Plural Hydrogenation Steps Or Continuous Hydrogenation Process Patents (Class 554/144)
  • Patent number: 10683465
    Abstract: The invention relates to a process for the hydrogenation of vegetable oils that selectively converts polyunsaturated fatty acids into mono-unsaturated fatty acids, and to the products obtained therefrom. Vegetable oils obtained by the process according to the invention have a particularly high content of monounsaturated fatty acids and are suitable for use as raw materials for the synthesis of chemical intermediates.
    Type: Grant
    Filed: June 20, 2017
    Date of Patent: June 16, 2020
    Assignee: NOVAMONT S.P.A.
    Inventors: Giampietro Borsotti, Francesca Digioia
  • Patent number: 10654785
    Abstract: Conversion of vegetable-derived triglycerides to fatty acid methyl esters (FAMEs) is a popular approach to the generation of biodiesel fuels and the basis of a growing industry. Drawbacks of the strategy are that (a) the glycerol backbone of the triglyceride is discarded as waste in this synthesis, and (2) many natural triglycerides are multiply-unsaturated or fully saturated, giving inferior performance and causing engine problems with long-term use. Here, we show that catalysis by iridium complex 1 can address both of these problems through selective reduction of triglycerides high in polyunsaturated fatty esters to FAMEs with high oleate concentration. This is realized using hydrogen imbedded in the triglyceride backbone, concurrently generating lactate as a value-added C3 product. Additional methanol or glycerol as a hydrogen source enables reduction of corn and soybean oils to >80% oleate.
    Type: Grant
    Filed: November 16, 2018
    Date of Patent: May 19, 2020
    Assignee: University of Southern California
    Inventors: Travis J. Williams, Zhiyao Lu, Valery Cherepakhin
  • Patent number: 9650327
    Abstract: This invention relates to a process for the selective hydrogenation of vegetable oils. In particular the invention relates to a process for the hydrogenation of vegetable oils which is capable of selectively converting polyunsaturated fatty acids into mono-unsaturated fatty acids and products obtained therefrom. The vegetable oils obtained from the process according to the invention have in particular a high mono-unsaturated fatty acids content and are particularly suitable for use as raw materials for the synthesis of chemical intermediates.
    Type: Grant
    Filed: June 25, 2014
    Date of Patent: May 16, 2017
    Assignee: NOVAMONT S.P.A.
    Inventors: Giampietro Borsotti, Luigi Capuzzi, Francesca Digioia
  • Patent number: 9592484
    Abstract: Herein disclosed is a system for producing an organic, the system including at least one high shear mixing device having at least one rotor and at least one stator separated by a shear gap, wherein the shear gap is the minimum distance between the at least one rotor and the at least one stator; a pump configured for delivering a fluid stream comprising liquid medium and light gas to the at least one high shear mixing device, wherein the at least one high shear mixing device is configured to form a dispersion of the light gas in the liquid medium; and a reactor comprising at least one inlet and at least one outlet, wherein the at least one inlet of the reactor is fluidly connected to the at least one high shear mixing device, and wherein the at least one outlet is configured for extracting the organic therefrom.
    Type: Grant
    Filed: January 29, 2013
    Date of Patent: March 14, 2017
    Assignee: HRD Corporation
    Inventors: Abbas Hassan, Aziz Hassan, Rayford G. Anthony, Gregory G. Borsinger
  • Patent number: 9403105
    Abstract: A process and device to reduce the pressure of fluid containing liquid and possibly a gaseous phase or solid particles without reducing the cross sectional area or using moving parts. The pressure reduction is obtained by passing the fluid to be depressurized, in sequence, through a plurality of pairs of steps. In the first step of each pair, part of the pressure energy of the fluid is converted to gravitational potential; in the second step the gravitational potential is converted into thermal energy, so as to prevent the reconversion of the same into pressure energy.
    Type: Grant
    Filed: December 28, 2011
    Date of Patent: August 2, 2016
    Assignee: Versalis S.P.A.
    Inventors: Riccardo Felisari, Alessandro Casalini
  • 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
  • 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: 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
  • Publication number: 20110098494
    Abstract: The invention describes a method of treating feeds from renewable sources comprising a hydrotreatment stage comprising at least two catalytic zones in which the entry stream comprising said feed mixed with at least a part of a hydrotreated liquid effluent from stage b) is introduced into the first catalytic zone at a temperature comprised between 150 and 260° C., and the effluent from the first catalytic zone is then introduced, mixed with at least a part of a hydrotreated liquid effluent from stage b) and preheated, into the following catalytic zone or zones at a temperature comprised between 260 and 320° C.
    Type: Application
    Filed: October 26, 2010
    Publication date: April 28, 2011
    Applicant: IFP ENERGIES NOUVELLES
    Inventors: Wilfried WEISS, Laurent Bournay, Thierry Chapus, Antoine Daudin
  • 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: 6716155
    Abstract: A process for the hydrogenation of a polyunsaturated oil, wherein said oil is reacted with hydrogen in the presence of a copper-chromium containing catalyst at a temperature of from about 200 to 300° C. and a pressure of from about 300 to 500 psig, for 3-8 hours. The reaction results in a product having a monounsaturated fatty acid percent conversion (i.e., monounsaturated fatty acid content) of from about 60-90%, preferably from about 70-90% and most preferably, from about 80-90%. The copper-chromium catalyst may also be recovered and reused without regeneration or further treatment prior to reuse.
    Type: Grant
    Filed: December 18, 2002
    Date of Patent: April 6, 2004
    Assignee: Archer-Daniels-Midland Company
    Inventor: Ronald Sleeter
  • 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: 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: 5734070
    Abstract: A process is disclosed for continuously hydrogenating unsaturated fats, fatty acids or fatty acid esters on a shaped catalyst in a solid bed. The reactants flow over the catalyst in the presence of a medium or solvent mixture in supercritical conditions. This leads to considerably improved activity and selectivity of the hydrogenation reaction compared with conventional trickle bed hydrogenation processes.
    Type: Grant
    Filed: August 14, 1996
    Date of Patent: March 31, 1998
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Tacke, Stefan Wieland, Peter Panster, Martin Bankmann, Reinhold Brand, Hendrik Magerlein
  • 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: 5360920
    Abstract: Fatty materials are hydrogenated in a plate heat exchanger at a pressure above about 150 psig. The use of high pressure and high shear as provided by the appropriate surface to volume ratio and pressure drop in the heat exchanger, enables the fatty material to be efficiently hydrogenated, and for touch hardening the temperature can be reduced to minimize the formation of trans-isomers.
    Type: Grant
    Filed: August 7, 1992
    Date of Patent: November 1, 1994
    Assignee: The Procter & Gamble Company
    Inventors: Vicki L. Weber, Joseph S. Boggs, Richard M. King