Selective Hydrogenation (e.g., Of Polyunsaturated To Monounsaturated, Of Acetylenic To Ethylenic Compound, Etc.) Patents (Class 554/145)
  • Patent number: 10208271
    Abstract: Process for the catalytic hydrogenation of vegetable oils wherein the oil is placed in contact with molecular hydrogen in the presence of a metal catalyst, and the process is performed in the absence of water or in the presence of a quantity of water equal to or less than 5:1 with respect to the weight of the metal catalyst and at a temperature equal to or less than 50° C.
    Type: Grant
    Filed: December 21, 2015
    Date of Patent: February 19, 2019
    Assignee: NOVAMONT S.P.A.
    Inventors: Giampietro Borsotti, Luigi Capuzzi, Francesca DiGioia
  • Patent number: 10087132
    Abstract: Disclosed herein are processes for converting an unsaturated fatty acid into a saturated branched-chain fatty acid through a zeolite-catalyzed process and methods of economically regenerating and reusing the zeolite catalyst. The processes include subjecting the unsaturated fatty acid to an isomerization reaction to result in a selective conversion of the unsaturated fatty acid into the saturated branched-chain fatty acid. The reaction occurs in the presence of (i) an activated zeolite catalyst, (ii) an effective amount of water, and (iii) optionally an oligomerization reducing agent. The spent zeolite catalyst may be regenerated by heating to create a regenerated zeolite catalyst that is functional for use as the activated zeolite catalyst.
    Type: Grant
    Filed: December 29, 2016
    Date of Patent: October 2, 2018
    Assignee: The United States of America, as represented by The Secretary of Agriculture
    Inventors: Majher I Sarker, Helen N. Lew, Robert A. Moreau
  • Patent number: 9347067
    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: Grant
    Filed: December 21, 2012
    Date of Patent: May 24, 2016
    Assignee: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
    Inventors: Craig Christopher Wood, Fatima Naim, Surinder Pal Singh, Shoko Okada
  • Patent number: 9096490
    Abstract: The subject matter of the invention is a process for synthesizing a saturated long-chain ?,?-amino ester (acid) obtained in a first step by cross-metathesis between an acrylic first compound and a monounsaturated second compound comprising at least one nitrile, acid or ester trivalent function, one of these compounds comprising a nitrile function and the other an acid or ester function, in the presence of a ruthenium carbene metathesis catalyst, and in a second step by hydrogenation of the monounsaturated nitrile ester (acid) obtained in the presence of the metathesis catalyst of the preceding stop, acting as a hydrogenation catalyst.
    Type: Grant
    Filed: May 9, 2011
    Date of Patent: August 4, 2015
    Assignees: ARKEMA FRANCE, UNIVERSITE DE RENNES 1, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
    Inventors: Jean Luc Couturier, Jean Luc Dubois, Xiaowei Miao, Cedric Fischmeister, Christian Bruneau, Pierre Dixneuf
  • Publication number: 20140336397
    Abstract: A method for preparing 13C labeled docosahexaenoic acid (DHA) represented by Formula A: The method comprises the conversion of 2-pentyn-1-ol to 13C labeled DHA by reaction with propargyl alcohol, 13C labeled propargyl alcohol and methyl pent-4-ynoate. The various steps involved include tosylation, coupling, bromination, selective hydrogenation and ester hydrolysis to obtain the final product.
    Type: Application
    Filed: November 16, 2012
    Publication date: November 13, 2014
    Inventors: M. Amin Khan, Paul L. Wood, Dayan Goodenowe
  • Patent number: 8614344
    Abstract: Disclosed are improved methods for conducting metathesis utilizing polyunsaturated fatty acid compositions (e.g., polyunsaturated fatty acid polyol esters, polyunsaturated fatty acids, polyunsaturated fatty esters, and mixtures), such as those found in naturally occurring oils and fats, as the starting material. The inventive methods involve hydrogenation of polyunsaturated fatty acid compositions prior to metathesis, thereby providing partially-hydrogenation compositions having a relatively higher amount of monounsaturated fatty acid species. The partially hydrogenated composition can then be subjected to metathesis to provide a metathesis product composition containing industrially useful compounds.
    Type: Grant
    Filed: October 15, 2007
    Date of Patent: December 24, 2013
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Hiroki Kaido, Michael John Tupy, Richard L. Pederson, Yann Schrodi
  • Patent number: 8263794
    Abstract: Disclosed is a process for the manufacture of unsaturated fatty acid alkyl esters or glycerides having a total content of C18:1 of about 30 to about 80 Mol-%, by partial hydrogenation of unsaturated fatty acid esters having a total content of (C18:2+C18:3) of at least 65 Mol-%, calculated on the total amount of C18 moieties in the ester, wherein the hydrogenation is conducted in an aqueous/organic two-phase system in the presence of a water-soluble catalyst consisting of a Group VIII, Group IX, or Group X metal and a hydrophilic ligand.
    Type: Grant
    Filed: October 2, 2007
    Date of Patent: September 11, 2012
    Assignee: Cognis IP Management GmbH
    Inventors: Georgios Papadogianakis, Achilleas Bouriazos, Konstandinos Mouratidis, Nikolas Psaroudakis
  • Patent number: 8211486
    Abstract: The invention is directed to a process for the hydrogenation of unsaturated triglycerides in the presence of a supported precious metal catalyst and hydrogen, in which process a precious metal catalyst is used, comprising an aggregate of solid support, precious metal nano particles and surfactant or polymer.
    Type: Grant
    Filed: May 9, 2005
    Date of Patent: July 3, 2012
    Assignee: BASF Corporation
    Inventors: Annemarie Elisa Wilhelmina Beers, Pieter Hildegardus Berben
  • Publication number: 20100094034
    Abstract: Disclosed are improved methods for conducting metathesis utilizing polyunsaturated fatty acid compositions (e.g., polyunsaturated fatty acid polyol esters, polyunsaturated fatty acids, polyunsaturated fatty esters, and mixtures), such as those found in naturally occurring oils and fats, as the starting material. The inventive methods involve hydrogenation of polyunsaturated fatty acid compositions prior to metathesis, thereby providing partially-hydrogenation compositions having a relatively higher amount of monounsaturated fatty acid species. The partially hydrogenated composition can then be subjected to metathesis to provide a metathesis product composition containing industrially useful compounds.
    Type: Application
    Filed: October 15, 2007
    Publication date: April 15, 2010
    Inventors: Hiroki Kaido, Michael John Tupy, Richard L. Pederson, Yann Schrodi
  • Patent number: 7629478
    Abstract: A process for preparing palm-based polyol monomer includes reacting unsaturated fatty acids or its corresponding triglycerides with polyhydric alcohol. In particular, one example uses oleic acid with about 70% purity as the starting material for preparing the polyol monomer. Moreover, another example uses refined, bleached, and deodorized (RBD) palm olein as an alternative to oleic acid as the starting material. The preparation of the polyol monomer involves the production of monoglyceride of unsaturated fatty acids, which was further epoxidized with peracid and finally ring opened with polyhydric alcohols. Such polyol monomer is used as a raw material for the production of various types of polyurethane products.
    Type: Grant
    Filed: November 6, 2006
    Date of Patent: December 8, 2009
    Assignee: Malaysian Palm Oil Board (MPOB)
    Inventors: Hoong Seng Soi, Nur Musyahadah Mazalan, Mohd Nurhisham Sattar, Tuan Noor Mazne Tuan Ismail, Hazimah Abu Hassan, Ooi Tian Lye, Salmiah Ahmad, Mohd Basri Wahid, Tan Sri Datuk Yusof Basiron
  • Publication number: 20080091039
    Abstract: A hydrogenation process for producing high monoene compositions is disclosed. In particular, a catalyst comprising basic copper carbonate is used for the selective hydrogenation of oils that contain unsaturated fatty acyl components such as unsaturated vegetable oils. Hydrogenation according to the methods of the invention yield high monoene compositions that are useful for industrial applications, such as lubricants.
    Type: Application
    Filed: October 12, 2007
    Publication date: April 17, 2008
    Applicant: Archer-Daniels-Midland Company
    Inventor: Ronald T. SLEETER
  • Patent number: 7244860
    Abstract: Compounds of the formula (I), in which R1 is C1-C4alkyl, C6-C10aryi or C7-C11, aralkyl, R2 is an open-chain or cyclic secondary amino group, and R is a radical of the formula in which R3 is C1-C4alkyl or C1-C4alkoxy, and R4 is H, C1-C4alkyl or C1-C4alkoxy, are ligands for metal complexes as homogeneous hydrogenation catalysts for prochiral organic compounds containing double bonds, by means of which a very high activity and productivity and also enantioselectivity can be achieved
    Type: Grant
    Filed: May 7, 2004
    Date of Patent: July 17, 2007
    Assignee: Umicore AG & Co. KG
    Inventors: Felix Spindler, Matthias Lotz, Marc Thommen
  • Patent number: 7098353
    Abstract: The present invention generally relates to a process for the skeletal isomerization of unsaturated linear fatty acids and/or alkyl esters thereof to their branched counterparts. Said skeletal isomerization process comprises contacting said unsaturated linear fatty acids and/or alkyl esters thereof with at least one metal ion exchanged solid material catalyst. The present invention also relates to a process for the preparation of branched fatty acids and/or alkyl esters thereof from their straight chain counterparts. Finally, the invention also relates to various derivatives prepared from the branched fatty acids and/or alkyl esters prepared in accordance with the present invention.
    Type: Grant
    Filed: April 11, 2003
    Date of Patent: August 29, 2006
    Assignee: Akzo Nobel N.V.
    Inventors: Zongchao Zhang, Shuguang Zhang
  • Patent number: 6998495
    Abstract: A method for producing an optically active 3,5-dihydroxyhexanoic acid derivative by stereoselectively reducing an optically active 3-oxo-5-hydroxyhexanoic acid derivative is provided. The method, which requires neither an ultralow-temperature reactor, an incubator, nor protection of the 5-position hydroxy group, is simple and economical. An optically active 3,5-dihydroxyhexanoic acid derivative is produced by asymmetrical hydrogenation of an optically active 3-oxo-5-hydroxyhexanoic acid derivative catalyzed by an RuBr2BINAP complex prepared from a ruthenium complex and a ruthenium-optically active phosphine complex, i.e., 2,2?-bisdiarylphosphino-1,1?-binaphthyl (BINAP), while using extremely inexpensive hydrogen as the reductant.
    Type: Grant
    Filed: October 24, 2002
    Date of Patent: February 14, 2006
    Assignee: Kaneka Corporation
    Inventors: Masanobu Sugawara, Kenji Inoue
  • Patent number: 6831184
    Abstract: The present invention relates to a process for the skeletal isomerization of unsaturated linear fatty acids to branched fatty acids which comprises contacting said unsaturated linear fatty acids with at least one large pore zeolite catalyst wherein said at least one zeolite catalyst comprises a material having a three dimensional channel structure having a pore diameter of at least 6.0 Å. In another embodiment, the invention relates to a process for the skeletal isomerization and hydrogenation of unsaturated linear fatty acids to saturated branched fatty acids which comprises contacting said unsaturated linear fatty acids with at least one metal-zeolite catalyst.
    Type: Grant
    Filed: June 21, 2002
    Date of Patent: December 14, 2004
    Assignee: Akzo Nobel N.V.
    Inventors: Shuguang Zhang, Zongchao Zhang, Dale Steichen
  • Patent number: 6800773
    Abstract: The invention is directed to a process for carrying out a chemical reaction in a reactor, comprising passing a reaction mixture in liquid phase through at least one structured reactor element present in said reactor, the internal surface of said reactor element that comes into contact with the reaction mixture being catalytically active, the improvement comprising passing said reaction mixture through the said at least one reactor element, said reaction mixture comprising at least one liquid and at least one gas in liquid phase.
    Type: Grant
    Filed: November 25, 2002
    Date of Patent: October 5, 2004
    Assignee: Engelhard Corporation
    Inventors: Bernard Hendrik Reesink, Marius Vaarkamp
  • Patent number: 6455716
    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: Grant
    Filed: March 2, 2001
    Date of Patent: September 24, 2002
    Assignee: The Proctor & Gamble Company
    Inventors: Corey James Kenneally, Daniel Stedman Connor
  • Patent number: 6316646
    Abstract: A process for the continuous catalytic conversion of organic compounds, that, together with unwanted attendant materials, form a starting substance: first the organic compounds of the starting material are purposely extracted by means of condensed fluids. Then the extract, containing the condensed fluids and organic compounds as the reaction mixture is contacted with a catalyst for the catalytic conversion of the organic compounds to form a product mixture, which contains the individual products of the catalytic conversion. The product mixture is separated from the reaction mixture and the fluids employed are, optionally, conducted back for extraction.
    Type: Grant
    Filed: May 7, 1998
    Date of Patent: November 13, 2001
    Assignee: Degussa AG
    Inventors: Thomas Tacke, Stefan Röder, Inge Beul, Steffen Laporte, Peter Panster
  • Patent number: 6284925
    Abstract: The use of the ligands and complexes of general formula I and II for catalytic, enantioselective hydrogenation.
    Type: Grant
    Filed: June 18, 1999
    Date of Patent: September 4, 2001
    Assignee: Degussa-Huls AG
    Inventors: Paul Knochel, Juan Jose Almena Perea, Karlheinz Drauz, Ingo Klement
  • Patent number: 6261692
    Abstract: The present invention relates to a method for preparing a carbon-carbon composite. The method of the present invention comprises adding a ceramic-based oxidation inhibitor having a brittle-to-ductile transition, to thereby eliminate high densification processes via re-impregnation and re-carbonization. The present invention also relates to a carbon-carbon composite prepared thereby that comprises a ceramic powder added to a thermosetting resin.
    Type: Grant
    Filed: December 31, 1998
    Date of Patent: July 17, 2001
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Soo-Jin Park, Jae-Rock Lee, Min-Seok Cho
  • Patent number: 5962711
    Abstract: A typical traditional reactor for hydrogenation consists of a tank filled with a liquid and a gas and a small particle catalyst. The reaction is carried out at high pressures and high temperatures. Lack of gas on the catalyst surface limits the velocity of reaction. Much work has been done to increase the quantity of gas on the catalyst. It has not been possible to solve this problem effectively with the techniques of today. According to the invention an extra solvent is added to the reaction mixture. By bringing the whole mixture (solvent, substrate, hydrogen and reaction products) to super-critical or near-critical state, a substantially homogeneous mixture can be obtained. By this method it is possible to control the concentration of gas on the catalyst to the desired level. The velocity of reaction is thereby increased considerably. The hydrogenation reactions principally involved comprise hydrogenation of carbon-carbon double bonds (C.dbd.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: October 5, 1999
    Assignee: Poul Moller Ledelses- OG Ingeniorradgivning APS
    Inventors: Magnus Harrod, Poul M.o slashed.ller
  • Patent number: 5861521
    Abstract: Esters of unsaturated fatty acids or mixtures thereof can be hydrogenated by a catalysed liquid-phase hydrogenation with hydrogen to give saturated or partially saturated esters of fatty acids or ester mixtures of fatty acids by carrying out the hydrogenation continuously at a pressure of 50 to 350 bar and a reaction temperature of 40 to 150.degree. C. on oxygen-free and support-free shaped bodies which are arranged in a fixed bed and made of pressed powders of elements of the iron subgroup of subgroup VIII of the Periodic Table of the Elements or their alloys with each other or their alloys with elements of subgroup VI; in addition, hydrogenation-inert elements can be present. The shaped bodies have a compressive strength of 20 to 250N on the curved shaped body surface and have an internal surface area of 10 to 90 m.sup.2 /g.
    Type: Grant
    Filed: October 20, 1995
    Date of Patent: January 19, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventor: Gerhard Darsow
  • Patent number: 5693835
    Abstract: A method for preparing fish oil having decreased fish odor, which comprises slightly hydrogenating fish oil to have decrease rate of iodine value of 15% or less and decrease rate of highly unsaturated fatty acid of 33% or less. A method for preparing fish oil having decreased fish odor, which comprises slightly hydrogenating fish oil under the following non-selective conditions: (1) an amount of catalyst used in the hydrogenation is 0.05% by weight or more to an amount of the fish oil; (2) hydrogen pressure in gaseous phase at the beginning of the hydrogenation is 3 kg/cm.sup.2 or more; (3) reaction temperature of the hydrogenation is in the range from 90.degree. to 150.degree. C.; (4) reaction time of the hydrogenation is in the range from 5 to 30 minutes. The fish oil is preferably sardine oil, mackerel oil, skipjack oil, tuna oil, skipjack orbital fat or tuna orbital fat.
    Type: Grant
    Filed: January 26, 1995
    Date of Patent: December 2, 1997
    Assignee: Snow Brand Milk Products Co., Ltd.
    Inventors: Hiroaki Konishi, Kiyoshi Tatsumi, Norifumi Sato
  • Patent number: 5677473
    Abstract: A process for preparing branched chain fatty acids or alkyl esters thereof comprising at least a step wherein unsaturated fatty acids having 10 to 25 carbon atoms, alkyl esters thereof or mixtures thereof are subjected to skeletal isomerization reaction in the presence of water or a lower alcohol at a temperature of 150.degree. to 350.degree. C. using a zeolite as a catalyst, the zeolite having a linear pore structure of pore size that is small enough to retard dimerization and large enough to allow diffusion of the branched chain fatty acids or alkyl esters thereof.
    Type: Grant
    Filed: May 17, 1995
    Date of Patent: October 14, 1997
    Assignee: Kao Corporation
    Inventors: Takeshi Tomifuji, Hiroshi Abe, Yoshihisa Matsumura, Yasumitsu Sakuma
  • Patent number: 5391786
    Abstract: Light-colored ester sulfonates can be obtained by sulfonation of fatty acid lower alkyl esters and subsequent working up providing fatty acid esters having a low content of oxo compounds and unsaturated compounds are used in the sulfonation stage.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: February 21, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Bernd Fabry, Ulrich Kratzel, Wolfgang Schmidt, Guenter Kreienfeld
  • Patent number: 5292907
    Abstract: The invention relates to a process for the manufacture of 6-trans-leukotriene B.sub.4 (LTB.sub.4) of formula ##STR1## in which a butadienediol is prepared; the hydroxyl groups are esterified to produce a diester and this diester is subjected to a stereospecific reductive elimination using low valency titanium [Ti(0)] to produce a 6-trans triether of formula: ##STR2## the groups --OA in positions 5 and 12 of which are then converted to --OH groups and the group --CH.sub.2 OA in position of which is then converted to a --COOH group, to produce 6-trans-LTB.sub.4.The invention also relates to intermediates obtained in the said manufacturing process.
    Type: Grant
    Filed: July 20, 1993
    Date of Patent: March 8, 1994
    Assignee: L'Oreal
    Inventors: Jean Maignan, Guy Solladie, Guy Stone
  • Patent number: 5118837
    Abstract: A modified ruthenium catalyst can be used to selectively hydrogenate an olefinic double bond in the presence of another olefinic double bond in the same or in a different molecule. Modifiers are selected from compounds containing trivalent nitrogen, trivalent phosphorus and divalent sulfur.
    Type: Grant
    Filed: February 12, 1987
    Date of Patent: June 2, 1992
    Assignee: Givaudan Corporation
    Inventors: Alan J. Chalk, Laszlo V. Wertheimer