Esterification Of Fatty Material To Reduce The Amount Of Free Fatty Acid Or To Facilitate Separation Of Constituents Patents (Class 554/174)
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Patent number: 11590068Abstract: The invention relates to a personal care product for alleviating skin dryness, includes facial skin dryness, breast skin dryness and vulval dryness and for restoring vaginal flora, acidic pH in the vagina, and vaginal health. Embodiments of the personal care product include a formulation including at least about 83 wt. % plant-based glycerides; from about 0.05 wt. % to about 0.15 wt. % sodium hyaluronate; and from about 0.01 wt. % to about 1.5 wt. % sea buckthorn powder. Another embodiment includes a personal care product including at least 55 wt. % plant-based glycerides and from about 20 wt. % to about 42 wt. % sucrose. The personal care product may also include shea olein. The person care product is substantially free of added water, alcohol, synthetic chemical, anti-microbial agent, and synthetic hormone.Type: GrantFiled: April 10, 2018Date of Patent: February 28, 2023Assignee: DAMIVA INC.Inventors: Gardiner F. H. Smith, Chia Chia Sun
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Patent number: 11459280Abstract: The present invention relates to a process for the production of olefinic compounds that can be used for the production of detergents, additives, lubricants and/or plastic materials, or components which can be used in the field of oil explorations and productions, and a hydrocarbon fuel or a fraction thereof, which comprises subjecting a mixture of glycerides having at least one unsaturated hydrocarbon chain, to metathesis reaction and, after separating the olefinic mixture obtained, effecting a hydrodeoxygenation and subsequently hydroisomerization process, so as to obtain the hydrocarbon fuel or a fraction thereof.Type: GrantFiled: February 12, 2021Date of Patent: October 4, 2022Assignee: versalis S.p.A.Inventors: Aldo Bosetti, Sergio Francantonio Lombardini, Gianni Girotti
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Patent number: 11124715Abstract: The present invention relates to a method of producing biohydrocarbons. Further, the invention relates to biohydrocarbons obtainable by the methods of the invention and to a method of producing polymers.Type: GrantFiled: May 18, 2016Date of Patent: September 21, 2021Assignee: NESTE OYJInventors: Maija Hakola, Tomi Nyman
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Patent number: 11078427Abstract: A process for producing crude biodiesel from renewable feedstocks (such as fats, oils, and greases) containing unsaponifiable materials; purifying the crude biodiesel through a purification process; recovering a purified biodiesel distillate stream and a less volatile biodiesel residue stream; and further recovering valuable chemicals from the biodiesel residue. Specifically, the present technology relates to the concentration of valuable chemicals in the biodiesel residue product of biodiesel production and the subsequent recovery of these valuable chemicals. The process may further include the conversion of the biodiesel residue into diesel range hydrocarbons using hydrodeoxygenation and the subsequent purification of the hydrocarbon fraction produced thereby.Type: GrantFiled: May 1, 2019Date of Patent: August 3, 2021Assignee: Renewable Energy Group, Inc.Inventors: James Matthew White, David A. Slade, Martin R. Haverly, Ramin Abhari, Cody J. Ellens
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Patent number: 10906861Abstract: Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.Type: GrantFiled: April 3, 2015Date of Patent: February 2, 2021Assignee: Wilmar Trading Pte LtdInventors: Timothy W. Abraham, Hiroki Kaido, Choon Woo Lee, Richard L. Pederson, Yann Schrodi, Michael John Tupy
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Patent number: 10889772Abstract: Methods are provided for accurately blending biodiesel into distillate streams to achieve a pre-determined percentage of biodiesel in the distillate, applicable to wild-type distillate streams as well as distillate streams that already contain some percentage of biodiesel.Type: GrantFiled: February 1, 2018Date of Patent: January 12, 2021Assignee: Texon LPInventors: Robert Fransham, Colin Robbins
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Patent number: 10683464Abstract: This disclosure relates to ester compounds derived from neo-acids, lubricating oil base stocks comprising such ester compounds, lubricating oil compositions comprising such ester compounds, and method for making such compounds and/or base stocks. The lubricating oil base stocks comprising the ester compounds exhibit desirable lubricating properties such as polarity and oxidation stability.Type: GrantFiled: July 11, 2018Date of Patent: June 16, 2020Assignee: ExxonMobil Chemical Patents Inc.Inventors: Abhimanyu O. Patil, Kyle G. Lewis, Satish Bodige
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Patent number: 10590061Abstract: 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: April 9, 2018Date of Patent: March 17, 2020Assignee: BENEFUEL, INC.Inventors: William A. Summers, Rebecca Williams, Danny Gulledge, Robert Barrie Tripp
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Patent number: 10351886Abstract: Facile methods for high-yield furfural and HMF production from biomass sugars are described. The methods generally involve converting the biomass sugars in high yield to their ketose isomers, resulting in furan production under low temperature and pressure conditions with efficient recycling of the process streams.Type: GrantFiled: November 27, 2017Date of Patent: July 16, 2019Assignee: The University of ToledoInventors: Siamak Alipour, Bin Li, Sasidhar Varanasi, Patricia Relue, Sridhar Viamajala
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Patent number: 10150749Abstract: Disclosed is a continuous process for concentrating or separating of vitamin E, sterols and/or terpenes from oily or fatty mixtures of biological origin comprising the measures: a) providing a reaction mixture containing oily or fatty mixture of biological origin, at least a monohydric alcohol and at least an acidic catalyst, b) continuously conducting the reaction mixture through a reactor which has a heating zone in which the reaction mixture is heated to a temperature between 100° C. and 190° C.Type: GrantFiled: May 29, 2015Date of Patent: December 11, 2018Assignee: WeylChem Wiesbaden GmbHInventors: Roman Morschhäuser, Said Kchirid, Hans Jürgen Scholz
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Patent number: 10035971Abstract: In the present invention a method for treating algae is disclosed, which method comprises the steps of (a) providing an ionic liquid, which is a conjugate of an organic base with pKa at least 6 and an acid, (b) providing algae, (c) subjecting algae to cell lysis with the ionic liquid, whereby at least two phases are formed, including a hydrophobic phase and a hydrophilic phase, and (d) separating the hydrophobic phase containing lipids.Type: GrantFiled: May 11, 2015Date of Patent: July 31, 2018Assignee: STAMICARBON B.V.Inventors: Cinzia Chiappe, Christian Pomelli, Andrea Mezzetta, Barbara Masciocchi, Alessio Gentile
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Patent number: 9826757Abstract: The present invention describes a method and an automatic system for recovering protein powder meal, crude and pure omega-3 oil and purified distilled water from a mixture of animal tissue processed in a filter-drier-reaction tank. Animal tissue, for example fish, and organic solvent are directly or indirectly fed into the filter-drier-reaction tank. The filter-drier-reaction tank mixes, heats, and separates solid and heavy liquid portions of the mixture, the organic solvents are automatically recycled back in to the system after distillation. The solid portion is retained in the filter-drier-reaction tank and baked. Solid protein powder product (the protein powder meal) is thus recovered.Type: GrantFiled: October 11, 2013Date of Patent: November 28, 2017Assignee: Advance International Inc.Inventors: Shahmard Maziar Ghorbani, Kerry Coltun
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Patent number: 9352292Abstract: The invention relates to an arrangement for feeding heat-sensitive feedstock to a fixed-bed reactor system comprising means for product recycle and a fixed-bed reactor system comprising a fixed-bed reactor comprising at least one reaction zone having at least one catalyst bed and said reaction zone comprising a cold feed distributor arranged on top of each catalyst bed and a conventional distributor arranged above each cold feed distributor. Also a method is provided for feeding heat-sensitive feedstock to a fixed-bed reactor system wherein said fixed-bed reactor system comprises means for product recycle and a fixed-bed reactor comprising at least one reaction zone having at least one catalyst bed and said reaction zone comprising a cold feed distributor arranged on top of each catalyst bed and a conventional distributor arranged above each cold feed distributor.Type: GrantFiled: January 13, 2012Date of Patent: May 31, 2016Assignee: NESTE OYJInventors: Juha Solantie, Kari J. Koivisto
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Patent number: 9328054Abstract: At least one of transesterification, esterification and hydrolysis can occur with a method as shown and described herein. Preferably pressures are lower than supercritical pressures for the alcohol employed and the conversion rate is at least 95%, if not 99% in a single reactor which may be counter or co-flow or even a batch process. Meanwhile, bound glycerin may be separated from alkyl esters for at least some processes.Type: GrantFiled: September 26, 2014Date of Patent: May 3, 2016Inventors: Travis Danner, Philip N. Brown, Mark Mauss
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Patent number: 9328303Abstract: A method is provided involving reducing a pressure drop across a hydroprocessing reactor having a reactor feed and producing a hydroprocessing product, where the reactor feed includes a bio-oil feed and a hydrocarbon diluent; and the step of reducing the pressure drop comprises stopping or substantially reducing the bio-oil feed supplied to the reactor and supplying the hydrocarbon diluent to the reactor with a mass flux of at least about 1,000 lb/hr/ft2.Type: GrantFiled: March 13, 2013Date of Patent: May 3, 2016Assignee: REG SYNTHETIC FUELS, LLCInventors: Ramin Abhari, Peter Havlik, H. Lynn Tomlinson, Gary Roth, Tsungani Record
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Patent number: 9228154Abstract: The present invention provides a robust and efficient process for reducing the cloud point of biodiesel fuel in which clathrates are formed from saturated fatty acid components as solvent is evaporated from a mixture of urea, methanol and fatty acid esters. The process speed can be fast, and is governed by the speed with which urea can be brought into clathrate forming contact with the fatty acid esters in the first instance, and then by the speed that solvent can be evaporated. Advantageously, substantially all of the solvent can be evaporated as pure solvent, which enhances process efficiencies and reduces cost. Additionally, substantially all of the urea can be used to form clathrates, further maximizing process efficiency.Type: GrantFiled: November 27, 2013Date of Patent: January 5, 2016Assignee: Purdue Research FoundationInventors: Bernard Y. Tao, Samia Mohtar
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Patent number: 9145527Abstract: Disclosed is a method for preparing high purity biodiesel from crude oils. The method comprises the steps of: pre-treating the crude oil raw material to remove impurities; pre-esterifying the pre-treated crude oil raw material under the effect of a catalyst of concentrated sulfuric acid; and then carrying out an ester exchange reaction in the presence of an alkali catalyst; recycling methanol, and separating glycerol, so as to obtain a crude fatty acid methyl ester; and subjecting the obtained fatty acid methyl ester to purification, distillation and segmentation to obtain a high-purity fatty acid methyl ester.Type: GrantFiled: August 9, 2012Date of Patent: September 29, 2015Assignee: BEIJING QINGYANLIHUA PETROLEUM CHEMISTRY CO., LTD.Inventor: Xinuo Lu
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Patent number: 9090845Abstract: Process for producing high-yield biodiesel applying high acidity triglycerides with generation of glycerin 90% free of salts starting from fatty lower cost fatty material allied with an esterification and innovative extraction process that generates a further value, more specifically for the production of biodiesel.Type: GrantFiled: January 23, 2013Date of Patent: July 28, 2015Assignee: GLYCEROSOLUTION QUIMICA LTDAInventors: Hiromu Nishiama, Silvio Antonio Cazzolato, Matheus Marchi dos Santos Silva
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Patent number: 8993793Abstract: The present invention provides bifunctional silica mesoporous materials, including mesoporous silica nanoparticles (“MSN”), having pores modified with diarylammonium triflate and perfluoroaryl moieties, that are useful for the acid-catalyzed esterification of organic acids with organic alcohols.Type: GrantFiled: January 30, 2012Date of Patent: March 31, 2015Assignee: Iowa State University Research Foundation, Inc.Inventors: Chih-Hsiang Tsai, Hung-Ting Chen, Marek Pruski, Takeshi Kobayashi, Show-Ling Lee
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Patent number: 8936923Abstract: The invention relates to the production of biodiesel feedstock and biodiesel. A process for producing a biodiesel utilizing a thraustochytrid is provided.Type: GrantFiled: December 5, 2007Date of Patent: January 20, 2015Assignee: Biomass Research & Refining Pty LtdInventors: Lindsay Fisher, David Nicholls, Kevin Sanderson
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Patent number: 8895765Abstract: A method for preparing fatty acid alkyl ester for bio-diesel fuel is disclosed wherein fatty acid, specifically fatty acid distillate reacts with alcohol. The method does not require the glycerin purification process, and has the superior conversion ratio of fatty acid. The method for preparing fatty acid alkyl ester for bio-diesel fuel comprises the step of carrying out a counter current type esterification reaction of fatty acid and alcohol in each tray of a counter current column reactor at a temperature of 200 to 350° C. and a pressure of 1 to 35 bar. Here the raw material of the fatty acid is fed to an upper part of the counter current column reactor and the alcohol is fed to a lower part of the counter current column reactor. The counter current column reactor has a number of trays which are installed horizontally to have a number of vertical compartments. Each of the number of trays has an opening part at one end thereof to communicate one compartment with an adjoining compartment.Type: GrantFiled: September 22, 2009Date of Patent: November 25, 2014Assignee: SK Chemicals Co., Ltd.Inventors: Soo-Hyun Kim, Hyun-Jun Cho, Chan-Woo Moon, Byoung-Kyung Ham, Jae-Bong Lim
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Patent number: 8871960Abstract: Methods to convert unsaturated fatty acids derived from biobased oils to highly functionalized esters, ester polyols, amides, and amide polyols. The products can be used to make polyurethane and polyester films and foams.Type: GrantFiled: December 31, 2009Date of Patent: October 28, 2014Assignee: Battelle Memorial InstituteInventors: Herman Paul Benecke, Daniel B. Garbark
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Patent number: 8870980Abstract: The present invention relates to a process for producing enzymes and single cell oil. The process comprises that microorganisms capable of producing both single cell oil and enzymes are cultivated under conditions suitable for single cell oil production and enzyme production in a single cell oil production process. A microorganism culture comprising single cell oil and enzymes is obtained and at least part of the microorganism culture, of the supernatant and/or microorganism cells separated from the microorganism culture, of protein fraction enriched from the supernatant, and/or of protein fraction obtained from the cells is used as an enzyme preparation or as a source of enzymes. Single cell oil is recovered from the microorganism cells and used as biofuel, component of biofuel or as a starting material for biofuel production. Enzymes produced according to the process are used in the same or in another industrial process.Type: GrantFiled: December 21, 2011Date of Patent: October 28, 2014Assignee: Neste Oil OyjInventors: Annika Malm, Simo Laakso, Ossi Pastinen, Heidi Kahelin, Miia Mujunen
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Patent number: 8816106Abstract: The present invention relates to enzymes which possess desaturase, conjugase, epoxidase and/or hydroxylase activity that can be used in methods of synthesizing fatty acids.Type: GrantFiled: August 29, 2007Date of Patent: August 26, 2014Assignees: Commonwealth Scientific and Industrial Research Organisation, Grains Research and Development CorporationInventors: Katherine Damcevski, Karen Glover, Allan Green, Victoria S. Haritos, Irene Horne, Surinder Pal Singh, Craig C. Wood, Xue-Rong Zhou
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Patent number: 8809025Abstract: A method for culturing algae comprising, forming an emulsion comprising a gaseous stream and a media utilizing a high shear device, wherein the emulsion comprises gas bubbles, and wherein the high shear device comprises at least one toothed rotor and at least one stator; introducing the emulsion into a bioreactor; and introducing an algae into the bioreactor for growing the algae culture. Additionally, a method for producing liquids from an algae culture, the method comprising forming an emulsion comprising a buffer and algal components, wherein the emulsion comprises algal component globules; separating algal hydrocarbons; and processing algal hydrocarbons to form liquid hydrocarbons. Additionally, a system for producing liquids from an algae culture comprising at least one high shear device.Type: GrantFiled: October 6, 2010Date of Patent: August 19, 2014Assignee: H R D CorporationInventors: Abbas Hassan, Aziz Hassan, Rayford G. Anthony, Gregory G. Borsinger
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Patent number: 8802878Abstract: A process for producing fatty acid methyl esters includes mixing an alcohol with a feedstock oil to prepare an alcohol/oil mixture, then reacting the alcohol/oil mixture using a first heterogeneous catalyst in an acid esterification process to produce a glycerin-containing product. The glycerin is separated from the glycerin-containing product using a coalescer to produce a biodiesel-containing feedstock and glycerin. Biodiesel is separated from the biodiesel-containing feedstock using a coalescer to produce unreacted feedstock and biodiesel. The unreacted feedstock is reacted using a second heterogeneous catalyst in a trans-esterification process to produce a glycerin-biodiesel-methanol mixture. Biodiesel and glycerin are separated in separate streams from the glycerin-biodiesel-methanol mixture, using a coalescer, to produce additional glycerin and additional biodiesel.Type: GrantFiled: September 14, 2011Date of Patent: August 12, 2014Inventor: Kyent Chin
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Patent number: 8741145Abstract: A method for producing biofuels is provided. A method of making biofuels includes dewatering substantially intact algal cells to make an algal biomass, extracting neutral lipids from the algal biomass, and esterifying the neutral lipids with a catalyst in the presence of an alcohol. The method also includes separating a water soluble fraction comprising glycerin from a water insoluble fraction comprising fuel esters and distilling the fuel esters under vacuum to obtain a C16 or shorter fuel esters fraction, a C16 or longer fuel ester fraction, and a residue comprising carotenoids and omega-3 fatty acids. The method further includes hydrogenating and deoxygenating at least one of (i) the C16 or shorter fuel esters to obtain a jet fuel blend stock and (ii) the C16 or longer fuel esters to obtain a diesel blend stock.Type: GrantFiled: September 30, 2011Date of Patent: June 3, 2014Assignee: Heliae Development, LLCInventor: Aniket Kale
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Patent number: 8715980Abstract: Described are methods of cultivating autotrophic microorganisms, particularly microalgae or diatoms, in a bioreactor by entraining a culture of the microorganisms in a tenuous, gelated, thixotrophic carrier medium having nutrients therefor and moving the medium along a passage at a sufficiently slow speed to enable laminar flow which in cross section is closed and which has transparent walls through which the culture is irradiated to enable photosynthesis. The method includes effecting convective turnover of the culture and medium as they flow along the passage by differentially heating the medium laterally relative to the flow direction so as to produce a generally helical flow of the culture and medium. Also described are processing methods, both physical and chemical, performed underground e.g.Type: GrantFiled: December 10, 2010Date of Patent: May 6, 2014Assignee: Winwick Business Solutions Pty LtdInventor: William Severn Clarke
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Patent number: 8709109Abstract: A process for preparing biodiesel having improved filterability characteristics including inducing transesterification of a triglyceride feedstock with cavitation to form an intermediate reaction product. Glycerol by product is separated from the intermediate reaction product before finishing the transesterification reaction in a pressurized reaction tank to yield a biodiesel reaction product. The biodiesel reaction product can be further purified by removing glycerol.Type: GrantFiled: January 11, 2010Date of Patent: April 29, 2014Assignee: Arisdyne Systems IncorporatedInventors: Oleg Kozyuk, Peter Reimers, Paul A. Reinking
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Patent number: 8673028Abstract: A method of producing a biodiesel from a wet biomass is provided. The method includes providing the wet biomass that includes water and biomass solids. The method also includes heating the wet biomass at a first temperature and a first pressure for a time period ranging from 10 to 480 minutes to form an aqueous solution and a solid agglomerate containing a hydrolyzed lipid component. The method also includes step of transesterifying the hydrolyzed lipid component to form biodiesel.Type: GrantFiled: September 2, 2011Date of Patent: March 18, 2014Assignee: The Regents of the University of MichiganInventors: Phillip E. Savage, Robert Levine, Tanawan Pinnarat
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Patent number: 8637056Abstract: Mixture comprising esters of saturated C16-C18 fatty acid and unsaturated C16-C18 fatty acids with 2-ethyl-hexyl alcohol, said esters being in an amount ranging from 90% to 100% by weight with respect to the total weight of the mixture. The cosmetic compositions containing such a mixture formulated in topical form have a moisturizing, emollient, elasticizing and skin compactness and smoothness improving action.Type: GrantFiled: October 15, 2009Date of Patent: January 28, 2014Assignee: Hallstar Italia S.R.L.Inventors: Sergio Amari, Edoardo Pallucca
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Patent number: 8637689Abstract: Provided herein are processes for preparing estolides and estolide base oils from fatty acid reactants utilizing catalysts. Further provided herein are processes for preparing carboxylic esters from at least one carboxylic acid reactant and at least one olefin.Type: GrantFiled: August 31, 2011Date of Patent: January 28, 2014Assignee: Biosynthetic Technologies, LLCInventors: Jakob Bredsguard, Jeremy Forest, Travis Thompson
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Patent number: 8629291Abstract: Process and steps for the production of biodiesel and/or glycerin from feedstock are provided.Type: GrantFiled: November 27, 2012Date of Patent: January 14, 2014Assignee: Menlo Energy Management, LLCInventors: Gaurav Shah, Sunil Suri
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Patent number: 8624073Abstract: Non-basic and non-acidic homogeneous catalysts organo-metallic compound of the formula: M(OCH3)x wherein M is B, Na, Mg, K, Ca, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Ga, Ge, Al, Sn, Sb, Mo, Ag, and Cd and x is an integer from 2, 3 or 4 can catalyze transesterification of oils and fats having high free fatty acid content and with an acid number from 0.5 to 20, into biodiesel. B(OCH3)3 and Ge(OCH3)4, having low boiling points, are easily recovered from the biodiesel and glycerol phases and recycled for reuse. Continuous biodiesel production with the novel homogenous catalysts is achieved without the complicated and troublesome steps attendant with conventional processes using base or acid homogeneous catalyst. The high purity biodiesel is produced without acid-base neutralization, water wash, filtration, and solid disposal steps for removing the spent catalyst from the product streams associated with prior techniques.Type: GrantFiled: February 5, 2013Date of Patent: January 7, 2014Assignee: CPC Corporation, TaiwanInventors: Shih-Chieh Yang, Jen-Ray Chang, Maw-Tien Lee, Tzong-Bin Lin, Fu-Ming Lee, Cheng-Tsung Hong, Jeng-Cheng Lee
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Patent number: 8617866Abstract: Disclosed is an enzymatic process for the preparation of fatty acid alkyl esters, particularly fatty acids methyl esters (biodiesel) in a solvent-free microaqueous system, from a fatty acid source and an alcohol or alcohol donor, employing a robust lipase preparation that comprises at least two lipases separately or jointly immobilized on a suitable support, where one of the lipases has increased affinity to partial glycerides, another is sn-1,3 positional specific, and an optional third lipase has high selectivity towards sn-2 position of the glycerol backbone of the fatty acid source.Type: GrantFiled: November 13, 2008Date of Patent: December 31, 2013Inventors: Sobhi Basheer, Maisa Haj, Muhammad Kaiyal
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Patent number: 8603198Abstract: 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: GrantFiled: June 22, 2010Date of Patent: December 10, 2013Assignee: Cavitation Technologies, Inc.Inventors: Roman Gordon, Igor Gorodnitsky, Varvara Grichko
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Patent number: 8598378Abstract: Methods and compositions are disclosed for the direct transesterification and extraction of bio-lipids and bio-oils in the production of biofuel, particularly fatty acid methyl ester products.Type: GrantFiled: March 13, 2009Date of Patent: December 3, 2013Assignee: University of HawaiiInventors: Michael J. Cooney, Gregory Young
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Patent number: 8592613Abstract: The present invention relates to a method for producing fatty acid alkyl esters as well as cellulosic simplified sugars, shortened protein polymers, amino acids, or combination thereof resulting from the simultaneous esterification and hydrolysis, alcoholysis, or both of algae and other oil containing materials containing phospholipids, free fatty acids (FFA), glycerides, or combination thereof as well as polysaccharides, cellulose, hemicellulose, lignocellulose, protein polymers, or combination thereof in the presence of an alcohol and an optional acid catalyst.Type: GrantFiled: February 1, 2011Date of Patent: November 26, 2013Assignee: Inventure Renewables, Inc.Inventors: William W. Berry, Mark G. Tegen, William Rusty Sutterlin
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Patent number: 8580986Abstract: Disclosed is an improved process for the production of fatty acid lower alkyl esters according to formula (I) R1CO—OR2??(I) in which R1CO represents a linear or branched acyl moiety having from about 6 to about 22 carbon atoms and 0 to 6 double bonds and wherein R2 is a linear or branched alkyl moiety having 1 to 6 carbon atoms, by transesterification of triglycerides or fatty acid esters using C1-C6 aliphatic alcohols, which includes the steps of (a) providing an aqueous mixture of aliphatic C1-C6 alcohol by fermenting in a first reactor a carbon source comprising carbohydrates and/or glycerol produce a fermentation broth comprising said aliphatic C1-C6 alcohol, (b) providing in a second reactor a triglyceride and/or an ester of a fatty acid, together with a biocatalyst capable of effecting a transesterification reaction, (c) transferring said aqueous aliphatic C1-C6 alcohol mixture obtained from said first reactor into said second reactor to provide a two-phase system, and (d) effecting the transesteriType: GrantFiled: May 16, 2007Date of Patent: November 12, 2013Assignee: Cognis IP Management GmbHInventors: Eric Dubreucq, Albrecht Weiss, Bernhard Gutsche, Bernd Fabry, Guy Moulin
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Patent number: 8558022Abstract: A process results in oligomerized ester alkoxylate compositions having substantially no unsaturation, which may be useful as lubricants, heat transfer fluids, plasticizers, thickening agents, surfactants, or power transmission fluids. The steps include, in either order, oligomerization of a hydroxylated fatty acid or fatty ester and quantitative reaction of unreacted carboxylic acid or ester groups with an alcohol, with the product of either reaction then being alkoxylated in the presence of a double metal cyanide catalyst. These oligomerized ester alkoxylates may be derived from vegetable oils to ensure high levels of renewable carbons. The compositions may exhibit desirably high viscosity index, low pour point, and high levels of renewable carbons.Type: GrantFiled: April 7, 2011Date of Patent: October 15, 2013Assignee: Dow Global Technologies LLCInventors: Daniele Vinci, Jochem Kersbulck
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Patent number: 8545703Abstract: Process and steps for the production of biodiesel and/or glycerin from feedstock are provided.Type: GrantFiled: November 27, 2012Date of Patent: October 1, 2013Assignee: Menlo Energy Management, LLCInventors: Gaurav Shah, Sunil Suri
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Patent number: 8540881Abstract: Process and steps for the production of biodiesel and/or glycerin from feedstock are provided.Type: GrantFiled: November 27, 2012Date of Patent: September 24, 2013Assignee: Menlo Energy Management, LLCInventors: Gaurav Shah, Sunil Suri
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Patent number: 8535397Abstract: Process for the extraction of fatty acids from algal biomass comprising: producing an aqueous suspension of algal biomass; subjecting the aqueous suspension of algal biomass to acid hydrolysis and extraction by the addition of at least one non-polar organic solvent and at least one inorganic acid to said aqueous suspension of algal biomass, so as to obtain the following three phases: (i) a semisolid phase comprising a slurry of the algal biomass; (ii) an aqueous phase comprising inorganic compounds and hydrophilic organic compounds; (iii) an organic phase comprising fatty acids and hydrophobic organic compounds other than said fatty acids.Type: GrantFiled: June 19, 2009Date of Patent: September 17, 2013Assignee: ENI S.p.A.Inventors: Ezio Nicola D'Addario, Federico Capuano, Edoardo D'Angeli, Roberto Medici
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Patent number: 8536357Abstract: The invention relates to a process for esterifying free fatty acids in vegetable and animal fat with alcohols over heterogeneous acidic ion exchange resin catalysts at temperatures of 60 to 120° C.Type: GrantFiled: January 30, 2009Date of Patent: September 17, 2013Assignee: Bayer Technology Services GmbHInventors: Wulf Dietrich, Dieter Heinz, Leslaw Mleczko, Shaibal Roy, Heinrich Morhenn, Robert Tyron Hanlon
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Patent number: 8530683Abstract: A method of obtaining a solid component rich in a petroselinic compound from the seed of a plant of the Apiaceae or Araliaceae families, the method comprising: (a) treating a portion of the seed of the plant with an extraction solvent; and (b) inducing formation of the solid component.Type: GrantFiled: December 22, 2008Date of Patent: September 10, 2013Assignee: Bangor UniversityInventors: Mark Stephen Baird, David Preskett
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Patent number: 8530684Abstract: A method for preparing fatty acid alkyl ester for bio-diesels is disclosed, wherein fatty acid, specifically fatty acid distillate reacts with alcohol in the presence of metal catalyst instead of conventional acid or solid acid catalyst. The method does not require the glycerin purification process, and has the superior conversion ratio of fatty acid. The method for preparing fatty acid alkyl ester comprises the step of carrying out an esterification reaction of fatty acid raw material with alcohol in the presence of metal catalyst. Preferably, the esterification reaction is carried out at the temperature of 200 to 350° C. and the pressure of atmospheric pressure to 10 bar, and the metal catalyst is a compound containing metal selected from the group consisting of cobalt, iron, manganese, zinc, titanium and mixture thereof.Type: GrantFiled: April 1, 2008Date of Patent: September 10, 2013Assignee: SK Chemicals Co., Ltd.Inventors: Hyun-Jun Cho, Byung-Hui Kim, Soo-Hyun Kim, Yong-Jun Shin, Shin-ho Chun
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Patent number: 8491857Abstract: 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: September 5, 2012Date of Patent: July 23, 2013Inventor: Antonio Cantizani
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Patent number: 8475542Abstract: A method for producing a fuel or fuel additive comprising providing a reaction mixture comprising oil and an alcohol in an oil-in-alcohol emulsion and a catalyst for converting the oil to the fuel or the fuel additive. The oil and the alcohol are reacted in the presence of the catalyst, at a concentration below that used in a conventional batch process, to produce the fuel or fuel additive. This low level of catalyst reduces the formation of diols and oxidation products that can diminish the quality of the fuel or fuel additive. The fuel or fuel additive produced is continuously removed during the reaction, effectively de-coupling the concentration of catalyst used from the rate of the two phase reaction.Type: GrantFiled: May 13, 2010Date of Patent: July 2, 2013Assignee: University of Ottawa Technology Transfer and Business EnterpriseInventors: André Yves Tremblay, Marc Arnold Dubé, Peigang Cao
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Patent number: 8466304Abstract: The present invention describes a method of producing fatty acid alkyl esters and glycerin implementing a set of transesterification reactions between a vegetable or animal oil and an aliphatic monoalcohol in the presence of a heterogeneous solid catalyst so as to obtain an effluent comprising at least alkyl esters, free glycerol, bonded glycerol and alcohol, wherein at least one stage of separation of at least a portion of the effluent is carried out in order to separate the ester produced and the bonded glycerol, said separation occurring through a membrane.Type: GrantFiled: December 22, 2009Date of Patent: June 18, 2013Assignee: IFP Energies NouvellesInventors: Arnaud Baudot, Laurent Bournay, Eszter Toth
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Patent number: 8449629Abstract: The present invention relates to a process and apparatus for the production of carboxylic acid esters and/or biodiesel fuel from feedstocks containing fatty acids, glycerated fatty acids, and glycerin by reactive distillation. Specifically, in one embodiment, the present invention relates to the production of biodiesel fuels having low glycerin, water, and sulfur content on an industrial scale.Type: GrantFiled: December 9, 2011Date of Patent: May 28, 2013Assignee: Endicott Biofuels II, LLCInventor: William Douglas Morgan