Another Reactant Contains Alcoholic Or Phenolic Hydroxy (e.g., Methy Ricinoleate, Etc.) Patents (Class 554/167)
  • Patent number: 10780433
    Abstract: The invention relates to a composition comprising: at least one alkane-sulphonic acid R—SO3H wherein R represents a saturated, linear or branched, hydrocarbon chain comprising from 1 to 4 carbon atoms, which can or cannot be substituted by at least one halogen atom, at least one aryl-sulphonic acid; and optionally at least one solvent, of which the proportions are as defined in the description. The invention also relates to the use of composition in a fatty acid esterification method.
    Type: Grant
    Filed: November 20, 2017
    Date of Patent: September 22, 2020
    Assignee: Arkema France
    Inventors: Jean-Alex Laffitte, Bernard Monguillon, Kuan Huwa Tan
  • Patent number: 10479860
    Abstract: A method for preparing a bio-based polycarbonate ester containing a repeating unit according to Formula 1 which comprises residue of Isosorbide and residue of CHDA (1,4-cyclohexanedicarboxylic acid).
    Type: Grant
    Filed: January 12, 2016
    Date of Patent: November 19, 2019
    Assignee: SK CHEMICALS CO., LTD.
    Inventors: Kwang Sei Oh, Jong-In Lee
  • Patent number: 10155717
    Abstract: Solid mixed catalysts and methods for use in conversion of triglycerides and free fatty acids to biodiesel are described. A batch or continuous process may be used with the catalysts for transesterification of triglycerides with an alkyl alcohol to produce corresponding mono carboxylic acid esters and glycerol in high yields and purity. Similarly, alkyl and aryl carboxylic acids and free fatty acids are also converted to corresponding alkyl esters. The described catalysts are thermostable, long lasting, and highly active.
    Type: Grant
    Filed: March 7, 2016
    Date of Patent: December 18, 2018
    Assignee: SBI BioEnergy
    Inventors: Inder Pal Singh, Shradha Singh, Ritesh Patel, Bharat Mistry, Manish Mehta, Peter Omolo Otieno
  • Patent number: 10081590
    Abstract: A device and a process for producing undecylenic acid methyl ester using methyl ricinoleate as raw material are provided. The device comprises a feed pump, a raw material pre-heater, a microwave catalytic reactor, a microwave generator, a temperature controller and an infrared sensor, a condenser, a product tank and a discharge pump. The feed pump is connected with the raw material pre-heater, which is connected with the inlet of the microwave catalytic reactor. The outlet of the microwave catalytic reactor is connected with the condenser, which is connected to the product tank and the discharge pump. The microwave catalytic reactor is located in the microwave generator, which is connected with the temperature controller and the infrared sensor. The process is as follows: high-purity methyl ricinoleate, used as the raw material, is converted to methyl undecene and heptaldehyde by microwave-assisted pyrolysis process, followed by isolation and purification to produce methyl undecene.
    Type: Grant
    Filed: August 26, 2017
    Date of Patent: September 25, 2018
    Assignee: Zhejiang University of Technology
    Inventors: Yong Nie, Ying Duan, Ruchao Gong, Shangzhi Yu, Meizhen Lu, Jianbing Ji
  • Patent number: 10030205
    Abstract: The present disclosure concerns embodiments of a catalyst system, such as a mixed catalyst composition, that can be used to make biofuel. In some embodiments, the mixed catalyst composition can comprise an inorganic catalyst and an organic catalyst, such as a cyclic organic catalyst. In particular disclosed embodiments, a mixed catalyst composition comprising, consisting essentially of, or consisting of an inorganic catalyst and an organic catalyst can be used to enhance the production of biofuel, such as biodiesel, by reducing the amount of time needed to make the biofuel as compared to that needed for the inorganic catalyst or the organic catalyst independently. Also disclosed herein are combinations and kits comprising, consisting essentially of, or consisting of embodiments of a mixed catalyst composition.
    Type: Grant
    Filed: July 31, 2015
    Date of Patent: July 24, 2018
    Assignee: Board of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada, Reno
    Inventor: Dev Chidambaram
  • Patent number: 9975991
    Abstract: Disclosed is a bio-based polycarbonate ester comprising: (i) repeat unit 1 obtained from a condensation reaction of 1,4:3,6-dianhydrohexitol and carbonate; and (ii) repeat unit 2 obtained from a condensation reaction of 1,4:3,6-dianhydrohexitol and 1,4-cyclohexanedicarboxylate; and a preparation method for the bio-based polycarbonate ester, comprising the steps of: (1) preparing a compound 1,4-diphenyl-cyclohexanedicarboxylate through a trans-esterification or esterification reaction of a compound represented by and phenol; and (2) preparing a compound comprising a repeat unit represented by through a polycarbonate melt polycondensation reaction of the 1,4-diphenyl-cyclohexanedicarboxylate prepared in step (1), a compound represented by
    Type: Grant
    Filed: February 28, 2017
    Date of Patent: May 22, 2018
    Assignee: SK CHEMICALS CO., LTD.
    Inventors: Kwang Sei Oh, Il-Hoon Cha, Ji-hoon Kim
  • Patent number: 9909077
    Abstract: The present invention provides a method for producing a refined fatty acid alkyl ester (FAAE) product from feed-stocks containing free fatty acids. The method comprises glycerolysis and transesterification processes combined with end-product refining. Products produced from a transesterification reaction are separated into a crude FAAE stream and a crude glycerin stream. The crude glycerin stream is further processed to produce a glyceride stream from which additional FAAEs may be produced.
    Type: Grant
    Filed: July 9, 2014
    Date of Patent: March 6, 2018
    Assignee: REG Seneca, LLC
    Inventors: David A. Slade, Derek J. Winkel, Jared A. Downey
  • Patent number: 9725397
    Abstract: A system and method for the conversion of free fatty acids to glycerides and the subsequent conversion of glycerides to glycerin and biodiesel includes the transesterification of a glyceride stream with an alcohol. The fatty acid alkyl esters are separated from the glycerin to produce a first liquid phase containing a fatty acid alkyl ester rich (concentrated) stream and a second liquid phase containing a glycerin rich (concentrated) stream. The fatty acid alkyl ester rich stream is then subjected to distillation, preferably reactive distillation, wherein the stream undergoes both physical separation and chemical reaction. The fatty acid alkyl ester rich stream is then purified to produce a purified biodiesel product and a glyceride rich residue stream. The glycerin rich second liquid phase stream may further be purified to produce a purified glycerin product and a (second) wet alcohol stream.
    Type: Grant
    Filed: June 21, 2013
    Date of Patent: August 8, 2017
    Assignee: REG Seneca, LLC
    Inventors: John P. Jackam, Derek J. Winkel, Jared A. Downey
  • Patent number: 9643163
    Abstract: A transesterification catalyst that is heterogeneous and a method for preparing said transesterification catalyst are provided. The catalyst can be used in a variety of transesterification reactor configurations including CSTR (continuous stirred tank reactors), ebullated (or ebullating) beds or any other fluidized bed reactors, and PFR (plug flow, fixed bed reactors). The catalyst can be used for manufacturing commercial grade biodiesel, biolubricants and glycerin.
    Type: Grant
    Filed: June 29, 2015
    Date of Patent: May 9, 2017
    Assignee: CRYSTAPHASE PRODUCTS, INC.
    Inventors: Umakant Pravinchandra Joshi, Peter Gregory Ham
  • Patent number: 9556398
    Abstract: A method for producing a high viscosity, low volatiles blown stripped plant-based oil is provided. The method may include the steps of: (i) obtaining a plant-based oil; (ii) heating the oil to at least 90C; (iii) passing air through the heated oil to produce a blown oil having a viscosity of at least 200 cSt at 40C; (iv) stripping the blown oil from step (iii) to reduce an acid value of the blown oil to from 5 mg KOH/g to about 9 mg KOH/g; (v) adding a polyol to the stripped oil from (iv), and (vi) stripping the oil from step (v) to reduce the acid value of the oil to less than 5.0 mg KOH/g or less.
    Type: Grant
    Filed: November 9, 2015
    Date of Patent: January 31, 2017
    Assignee: CARGILL, INCORPORATED
    Inventors: Michael John Hora, Patrick Thomas Murphy
  • Patent number: 9540590
    Abstract: A process and a system for producing a fatty acid alkyl ester from an alcohol and a feedstock containing transesterifiable lipids are provided.
    Type: Grant
    Filed: May 29, 2014
    Date of Patent: January 10, 2017
    Assignee: POLYVALOR, LIMITED PARTNERSHIP
    Inventors: Gregory Patience, Mahesh Edake, Cristian Neagoe, Daria Camilla Boffito
  • Patent number: 9511621
    Abstract: A heat transfer label comprising a support portion and a transfer portion for transfer of the transfer portion from the support portion to an article. Heat is applied to the support portion while the transfer portion is placed into contact with the article. The support portion comprises a release layer including a synthetic wax.
    Type: Grant
    Filed: February 4, 2011
    Date of Patent: December 6, 2016
    Assignee: Multi-Color Corporation
    Inventor: Jean-Paul Laprade
  • Patent number: 9487805
    Abstract: A variety of betaine esters, including dialkylaminoalkyl cocoate betaines and dialkylaminoalkyl hydrogenated cocoate betaines are disclosed. These betaines can be advantageously prepared in high yield and purity by a three-step transiterification chemoenzymatic process or a two-step direct esterficiation chemoenzymatic process. These betaine esters have excellent surfactant properties.
    Type: Grant
    Filed: September 3, 2015
    Date of Patent: November 8, 2016
    Assignee: Eastman Chemical Company
    Inventors: Christopher Harlan Burk, Stephanie Kay Clendennen, Neil Warren Boaz
  • Patent number: 9476009
    Abstract: The present invention provides a method of producing fatty acid alkyl esters from a lipid, comprising steps of introducing a gas comprising vapor of an alcohol selected from methanol, ethanol, 1-propanol, iso-propanol and butanols, into the lipid in a form of bubbles to enable the bubbles to pass through the lipid and be discharged from the lipid. The product may then be subjected to a transesterification process catalyzed by a base catalyst. The present invention is robust with low quality feedstocks thus significantly reduce production cost for biodiesel.
    Type: Grant
    Filed: April 20, 2015
    Date of Patent: October 25, 2016
    Assignees: Drexel University, Environmental Fuel Research, LLC
    Inventors: Richard Allan Cairncross, Megan Elizabeth Hums, Colin James Stacy
  • Patent number: 9416336
    Abstract: Methods of producing fatty acid ethyl esters (FAEE) using a direct transesterification process are described. The direct transesterification process uses low levels of chemical solvents, acid catalysts, and heating energy to produce the FAEE in a method with increased efficiency in a co-solvent system. The FAEE produced may be used in a variety of products including health, beauty, nutraceutical, and cosmetic products.
    Type: Grant
    Filed: October 7, 2015
    Date of Patent: August 16, 2016
    Assignee: HELIAE DEVELOPMENT LLC
    Inventor: Sandip Shinde
  • Patent number: 9364770
    Abstract: A portable biodiesel manufacturing or processing plant for processing on continuous basis a raw plant based oil feedstock to form biodiesel.
    Type: Grant
    Filed: December 20, 2012
    Date of Patent: June 14, 2016
    Assignee: The Biocube Corporation Ltd.
    Inventors: Laurence Baum, A Alexander Kelly
  • Patent number: 9365801
    Abstract: A system and method for the conversion of high free fatty acid (HFFA) containing oils defined as oils containing 20-100% free fatty acids (FFA) and low free fatty acid (LFFA) containing oils defined as oils containing 1-20% free fatty acids (FFA) into oil with less than 0.5% FFA (defined as NFFA oil) includes a combination of partial glycerolysis of HFFA oils to produce LFFA oils and subsequent stripping of LFFA oils to produce NFFA oils via steam distillation.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: June 14, 2016
    Assignee: Technochem International, Inc.
    Inventor: Sanjeev Agarwal
  • Patent number: 9303233
    Abstract: A method for producing diesel grade fuel of plant origin by transesterifying a refined vegetable oil with a charge of a C1-C4 alcohol in the presence of a catalyst and at least 0.2 parts by volume, related to unit volume of refined vegetable oil, of an aliphatic hydrocarbon solvent with a boiling point of ?42° C. to 200° C., comprises mixing the oil, alcohol, catalyst and solvent in a single reaction vessel under homogeneous conditions which promote transesterification to 95-98% completion and which suppress reverse glycerolysis, without stopping transesterification to remove by-product polar glycerol, and without subjecting the oil/fuel mixture to a further transesterification step with a fresh charge of alcohol and catalyst.
    Type: Grant
    Filed: January 29, 2009
    Date of Patent: April 5, 2016
    Assignee: QS Biodiesel Limited
    Inventor: András Kovács
  • Patent number: 9255240
    Abstract: A system and method for the conversion of high free fatty acid (HFFA) containing oils defined as oils containing 20-100% free fatty acids (FFA) and low free fatty acid (LFFA) containing oils defined as oils containing 1-20% free fatty acids (FFA) into oil with less than 0.5% FFA (defined as NFFA oil) includes a combination of partial glycerolysis of HFFA oils to produce LFFA oils and subsequent stripping of LFFA oils to produce NFFA oils via steam distillation.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: February 9, 2016
    Assignee: Technochem International, Inc.
    Inventor: Sanjeev Agarwal
  • Patent number: 9234158
    Abstract: The invention relates to a continuous process for pretreatment of an oil feedstock comprising at most 20% by weight of free fatty acids by esterification of free fatty acids in which a vertical liquid/liquid contactor containing an esterification catalyst in solid form is supplied in counter-current by an alcohol feedstock comprising at least 20% by weight of an alcohol and said oil feedstock, with said contactor being operated at a temperature of between 25 and 120° C., with said contactor performing the contact in liquid-liquid counter-current between a heavy phase and a light phase, with said heavy phase being able to be either an oil-rich phase or an alcohol-rich phase.
    Type: Grant
    Filed: December 15, 2014
    Date of Patent: January 12, 2016
    Assignee: IFP Energies Nouvelles
    Inventors: Vincent Coupard, Laurent Bournay, Eszter Toth, Sylvie Maury
  • Patent number: 9029583
    Abstract: This invention relates to an improved process for the preparation of green fatty acid methyl esters (FAME; commonly called as biodiesel) from different triglyceride oils using mixed metal oxides derived from layered double hydroxides (referred here as LDHs) as reusable solid heterogeneous base catalysts. This process uses very low alcohohoil molar ratio and catalyst and/or products are easily separable after the reaction through simple physical processes. The properties of thus obtained biodiesel meet the standard biodiesel values and can directly be used as transport fuel.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: May 12, 2015
    Assignee: Council of Scientific & Industrial Research
    Inventors: Kannan Srinivasan, Sivashunmugam Sankaranarayanan, Churchil Angel Antonyraj
  • Patent number: 9000197
    Abstract: The invention relates to a continuous method for producing esters, in which at least one polyol ester of formula (I) (R1—COO)mR2 (I), where R1 represents hydrogen or an optionally substituted hydrocarbon group containing 1 to 50 carbon atoms, R2 represents an optionally substituted hydrocarbon group containing 2 to 10 carbon atoms, and m represents a number from 2 to 10 and is smaller than or equal to the number of carbon atoms in R2, is reacted with at least one monohydric alcohol of formula (II) R3—OH (II), where R3 represents an optionally substituted hydrocarbon group containing 1 to 30 C atoms, using microwave radiation in a reaction tube, the longitudinal axis of which extends in the direction of propagation of the microwaves of a single-mode microwave applicator, so as to obtain at least one ester of formula (III) R1—COO—R3 (III), where R1 and R3 have the meanings indicated above.
    Type: Grant
    Filed: September 3, 2010
    Date of Patent: April 7, 2015
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Matthias Krull, Roman Morschhaeuser
  • Patent number: 8980807
    Abstract: A method for producing a high viscosity, low volatiles blown stripped oil blend is provided. The method may include the steps of: (i) obtaining an oil blend of corn stillage oil and soybean oil having a weight ratio of corn stillage oil to soybean oil of from about 1:2 to 3:1; (ii) heating the oil blend to at least 90° C.; (iii) passing air through the heated oil blend to produce a blown oil having a viscosity of at least 50 cSt at 40° C.; and (iv) stripping the blown oil from step (iii) to reduce an acid value of the blown oil to less than 5.0 mg KOH/gram.
    Type: Grant
    Filed: May 20, 2011
    Date of Patent: March 17, 2015
    Assignee: Cargill, Incorporated
    Inventors: Michael John Hora, Patrick Thomas Murphy, John Carl Tolfa
  • Patent number: 8969604
    Abstract: A surfactant composition for agricultural chemicals, containing fatty acid polyoxyalkylene alkyl ether expressed by the following general formula (I), R1CO(EO)m(PO)nOR2??(I) wherein the fatty acid polyoxyalkylene alkyl ether has a narrow ratio of 55% by mass or more, where the narrow ratio is expressed by the following formula (A): Narrow ratio=?i=nMAX?2i=nMAX+2Yi??(A).
    Type: Grant
    Filed: January 15, 2013
    Date of Patent: March 3, 2015
    Assignee: Lion Corporation
    Inventors: Akinori Kanetani, Hiroyuki Izumoto, Shiro Sato, Takaaki Kano
  • 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
  • Publication number: 20150037852
    Abstract: A method for reducing the free fatty acid content of a feedstock includes the steps of providing a free-fatty-acid-containing feedstock, treating the free-fatty-acid-containing feedstock to reduce the free fatty acid content thereof, where the step of treating includes combining at least one of an algae and a coagulant to the free-fatty-acid-containing feedstock, and producing a product from the treated feedstock.
    Type: Application
    Filed: August 4, 2014
    Publication date: February 5, 2015
    Inventors: Lu-Kwang Ju, Majid Hosseini
  • Patent number: 8936922
    Abstract: The present invention provides a novel approach for the preparation of fatty alcohol esters of ?-hydroxy carboxylic acids. In one form of the invention, the target fatty alcohol ester of ?-hydroxy carboxylic acid is produced by converting a lower alkyl ester of ?-hydroxy carboxylic acid into a fatty alcohol ester of ?-hydroxy carboxylic acid via alcoholysis (i.e., transesterification). The transesterification process is an equilibrium reaction, catalyzed chemically (i.e., with acids or bases) or enzymatically, that is shifted in the desired direction to produce the desired product. One way of shifting the reaction in the direction of the desired product is by reducing the concentration of one of the products (e.g., distillation of a lower-boiling alcohol as it is formed). Another preferred way of shifting the reaction in the direction of the desired product is by increasing the concentration of one of the reactants.
    Type: Grant
    Filed: April 11, 2012
    Date of Patent: January 20, 2015
    Assignee: Chemsmart, LLC
    Inventors: Gerald S. Jones, Jr., Scott A. Goodrich, Joseph P. St. Laurent
  • Patent number: 8916721
    Abstract: The present invention is directed to ester compositions which result from the trans-esterification of a triglyceride having an iodine value of between 85 and 175 mg KOH/gm with a fatty alcohol having a melting point of between 35° and 75° C., followed by cooling and removal of the polar phase which results. Surprisingly, we have found the composition has unique properties when used in cosmetic applications.
    Type: Grant
    Filed: June 15, 2012
    Date of Patent: December 23, 2014
    Assignee: SurfaTech Corporation
    Inventors: Thomas G. O'Lenick, Christopher J. Tarletsky
  • Publication number: 20140346414
    Abstract: A dielectric fluid composition for electrical apparatus comprises a functionalized 12-hydroxy stearic acid having desirable properties including a pour point less than ?30° C. and a fire point greater than 250° C. It may be prepared by a process wherein 12-hydroxy methyl stearate is transesterified by reaction with a C3-C20 alcohol to form an alkyl-12-hydroxy stearate, followed by esterification thereof with a linear or branched C4-C20 carboxylic acid. This acid may be a free acid chloride, a fatty acid, a carboxylic acid anhydride, or combination thereof. The resulting functionalized 12-hydroxy stearic acid exhibits improved thermoxidative capability, low temperature flowability, and increased fire point.
    Type: Application
    Filed: September 26, 2012
    Publication date: November 27, 2014
    Applicant: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Suh Joon Han, Dirk B. Zinkweg, Zenon Lysenko
  • Publication number: 20140330033
    Abstract: Apparatus and related methods for reacting a natural oil with a short chain alcohol in the presence of an alkaline catalyst and mesh to produce biodiesel, significantly decreasing the amount of time for the glycerol byproduct to settle out of the reaction mixture. The process for the production of biodiesel includes providing animal or vegetable oil to create a first component, combining a short chain alcohol with a strong base to create a second component, and combining the first and second components together in the presence of a mesh, such that the mesh is in contact with the combined components. The combined compositions represent a reaction mixture that undergo a transesterification reaction and produce fatty acid methyl ester biodiesel and also a glycerol byproduct. The mesh material that is present during the transesterification reaction decreases the amount of time required for the glycerol byproduct to settle out of the reaction mixture.
    Type: Application
    Filed: April 11, 2014
    Publication date: November 6, 2014
    Inventors: JEFFERY THOMPSON, JOHN K. COOPER, MARIO A. OYANADER
  • 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: 8865922
    Abstract: A method of treating tall oil pitch, which comprises sterol esters of fatty acids. According to the present invention, the esters of sterols and fatty acids are broken down, in which case especially formic acid esters or acetic acid esters of sterols are formed instead. The free fatty acids and sterol esters generated are distilled or separated in another way. Use of the present invention increases the yield of fatty acids and also facilitates the separation of sterols from tall oil pitch.
    Type: Grant
    Filed: March 28, 2011
    Date of Patent: October 21, 2014
    Assignee: Forchem Oy
    Inventors: Esko Kiviranta, Juhani Saviainen, Mikko Rintola
  • 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
  • Publication number: 20140252281
    Abstract: A dielectric fluid composition for electrical apparatus comprises a functionalized methyl-12-carboxy methyl stearate having desirable properties including a pour point less than ?30° C. and a fire point greater than 250° C. It may be prepared by a process wherein methyl-12-hydroxy methyl stearate is transesterified by reaction with a C3-C20 alcohol to form the hydroxy methyl ester, followed by reaction with a linear or branched C4-C20 carboxylic acid selected from free acid chlorides, fatty acids, carboxylic acid anhydrides, and combinations thereof. The second step serves to end-cap the hydroxyl groups, thereby producing the functionalized methyl-12-carboxy methyl stearate compound that exhibits improved thermoxidative stability and low temperature flowability, as well as increased fire point.
    Type: Application
    Filed: September 26, 2012
    Publication date: September 11, 2014
    Applicant: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Suh Joon Han, Dirk B. Zinkweg, Zenon Lysenko
  • 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
  • Publication number: 20140194635
    Abstract: A system and method for the conversion of free fatty acids to glycerides and the subsequent conversion of glycerides to glycerin and biodiesel includes the transesterification of a glyceride stream with an alcohol. The fatty acid alkyl esters are separated from the glycerin to produce a first liquid phase containing a fatty acid alkyl ester rich (concentrated) stream and a second liquid phase containing a glycerin rich (concentrated) stream. The fatty acid alkyl ester rich stream is then subjected to distillation, preferably reactive distillation, wherein the stream undergoes both physical separation and chemical reaction. The fatty acid alkyl ester rich stream is then purified to produce a purified biodiesel product and a glyceride rich residue stream. Neutralization of the alkaline stream, formed during the alkali-catalyzed transesterfication process, may proceed by the addition of a mineral or an organic acid.
    Type: Application
    Filed: January 16, 2014
    Publication date: July 10, 2014
    Applicant: REG Seneca, LLC
    Inventors: John P. Jackam, Joel M. Pierce, Jeffrey D. Jones
  • Patent number: 8765985
    Abstract: Blown corn stillage oils and methods for making blown corn stillage oils are disclosed. In one aspect the corn stillage oils are stripped to reduce the acid value of the resulting blown, stripped corn stillage oil. The method includes heating a corn stillage oil to a temperature of at least 90° C., and passing air through the heated oil to produce a blown corn stillage oil having a viscosity of at least 50 cSt at 40° C. In one aspect, the blown corn stillage oil is stripped to reduce the acid value of the blown, stripped corn stillage oil to 5 mg KOH/gram or less.
    Type: Grant
    Filed: May 21, 2010
    Date of Patent: July 1, 2014
    Assignee: Cargill, Incorporated
    Inventors: Michael John Hora, Frank P. Lochel
  • Patent number: 8754247
    Abstract: A catalyst is described which comprises at least one IZM-2 zeolite and at least one matrix, said zeolite having a chemical composition expressed as the anhydrous base in terms of moles of oxides by the following general formula: XO2: aY2O3: bMnO, in which X represents at least one tetravalent element, Y represents at least one trivalent element and M is at least one alkali metal and/or alkaline-earth metal, a and b respectively representing the number of moles of Y2O3 and MnO; and a is in the range 0.001 to 0.5, b is in the range 0 to 1 and n is in the range 1 to 2. Said catalyst is used in various processes for the transformation of hydrocarbon feeds.
    Type: Grant
    Filed: July 21, 2009
    Date of Patent: June 17, 2014
    Assignee: IFP Energies nouvelles
    Inventors: Amandine Cabiac, Nicolas Cadran, Emmanuelle Guillon, Vincent Lecocq, Sylvie Maury
  • Patent number: 8728177
    Abstract: A system and method for the conversion of free fatty acids to glycerides and the subsequent conversion of glycerides to glycerin and biodiesel includes the transesterification of a glyceride stream with an alcohol. The fatty acid alkyl esters are separated from the glycerin to produce a first liquid phase containing a fatty acid alkyl ester rich (concentrated) stream and a second liquid phase containing a glycerin rich (concentrated) stream. The fatty acid alkyl ester rich stream is then subjected to distillation, preferably reactive distillation, wherein the stream undergoes both physical separation and chemical reaction. The fatty acid alkyl ester rich stream is then purified to produce a purified biodiesel product and a glyceride rich residue stream. Neutralization of the alkaline stream, formed during the alkali-catalyzed transesterfication process, may proceed by the addition of a mineral or an organic acid.
    Type: Grant
    Filed: November 30, 2011
    Date of Patent: May 20, 2014
    Assignee: Seneca Landlord, L.L.C.
    Inventors: John P. Jackam, Joel M. Pierce, Jeffrey D. Jones
  • 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: 8703849
    Abstract: Presently disclosed are high purity unsaturated fatty acid esters with an ester moiety characterized by having from five to seven members in a ring structure, which esters when epoxidized find particular utility as primary plasticizers in flexible polyvinyl halide applications. Also disclosed are processes for making the high purity esters.
    Type: Grant
    Filed: January 4, 2011
    Date of Patent: April 22, 2014
    Assignee: Archer Daniels Midland Company
    Inventors: Erik Hagberg, Stephen Howard, George Poppe, Stephen D. Horton
  • 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: 8663345
    Abstract: A system and method for the conversion of free fatty acids to glycerides and the subsequent conversion of glycerides to glycerin and biodiesel includes the transesterification of a glyceride stream with an alcohol. The fatty acid alkyl esters are separated from the glycerin to produce a first liquid phase containing a fatty acid alkyl ester rich (concentrated) stream and a second liquid phase containing a glycerin rich (concentrated) stream. The fatty acid alkyl ester rich stream is then subjected to distillation, preferably reactive distillation, wherein the stream undergoes both physical separation and chemical reaction. The fatty acid alkyl ester rich stream is then purified to produce a purified biodiesel product and a glyceride rich residue stream. Neutralization of the alkaline stream, formed during the alkali-catalyzed transesterfication process, may proceed by the addition of a mineral or an organic acid.
    Type: Grant
    Filed: November 30, 2011
    Date of Patent: March 4, 2014
    Assignee: Seneca Landlord, L.L.C.
    Inventors: John P. Jackam, Joel M. Pierce, Jeffrey D. Jones
  • Patent number: 8624048
    Abstract: The present invention relates to a method of producing alkyl esters and glycerin from a crude or semi-refined vegetable oil and an aliphatic monoalcohol, comprising a deep pretreatment purification stage to eliminate the species based on phosphorus, calcium, magnesium, zinc or iron, insoluble under the temperature conditions of the heterogeneous catalytic reactor.
    Type: Grant
    Filed: December 15, 2010
    Date of Patent: January 7, 2014
    Assignee: IFP Energies Nouvelles
    Inventors: Aurelie Dandeu, Vincent Coupard, Laurent Bournay, Charlotte Rouquette
  • Publication number: 20140005424
    Abstract: A system and method for the conversion of free fatty acids to glycerides and the subsequent conversion of glycerides to glycerin and biodiesel includes the transesterification of a glyceride stream with an alcohol. The fatty acid alkyl esters are separated from the glycerin to produce a first liquid phase containing a fatty acid alkyl ester rich (concentrated) stream and a second liquid phase containing a glycerin rich (concentrated) stream. The fatty acid alkyl ester rich stream is then subjected to distillation, preferably reactive distillation, wherein the stream undergoes both physical separation and chemical reaction. The fatty acid alkyl ester rich stream is then purified to produce a purified biodiesel product and a glyceride rich residue stream. The glycerin rich second liquid phase stream may further be purified to produce a purified glycerin product and a (second) wet alcohol stream.
    Type: Application
    Filed: June 21, 2013
    Publication date: January 2, 2014
    Applicant: REG Seneca, LLC
    Inventors: John P. Jackam, Derek J. Winkel, Jared A. Downey
  • Patent number: 8614074
    Abstract: A process for the preparation of a composition comprising the cis9, trans11 and trans10, cis12 isomers of conjugated linoleic acid (CLA) comprises: providing a mixture comprising cis9, trans11 and trans10, cis12 isomers of conjugated linoleic acid (CLA) in which one of the cis9, trans11 and trans10, cis12 isomers is present in a first weight ratio X of at least 1.3:1 with respect to the other isomer; and subjecting the mixture to crystallization to form a composition comprising the cis9, trans11 and trans10, cis12 isomers in which one of the cis9, trans11 and trans10, cis12 isomers is present at a second weight ratio Y with respect to the other isomer, wherein Y is greater than X.
    Type: Grant
    Filed: April 4, 2007
    Date of Patent: December 24, 2013
    Assignee: Stepan Specialty Products, LLC
    Inventors: Victoria Taran, Krishnadath Bhaggan, Jeroen Monster
  • Publication number: 20130331587
    Abstract: This invention relates to an improved process for the preparation of green fatty acid methyl esters (FAME; commonly called as biodiesel) from different triglyceride oils using mixed metal oxides derived from layered double hydroxides (referred here as LDHs) as reusable solid heterogeneous base catalysts. This process uses very low alcohohoil molar ratio and catalyst and/or products are easily separable after the reaction through simple physical processes. The properties of thus obtained biodiesel meet the standard biodiesel values and can directly be used as transport fuel.
    Type: Application
    Filed: February 10, 2012
    Publication date: December 12, 2013
    Inventors: Kannan Srinivasan, Sivashunmugam Sankaranarayanan, Churchil Angel Antonyraj
  • Patent number: 8580988
    Abstract: A method for producing a high viscosity, low volatiles blown stripped plant-based oil is provided. The method may include the steps of: (i) obtaining a plant-based oil; (ii) heating the oil to at least 90° C.; (iii) passing air through the heated oil to produce a blown oil having a viscosity of at least 50 cSt at 40° C.; (iv) stripping the blown oil from step (iii) to reduce an acid value of the blown oil to from 5 mg KOH/g to about 9 mg KOH/g; (v) adding a polyol to the stripped oil from (iv); and (vi) stripping the oil from step (v) to reduce the acid value of the oil to less than 5.0 mg KOH/g or less.
    Type: Grant
    Filed: May 20, 2011
    Date of Patent: November 12, 2013
    Assignee: Cargill, Incorporated
    Inventors: Michael John Hora, Patrick Thomas Murphy
  • Patent number: 8507702
    Abstract: A method for the continuous production of ester based organic compounds from renewable natural products via supercritical solvent processing in the presence of heterogeneous nano-structured catalysts. Fatty acid triglycerides may therefore be transesterified using heterogeneous nano-structured catalysts in the presence of supercritical alcohols to provide alkyl ester compounds and glycerine.
    Type: Grant
    Filed: March 29, 2011
    Date of Patent: August 13, 2013
    Assignee: Southwest Research Institute
    Inventors: Maoqi Feng, Chee-Kai Tan