Catalytic Hydrogenation Patents (Class 554/141)
  • Patent number: 9650582
    Abstract: An object of the present invention is to provide a method for hydrogenating a biodiesel fuel for producing a biodiesel fuel having an excellent oxidation stability and cold flow property. The present invention serves to produce a biodiesel fuel excellent in oxidation stability, by hydrogenating a biodiesel fuel with oxygen present in the reaction system in the presence of a catalyst containing at least one type of noble metal selected from metals of Groups 8 to 10 in the periodic table.
    Type: Grant
    Filed: March 3, 2015
    Date of Patent: May 16, 2017
    Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY
    Inventors: Takehisa Mochizuki, Makoto Toba, Yuuji Yoshimura, Yohko Abe, Shih-Yuan Chen
  • Patent number: 9598327
    Abstract: The invention relates to a process for the manufacture of diesel range hydrocarbons wherein a feed is hydrotreated in a hydrotreating step and isomerized in an isomerization step, and a feed comprising fresh feed containing more than 5 wt % of free fatty acids and at least one diluting agent is hydrotreated at a reaction temperature of 200-400° C., in a hydrotreating reactor in the presence of catalyst, and the ratio of the diluting agent/fresh feed is 5-30:1.
    Type: Grant
    Filed: September 4, 2014
    Date of Patent: March 21, 2017
    Assignee: NESTE OIL OYJ
    Inventors: Jukka Myllyoja, Pekka Aalto, Pekka Savolainen, Veli-Matti Purola, Ville Alopaeus, Johan Gronqvist
  • Patent number: 9404064
    Abstract: Biological compositions containing animal fats and plant oils desirably are free of contaminants prior to processing into a biofuel. Disclosed herein is a method of removing such contaminants from these compositions to make that processing more efficient. The method employs a unique arrangement of mixers and centrifuges along with acidic solutions and recycle streams to re-move these contaminants from the compositions.
    Type: Grant
    Filed: March 4, 2014
    Date of Patent: August 2, 2016
    Assignee: REG SYNTHETIC FUELS, LLC
    Inventors: Peter Guay, Dale Graham, Ramin Abhari, Peter Zdenek Havlik, Edward Gary Roth, H. Lynn Tomlinson
  • Patent number: 9238216
    Abstract: Provided is a palladium on carbon (Pd/C) catalyst obtained by using an ionic liquid, a method for preparing the same, and a method for hydrogenation of hydrofluorocarbon using the same. More particularly, palladium particles are supported on carbon particles by using an ionic liquid, and the resultant Pd/C catalyst is used for hydrogenation of hydrofluorocarbon. The catalyst includes palladium particles having a smaller particle size and a more uniform shape as compared to the existing Pd/C catalysts, and thus shows high catalytic activity.
    Type: Grant
    Filed: October 21, 2013
    Date of Patent: January 19, 2016
    Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY
    Inventors: Chang Soo Kim, Kyesang Yoo, Byoung Sung Ahn, Hyun Joo Lee, Jeong Myeong Ha, Hong Gon Kim
  • Patent number: 8927746
    Abstract: The subject matter of the invention is a process for synthesizing ?-functionalized acids of formula R—(CH2)n—COOH in which R is COOH or NH2CH2, from a feedstock of natural origin containing hydroxylated fatty acids.
    Type: Grant
    Filed: July 10, 2012
    Date of Patent: January 6, 2015
    Assignee: Arkema France
    Inventor: Jean-Luc Dubois
  • 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: 20140309445
    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: Application
    Filed: February 18, 2014
    Publication date: October 16, 2014
    Applicant: ELEVANCE RENEWABLE SCIENCES, INC.
    Inventors: Kevin D. Uptain, Charles Tanger, Hiroki Kaido
  • Publication number: 20140256972
    Abstract: The invention relates to a catalyst comprising nickel and a solid silica support, to a process for preparing such a catalyst and to a process for the hydrogenation of an unsaturated fatty material. According to the invention there is provided a catalyst comprising nickel on a solid silica support, wherein said catalyst has a specific pore volume of at least 0.4 ml/g and a TPR peak maximum within the range of 360-420° C.
    Type: Application
    Filed: October 12, 2012
    Publication date: September 11, 2014
    Applicant: BASF CORPORATION
    Inventors: Hermanus Johannes Bouwman, Robert Johan Andreas Maria Teroerde, Tjalling Rekker
  • Patent number: 8735616
    Abstract: Steps in the processing of oils derived from plants or vegetables include the degumming, deodorizing and bleaching of the oil before it can be used for further applications. By eliminating one or more of these steps from the processing of the oil, followed by hydrogenating the oil to a specified degree of hydrogenation, the resulting upgraded oils can be incorporated into products having commercial applications. The process uses a high shear mixing device and a hydrogenation catalyst. The process can utilize a single or multiple high shear devices, and utilize renewable oils instead of increasingly scarce petroleum based products. The resulting hydrogenated products may then be utilized in a variety of other commercial applications, such as to render cellulosic products water resistant, provide a coating for numerous cellulosic products, adhesive compositions, ink compositions, firelog compositions, drilling muds or asphalt modifiers.
    Type: Grant
    Filed: May 20, 2011
    Date of Patent: May 27, 2014
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Aziz Hassan, Gregory Borsinger
  • 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: 8648005
    Abstract: The present invention provides a method of preparing the copper-containing hydrogenation catalyst having high activity by liquid phase reduction without decreasing purity of the solvent and a method for efficiently producing an alcohol. The present invention provides the method of preparing the copper-containing hydrogenation catalyst, including reducing a molded precursor of the copper-containing hydrogenation catalyst by supplying hydrogen gas or a mixture of hydrogen gas with an inert gas at a temperature of 50 to 150° C. in the presence of a solvent to obtain the copper-containing hydrogenation catalyst, wherein the reduction is conducted at an average reduction velocity of the copper-containing hydrogenation catalyst of not more than 3.0% by weight/hour.
    Type: Grant
    Filed: September 10, 2009
    Date of Patent: February 11, 2014
    Assignee: Kao Corporation
    Inventors: Toru Sakamoto, Shoji Hasegawa
  • Patent number: 8603938
    Abstract: The present invention provides the method for preparing a catalyst including the following steps 1 and 2, and the method for producing an alcohol including preparing a catalyst by the method and subjecting a carboxylic acid or a carboxylic acid ester to catalytic reduction with hydrogen in the presence of the prepared catalyst: step 1: immersing a molded precursor of a catalyst containing metal oxide in a solvent, step 2: supplying hydrogen gas or a mixture of hydrogen gas with an inert gas to a catalyst layer in the presence of a solvent to reduce the catalyst precursor prepared in the step 1.
    Type: Grant
    Filed: September 10, 2009
    Date of Patent: December 10, 2013
    Assignee: Kao Corporation
    Inventors: Toru Sakamoto, Taku Mimura
  • Patent number: 8491856
    Abstract: A system for stripping fatty acids from triglycerides, the system including a reactor; a heating apparatus whereby a contents of the reactor may be heated to a temperature in the range of from 200° C. to 600° C.; and a vacuum pump capable of pulling a vacuum in the range of from 1 kPa to 50 kPa on the reactor.
    Type: Grant
    Filed: April 13, 2012
    Date of Patent: July 23, 2013
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Publication number: 20130150600
    Abstract: A hydrocarbon conversion process comprises contacting a renewable feedstock under hydroprocessing conditions with a bulk catalyst to form oleochemicals such as fatty alcohols, esters, and normal paraffins. Advantageously, the reaction conditions can be selected to directly convert the renewable feedstock to the desired product(s).
    Type: Application
    Filed: December 9, 2011
    Publication date: June 13, 2013
    Applicant: Chevron U.S.A. Inc.
    Inventors: Cong-Yan Chen, Alexander E. Kuperman, William J. Cannella
  • Patent number: 8399694
    Abstract: An object of the present invention is to provide a more simplified and more efficient process for producing a highly purified orange roughy oil having high storage stability. The present invention provides a process for producing a highly purified orange roughy oil substantially free of a polyunsaturated fatty acid ester having 4 to 6 double bonds, and having a saponification value of 98 to 113 and an iodine value of 73 to 89, comprising washing with an alkaline aqueous solution to remove a free fatty acid; hydrogenating with a catalyst to reduce a polyunsaturated fatty acid ester; and purifying by treatment with an adsorbent.
    Type: Grant
    Filed: October 10, 2008
    Date of Patent: March 19, 2013
    Assignee: Nippon Suisan Kaisha, Ltd.
    Inventors: Kazuhiko Hata, Akito Yamabe, Tsuyoshi Koriyama
  • Publication number: 20130055625
    Abstract: Provided is a method for producing biodiesel fuel having an excellent oxidative stability and fluidity at low temperature, wherein the method provides selective hydrogenation of a poly-unsaturated fatty acid alkyl ester to the mono-unsaturated fatty acid alkyl ester while inhibiting the formation of the trans-isomer, and a biodiesel fuel composition. In the method for producing biodiesel fuel, a fatty acid alkyl ester prepared from fat and/or waste edible oil by transesterification reaction, and/or (2) a fatty acid alkyl ester treated by esterification reaction of a fatty acid is hydrogenated in the presence of a hydrogenation catalyst containing at least one of noble metals selected from those of Groups 8-10 in the periodic table under low hydrogen pressure.
    Type: Application
    Filed: February 18, 2011
    Publication date: March 7, 2013
    Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY
    Inventors: Makoto Toba, Yuji Yoshimura, Yoko Abe
  • Patent number: 8334396
    Abstract: Disclosed is a process for the manufacture of saturated fatty acid esters by subjecting unsaturated fatty acid esters to hydrogenation in the presence of a catalyst suitable for catalysing the saturation of double bonds in the esters, which is characterized in that said catalyst represents a homogenous complex of a Group VIII metal and a sulfonated phosphite as the polar ionic ligand.
    Type: Grant
    Filed: June 14, 2008
    Date of Patent: December 18, 2012
    Assignee: Cognis IP Management GmbH
    Inventors: Georgios Papadogianakis, Achilleas Bouriazos, Angeliki Tsichla, Christiana Vasiliou
  • 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: 8242318
    Abstract: Catalytic hydrogenation of a double bond, notably a C?C or C?N double bond, is carried out using a homogenous catalyst which is a complex of rhodium or other transition metal containing at least one ligand which is a nitrogenous organic base. Preferably the complex is phosphorus-free and the ligand is a bicyclic base having formula where R1 and R4 are hydrocarbon chains. R1 preferably is a saturated chain of two carbon atoms and R4 preferably is a saturated chain of three to five carbon atoms.
    Type: Grant
    Filed: December 3, 2009
    Date of Patent: August 14, 2012
    Assignee: Schlumberger Technology Corporation
    Inventors: Li Jiang, Timothy Jones, Fenglou Zou
  • Publication number: 20120178951
    Abstract: The invention relates to an apparatus for continuously carrying out heterogeneously catalyzed chemical reactions, comprising a microwave-transparent tube, the longitudinal axis of which extends in the direction of propagation of the microwaves of a single-mode microwave applicator and which is filled with an open-cell foam that carries or is made of catalytically active species.
    Type: Application
    Filed: September 3, 2010
    Publication date: July 12, 2012
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Matthias Krull, Roman Morschhaeuser, Hans-Juergen Scholz
  • 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
  • Patent number: 8182556
    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: October 7, 2011
    Date of Patent: May 22, 2012
    Assignee: Haliae Development, LLC
    Inventor: Aniket Kale
  • Patent number: 8178705
    Abstract: A method of producing volatilized fatty acids by heating a feedstock comprising at least one fat or oil in a reactor under inert vacuum to volatilize fatty acids, and removing volatilized fatty acids from bottoms residue comprising cross-linked oil. A system for stripping fatty acids from triglycerides, the system comprising a reactor, heating apparatus and a vacuum pump capable of pulling a vacuum in the range of from 1 kPa to 50 kPa on the reactor. A system for producing a hydrogenated product including a reactor comprising an inlet for a stream comprising triglycerides, an outlet for volatilized fatty acids, and an outlet for a cross-linked product, heating apparatus, a vacuum pump capable of pulling a vacuum in the range of from 1 kPa to 50 kPa on the reactor, and a hydrogenation reactor, wherein an inlet of the hydrogenation reactor is fluidly connected to the outlet for cross-linked product.
    Type: Grant
    Filed: May 10, 2011
    Date of Patent: May 15, 2012
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • 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
  • Publication number: 20110301024
    Abstract: A process for preparing a catalyst precursor includes, in a first preparation step, impregnating a particulate catalyst support with an organic metal compound in a carrier liquid. The metal of the organic metal compound is an active catalyst component. An impregnated intermediate is formed, and is calcined to obtain a calcined intermediate. Thereafter, in a second preparation step, the calcined intermediate from the first preparation step is impregnated with an inorganic metal salt in a carrier liquid. The metal of the inorganic metal salt is an active catalyst component. An impregnated support is obtained, and is calcined, to obtain the catalyst precursor. The metal is in particular cobalt. The precursor is reduced, in particular with hydrogen, to obtain the active catalyst. Also claimed is a process for the hydrogenation of CO, as well as a process for the hydrogenation of an organic compound using the so-prepared catalyst.
    Type: Application
    Filed: February 23, 2010
    Publication date: December 8, 2011
    Applicant: SASOL TECHNOLOGY (PROPRIETARY) LIMITED
    Inventors: Robert Johan Andreas Maria Terorde, Luuk Laurentius Kramer
  • Publication number: 20110287159
    Abstract: Steps in the processing of oils derived from plants or vegetables include the degumming, deodorizing and bleaching of the oil before it can be used for further applications. By eliminating one or more of these steps from the processing of the oil, followed by hydrogenating the oil to a specified degree of hydrogenation, the resulting upgraded oils can be incorporated into products having commercial applications. The process uses a high shear mixing device and a hydrogenation catalyst. The process can utilize a single or multiple high shear devices, and utilize renewable oils instead of increasingly scarce petroleum based products. The resulting hydrogenated products may then be utilized in a variety of other commercial applications, such as to render cellulosic products water resistant, provide a coating for numerous cellulosic products, adhesive compositions, ink compositions, firelog compositions, drilling muds or asphalt modifiers.
    Type: Application
    Filed: May 20, 2011
    Publication date: November 24, 2011
    Applicant: HRD Corp.
    Inventors: ABBAS HASSAN, AZIZ HASSAN, GREGORY BORSINGER
  • Patent number: 8026403
    Abstract: A method for producing a product comprising at least one selected from C2+ hydrocarbons, oxygenates, and combinations thereof from light gas comprising one or more of carbon dioxide, methane, ethane, propane, butane, pentane, and methanol by forming a dispersion of light gas in a liquid feed, wherein the dispersion is formed at least in part with high shear forces and wherein at least one of the liquid feed and the light gas is a hydrogen source. A system for carrying out the method is also presented.
    Type: Grant
    Filed: June 17, 2008
    Date of Patent: September 27, 2011
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Patent number: 7947323
    Abstract: The present invention relates to a process for the production of a fat composition for confectionery or baking applications. According to this process, a starting fat composition containing palm oil or a palm oil fraction and having the following composition: (1) a glyceride composition with—a S2U content between 47 and 75 wt. %, —a SU2+U3 content <40 wt. %, —a S3 content between 1 and 15 wt. %, —a diglyceride content of 3 to 12 wt. %, the glyceride contents being expressed as wt. % with respect to the total amount of di- and triglycerides in which S means a saturated fatty acid with A hydrocarbon chain length of 14-24 carbon atoms and U means unsaturated fatty acid with a hydrocarbon chain length of 14-24 carbon atoms and (2) a total content of unsaturated fatty acids of less than 55 wt. %, preferably less than 50 wt. %, more preferably less than 48 wt. %, is subjected to a catalytic hydrogenation so as to obtain a first fat with a trans fatty acid content <wt. %, preferably <10 wt.
    Type: Grant
    Filed: March 26, 2003
    Date of Patent: May 24, 2011
    Assignee: Fuji Oil Company, Limited
    Inventors: Bernard Cleenewerck, Karen Saey, Marij Van Dyck
  • Patent number: 7820841
    Abstract: The present disclosure provides low trans-fatty acid fat compositions, methods of hydrogenating unsaturated feed-stocks (e.g., oils), and hydrogenation catalyst compositions. One exemplary method involves producing a catalyst composition by heating a nickel-based catalyst to a first temperature of at least about 85° C. in the presence of hydrogen and a fat component. An unsaturated feedstock may be contacted with the catalyst composition and hydrogenated by sustaining a hydrogenation reaction at a second temperature of no greater than about 70° C. Some specific implementations of the invention permit the production of partially hydrogenated seed oils with low trans-fatty acid contents.
    Type: Grant
    Filed: July 30, 2004
    Date of Patent: October 26, 2010
    Assignee: Cargill, Incorporated
    Inventors: N. Hans Van Toor, Gijsbertus Johannes Van Rossum, Marco B. Kruidenberg
  • Publication number: 20100234625
    Abstract: Disclosed is a process for the manufacture of saturated fatty acid esters by subjecting unsaturated fatty acid esters to hydrogenation in the presence of a catalyst suitable for catalysing the saturation of double bonds in the esters, which is characterised in that said catalyst represents a homogenous complex of a Group VIII metal and a sulfonated phosphite as the polar ionic ligand.
    Type: Application
    Filed: June 14, 2008
    Publication date: September 16, 2010
    Applicants: COGNIS IP MANAGEMENT GMBH, NATIONAL & KAPODISTRIAN UNIVERSITY OF ATHENS
    Inventors: Georgios Papadogianakis, Achilleas Bouriazos, Angeliki Tsichla, Christiana Vasiliou
  • Publication number: 20100168454
    Abstract: Catalytic hydrogenation of a double bond, notably a C?C or C?N double bond, is carried out using a homogenous catalyst which is a complex of rhodium or other transition metal containing at least one ligand which is a nitrogenous organic base. Preferably the complex is phosphorus-free and the ligand is a bicyclic base having formula where R1 and R4 are hydrocarbon chains. R1 preferably is a saturated chain of two carbon atoms and R4 preferably is a saturated chain of three to five carbon atoms.
    Type: Application
    Filed: December 3, 2009
    Publication date: July 1, 2010
    Applicant: Schlumberger Technology Corporation
    Inventors: Li Jiang, Timothy Jones, Fenglou Zou
  • Patent number: 7741501
    Abstract: A process for carrying out heterogeneously catalyzed hydrogenation reactions in a fixed-bed reactor includes providing at least one main reactor containing a first amount of catalyst; providing a first auxiliary reactor and a second auxiliary reactor, each containing a second amount of catalyst, wherein the first amount of catalyst is relatively larger than the second amount of catalyst; passing a starting product of a fatty compound through the first auxiliary reactor and reacting the starting product with hydrogen in the presence of the catalyst; continuing the reaction through the at least one main reactor; and continuing the reaction through the second auxiliary reactor, wherein the first auxiliary reactor is reactivated. Another process provided includes a first and second main reactor, and a first and second auxiliary reactor, where relatively pure and impure starting products of a fatty compound are processed substantially continuously by cyclic switching of the reactors.
    Type: Grant
    Filed: February 1, 2007
    Date of Patent: June 22, 2010
    Assignee: Cognis IP Management GmbH
    Inventors: Stephan Wuerkert, Bernhard Gutsche
  • Patent number: 7718211
    Abstract: Shortening systems are prepared which include hydrogenated edible oils that are hydrogenated in a manner to minimize the formation of trans-stereoisomers. A conditioned catalyst is used which disfavors trans-stereoisomer formation without significantly negatively impacting the length of time required to form solids for a useful shortening base stock through hydrogenation. Preferred conditioning agents are organic acid phosphates and phosphoric acid, In a preferred embodiment, a confectionary shortening is provided which incorporates a polyglycerol ester emulsifier.
    Type: Grant
    Filed: December 27, 2006
    Date of Patent: May 18, 2010
    Assignee: Bunge Oils, Inc.
    Inventor: Neil W. Higgins
  • Publication number: 20100094033
    Abstract: A method for producing starting materials or additives for cosmetics, pharmaceuticals and/or hydrocarbon-based fuels, especially for heating systems or internal combustion engines, takes organic residues or waste materials and decontaminates or sterilizes them with a hydrogenation process. In particular, the materials classified as K1, K2 or K3 according to EU Directive 1774/2002 are used for generating or producing the cited starting materials or additives, whereby an adequate decontamination of the residues or waste materials that are classified as being hazardous to health is ensured.
    Type: Application
    Filed: October 24, 2007
    Publication date: April 15, 2010
    Inventor: Dieter Tischendorf
  • Publication number: 20100055516
    Abstract: A method of providing a porous surface on a nickel substrate comprising treating the substrate with a flowing stream of gas comprising ammonia or hydrazine at a temperature of at least 4000 C, the resultant porous surface comprising pores which are substantially all interconnected and have access to the surface.
    Type: Application
    Filed: October 25, 2007
    Publication date: March 4, 2010
    Inventors: Geoffrey Mason, Bryan Buffham, Klaus Hellgardt, Paul Russell, David Richardson
  • Patent number: 7667058
    Abstract: Disclosed are heterogeneous processes (i) for the hydrogenation of a compound containing at least one unsaturated carbon-carbon bond, and (ii) for the hydro-dehalogenation of a compound containing at least one C—Cl, C—Br or C—I bond. The processes comprise reacting said compound with a hydrogenating agent and a heterogeneous hydrogenation catalyst in the presence of an ionic liquid.
    Type: Grant
    Filed: May 17, 2002
    Date of Patent: February 23, 2010
    Assignee: The Queen's University of Belfast
    Inventors: Kris Anderson, Peter Goodrich, Christopher Hardacre, Sarah Elizabeth Jane McMath
  • Publication number: 20100022664
    Abstract: Suggested is a process for the manufacture of unsaturated fatty acid alkyl esters or glycerides having a total content of C 18:1 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—which is characterised in that the hydrogenation is conducted in an aqueous/organic two phase system in the presence of a water soluble catalyst consisting of a Group VIII metal and a hydrophilic ligand.
    Type: Application
    Filed: October 2, 2007
    Publication date: January 28, 2010
    Applicant: COGNIS IP MANAGEMENT GMBH
    Inventors: Georgios Papadogianakis, Achilleas Bouriazos, Konstandinos Mouratidis, Nikolas Psaroudakis
  • Patent number: 7585990
    Abstract: The present disclosure provides low trans-fatty acid fat compositions, methods of hydrogenating unsaturated feedstocks (e.g., oils), and hydrogenation catalyst compositions. One exemplary method involves producing an activated catalyst composition by heating a nickel-based catalyst to a first temperature of at least about 100° C. in the presence of hydrogen and a fat component. An unsaturated feedstock may be contacted with the activated catalyst composition and hydrogenated by sustaining a hydrogenation reaction at a second temperature of no greater than about 70° C. Some specific implementations of the invention permit the production of partially hydrogenated seed oils with low trans-fatty acid contents.
    Type: Grant
    Filed: December 31, 2003
    Date of Patent: September 8, 2009
    Assignee: Cargill, Incorporated
    Inventors: Hans van Toor, Gijsbertus Johannes van Rossum, Marco Kruidenberg
  • Publication number: 20090142470
    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: Application
    Filed: May 9, 2005
    Publication date: June 4, 2009
    Applicant: BASF CATALYSTS LLC
    Inventors: Annemarie Elisa Wilhelmina Beers, Pieter Hildegardus Berben
  • Patent number: 7538237
    Abstract: A process for performing a chemical reaction between a plurality of chemical reactants in the presence of a catalyst, with at least a first reactant in a liquid phase and at least a second reactant in a gas phase, the first and second reactants mixing at least by interdiffusion. The process comprises supplying the reactants to a passage defined by a first surface and a second surface and optionally moving at least one of the first surface and second surface relative to each other. The reactants their mixture or reaction products form respective boundary layers against the first and second surfaces and the radial spacing between the first surface and second surface is equal to or less than the back-to-back radial thicknesses of the boundary layers.
    Type: Grant
    Filed: May 28, 2004
    Date of Patent: May 26, 2009
    Assignee: Kreido Laboratories
    Inventors: Richard A. Holl, Eric A. Gulliver, John L. Cihonski
  • Patent number: 7498453
    Abstract: This disclosure describes select low trans-fatty acid fats and fat compositions and methods of making such fats and fat compositions. These fats and fat compositions achieve properties commonly associated with typical partially hydrogenated fats, but avoid the high trans-fatty acid contents typically associated with such fats.
    Type: Grant
    Filed: August 2, 2004
    Date of Patent: March 3, 2009
    Assignee: Cargill Incorporated
    Inventors: N. Hans Van Toor, Gijsbertus Johannes Van Rossum, Marco B. Kruidenberg
  • Publication number: 20080214852
    Abstract: Copper compositions that are useful as hydrogenation catalysts are disclosed. In particular, the copper compounds are catalysts for the selective hydrogenation of oils that contain unsaturated fatty acyl components such as unsaturated vegetable oils. Methods of preparing the copper compositions are also disclosed. Methods of hydrogenating unsaturated compositions that contain at least two sites of unsaturation using the hydrogenation catalysts, along with products obtained from the hydrogenation reactions described herein are also disclosed.
    Type: Application
    Filed: October 31, 2007
    Publication date: September 4, 2008
    Applicant: Archer-Daniels-Midland Company
    Inventor: Ronald T. Sleeter
  • Patent number: 7169430
    Abstract: Shortening systems are prepared which include hydrogenated edible oils that are hydrogenated in a manner to minimize the formation of trans-stereoisomers. A conditioned catalyst is used which disfavors trans-stereoisomer formation without significantly negatively impacting the length of time required to form solids for a useful shortening base stock through hydrogenation. Preferred conditioning agents are organic acid phosphates and phosphoric acid. In a preferred embodiment, a confectionary shortening is provided which incorporates a polyglycerol ester emulsifier.
    Type: Grant
    Filed: January 28, 2003
    Date of Patent: January 30, 2007
    Assignee: Bunge Oils, Inc.
    Inventor: Neil W. Higgins
  • Patent number: 7157590
    Abstract: The present invention provides a new and effective process for the synthesis of 17-phenyl-18,19,20-trinor-PGF2? and its derivatives, including the anti-glaucoma drugs Bimatoprost and Latanoprost. The benefit of the present invention rises inter alia from the fact that a major intermediate involved in the synthesis of the above compounds may be isolated from a mixture containing also an undesired isomer, by crystallization. In addition, the undesired isomer may be oxidized to give the starting compound, which is then recycled.
    Type: Grant
    Filed: May 3, 2002
    Date of Patent: January 2, 2007
    Assignee: Finetech Laboratories Ltd.
    Inventors: Arie Gutman, Gennady Nisnevich, Marina Etinger, Igor Zaltzman, Lev Yudovitch, Boris Pertsikov
  • 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: 6927300
    Abstract: Disclosed is a process for the preparation of the anti-glaucoma drug Latanoprost, in good yield, in large amounts and with desired purity. Also disclosed are novel intermediates for the above process.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: August 9, 2005
    Assignee: FineTech Laboratories LTD
    Inventors: Arie Gutman, Gennadiy Nisnevich, Marina Etinger, Igor Zaltzman, Lev Judovich, Boris Pertsikov
  • Patent number: 6916943
    Abstract: A process of making a supported catalyst includes steps of preparing a washcoat containing a mixture of hydrolyzed silicon alkoxide and a filler, depositing the washcoat on a surface of a solid support, drying the washcoat deposited on the surface of the solid support to form a coating on the surface of the solid support, and distributing a metal catalyst on the coating. The resulting supported catalyst may be used in a reaction vessel, such as a fixed bed reactor, for effecting a catalytic reaction, such as catalytic hydrogenation of an edible oil. The washcoatings can be formulated to provide a viscous composition that can be applied to form a thick coating on a substrate. The dried washcoatings exhibit excellent stability, cohesive layering strength, and adhesive strength between the coating and a substrate.
    Type: Grant
    Filed: December 16, 2002
    Date of Patent: July 12, 2005
    Assignee: Corning Incorporated
    Inventors: William P. Addiego, Christopher R. Glose
  • Patent number: 6846772
    Abstract: Production of nickel/silica hydrogenation catalyst precursors by heating a slurry of particulate silica, e.g. kieselguhr, in an aqueous nickel ammine carbonate solution for a total period of at least 200 minutes at a pH above 7.5, followed by filtration, washing, drying, and optionally calcination.
    Type: Grant
    Filed: January 21, 2003
    Date of Patent: January 25, 2005
    Assignee: Johnson Matthey Public Limited Company
    Inventors: Cornelis Martinus Lok, Gavin Gray, Stephen Derek Rogers, Stephen Bailey
  • Publication number: 20040267034
    Abstract: Disclosed are heterogeneous processes (i) for the hydrogenation of a compound containing at least one unsaturated carbon-carbon bond, and (ii) for the hydro-dehalogenation of a compound containing at least one C—Cl, C—Br or C—I bond. The processes comprise reacting said compound with a hydrogenating agent and a heterogeneous hydrogenation catalyst in the presence of an ionic liquid.
    Type: Application
    Filed: July 30, 2004
    Publication date: December 30, 2004
    Inventors: Kris Anderson, Peter Goodrich, Christopher Hardacre, Sarah Elizabeth Jane McMath