Processes Of Forming The Compound Patents (Class 554/124)
  • Patent number: 6395914
    Abstract: A process directed to the preparation of acetals of malondialdehyde by reacting alkylvinyl ethers or esters with ortho formates in the gas phase with a heterogeneous catalyst.
    Type: Grant
    Filed: January 28, 2000
    Date of Patent: May 28, 2002
    Assignee: Creanova, Inc.
    Inventors: Frank Bauer, Chitoor Subramaniam
  • Publication number: 20020062035
    Abstract: The present invention provides a process for producing lower alkyl fatty esters from fatty acids and lower alcohols, wherein lower alkyl fatty esters are produced in higher yield with a reduction in the amount of the remaining fatty acids. The process of the present invention comprises bringing fatty acids into contact with gaseous lower alcohols in fixed bed(s) charged with a weakly acidic solid catalyst by countercurrent operation, by co-current operation and subsequent countercurrent operation or by pseudo-countercurrent operation, thus feeding and reacting the fatty acids and lower alcohols in fixed-bed reactor(s) charged with a weakly acidic solid catalyst to produce lower alkyl fatty esters.
    Type: Application
    Filed: November 21, 2001
    Publication date: May 23, 2002
    Inventors: Nobuhiro Tatsumi, Takanobu Katayama, Osamu Tabata, Taku Mimura, Noriaki Fukuoka, Katsutoshi Yamamoto
  • Patent number: 6361980
    Abstract: The present invention provides a process for preparing a diglyceride, which includes: in an enzyme-packed tower which includes an immobilized lipase preparation, carrying out an esterification reaction between: (1) an acyl group donor selected from the group including a fatty acid, a lower alcohol ester thereof, and a mixture thereof; and (2) an acyl group acceptor selected from the group including glycerol, a monoglyceride, and a mixture thereof; to obtain a reaction fluid from the enzyme-packed tower; reducing a water content or a lower alcohol content in the reaction fluid; and subsequent to the reducing, recirculating the reaction fluid to the enzyme-packed tower, wherein a residence time of the reaction fluid in the enzyme-packed tower is 120 seconds or less; to obtain a diglyceride. According to the present invention, a high-purity glyceride can be provided at a high yield in a short period of time.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: March 26, 2002
    Assignee: Kao Corporation
    Inventors: Masakatsu Sugiura, Hiroaki Yamaguchi, Naoto Yamada
  • Publication number: 20020035282
    Abstract: A process for the carbonate-catalyzed alcoholysis of fatty acid glycerides is disclosed, wherein an alcohol (e.g., a C1-C6 mono-, di- or trialcohol) is reacted with a fatty acid glyceride (e.g., a plant or animal derived triglyceride) at elevated temperatures and superatmospheric pressures to give high yields of the corresponding ester. The preferred catalysts are the alkali metal, alkaline earth metal or zinc carbonates, with calcium carbonate being especially preferred because of its ready availability and physical integrity under reaction conditions. The alcoholysis reaction may be carried out in a single reactor, or on a continuous basis using a plug flow reactor.
    Type: Application
    Filed: March 2, 2001
    Publication date: March 21, 2002
    Inventor: Galen J. Suppes
  • Publication number: 20010053860
    Abstract: A process for the transesterification of fat and/or oil of biological origin by means of alcoholysis comprises the following steps:
    Type: Application
    Filed: June 19, 2001
    Publication date: December 20, 2001
    Inventors: Siegfried Peter, Eckhard Weidner, Hans-Peter Neuner, Ruth Ganswindt
  • Publication number: 20010044550
    Abstract: A process for the branching of saturated and/or unsaturated fatty acids and/or alkyl esters thereof comprises subjecting the fatty acids and/or alkyl esters to a skeletal isomerization reaction using a catalyst comprising a crystalline porous structure having incorporated therein a metal to form metal sites on said catalyst and isolating branched fatty acids, alkyl esters thereof, or mixtures thereof, from a reaction mixture obtained by said skeletal isomerization reaction. The catalyst used in the isomerization reaction is preferably a zeolite catalyst containing metal sites of a Group VIII metal. The process produces a mixture of fatty acids and/or alkyl esters that contain significant quantities of branched molecules.
    Type: Application
    Filed: March 2, 2001
    Publication date: November 22, 2001
    Inventors: Corey James Kenneally, Daniel Stedman Connor
  • Patent number: 6242499
    Abstract: The invention relates to polyglycerol partial esters of saturated or unsaturated, linear or branched fatty acids and polyfunctional carboxylic acids, which are obtainable by esterification of a polyglycerol mixture with saturated or unsaturated, linear or branched fatty acids having 12 to 22 carbon atoms and polyfunctional carboxylic acids having 4 to 54 carbon atoms and a mean functionality of from 2 to 2.4, the degree of esterification of the polyglycerol mixture being between 30 and 75%.
    Type: Grant
    Filed: September 24, 1997
    Date of Patent: June 5, 2001
    Assignee: Goldschmidt AG
    Inventors: Burghard Gruning, Peter Hameyer, Josef Metzelaars, Christian Weitemeyer
  • Patent number: 6225484
    Abstract: The invention relates to an improved process for the preparation of a compound of formula I wherein R1 represents an optionally substituted aryl group, R2 represents an optionally substituted alkyl group, and R3 and R4 each individually represent an alkyl group; which comprises heating a mixture of a compound of formula II an alcohol, a tri-alkoxymethane, an acid and, optionally, an inert diluent.
    Type: Grant
    Filed: August 12, 1999
    Date of Patent: May 1, 2001
    Assignee: American Cyanamid Co.
    Inventors: Werner Simon, Thomas Petry
  • Patent number: 6218556
    Abstract: An electrochemical process for hydrogenating an unsaturated fatty acid, mixtures of two or more fatty acids, or the unsaturated fatty acid constituents of an edible or non-edible oil's triglycerides is performed using a solid polymer electrolyte reactor. Membrane electrode assemblies consist of a cation exchange membrane onto which porous anode and cathode electrodes are attached. As the electrodes are permeable, reactant and products enter and leave the membrane/cathode and membrane/anode reaction zones via the back sides of the electrodes. Hydrogen is generated in situ by the electro-reduction of protons that are formed at the anode and which migrate through the ion exchange membrane for reaction with the fifty acids or fatty acid constituents. In the disclosed process, only protons (H+ ions) carry the current between the anode and the cathode. The need for a supporting electrolyte to conduct electricity has been circumvented.
    Type: Grant
    Filed: November 12, 1996
    Date of Patent: April 17, 2001
    Assignee: The Administrators of the Tulane Educational Fund
    Inventor: Peter N. Pintauro
  • Patent number: 6153772
    Abstract: A cobalt catalytic system that makes it possible to obtain branched compounds from fatty substances by reacting simple olefins on polyunsaturated esters, which may or may not be conjugated, is described.The compounds that are obtained may be hydrogenated and used as lubricant bases.
    Type: Grant
    Filed: July 24, 1998
    Date of Patent: November 28, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Gerard Hillion, Helene Olivier, Katja Siepen, Robert Stern
  • Patent number: 6140514
    Abstract: A process for the preparation of macrocyclic esters or lactones in a two-stage reaction, which entails effecting linear oligomerization of monomers having a number of carbon atoms corresponding to the macrocycle and effecting cyclizing deoligomerization, wherein both steps are conducted in the presence of a complex compound of trivalent iron.
    Type: Grant
    Filed: March 3, 1999
    Date of Patent: October 31, 2000
    Assignee: Huels Aktiengesellschaft
    Inventors: Guenther Koehler, Juergen Chlench
  • Patent number: 6020509
    Abstract: A process for producing a surfactant composition by partially saponifying an alkoxylated triglyceride having the formula: ##STR1## with an alkali metal hydroxide such as sodium hydroxide and recovering a surfactant composition comprising soap and moisturizing agents comprised of alkoxylated monoglycerides and unreacted alkoxylated triglycerides.
    Type: Grant
    Filed: December 22, 1998
    Date of Patent: February 1, 2000
    Assignee: Condea Vista Company
    Inventors: Upali Weerasooriya, Paul A. Filler, Janet L. Watson
  • Patent number: 6013816
    Abstract: Process for the preparation of a linear .omega.-formyl-carboxylic acid or a corresponding linear formylnitrile compound starting from an internally unsaturated C.sub.4 -C.sub.12 carboxylic acid or a corresponding ester or nitrile by means of hydroformylation in the presence of carbon monoxide, hydrogen and a catalyst system, wherein the hydroformylation is carried out in an aqueous medium and in that the catalyst system comprises platinum and a water-soluble organic bidentate ligand.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: January 11, 2000
    Assignee: DSM NV
    Inventors: Onko J. Gelling, Imre Toth
  • Patent number: 6002030
    Abstract: A process is provided for the fatty acid esterification of propoxylated glycerin wherein fatty acids stripped from the esterifier and/or fatty acids stripped from the esterification product are scrubbed by contact with a scrubbing liquid which is maintained at a temperature above the fatty acid melting point.
    Type: Grant
    Filed: May 8, 1998
    Date of Patent: December 14, 1999
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Jon R. Valbert
  • 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: 5906922
    Abstract: The present invention provides a method for introducing nucleic acids into cells. The method involves exposing the cells to a compound having formula (1), in which w is a nucleic acid, x is a peptide or amino acid, y is a linker having a chain length equivalent to 1 to 20 carbon atoms or is absent, R.sub.4 is H ir CH.sub.2 O--R.sub.3 ; and R.sub.1, R.sub.2 and R.sub.3 are the same or different and are either hydrogen, methyl, ethyl, hydroxyl or an acyl group derived from a fatty acid having a carbon chain of 3 to 24 carbon atoms saturated or unsaturated, with the proviso that at least one of R.sub.1, R.sub.2 and R.sub.3 is an acyl group derived from a fatty acid, or to a compound having the formula (2): w . . . xyNHCH.sub.2 CH.sub.2 OR.sub.5, in which w is a nucleic acid, x is a peptide or amino acid, y is a linker having a chain length equivalent to 1 to 20 carbon atoms or absent, R.sub.5 is an acyl group derived from a fatty acid having a carbon chain of 3 to 24 carbon atoms saturated or unsaturated.
    Type: Grant
    Filed: April 16, 1997
    Date of Patent: May 25, 1999
    Assignee: Commonwealth Scientific and Industrial Research Organisation
    Inventors: Robert George Whittaker, Fiona Helen Cameron, Veronika Bender, Minoo Moghaddam, Philip Anthony Jennings
  • Patent number: 5900496
    Abstract: A strain of Pseudomonas Sp. bacterium (NRRL B-18602) has been discovered which is capable of converting oleic acid to the novel compound, 7,10-dihydroxy-8-octadecenoic acid (DOD). The production of DOD is unique in that it involves a hydroxylation at two positions and a rearrangement of the double bond of the substrate molecule. The new multifunctional, long-chain aliphatic acid has potential utility as a plasticizer and as a source of intermediates in the synthesis of specialty chemicals.
    Type: Grant
    Filed: June 18, 1996
    Date of Patent: May 4, 1999
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventor: Ching T. Hou
  • Patent number: 5885643
    Abstract: Hydrogenated canola oils having improved oxidative stability are disclosed. These oils have relatively low levels of trans-fatty acids and saturated fatty acids, yet possess an oxidative stability of greater than 300 AOM hours. Such oils can be produced by hydrogenation of refined, bleached canola oil extracted from Brassicaceae seeds having elevated levels of oleic acid and reduced levels of polyunsaturated fatty acids. Brassica lines producing seeds having such fatty acid profiles are disclosed. Hydrogenated oils may be fractionated to obtain canola oils that are liquid at or below room temperature and have relatively low levels of trans-fatty acids and saturated fatty acids, yet have an oxidative stability of greater than 300 AOM hours.
    Type: Grant
    Filed: May 21, 1996
    Date of Patent: March 23, 1999
    Assignee: Cargill, Incorporated
    Inventors: Dharma R. Kodali, Lorin R. DeBonte, Zhegong Fan
  • Patent number: 5883274
    Abstract: The present invention relates to a process of measuring a cloud point of polyglycerol-fatty acid ester comprising;adding polyglycerol-fatty acid ester to an aqueous solution of a salt, a polyhydric alcohol, or a mixture thereof to prepare a homogeneous aqueous polyglycerol-fatty acid ester solution;heating the obtained homogeneous aqueous solution to allow to change the homogeneous aqueous solution into a heterogeneous aqueous solution; andmeasuring a temperature at which the homogeneous aqueous solution changes into the heterogeneous aqueous solution.
    Type: Grant
    Filed: June 18, 1996
    Date of Patent: March 16, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Kaoru Shioguchi, Hiroshi Kuzui, Akifumi Yuuki
  • Patent number: 5817845
    Abstract: Methods for stereospecific synthesis of 9-cis olefins and retinoids. In one particular aspect, a cis olefin is generated via a lactol ring opening with complete retention of double bond configuration.
    Type: Grant
    Filed: October 9, 1996
    Date of Patent: October 6, 1998
    Assignee: Ligand Pharmaceuticals, Inc.
    Inventors: Steven K. White, Chan Kou Hwang, David T. Winn
  • Patent number: 5808120
    Abstract: A method of synthesizing 9-cis-retinoic acid, all-trans-retinoic acid or 9-nor-retinoic acid is disclosed. The method comprises the steps of adding a Grignard reagent of ##STR1## to 2,2,6 trimethyl cyclohexanone is disclosed. R is a methyl group or H and the CH.sub.2 --OH group is in either the cis or trans orientation relative to the HC.tbd.C- group. The resulting product is converted into retinoic acid. In the preferable form of the present invention, a tritium-labelled retinoic acid is synthesized, wherein the labelling is at the C.sub.20 position. A preparation of tritium-labelled 9-cis-retinoic acid with a specific activity of greater than 65 Ci/mmol is also enclosed. In a most preferred embodiment, the specific activity is greater than 75 Ci/mmol.
    Type: Grant
    Filed: August 22, 1995
    Date of Patent: September 15, 1998
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Praveen K. Tadikonda
  • Patent number: 5808119
    Abstract: Process for esterifying a polyphenolic oligomer extract of plant origin by the action of an acid chloride, the compositions obtained by this process and their use in human therapy or in cosmetics are described. The extract is placed in a liquid medium which is not a solvent for the extract but which is a solvent for the ester(s) to be obtained, so as to obtain a suspension. At least one aliphatic tertiary amine of low boiling point is added to the suspension in the presence of a catalytic amount of at least one organic base other than pyridine. At least one fatty acid chloride is introduced into this mixture, the reaction mixture being stirred at a temperature below 40.degree. C. and then concentrated by evaporation in order to obtain an esterified extract.
    Type: Grant
    Filed: August 23, 1995
    Date of Patent: September 15, 1998
    Assignee: Berkem
    Inventor: Jean Nkiliza
  • Patent number: 5681939
    Abstract: Propoxylated glycerin is esterified with excess fatty acid by a process wherein the temperature is increased incrementally and the pressure is reduced incrementally during the course of esterification while removing the water formed as a by-product. Rapid conversion of the hydroxyl groups of the propoxylated glycerin is achieved while minimizing losses of fatty acid. The fatty acid-esterified propoxylated glycerin obtained thereby is useful as a reduced calorie fat substitute.
    Type: Grant
    Filed: August 22, 1995
    Date of Patent: October 28, 1997
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Michael R. Ferenz
  • Patent number: 5508456
    Abstract: Methods for the synthesis of 9-cis monotritium-labeled retinoids, and their use in the discovery of Retinoid X Receptor ligands are provided. In addition, 9-cis monotritium-labeled retinoids, as well as novel intermediates and tritium-labeled intermediates formed during the synthesis of 9-cis monotritium-labeled retinoids are also provided.
    Type: Grant
    Filed: May 27, 1994
    Date of Patent: April 16, 1996
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventor: Marcus F. Boehm
  • Patent number: 5502226
    Abstract: A new synthesis of .omega.-hydroxy acids, which employs commercially available starting materials and lowers the cost of production. The process involves coupling a fatty acyl group by enamine chemistry, followed by a ring expansion and selective reduction of ketoacid.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: March 26, 1996
    Assignee: Elizabeth Arden Co., Division of Conopco, Inc.
    Inventors: Suk H. Cho, Victor DeFlorio
  • Patent number: 5498738
    Abstract: The present invention a process for the preparation of a compound of the formula (X) useful as precursor for the A-ring in taxanes ##STR1## wherein R' is an ##STR2## in which R" is a linear, branched or cyclic alkyl group of 1 to 10 carbon atoms. The invention further relates to the novel compound (X) and to novel intermediates in said process.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: March 12, 1996
    Inventors: Esko Karvinen, Ari Koskinen
  • Patent number: 5476956
    Abstract: Co dimerization is conducted of at least one monoolefin, for example a monoolefinic hydrocarbon such as ethylene, propylene or 1-butene, a halogenated monoolefin such as vinyl chloride, or an olefinic functional compound such as methyl acrylate, acrylonitrile, allyl acetate or vinyl acetate, with at least one polyolefin containing at least two conjugated or unconjugated ethylene bonds, for example a diene hydrocarbon such as 1,3-butadiene, piperylene, or isoprene or a polyolefin containing a carboxylic function, such as a fatty acid or a fatty acid ester having 14 to 24 carbon atoms in the fatty chain derived, for example, from a natural oil. The reaction is carried out in the presence of a catalytic system having general formula [RhX.sub.4 ][YR.sub.4 ] where X represents a halogen ion or a SO.sub.4.sup.--, SO.sub.3.sup.-, OH.sup.-, OR.sup.- or R.sup.
    Type: Grant
    Filed: April 25, 1994
    Date of Patent: December 19, 1995
    Assignee: Institut Francais Du Petrole
    Inventors: Gerard Hillion, Robert Stern, Abakar Kotoko, Yves Chauvin
  • Patent number: 5405974
    Abstract: A process for producing a lactone or an ester represented by the following general formula (2), wherein R.sup.1 and R.sup.2, identical or different, each represents (C.sub.1 --C.sub.20) alkyl group; alkyl group substituted with a terminal alkenyl, halogen, alkoxy, phenoxy or acyloxy; phenyl group; or phenyl group substituted with alkyl, halogen, alkoxy, phenoxy or acyloxy; phenylalkyl group; or phenylalkyl group substituted with alkyl, halogen, alkoxy, phenoxy or acyloxy; provided that when R.sup.1 and R.sup.2, identical or different, each represents unsubstituted alkyl group or alkyl group substituted with a terminal alkenyl, halogen, alkoxy, phenoxy, acyloxy or phenyl, the respective alkyl parts of R.sup.1 and R.sup.2 may be conjunct to each other; which comprises reacting a ketone represented by the following general formula (1), wherein R.sup.1 and R.sup.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: April 11, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shun-Ichi Murahashi, Yoshiaki Oda
  • Patent number: 5352812
    Abstract: The metathesis of functionalized and unfunctionalized acyclic olefins using catalyst compositions containing iridium and silver in a molar ration of 3 to 1.
    Type: Grant
    Filed: July 8, 1993
    Date of Patent: October 4, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Jerald Feldman, Marcia B. France
  • Patent number: 5334736
    Abstract: A method to functionalize carbohydrate derivatives by base-induced .beta.-elimination and subsequent olefination to form biologically active products containing .alpha.-hydroxy-diene or .alpha.,.beta.-dihydroxy-diene subunits. Also disclosed are methods to prepare biologically active derivatives of fatty acids containing .alpha.-hydroxy-diene groups and .alpha.,.beta.-dihydroxy-diene groups from derivatives of 2-deoxyfuranoses and derivatives of 2-deoxypyranoses, respectively.
    Type: Grant
    Filed: May 16, 1991
    Date of Patent: August 2, 1994
    Assignee: University of Texas System Board of Regents
    Inventors: Lumin Sun, John R. Falck