Processes Of Forming The Compound Patents (Class 554/124)
  • Patent number: 10196585
    Abstract: A method for producing a blown and stripped biorenewable oil is provided. The method may include the steps of (a) heating a biorenewable oil to at least 90° C.; (b) exposing an oxygen containing stream to the heated oil to produce a blown oil having a viscosity of at least 40 cSt at 40° C.; (c) adding a base metal catalyst to the blown oil; and (d) stripping the blown oil from step (c) until the stripped oil has an acid value of from about 1 mg KOH/g to about 20 mg KOH/g; wherein the stripped oil from step (d) has a flash point of at least 220° C.
    Type: Grant
    Filed: August 7, 2017
    Date of Patent: February 5, 2019
    Assignee: CARGILL, INCORPORATED
    Inventors: Todd L. Kurth, Frank P. Lochel, Suzanne Stauduhar, Hassan Ali Tabatabaee
  • Patent number: 10071946
    Abstract: Disclosed are methods for preparing phenolic branched chain fatty acids or alkyl esters thereof, involving subjecting in a pressurized container (a) at least one phenolic compound, (b) unsaturated fatty acids having 6 to 25 carbon atoms, alkyl esters thereof, or mixtures thereof, and (c) H-ferrierite zeolite catalyst in the presence of distilled water or alcohol and a nitrogen atmosphere at a temperature of about 100° C. to about 400° C. and a pressure of about 10 to about 1000 psi, and isolating saturated phenolic branched chain fatty acids or alkyl esters thereof or mixtures thereof. Also disclosed are methods for killing microorganisms on or in an object, involving contacting said object with an effective microorganisms killing amount of a composition comprising phenolic branched chain fatty acids or alkyl esters thereof, and optionally a carrier; the phenolic branched chain fatty acids or alkyl esters thereof may be produced by the methods described herein.
    Type: Grant
    Filed: March 1, 2016
    Date of Patent: September 11, 2018
    Assignee: The United States of America, as Represented by the Secretary of Agriculture
    Inventors: Helen N. Lew, Karen Wagner, Xuetong Fan, Alberto Nunez, Robert A. Moreau, Michael J. Haas, Zongcheng Yan
  • Patent number: 9334225
    Abstract: Process for preparing the vinyl ester of isononanoic acid starting out from 2-ethylhexanol, characterized in that (a) 2-ethylhexanol is dehydrated in the presence of a catalyst to form octene; (b) the octene obtained in step a) is converted into an isononanoic acid having one more carbon atom; and (c) the isononanoic acid obtained in step b) is converted into the corresponding vinyl ester.
    Type: Grant
    Filed: June 19, 2013
    Date of Patent: May 10, 2016
    Assignee: OXEA GMBH
    Inventors: Leif Johnen, Guido D. Frey, Matthias Eisenacher, Kristina Kockrick, Heinz Strutz
  • Patent number: 9328055
    Abstract: Systems and methods are disclosed for refining natural oil feedstocks. In some embodiments, the methods comprise transesterifying glycerides in a natural oil feedstock to provide a transesterified product comprising monounsaturated fatty acid esters and polyunsaturated fatty acid esters. In some embodiments, the methods comprise separating the polyunsaturated fatty acid esters from the monounsaturated fatty acid esters (or vice versa), to provide a separated monounsaturated fatty acid ester composition having a ratio of at least 10 parts by weight of monounsaturated fatty acid esters for every 1 part by weight of polyunsaturated fatty acid esters.
    Type: Grant
    Filed: March 16, 2015
    Date of Patent: May 3, 2016
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Chander Balakrishnan, Yenamandra Viswanath, Efimia Metsi-Guckel, Mary Bjorklund, Yongyou Hu, Jason Bronkema
  • Patent number: 9085524
    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: Grant
    Filed: November 7, 2011
    Date of Patent: July 21, 2015
    Assignee: Emery Oleochemicals GmbH
    Inventors: Heinz Muller, Diana Maker
  • Publication number: 20150087031
    Abstract: The present invention relates to methods of processing lignocellulosic material to obtain hemicellulose sugars, cellulose sugars, lignin, cellulose and other high-value products. Also provided are hemicellulose sugars, cellulose sugars, lignin, cellulose, and other high-value products.
    Type: Application
    Filed: May 3, 2013
    Publication date: March 26, 2015
    Inventors: Robert Jansen, Claire Gregoire, philip Travisano, Lee Madsen, Neta Matis, Yael Har-Tal, Shay Eliahu, James Alan Lawson, Noa Lapidot, Luke Burke, Aharon M. Eyal, Timothy Allen Bauer, Hagit Sade, Paul Mcwilliams, Ziv-Vladimir Belman, Bassem Hallac, Michael Zviely, Yelena Gershinksy, Adam Carden
  • 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
  • Publication number: 20140371477
    Abstract: The present invention relates to recombinant cells, particularly recombinant plant cells, which are capable of producing dihydrosterculic acid and/or derivatives thereof. The present invention also relates to methods of producing oil comprising dihydrosterculic acid and/or derivatives thereof.
    Type: Application
    Filed: December 21, 2012
    Publication date: December 18, 2014
    Applicants: Commomwealth Scientific and Industrial Research Organisation, Grains Research and Delvelopment Corporation
    Inventors: Craig Christopher Wood, Fatima Naim, Surinder Pal Singh, Shoko Okada
  • 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: 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: 8895040
    Abstract: The present invention relates to cosmetic and/or personal care formulations and/or compounds. In one embodiment, the present invention relates to ester compounds that can be used in various personal care formulations and/or compounds. In another embodiment, the present invention relates to branced ester compounds having a molecular weight of at least about 1,500 daltons that can be used in various personal care formulations and/or compounds.
    Type: Grant
    Filed: June 4, 2009
    Date of Patent: November 25, 2014
    Assignee: Lubrizol Advanced Materials, Inc.
    Inventors: Brian J. Vondruska, Peter Frank, Anchuu Wu
  • Patent number: 8884042
    Abstract: The invention is directed to a process for the hydrogenation of unsaturated fatty acids to produce saturated fatty acids, said process comprising hydrogenating the unsaturated fatty acid in the presence of hydrogen and a supported nickel catalyst, said supported nickel catalyst comprising an oxidic support, 5 to 80 wt. % of nickel, calculated as atomic nickel on the weight of the catalyst, 0.1 to 10 wt. % of a copper promoter, calculated as atomic copper on the weight of the catalyst and 1 to 10 wt. % of a group II metal, calculated as metallic oxide on the weight of the catalyst.
    Type: Grant
    Filed: April 21, 2011
    Date of Patent: November 11, 2014
    Assignee: BASF Corporation
    Inventors: Hermanus Johannes Bouwman, Robert Johan Andreas Maria Terörde
  • Publication number: 20140323694
    Abstract: PFRs for running multiphasic processes are disclosed. The PFRs are single or multi-chamber devices having at least three types of regions (a liquid-contacting region, a gas-contacting region and a liquid-collection region), and a porous substrate providing fluid communication at least between the liquid-contacting and gas-contacting regions. Removal of liquid from the porous substrate, such as by collecting the liquid as it flows off the bottom of the porous substrate in the liquid-collection region or such as by evaporation of the liquid from the porous substrate in the evaporation region supports a continuous flow process. Methods of using the PFRs are also disclosed, for example methods of using the PFRs as photobioreactors for cultivating photosynthetic microorganisms, for producing fermentable sugars, for producing ethanol, for fermenting synthesis gas and producing single cell protein from natural gas.
    Type: Application
    Filed: November 13, 2012
    Publication date: October 30, 2014
    Inventors: Marc Gregor Von Keitz, Jimmy Lee Gosse, Stefan Thust, Thomas Harwood
  • Publication number: 20140323750
    Abstract: Corn stillage oil derivatives having values for Gardner color of 10 or less and methods for making the corn stillage oil derivatives are disclosed. In one aspect, the corn stillage oil derivative comprises a heat bleached corn stillage oil. Preferably, the heat bleached corn stillage oil has a value for Gardner color of from 4 to 8. In another aspect, the corn stillage oil derivative comprises a blown corn stillage oil. Preferably, the blown corn stillage oil has a value for Gardner color of from 5 to 8.
    Type: Application
    Filed: July 11, 2014
    Publication date: October 30, 2014
    Applicant: Cargill, Incorporated
    Inventor: Frank P. Lochel
  • Patent number: 8865080
    Abstract: Embodiments of a process for production of biodiesel from a transesterification reaction of alcohol and triglycerides in a multi-zone tubular reactor is disclosed. Alkyl esters and glycerin are formed from reactants in a reaction mixture as the reaction mixture flows through the zones. The zones include an entrance zone, an exit zone, and an intermediate zone between the entrance and exit zones. The zones are characterized by physical properties such as viscosity, density, composition, and flow regime. The entrance and intermediate zones include static mixers that perform structured mixing that increases the conversion and yield. The degree of mixing provided by the mixers is different in the zones to account for differences in physical properties.
    Type: Grant
    Filed: December 29, 2008
    Date of Patent: October 21, 2014
    Assignee: Renewable Energy Group, Inc.
    Inventor: Tom Michael Ashley
  • Patent number: 8858657
    Abstract: A method and system for providing direct conversion of algal biomass. Optionally, the method and system can be used to directly convert dry algal biomass to biodiesels under microwave irradiation by combining the reaction and combining steps. Alternatively, wet algae can be directly processed and converted to fatty acid methyl esters, which have the major components of biodiesels, by reacting with methanol at predetermined pressure and temperature ranges.
    Type: Grant
    Filed: December 21, 2011
    Date of Patent: October 14, 2014
    Assignee: Arrowhead Center, Inc.
    Inventors: Shuguang Deng, Prafulla D. Patil, Veera Gnaneswar Gude
  • 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: 8853435
    Abstract: The present invention includes a nutritional supplement composition that may be used for livestock and the like, as well as to a livestock feed mixture containing same. Also included are methods of preparing the nutritional supplement composition, the livestock feed mixture, as well as methods of providing nutrition to livestock and the like. The livestock feed composition comprises: (a) a solid particulate livestock feed material and (b) a solidified particulate mixture of (i) free fatty acid and (ii) a magnesium salt of a fatty acid, the magnesium salt of a fatty acid being present in an amount in the range of from about 25% to about 55% of the amount of the free fatty acid based upon the theoretical requirement to accomplish the total neutralization of all of fatty acid present.
    Type: Grant
    Filed: May 18, 2012
    Date of Patent: October 7, 2014
    Assignee: Milk Specialties Company
    Inventors: Trevor Tomkins, Steven Lamb
  • Publication number: 20140275593
    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: Application
    Filed: June 3, 2014
    Publication date: September 18, 2014
    Applicant: CARGILL, INCORPORATED
    Inventors: Michael John Hora, Frank P. Lochel
  • Publication number: 20140275592
    Abstract: Disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the isomerization of an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride. Also disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the decarboxylation of an unsaturated organic compound. Also disclosed is the use of a catalyst or catalyst precursor for the dual function isomerization and decarboxylation of an unsaturated fatty acid to an unsaturated organic compound.
    Type: Application
    Filed: March 11, 2014
    Publication date: September 18, 2014
    Applicant: The United States of America, as represented by the Secretary of Agriculture
    Inventors: Rex E. Murray, Kenneth M. Doll, Zengshe Liu
  • Patent number: 8822712
    Abstract: Chemically-modified triglycerides are prepared by reacting epoxidized triglyceride oils with phosphorus-based acid hydroxide or esters. The phosphorus-containing triglyceride derivatives are of the formula: wherein R1?, R2? and R3? are independently selected from C3 to C29 aliphatic fatty acid residues, at least one of which comprising one or both of the derivatized methylene groups of the formula: wherein m is 0, 1 or 2, n is 0 or 1, q is 1, 2 or 3, and R and R? are independently selected from the group consisting of H, straight, branched or cyclic hydrocarbons and substituted hydrocarbons, and aryl groups. The phosphorus-containing triglyceride derivatives so produced have utility as antiwear/antifriction additives for industrial oils and automotive applications.
    Type: Grant
    Filed: August 30, 2011
    Date of Patent: September 2, 2014
    Assignees: The United States of America, as represented by the Secretary of Agriculture, The Penn State Research Foundation
    Inventors: Kenneth M. Doll, Brajendra K. Sharma, Paulo A. Suarez
  • 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: 8791281
    Abstract: The invention is related to a process for production of lignoceric acid from mixtures of long-chain aliphatic alcohols that contain lignoceric alcohol, wherein the process consists in oxidizing the mixture in a biphasic catalytic system using quaternary ammonium peroxotungstophosphate as a catalyst and hydrogen peroxide as an oxidant, followed by several physical or chemical unitary steps to separate and purify the lignoceric acid.
    Type: Grant
    Filed: May 10, 2010
    Date of Patent: July 29, 2014
    Assignee: Pontificia Universidad Catolica de Valparaiso
    Inventors: Miguel Angel Fuenzalida Diaz, Alejandro Markovits Rojas, Miriam Berrios Cornejo, Mabel Keller Mena, Jose Rodrigo Vergara Salinas, Glenda Cea Barcia, Andres Illanes Frontaura, Rolando Arturo Chamy Maggi, Andres Markovits Schersl, Araceli Olivares Miralles, Nadia Veronica Guajardo Ramirez
  • Patent number: 8772517
    Abstract: A composition, which is suitable for the production of stilbene compounds, can be separated from tall oil. It contains esters of pinosylvin or pinosylvin derivatives and it is concentrated in relation to these. Preferably, the composition contains esters of pinosylvin monomethyl ethers, the acid part of which is formed of an inorganic acid or an organic acid, in particular an organic acid, which is present in the crude tall oil or which is generated from this oil during the process of refining it. Typically, such acids are fatty and resin acids and lower alkane acids. With the invention, it is possible to generate, at an industrial scale, product fractions, and the pinosylvin compounds which are separated from the fractions can be used as such or they can be further modified by means of different chemical methods.
    Type: Grant
    Filed: April 14, 2009
    Date of Patent: July 8, 2014
    Assignee: Neste Oil Oyj
    Inventor: Kosti Mokkila
  • 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: 8748641
    Abstract: A process for preparing saturated branched chain fatty acids or alkyl esters thereof involving subjecting unsaturated fatty acids having 10 to 25 carbon atoms, alkyl esters thereof or mixtures thereof to a skeletal isomerization reaction in the presence of water or a lower alcohol at a temperature of about 240° C. to about 280° C. using a combination of a stericly hindered Lewis base and zeolite as a Brönsted or Lewis acid catalyst, and isolating saturated branched chain fatty acids or alkyl esters thereof or mixtures thereof from the reaction mixture obtained by the skeletal isomerization reaction. The yield of said saturated branched chain fatty acids is ?70 wt %. The stericly hindered Lewis base is a tertiary amine or phosphine with linear or branched C1 to C6 alkyl or phenyl groups attached thereto.
    Type: Grant
    Filed: May 5, 2010
    Date of Patent: June 10, 2014
    Assignee: The United States of America, as represented by The Secretary of Agriculture
    Inventors: Helen Ngo, Thomas A. Foglia
  • 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
  • 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: 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: 8692006
    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: Grant
    Filed: August 11, 2008
    Date of Patent: April 8, 2014
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Kevin D. Uptain, Charles Tanger, Hiroki Kaido
  • 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: 8642348
    Abstract: Provided are efficient, cost-effective and water tolerant methods (e.g., single-vial methods) for preparing fatty acid esters from organic matter, including: obtaining organic matter having at least one fat substituent, contacting the organic matter in a reaction mixture with a basic solution under conditions suitable to provide for hydrolytic release of monomeric fatty acids from the at least one fat substituent to provide a base-treated reaction mixture, and esterifying the monomeric fatty acids of the base-treated reaction mixture by acidification of the reaction mixture and treating in the presence of an organic alcohol to provide fatty acid esters. The methods optionally further include, prior to esterifying, neutralizing the base-treated reaction mixture to provide for neutralized fatty acids, separating the neutralized fatty acids from the neutralized reaction mixture, and dissolving the separated fatty acids in the esterification reaction mixture.
    Type: Grant
    Filed: January 10, 2008
    Date of Patent: February 4, 2014
    Assignee: Washington State University
    Inventors: James V. O'Fallon, Charles T. Gaskins, Jan R. Busboom, Mark L. Nelson, Brian J. Kraft
  • Patent number: 8637056
    Abstract: Mixture comprising esters of saturated C16-C18 fatty acid and unsaturated C16-C18 fatty acids with 2-ethyl-hexyl alcohol, said esters being in an amount ranging from 90% to 100% by weight with respect to the total weight of the mixture. The cosmetic compositions containing such a mixture formulated in topical form have a moisturizing, emollient, elasticizing and skin compactness and smoothness improving action.
    Type: Grant
    Filed: October 15, 2009
    Date of Patent: January 28, 2014
    Assignee: Hallstar Italia S.R.L.
    Inventors: Sergio Amari, Edoardo Pallucca
  • 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: 8614343
    Abstract: The present invention discloses a process for the production of a fatty acid/L-carnitine derivative, whereby the educts are reacted in the presence of monochloroacetic acid.
    Type: Grant
    Filed: February 3, 2010
    Date of Patent: December 24, 2013
    Assignee: Lonza Ltd.
    Inventor: Donya Smida
  • Patent number: 8609876
    Abstract: The present invention relates to modification of the chemical structure of ricinoleic acid, which is present to an extent of 85-90% in castor oil into triacyloxy alkyl ester derivatives. Accordingly, 9,10,12-trihydroxy octadecanoic acid rich fatty acid mixture was prepared from castor oil and converted to their alkyl esters followed by acylation of hydroxy groups to get 9,10,12-triacyloxy octadecanoic acid alkyl ester rich fatty acid alkyl esters mixture. The 9,10,12-triacyloxy octadecanoic acid alkyl esters were purified from the crude product and characterized by 1H NMR studies. The crude products were also evaluated for acid value (A.V.), hydroxyl value (H. V.), iodine value (I. V.), viscosity, viscosity index (V.I.), pour point, flash point and copper strip corrosion and found to be potential base stocks for hydraulic, metal working fluids and other industrial fluids.
    Type: Grant
    Filed: May 14, 2009
    Date of Patent: December 17, 2013
    Assignee: Council of Scientific & Industrial Research
    Inventors: Venkata Surya Koppeswara Rao Bhamidipati, Venkata Padmaja Korlipara, Karunakar Reddy Rondla, Satya Bhaskar Potula, Saravanan Krishnasamy, Badari Narayana Prasad Rachapudi
  • 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
  • Publication number: 20130296591
    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
  • Patent number: 8574878
    Abstract: The present disclosure provides methods useful for producing fatty alcohol compositions from recombinant host cells. The disclosure further provides variant fatty acyl-CoA reductase (FAR) enzymes, polynucleotides encoding the variant FAR enzymes, and vectors and host cells comprising the same.
    Type: Grant
    Filed: June 28, 2011
    Date of Patent: November 5, 2013
    Inventors: Behnaz Behrouzian, Louis Clark, Yihui Zhu, Michael Clay, Kristian Karlshoej
  • Patent number: 8568846
    Abstract: Provided are compositions, processes for making, and processes for using neoalkyl polyol esters and triglycerides as plasticizers. In one form, a neoalkylester triglyceride plasticizers can be produced by (i) drying a polyol feedstream; (ii) contacting in a reactor the dried polyol feedstream with a neoacid feedstream under effective temperature, pressure and time to form a neoalkylester plasticizer effluent stream, and (iii) purifying the neoalkylester plasticizer effluent stream to remove unreacted polyol and unreacted neoacid to form a neoalkylester plasticizer. Such plasticizers can be phthalate-free and provide outstanding properties including a suitable melting or pour point, glass transition temperature, low volatility, increased compatibility, increased hydrolytic stability, and excellent low temperature properties in a range of polymeric resins.
    Type: Grant
    Filed: September 13, 2010
    Date of Patent: October 29, 2013
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Jihad Mohammed Dakka, Edmund John Mozeleski, Lisa Saunders Baugh, Jon Edmond Randolph Stanat, Karla Schall Colle, Francisco Manuel Benitez, Peter Stokes James, Allen David Godwin, Carl Robert Beck
  • Publication number: 20130281664
    Abstract: The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e.
    Type: Application
    Filed: October 11, 2011
    Publication date: October 24, 2013
    Inventors: David Milstein, Ekambaram Balaraman, Chidambaram Gunanathan, Boopathy Gnanaprakasam, Jing Zhang
  • Publication number: 20130267450
    Abstract: A composition that includes one or more compounds represented by the formula A(B)x wherein A is the residue of an aromatic compound, B is the residue of an unsaturated hydrocarbon ester, and x is a value of 1 or greater. The composition has a viscosity (Kv100) from 2 to 40 at 100° C., and a viscosity index (VI) from 100 to 200. The disclosure also relates to a process for producing the composition, a lubricating oil base stock and lubricating oil containing the composition, and a method for improving one or more of solubility and dispersancy of polar additives in a lubricating oil by using as the lubricating oil a formulated oil containing the composition. The lubricating oils containing the composition are advantageous as engine oils that can improve engine fuel efficiency.
    Type: Application
    Filed: April 4, 2013
    Publication date: October 10, 2013
    Applicant: ExxonMobil Research and Engineering Company
    Inventors: Abhimanyu O. Patil, Satish Bodige
  • Patent number: 8536373
    Abstract: Improved method of production of 9-(Z)-retinoic acid, in which a) a ?-formyl-crotonic acid C1-C10 alkyl or phenyl ester is reacted with an isolated 9-(Z)—C15-triarylphosphonium salt by the Wittig reaction in the presence of a base to the corresponding 9-(Z)-retinoic acid ester; which b) is then saponified with a base to the corresponding 9-(Z)-retinoic acid carboxylate and then, following protonation with an acid, the desired 9-(Z)-retinoic acid is obtained, and improved method for the enrichment and isolation of the 9-(Z)—C15-triarylphosphonium salt.
    Type: Grant
    Filed: September 27, 2007
    Date of Patent: September 17, 2013
    Assignee: DSM IP Assets B.V.
    Inventors: Michael Stanek, Stefan Essl, Monika Knopp, Erwin Kübel
  • 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: 8501973
    Abstract: This disclosure relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by an olefin metathesis catalyst. According to one aspect, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting, in the presence of a ruthenium alkylidene metathesis catalyst, an olefinic substrate comprised of at least one internal olefin with a cross metathesis partner comprised of an alpha olefinic reactant, under reaction conditions effective to allow cross-metathesis to occur, wherein the reaction conditions include a reaction temperature of at least 35° C. The methods, compositions, reactions and reaction systems herein disclosed have utility in the fields of catalysis, organic synthesis, and industrial chemistry.
    Type: Grant
    Filed: October 15, 2007
    Date of Patent: August 6, 2013
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Yann Schrodi, Richard L. Pederson, Hiroki Kaido, Michael John Tupy
  • 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: 8476350
    Abstract: Provided are compositions, processes for making, and processes for using triglycerides as plasticizers. Triglyceride plasticizers can be produced by recovery of linear or branched C4 to C10 aldehydes from a hydroformylation product, oxidation to the acid with oxygen and/or air, recovery of the resulting acid, and esterification with glycerol, wherein the total carbon number of the triester groups is from 20 to 25 for greater than or equal to 45 wt % of the plasticizer. Such plasticizers can be phthalate-free and provide outstanding properties including a suitable melting or glass transition or pour point, low volatility, increased compatibility, and excellent low temperature properties in a range of polymeric resins.
    Type: Grant
    Filed: December 17, 2009
    Date of Patent: July 2, 2013
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Jihad Mohammed Dakka, Edmund John Mozeleski, Lisa Saunders Baugh, Enock Berluche
  • 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
  • Publication number: 20130129775
    Abstract: Disclosed here are compositions rich in omega-7 fatty acids, including palmitoleic acid, and products rich in omega-7 fatty acids derived from algal biomass. The algae and/or compositions rich in omega-7 fatty acids may be used in products or as ingredients of products. Methods and systems for increasing the production or concentration of omega-7 fatty acids, and isolating omega-7 fatty acids from algal biomass are also disclosed herein.
    Type: Application
    Filed: November 19, 2012
    Publication date: May 23, 2013
    Applicant: HELIAE DEVELOPMENT, LLC
    Inventor: Heliae Development, LLC