Using Organic Extraneous Agent Patents (Class 585/645)
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Patent number: 11203679Abstract: 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: GrantFiled: April 26, 2019Date of Patent: December 21, 2021Assignee: ARLANXEO DEUTSCHLAND GMBHInventors: Silvia Schnitzler, Sarah David
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Patent number: 11059940Abstract: 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: GrantFiled: May 13, 2020Date of Patent: July 13, 2021Assignee: University of Florida Research Foundation, IncorporatedInventors: Kenneth B. Wagener, Michael H. Bell
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Patent number: 9816051Abstract: 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: GrantFiled: March 18, 2013Date of Patent: November 14, 2017Assignee: Croda International PLCInventors: Bastiaan Wels, Hans Ridderikhoff, Tanja Van Bergen-Brenkman, Dessy Liminto
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Patent number: 9809513Abstract: 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: GrantFiled: November 20, 2014Date of Patent: November 7, 2017Assignee: Lummus Technology Inc.Inventors: Sukwon Choi, Bala Ramachandran
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Patent number: 9556296Abstract: 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: GrantFiled: April 25, 2014Date of Patent: January 31, 2017Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, IFP ENERGIES NOUVELLES, ECOLE NATIONALE SUPERIEURE DE CHIMIE DE RENNESInventors: Helene Olivier-Bourbigou, Francois Hugues, Severine Forget, Mathieu Rouen, Marc Mauduit
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Patent number: 8993470Abstract: Organometallic compounds of the general formula (I), in which M=Mo, W, are claimed.Type: GrantFiled: March 31, 2011Date of Patent: March 31, 2015Assignee: Studiengesellschaft Kohle mbHInventors: Alois Fuerstner, Johannes Heppekausen, Volker Hickmann, Robert Stade
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Patent number: 8993823Abstract: 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: GrantFiled: June 25, 2014Date of Patent: March 31, 2015Assignee: UOP LLCInventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
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Patent number: 8895794Abstract: 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: GrantFiled: March 17, 2010Date of Patent: November 25, 2014Assignee: Chevron U.S.A. Inc.Inventors: Hye-Kyung Timken, Shawn Winter, Howard S. Lacheen, Sven Ivar Hommeltoft
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Publication number: 20140309433Abstract: 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: ApplicationFiled: April 10, 2014Publication date: October 16, 2014Inventors: Vanessa M. Marx, Mohand-Ameziane Melaimi, Scott C. Virgil, Benjamin K. Keitz, Robert H. Grubbs, Guy Bertrand
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Publication number: 20140275595Abstract: 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: ApplicationFiled: March 13, 2014Publication date: September 18, 2014Applicant: ELEVANCE RENEWABLE SCIENCES, INC.Inventors: Keith M. Wampler, Steven A. Cohen, Georg E. Frater, Levente Ondi, Jeno Varga
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Publication number: 20140235913Abstract: 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: ApplicationFiled: February 21, 2014Publication date: August 21, 2014Applicant: IFP ENERGIES NOUVELLESInventors: Helene OLIVIER-BOURBIGOU, Mikael BERTHOD
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Publication number: 20140200382Abstract: 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: ApplicationFiled: August 13, 2013Publication date: July 17, 2014Applicant: MATERIA, INC.Inventor: Yann SCHRODI
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Publication number: 20130331630Abstract: 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: ApplicationFiled: June 6, 2013Publication date: December 12, 2013Inventors: Bradon J. Dreyer, Brian M. Pease
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Publication number: 20130289327Abstract: 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: ApplicationFiled: June 10, 2013Publication date: October 31, 2013Inventor: Yann Schrodi
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Patent number: 8519069Abstract: 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: GrantFiled: July 7, 2010Date of Patent: August 27, 2013Assignee: RIMTEC CorporationInventor: Renata Drozdzak
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Publication number: 20130204026Abstract: 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: ApplicationFiled: March 24, 2011Publication date: August 8, 2013Applicant: MATERIA, INC.Inventor: Yann Schrodi
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Publication number: 20130197178Abstract: 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: ApplicationFiled: April 26, 2011Publication date: August 1, 2013Applicant: The Regents of the University of CaliforniaInventors: Guy Bertrand, Gregorio Gulsado-Barrios, Jean Bouffard, Bruno Donnadieu
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Publication number: 20130116434Abstract: The current application describes tungsten oxo alkylidene complexes for olefin metathesis.Type: ApplicationFiled: November 7, 2012Publication date: May 9, 2013Applicants: TRUSTEES OF BOSTON COLLEGE, MASSACHUSETTS INSTITUTE OF TECHNOLOGYInventors: Massachusetts Institute of Technology, Trustees of Boston College
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Patent number: 8338550Abstract: 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: GrantFiled: July 20, 2011Date of Patent: December 25, 2012Assignee: Henkel AG & Co. KGaAInventors: Ezat Khosravi, Alan M. Kenwright, Zhanru Yu, David M. Haigh, Lois Hobson
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Publication number: 20120123133Abstract: 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: ApplicationFiled: August 30, 2011Publication date: May 17, 2012Applicants: CALIFORNIA INSTITUTE OF TECHNOLOGY, MATERIA, INC.Inventors: Jacob BERLIN, Robert H. GRUBBS, Yann SCHRODI, Ian C. STEWART
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Publication number: 20120095180Abstract: 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: ApplicationFiled: October 13, 2011Publication date: April 19, 2012Applicant: The Regents of the University of California Office of Technology TransferInventors: Guy Bertrand, Bruno Donnadieu, Eugenia Aldeco-Perez
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Publication number: 20110098497Abstract: 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: ApplicationFiled: October 26, 2010Publication date: April 28, 2011Applicant: IFP Energies nouvellesInventors: Ludovic Chahen, Mikaël Berthod, Vinciane Kelsen, Yves Chauvin, Helene Olivier-Bourbigou, Christophe Vallee
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Publication number: 20110077421Abstract: 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: ApplicationFiled: September 30, 2009Publication date: March 31, 2011Applicant: Massachusetts Institute of TechnologyInventors: Richard R. Schrock, Annie J. King, Yu Zhao, Margaret M. Flook
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Patent number: 7838711Abstract: 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: GrantFiled: July 7, 2005Date of Patent: November 23, 2010Assignee: Boehringer Ingelheim International GmbHInventors: Thomas Herweck, Albrecht Jacobi, Thomas Nicola, Michael Wiese
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Patent number: 7592498Abstract: 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: GrantFiled: December 18, 2007Date of Patent: September 22, 2009Assignee: LANXESS Deutschland GmbHInventors: Siegfried Blechert, Stephen Connon
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Publication number: 20080139861Abstract: 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: ApplicationFiled: December 18, 2007Publication date: June 12, 2008Inventors: Siegfried Blechert, Stephen Connon
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Patent number: 7250523Abstract: 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: GrantFiled: October 22, 2003Date of Patent: July 31, 2007Assignee: Board of Trustees of Michigan State UniversityInventors: Aaron L. Odom, James T. Ciszewski
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Patent number: 6977318Abstract: 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: GrantFiled: May 4, 2004Date of Patent: December 20, 2005Assignee: Equistar Chemicals, LPInventor: Robert S. Bridges
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Publication number: 20040059169Abstract: 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: ApplicationFiled: June 25, 2003Publication date: March 25, 2004Inventors: Dominic Vanoppen, Ekkehard Schwab, Jean-Marie Basset, Jean Thivolle-Cazat, Mostapha Taoufik, Michael Schulz, Arthur Hohn
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Patent number: 6677495Abstract: 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: GrantFiled: June 21, 1999Date of Patent: January 13, 2004Assignee: BASF AktiengesellschaftInventors: Peter Schwab, Martin Schäfer, Arthur Höhn
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Publication number: 20020120173Abstract: 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: ApplicationFiled: January 28, 2000Publication date: August 29, 2002Inventors: Dominique Commereuc, Paul Mikitenko
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Patent number: 6437209Abstract: 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: GrantFiled: January 28, 2000Date of Patent: August 20, 2002Assignee: Institut Francais du PetroleInventors: Dominique Commereuc, Paul Mikitenko
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Patent number: 6346652Abstract: 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: GrantFiled: July 13, 1998Date of Patent: February 12, 2002Assignee: Massachusetts Institute of TechnologyInventors: Richard R. Schrock, Amir H. Hoveyda
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Patent number: 6313365Abstract: 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: GrantFiled: September 20, 2000Date of Patent: November 6, 2001Assignee: Takasago International CorporationInventors: Yoji Hori, Yukiharu Iwaya, Tsutomu Hashimoto, Toshimitsu Hagiwara
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Patent number: 6284939Abstract: 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: GrantFiled: July 30, 1999Date of Patent: September 4, 2001Assignee: Institut Francais du PetroleInventors: Frédéric Hoffmann, Philippe Mege, Dominique Commereuc
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Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water
Patent number: 6284852Abstract: 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: GrantFiled: October 29, 1998Date of Patent: September 4, 2001Assignee: California Institute of TechnologyInventors: David M. Lynn, Eric L. Dias, Robert H. Grubbs, Bernard Mohr -
Patent number: 6175047Abstract: 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: GrantFiled: December 23, 1998Date of Patent: January 16, 2001Assignee: Takasago International CorporationInventors: Yoji Hori, Yukiharu Iwaya, Tsutomu Hashimoto, Toshimitsu Hagiwara
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Patent number: 5990369Abstract: 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: GrantFiled: February 9, 1998Date of Patent: November 23, 1999Assignee: UOP LLCInventors: Paul T. Barger, R. Joe Lawson, Bipin V. Vora
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Patent number: 5942653Abstract: 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: GrantFiled: September 6, 1996Date of Patent: August 24, 1999Assignee: Sasol Technology (Proprietary) LimitedInventors: Jan Adriaan Kruger Du Plessis, Hermanus Cornelius Moolman Vosloo, Alta Jansen Van Rensburg
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Patent number: 5939504Abstract: 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: GrantFiled: December 2, 1996Date of Patent: August 17, 1999Assignee: Advanced Polymer TechnologiesInventors: Charles S. Woodson, Jr., Robert H. Grubbs
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Patent number: 5905055Abstract: 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: GrantFiled: October 31, 1996Date of Patent: May 18, 1999Assignee: DSM N.V.Inventors: Ludo C. G. C. Verdonck, Francis W. C. Verpoort, Antoine R. J. Bossuyt
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Patent number: 5898091Abstract: 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: GrantFiled: May 10, 1996Date of Patent: April 27, 1999Assignee: Institut Francais du PetroleInventors: Jean-Alain Chodorge, Dominique Commereuc, Jean Cosyns, Didier Duee, Bernard Torck
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Patent number: 5728917Abstract: 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: GrantFiled: October 30, 1995Date of Patent: March 17, 1998Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, SonBinh T. Nguyen
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Patent number: 5698761Abstract: 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: GrantFiled: June 7, 1995Date of Patent: December 16, 1997Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Ludwig Pohl, Eike Poetsch, Herbert Schumann, Karin Weiss, Karl-Heinz Thiele, Hans-Ludwig Hirsch
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Patent number: 5675051Abstract: 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: GrantFiled: November 1, 1995Date of Patent: October 7, 1997Assignee: Institut Francais Du PetroleInventors: Yves Chauvin, Francoise Di Marco-Van Tiggelen
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Patent number: 5519101Abstract: 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: GrantFiled: May 27, 1993Date of Patent: May 21, 1996Assignee: Amoco CorporationInventors: Philip O. Nubel, Vahid Bagheri
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Patent number: 5254786Abstract: 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: GrantFiled: December 20, 1991Date of Patent: October 19, 1993Assignee: Shell Oil CompanyInventors: Jiang-Jen Lin, Randall T. DePue, Howard L. Fong
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Patent number: 5095165Abstract: 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: GrantFiled: March 21, 1990Date of Patent: March 10, 1992Assignee: Mobil Oil CorporationInventor: Catherine S. Hsia Chen
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Patent number: 5093540Abstract: 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: GrantFiled: August 31, 1990Date of Patent: March 3, 1992Assignee: Shell Oil CompanyInventors: Thomas C. Forschner, Thomas F. Brownscombe, Jiang-Jen Lin
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Patent number: 5057644Abstract: 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: GrantFiled: October 31, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventors: Jiang-Jen Lin, Randall T. De Pue, Keith M. Kreitman