Esterification Or Molecular Rearrangement (e.g., Intra- Or Inter-esterification, Etc.) Patents (Class 554/30)
  • Patent number: 9220287
    Abstract: A method for extraction from Lesquerella seeds having an acid value of less than 6 mg KOH/g, said method including the following steps: a seed-processing step i) that includes a single operation of flattening the seeds and at least one operation of drying the seeds; and a step ii) of placing the processed seeds into contact with a mixture of light anhydrous alcohol and co-solvent under temperature and time conditions that are sufficient for extracting a raw oil including phospholipids and gums, as well as obtaining a de-oiled cake.
    Type: Grant
    Filed: September 24, 2012
    Date of Patent: December 29, 2015
    Assignee: ARKEMA FRANCE
    Inventors: Jean-Luc Dubois, Antoine Piccirilli, Julien Magne
  • 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: 8709276
    Abstract: A refrigeration composition containing at least one ester formed by esterification of a hydroxycarboxylic acid component and an alcohol component, the hydroxycarboxylic acid component chosen from hydroxycarboxylic acids comprising more than one carboxylic acid group, hydroxystearic acid, hydroxylauric acid, hydroxydecanoic acid, hydroxyarachidic acid, hydroxypalmitic acid, hydroxylinoleic acid, hydroxyerucic acid, hydroxyarachidonic acid, ricinoleic acid, and combinations thereof, and the alcohol component containing at least one alcohol; and a base oil lubricant chosen from alkylbenzenes, alkylated naphthenics, polyalkylene glycols, polyvinylethers, polyalphaolefins, mineral oils, polyol esters, and combinations thereof.
    Type: Grant
    Filed: February 27, 2012
    Date of Patent: April 29, 2014
    Assignee: Shrieve Chemical Products, Inc.
    Inventors: Liwen Wei, Phil Beckler
  • Patent number: 8575378
    Abstract: Methods of producing plant polyols from plant oils include reacting a plant oil with a designed reactant having one or more nucleophilic functional groups and one or more active hydrogen functional groups in the presence of an addition reaction catalyst in a single reaction step. The resultant polyols may be directly reacted with polyisocyanates to produce polyurethanes.
    Type: Grant
    Filed: July 28, 2009
    Date of Patent: November 5, 2013
    Inventors: Thomas M. Garrett, Xian Xian Du
  • Patent number: 8536357
    Abstract: The invention relates to a process for esterifying free fatty acids in vegetable and animal fat with alcohols over heterogeneous acidic ion exchange resin catalysts at temperatures of 60 to 120° C.
    Type: Grant
    Filed: January 30, 2009
    Date of Patent: September 17, 2013
    Assignee: Bayer Technology Services GmbH
    Inventors: Wulf Dietrich, Dieter Heinz, Leslaw Mleczko, Shaibal Roy, Heinrich Morhenn, Robert Tyron Hanlon
  • Patent number: 8481768
    Abstract: The disclosure provides methods and systems for the production of biodiesel from biological feedstocks such as vegetable oils or animal fats. In particular, the disclosure is directed to the product of biodiesel from seeds such as non-edible oil seeds. Methods for maximizing oil recovery from the feedstocks are provided, as well as methods to convert free fatty acids in the feedstocks into glycerides amenable to transesterification. Thus the methods and systems provide for efficient biodiesel production.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: July 9, 2013
    Assignee: Reliance Life Sciences Pvt. Ltd.
    Inventors: Swaroop Sarangan, Vidhya Rangaswamy
  • Patent number: 8333905
    Abstract: The present invention includes a polyol produced according to the process comprising reacting a multifunctional alcohol with a first multifunctional component to form a reaction product and reacting the reaction product with a vegetable oil to form a polyol. The present invention also relates to the material comprising the reaction product of an A-side and a B-side, wherein the A-side comprises an isocyanate and the B-side comprises the product formed by the process comprising the steps of reacting a multifunctional alcohol with a first multifunctional component to form a precursor polyol and then reacting the precursor polyol with a vegetable oil to form a vegetable based polyol with selectable functionality.
    Type: Grant
    Filed: October 31, 2007
    Date of Patent: December 18, 2012
    Assignee: Tandem Polymers, Inc.
    Inventors: Thomas M. Kurth, Richard A. Kurth, Robert B. Turner, Les P. Kreifels, Todd A. Van Thomme
  • Patent number: 8299281
    Abstract: Provided are processes for making, and processes for using triglycerides as plasticizers. Mixed triglyceride plasticizers can be produced by recovery of linear or branched C4 to C13 aldehydes from a hydroformylation product, oxidation to the acid with oxygen and/or air, recovery of the resulting acid, and esterification with a crude 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. The product selectivity obtained from esterifying with crude glycerol is comparable to that of esterifying with pure glycerol. 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: March 16, 2010
    Date of Patent: October 30, 2012
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Jihad Mohammed Dakka, Edmund J Mozeleski, Lisa Saunders Baugh
  • Patent number: 8268188
    Abstract: A refrigeration composition containing at least one ester formed by esterification of a hydroxycarboxylic acid component and an alcohol component, the hydroxycarboxylic acid component chosen from hydroxycarboxylic acids comprising more than one carboxylic acid group, hydroxystearic acid, hydroxylauric acid, hydroxydecanoic acid, hydroxyarachidic acid, hydroxypalmitic acid, hydroxylinoleic acid, hydroxyerucic acid, hydroxyarachidonic acid, ricinoleic acid, and combinations thereof, and the alcohol component containing at least one alcohol; and a base oil lubricant chosen from alkylbenzenes, alkylated naphthenics, polyalkylene glycols, polyvinylethers, polyalphaolefins, mineral oils, polyol esters, and combinations thereof.
    Type: Grant
    Filed: October 6, 2011
    Date of Patent: September 18, 2012
    Assignee: Shrieve Chemical Products, Inc.
    Inventors: Liwen Wei, Phil Beckler
  • Patent number: 8152870
    Abstract: A method for producing biofuels is provided. A method of making biofuels includes dewatering substantially intact algal cells to make an algal biomass, sequentially adding solvent sets to the algal biomass, and sequentially separating solid biomass fractions from liquid fractions to arrive at a liquid fraction comprising neutral lipids. The method also includes esterifying the neutral lipids, separating a water miscible fraction comprising glycerin from a water immiscible fraction comprising fuel esters, carotenoids, and omega-3 fatty acids. The method also includes obtaining a C16 or shorter fuel esters fraction, a C16 or longer fuel ester fraction, and a residue comprising carotenoids and omega-3 fatty acids. The method includes hydrogenating and deoxygenating at least one of (i) the C16 or shorter fuel esters to obtain a jet fuel blend stock and (ii) the C16 or longer fuel esters to obtain a diesel blend stock.
    Type: Grant
    Filed: April 6, 2011
    Date of Patent: April 10, 2012
    Assignee: Heliae Development, LLC
    Inventor: Aniket Kale
  • Patent number: 8133518
    Abstract: The present invention is concerned with an edible plant oils from which saturated fatty acids were removed and manufacturing process thereof. In order to remove saturated fatty acids from the edible plant oils; 1) Saturated and unsaturated fatty acids bound on same triglyceride molecules of edible plant oils were segregated each other as alkylesters of fatty acids by conventional transesterification reaction in which edible plant oils were treated with large excess of absolute C1˜C8 alkanol under the presence of catalytic amount of alkali- or alkali-earth metal-C1˜C8 alkoxide. 2) The alkyl-esters of mixed fatty acids were treated with C1˜C8 alkanol solution of urea to remove the alkylester of saturated fatty acids by conventional fractional crystallization as urea complexes of saturated fatty acid-alkylesters.
    Type: Grant
    Filed: June 14, 2007
    Date of Patent: March 13, 2012
    Assignee: E. S. Biotech. Co., Ltd.
    Inventors: Byung-Hoon Han, Mi-Kyung Pyo, Eun-Mi Choi, Jeong-Won Kim
  • Patent number: 8123974
    Abstract: Novel refrigeration compositions are disclosed herein. In an embodiment, a refrigeration composition comprises a mixture of an ester of a hydroxycarboxylic acid. The hydroxycarboxylic acid has a chain length ranging from 8 to 22 carbon atoms. The composition also comprises a carrier fluid or base oil, selected from the group consisting of an alkylbenzene, an alkylated naphthenic, a polyalkylene glycol, a polyvinylether, a polyalphaolefin, mineral oil, a polyol ester, and combinations thereof, providing improved fluidity and heat transfer, and enhanced oil return.
    Type: Grant
    Filed: September 13, 2007
    Date of Patent: February 28, 2012
    Assignee: Shrieve Chemical Products, Inc.
    Inventors: Liwen Wei, Phil Beckler
  • Patent number: 8067625
    Abstract: The present invention relates to fatty acid esters of polyols or sulfonated fatty acid esters or sulfonated fatty acid amides containing at least one group Y, where Y stands for CF3—(CH2)a—O—, SF5—, CF3—(CH2)a—S—, CF3CF2S—, [CF3—(CH2)a]2N— or [CF3—(CH2)a]NH—, where a stands for an integer selected from the range from 0 to 5, or formula (I), where Rf stands for CF3—(CH2)r—, CF3—(CH2)r—O—, CF3—(CH2)r—S—, CF3CF2—S—, SF5—(CH2)t— or [CF3—(CH2)r]2N—, [CF3—(CH2)r]NH— or (CF3)2N—(CH2)r—, B stands for a single bond, O, NH, NR, CH2, C(O)—O, C(O), S, CH2—O, O—C(O), N—C(O), C(O)—N, O—C(O)—N, N—C(O)—N, O—SO2 or SO2—O, R stands for alkyl having 1 to 4 C atoms, b stands for 0 or 1 and c stands for 0 or 1, q stands for 0 or 1, where at least one radical from b and q stands for 1, and r stands for 0, 1, 2, 3, 4 or 5, to processes for the preparation of these compounds, and to uses of these surface-active compounds.
    Type: Grant
    Filed: July 2, 2007
    Date of Patent: November 29, 2011
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Wolfgang Hierse, Nikolai (Mykola) Ignatyev, Martin Seidel, Elvira Montenegro, Peer Kirsch, Andreas Bathe
  • Patent number: 8048468
    Abstract: Provided are a glyceride oil composition derived from a fish oil and a preparation method thereof. The composition includes docosahexaenoic acid (DHA) and docosapentaenoic acid (DPA) with a content of 45 to 95% by weight and eicosapentaenoic acid (EPA) with a content of 0.001 to 13% by weight among constituent fatty acids, and a saturated fatty acid having 16 to 18 carbon atoms, which is bonded at 1- and 3-positions, with a content of 0.001 to 5% by weight among constituent fatty acids, in which a weight ratio of docosahexaenoic acid (DHA)/docosapentaenoic acid (DPA) is 0.5 to 8 and a weight ratio of docosahexaenoic acid (DHA)/eicosapentaenoic acid (EPA) is 3.5 to 15. The glyceride oil composition derived from fish oil has nutritional and physiological superiority due to containing a great amount of polyunsaturated fatty acids such as DHA and DPA in a form of glyceride, and can minimize disadvantages of EPA such as inhibition of ?-6 fatty acid metabolism by containing a low amount of EPA.
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: November 1, 2011
    Assignee: Ilshin Wells Co., Ltd.
    Inventors: Dong-Hun Yoon, Kwang-Hoon Yoon, Gi-Wang Han, Moon-Won Lee, Young-Ho Lee, Sang-Hyuk Park
  • Patent number: 8043524
    Abstract: Novel refrigeration compositions comprising at least one ester of a hydroxycarboxylic acid which can have a chain length in the range of from 8 to 22 carbon atoms. The composition can contain a carrier fluid or base oil selected from alkylbenzenes, alkylated naphthenics, polyalkylene glycols, polyvinylethers, polyalphaolefins, mineral oils, polyol esters, and combinations thereof, providing improved fluidity and heat transfer, and enhanced oil return. A method of making a refrigeration composition by preparing at least one ester by esterifying a first component comprising at least one hydroxycarboxylic acid with a second component comprising at least one alcohol and combining the at least one ester with a base oil selected from the group consisting of alkylbenzenes, alkylated naphthenics, polyalkylene glycols, polyvinylethers, polyalphaolefins, mineral oils, polyol esters, and combinations thereof.
    Type: Grant
    Filed: November 29, 2010
    Date of Patent: October 25, 2011
    Assignee: Shrieve Chemical Products, Inc.
    Inventors: Phil Beckler, Liwen Wei
  • Patent number: 8043649
    Abstract: [Purpose] To provide edible fat and oil that can further improve blooming resistance, and chocolate having further improved blooming resistance than that of conventional chocolate. [Constitution] Edible fat and oil obtained by transesterification reaction or esterification reaction and satisfying the following requirements (A) to (D): (A) iodine value: 15 to 29; B) amount of trans fatty acids in the constituent fatty acids: 16 to 29% by mass; (C) amount of lauric acid in the constituent fatty acids: 13 to 28% by mass; and (D) total amount of oleic acid, linoleic acid, and linolenic acid in the constituent fatty acids: less than 10% by mass.
    Type: Grant
    Filed: August 24, 2007
    Date of Patent: October 25, 2011
    Assignee: The Nisshin OilliO Group, Ltd.
    Inventors: Akira Akahane, Yoshiyuki Hatano
  • Publication number: 20110065821
    Abstract: A method is disclosed for making a polyol comprising: fully-epoxidizing a partially hydrogenated vegetable oil to obtain a fully-epoxidized vegetable oil derivative having an iodine value less than 4 g I2/100 gram, an EOC of from 4.0 to 5.7% and a Gardner color value of 2 or less; and then reacting the fully-epoxidized vegetable oil derivative with a ring opener to form a polyol having a hydroxyl number from 40 to 80 mg KOH/gram, a number average molecular weight of at least 1500 Daltons, a dynamic viscosity less than 10 pascal-seconds, and an EOC below 3.0 wt %.
    Type: Application
    Filed: May 13, 2009
    Publication date: March 17, 2011
    Applicant: Cargill, Incorporated
    Inventors: Timothy W. Abraham, William C. Gower
  • Publication number: 20100264015
    Abstract: Transesterification, esterification, and esterification-transesterification (both one-step and two-step) for producing biofuels. The process may be enhanced by one or more of the following: 1) applying microwave or RF energy; 2) passing reactants over a heterogeneous catalyst at sufficiently high velocity to achieve high shear conditions; 3) emulsifying reactants with a homogeneous catalyst; or 4) maintaining the reaction at a pressure at or above autogeneous pressure. Enhanced processes using one or more of these steps can result in higher process rates, higher conversion levels, or both.
    Type: Application
    Filed: April 14, 2010
    Publication date: October 21, 2010
    Inventors: Marc A. Portnoff, David A. Purta, Margaret A. Nasta, Jingfeng Zhang, Faiz Pourarian
  • Patent number: 7781384
    Abstract: The invention relates to a biodegradable functional fluid composition based on vegetable oil. This functional fluid suitable for lubricant, hydraulic and like fluid comprises palm olein and its by-product generated from fractionation of palm oil. The by-product is esterified by a hindered alcohol prior to blend together with palm olein and additive packages. The hydraulic fluid particularly suited for tropical climate with temperature ranging from 15-40° C.
    Type: Grant
    Filed: November 12, 2004
    Date of Patent: August 24, 2010
    Inventors: Yeong Shoot Kian, Ooi Tian Lye, Salmiah Ahmad
  • Patent number: 7754905
    Abstract: A method comprising applying a controlled flow cavitation apparatus to a biodiesel production process in order to increase fatty acid alkyl ester yield. A feedstock comprising free fatty acids can be passed through a controlled flow cavitation apparatus at a velocity capable of generating a hydrodynamic cavitation zone where the free fatty acids can be esterified. One or more controlled flow cavitation apparatuses can be applied at various points of a biodiesel production process.
    Type: Grant
    Filed: July 3, 2008
    Date of Patent: July 13, 2010
    Assignee: Arisdyne Systems, Inc.
    Inventor: Oleg V. Kozyuk
  • Patent number: 7722755
    Abstract: Methods, systems, and devices are provided for synthesizing one or more chemical products from a renewable oil, comprising the step of flowing a fluid which comprises a renewable oil through a high voltage electrical field effective to catalyze a chemical reaction involving the renewable oil. Examples of renewable oils include vegetable oils, animal fats, bio-oils, and combinations thereof. In one embodiment, the fluid further comprises an alcohol mixed with the oil, and the chemical reaction produces biodiesel and an etherified glycerin. In one embodiment, the biodiesel is further reacted to produce acetic acid.
    Type: Grant
    Filed: November 12, 2004
    Date of Patent: May 25, 2010
    Assignee: ECR Technologies, Inc.
    Inventors: J. Alan Lawson, Ahmed A. Baosman
  • Patent number: 7666234
    Abstract: The present invention relates to an improved process for the preparation of biodiesel from triglyceride oils through transesterification, particularly the fatty acid methyl ester of oil mechanically expelled from whole seeds of Jatropha curcas, a plant with potential for cultivation on wastelands in India and other countries, all unit operations being carried out at ambient temperature.
    Type: Grant
    Filed: December 23, 2004
    Date of Patent: February 23, 2010
    Assignee: Council of Scientific and Industrial Research
    Inventors: Pushpito Kumar Ghosh, Subbarayappa Adimurthy, Mahesh Ramnikbhai Gandhi, Nilesh Kumar Kanjibhai Vaghela, Meena Rajnikant Rathod, Bhupendra Dhanvantrai Shethia, Jayant Batukrai Pandya, Rajendra Amrutlal Parmar, Prakash Jagjivanbhai Dodia, Mehul Ghanshyambhai Patel, Dahyabhai Revabhai Parmar, Sanat Natwarlal Patel
  • Patent number: 7592470
    Abstract: A novel process is described for producing esters of linear monocarboxylic acids containing 6 to 26 carbon atoms, by reacting vegetable or animal oils, neutral or otherwise, with monoalcohols containing 1 to 18 carbon atoms in the presence of a catalyst selected from: mixtures of titanium oxide and alumina having formula: (TiOx)y(Al2O3)1-y where x has the value 1.5 to 2.2 and y, representing the weight ratio of the two oxides, has a value of 0.005 to 0.995; mixtures of zirconium oxide and alumina having formula: (ZrOx)y(Al2O3)1-y where x has the value 1.5 to 2.2 and y has a value of 0.005 to 0.995; and mixtures of antimony oxide and alumina having formula: (SbOx)y(Al2O3)1-y where x has the value 1.2 to 2.6 and y has a value of 0.005 to 0.995, in order to directly produce, in one or more steps, an ester for use as a fuel and a pure glycerin.
    Type: Grant
    Filed: May 26, 2004
    Date of Patent: September 22, 2009
    Assignee: Institut Francais du Petrole
    Inventors: Thierry Lacome, Gerard Hillion, Bruno Delfort, Renaud Revel, Serge Leporq, Gustave Acakpo
  • Patent number: 7544763
    Abstract: The present invention relates to a manufacturing process for producing a polyol from a fatty acid ester in-situ. The process does not use any added organic or inorganic acid catalyst. The polyol produced by the process is essentially free of any cation or anion. The fatty acid ester oil epoxidation and hydroxylation reactions can occur progressively in the same reactor for essentially a one-pot reaction. The polyol produced by the process is essentially free of any cation or anion. The polyol can be used to produce polyurethanes having improved properties.
    Type: Grant
    Filed: November 7, 2006
    Date of Patent: June 9, 2009
    Assignee: Arkema Inc.
    Inventor: Mohammad Kazemizadeh
  • Publication number: 20090043118
    Abstract: A method comprising applying a controlled flow cavitation apparatus to a biodiesel production process in order to increase fatty acid alkyl ester yield. A feedstock comprising free fatty acids can be passed through a controlled flow cavitation apparatus at a velocity capable of generating a hydrodynamic cavitation zone where the free fatty acids can be esterified. One or more controlled flow cavitation apparatuses can be applied at various points of a biodiesel production process.
    Type: Application
    Filed: July 3, 2008
    Publication date: February 12, 2009
    Applicant: Arisdyne Systems, Inc.
    Inventor: Oleg V. Kozyuk
  • Publication number: 20080269513
    Abstract: The disclosure provides methods and systems for the production of biodiesel from biological feedstocks such as vegetable oils or animal fats. In particular, the disclosure is directed to the product of biodiesel from seeds such as non-edible oil seeds. Methods for maximizing oil recovery from the feedstocks are provided, as well as methods to convert free fatty acids in the feedstocks into glycerides amenable to transesterification. Thus the methods and systems provide for efficient biodiesel production.
    Type: Application
    Filed: March 28, 2008
    Publication date: October 30, 2008
    Applicant: RELIANCE LIFE SCIENCES PVT LTD.
    Inventors: Swaroop Sarangan, Vidhya Rangaswamy
  • Publication number: 20080250975
    Abstract: A method for preparing a fluxing oil, having an iodine number ranging from 50 to 200, based on fatty substances of natural origin having been chemically functionalized by oxidation, includes the steps of: i) providing a fatty substance or a mixture of fatty substances of natural origin, ii) subjecting the fatty substance or the mixture of fatty substances of natural origin to at least one transesterification or esterification reaction by at least one alkanol or mono-alcohol, iii) subjecting the compound or mixture of compounds obtained at step ii) to at least one chemical functionalization reaction by oxidation introducing at least one functional group selected from carboxylic acid, epoxy, peroxide, aldehyde, ether, ester, alcohol and ketone groups, and iv) collecting the fluxing oil.
    Type: Application
    Filed: October 10, 2006
    Publication date: October 16, 2008
    Applicants: COLAS, VALAGRO, CENTRO DE VALORISATION
    Inventors: Christine Deneuvillers, Le Chien Hoang
  • Patent number: 7323588
    Abstract: The invention relates to isomeric nonyl benzoates, processes for their preparation, mixtures of the same with alkyl phthalate, alkyl adipate, or alkyl cyclohexanedicarboxylate, and also to the use of these mixtures.
    Type: Grant
    Filed: April 18, 2003
    Date of Patent: January 29, 2008
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Michael Grass, Juergen Koch
  • Patent number: 7300966
    Abstract: A process is described for preparing mixtures of diesters of phthalic acid with decanols and tridecanols by reacting phthalic acid or a reactive derivative of phthalic acid with a mixture made from at least one decanol and at least one tridecanol. Mixtures obtainable in this way are also described, as is their use as plasticizers for molding compositions, and also mixtures of isomeric tridecanols suitable for preparing the mixtures of diesters.
    Type: Grant
    Filed: July 4, 2001
    Date of Patent: November 27, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Boris Breitscheidel, Richard Selberdinger, Klaus Rossato, Uwe Storzum, Jürgen Holzmann, Günther Golfier, Walter Disteldorf, Bernd Morsbach, Jarren Peters, Christoph Übler
  • Patent number: 7125950
    Abstract: A solvent-free process for making a polyol fatty acid polyester composition useful for preparation of polyurethanes is described. These compositions are preferably made by reaction of a natural oil (from plant or animal) with a multi-functional hydroxyl compound derived from a natural source, such as sorbitol, in presence of an alkali metal salt or base such as potassium hydroxide as a catalyst which also acts to saponify the reaction mixture. The hydroxyl content of the prepared composition depends on the amount of the multi-functional hydroxyl compound used in the preparation. In another embodiment, the hydroxyl groups of these compositions are reacted with an isocyanate, such as the polymeric diphenylmethane diisocyanate (also known as 4,4?-diphenyl methane diisocyanate, or MDI) to form polyurethanes in a conventional manner.
    Type: Grant
    Filed: April 29, 2004
    Date of Patent: October 24, 2006
    Assignee: Board of Trustees of Michigan State University
    Inventors: Jean-Pierre L. Dwan'Isa, Lawrence T. Drzal, Amar K. Mohanty, Manjusri Misra
  • Patent number: 6797281
    Abstract: Esters of L-carnitine and alkanoyl L-carnitines are described which can be used as cationic lipids for the intracellular delivery of pharmacologically active compounds. New esters of L-carnitine and alkanoyl L-carnitines of formula (I) are also disclosed wherein the R groups are as defined in the description.
    Type: Grant
    Filed: October 9, 2001
    Date of Patent: September 28, 2004
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Claudio Pisano, Maria Ornella Tinti, Mosé Santaniello, Luciana Critelli, Giovanni Salvatori
  • Patent number: 6762313
    Abstract: Processes for preparing linoleic acid raw materials are described wherein the processes comprise: (a) transesterifying a triglyceride component with an alcohol having from 1 to 4 carbon atoms, at a temperature of from 80 to 120° C., to form a transesterification mixture comprising linoleic acid esters and one or more by-products selected from the group consisting of glycerides, free glycerol, and soaps, wherein the triglyceride component is comprised of at least 60% by weight linoleic acid; and (b) removing the one or more by-products from the transesterification mixture.
    Type: Grant
    Filed: March 13, 2003
    Date of Patent: July 13, 2004
    Assignee: Cognis Deutschland GmbH & Co. KG
    Inventors: Albert Strube, Uwe Hoemmerich, Bernhard Gutsche
  • Patent number: 6753032
    Abstract: The plant sterol-containing fat composition of the present invention contains a plant sterol fatty acid ester (A); and from 10 to 70% by weight of a partial glyceride (B). It can provide a cholesterol absorption inhibiting effect, and capable of ensuring no addition of an emulsifier or a reduction in amount of the emulsifier to be added when utilized for production of fat foods in the emulsion product form such as margarines, fat spreads, and whip creams, whereby an emulsion product having no or reduced flavor characteristic of the emulsifier can be obtained.
    Type: Grant
    Filed: November 26, 2001
    Date of Patent: June 22, 2004
    Assignee: Asahi Denka Kogyo Kabushiki Kaisha
    Inventors: Toshiyuki Hirokawa, Kazuaki Suzuki, Shoji Maruzeni
  • Publication number: 20030191274
    Abstract: The present invention includes a method of producing a polyol having increased functionality by reacting a vegetable oil with an alkene oxide and the polyol produced according to the method.
    Type: Application
    Filed: October 10, 2001
    Publication date: October 9, 2003
    Inventors: Thomas M. Kurth, Richard A. Kurth, Robert B. Turner, Les P. Kreifels
  • Patent number: 6630189
    Abstract: A process for fractionating an oil composition containing at least 50% by weight of partial diglycerides into a solid portion and a liquid portion, which includes dissolving an emulsifier in the oil composition, cooling the solution to deposit crystals and then conducting solid-liquid separation. The process permits easily fractionating the oil composition into a solid oil composition and a liquid oil composition.
    Type: Grant
    Filed: July 9, 2001
    Date of Patent: October 7, 2003
    Assignee: Kao Corporation
    Inventors: Masakatsu Sugiura, Minoru Kase, Hiroaki Yamaguchi, Naoto Yamada
  • Patent number: 6599972
    Abstract: Novel latex or emulsion compositions containing internally plasticizing and crosslinkable monomers derived from traditional semi-drying or non-drying oils are disclosed and claimed. The monomers are ethylenically unsaturated derivatives of long-chain olefinic compounds. Preferred embodiments include latex formed from acrylate or methacrylate esters of fatty alcohols. A process for the synthesis of the latex composition is also disclosed, which involves (a) polymerization of the ethylenically unsaturated derivatives of a long-chain olefinic compound in an aqueous phase with at least one other copolymerizable monomer; and (b) blending of so formed polymer with at least one drier and a surfactant to form the novel latex or emulsion compositions. These compositions form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C.
    Type: Grant
    Filed: January 12, 2001
    Date of Patent: July 29, 2003
    Assignee: University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Olan Stanley Fruchey
  • Publication number: 20020007080
    Abstract: Novel compounds derived from traditional semi-drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.
    Type: Application
    Filed: April 10, 2001
    Publication date: January 17, 2002
    Applicant: University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Publication number: 20010031883
    Abstract: Novel compounds derived from traditional semi- drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.
    Type: Application
    Filed: April 10, 2001
    Publication date: October 18, 2001
    Applicant: The University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Patent number: 6278006
    Abstract: Oils containing a triacylglycerol polyol ester and a non-glycerol polyol ester are described, as well as methods of making such oils. Methods for improving lubrication properties of a vegetable oil also are described.
    Type: Grant
    Filed: January 19, 1999
    Date of Patent: August 21, 2001
    Assignee: Cargill, Incorporated
    Inventors: Dharma R. Kodali, Scott C. Nivens
  • Patent number: 6258869
    Abstract: Polyols useful for preparing foamed polyurethane systems are produced by reacting a feed stock of agricultural origin with a multifunctional hydroxyl component in the presence of a catalytically effective amount of a catalyst suitable to polymerize the agricultural feed stock. The reaction may further include a di basic acid, such as phthalic or adipic acid, or a diol, DEG, or PEG. The resultant polyol is then purified and blended with other ingredients to produce a formulated polyol suitable for specific polyurethane foam systems. The polyols produced in accordance with the method are also described.
    Type: Grant
    Filed: July 13, 1999
    Date of Patent: July 10, 2001
    Assignee: Polymermann (Asia) Pvt. Ltd.
    Inventors: Ashvin M. Shah, Tilak M. Shah
  • Patent number: 6238926
    Abstract: A process for modifying a triacylglycerol stock, such as a vegetable oil stock, to better control fluidity is provided. The process includes interesterifying the triacylglycerol stock in the presence of a basic catalyst while monitoring the absorbance of the reaction mixture. A modified triacylglycerol stock produced by partial interesterification as well as plastic spreads and water-in-oil emulsions which include the partially interesterified triacylglycerol stock are also provided.
    Type: Grant
    Filed: September 17, 1997
    Date of Patent: May 29, 2001
    Assignee: Cargilll, Incorporated
    Inventors: Linsen Liu, Daniel Scott Lampert
  • Patent number: 6235916
    Abstract: Novel compounds derived from traditional semi-drying and non-drying oils featuring internally plasticizing and crosslinkable properties are disclosed and claimed. Preferred embodiments include acrylate or methacrylate esters of hydroxy long-chain olefinic compounds derived from castor oil or lesquerella oil. A process for the preparation of the novel compounds is also disclosed, which involves esterification reaction of ethylenically unsaturated carboxylic acids or its derivatives with substituted hydroxy long-chain olefinic compounds. These compounds are suitable for forming latices, which form films at low minimum film forming temperatures (MFT) ranging from −5 to 10° C. and cure to above ambient glass transition (Tg) polymers without the use of traditional organic cosolvents which contribute to environmental pollution via volatile organic compounds (VOCs) emissions. These latices are therefore useful in waterborne coatings, contact and pressure sensitive adhesives, and inks.
    Type: Grant
    Filed: December 24, 1996
    Date of Patent: May 22, 2001
    Assignee: University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Patent number: 6203720
    Abstract: Novel latex or emulsion compositions containing internally plasticizing and crosslinkable monomers derived from traditional semi-drying or non-drying oils are disclosed and claimed. The monomers are ethylenically unsaturated esters of long-chain olefinic compounds. Preferred embodiments include latex formed from acrylate or methacrylate esters of hydroxy fatty acid esters derived from castor oil or lesquerella oil. A process for the synthesis of the latex composition is also disclosed, which involves (a) an esterification reaction of ethylenically unsaturated carboxylic acid or its derivatives with a substituted hydroxy long-chain olefinic compound; (b) subsequent polymerization of the so formed ethylenically unsaturated ester of a long-chain olefinic compound in an aqueous phase with at least one other copolymerizable monomer; and (c) blending so formed polymer with at least one drier and a surfactant to form the novel latex or emulsion compositions.
    Type: Grant
    Filed: December 24, 1996
    Date of Patent: March 20, 2001
    Assignee: University of Southern Mississippi
    Inventors: Shelby Freland Thames, Kamlesh Gopichand Panjnani, Rajan Hariharan, Zhiyu Wang
  • Patent number: 6040161
    Abstract: Liquid oils with a SAFA-content of less than 5 wt % can be obtained by conversion of a fatty compound (A), preferably having a SAFA-level of more then 5 wt %, with a reactant (B), capable of forming different reaction products of the non-triglyceride type (C.sub.1, C.sub.2 etc.) having a different melting point and/or different solubility in compound (A); the SAFA-level of the end product can be controlled by separating the precipitate of the higher melting more saturated reaction-products (C.sub.1, C.sub.2 etc.) from the rest of the reaction mixture.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: March 21, 2000
    Assignee: Loders Croklaan B.V.
    Inventors: Frederick William Cain, Paul Thomas Quinlan, Stephen Raymond Moore
  • Patent number: 5916854
    Abstract: A biodegradable lubricating base oil obtained by carrying out an addition reaction of an alkylene oxide and a transesterification in a mixture of fats and oils, a polyhydric alcohol or an aliphatic carboxylic acid, and an alkylene oxide, the mixture containing 5 to 150 mol of the alkylene oxide to 1 mol of the fats and oils; a biodegradable lubricating base oil obtained by carrying out esterification of all or part of the hydroxyl group in the above fats and oils derivative using an aliphatic carboxylic acid or ester derivative thereof. Further, a biodegradable lubricating oil composition containing the biodegradable lubricating base oil and the use thereof are also described.
    Type: Grant
    Filed: August 7, 1997
    Date of Patent: June 29, 1999
    Assignee: Kao Corporation
    Inventors: Shuichi Inaya, Hiroki Sawada, Yuichiro Kobayashi, Toshiya Hagihara
  • Patent number: 5726331
    Abstract: The present invention relates to a process for the preparation of dimethyl N-lauroyl-L-glutamate by reaction of N-lauroyl-L-glutamic acid with methanol in the presence of trimethyl orthoformate.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: March 10, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Engelhardt, Manfred Muller, Michael Wessling
  • Patent number: 5670348
    Abstract: Liquid oils with a SAFA-content of less than 5 wt % can be obtained by conversion of a fatty compound (A), preferably having a SAFA-level of more then 5 wt %, with a reactant (B), capable of forming different reaction products of the non-triglyceride type (C.sub.1, C.sub.2 etc.) having a different melting point and/or different solubility in compound (A); the SAFA-level of the end product can be controlled by separating the precipitate of the higher melting more saturated reaction-products (C.sub.1, C.sub.2 etc.) from the rest of the reaction mixture.
    Type: Grant
    Filed: March 31, 1995
    Date of Patent: September 23, 1997
    Assignee: Loders-Croklaan B.V.
    Inventors: Frederick William Cain, Paul Thomas Quinlan, Stephen Raymond Moore
  • Patent number: 5654018
    Abstract: The invention concerns a new process for the preparation of novel fats, comprising SUS- and SSU-triglycerides high in behenic acid, wich are predominantly in .beta..sup.1 -crystal form. According to the process a high erucic oil is hydrolyzed to form a dierucic diglyceride, this diglyceride is hydrogenated to dibehenic diglyceride, which is converted enzymically to a reaction-mixture from which the novel fats are separated.
    Type: Grant
    Filed: June 19, 1995
    Date of Patent: August 5, 1997
    Assignee: Loders Croklaan B.V.
    Inventors: Frederick William Cain, Stephen Raymond Moore
  • Patent number: 5569680
    Abstract: A method for treating inflammatory bowel disease in a patient by inhibiting the production of interleukin-8 in intestinal epithelial cells by administering to said patient an enema of an effective amount of tributyrin.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: October 29, 1996
    Assignee: Trustees of the Univ. of Penna
    Inventor: Gary D. Wu
  • Patent number: RE43838
    Abstract: The present invention relates to a process for isolating constituents from organic material, comprising the following process steps: a) freeze-drying of the organic material; b) extracting the constituents with a polar solvent or solvent mixture (A) and an organic solvent or solvent mixture (B), it being possible for the extracts of the extraction with (A) and (B) to form one phase; c) combining the extracts (A) and (B) to give one phase; and d) carrying out an esterification/transesterification in the unpolar phase with an alcohol, the esterification/transesterification being carried out in the presence of a volatile acid; the process being a high-throughput process.
    Type: Grant
    Filed: January 10, 2011
    Date of Patent: December 4, 2012
    Assignee: Metanomics GmbH
    Inventors: Michael M. Herold, Martin Dostler, Ralf Looser, Tilmann B. Walk, Achim Fegert, Martin Kluttig, Britta Lehmann, Silke Klein, Annette Hennig, Joachim Kopka