Molecular Rearrangement Of The Acid Moieties Of Glyceride Esters (e.g., Random Or Directed Low Temperature Intra- Or Inter-esterification Of Fats, Oils, Etc.) Patents (Class 554/169)
  • Patent number: 11248190
    Abstract: PROBLEM To provide a composition comprising highly enriched PUFA or its alkyl esters while containing fatty acid esters of 3-MCPD at adequately low concentrations and to provide an efficient method for producing the composition. MEANS FOR SOLVING A composition that contains fatty acids or fatty acid alkyl esters as its major component, the composition containing highly unsaturated fatty acid or alkyl ester thereof, wherein the proportion of the highly unsaturated fatty acid in the constituent fatty acids of the composition is 50 area % or more and wherein the concentration of 3-MCPD as found upon analyzing the composition by American Oil Chemists' Society official method Cd 29b-13 assay A is less than 1.80 ppm.
    Type: Grant
    Filed: May 22, 2020
    Date of Patent: February 15, 2022
    Assignee: Nippon Suisan Kaisha, Ltd.
    Inventors: Nobushige Doisaki, Kiyomi Furihata, Hideaki Yamaguchi
  • Patent number: 10927323
    Abstract: PROBLEM To provide a composition comprising highly enriched PUFA or its alkyl esters while containing fatty acid esters of 3-MCPD at adequately low concentrations and to provide an efficient method for producing the composition. MEANS FOR SOLVING A composition that contains fatty acids or fatty acid alkyl esters as its major component, the composition containing highly unsaturated fatty acid or alkyl ester thereof, wherein the proportion of the highly unsaturated fatty acid in the constituent fatty acids of the composition is 50 area % or more and wherein the concentration of 3-MCPD as found upon analyzing the composition by American Oil Chemists' Society official method Cd 29b-13 assay A is less than 1.80 ppm.
    Type: Grant
    Filed: May 22, 2020
    Date of Patent: February 23, 2021
    Assignee: Nippon Suisan Kaisha, Ltd.
    Inventors: Nobushige Doisaki, Kiyomi Furihata, Hideaki Yamaguchi
  • Patent number: 10822572
    Abstract: The present invention relates to a process for the production of basic biosolvents derived from inedible vegetable oil or animal fat or waste fatty acid composition by one-pot reaction between inedible vegetable oil or animal fat or waste fatty acid, and at least one ester of short-chain organic acid having 2, 3 or 5 carbon atoms, derived from biomass, in the presence of heterogeneous catalysts. In addition, the invention also relates to basic biosolvents, comprising alkyl esters of fatty acid, trieste of glycerin, esters of short-chain organic acids having 2, 3 or 5 carbon atoms, suitable for preparing many types of biosolvents, depending on application requirements.
    Type: Grant
    Filed: April 13, 2019
    Date of Patent: November 3, 2020
    Assignee: National Key Laboratory For Petrochemical and Refinery Technnologies
    Inventor: Thu Ha Thi Vu
  • Patent number: 10786801
    Abstract: Sono-chemical reactors and methods of using the same are provided. The sono-chemical reactors may include a plurality of sections that are sequentially connected along a longitudinal direction of the sono-chemical reactor. The plurality of sections may include a sono-reactor section that includes a reactant inlet through which reactants are supplied into the sono-reactor section and a static mixer section that is configured to receive a first reactant/product mixture from the sono-reactor section and is configured mix the first reactant/product mixture therein for reaction between unreacted reactants. An inner space of the sono-reactor section may taper along the longitudinal direction of the chemical reactor away from the reactant inlet. The plurality of sections may also include a product separation section that is configured to receive a second reactant/product mixture from the static mixer section and is configured to separate a product from the second reactant/product mixture.
    Type: Grant
    Filed: November 21, 2017
    Date of Patent: September 29, 2020
    Assignee: KHALIFA UNIVERSITY OF SCIENCE AND TECHNOLOGY
    Inventors: Isam Janajreh, Mohammed Noorul Hussain, Tala El Samad, Fadi Ataya
  • Patent number: 10696923
    Abstract: Embodiments herein relate to the production of alkyl esters from lipid feed stocks. In an embodiment, a process for producing alkyl esters is included. The process can include mixing a lipid feed stock with an alcohol, water, and at least one of carbon dioxide, carbon monoxide, and/or one or more acids to form a reaction mixture, and contacting the reaction mixture with a catalyst under supercritical conditions for the alcohol, the catalyst comprising a metal oxide. Other embodiments are also included herein.
    Type: Grant
    Filed: February 7, 2019
    Date of Patent: June 30, 2020
    Assignee: SarTec Corporation
    Inventors: Charles Vincent McNeff, Clayton V. McNeff, Larry C. McNeff, Bingwen Yan
  • Patent number: 10335761
    Abstract: A reactor and process for the production of bio-diesel. The reactor includes one or more coiled reaction lines. The lines are positioned within a tank containing a heat transfer media such as molten salt, maintained at about 750° F. A pump circulates the media within the tank. An emulsion of alcohol; refined feed stock, including glycerides and/or fatty acids; and preferably water is pumped through the reaction lines at temperatures and pressures sufficient to maintain the alcohol in a super-critical state. The curvature of the coils, pump pulsing, and the flow rate of the emulsion keep the emulsion in a turbulent state while in the reactor, ensuring thorough mixing of the alcohol and feed stock. The alcohol reacts with the glycerides and fatty acids to form bio-diesel. The reaction is fast, efficient with regard to energy input and waste generation, and requires minimal alcohol.
    Type: Grant
    Filed: November 22, 2013
    Date of Patent: July 2, 2019
    Assignee: Louisiana Eco Green, L.L.C.
    Inventors: Kemper J. McSpadden, Gerard M. Thomassie
  • Patent number: 10065915
    Abstract: The present invention relates to the production of biodiesel and alkyl esters by the transesterification of triglyceride esters, with alcohols in heterogeneous phase in the presence of heterogeneous catalysts, with yields higher than 80%, at a temperature from 0 to 300° C., residence time from 20 minutes to 20 h, space velocity of 0.1 to 10 h?1, pressure of 25-100 kg/cm2 (24.5-98.07 bar), methanol/oil molar ratio of 10 to 40 and catalyst concentration of 0.001 to 20 weight % based on tri-, di- or monoglyceride. The method produces biodiesel and alkyl esters by transesterification of tri-, di- or mono-glycerides, from palm, jatropha, castor, soybean and sunflower oils, wherein the alcohoxyls R1O, R2O and R3O of the glycerides are C1 to C24 and a C1-C4 alcohol, such as methanol, in an alcohol:oil ratio from 3:1 to 50:1.
    Type: Grant
    Filed: March 30, 2017
    Date of Patent: September 4, 2018
    Assignee: INSTITUTO MEXICANO DEL PETROLEO
    Inventors: Federico Jesus Jimenez Cruz, Celia Marin Rosas, Luis Carlos Castaneda Lopez, Rogelio Hernandez Suarez, Javier Esteban Rodriguez Rodriguez, Maria del Carmen Martinez Guerrero, Florentino Rafael Murrieta Guevara, Alicia del Rayo Jaramillo Jacob
  • Patent number: 9718757
    Abstract: Methods and systems for the production and isolation of fatty acid methyl esters (FAMEs) from a lipid source are described. The method includes extracting a lipid from a lipid source and transesterifying the lipid into a FAME. The method may also include fractionating the FAME from the system. A method of selectively transesterifying a lipid into a FAME is also described.
    Type: Grant
    Filed: September 27, 2013
    Date of Patent: August 1, 2017
    Assignee: YALE UNIVERSITY
    Inventors: Julie B. Zimmerman, Lindsay Soh
  • Patent number: 9605165
    Abstract: Mixture of triglycerides obtained from vegetable oils comprising one or more of the following oligomeric structures: R4-[O—C(O)—R1-C(O)—O—CH2-CH(OR2)-CH2]n-O—R3 wherein R1 is selected from C2-C22 alkylenes, R2 is selected from one or more of the following groups consisting of C6-C24 dicarboxylic acid residues and C6-C24 monocarboxylic acid residues, R3 is selected from one or more of the following groups consisting of H, C6-C24 dicarboxylic acid residues and C6-C24 monocarboxylic acid residues, R4 is an alkyl group, n is an integer greater than or equal to 2, said C6-C24 dicarboxylic acid residues of R2 and R3 being esterified with monoalcohols and said mixture of triglycerides having a Numerical Average Molecular Weight (Mn) of between 800 and 10.000 Da.
    Type: Grant
    Filed: December 3, 2015
    Date of Patent: March 28, 2017
    Assignee: NOVAMONT S.P.A.
    Inventors: Catia Bastioli, Luigi Capuzzi, Paolo Magistrali, Sebastià Gesti' Garcia
  • Patent number: 9481632
    Abstract: Butters are a specific class of cosmetic triglycerides that provide a unique feel on skin. There are very few such materials in nature. In order for a butter to be of interest to the personal care market, it must be (1) soft at room temperature; (2) must not “crack” when handled; (3) must be able to be applied to the skin at ambient temperature by rubbing; (4) must liquefy upon rubbing, (5) must be free of rancidity and (6) must be free of trans acids that are the result of partial hydrogenation. For unsaturated oils to be made into butters, partial hydrogenation is the most common approach. This results in the formation of trans acids which are highly undesirable. The present invention discloses a series of non-hydrogenated butters made by a process referred to as totally randomized triglycerides. The butters are made using a very specific range of very specific types and ratios of fatty acids to glycerin to provide the highly desirable cosmetic butters meeting the requirements 1-5 above.
    Type: Grant
    Filed: March 27, 2015
    Date of Patent: November 1, 2016
    Assignee: SURFATECH CORPORATION
    Inventors: Thomas George O'Lenick, Andrew James O'Lenick
  • Patent number: 9327254
    Abstract: A mixing process is provided for the valorization of used cooking oils. The mixing process takes place in a particularly efficient way and includes supplying a given load (A) of used cooking oils and a corresponding load (B) of a solidifying composition to a mixing device. Thermal energy is supplied and in particular, an initial amount of thermal energy is supplied to cause the mixing temperature to reach a given temperature level. An additional amount of thermal energy is also supplied during a given mixing period. The solidifying composition includes a processing compound that includes at least two substances, one of which is of a wax type and the other is one of stearic acid, aromatic, coloring substances and additives.
    Type: Grant
    Filed: April 4, 2012
    Date of Patent: May 3, 2016
    Assignee: O2W S.A.
    Inventor: Americo Arnoni Junior
  • Patent number: 8981135
    Abstract: 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: Grant
    Filed: November 5, 2013
    Date of Patent: March 17, 2015
    Assignee: Cavitation Technologies, Inc.
    Inventors: Roman Gordon, Igor Gorodnitsky, Varvara Grichko
  • Patent number: 8980949
    Abstract: The present invention provides a use of a lipid composition for the preparation of a nutritional, pharmaceutical or nutraceutical composition or a functional food, for the prevention and treatment of gastrointestinal diseases and disorders, and for promoting intestinal development, maturation, adaptation and differentiation.
    Type: Grant
    Filed: December 20, 2013
    Date of Patent: March 17, 2015
    Assignee: Enzymotec Ltd.
    Inventors: Fabiana Bar-Yosef, Gai Ben Dror, Tzafra Cohen, Yael Lifshitz
  • Patent number: 8981136
    Abstract: The invention relates to a process for making esters, in particular biodiesel, using heterogeneous catalysts. The invention provides a process for making biodiesel, in particular FAME, which process is versatile and robust. The process of the invention can be carried out continuously, in particular in a fixed bed reactor or a slurry reactor and may be operated in a continuous fashion. In accordance with the invention, the transesterification reaction of triglycerides is carried out using a heterogeneous catalyst that comprises a Group 4 silicate and less than 3 wt. % Na in the presence of at least one acid compound.
    Type: Grant
    Filed: October 12, 2012
    Date of Patent: March 17, 2015
    Assignee: BASF Corporation
    Inventor: Jim Aloysius Maria Brandts
  • Publication number: 20150072400
    Abstract: 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: Application
    Filed: May 5, 2014
    Publication date: March 12, 2015
    Inventor: William Severn Clarke
  • Patent number: 8975426
    Abstract: A method of forming a product from an oil feedstock, such as a biodiesel product, and a heterogeneous catalyst system used to form said product is disclosed. This catalyst system, which has a high tolerance for the presence of water and free fatty acids (FFA) in the oil feedstock, may simultaneously catalyze both the esterification of FAA and the transesterification of triglycerides present in the oil feedstock. The catalyst system is comprised of a mixture of zinc oxide and a second metal oxide. The zinc oxide includes a mixture of amorphous zinc oxide and zinc oxide nanocrystals, the zinc nanocrystals having a mean grain size between about 20 and 80 nanometers with at least one of the nanocrystals including a mesopore having a diameter of about 5 to 15 nanometers. Preferably, the second metal oxide is a lanthanum oxide, the lanthanum oxide being selected as one from the group of La2CO5, LaOOH, and combinations or mixtures thereof.
    Type: Grant
    Filed: June 16, 2010
    Date of Patent: March 10, 2015
    Assignee: Wayne State University
    Inventors: Shuli Yan, Steven O. Salley, K. Y. Simon Ng
  • Patent number: 8907113
    Abstract: A process for separating glycerin from methyl ester at an enhanced rate is disclosed. The improved process results from carrying out the transesterification reaction in a substantially non-polar and water free environment. A polymer selected from a group of polymers shown to be effective in such an environment is added to the product mixture which greatly improves the rate of separation between the methyl ester and the glycerin and reduces the number of required steps to accomplish the separation.
    Type: Grant
    Filed: July 1, 2012
    Date of Patent: December 9, 2014
    Inventors: Aicardo Roa-Espinosa, Hailin Lin
  • Patent number: 8901330
    Abstract: Alkyl esters boiling largely within the specification range for jet fuel may be made from triglycerides without a water-washing step, by centrifugation in a timely manner and at a sufficiently high time/G-force/distance product so as to bring about separation of a transitory second phase containing the residual catalyst. The esters or fractions thereof may be combined with jet or diesel fuels to lower the freezing and cloud points respectively.
    Type: Grant
    Filed: August 28, 2008
    Date of Patent: December 2, 2014
    Assignee: Sauber LLC
    Inventors: Michael Phillip Doyle, Steve Smith
  • Patent number: 8895764
    Abstract: A method of forming a biodiesel product and a heterogeneous catalyst system used to form said product that has a high tolerance for the presence of water and free fatty acids (FFA) in the oil feedstock is disclosed. This catalyst system may simultaneously catalyze both the esterification of FAA and the transesterification of triglycerides present in the oil feedstock. The catalyst system is comprised of a mixture of zinc oxide and a second metal oxide. The zinc oxide includes a mixture of amorphous zinc oxide and zinc oxide nanocrystals, the zinc nanocrystals having a mean grain size between about 20 and 80 nanometers with at least one of the nanocrystals including a mesopore having a diameter of about 5 to 15 nanometers. Preferably, the second metal oxide is a lanthanum oxide, the lanthanum oxide being selected as one from the group of La2CO5, LaOOH, and combinations or mixtures thereof.
    Type: Grant
    Filed: June 16, 2009
    Date of Patent: November 25, 2014
    Assignee: Wayne State University
    Inventors: Shuli Yan, Steven O. Salley, K. Y. Simon Ng
  • Patent number: 8889895
    Abstract: The present invention relates to a method for working up a mixture which contains esters of EPA and/or DHA with monohydric alcohols having 1 to 6 carbon atoms, esters of other fatty acids with monohydric alcohols having 1 to 6 carbon atoms, and free cholesterol, wherein the method comprises adding a transesterification catalyst to the mixture, converting at least some of the free cholesterol into esterified cholesterol and thereafter distilling the mixture, wherein the distillation is carried out in such a manner that a product is obtained which contains EPA and/or DHA, both in the form of esters thereof with monohydric alcohols having 1 to 6 carbon atoms, in a higher relative amount, based on all fatty acids in free or bound form present in the product, than said mixture. In addition, the present invention relates to a product which is obtainable by the method according to the invention, wherein the product contains 10 to 99.
    Type: Grant
    Filed: March 3, 2012
    Date of Patent: November 18, 2014
    Assignee: Cognis IP Management GmbH
    Inventors: Dieter Hietsch, Peter Horlacher
  • Patent number: 8884077
    Abstract: A hydrocarbon conversion process comprises contacting a renewable feedstock under hydroprocessing conditions with a bulk catalyst to form oleochemicals such as fatty alcohols, esters, and normal paraffins. Advantageously, the reaction conditions can be selected to directly convert the renewable feedstock to the desired product(s).
    Type: Grant
    Filed: December 9, 2011
    Date of Patent: November 11, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventors: Cong-Yan Chen, Alexander E. Kuperman, William J. Cannella
  • Patent number: 8871961
    Abstract: 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: Grant
    Filed: March 2, 2011
    Date of Patent: October 28, 2014
    Assignee: Air Liquide Global E&C Solutions Germany GmbH
    Inventors: Eckhard Seidel, Rudolf Boensch, Norbert Palauschek, Helmut Saft
  • Patent number: 8865949
    Abstract: A hydrocarbon conversion process comprises contacting a renewable feedstock under hydroprocessing conditions with supported catalyst comprising at least one metal selected from the group consisting of Group VIII metals, Group VIB metals to form oleochemicals such as fatty alcohols, esters, and normal paraffins. Advantageously, the reaction conditions can be selected to directly convert the renewable feedstock to the desired product(s).
    Type: Grant
    Filed: December 9, 2011
    Date of Patent: October 21, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventor: Cong-Yan Chen
  • Publication number: 20140309445
    Abstract: Various methods are provided for metathesizing a feedstock. In one aspect, a method includes providing a feedstock comprising a natural oil, heating the feedstock to a temperature greater than 100° C. in the absence of oxygen, holding the feedstock at the temperature for a time sufficient to diminish catalyst poisons in the feedstock, and, following the heating and holding, combining a metathesis catalyst with the feedstock under conditions sufficient to metathesize the feedstock.
    Type: Application
    Filed: February 18, 2014
    Publication date: October 16, 2014
    Applicant: ELEVANCE RENEWABLE SCIENCES, INC.
    Inventors: Kevin D. Uptain, Charles Tanger, Hiroki Kaido
  • 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: 8853436
    Abstract: 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: Grant
    Filed: October 18, 2013
    Date of Patent: October 7, 2014
    Assignee: Petroleo Brasileiro S.A.-Petrobras
    Inventors: Márcio de Figueiredo Portilho, Alexander Rangel Bastos
  • Patent number: 8828269
    Abstract: A method of forming a stable mixture of a natural plant oil polyol and a petroleum-based polyol, including mixing a natural plant oil polyol with a monoglyceride, followed by adding a petroleum based polyol. Stabilized mixtures of plant oil and petroleum-based polyols can be used for synthesis of polyurethanes.
    Type: Grant
    Filed: November 5, 2010
    Date of Patent: September 9, 2014
    Inventors: Thomas M. Garrett, Xian Xian Du
  • 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: 8802877
    Abstract: 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: Grant
    Filed: December 17, 2009
    Date of Patent: August 12, 2014
    Assignee: NPC Industrias Quimicas Ltda
    Inventors: Milton Sobrosa Cordeiro, Sérgio Teixeira, Ariovaldo Fernandes Junior
  • Patent number: 8759556
    Abstract: The invention relates to a method for the selective extraction of functionalised fatty acid esters from seeds of oleaginous plants, wherein said method includes: a) at least one step of extracting fatty acid esters that comprises simultaneously feeding into a reactor containing said seeds a light anhydrous alcohol, a basic catalyst and an extraction solvent non-miscible with said light alcohol and in which said functionalised fatty ester is not soluble in order to obtain a mixture of esters and glycerol; b) and at least one step of selectively extracting hydroxylated fatty acid esters by feeding into the reactor said extraction solvent in a backflush direction relative to the light alcohol in order to obtain an alcohol phase enriched with fatty acid esters, a glycerol phase and a cake.
    Type: Grant
    Filed: January 13, 2010
    Date of Patent: June 24, 2014
    Assignee: Arkema France
    Inventors: Antoine Piccirilli, Jacques Barbier, Julien Magne, Jean-Luc Dubois
  • Patent number: 8735615
    Abstract: A method for extracting an unsaponifiable fraction from a renewable raw material selected among oilfruits, oleaginous seeds, oleoproteaginous seeds, seed husks, oil-yielding almonds, sprouts, stones and cuticles of fruits, high-fat raw materials from animals, algae, fungus or yeast, includes the following steps: a) dehydrating and packaging the renewable raw material, not resulting in any extraction of the fat; b) reactive crushing of the fatty packaged raw material in the presence of a light alcohol and a catalyst; c) evaporating the light alcohol; d) concentrating the liquid phase such as to obtain a concentrate including the unsaponifiable fraction diluted in fatty acid alkyl esters; e) saponifying the unsaponifiable concentrate; f) extracting the unsaponifiable fraction from the saponified mixture. The use of an unsaponifiable fraction or co-products obtained by implementing the method for preparing a composition such as a cosmetic, drug, food, or food additive or supplement is also described.
    Type: Grant
    Filed: October 21, 2010
    Date of Patent: May 27, 2014
    Assignee: Valagro Carbone Renouvelable Poitou-Charentes
    Inventor: Antoine Piccirilli
  • Patent number: 8722924
    Abstract: An integrated facility for the co-production of ethanol and biodiesel fuel is provided. Ethanol and corn oil, the primary product and a by-product from the ethanol plant, are utilized as feedstocks for a biodiesel plant operating within the same general facility as the corn ethanol plant. By-products of the biodiesel plant, principally crude liquid glycerol and gaseous ethanol or methanol, are recycled to various parts of the ethanol plant.
    Type: Grant
    Filed: January 30, 2014
    Date of Patent: May 13, 2014
    Assignee: WB Technologies LLC
    Inventors: Rachel Overheul, Brandon Awtrey, Daniel Johnson
  • Patent number: 8715980
    Abstract: 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: Grant
    Filed: December 10, 2010
    Date of Patent: May 6, 2014
    Assignee: Winwick Business Solutions Pty Ltd
    Inventor: William Severn Clarke
  • Patent number: 8704007
    Abstract: A hydrocarbon conversion process comprises contacting a renewable feedstock under hydroprocessing conditions with a bulk catalyst to form oleochemicals such as fatty alcohols, esters, and normal paraffins. Advantageously, the reaction conditions can be selected to directly convert the renewable feedstock to the desired product(s).
    Type: Grant
    Filed: December 9, 2011
    Date of Patent: April 22, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventors: Cong-Yan Chen, Alexander E. Kuperman, William J. Cannella
  • Patent number: 8692008
    Abstract: The present invention relates to a process for preparing fatty acid esters and/or fatty acid ester mixtures of monohydric alcohols having 1 to 5 carbon atoms by transesterifying fatty acid glycerides with monohydric alcohols in the presence of a basic catalyst, in the course of which methanesulfonic acid is used. The invention further relates to the use of methanesulfonic acid for preparing these fatty acid esters.
    Type: Grant
    Filed: November 16, 2009
    Date of Patent: April 8, 2014
    Assignee: BASF SE
    Inventor: Stefan Fabβbender
  • Patent number: 8692007
    Abstract: The present invention relates to a method for the transesterification of a hydroxylated oil including two consecutive transesterification steps performed in the presence of a light alcohol (methanol or ethanol) and a basic catalyst under temperature, pressure and alcohol/oil weight ratio conditions enabling the nearly total conversion of the hydroxylated oil into fatty acid esters. Characteristically, a resulting directly from the first transestrefication step in order to obtain a reaction mixture including, in particular, hydroxylated fatty acid esters and glycerol. Said reaction mixture is subjected to a separation step that makes it possible to obtain a less dense phase predominantly consisting of fatty esters and a denser phase predominantly consisting of glycerol and water and fatty acid soaps. The second transesterification step is performed on the less dense phase, with said light alcohol and said basic catalyst are added thereto.
    Type: Grant
    Filed: November 10, 2009
    Date of Patent: April 8, 2014
    Assignee: Arkema France
    Inventors: Jean-Francois Devaux, Georges Martino-Gauchi, Patrice Iafrate, Patricia Balouin, Thibault Balouin, Jeremie Balouin
  • Patent number: 8686170
    Abstract: A method of preparing a composition of alcohol esters of linear monocarboxylic acids with 6 to 26 carbon atoms from a vegetable or animal oil, neutral or acid, virgin or recycled, with monoalcohols having 1 to 18 carbon atoms, in the presence of a catalyst of nitrogen-containing metallophosphate type.
    Type: Grant
    Filed: June 1, 2011
    Date of Patent: April 1, 2014
    Assignee: IFP Energies Nouvelles
    Inventors: Delphine Bazer-Bachi, Francois Chevire, Vincent Lecocq, Erwan Ray, Pascal Raybaud, Franck Tessier
  • Patent number: 8685881
    Abstract: The present invention relates to a method for producing esters from triglycerides by using solid heterogeneous catalysts comprised of calcined calcium carbonate, particularly for obtaining biodiesel.
    Type: Grant
    Filed: November 20, 2009
    Date of Patent: April 1, 2014
    Assignee: Rohm and Haas Company
    Inventors: Rajiv Banavali, Jose Trejo
  • Patent number: 8664416
    Abstract: The present invention describes a process for the production of alkyl esters of fatty acids and glycerine employing, in a reaction section, at least one transesterification reaction between an animal or vegetable oil and an aliphatic mono-alcohol, and using a heterogeneous solid catalyst, in which the energy balance is improved by thermal integration of the energy released during the mono-alcohol condensation step.
    Type: Grant
    Filed: October 20, 2011
    Date of Patent: March 4, 2014
    Assignee: IFP Energies nouvelles
    Inventors: Laurent Bournay, Vincent Coupard, Pierre-Yves Martin, Yves Scharff, Yann Lepine
  • Patent number: 8648209
    Abstract: A biodiesel plant includes a loop-shaped reactor which circulates reactants, e.g., feed stock and a methanol catalyst mixture through mesh to mix the reactants and form crude biodiesel. The feed stock is preferably heated to about 200 to 210° F. After the reaction, methanol may be recovered. There may also be a tank for removal of glycerin from the crude biodiesel. In another embodiment, there is a method for reacting the feed stock and methanol catalyst mixture by circulating the reactants through a turbulence-creating path, such as by using mesh in the reactor.
    Type: Grant
    Filed: December 28, 2006
    Date of Patent: February 11, 2014
    Inventor: Joseph P. Lastella
  • Patent number: 8617866
    Abstract: 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: Grant
    Filed: November 13, 2008
    Date of Patent: December 31, 2013
    Inventors: Sobhi Basheer, Maisa Haj, Muhammad Kaiyal
  • Patent number: 8603198
    Abstract: 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: Grant
    Filed: June 22, 2010
    Date of Patent: December 10, 2013
    Assignee: Cavitation Technologies, Inc.
    Inventors: Roman Gordon, Igor Gorodnitsky, Varvara Grichko
  • Patent number: 8603959
    Abstract: Fatty esters of oligoesters of a dicarboxylic acid and a polyol retaining at least one free hydroxyl group, particularly of the formula (I): R1—[OR2O—C(O)—R3—(O)C—]m—R4 (I), where R1 is H, a monocarboxylic acid group, or R6O—[C(O)—R3—(O)C]—; R2s are residues of polyols having at least one substituent free hydroxyl; R3s are hydrocarbylene; R4 is —OH, —OM where M is a salt forming metal, amine or ammonium, —OR6, or —OR2O—R7; R5 is C7 to C21 hydrocarbyl; R6 is C8 to C22 hydrocarbyl; R7 is H, or —C(O)R5; and m is 1 to 20; provided that at least one of R1 and R4 is or includes a C8 to C22 group, are surfactants. A range of surfactant properties can be obtained by varying the molecules within these ranges. Especially where R2 is derived from a higher polyol e.g. sorbitol, R3 is C2 to C6, and the fatty terminal group is C8 to C14, the products can be highly water soluble and effective oil in water emulsifiers.
    Type: Grant
    Filed: October 18, 2005
    Date of Patent: December 10, 2013
    Assignee: Croda International PLC
    Inventors: Hanamanthsa S Bevinakatti, Alan G Waite
  • Patent number: 8592613
    Abstract: 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: Grant
    Filed: February 1, 2011
    Date of Patent: November 26, 2013
    Assignee: Inventure Renewables, Inc.
    Inventors: William W. Berry, Mark G. Tegen, William Rusty Sutterlin
  • Patent number: 8580986
    Abstract: 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 transesteri
    Type: Grant
    Filed: May 16, 2007
    Date of Patent: November 12, 2013
    Assignee: Cognis IP Management GmbH
    Inventors: Eric Dubreucq, Albrecht Weiss, Bernhard Gutsche, Bernd Fabry, Guy Moulin
  • Patent number: 8563759
    Abstract: A process for extracting lipids from microalgae; the process involves pretreating a quantity of non-homogenized microalgae with an aliphatic alcohol for a predetermined period of time. The pretreatment liberates a substantial portion of lipids from the microalgae without requiring energy intensive cell membrane disruptive technologies. The liberated lipids are then treated with a transesterification reagent to form fatty acid methyl esters. The fatty acid methyl esters are separated from the resulting mixture and may be further purified to remove remaining solvents or other impurities. The fatty acid methyl esters produced by the process are suitable as a green energy biodiesel product.
    Type: Grant
    Filed: October 2, 2010
    Date of Patent: October 22, 2013
    Assignee: Cal Poly Corporation
    Inventors: Matthew W Hutton, Corinne R Lehr
  • 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: 8519171
    Abstract: The present invention describes a method of producing fatty acid alkyl esters and glycerin implementing, in a reaction section, a set of transesterification reactions between a vegetable or animal oil and an aliphatic monoalcohol, and using a heterogeneous solid catalyst, comprising: a) a glycerin phase introduction stage, b) an excess alcohol evaporation stage, and c) a glycerin phase decantation stage. The supernatant ester phase obtained after decantation is then optionally sent to a coalescer, also allowing separation of the glycerin, then to a purification stage by adsorption on solids. This improved method prevents microemulsion formation.
    Type: Grant
    Filed: June 9, 2008
    Date of Patent: August 27, 2013
    Assignee: IFP Energies nouvelles
    Inventors: Abdelhakim Koudil, Romain Rousset, Laurent Bournay, Vincent Coupard
  • 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: 8491857
    Abstract: 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: Grant
    Filed: September 5, 2012
    Date of Patent: July 23, 2013
    Inventor: Antonio Cantizani