Another Reactant Contains Alcoholic Or Phenolic Hydroxy (e.g., Methy Ricinoleate, Etc.) Patents (Class 554/167)
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Patent number: 12256752Abstract: In each of its various embodiments, the present invention discloses microemulsions that carry antioxidants.Type: GrantFiled: September 13, 2019Date of Patent: March 25, 2025Assignee: ARCHER-DANIELS-MIDLAND COMPANYInventors: Shireen Baseeth, Mark Matlock, Kirby Swinehart, Lori Wicklund
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Patent number: 11795124Abstract: Herein is provided a process for producing renewable products, such as alkenes, from a feedstock of biological origin. The process includes subjecting a feedstock including fatty acid glycerides and optionally free fatty acids, wherein at least one hydrocarbon chain is unsaturated, to esterification reaction in the presence of an alcohol. The ester stream thereby obtained is then fractionated and a fraction including esters of unsaturated C18 fatty acids is subjected to metathesis conditions in the presence of an alkene to obtain metathesis products. Fractionation of the metathesis products includes recovery of at least renewable 1-decene, and unsaturated C10-C15 fatty acid esters.Type: GrantFiled: September 25, 2020Date of Patent: October 24, 2023Assignee: Neste OyjInventors: Jukka Hietala, Anja Leminen, Virpi Rämö, Jukka Räsänen
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Patent number: 11591545Abstract: The present invention relates to a method of producing fatty acid alkyl ester from an organic oil source containing at least one free fatty acid, wherein the oil source has an acid number of at least 30 mg KOH/g oil source and wherein the method comprises the steps of a) reacting the oil source with glycerol at a temperature, which does not exceed 180° C. during the reaction, in the presence of a catalyst comprising at least one alkyl or aryl sulfonic acid or an homoanhydride thereof; and b) transesterification of the reaction product from step a) with an alkanol; and c) isolating the fatty acid alkyl ester from the reaction product of step b).Type: GrantFiled: October 7, 2019Date of Patent: February 28, 2023Assignee: BASF SEInventors: Paul Klingelhoefer, Michael Koch, Michael Schier, Juergen Schneider
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Patent number: 11472995Abstract: The present application discloses water-based drilling fluid system compositions and methods for making water-based drilling fluids systems. According to one embodiment, a drilling fluid system may include a drilling fluid and a lubricant. The lubricant may be synthesized from plant-based raw material oil.Type: GrantFiled: July 17, 2018Date of Patent: October 18, 2022Assignee: Saudi Arabian Oil CompanyInventors: Jothibasu Ramasamy, Md Amanullah
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Patent number: 11198893Abstract: Provided is a method for producing an unsaturated fatty acid oxide (e.g. ?3 fatty acid oxide) that is new and has more beneficial features compared to conventional technologies. This method uses a lipoxygenase-containing composition (e.g. a lipoxygenase-containing composition derived from beans) as a lipoxygenase enzyme, and also uses a freezing method with organic solvent extraction. The present invention makes it possible to produce an unsaturated fatty acid oxide (e.g. ?3 fatty acid oxide) efficiently and at a low cost. The present invention also provides a pharmaceutical composition containing an ?3 fatty acid oxide isolated and purified by this method as an active ingredient.Type: GrantFiled: June 19, 2017Date of Patent: December 14, 2021Assignee: Bizen Chemical Co., Ltd.Inventors: Shiho Saito, Yoshihisa Misawa, Naomichi Baba, Hiroshi Tabata, Tadahiro Tsushima, Jun Fujii
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Patent number: 10988708Abstract: Provided are industrial processes for producing a fatty acid alkyl ester from a natural oil feedstock or a mixed lipid feedstock, wherein the natural oil feedstock comprises a free (un-esterified) organic acid such as a free fatty acid, comprising: producing fatty acid alkyl esters using an alcoholysis reaction such as a vapor phase alcoholysis reaction or a supercritical alcoholysis reaction, wherein the alcoholysis reaction takes place under conditions comprising: mixing the natural oil feedstock and/or mixed lipid feedstock and alcohol into an alcoholysis reactor or equivalent, and then depressurizing, and then recovering the fatty acid alkyl esters from the alcoholysis reactor or equivalent by distillation in a distillation column, leaving a still pitch or distillation bottoms in the distillation column or equivalent, wherein the fatty acid alkyl esters can be removed from the alcoholysis reactor or equivalent with or without cooling of the reaction mixture prior to depressurization.Type: GrantFiled: March 10, 2020Date of Patent: April 27, 2021Assignee: Inventure Renewables, Inc.Inventors: Cory O'Neil Blanchard, Ryan Alexander Long, Hayden Sawyer
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Patent number: 10933111Abstract: This disclosure is related to compositions and methods for treating dry dye disorders.Type: GrantFiled: March 5, 2020Date of Patent: March 2, 2021Assignee: Boston Biotechnology US CORPInventor: Dan Yang
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Patent number: 10888842Abstract: The present invention relates to a method for manufacturing a catalyst for synthesizing a fatty acid methyl or ethyl ester and a method for manufacturing a fatty acid methyl or ethyl ester using the catalyst. It provides a method for manufacturing a solid catalyst by mixing the oxides of manganese as active catalytic material and the soda lime glass as carrier wherein the content of the oxides of manganese is in the range of 0.1 w % to 70 w %, molding the mixture to spherical or cylindrical shape and sintering the molded catalyst. It also provides a method for manufacturing fatty acid methyl or ethyl ester with high purity by reacting fatty acid or a mixture of oil and fatty acid with methanol or ethanol by placing the solid catalyst in the reactor.Type: GrantFiled: June 1, 2017Date of Patent: January 12, 2021Inventor: Seong Min Yoo
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Patent number: 10851326Abstract: A method for producing a high viscosity, low volatiles blown stripped oil blend is provided. The method may include the steps of: (i) obtaining an oil blend of corn stillage oil and soybean oil having a weight ratio of corn stillage oil to soybean oil of from about 1:2 to 3:1; (ii) heating the oil blend to at least 90° C.; (iii) passing air through the heated oil blend to produce a blown oil having a viscosity of at least 50 cSt at 40° C.; and (iv) stripping the blown oil from step (iii) to reduce an acid value of the blown oil to less than 5.0 mg KOH/gram.Type: GrantFiled: November 15, 2018Date of Patent: December 1, 2020Assignee: CARGILL, INCORPORATEDInventors: Michael John Hora, Patrick Thomas Murphy, John Carl Tolfa
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Patent number: 10780433Abstract: The invention relates to a composition comprising: at least one alkane-sulphonic acid R—SO3H wherein R represents a saturated, linear or branched, hydrocarbon chain comprising from 1 to 4 carbon atoms, which can or cannot be substituted by at least one halogen atom, at least one aryl-sulphonic acid; and optionally at least one solvent, of which the proportions are as defined in the description. The invention also relates to the use of composition in a fatty acid esterification method.Type: GrantFiled: November 20, 2017Date of Patent: September 22, 2020Assignee: Arkema FranceInventors: Jean-Alex Laffitte, Bernard Monguillon, Kuan Huwa Tan
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Patent number: 10479860Abstract: A method for preparing a bio-based polycarbonate ester containing a repeating unit according to Formula 1 which comprises residue of Isosorbide and residue of CHDA (1,4-cyclohexanedicarboxylic acid).Type: GrantFiled: January 12, 2016Date of Patent: November 19, 2019Assignee: SK CHEMICALS CO., LTD.Inventors: Kwang Sei Oh, Jong-In Lee
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Patent number: 10155717Abstract: 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: GrantFiled: March 7, 2016Date of Patent: December 18, 2018Assignee: SBI BioEnergyInventors: Inder Pal Singh, Shradha Singh, Ritesh Patel, Bharat Mistry, Manish Mehta, Peter Omolo Otieno
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Patent number: 10081590Abstract: A device and a process for producing undecylenic acid methyl ester using methyl ricinoleate as raw material are provided. The device comprises a feed pump, a raw material pre-heater, a microwave catalytic reactor, a microwave generator, a temperature controller and an infrared sensor, a condenser, a product tank and a discharge pump. The feed pump is connected with the raw material pre-heater, which is connected with the inlet of the microwave catalytic reactor. The outlet of the microwave catalytic reactor is connected with the condenser, which is connected to the product tank and the discharge pump. The microwave catalytic reactor is located in the microwave generator, which is connected with the temperature controller and the infrared sensor. The process is as follows: high-purity methyl ricinoleate, used as the raw material, is converted to methyl undecene and heptaldehyde by microwave-assisted pyrolysis process, followed by isolation and purification to produce methyl undecene.Type: GrantFiled: August 26, 2017Date of Patent: September 25, 2018Assignee: Zhejiang University of TechnologyInventors: Yong Nie, Ying Duan, Ruchao Gong, Shangzhi Yu, Meizhen Lu, Jianbing Ji
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Patent number: 10030205Abstract: The present disclosure concerns embodiments of a catalyst system, such as a mixed catalyst composition, that can be used to make biofuel. In some embodiments, the mixed catalyst composition can comprise an inorganic catalyst and an organic catalyst, such as a cyclic organic catalyst. In particular disclosed embodiments, a mixed catalyst composition comprising, consisting essentially of, or consisting of an inorganic catalyst and an organic catalyst can be used to enhance the production of biofuel, such as biodiesel, by reducing the amount of time needed to make the biofuel as compared to that needed for the inorganic catalyst or the organic catalyst independently. Also disclosed herein are combinations and kits comprising, consisting essentially of, or consisting of embodiments of a mixed catalyst composition.Type: GrantFiled: July 31, 2015Date of Patent: July 24, 2018Assignee: Board of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada, RenoInventor: Dev Chidambaram
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Patent number: 9975991Abstract: Disclosed is a bio-based polycarbonate ester comprising: (i) repeat unit 1 obtained from a condensation reaction of 1,4:3,6-dianhydrohexitol and carbonate; and (ii) repeat unit 2 obtained from a condensation reaction of 1,4:3,6-dianhydrohexitol and 1,4-cyclohexanedicarboxylate; and a preparation method for the bio-based polycarbonate ester, comprising the steps of: (1) preparing a compound 1,4-diphenyl-cyclohexanedicarboxylate through a trans-esterification or esterification reaction of a compound represented by and phenol; and (2) preparing a compound comprising a repeat unit represented by through a polycarbonate melt polycondensation reaction of the 1,4-diphenyl-cyclohexanedicarboxylate prepared in step (1), a compound represented byType: GrantFiled: February 28, 2017Date of Patent: May 22, 2018Assignee: SK CHEMICALS CO., LTD.Inventors: Kwang Sei Oh, Il-Hoon Cha, Ji-hoon Kim
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Patent number: 9909077Abstract: The present invention provides a method for producing a refined fatty acid alkyl ester (FAAE) product from feed-stocks containing free fatty acids. The method comprises glycerolysis and transesterification processes combined with end-product refining. Products produced from a transesterification reaction are separated into a crude FAAE stream and a crude glycerin stream. The crude glycerin stream is further processed to produce a glyceride stream from which additional FAAEs may be produced.Type: GrantFiled: July 9, 2014Date of Patent: March 6, 2018Assignee: REG Seneca, LLCInventors: David A. Slade, Derek J. Winkel, Jared A. Downey
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Patent number: 9725397Abstract: 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: GrantFiled: June 21, 2013Date of Patent: August 8, 2017Assignee: REG Seneca, LLCInventors: John P. Jackam, Derek J. Winkel, Jared A. Downey
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Patent number: 9643163Abstract: A transesterification catalyst that is heterogeneous and a method for preparing said transesterification catalyst are provided. The catalyst can be used in a variety of transesterification reactor configurations including CSTR (continuous stirred tank reactors), ebullated (or ebullating) beds or any other fluidized bed reactors, and PFR (plug flow, fixed bed reactors). The catalyst can be used for manufacturing commercial grade biodiesel, biolubricants and glycerin.Type: GrantFiled: June 29, 2015Date of Patent: May 9, 2017Assignee: CRYSTAPHASE PRODUCTS, INC.Inventors: Umakant Pravinchandra Joshi, Peter Gregory Ham
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Patent number: 9556398Abstract: 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 90C; (iii) passing air through the heated oil to produce a blown oil having a viscosity of at least 200 cSt at 40C; (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: November 9, 2015Date of Patent: January 31, 2017Assignee: CARGILL, INCORPORATEDInventors: Michael John Hora, Patrick Thomas Murphy
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Patent number: 9540590Abstract: A process and a system for producing a fatty acid alkyl ester from an alcohol and a feedstock containing transesterifiable lipids are provided.Type: GrantFiled: May 29, 2014Date of Patent: January 10, 2017Assignee: POLYVALOR, LIMITED PARTNERSHIPInventors: Gregory Patience, Mahesh Edake, Cristian Neagoe, Daria Camilla Boffito
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Patent number: 9511621Abstract: A heat transfer label comprising a support portion and a transfer portion for transfer of the transfer portion from the support portion to an article. Heat is applied to the support portion while the transfer portion is placed into contact with the article. The support portion comprises a release layer including a synthetic wax.Type: GrantFiled: February 4, 2011Date of Patent: December 6, 2016Assignee: Multi-Color CorporationInventor: Jean-Paul Laprade
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Patent number: 9487805Abstract: A variety of betaine esters, including dialkylaminoalkyl cocoate betaines and dialkylaminoalkyl hydrogenated cocoate betaines are disclosed. These betaines can be advantageously prepared in high yield and purity by a three-step transiterification chemoenzymatic process or a two-step direct esterficiation chemoenzymatic process. These betaine esters have excellent surfactant properties.Type: GrantFiled: September 3, 2015Date of Patent: November 8, 2016Assignee: Eastman Chemical CompanyInventors: Christopher Harlan Burk, Stephanie Kay Clendennen, Neil Warren Boaz
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Patent number: 9476009Abstract: The present invention provides a method of producing fatty acid alkyl esters from a lipid, comprising steps of introducing a gas comprising vapor of an alcohol selected from methanol, ethanol, 1-propanol, iso-propanol and butanols, into the lipid in a form of bubbles to enable the bubbles to pass through the lipid and be discharged from the lipid. The product may then be subjected to a transesterification process catalyzed by a base catalyst. The present invention is robust with low quality feedstocks thus significantly reduce production cost for biodiesel.Type: GrantFiled: April 20, 2015Date of Patent: October 25, 2016Assignees: Drexel University, Environmental Fuel Research, LLCInventors: Richard Allan Cairncross, Megan Elizabeth Hums, Colin James Stacy
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Patent number: 9416336Abstract: Methods of producing fatty acid ethyl esters (FAEE) using a direct transesterification process are described. The direct transesterification process uses low levels of chemical solvents, acid catalysts, and heating energy to produce the FAEE in a method with increased efficiency in a co-solvent system. The FAEE produced may be used in a variety of products including health, beauty, nutraceutical, and cosmetic products.Type: GrantFiled: October 7, 2015Date of Patent: August 16, 2016Assignee: HELIAE DEVELOPMENT LLCInventor: Sandip Shinde
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Patent number: 9365801Abstract: A system and method for the conversion of high free fatty acid (HFFA) containing oils defined as oils containing 20-100% free fatty acids (FFA) and low free fatty acid (LFFA) containing oils defined as oils containing 1-20% free fatty acids (FFA) into oil with less than 0.5% FFA (defined as NFFA oil) includes a combination of partial glycerolysis of HFFA oils to produce LFFA oils and subsequent stripping of LFFA oils to produce NFFA oils via steam distillation.Type: GrantFiled: February 4, 2013Date of Patent: June 14, 2016Assignee: Technochem International, Inc.Inventor: Sanjeev Agarwal
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Patent number: 9364770Abstract: A portable biodiesel manufacturing or processing plant for processing on continuous basis a raw plant based oil feedstock to form biodiesel.Type: GrantFiled: December 20, 2012Date of Patent: June 14, 2016Assignee: The Biocube Corporation Ltd.Inventors: Laurence Baum, A Alexander Kelly
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Patent number: 9303233Abstract: A method for producing diesel grade fuel of plant origin by transesterifying a refined vegetable oil with a charge of a C1-C4 alcohol in the presence of a catalyst and at least 0.2 parts by volume, related to unit volume of refined vegetable oil, of an aliphatic hydrocarbon solvent with a boiling point of ?42° C. to 200° C., comprises mixing the oil, alcohol, catalyst and solvent in a single reaction vessel under homogeneous conditions which promote transesterification to 95-98% completion and which suppress reverse glycerolysis, without stopping transesterification to remove by-product polar glycerol, and without subjecting the oil/fuel mixture to a further transesterification step with a fresh charge of alcohol and catalyst.Type: GrantFiled: January 29, 2009Date of Patent: April 5, 2016Assignee: QS Biodiesel LimitedInventor: András Kovács
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Patent number: 9255240Abstract: A system and method for the conversion of high free fatty acid (HFFA) containing oils defined as oils containing 20-100% free fatty acids (FFA) and low free fatty acid (LFFA) containing oils defined as oils containing 1-20% free fatty acids (FFA) into oil with less than 0.5% FFA (defined as NFFA oil) includes a combination of partial glycerolysis of HFFA oils to produce LFFA oils and subsequent stripping of LFFA oils to produce NFFA oils via steam distillation.Type: GrantFiled: February 4, 2013Date of Patent: February 9, 2016Assignee: Technochem International, Inc.Inventor: Sanjeev Agarwal
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Patent number: 9234158Abstract: The invention relates to a continuous process for pretreatment of an oil feedstock comprising at most 20% by weight of free fatty acids by esterification of free fatty acids in which a vertical liquid/liquid contactor containing an esterification catalyst in solid form is supplied in counter-current by an alcohol feedstock comprising at least 20% by weight of an alcohol and said oil feedstock, with said contactor being operated at a temperature of between 25 and 120° C., with said contactor performing the contact in liquid-liquid counter-current between a heavy phase and a light phase, with said heavy phase being able to be either an oil-rich phase or an alcohol-rich phase.Type: GrantFiled: December 15, 2014Date of Patent: January 12, 2016Assignee: IFP Energies NouvellesInventors: Vincent Coupard, Laurent Bournay, Eszter Toth, Sylvie Maury
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Patent number: 9029583Abstract: 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: GrantFiled: February 10, 2012Date of Patent: May 12, 2015Assignee: Council of Scientific & Industrial ResearchInventors: Kannan Srinivasan, Sivashunmugam Sankaranarayanan, Churchil Angel Antonyraj
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Patent number: 9000197Abstract: 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: GrantFiled: September 3, 2010Date of Patent: April 7, 2015Assignee: Clariant Finance (BVI) LimitedInventors: Matthias Krull, Roman Morschhaeuser
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Patent number: 8980807Abstract: A method for producing a high viscosity, low volatiles blown stripped oil blend is provided. The method may include the steps of: (i) obtaining an oil blend of corn stillage oil and soybean oil having a weight ratio of corn stillage oil to soybean oil of from about 1:2 to 3:1; (ii) heating the oil blend to at least 90° C.; (iii) passing air through the heated oil blend to produce a blown oil having a viscosity of at least 50 cSt at 40° C.; and (iv) stripping the blown oil from step (iii) to reduce an acid value of the blown oil to less than 5.0 mg KOH/gram.Type: GrantFiled: May 20, 2011Date of Patent: March 17, 2015Assignee: Cargill, IncorporatedInventors: Michael John Hora, Patrick Thomas Murphy, John Carl Tolfa
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Patent number: 8969604Abstract: 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: GrantFiled: January 15, 2013Date of Patent: March 3, 2015Assignee: Lion CorporationInventors: Akinori Kanetani, Hiroyuki Izumoto, Shiro Sato, Takaaki Kano
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Patent number: 8962873Abstract: 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: GrantFiled: March 7, 2012Date of Patent: February 24, 2015Assignee: Benefuel, Inc.Inventors: William A. Summers, Rebecca Williams, Danny Gulledge, Robert Barrie Tripp
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Publication number: 20150037852Abstract: A method for reducing the free fatty acid content of a feedstock includes the steps of providing a free-fatty-acid-containing feedstock, treating the free-fatty-acid-containing feedstock to reduce the free fatty acid content thereof, where the step of treating includes combining at least one of an algae and a coagulant to the free-fatty-acid-containing feedstock, and producing a product from the treated feedstock.Type: ApplicationFiled: August 4, 2014Publication date: February 5, 2015Inventors: Lu-Kwang Ju, Majid Hosseini
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Patent number: 8936922Abstract: 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: GrantFiled: April 11, 2012Date of Patent: January 20, 2015Assignee: Chemsmart, LLCInventors: Gerald S. Jones, Jr., Scott A. Goodrich, Joseph P. St. Laurent
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Patent number: 8916721Abstract: The present invention is directed to ester compositions which result from the trans-esterification of a triglyceride having an iodine value of between 85 and 175 mg KOH/gm with a fatty alcohol having a melting point of between 35° and 75° C., followed by cooling and removal of the polar phase which results. Surprisingly, we have found the composition has unique properties when used in cosmetic applications.Type: GrantFiled: June 15, 2012Date of Patent: December 23, 2014Assignee: SurfaTech CorporationInventors: Thomas G. O'Lenick, Christopher J. Tarletsky
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Publication number: 20140346414Abstract: A dielectric fluid composition for electrical apparatus comprises a functionalized 12-hydroxy stearic acid having desirable properties including a pour point less than ?30° C. and a fire point greater than 250° C. It may be prepared by a process wherein 12-hydroxy methyl stearate is transesterified by reaction with a C3-C20 alcohol to form an alkyl-12-hydroxy stearate, followed by esterification thereof with a linear or branched C4-C20 carboxylic acid. This acid may be a free acid chloride, a fatty acid, a carboxylic acid anhydride, or combination thereof. The resulting functionalized 12-hydroxy stearic acid exhibits improved thermoxidative capability, low temperature flowability, and increased fire point.Type: ApplicationFiled: September 26, 2012Publication date: November 27, 2014Applicant: DOW GLOBAL TECHNOLOGIES LLCInventors: Suh Joon Han, Dirk B. Zinkweg, Zenon Lysenko
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Publication number: 20140330033Abstract: Apparatus and related methods for reacting a natural oil with a short chain alcohol in the presence of an alkaline catalyst and mesh to produce biodiesel, significantly decreasing the amount of time for the glycerol byproduct to settle out of the reaction mixture. The process for the production of biodiesel includes providing animal or vegetable oil to create a first component, combining a short chain alcohol with a strong base to create a second component, and combining the first and second components together in the presence of a mesh, such that the mesh is in contact with the combined components. The combined compositions represent a reaction mixture that undergo a transesterification reaction and produce fatty acid methyl ester biodiesel and also a glycerol byproduct. The mesh material that is present during the transesterification reaction decreases the amount of time required for the glycerol byproduct to settle out of the reaction mixture.Type: ApplicationFiled: April 11, 2014Publication date: November 6, 2014Inventors: JEFFERY THOMPSON, JOHN K. COOPER, MARIO A. OYANADER
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Patent number: 8871961Abstract: A process for continuous production of biodiesel from vegetable oils or animal fats by transesterification with methanol or ethanol to give crude fatty acid alkyl esters, subsequent washing with water in a wash column to remove water-soluble impurities, subsequent drying by vaporization of the water content and subsequent removal of steryl glycosides by adsorption onto calcium bentonite, wherein the adsorption column(s) used is/are regenerated in a first step, for desorption of the steryl glycosides, by rinsing with a mixture consisting of fatty acid alkyl esters and methanol or ethanol, and in a subsequent second step, for removal of methanol residues, by rinsing with fatty acid alkyl esters or with gaseous nitrogen or carbon dioxide.Type: GrantFiled: March 2, 2011Date of Patent: October 28, 2014Assignee: Air Liquide Global E&C Solutions Germany GmbHInventors: Eckhard Seidel, Rudolf Boensch, Norbert Palauschek, Helmut Saft
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Patent number: 8865922Abstract: 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: GrantFiled: March 28, 2011Date of Patent: October 21, 2014Assignee: Forchem OyInventors: Esko Kiviranta, Juhani Saviainen, Mikko Rintola
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Patent number: 8853436Abstract: Method for transesterification of fatty acid esters. The method includes contacting (i) a catalyst comprising at least one of barium oxide and apatite with (ii) a reaction medium comprising at least one of vegetable oil and fats.Type: GrantFiled: October 18, 2013Date of Patent: October 7, 2014Assignee: Petroleo Brasileiro S.A.-PetrobrasInventors: Márcio de Figueiredo Portilho, Alexander Rangel Bastos
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Publication number: 20140252281Abstract: A dielectric fluid composition for electrical apparatus comprises a functionalized methyl-12-carboxy methyl stearate having desirable properties including a pour point less than ?30° C. and a fire point greater than 250° C. It may be prepared by a process wherein methyl-12-hydroxy methyl stearate is transesterified by reaction with a C3-C20 alcohol to form the hydroxy methyl ester, followed by reaction with a linear or branched C4-C20 carboxylic acid selected from free acid chlorides, fatty acids, carboxylic acid anhydrides, and combinations thereof. The second step serves to end-cap the hydroxyl groups, thereby producing the functionalized methyl-12-carboxy methyl stearate compound that exhibits improved thermoxidative stability and low temperature flowability, as well as increased fire point.Type: ApplicationFiled: September 26, 2012Publication date: September 11, 2014Applicant: DOW GLOBAL TECHNOLOGIES LLCInventors: Suh Joon Han, Dirk B. Zinkweg, Zenon Lysenko
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Patent number: 8802877Abstract: 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: GrantFiled: December 17, 2009Date of Patent: August 12, 2014Assignee: NPC Industrias Quimicas LtdaInventors: Milton Sobrosa Cordeiro, Sérgio Teixeira, Ariovaldo Fernandes Junior
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Publication number: 20140194635Abstract: 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: January 16, 2014Publication date: July 10, 2014Applicant: REG Seneca, LLCInventors: John P. Jackam, Joel M. Pierce, Jeffrey D. Jones
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Patent number: 8765985Abstract: Blown corn stillage oils and methods for making blown corn stillage oils are disclosed. In one aspect the corn stillage oils are stripped to reduce the acid value of the resulting blown, stripped corn stillage oil. The method includes heating a corn stillage oil to a temperature of at least 90° C., and passing air through the heated oil to produce a blown corn stillage oil having a viscosity of at least 50 cSt at 40° C. In one aspect, the blown corn stillage oil is stripped to reduce the acid value of the blown, stripped corn stillage oil to 5 mg KOH/gram or less.Type: GrantFiled: May 21, 2010Date of Patent: July 1, 2014Assignee: Cargill, IncorporatedInventors: Michael John Hora, Frank P. Lochel
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Patent number: 8754247Abstract: 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: GrantFiled: July 21, 2009Date of Patent: June 17, 2014Assignee: IFP Energies nouvellesInventors: Amandine Cabiac, Nicolas Cadran, Emmanuelle Guillon, Vincent Lecocq, Sylvie Maury
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Patent number: 8728177Abstract: 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: May 20, 2014Assignee: Seneca Landlord, L.L.C.Inventors: John P. Jackam, Joel M. Pierce, Jeffrey D. Jones
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Publication number: 20140121394Abstract: Esters of 2-propylheptanol with linear or branched, saturated or unsaturated C5-C36 carboxylic acids and C4-C36 dicarboxylic acids, compositions comprising these esters, and to the use of esters of 2-propylheptanol with linear or branched, saturated or unsaturated C5-C35-carboxylic acids and/or C4-C36-dicarboxylic acids in cosmetic and/or topical pharmaceutical preparations.Type: ApplicationFiled: January 7, 2014Publication date: May 1, 2014Applicant: Cognis IP Management GmbHInventors: Markus Dierker, Catherine Weichold, Stefanie Althaus, Lars Zander, Daniela Prinz
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Patent number: 8703849Abstract: 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: GrantFiled: January 4, 2011Date of Patent: April 22, 2014Assignee: Archer Daniels Midland CompanyInventors: Erik Hagberg, Stephen Howard, George Poppe, Stephen D. Horton