Using Organic Extraneous Agent Patents (Class 585/645)
  • Patent number: 11203679
    Abstract: The present invention relates to the use of Ru and Os carbene complexes with a hydroxamic acid (ester) function for the metathesis degradation of nitrile rubber (NBR). The invention further relates to a method for producing hydrogenated nitrile rubbers, by subjecting a nitrile rubber to a metathesis degradation in the presence of the said catalyst, and the degraded nitrile rubber obtained subsequently undergoes a hydrogenation, preferably in situ.
    Type: Grant
    Filed: April 26, 2019
    Date of Patent: December 21, 2021
    Assignee: ARLANXEO DEUTSCHLAND GMBH
    Inventors: Silvia Schnitzler, Sarah David
  • Patent number: 11059940
    Abstract: A method of carrying out a metathesis reaction includes the combination of at least one alkene or non conjugated diene with a Ruthenium-based catalyst with an cyclic(alkyl)(amino)carbene ligand to form a reaction mixture and heating the reaction mixture to a temperature of 100° C. or greater. The reaction can be an ADMET, ROMP, a metathesis ring-closure or an olefin exchange reaction.
    Type: Grant
    Filed: May 13, 2020
    Date of Patent: July 13, 2021
    Assignee: University of Florida Research Foundation, Incorporated
    Inventors: Kenneth B. Wagener, Michael H. Bell
  • Patent number: 9816051
    Abstract: A self-metathesis process for the production of unsaturated dicarboxylic fatty diacids and/or unsaturated dicarboxylic fatty diesters, wherein unsaturated carboxylic fatty acids and/or esters of unsaturated carboxylic fatty acids are reacted in the presence of at least one defined ruthenium based catalyst compound. A catalyst enhancer compound selected from a sacrificial catalyst or a non-catalyst enhancer may also be used. The process exhibits improved reaction times and/or the catalyst can be used at very low concentrations.
    Type: Grant
    Filed: March 18, 2013
    Date of Patent: November 14, 2017
    Assignee: Croda International PLC
    Inventors: Bastiaan Wels, Hans Ridderikhoff, Tanja Van Bergen-Brenkman, Dessy Liminto
  • Patent number: 9809513
    Abstract: Processes for the production of olefins are disclosed, which may include: contacting a hydrocarbon mixture comprising linear butenes with an isomerization catalyst to form an isomerization product comprising 2-butenes and 1-butenes; contacting the isomerization product with a first metathesis catalyst to form a first metathesis product comprising 2-pentene and propylene, as well as any unreacted C4 olefins, and byproducts ethylene and 3-hexene; and fractionating the first metathesis product to form a C3? fraction and a C5 fraction comprising 2-pentene. The 2-pentene may then be advantageously used to produce high purity 1-butene, 3-hexene, 1-hexene, propylene, or other desired products.
    Type: Grant
    Filed: November 20, 2014
    Date of Patent: November 7, 2017
    Assignee: Lummus Technology Inc.
    Inventors: Sukwon Choi, Bala Ramachandran
  • Patent number: 9556296
    Abstract: This invention describes a process for metathesis of olefins from feedstocks obtained from the Fischer-Tropsch process, using as catalyst a ruthenium alkylidene complex comprising a saturated or unsaturated, dissymmetrical N-heterocyclic carbene (NHC) ligand.
    Type: Grant
    Filed: April 25, 2014
    Date of Patent: January 31, 2017
    Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, IFP ENERGIES NOUVELLES, ECOLE NATIONALE SUPERIEURE DE CHIMIE DE RENNES
    Inventors: Helene Olivier-Bourbigou, Francois Hugues, Severine Forget, Mathieu Rouen, Marc Mauduit
  • Patent number: 8993470
    Abstract: Organometallic compounds of the general formula (I), in which M=Mo, W, are claimed.
    Type: Grant
    Filed: March 31, 2011
    Date of Patent: March 31, 2015
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Alois Fuerstner, Johannes Heppekausen, Volker Hickmann, Robert Stade
  • Patent number: 8993823
    Abstract: A process for the metathesis of olefins has been developed. The process comprises contacting a hydrocarbon feedstock with a catalyst at metathesis conditions. The catalyst comprises a tungsten compound, which contains at least one tungsten-fluoro bond, dispersed or grafted onto a support. A specific example of the catalyst is the compound WOF(CH2CMe3)3 grafted onto a silica support. The feedstock comprises a first and a second olefin wherein the second olefin has a carbon number of at least two greater than the first olefin and the product is an olefin with a carbon number intermediate between the first and second olefin. Specifically the process produces propylene from ethylene and butylene.
    Type: Grant
    Filed: June 25, 2014
    Date of Patent: March 31, 2015
    Assignee: UOP LLC
    Inventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
  • Patent number: 8895794
    Abstract: We provide a process for producing high quality gasoline blending components, comprising: a) operating an alkylation reactor in an alkylate mode wherein a gasoline blending component is made having a RON of 90 or higher; and b) operating the alkylation reactor in a distillate mode wherein a second gasoline blending component and a distillate product is made, and wherein the second gasoline blending component has a RON of 85 or higher. Also, we provide an alkylation process unit, comprising: a control system connected to an alkylation reactor, that enables the alkylation reactor to operate in both an alkylate mode that produces a gasoline blending component having a RON of 90 or higher and in a distillate mode that produces a second gasoline blending component having a RON of 85 or higher.
    Type: Grant
    Filed: March 17, 2010
    Date of Patent: November 25, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventors: Hye-Kyung Timken, Shawn Winter, Howard S. Lacheen, Sven Ivar Hommeltoft
  • Publication number: 20140309433
    Abstract: Described herein are compounds and methods of catalyzing ethenolysis reactions, optionally on an industrial scale. In certain embodiments, the catalysts bear cyclic alkyl amino carbene (CAAC) ligands with an ortho substituent, such as a methyl substituent, on an N-aryl ring. When used to catalyze ethenolysis reactions, certain such compounds produce a turnover number greater than 50,000.
    Type: Application
    Filed: April 10, 2014
    Publication date: October 16, 2014
    Inventors: Vanessa M. Marx, Mohand-Ameziane Melaimi, Scott C. Virgil, Benjamin K. Keitz, Robert H. Grubbs, Guy Bertrand
  • Publication number: 20140275595
    Abstract: A method for treating a substrate prior to a metathesis reaction includes treating the substrate with a first agent configured to mitigate potentially adverse effects of one or more contaminants in the substrate on a catalyst used to catalyze the metathesis reaction. The treating reduces a level of the one or more contaminants by an amount sufficient to enable the metathesis reaction to proceed at a substrate-to-catalyst molar ratio of at least about 7,500 to 1. Methods for metathesizing substrates are described.
    Type: Application
    Filed: March 13, 2014
    Publication date: September 18, 2014
    Applicant: ELEVANCE RENEWABLE SCIENCES, INC.
    Inventors: Keith M. Wampler, Steven A. Cohen, Georg E. Frater, Levente Ondi, Jeno Varga
  • Publication number: 20140235913
    Abstract: This invention describes a process for metathesis of olefins from feedstocks obtained from the Fischer-Tropsch process, using as catalyst a ruthenium indenylidene complex comprising a saturated or unsaturated, symmetric N-heterocyclic carbene.
    Type: Application
    Filed: February 21, 2014
    Publication date: August 21, 2014
    Applicant: IFP ENERGIES NOUVELLES
    Inventors: Helene OLIVIER-BOURBIGOU, Mikael BERTHOD
  • Publication number: 20140200382
    Abstract: This invention relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by a selected olefin metathesis catalyst. In one embodiment of the invention, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting an olefinic substrate comprised of at least one internal olefin with ethylene, in the presence of a metathesis catalyst, wherein the catalyst is present in an amount that is less than about 1000 ppm relative to the olefinic substrate, and wherein the metathesis catalyst has the structure of formula (II) wherein the various substituents are as defined herein. The invention has utility, for example, in the fields of catalysis, organic synthesis, and industrial chemistry.
    Type: Application
    Filed: August 13, 2013
    Publication date: July 17, 2014
    Applicant: MATERIA, INC.
    Inventor: Yann SCHRODI
  • Publication number: 20130331630
    Abstract: A method for suppressing dehydrogenation includes reacting an optionally functionalized olefin reactant in a metathesis reaction to form an olefin metathesis product; and providing a dehydrogenation suppression agent in admixture with (a) the olefin metathesis product and/or the optionally functionalized olefin reactant, and (b) a metal-containing material selected from the group consisting of residual metathesis catalyst, a hydrogen transfer agent, and a combination thereof, under conditions that are sufficient to passivate at least a portion of the metal-containing material. Methods of refining natural oils and methods of producing fuel compositions are also described.
    Type: Application
    Filed: June 6, 2013
    Publication date: December 12, 2013
    Inventors: Bradon J. Dreyer, Brian M. Pease
  • Publication number: 20130289327
    Abstract: This invention relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by a selected olefin metathesis catalyst. In one embodiment of the invention, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting an olefinic substrate comprised of at least one internal olefin with ethylene, in the presence of a metathesis catalyst, wherein the catalyst is present in an amount that is less than about 1000 ppm relative to the olefinic substrate, and wherein the metathesis catalyst has the structure of formula (II) wherein the various substituents are as defined herein. The invention has utility, for example, in the fields of catalysis, organic synthesis, and industrial chemistry.
    Type: Application
    Filed: June 10, 2013
    Publication date: October 31, 2013
    Inventor: Yann Schrodi
  • Patent number: 8519069
    Abstract: The present invention relates to a catalytic complex for olefin metathesis reactions, to a process for its preparation and to its use in olefin metathesis reactions, particularly in ring opening metathesis polymerisation (ROMP) reactions.
    Type: Grant
    Filed: July 7, 2010
    Date of Patent: August 27, 2013
    Assignee: RIMTEC Corporation
    Inventor: Renata Drozdzak
  • Publication number: 20130204026
    Abstract: Synthetic methods for the in-situ formation of olefin metathesis catalysts are disclosed, as well as the use of such catalysts in metathesis reactions of olefins and olefin compounds.
    Type: Application
    Filed: March 24, 2011
    Publication date: August 8, 2013
    Applicant: MATERIA, INC.
    Inventor: Yann Schrodi
  • Publication number: 20130197178
    Abstract: The present invention provides novel and stable crystalline 1H-1,2,3 triazolium carbenes and metal complexes of 1H-1,2,3 triazolium carbenes. The present invention also provides methods of making 1H-1,2,3 triazolium carbenes and metal complexes of 1H-1,2,3 triazolium carbenes. The present invention also provides methods of using 1H-1,2,3 triazolium carbenes and metal complexes of 1H-1,2,3 triazolium carbenes in catalytic reactions.
    Type: Application
    Filed: April 26, 2011
    Publication date: August 1, 2013
    Applicant: The Regents of the University of California
    Inventors: Guy Bertrand, Gregorio Gulsado-Barrios, Jean Bouffard, Bruno Donnadieu
  • Publication number: 20130116434
    Abstract: The current application describes tungsten oxo alkylidene complexes for olefin metathesis.
    Type: Application
    Filed: November 7, 2012
    Publication date: May 9, 2013
    Applicants: TRUSTEES OF BOSTON COLLEGE, MASSACHUSETTS INSTITUTE OF TECHNOLOGY
    Inventors: Massachusetts Institute of Technology, Trustees of Boston College
  • Patent number: 8338550
    Abstract: A ring-opening metathesis polymerization (ROMP) reaction is disclosed in which a cyclic alkene compound is subjected to ROMP using a ruthenium ROMP catalyst having heterocyclic ligands in the presence of a compound from which such ligands may be derived. The process includes the step of adding sufficient of an acyclic alkene having a carbon-carbon double bond capable of reacting with the catalytic metal moieties attached to the living end of each of the polymer chains generated in the ROMP reaction to end cap the polymer chains and to generate a olefin metathesis catalyst. The process includes reiterating the polymerization steps by adding further amounts of a cyclic alkene compound. The catalyst may be generated in situ from a precursor compound by the addition of a compound from which heterocyclic ligands may be derived by interaction with the precursor compound.
    Type: Grant
    Filed: July 20, 2011
    Date of Patent: December 25, 2012
    Assignee: Henkel AG & Co. KGaA
    Inventors: Ezat Khosravi, Alan M. Kenwright, Zhanru Yu, David M. Haigh, Lois Hobson
  • Publication number: 20120123133
    Abstract: The invention relates to ruthenium alkylidene complexes having an N-heterocyclic carbene ligand comprising a 5-membered heterocyclic ring having a carbenic carbon atom and at least one nitrogen atom contained within the 5-membered heterocyclic ring, wherein the nitrogen atom is directly attached to the carbenic carbon atom and is substituted by a phenyl ring, and wherein the phenyl ring has a hydrogen at either or both ortho positions and is substituted at at least one ortho or meta position. The invention also relates to an olefin metathesis reactions and particularly to the preparation of tetra-substituted cyclic olefins via a ring-closing metathesis.
    Type: Application
    Filed: August 30, 2011
    Publication date: May 17, 2012
    Applicants: CALIFORNIA INSTITUTE OF TECHNOLOGY, MATERIA, INC.
    Inventors: Jacob BERLIN, Robert H. GRUBBS, Yann SCHRODI, Ian C. STEWART
  • Publication number: 20120095180
    Abstract: The present invention provides metal-free abnormal N-heterocyclic carbenes, also known as imidazol-5-ylidenes and metal complexes of abnormal N-heterocyclic carbenes. The present invention also provides methods of making metal-free abnormal N-heterocyclic carbenes and metal complexes of abnormal N-heterocyclic carbenes. The present invention also provides methods of using metal-free abnormal N-heterocyclic carbenes and metal complexes of abnormal N-heterocyclic carbenes in catalytic reactions.
    Type: Application
    Filed: October 13, 2011
    Publication date: April 19, 2012
    Applicant: The Regents of the University of California Office of Technology Transfer
    Inventors: Guy Bertrand, Bruno Donnadieu, Eugenia Aldeco-Perez
  • Publication number: 20110098497
    Abstract: Novel group 6 organometallic compounds, supported on anions by means of at least one covalent metal-oxygen bond, are obtained by reaction of at least one borate or aluminate comprising at least one hydroxy group with at least one compound of a group 6 transition metal. These compounds are used in a catalytic composition utilized in an olefin metathesis method.
    Type: Application
    Filed: October 26, 2010
    Publication date: April 28, 2011
    Applicant: IFP Energies nouvelles
    Inventors: Ludovic Chahen, Mikaël Berthod, Vinciane Kelsen, Yves Chauvin, Helene Olivier-Bourbigou, Christophe Vallee
  • Publication number: 20110077421
    Abstract: The present invention relates generally to catalysts and processes for the Z-selective formation of internal olefin(s) from terminal olefin(s) via homo-metathesis reactions.
    Type: Application
    Filed: September 30, 2009
    Publication date: March 31, 2011
    Applicant: Massachusetts Institute of Technology
    Inventors: Richard R. Schrock, Annie J. King, Yu Zhao, Margaret M. Flook
  • Patent number: 7838711
    Abstract: The invention relates to a process for carrying out metathesis reactions, wherein the process is carried out continuously and a ruthenium-containing catalyst is used.
    Type: Grant
    Filed: July 7, 2005
    Date of Patent: November 23, 2010
    Assignee: Boehringer Ingelheim International GmbH
    Inventors: Thomas Herweck, Albrecht Jacobi, Thomas Nicola, Michael Wiese
  • Patent number: 7592498
    Abstract: The invention relates to polymeric transition metal catalysts, to processes for preparing them, to intermediates and also to the use of the transition metal catalysts as catalysts in organic reactions, in particular in olefin metathesis reactions.
    Type: Grant
    Filed: December 18, 2007
    Date of Patent: September 22, 2009
    Assignee: LANXESS Deutschland GmbH
    Inventors: Siegfried Blechert, Stephen Connon
  • Publication number: 20080139861
    Abstract: The invention relates to polymeric transition metal catalysts, to processes for preparing them, to intermediates and also to the use of the transition metal catalysts as catalysts in organic reactions, in particular in olefin metathesis reactions.
    Type: Application
    Filed: December 18, 2007
    Publication date: June 12, 2008
    Inventors: Siegfried Blechert, Stephen Connon
  • Patent number: 7250523
    Abstract: Compounds and processes for catalytic ring-opening cyclooligomerization metathesis and ring-closing metathesis of olefins are described. The compound is a molybdenum or tungsten metal (M) complex which comprises an imido ligand (N—R) bound to the M to provide an M=N—R site, an M=C reaction site wherein the C of the M=C reaction site is tethered to the R of the imido ligand via a carbon or carbon and heteroatom (NOS) chain containing 1 to 12 carbon atoms to form a ring structure, and two to four ligands (R?) bound to the M to provide two to four M-R? sites. In particular embodiments, the M-R? sites include each of the oxygens of a dialkoxide ligand or each of the nitrogens of an ?1-pyrrolyl ligand bound to the M.
    Type: Grant
    Filed: October 22, 2003
    Date of Patent: July 31, 2007
    Assignee: Board of Trustees of Michigan State University
    Inventors: Aaron L. Odom, James T. Ciszewski
  • Patent number: 6977318
    Abstract: A method for forming propylene wherein ethylene is employed as a primary feed material in a combination of steps comprising dehydration, skeletal isomerization, and metathesis to form a versatile product mix that can contain one or more of propylene, gasoline, MTBE, and propylene oxide.
    Type: Grant
    Filed: May 4, 2004
    Date of Patent: December 20, 2005
    Assignee: Equistar Chemicals, LP
    Inventor: Robert S. Bridges
  • Publication number: 20040059169
    Abstract: The invention relates to a method for producing hydrocarbons having a modified carbon skeleton by reacting aliphatic hydrocarbons a) with themselves, b) with another aliphatic hydrocarbon or c) with aromatic alkyl substituted hydrocarbons, in the presence of a metal organic catalyst or the hybrid thereof, at a temperature of between 20-400° C. and a pressure of between 0.2-100 bars, wherein the reaction takes place in the presence of hydrogen.
    Type: Application
    Filed: June 25, 2003
    Publication date: March 25, 2004
    Inventors: Dominic Vanoppen, Ekkehard Schwab, Jean-Marie Basset, Jean Thivolle-Cazat, Mostapha Taoufik, Michael Schulz, Arthur Hohn
  • Patent number: 6677495
    Abstract: A process for preparing cyclopentene oligomer mixtures of the formula I comprises reacting in a homogeneously or heterogeneously catalyzed metathesis reaction a hydrocarbon mixture which contains cyclopentene and acyclic monoolefins and which originates from petroleum processing by cracking (C5 fraction); cyclopentene oligomers of the formula I obtainable by this process and their use are also described.
    Type: Grant
    Filed: June 21, 1999
    Date of Patent: January 13, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schwab, Martin Schäfer, Arthur Höhn
  • Publication number: 20020120173
    Abstract: Catalytic process for metathesis of olefins in the presence of a catalyst and a stabilizing agent that is injected into the reaction medium. Application in particular to rebalancing between one another the light olefins that are obtained from steam cracking or catalytic cracking (FCC), such as ethylene, propylene, butenes or pentenes.
    Type: Application
    Filed: January 28, 2000
    Publication date: August 29, 2002
    Inventors: Dominique Commereuc, Paul Mikitenko
  • Patent number: 6437209
    Abstract: Catalytic process for metathesis of olefins in the presence of a catalyst and a stabilizing agent that is injected into the reaction medium. Application in particular to rebalancing between one another the light olefins that are obtained from steam cracking or catalytic cracking (FCC), such as ethylene, propylene, butenes or pentenes.
    Type: Grant
    Filed: January 28, 2000
    Date of Patent: August 20, 2002
    Assignee: Institut Francais du Petrole
    Inventors: Dominique Commereuc, Paul Mikitenko
  • Patent number: 6346652
    Abstract: A composition and method for the catalytic conversion of a racemic mixture of dienes to a cyclic olefin by a ring-closing metathesis (RCM) reaction are disclosed. The composition, a transition metal complex with an M═C reaction site, contains a bidentate dialkoxide of at least 80% optical purity. Because the M═C reaction site is of a sufficient shape specificity, conferred in part by the dialkoxide of sufficient rigidity and a M═N—R1 site, reacting the composition with a mixture of two enantiomeric dienes results in an olefin metathesis product that has at least a 50% enantiomeric excess of one enantiomer in the mixture. A method is also provided for reacting a composition with a racemic diene mixture to generate a metathesis product that has an enantiomeric excess of at least 50%. Methods are also provided for catalytic enantioselective desymmetrization.
    Type: Grant
    Filed: July 13, 1998
    Date of Patent: February 12, 2002
    Assignee: Massachusetts Institute of Technology
    Inventors: Richard R. Schrock, Amir H. Hoveyda
  • Patent number: 6313365
    Abstract: The invention has an object of safely and simply preparing a large amount of a ruthenium metathesis catalyst, which is used as a catalyst for a carbon-carbon bond formation using, particularly, a metathesis reaction. The metathesis catalyst has the following complex composition (A) or (B).
    Type: Grant
    Filed: September 20, 2000
    Date of Patent: November 6, 2001
    Assignee: Takasago International Corporation
    Inventors: Yoji Hori, Yukiharu Iwaya, Tsutomu Hashimoto, Toshimitsu Hagiwara
  • Patent number: 6284939
    Abstract: This invention pertains to a continuous catalytic process, for example, for the metathesis of olefins that uses a catalyst circulating in a moving bed in at least one reaction zone operating in the liquid phase and in a regenerator, with a lift to transfer the deactivated catalyst emerging from the reaction zone to the regenerator, whereby said process is characterized by the fact that the transfer is accomplished by a gas that does not react with the catalyst and with the stripping off of at least a portion of the organic matter that is adsorbed on the deactivated catalyst.
    Type: Grant
    Filed: July 30, 1999
    Date of Patent: September 4, 2001
    Assignee: Institut Francais du Petrole
    Inventors: Frédéric Hoffmann, Philippe Mege, Dominique Commereuc
  • Patent number: 6284852
    Abstract: Activation of ruthenium based catalyst compounds with acid to improve reaction rates and yields of olefin metathesis reactions, including ROMP, RCM, ADMET and cross-metathesis reactions is disclosed. The ruthenium catalyst compounds are ruthenium carbene complexes of the general formula AxLyXzRu═CHR′ where x=0, 1 or 2, y=0, 1 or 2, and z=1 or 2 and where R′ is hydrogen or a substituted or unsubstituted alkyl or aryl, L is any neutral electron donor, X is any anionic ligand, and A is a ligand having a covalent structure connecting a neutral electron donor and an anionic ligand. The use of acid with these catalysts allows for reactions with a wide range of olefins in a variety of solvents, including acid-initiated RIM processes and living ROMP reactions of water-soluble monomers in water.
    Type: Grant
    Filed: October 29, 1998
    Date of Patent: September 4, 2001
    Assignee: California Institute of Technology
    Inventors: David M. Lynn, Eric L. Dias, Robert H. Grubbs, Bernard Mohr
  • Patent number: 6175047
    Abstract: The invention has an object of safely and simply preparing a large amount of a ruthenium metathesis catalyst, which is used as a catalyst for a carbon-carbon bond formation using, particularly, a metathesis reaction. The metathesis catalyst has the following complex composition (A) or (B).
    Type: Grant
    Filed: December 23, 1998
    Date of Patent: January 16, 2001
    Assignee: Takasago International Corporation
    Inventors: Yoji Hori, Yukiharu Iwaya, Tsutomu Hashimoto, Toshimitsu Hagiwara
  • Patent number: 5990369
    Abstract: The present invention relates to a process for the production of light olefins comprising olefins having from 2 to 4 carbon atoms per molecule from an oxygenate feedstock. The process comprises passing the oxygenate feedstock to an oxygenate conversion zone containing a metal alumninophosphate catalyst to produce a light olefin stream. The light olefin stream is fractionated and a portion of the products are metathesized to enhance the yield of the ethylene, propylene, and/or butylene products. Propylene can be metathesized to produce more ethylene, or a combination of ethylene and butene can be metathesized to produce more propylene. This combination of light olefin production and metathesis, or disproportionation provides flexibility to overcome the equilibrium limitations of the metal aluminophosphate catalyst in the oxygenate conversion zone. In addition, the invention provides the advantage of extended catalyst life and greater catalyst stability in the oxygenate conversion zone.
    Type: Grant
    Filed: February 9, 1998
    Date of Patent: November 23, 1999
    Assignee: UOP LLC
    Inventors: Paul T. Barger, R. Joe Lawson, Bipin V. Vora
  • Patent number: 5942653
    Abstract: A process for treating unsaturated hydrocarbons comprises subjecting an unsaturated hydrocarbon component to metathesis in the presence of a catalyst system comprising silica, alumina and an alkyl tin compound, thereby to form one or more different hydrocarbons.
    Type: Grant
    Filed: September 6, 1996
    Date of Patent: August 24, 1999
    Assignee: Sasol Technology (Proprietary) Limited
    Inventors: Jan Adriaan Kruger Du Plessis, Hermanus Cornelius Moolman Vosloo, Alta Jansen Van Rensburg
  • Patent number: 5939504
    Abstract: Compositions and methods for catalyzing and controlling the rate of olefin metathesis reactions including Ring Opening Metathesis Polymerization (ROMP) reactions. The molding of polymer articles using ROMP polymers. The composition includes a Ruthenium or Osmium carbene complex catalyst and a gel modification additive. The Ruthenium or Osmium carbene complex catalyst having the formula ##STR1## where M may be Os or Ru; R and R.sup.1 may be the same or different and may be hydrogen or a substituent group including C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.1 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl and C.sub.1 -C.sub.20 alkylsulfinyl; X and X.sup.1 may be the same or different and may be any anionic ligand; and L and L.sup.1 may be the same or different and may be neutral electron donor.
    Type: Grant
    Filed: December 2, 1996
    Date of Patent: August 17, 1999
    Assignee: Advanced Polymer Technologies
    Inventors: Charles S. Woodson, Jr., Robert H. Grubbs
  • Patent number: 5905055
    Abstract: The invention relates to a heterogeneous metathesis catalyst containing a support, a metal compound chosen from the group consisting of tungsten, rhenium and molybdenum, and a promoter, the promoter consisting of a niobium compound. The catalyst according to the invention has a high activity at low temperatures. The invention also relates to a process for the metathesis of olefins.
    Type: Grant
    Filed: October 31, 1996
    Date of Patent: May 18, 1999
    Assignee: DSM N.V.
    Inventors: Ludo C. G. C. Verdonck, Francis W. C. Verpoort, Antoine R. J. Bossuyt
  • Patent number: 5898091
    Abstract: For the conversion of an olefinic C.sub.4 or C.sub.5 cut to an alkyl-tertiobutylether or alkyl-tertioamylether and to propylene, by metathesis, the process comprises four successive steps: (1) selective hydrogenation of the diolefins with simultaneous isomerisation of the alpha olefins to internal olefins; (2) etherification of the isoolefins; (3) elimination of oxygen-containing impurities; (4) metathesis of internal olefins with ethylene. The process has application, e.g., to C.sub.4 and C.sub.5 steam cracking cuts.
    Type: Grant
    Filed: May 10, 1996
    Date of Patent: April 27, 1999
    Assignee: Institut Francais du Petrole
    Inventors: Jean-Alain Chodorge, Dominique Commereuc, Jean Cosyns, Didier Duee, Bernard Torck
  • Patent number: 5728917
    Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and functional groups C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: March 17, 1998
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, SonBinh T. Nguyen
  • Patent number: 5698761
    Abstract: The invention relates to the use of cyclic organometallic compounds as components in coordination catalyst systems, to corresponding coordination catalyst systems and also to processes for the preparation of polymers by coordination polymerization and of unsaturated hydrocarbons by catalyzed metathesis of alkenes and alkynes using such coordination catalyst systems.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 16, 1997
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Ludwig Pohl, Eike Poetsch, Herbert Schumann, Karin Weiss, Karl-Heinz Thiele, Hans-Ludwig Hirsch
  • Patent number: 5675051
    Abstract: The invention concerns a catalytic olefin disproportion (also known as metathesis) process wherein the catalyst produced by dissolving a tungsten and/or molybdenum compound, more particularly a tungsten and/or molybdenum halide substituted with one or more phenoxo groups containing at least two hydrocarbon substituents in the ortho, ortho' positions, in a medium produced by mixing at least one quaternary ammonium halide and/or at least one quaternary phosphonium halide, at least one aluminium halide, and an organometallic aluminium compound.
    Type: Grant
    Filed: November 1, 1995
    Date of Patent: October 7, 1997
    Assignee: Institut Francais Du Petrole
    Inventors: Yves Chauvin, Francoise Di Marco-Van Tiggelen
  • Patent number: 5519101
    Abstract: A polymerization process for preparation of oligomers and polymers having at least one internal carbon-to-carbon double bond and containing functional groups comprising terminal carbon-to-carbon double bonds is disclosed. The polymerization process is substantially free of side reactions comprising double bond migration. The oligomers and polymers are prepared from acyclic polyenes of from 2 to about 30 carbon atoms. The catalyst system comprises a metathesis catalyst (A) comprising a transition metal compound, an activator (B) selected from the group consisting of organic tin compounds and organic aluminum halides and (C) an organic Lewis base. Yields are at least 60% of theoretical based on acyclic polyene reactant.
    Type: Grant
    Filed: May 27, 1993
    Date of Patent: May 21, 1996
    Assignee: Amoco Corporation
    Inventors: Philip O. Nubel, Vahid Bagheri
  • Patent number: 5254786
    Abstract: This present invention relates to a disproportionation catalyst and to a process for preparing a disproportionation catalyst comprising forming a calcined composite comprising at least one of molybdenum and rhenium supported on an inorganic oxide support and contacting the calcined composite with an organoborane compound. The invention further relates to a process for the disproportionation of olefinic hydrocarbons comprising contacting at least one olefinic hydrocarbon with a catalyst comprising at least one of molybdenum and rhenium supported on an inorganic oxide support promoted with an organoborane compound. More specifically, the invention relates to the uses of an organoborane compound promoted molybdenum and rhenium supported on an inorganic oxide support for the production of linear alpha olefins from a mixture of internal olefins and ethylene.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: October 19, 1993
    Assignee: Shell Oil Company
    Inventors: Jiang-Jen Lin, Randall T. DePue, Howard L. Fong
  • Patent number: 5095165
    Abstract: The invention discloses that hydrocarbon lubricants containing olefinic unsaturation participate in an olefin metathesis reaction with alkenes containing polar functional groups to provide an equilibrium mixture containing hydrocarbon lubricants containing the polar groups of the alkenes. The discovery is particularly applicable to the functionalization of near linear lubricants prepared from the oligomerization of propylene using surface deactivated zeolite or lubricants prepared by the oligomerization of C.sub.6 -C.sub.20 alpha olefins using coordination catalyst. Functionalized groups can be incorporated that impart a wide range of properties to the lubricant such as anti-wear or anti-corrosion resistance, or improve the compatibility of the lubricant with other additives.
    Type: Grant
    Filed: March 21, 1990
    Date of Patent: March 10, 1992
    Assignee: Mobil Oil Corporation
    Inventor: Catherine S. Hsia Chen
  • Patent number: 5093540
    Abstract: This invention relates to a two step process for converting linear paraffins to alpha olefins. The first step comprises contacting said paraffins with a catalyst comprising an oxide an alkali or alkaline earth metal optionally dispersed on a refractory and porous carrier. The product of this process contains only small amounts of aromatics and branched olefins. The cracked product is then converted to an olefin product containing primarily alph olefins by contacting with ethylene and a disproportionation catalyst as disproportionation conditions.
    Type: Grant
    Filed: August 31, 1990
    Date of Patent: March 3, 1992
    Assignee: Shell Oil Company
    Inventors: Thomas C. Forschner, Thomas F. Brownscombe, Jiang-Jen Lin
  • Patent number: 5057644
    Abstract: This invention relates to a process for the purification of an alpha olefinic feedstock contaminated with internal olefins which process comprises contacting said alpha olefinic feedstock with ethylene in the presence of a catalyst comprising an organoborane promoted alkali metal doped molybdenum and/or rhenium oxide supported on an inorganic oxide support.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: October 15, 1991
    Assignee: Shell Oil Company
    Inventors: Jiang-Jen Lin, Randall T. De Pue, Keith M. Kreitman