Another Reactant Contains Alcoholic Or Phenolic Hydroxy Patents (Class 554/170)
  • Patent number: 11359163
    Abstract: The use of hypophosphorous acid as a corrosion inhibitor for esterification reactions of free fatty acids contained in a fatty substance is described, particularly in the presence of an organosulfonic acid. The invention also relates to a method for the esterification of fatty acids.
    Type: Grant
    Filed: April 19, 2019
    Date of Patent: June 14, 2022
    Assignee: Arkema France
    Inventor: Jean-Alex Laffitte
  • Patent number: 10752573
    Abstract: This invention relates to a process for the continuous production of a (meth)acrylic ester by transesterification reaction between a C1-C4 light alkyl (meth)acrylate, with a heavy alcohol in the presence of a catalyst, characterised in that the flows feeding the reactor are introduced through a static mixer placed on a recirculation loop of the reactor. The use of a static mixer improves the selectivity of the reaction and consequently the overall productivity of (meth)acrylic ester synthesis process.
    Type: Grant
    Filed: December 7, 2017
    Date of Patent: August 25, 2020
    Assignee: Arkema France
    Inventors: Fanny Dubut, Marc Esch, Coralie Graire, Benoit Riflade
  • Patent number: 10544381
    Abstract: Embodiments herein relate to the production of alkyl esters from acidified soap stock. In an embodiment, a process for producing alkyl esters is provided. The process can include mixing acidified soap stock with an alcohol, water, carbon dioxide, and/or carbon monoxide, to form a reaction mixture, and contacting the reaction mixture with a catalyst under supercritical conditions for the alcohol, the catalyst including a metal oxide. Other embodiments are also included herein.
    Type: Grant
    Filed: February 7, 2019
    Date of Patent: January 28, 2020
    Assignee: SarTec Corporation
    Inventors: Charles Vincent McNeff, Clayton V. McNeff, Larry C. McNeff, Bingwen Yan
  • Patent number: 10442824
    Abstract: Disclosed is a method for producing a titanium containing catalyst, wherein the catalyst includes one or more titanium alpha-hydroxy carboxylate species, e.g., titanium citrate, and one or more titanium oxide species, e.g., TiOx, wherein x is greater than 0 and less than or equal to 2, wherein the sum of all of the above titanium oxide species relative to the sum of all titanium alpha-hydroxy carboxylate species in the titanium containing catalyst is greater than 0 but less than 1.00 mol.-%. The method of production involves, for example, reacting tetraisopropyl orthotitanate with an aqueous solution of citric acid, and removing the byproduct of 2-propanol by distillation. Also disclosed is a method for the production of polyesters by the use of the catalyst.
    Type: Grant
    Filed: January 31, 2014
    Date of Patent: October 15, 2019
    Assignees: UHDE INVENTA-FISCHER GMBH, CATALYTIC TECHNOLOGIES LIMITED
    Inventors: Matthias Schoennagel, Alan Thomas Cooper
  • Patent number: 9562135
    Abstract: This invention relates to a process for preparation of polyether alkoxylated carbonates. These products may also be referred to as polyether polycarbonates. This process simultaneously transcarbonates and alkoxylates a mixture of one or more carbonate compounds, and one more hydroxyl group containing compounds, with at least one alkylene oxide in the presence of a mixture of catalysts. The catalyst mixture contains at least one DMC catalyst and at least one non-alkaline transesterification catalyst. This invention also relates to novel polyether polycarbonates, a process for preparing polyurethane foams from these novel polyether polycarbonates and to foams comprising these novel polyether polycarbonates.
    Type: Grant
    Filed: December 21, 2015
    Date of Patent: February 7, 2017
    Assignee: Covestro LLC
    Inventor: Kenneth G. McDaniel
  • Patent number: 9284512
    Abstract: Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.
    Type: Grant
    Filed: February 23, 2015
    Date of Patent: March 15, 2016
    Assignee: Elevance Renewable Sicences, Inc.
    Inventors: Thomas E. Snead, Steven A. Cohen, Demond L. Gildon
  • Patent number: 9115325
    Abstract: Methods, systems, and devices are disclosed for producing, storing and using alcohol fuels. In one aspect of the disclosed technology, a method to provide a fuel for an engine includes mixing an alcohol with water to produce a wet alcohol, adding a fuel constituent in the wet alcohol to form a liquid fuel, the fuel constituent being soluble in the wet alcohol, and converting, in a container having an interior formed of an armored material, the liquid fuel into a gaseous fuel substance using at least one of heat energy or electrical energy to pressurize the liquid fuel, the gaseous fuel substance exhibiting a higher pressure and lower density than that of the liquid fuel.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: August 25, 2015
    Assignee: MCALISTER TECHNOLOGIES, LLC
    Inventor: Roy Edward McAlister
  • Patent number: 9000246
    Abstract: Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.
    Type: Grant
    Filed: October 9, 2012
    Date of Patent: April 7, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Thomas E. Snead, Steven A. Cohen, Demond L. Gildon
  • Patent number: 8993793
    Abstract: 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: Grant
    Filed: January 30, 2012
    Date of Patent: March 31, 2015
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: Chih-Hsiang Tsai, Hung-Ting Chen, Marek Pruski, Takeshi Kobayashi, Show-Ling Lee
  • Patent number: 8962873
    Abstract: 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: Grant
    Filed: March 7, 2012
    Date of Patent: February 24, 2015
    Assignee: Benefuel, Inc.
    Inventors: William A. Summers, Rebecca Williams, Danny Gulledge, Robert Barrie Tripp
  • Patent number: 8957231
    Abstract: An efficient and simple process to obtain a concentrate that includes over 80% in weight of ethyl esters of ?-3 fatty acids based on a composition of matter that contains esters of ?-3 fatty acids or free ?-3 fatty acids that comprises the stages of: a) contacting the composition of matter with ethanol of at least 96% in weight and a hydroxide of an alkali metal at a temperature between 60 and 200° C. to form a liquid mixture that includes alkaline salts of fatty acids; b) cool the liquid mixture to a temperature between 50 and ?20° C. to form a solid phase and a liquid phase and separate the liquid phase from the solid phase; c) contact the separated liquid phase of stage b) with an acid to form an acidified mixture with a water content under 10%, where the mixture consists of a solid phase that includes the alkali metal salt of the acid and a liquid phase that comprises ?-3 fatty acids; d) heat the mixture of stage c) between 50 to 150° C.
    Type: Grant
    Filed: December 25, 2011
    Date of Patent: February 17, 2015
    Assignee: Golden Omega S.A.
    Inventors: Juvenal Antonio Sepulveda Reyes, Miriam Rosa Berrios Cornejo, Miguel Angel Fuenzalida Dias, Alejandro Markovits Rojas, Thomas Francis Harting Glade
  • Patent number: 8957268
    Abstract: Methods are provided for refining natural oil feedstocks. The methods comprise reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters. In certain embodiments, the methods further comprise separating the olefins from the esters in the metathesized product. In certain embodiments, the methods further comprise hydrogenating the olefins under conditions sufficient to form a fuel composition. In certain embodiments, the methods further comprise transesterifying the esters in the presence of an alcohol to form a transesterified product.
    Type: Grant
    Filed: October 11, 2010
    Date of Patent: February 17, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Steven A. Cohen, Melvin L. Luetkens, Jr., Chander Balakrishnan, Robert Snyder
  • Patent number: 8946460
    Abstract: The present invention relates to a process for producing ethyl esters of polyunsaturated fatty acids, comprising transesterifying triacylglycerols in extracted plant lipid.
    Type: Grant
    Filed: June 14, 2013
    Date of Patent: February 3, 2015
    Assignees: Commonwealth Scientific and Industrial Research Organisation, Grains Research and Development Corporation, Nuseed Pty Ltd
    Inventors: James Robertson Petrie, Surinder Pal Singh, Robert Charles de Feyter
  • Patent number: 8895765
    Abstract: 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: Grant
    Filed: September 22, 2009
    Date of Patent: November 25, 2014
    Assignee: SK Chemicals Co., Ltd.
    Inventors: Soo-Hyun Kim, Hyun-Jun Cho, Chan-Woo Moon, Byoung-Kyung Ham, Jae-Bong Lim
  • Patent number: 8877952
    Abstract: Methods to pre-esterify primary polyols used in converting biobased oils, oil derivatives, and modified oils to highly functionalized esters, ester polyols, amides, and amide polyols.
    Type: Grant
    Filed: December 31, 2009
    Date of Patent: November 4, 2014
    Assignee: Battelle Memorial Institute
    Inventors: Herman Paul Benecke, Daniel B. Garbark, Bhima Rao Vijayendran
  • Patent number: 8859794
    Abstract: Methods to convert fatty acids to highly functionalized esters, ester polyols, amides, and amide polyols. The products can be used to make polyurethane and polyester films and foams.
    Type: Grant
    Filed: December 31, 2009
    Date of Patent: October 14, 2014
    Assignee: Battelle Memorial Institute
    Inventors: Herman Paul Benecke, Daniel B. Garbark, Bhima Rao Vijayendran
  • Patent number: 8846065
    Abstract: The present invention is directed to a mixture of esters according to the general formula (I), R1—C(?O)—O—R2, wherein R1 is an alkyl moiety with 5 to 11 carbon atoms and wherein R2 is a an alkyl moiety with 8 to 18 carbon atoms and wherein the mixture comprises 10 or less than 10 weight-% of ester of the general formula (I) wherein R1 is an alkyl moiety with 9 or more carbon atoms, based on the total amount of esters according to formula (I). The invention is further directed to cosmetic and/or pharmaceutical compositions comprising such esters as well as to processes for the production of such esters.
    Type: Grant
    Filed: June 19, 2010
    Date of Patent: September 30, 2014
    Assignee: Cognis IP Management GmbH
    Inventors: Marc Beuché, Francois Canonville, Valerie Pian
  • Patent number: 8802878
    Abstract: 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: Grant
    Filed: September 14, 2011
    Date of Patent: August 12, 2014
    Inventor: Kyent Chin
  • Patent number: 8729283
    Abstract: A method comprising providing a starting composition comprising a polyunsaturated fatty acid, a polyunsaturated fatty ester, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated triglyceride, or a mixture thereof; self-metathesizing the starting composition or cross-metathesizing the starting composition with at least one short-chain olefin in the presence of a metathesis catalyst to form self-/cross-metathesis products comprising: cyclohexadiene; at least one olefin; and one or more acid-, ester-, or salt-functionalized alkene; and reacting cyclohexadiene to produce at least one cycloalkane or cycloalkane derivatives.
    Type: Grant
    Filed: January 15, 2013
    Date of Patent: May 20, 2014
    Assignee: Energy & Environmental Research Center Foundation
    Inventor: Edwin S. Olson
  • Publication number: 20140121395
    Abstract: A chemical reaction apparatus includes a horizontal flow-type reactor in which a content horizontally flows with an unfilled space being provided thereabove, a microwave generator that generates microwaves, and at least one waveguide that transmits the microwaves generated by the microwave generator to the unfilled space in the reactor.
    Type: Application
    Filed: June 29, 2011
    Publication date: May 1, 2014
    Applicant: MICROWAVE CHEMICAL CO., LTD.
    Inventors: Akinori Ishizuka, Iwao Yoshino, Kunitaka Momota
  • Publication number: 20140121394
    Abstract: 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: Application
    Filed: January 7, 2014
    Publication date: May 1, 2014
    Applicant: Cognis IP Management GmbH
    Inventors: Markus Dierker, Catherine Weichold, Stefanie Althaus, Lars Zander, Daniela Prinz
  • Patent number: 8709109
    Abstract: 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: Grant
    Filed: January 11, 2010
    Date of Patent: April 29, 2014
    Assignee: Arisdyne Systems Incorporated
    Inventors: Oleg Kozyuk, Peter Reimers, Paul A. Reinking
  • Publication number: 20140096577
    Abstract: A process including at least one reactive trituration step which includes putting an oil cake including from 3% to 30% oil in contact with an anhydrous light alcohol and an alkaline catalyst under temperature and time conditions that are sufficient to allow for the extraction and transesterification of the vegetable oil and lead to the production of a mixture including fatty acid esters and glycerol, and a de-oiled cake including less than 3% oil. Also, a detoxified de-oiled cake as well as to a mixture of fatty acid esters with improved stability and resistance to oxidation.
    Type: Application
    Filed: May 23, 2012
    Publication date: April 10, 2014
    Applicant: ARKEMA FRANCE
    Inventors: Jean-Luc Dubois, Antoine Piccirilli
  • Patent number: 8686171
    Abstract: The present invention relates to methods and apparatus for producing alkyl esters from lipid feed stocks, such as plant oils and/or animal fats, and systems including the same. In an embodiment, the invention includes a process for producing alkyl esters including mixing a lipid feed stock with an alcohol to form a reaction mixture; and contacting the reaction mixture with a catalyst under supercritical conditions for the alcohol, the catalyst comprising an unmodified metal oxide selected from the group consisting of alumina, titania, zirconia, and hafnia, and removing residual free fatty acids from the reaction mixture. Other embodiments are included herein.
    Type: Grant
    Filed: January 10, 2011
    Date of Patent: April 1, 2014
    Assignee: McNeff Research Consultants, Inc.
    Inventors: Clayton V. McNeff, Larry C. McNeff, Arlin E. Gyberg, Bingwen Yan, Daniel Thomas Nowlan, Brian Krohn
  • Publication number: 20130345457
    Abstract: The present invention relates to systems and methods of using fatty acid alkyl ester solutions to refine feed stocks before converting the feed stocks into fatty acid fatty acid alkyl esters. In an embodiment, the invention includes a method for producing fatty acid alkyl esters. The method can include mixing a crude lipid feed stock with a refining solution to form a crude product mixture, the refining solution comprising greater than about 10 wt. % fatty acid alkyl esters. The method can include extracting the liquid phase from the crude product mixture to obtain a purified lipid feed stock. The method can also include reacting the purified lipid feed stock with an alcohol to form a product mixture comprising fatty acid alkyl esters. In an embodiment, the invention includes a method of making a fatty acid alkyl ester composition.
    Type: Application
    Filed: June 4, 2013
    Publication date: December 26, 2013
    Inventor: Clayton V. McNeff
  • Publication number: 20130331448
    Abstract: The present disclosure provides a process for producing 20-carbon fatty acids from a plant seed oil, the process comprising: a) providing a plant seed oil comprising fatty acids, wherein the fatty acids include 18-carbon fatty acids; and b) elongating the fatty acids by two carbon atoms to produce a composition comprising 20-carbon fatty acids.
    Type: Application
    Filed: November 29, 2012
    Publication date: December 12, 2013
    Applicant: DIGNITY SCIENCES LIMITED
    Inventor: DIGNITY SCIENCES LIMITED
  • Patent number: 8586772
    Abstract: The current invention describes processes for obtaining of concentrates of esters of eicosapentaenoic acid and docosahexaenoic acid for their use in massive and regular human consumption either as a pharmaceutical ingredient or as a food ingredient, which are characterized by having neutral and stable organoleptic properties, free of side effects, which are typical from marine oils derivatives, and with low content of Persistent Organic Pollutants (POP).
    Type: Grant
    Filed: June 1, 2010
    Date of Patent: November 19, 2013
    Assignee: Golden Omega S.A.
    Inventors: Tomas Francis Harting Glade, Miguel Angel Diaz Fuenzalida, Alejandro Markovits Rojas
  • Publication number: 20130303796
    Abstract: A method for continuously preparing a carboxylic acid ester is disclosed. In the method of the present invention, a vertical reactor is filled with a solid catalyst, a carboxylic acid and an alcohol are introduced into a lower part of the vertical reactor, esterification is performed to form an esterized mixture, the esterized mixture is output from an upper part of the vertical reactor, and distillation is performed to isolate the carboxylic acid ester. The method of the present invention is simple, easily controlled and environmental friendly, and has significantly high conversion rate and selectivity.
    Type: Application
    Filed: October 15, 2012
    Publication date: November 14, 2013
    Applicant: China Petrochemical Development Corporation, Taipei (Taiwan)
    Inventors: Jih-Dar Hwang, Yung-Shun Kung, Yao-Ching Tsai
  • Publication number: 20130295268
    Abstract: Chemically modified lipids and methods for their preparation are provided.
    Type: Application
    Filed: May 7, 2013
    Publication date: November 7, 2013
    Applicant: Solazyme, Inc.
    Inventors: Anthony G. Day, Geoffrey Brooks, Scott Franklin
  • Publication number: 20130289009
    Abstract: The present invention relates to the use of at least one vegetable oil refining industry by-product to obtain a purified total unsaponifiable of vegetable oil cleared of the impurities initially present in the said by-product, advantageously cleared of sapid and odorous compounds and/or chemical compounds resulting from the deterioration and the degradation of vegetable oils. The invention further relates to a method for obtaining a purified total unsaponifiable of vegetable oil from at least one vegetable oil refining industry by-product. The invention further relates to a purified total unsaponifiable of vegetable oil able to be obtained by this method, as well as compositions containing such an unsaponifiable. The invention further relates to such unsaponifiables or such compositions for the use thereof as a drug, medical device, dermatological agent, cosmetic agent or nutraceutical, in humans or animals.
    Type: Application
    Filed: January 31, 2012
    Publication date: October 31, 2013
    Inventors: Jacques Legrand, Alex Saunois, Caroline Baudouin, Philippe Msika
  • Publication number: 20130289290
    Abstract: The present invention concerns a method for the production of carboxylic acid esters containing the steps: a. Supplying of a component containing carboxylic acid and an alcohol; b. Bringing the component containing carboxylic acid in contact with the alcohol in a container for a conversion to carboxylic acid esters by means of esterification or transesterification, characterized in that the container is moved over a distance of at least 1 kilometer during the esterification or the transesterification. The present invention also concerns the use of a ship.
    Type: Application
    Filed: November 7, 2011
    Publication date: October 31, 2013
    Applicant: EMERY OLEOCHEMICALS GMBH
    Inventors: Heinz Muller, Diana Maker
  • Patent number: 8569530
    Abstract: Various embodiments of the present invention are directed to processes and methods for converting lipids comprising fatty acids into fatty esters. According to various embodiments of the invention, the saponifiable lipids are reacted with a base to form alkali soaps. The alkali soaps are then reacted with an acid to form fatty esters. Both the base reaction and the acid reaction may occur in the presence of one or more alcohols. Following the acid reaction, a solvent may be added to effect a separation of the fatty esters, which may then be recovered.
    Type: Grant
    Filed: April 1, 2011
    Date of Patent: October 29, 2013
    Assignee: Aurora Algae, Inc.
    Inventors: Jeffrey G. Hippler, Andy Thompson, Lea Dulatas, Louis A. Kapicak
  • Patent number: 8558022
    Abstract: 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: Grant
    Filed: April 7, 2011
    Date of Patent: October 15, 2013
    Assignee: Dow Global Technologies LLC
    Inventors: Daniele Vinci, Jochem Kersbulck
  • Patent number: 8557139
    Abstract: The present invention is a replacement plasticizer system made from or containing an epoxidized fatty acid ester plasticizer as a primary plasticizer and a secondary plasticizer. The replacement placement system is useful with a variety of polymers in applications such as wire-and-cable insulations, wire-and-cable jackets, coatings, adhesives, and castings.
    Type: Grant
    Filed: February 12, 2009
    Date of Patent: October 15, 2013
    Assignee: Dow Global Technologies LLC
    Inventor: Robert F. Eaton
  • Publication number: 20130237718
    Abstract: Process for preparation of a supported catalyst based on hydroxylated inorganic material selected from the group consisting of silica (SiO2), alumina (AL2O3), titania (TiO2), zirconia (ZrO2), lanthanum oxide (La2O3) or mixtures thereof, characterized in that the hydroxylated inorganic material is contacted with organosilicon compounds selected from the group consisting of Formula 1 i.e., [(RO)ySi—[O—(RO)ySi]y—O—Si(RO)y] or Formula 2 i.e., (RO)y—Si—R1—S2-4—R1—Si—(RO)y with R being alkyl and R1 being a linear or branched alkylene having from 1 to 5 carbon atoms and y being an integer from 1 to 3.
    Type: Application
    Filed: October 19, 2011
    Publication date: September 12, 2013
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Ralf Hausmann, Manfred Fuchs, Stefan Röder, Cristiano Trionfetti
  • Patent number: 8501974
    Abstract: Disclosed is a process for producing alkyl fatty esters from fats/oils and C1 to C5 lower alcohols by a multistage reaction process, which includes feeding fats and oils to a reactor at an upper stage and then sent to a stage at the downstream side while feeding lower alcohols to a reactor at a lower stage, and simultaneously returning lower alcohols recovered from an outlet of the reactor to a stage at the upstream side, thereby repeating the reaction.
    Type: Grant
    Filed: December 26, 2006
    Date of Patent: August 6, 2013
    Assignee: Kao Corporation
    Inventors: Wataru Nomura, Nobuhiro Tatsumi, Takanobu Katayama
  • Patent number: 8481771
    Abstract: 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: Grant
    Filed: March 21, 2008
    Date of Patent: July 9, 2013
    Assignee: CPS Biofuels, Inc.
    Inventors: David Bradin, Guerry L. Grune
  • Patent number: 8466304
    Abstract: 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: Grant
    Filed: December 22, 2009
    Date of Patent: June 18, 2013
    Assignee: IFP Energies Nouvelles
    Inventors: Arnaud Baudot, Laurent Bournay, Eszter Toth
  • Patent number: 8449629
    Abstract: 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: Grant
    Filed: December 9, 2011
    Date of Patent: May 28, 2013
    Assignee: Endicott Biofuels II, LLC
    Inventor: William Douglas Morgan
  • Patent number: 8445400
    Abstract: The present invention provides a novel glycerol-based heterogeneous solid acid catalyst by simultaneous partial carbonization and sulfonation of crude glycerol obtained as a by-product during the biodiesel process. Solid acid catalyst with similar activity is also prepared from glycerol pitch (by-product of fat splitting) and technical grade glycerol. These glycerol-based solid acid catalysts are employed for esterification of fatty acids and fatty acid present in the high and low free fatty acid (FFA) containing vegetable oils like rice bran, karanja and jatropha; fatty acid distillate; deodorizer distillate and acid oil which are being used as raw materials for the preparation of biodiesel. These catalysts are highly active, reusable and simplify the biodiesel process particularly for fatty acids or high FFA containing vegetable oils by replacing the traditional homogeneous mineral acid catalysts.
    Type: Grant
    Filed: October 26, 2007
    Date of Patent: May 21, 2013
    Assignee: Council of Scientific & Industrial Research
    Inventors: Bethala Lakshmi Anu Prabhavathi Devi, Katkam Nadpi Gangadhar, Potharaju Seetharamanjaneya Sai Prasad, Rachapudi Badari Narayana Prasad
  • Patent number: 8444719
    Abstract: The invention relates to a method and apparatus for the batch preparation of esters of fatty acids obtained from biological sources. In particular, the invention relates to a method and apparatus for the batch preparation of methyl esters of fatty acids obtained from waste oil or animal fats for use as biodiesel.
    Type: Grant
    Filed: July 16, 2008
    Date of Patent: May 21, 2013
    Assignee: Ecodiesel Limited
    Inventor: Gary Brockett
  • Patent number: 8420842
    Abstract: This invention proposes a lanolin substitute, capable of absorbing up to at least twice its weight of water or aqueous solution or aqueous suspension. It forms true emulsions, stable over time with a capacity for water absorption superior to that of lanolin. It also possesses the known emollient, moisturizing and occlusive properties of lanolin. This substitute is usable in all the present and future areas of application of lanolin: in the cosmetics industry, dermatology, and in industrial applications (polishes, lubricants . . . ). It is obtained by hemi-synthesis from a mixture of unsaturated fatty acids, esters of unsaturated fatty acids, unsaturated hydrocarbons or unsaturated derivatives of the latter and compounds comprising or generating hydroxyl functions, such as glycerol, preferably without a catalyst and in an atmosphere devoid of oxygen. Classical thermal treatment or preferably treatment by dielectric heating.
    Type: Grant
    Filed: June 28, 2002
    Date of Patent: April 16, 2013
    Assignee: Aldivia SA
    Inventors: Pierre Charlier De Chily, Mikaele Raynard
  • Patent number: 8420840
    Abstract: A method comprising providing a starting composition comprising a polyunsaturated fatty acid, a polyunsaturated fatty ester, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated triglyceride, or a mixture thereof; self-metathesizing the starting composition or cross-metathesizing the starting composition with at least one short-chain olefin in the presence of a metathesis catalyst to form self-/cross-metathesis products comprising: cyclohexadiene; at least one olefin; and one or more acid-, ester-, or salt-functionalized alkene; and reacting cyclohexadiene to produce at least one cycloalkane or cycloalkane derivatives.
    Type: Grant
    Filed: December 2, 2011
    Date of Patent: April 16, 2013
    Inventor: Edwin S. Olson
  • Patent number: 8404005
    Abstract: 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: Grant
    Filed: September 10, 2009
    Date of Patent: March 26, 2013
    Assignee: Board of Regents, The University of Texas System
    Inventors: Brian H. Dennis, Richard E. Billo, Christopher R. Oliver, John W. Priest, Elinor Kolesar
  • Patent number: 8378132
    Abstract: Transesterification systems and methods for producing methyl ester are disclosed. In one embodiment, a method for producing methyl ester includes introducing a first charge into a reactor. The first charge contains a triglyceride-containing fat and an alcohol. The method can also include performing a first transesterification reaction in which the triglyceride-containing fat is reacted with the alcohol to produce a first product. The method can further include settling the first product into a methyl ester-containing layer and a glycerol-containing layer, decanting the glycerol-containing layer after settling from the reactor, mixing a second charge with the first product, and performing a second transesterification reaction after mixing the second charge with the first product.
    Type: Grant
    Filed: February 15, 2008
    Date of Patent: February 19, 2013
    Inventor: Daniel W. Lemke
  • Publication number: 20130036713
    Abstract: 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: Application
    Filed: December 30, 2010
    Publication date: February 14, 2013
    Inventors: Peter Daute, Wilhelm Reiners, Martin Schäfer, Udo Frerichs, Hinrich Hildebrandt, Joern Ellerbrake
  • Publication number: 20130030205
    Abstract: A method of esterifying free fatty acid in natural oil comprises heating the natural oil (2) to a first temperature above a reaction temperature, feeding the heated natural oil into an acid-resistant pipe reactor (5), providing a mixture of acid catalyst (6) and short chain alcohol (8) at a second temperature below the reaction temperature, and feeding the mixture of acid catalyst and short chain alcohol into the natural oil in the pipe reactor (5). The short chain alcohol and free fatty acid react at the reaction temperature to form an ester.
    Type: Application
    Filed: February 7, 2011
    Publication date: January 31, 2013
    Inventors: Richard Davis Jackson, Owen Matthew Davies
  • Patent number: 8362288
    Abstract: A process for preparing a composition of alcoholic esters of straight chain monocarboxylic acids containing 6 to 26 carbon atoms and glycerin, starting from a vegetable or animal oil, neutral or acidic, virgin or recycled with mono-alcohols containing 1 to 18 atoms, in the presence of a zinc aluminate catalyst and in the presence of a controlled quantity of water, can directly produce, in one or more steps, an ester which can be used as a propellant or fuel along with glycerin having improved purity containing a reduced quantity of ethers by using a partially dried catalyst.
    Type: Grant
    Filed: September 10, 2010
    Date of Patent: January 29, 2013
    Assignee: IFP Energies Nouvelles
    Inventors: Vincent Coupard, Sylvie Maury, Veronique Pugnet
  • Publication number: 20130006006
    Abstract: Chemicals prepared from oleaginous microbes and related methods are provided.
    Type: Application
    Filed: August 31, 2012
    Publication date: January 3, 2013
    Applicant: Solazyme, Inc.
    Inventors: Anthony G. Day, Geoffrey Brooks, Scott Franklin
  • Publication number: 20120289726
    Abstract: Described are processes for obtaining fatty acids with reduced content of by-products, wherein: (a) unrefined fats or oils are subjected to steam stripping in a counter-current column to produce (i) a bottom fraction of de-acidified fats or oils, (ii) a first distillate consisting mainly of fatty acids and glycerides, and (iii) a second distillate comprising fatty acids and essentially all unwanted ketones, aldehydes and phenols; and (b) said bottom fraction (i) containing the de-acidified fats or oils and said first distillate (ii) containing fatty acids and glycerides are combined.
    Type: Application
    Filed: May 12, 2012
    Publication date: November 15, 2012
    Applicant: Cognis IP Management GmbH
    Inventors: Horst Josten, Ewelina Sobierska, Adrian Chan, Truc Tran Anh