Assignee: Lurgi GmbHInventors: Helmut Saft, Klaus Hohmann, Rudolph Bönsch
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Publication number: 20120130101Abstract: The present invention relates to a catalyst used in the manufacture of fatty acid alkyl esters and a method for preparing fatty acid alkyl esters using the same. The invention provides a high hardness solid ceramic metal catalyst obtained by mixing and sintering 0 wt %-80 wt % active catalyst material with a support material, wherein the support material is a silica alumina that is a mixed metal oxide and the active catalyst material is at least one of oxides, carbonates, and hydroxides of any kind selected from magnesium (Mg), calcium (Ca), zinc (Zn), titanium (Ti), manganese (Mn), vanadium (V), beryllium (Be), copper r (Cu), zirconium (Zr), strontium (Sr), tin (Sn), and barium (Ba). In addition, the invention provides a method for preparing fatty acid alkyl esters by performing transesterification and esterification of animal and vegetable oils and alcohols in the state where the ceramic metal catalyst is fixed within a reactor without processes for removing and purifying the catalyst.Type: ApplicationFiled: November 2, 2009Publication date: May 24, 2012Applicant: S.M.POT Co., LtdInventors: Jeong Woo Yoo, Hae Reun Jang, Hee Jun Hyoung
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Publication number: 20120123140Abstract: 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. Neutralization of the alkaline stream, formed during the alkali-catalyzed transesterfication process, may proceed by the addition of a mineral or an organic acid.Type: ApplicationFiled: November 30, 2011Publication date: May 17, 2012Applicant: Seneca Landlord, LLCInventors: John P. Jackam, Joel M. Pierce, Jeffrey D. Jones
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Publication number: 20120101288Abstract: The present invention describes a process for the production of alkyl esters of fatty acids and glycerine employing, in a reaction section, at least one transesterification reaction between an animal or vegetable oil and an aliphatic mono-alcohol, and using a heterogeneous solid catalyst, in which the energy balance is improved by thermal integration of the energy released during the mono-alcohol condensation step.Type: ApplicationFiled: October 20, 2011Publication date: April 26, 2012Applicant: IFP Energies nouvellesInventors: Laurent Bournay, Vincent Coupard, Pierre-Yves Martin, Yves Scharff, Yann Lepine
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Publication number: 20120066965Abstract: A method to transesterify triglycerides in the presence of a catalyst system comprising a transesterification catalyst selected from the group of the alkali metal and alkaline earth metal alkoxides and the alkali metal hydroxides, and at least one activator other than the transesterification catalyst, selected from the group comprising salt compounds, titanates and non-salt compounds having a density of at least 0.9 g/ml, is provided. Additionally provided is a method to prepare biodiesel by transesterification of a natural fat.Type: ApplicationFiled: September 16, 2011Publication date: March 22, 2012Applicant: EVONIK DEGUSSA GmbHInventors: Johannes Ruwwe, Martin Lichtenheldt, Wolfgang-Wilhelm Orlia
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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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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: 20120022279Abstract: A catalyst is described which comprises at least one IZM-2 zeolite and at least one matrix, said zeolite having a chemical composition expressed as the anhydrous base in terms of moles of oxides by the following general formula: XO2: aY2O3: bMnO, in which X represents at least one tetravalent element, Y represents at least one trivalent element and M is at least one alkali metal and/or alkaline-earth metal, a and b respectively representing the number of moles of Y2O3 and MnO; and a is in the range 0.001 to 0.5, b is in the range 0 to 1 and n is in the range 1 to 2. Said catalyst is used in various processes for the transformation of hydrocarbon feeds.Type: ApplicationFiled: July 21, 2009Publication date: January 26, 2012Applicant: IFP Energies nouvellesInventors: Amandine Cabiac, Nicolas Cadran, Emmanuelle Guillon, Vincent Lecocq, Sylvie Maury
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Publication number: 20120004433Abstract: A method of preparing 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 catalyst of nitrogen-containing metallophosphate type.Type: ApplicationFiled: June 1, 2011Publication date: January 5, 2012Applicant: IFP Energies nouvellesInventors: Delphine BAZER-BACHI, Francois Chevire, Vincent Lecocq, Erwan Ray, Pascal Raybaud, Franck Tessier
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Publication number: 20110319504Abstract: The invention relates to a method for processing mixtures of carboxylic acids obtained as hydrolysis products of suberin and cutin, particularly suberin and cutin isolated from birch bark, to give mono-, oligo- and polyesters, or corresponding ester-ethers, as well as the use of the products thus obtained as lubricants, fuel components, plasticizers, surface active agents, environmentally friendly agents for modifying wood, binders in coatings, adhesives, printing inks and composites, further in various cosmetic applications.Type: ApplicationFiled: September 8, 2011Publication date: December 29, 2011Applicant: VALTION TEKNILLINEN TUTKIMUSKESKUSInventors: Salme KOSKIMIES, Janne Hulkko, Pauliina Pitkänen, Nina Heiskanen, Jari Yli-Kauhaluoma, Kristiina Wähälä
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Publication number: 20110312044Abstract: In an alcohol fermentation process, oil derived from biomass is chemically converted into an extractant available for in situ removal of a product alcohol such as butanol from a fermentation broth. The glycerides in the oil can be chemically converted into a reaction product, such as fatty acids, fatty alcohols, fatty amides, fatty acid methyl esters, fatty acid glycol esters, and hydroxylated triglycerides, and mixtures thereof, which forms a fermentation product extractant having a partition coefficient for a product alcohol greater than a partition coefficient of the oil of the biomass for the product alcohol. Oil derived from a feedstock of an alcohol fermentation process can be chemically converting into the fermentation product extractant.Type: ApplicationFiled: June 17, 2011Publication date: December 22, 2011Applicant: BUTAMAX(TM) ADVANCED BIOFUELS LLCInventors: DOUGLAS ROBERT ANTON, JELENA CIRAKOVIC, BRUCE A. DINER, MICHAEL CHARLES GRADY, FRANCIS J. WOERNER