Diolefin Product Patents (Class 585/601)
  • Patent number: 8937207
    Abstract: The present invention relates to a process for carrying out a chemical reaction in the presence of a ruthenium-carbene complex supported on silicon dioxide in a continuously operated reactor and also the use of corresponding supported catalysts in continuously operated reactors.
    Type: Grant
    Filed: December 20, 2011
    Date of Patent: January 20, 2015
    Inventors: Richard Dehn, Stephan Deuerlein, Manuel Danz, Michael Limbach, Joaquim Henrique Teles
  • Patent number: 8933285
    Abstract: Methods are provided for producing a jet fuel composition from a feedstock comprising a natural oil. The methods comprise reacting the feedstock with a low-weight olefin in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product. The methods further comprise hydrogenating the metathesized product under conditions sufficient to form a jet fuel composition.
    Type: Grant
    Filed: November 25, 2009
    Date of Patent: January 13, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Melvin L. Luetkens, Jr., Steven A. Cohen, Chander Balakrishnan
  • Patent number: 8906658
    Abstract: The invention features methods for producing isoprene from cultured cells wherein the cells in the stationary phase. The invention also provides compositions that include these cultured cells and/or increased amount of isoprene. The invention also provides for systems that include a non-flammable concentration of isoprene in the gas phase. Additionally, the invention provides isoprene compositions, such as compositions with increased amount of isoprene or increased purity.
    Type: Grant
    Filed: January 14, 2013
    Date of Patent: December 9, 2014
    Assignees: Danisco US Inc., The Goodyear Tire & Rubber Company
    Inventors: Anthony R. Calabria, Marguerite A. Cervin, Gopal K. Chotani, Richard La Duca, Joseph C. McAuliffe, Michael C. Miller, Timothy A. Sabo, Karl J. Sanford, Erin L. Spring, Gregory M. Whited
  • Patent number: 8722953
    Abstract: The invention relates to a process for preparing substituted or unsubstituted 1,7-diolefins by hydrodimerizing non-cyclic olefins having at least two conjugated double bonds in the presence of a reducing agent and of a catalyst, wherein the catalyst used is a metal-carbene complex.
    Type: Grant
    Filed: June 6, 2007
    Date of Patent: May 13, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Volker Brehme, Manfred Neumann, Frank Bauer, Elke Fiebig-Bauer, Franz Rudolf Bauer, Johanna Elisabeth Bauer, Dirk Roettger
  • Patent number: 8624042
    Abstract: The invention describes a process for the selective dimerization of ethylene to but-1-ene using a catalytic composition comprising at least one organometallic titanium complex, said organometallic complex containing at least one alkoxy type ligand functionalized by a heteroatom selected from nitrogen, oxygen, phosphorus, sulphur, arsenic and antimony or by an aromatic group.
    Type: Grant
    Filed: May 17, 2011
    Date of Patent: January 7, 2014
    Assignee: IFP Energies Nouvelles
    Inventors: Fabien Grasset, Lionel Magna
  • Patent number: 8524969
    Abstract: A method for the dehydrogenation of hydrocarbons to alkenes, such as n-pentene to piperylene and n-butane to butadiene at pressures less than atmospheric utilizing a dehydrogenation catalyst are disclosed. Embodiments involve operating the dehydrogenation reactor at a pressure of 1,000 mbar or less.
    Type: Grant
    Filed: July 21, 2009
    Date of Patent: September 3, 2013
    Assignee: Fina Technology, Inc.
    Inventors: James Butler, Olga Khabashesku, James T. Merrill
  • Patent number: 8492603
    Abstract: A process for the dimerization of isoolefins, including: contacting an isoolefin with a solid catalyst composition passivated with at least one of an ether, an alcohol, and water; wherein the solid catalyst composition comprises at least one of a solid phosphoric acid catalyst and a resin of a macroporous matrix of polyvinyl aromatic compound crosslinked with a divinyl compound and having thereon from about 3 to 5 milli equivalents of sulfonic acid groups per gram of dry resin; and wherein at least 50% to less than 100% of acid groups in the solid catalyst composition are neutralized with a metal of Al, Fe, Zn, Cu, Ni, or mixtures thereof. The catalyst may be metalized prior to placement in a reactor or may be metalized in situ.
    Type: Grant
    Filed: January 12, 2009
    Date of Patent: July 23, 2013
    Assignee: Catalytic Distillation Technologies
    Inventors: Lawrence A. Smith, William M. Cross
  • Patent number: 8410328
    Abstract: A method of preparing multicomponent bismuth molybdate catalysts composed of four metal components and a method of preparing 1,3-butadiene using the catalyst, and particularly, to multicomponent bismuth molybdate catalysts composed of a divalent cationic metal, a trivalent cationic metal, bismuth and molybdenum, a preparation method thereof, and a method of preparing 1,3-butadiene from a C4 mixture including n-butene and n-butane using oxidative dehydrogenation are described.
    Type: Grant
    Filed: August 24, 2008
    Date of Patent: April 2, 2013
    Assignees: SK Innovation Co., Ltd., SK Global Chemical Co., Ltd.
    Inventors: Young Min Chung, Tae Jin Kim, Seong Jun Lee, Yong Seung Kim, Seung Hoon Oh, In Kyu Song, Hee Soo Kim, Ji Chul Jung, Ho Won Lee
  • Patent number: 8258362
    Abstract: A process for the synthesis of linear ?,?-diolefins from an allylic substrate comprises the steps of a) forming the bis-Grignard reagent XMgCH2(CH2)nCH2MgX from an ?,?-acyclic dihalide with X being a halogen; b) preparing a solution comprising an allylic substrate and a copper catalyst; c) catalyzing a coupling reaction by adding to the solution of step (b) the bis-Grignard reagent of step (a); and d) isolating and purifying the ?,?-olefin coupling reaction product.
    Type: Grant
    Filed: May 4, 2010
    Date of Patent: September 4, 2012
    Assignee: ISP Investments Inc.
    Inventors: Krishnamurthy Nacharaju, Paul D. Taylor, Mark J. Cooney, Larry A. Crabtree
  • Publication number: 20120165588
    Abstract: The present invention relates to a process for carrying out a chemical reaction in the presence of a ruthenium-carbene complex supported on silicon dioxide in a continuously operated reactor and also the use of corresponding supported catalysts in continuously operated reactors.
    Type: Application
    Filed: December 20, 2011
    Publication date: June 28, 2012
    Applicant: BASF SE
    Inventors: Richard Dehn, Stephan Deuerlein, Manuel Danz, Michael Limbach, Joaquim Henrique Teles
  • Publication number: 20110313222
    Abstract: One exemplary embodiment can be an apparatus for isomerizing a hydrocarbon stream rich in a C4 hydrocarbon and/or at least one of a C5 and C6 hydrocarbon. The apparatus can include: a first drier and a second drier adapted to receive a fluid including at least one reactant; and a reaction zone communicating with the first drier to receive the fluid including at least one reactant and with the second drier to receive the regenerant. Generally, the first drier operates at a first condition to dry the fluid including at least one reactant and the second drier operates at a second condition during regeneration with a regenerant. The regenerant is displaced from the drier using a down-flow regenerant displacement assembly.
    Type: Application
    Filed: September 1, 2011
    Publication date: December 22, 2011
    Applicant: UOP LLC
    Inventors: Bryan S. Garney, Jocelyn C. Daguio, Kurt A. Detrick, Douglas A. Becci, David J. Shecterle, John M. Krupczak, Andrew D. Mezera
  • Patent number: 8067631
    Abstract: To provide a method of rapid methylation of alkenes, which is applicable to the preparation of a PET tracer and which enables alkenes to be methylated through cross coupling between SP2 (alkenyl) and SP3 (alkyl) carbon atoms rapidly and in a high yield. Methyl iodide and an alkenyltrialkylstannane are subjected to cross coupling in an aprotic polar solvent in the presence of a palladium complex having a valence of 0, a phosphine ligand, a cuprous halide, and a carbonate and/or alkali metal fluoride.
    Type: Grant
    Filed: October 6, 2006
    Date of Patent: November 29, 2011
    Assignee: Gifu University
    Inventors: Masaaki Suzuki, Takamitsu Hosoya
  • Publication number: 20110288308
    Abstract: The invention describes a process for the selective dimerization of ethylene to but-1-ene using a catalytic composition comprising at least one organometallic titanium complex, said organometallic complex containing at least one alkoxy type ligand functionalized by a heteroatom selected from nitrogen, oxygen, phosphorus, sulphur, arsenic and antimony or by an aromatic group.
    Type: Application
    Filed: May 17, 2011
    Publication date: November 24, 2011
    Applicant: IFP Energies nouvelle
    Inventors: Fabian GRASSET, Lionel MAGNA
  • Publication number: 20110124868
    Abstract: This invention relates generally to olefin metathesis, more particularly, to tri- or tetra-substituted imidazolinium salts which are precursors to N-heterocyclic carbene (NHC) ligands with tri- or tetra-substituted imidazolinium rings, organometallic ruthenium complexes comprising gem di-substituted imidazolinium NHC ligands, organometallic ruthenium complexes comprising tri- or tetra-substituted imidazolinium NHC ligands, and to olefin metathesis methods using them. The catalysts and methods of the invention have utility in the fields of catalysis, organic synthesis, and industrial chemistry.
    Type: Application
    Filed: April 9, 2009
    Publication date: May 26, 2011
    Applicants: MATERIA, INC., CALIFORNIA INSTITUTE OF TECHNOLOGY
    Inventors: Robert H. Grubbs, Cheol Keun Chung, Jean-Baptiste Bourg, Kevin Kuhn
  • Publication number: 20100280299
    Abstract: A process for the synthesis of linear ?,?-diolefins from an allylic substrate comprises the steps of a) forming the bis-Grignard reagent XMgCH2(CH2)nCH2MgX from an ?,?-acyclic dihalide with X being a halogen; b) preparing a solution comprising an allylic substrate and a copper catalyst; c) catalyzing a coupling reaction by adding to the solution of step (b) the bis-Grignard reagent of step (a); and d) isolating and purifying the ?,?-olefin coupling reaction product.
    Type: Application
    Filed: May 4, 2010
    Publication date: November 4, 2010
    Applicant: ISP Investments Inc.
    Inventors: Krishnamurthy Nacharaju, Paul D. Taylor, Mark J. Cooney, Larry A. Crabtree
  • Publication number: 20100179362
    Abstract: A process for the dimerization of isoolefins, including: contacting an isoolefin with a solid catalyst composition passivated with at least one of an ether, an alcohol, and water; wherein the solid catalyst composition comprises at least one of a solid phosphoric acid catalyst and a resin of a macroporous matrix of polyvinyl aromatic compound crosslinked with a divinyl compound and having thereon from about 3 to 5 milli equivalents of sulfonic acid groups per gram of dry resin; and wherein at least 50% to less than 100% of acid groups in the solid catalyst composition are neutralized with a metal of Al, Fe, Zn, Cu, Ni, or mixtures thereof. The catalyst may be metalized prior to placement in a reactor or may be metalized in situ.
    Type: Application
    Filed: January 12, 2009
    Publication date: July 15, 2010
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Lawrence A. Smith, JR., William M. Cross, JR.
  • Publication number: 20100144987
    Abstract: This invention relates to olefin metathesis catalysts general formula (I): having a thiazol-2-ylidene ligand of general formula (II): The catalysts have been found to be particularly good initiators of (a) ring-closing metathesis reactions used to prepare tetra-substituted cyclic olefins, and (b) cross-metathesis reactions used to prepare tri-substituted and di-substituted olefins.
    Type: Application
    Filed: November 20, 2007
    Publication date: June 10, 2010
    Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGY
    Inventors: George C. Vougioukaiakis, Robert H. Grubbs
  • Patent number: 7645914
    Abstract: Process for telomerizing noncyclic olefins having at least two conjugated double bonds with at least one nucleophile using a catalyst containing a metal of group 8, 9 or 10 of the Periodic Table of the Elements, wherein hydrogen is added via a hydrogen source to the process in at least one process step in the overall telomerization process.
    Type: Grant
    Filed: August 23, 2005
    Date of Patent: January 12, 2010
    Assignee: Evonik Oxeno GmbH
    Inventors: Cornelia Borgmann, Dirk Roettger, Dagmara Ortmann, Reiner Bukohl, Stephan Houbrechts, Franz Nierlich
  • Publication number: 20080167509
    Abstract: A method for treating a hydrocarbon solvent, the method comprising continuously introducing a hydrocarbon solvent to a liquid medium containing hydrogen ions; allowing the hydrocarbon solvent to be in contact with the liquid medium for at least 1 minute; continuously removing hydrocarbon solvent from the liquid medium to provide a treated hydrocarbon solvent stream.
    Type: Application
    Filed: December 28, 2007
    Publication date: July 10, 2008
    Inventors: James H. Pawlow, William L. Hergenrother
  • Patent number: 7179632
    Abstract: There is disclosed a method for preparing allicin which comprises the following steps: (a) mechanically treating a natural source of alliinase to release alliinase therefrom; (b) contacting the mechanically treated alliinase source with an aqueous solution of allicin containing alliin at a concentration greater than that found in raw garlic, whereby the alliin is enzymatically converted to allicin by the alliinase released from the alliinase source; and optionally (c) extracting the resultant allicin into a low boiling point non-polar organic solvent.
    Type: Grant
    Filed: July 4, 2002
    Date of Patent: February 20, 2007
    Assignee: Neem Biotech Ltd.
    Inventors: David Michael Williams, Chandra Mohan Pant
  • Patent number: 7157533
    Abstract: A process is described for obtaining from an “FCC” initial C5 fraction which is enriched with isoprene and purified and usable for the selective polymerization of isoprene. A process is also described for obtaining an isoprene homopolymer from a polymerization medium comprising isoprene and at least one methyl butene, such as said “FCC” C5 fraction which is enriched with isoprene and purified. The process of obtaining the final fraction from the initial C5 fraction includes: a catalytic hydrogenation reaction of said initial C5 fraction by a palladium-based catalyst, which produces an intermediate C5 fraction comprising n-pentenes in a mass ratio which is less than 0.
    Type: Grant
    Filed: July 21, 2005
    Date of Patent: January 2, 2007
    Assignee: Michelin Recherche et Technique S.A.
    Inventor: Sylvie Gandon-Pain
  • Patent number: 7115790
    Abstract: The invention relates to a process for preparing 1-octene by telomerization of 1,3-butadiene using a reducing agent in the presence of a telomerization catalyst and partial hydrogenation of the octadiene obtained in this way.
    Type: Grant
    Filed: September 18, 2002
    Date of Patent: October 3, 2006
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Matthias Beller, Ralf Jackstell, Holger Klein, Dirk Roettger, Dietrich Maschmeyer, Silvia Santiago Fernandez
  • Patent number: 7102046
    Abstract: The present invention relates to a process for the arylation of olefins by reaction of haloaromatics or arylsulfonates with olefins in the presence of a palladium catalyst, a bulky nitrogen base and a salt.
    Type: Grant
    Filed: November 27, 2002
    Date of Patent: September 5, 2006
    Assignee: Bayer Aktiengesellschaft
    Inventors: Florian Rampf, Markus Eckert
  • Patent number: 6841711
    Abstract: A process for making a lube base stock wherein an olefinic feedstock is contacted with an oligomerization catalyst in a catalytic distillation unit to produce a product having a higher number average molecular weight than the olefinic feedstock. That product is separated zone in the catalytic distillation unit into a light byproduct fraction and a heavy product fraction that includes hydrocarbons in a lube base stock range.
    Type: Grant
    Filed: January 11, 2001
    Date of Patent: January 11, 2005
    Assignee: Chevron U.S.A. Inc.
    Inventors: Russell R. Krug, Dennis J. O'Rear
  • Publication number: 20040242949
    Abstract: Process for the telomerization of a conjugated diene,
    Type: Application
    Filed: July 1, 2004
    Publication date: December 2, 2004
    Inventors: Eit Drent, Michael Rolf Eberhard, Paul Gerald Pringle, Renata Helena van der Made
  • Patent number: 6667423
    Abstract: For the production of a diene a process in three stages comprises a stage a) for decomposition of at least one tertiary alkyl ether in a mixture that contains at least one tertiary olefin, at least one alcohol and at least one residual ether, in the presence of a catalyst that comprises at least one mineral solid that is grafted by at least one organic group such as alkyl sulfonic acid, sulfonic aryl and/or sulfonic alkylaryl, a stage b) for purification of the olefin that is obtained in stage a), and a stage c) for oxidizing dehydrogenation of the tertiary olefin that is obtained in stage b) in the presence of a catalyst under conditions for obtaining a diene.
    Type: Grant
    Filed: September 9, 1999
    Date of Patent: December 23, 2003
    Assignee: Institut Francais du Petrole
    Inventors: Claire Dumonteil, Alain Forestiere, Marie-Claire Marion
  • Publication number: 20030114725
    Abstract: For the production of a diene a process in three stages comprises
    Type: Application
    Filed: September 9, 1999
    Publication date: June 19, 2003
    Inventors: CLAIRE DUMONTEIL, ALAIN FORESTIERE, MARIE-CLAIRE MARION
  • Patent number: 6333443
    Abstract: A process for producing methylacetylene and propadiene in a reaction zone which is elongate in one direction (one axis) comprises a heating zone and a cooling zone following said heating zone, in which a gas mixture comprising at least one hydrocarbon containing at least three carbon atoms e.g. propane and/or propylene from stream cracking, and at least one diluent is circulated in the heating zone, under super-atmospheric pressure, in a flow direction substantially parallel to the direction (to the axis) of the heating zone, wherein the heating zone comprises at least one preheating zone in which the temperature of said gas mixture increases by about 50° C. to 120° C. per {fraction (1/10)} of the length of the heating zone, at least one pyrolysis zone for the feed in which the temperature rises by about 20° C. to 50° C. per {fraction (1/10)} of the length of the heating zone and at least one methylacetylene-propadiene formation zone in which the temperature climbs by about 70° C.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: December 25, 2001
    Assignee: Institut Francais du Petrole
    Inventor: Christian Busson
  • Patent number: 6323383
    Abstract: A process for the synthesis of chemical industrial feedstock and high-octane fuel, wherein calcium phosphate which is controlled in the molar Ca/P ratio and/or one which contains an activating metal (M) at a molar (Ca+M)/P ratio of 1 to 2 is used as the catalyst and ethanol is used as the feedstock.
    Type: Grant
    Filed: September 27, 2000
    Date of Patent: November 27, 2001
    Assignee: Kabushiki Kaisha Sangi
    Inventors: Takashi Tsuchida, Kiminori Atsumi, Shuji Sakuma, Tomoyuki Inui
  • Patent number: 5866737
    Abstract: A process for the oxidation and oxidative dehydrogenation of hydrocarbons, in particular ethylbenzene, to form corresponding oxidized or olefinically unsaturated compounds, in particular styrene, over an oxygen-conferring, oxygen-regenerable catalyst involving a working period, a time-displaced regenerating period and at least one intermediate rinsing period comprises effecting a partial regeneration during the working period by time-displaced addition of a substoichiometric amount of oxygen.
    Type: Grant
    Filed: January 7, 1997
    Date of Patent: February 2, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Hagemeyer, Jurgen Schweinzer, Otto Watzenberger
  • Patent number: 5859277
    Abstract: A compound of the formula ##STR1## where R is a solid support; R.sub.1 and R.sub.2 are alkyl, unsubstituted alkyl, or phenyl, and where R.sub.1 and R.sub.2 can be the same or different, for use in solid-phase synthesis.
    Type: Grant
    Filed: June 25, 1997
    Date of Patent: January 12, 1999
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Howard W. Whitlock, Karin Kay Maxson
  • Patent number: 5801293
    Abstract: The invention includes a method for skeletal isomerization of C.sub.4-5 olefins. The method includes contacting in a FCC zone, at FCC conditions, an n-C.sub.4-5 olefins-containing etherification zone raffinate, with an FCC catalyst, where at least a portion of the n-C.sub.4-5 olefins in the n-C.sub.4-5 olefins-containing etherification zone raffinate are converted to iso-C.sub.4-5 olefins.
    Type: Grant
    Filed: January 10, 1997
    Date of Patent: September 1, 1998
    Assignee: Chevron U.S.A. Inc.
    Inventor: Stephen J. Miller
  • Patent number: 5792891
    Abstract: An alkene skeletal isomerization process is employed in an integrated process for the production of tertiary ether, e.g., tertiary amyl methyl ether (TAME) from the reaction of isoamylenes (iC.sub.5.sup.= 's) with methanol in the presence of an acid cation exchange resin. A light naphtha from a fluid catalytic cracking unit is used as the source of the iC.sub.5.sup.= 's in a process which separates the C.sub.5 containing fraction from the light naphtha, selectively hydrogenates the di-olefins contained in the C.sub.5 containing fraction, reacts the iC.sub.5.sup.= 's contained in the C.sub.5 containing fraction with methanol to form TAME, separates the TAME from the unreacted materials as a product, separates methanol from the unreacted materials, isomerizes a portion of the nC.sub.5.sup.= 's to iC.sub.5.sup.= 's , for example using a zeolite or an alumina treated with methanol, and use of the isomerization product as feed for a TAME reactor.
    Type: Grant
    Filed: February 3, 1997
    Date of Patent: August 11, 1998
    Assignee: Catalytic Distillation Technologies
    Inventors: John R. Adams, Lawrence A. Smith, Jr., Dennis Hearn, Edward M. Jones, Jr., Robert P. Arganbright
  • 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: 5698752
    Abstract: A selective hydrogenation of an alkyne in an olefin-containing fluid is provided which comprises contacting the fluid and hydrogen gas with a catalyst in the presence of at least one sulfur compound, under reaction conditions effective to produce at least one alkene wherein the catalyst comprises at least one alkali metal, fluorine and an inorganic support material.
    Type: Grant
    Filed: July 23, 1996
    Date of Patent: December 16, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Scott H. Brown, James B. Kimble, Stan A. Zisman
  • Patent number: 5672803
    Abstract: A method is provided for selectively producing a trans-geometrical isomer of non-conjugated diolefins. The method comprises treating a starting non-conjugated diolefin isomer or mixture of isomers, a first mono-olefin and a second mono-olefin with a metathesis catalyst under selected reaction conditions to produce a product with greater than 80% trans-geometrical isomer content. In a preferred embodiment, 1,4-hexadiene, ethene, and propene contact a Re.sub.2 O.sub.7 catalyst and are converted to a reaction product mixture with above 80% trans-1,4-hexadiene.
    Type: Grant
    Filed: November 27, 1995
    Date of Patent: September 30, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Robert Scott Smith, Jos Peter Wristers
  • Patent number: 5659101
    Abstract: A catalytic system to polymerize diolefinic monomers consists of a lanthanide salt, an organometallic compound of a metal belonging to groups I, II and III of the periodic table of elements and an organometallic compound of boron. The polymers obtained are characterized in that they have a high degree of 1,4 chain units and ratio between 1.4-cis/1,4-trans units which can vary as desired, and also a narrow molecular weight distribution.
    Type: Grant
    Filed: August 17, 1995
    Date of Patent: August 19, 1997
    Assignees: Enichem Elastomeri S.r.l., Eniricerche S.p.A.
    Inventors: Paolo Biagini, Gabriele Lugli, Fabio Garbassi, Piero Andreussi
  • Patent number: 5648583
    Abstract: Exo-isomers of polyalkylcyclopentadienes are converted to endo-isomers by contacting the exo-isomers with an acid such as aqueous HCl.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: July 15, 1997
    Assignee: Albemarle Corporation
    Inventors: John Y. Lee, Meng-Sheng Ao, Stephen E. Belmont, Lawrence H. Shepherd, Jr.
  • Patent number: 5510550
    Abstract: A catalyst composition comprising palladium, silver and a support material (preferably alumina) is contacted at a relatively low temperature (of up to about 60.degree. C.) with a liquid composition comprising an effective reducing agent (preferably an alkali metal borohydride, hydrazinc, formaldehyde, formic acid, ascorbic acid, dextrose, aluminum powder). Preferably, at least one alkali metal compound (more preferably KOH, RbOH, CsOH, KF) is also present in the liquid composition. An improved process for selectively hydrogenating acetylene (to ethylene) employs this wet-reduced catalyst composition.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: April 23, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Tin-Tack P. Cheung, Marvin M. Johnson, Scott H. Brown, Stan A. Zisman, James B. Kimble
  • Patent number: 5430213
    Abstract: Pure 1,4-dienes are produced at high rates of reaction by reacting a conjugated diene and an alpha monoolefin at a temperature below 70.degree. C. in the presence of a catalyst consisting essentially of a 1,3-bis(diphenylphosphino)propane ligand of Co(II)(acetylacetonate).sub.2 or Co(III)(acetylacetonate).sub.3 or CoCl.sub.2 in combination with a dialkylaluminum halide such as diethylaluminum chloride.
    Type: Grant
    Filed: May 6, 1993
    Date of Patent: July 4, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Dan E. Hendriksen, Stephanie Linscott
  • Patent number: 5416258
    Abstract: Methods and compositions are provided for inhibiting the polymerization of butadiene-containing streams during elevated temperature processing thereof or during storage or shipment of monomer containing product. The composition comprises a combination of (a) a phenylenediamine compound having at least one N--H bond and (b) a hydroxytoluene compound. The methods comprise adding from about 1-250 ppm of the combination to the monomer medium, per one million parts of medium.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: May 16, 1995
    Assignee: Betz Laboratories, Inc.
    Inventors: Graciela B. Arhancet, Paul V. Roling
  • Patent number: 5354937
    Abstract: Tert-amyl compounds of the general formula I ##STR1## and novel processes for preparing 2-tert-amylbutadiene by dehydrating 3,4,4-trimethylhex-1-en-3-ol at from 100.degree. to 350.degree. C. and from 0.01 to 50 bar on acidic catalysts, its preparation by partially hydrogenating 3,4,4-trimethyl-hex-1-yn-03-ol at from 0.degree. to 50.degree. C. and from 0.01 to 50 bar and its preparation by reacting tert-amyl methyl ketone (3,3-dimethylpentan-2-one) with acetylene in the presence of basic catalysts at from 0.degree. to 60.degree. C. and from 0.01 to 50 bar, and also the preparation of 2-tert-amylanthraquinone by reacting 2-tert-amylbutadiene with 1,4-naphthoquinone at from 20.degree. to 200.degree. C. and from 0.01 to 50 bar to give 2-tert-amyl-1,4,4a,9a-tetrahydroanthraquinone and then oxidizing the latter in the presence of a strong base at from 0.degree. to 50.degree. C. are described.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: October 11, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ebel, Juergen Schroeder
  • Patent number: 5304699
    Abstract: Disclosed is a process for removing hydrogenation by-products which comprises the use of an extractive distillation tower operated in combination with a solvent stripper, hydrocarbon purge and a water wash column. By the arrangement of the various feeds to and between the above mentioned, the green oil may be extracted away from desirable hydrocarbons.
    Type: Grant
    Filed: April 19, 1993
    Date of Patent: April 19, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Christopher D. W. Jenkins, Michel H. Masson, Richard A. Reitz
  • Patent number: 5245098
    Abstract: The monomer 5-methyl-1,4-hexadiene (5-MHD), uncontaminated with 4-methyl-1,4-hexadiene (4-MHD), or other hydrocarbons, is obtained by reacting 1-chloro-2-methylpropene with allylmagnesium bromide in equimolar amounts under gentle reflux at atmospheric pressure in an organic solvent medium (diethyl ether) and in the presence of a catalytic amount of a dichloro-[1,2-bis(dimethylphosphino)ethane]nickel (II) in an inert atmosphere. The allyl magnesium bromide is added dropwise with stirring with a mixture of 1-chloro-2-methylpropene and catalyst in the solvent at room temperature. The solvent is separated from the product by distillation, giving substantially pure product. Absence of other hydrocarbons in either the crude product or the pure product may be shown by .sup.1 H NMR, .sup.13 C NMR and GC analysis. Other nonconjugated diolefins can be prepared in an analogous manner using an alkenyl halide and an alkenyl Grignard reagent which upon cross coupling will give the desired nonconjugated diene.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: September 14, 1993
    Assignee: The University of Akron
    Inventors: Gabriel J. Summers, Fernando J. Hamilton
  • Patent number: 5238998
    Abstract: A toner composition comprised of multiblock or liquid glass resin particles with a glass transition temperature of between from about 20.degree. C. to about 65.degree. C., and pigment particles.
    Type: Grant
    Filed: October 5, 1992
    Date of Patent: August 24, 1993
    Assignee: Xerox Corporation
    Inventors: Timothy J. Fuller, Samuel Kaplan, Michael J. Levy, Joseph D. Geiser, Richard B. Lewis, William M. Prest, Jr.
  • Patent number: 5113032
    Abstract: Process for producing olefins from natural gas, the natural gas (2) is mainly fractionated (1) into methane (3) and higher hydrocarbons (4), the latter being then mainly fractionated (17, 20) into propane (9) and ethane (7). The methane (3), admixed with oxygen (6), passes through an oxidation reactor (5), receives the ethane (7) and the obtained mixture passes through a pyrolysis reactor (8). The effluent coming out of reactor (8) receives the propane (9) and the obtained mixture passes through a pyrolysis reactor (10). A hydrocarbon flow comprising olefins (12), more particularly ethylene and propene, is recovered.
    Type: Grant
    Filed: January 8, 1990
    Date of Patent: May 12, 1992
    Assignee: Institut Francais du Petrole
    Inventors: Charles Cameron, Hubert Mimoun, Alain Robine, Serge Bonnaudet, Patrick Chaumette, Quang Dang Vu
  • Patent number: 5113033
    Abstract: A catalyst system for codimerization of alpha-monoolefins and conjugated diolefins to yield 1,4-dienes. The catalyst system includes at least one ruthenium salt and at least one aluminum halide. Suitable aluminum halides include both alkyl aluminum halides and nonalkylated aluminum halides, as well as mixtures thereof.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: May 12, 1992
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Richard S. Myers, Daniel R. Mills, Robert C. Michaelson
  • Patent number: 5025111
    Abstract: Non-conjugated diolefins having the formula: ##STR1## wherein R.sup.3 and R.sup.4 are either hydrogen, alkyl or substituted alkyl and n is an integer,are produced by the process comprising reacting a diolefin having the formula: ##STR2## wherein R.sup.3 and R.sup.4 and n are the same as in formula (I) and R.sup.1 and R.sup.2 are either hydrogen, alkyl or substituted alkyl,with ethylene in the presence of a disproportionation catalyst comprising supported rhenium heptoxide and a promoter comprising either a tetraalkyl tin compound or a trialkyl aluminium compound.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: June 18, 1991
    Assignee: BP Chemicals Limited
    Inventor: Nicholas J. Hazel
  • Patent number: 5025108
    Abstract: Process for producing olefins from natural gas. The natural gas is fractionated (1). The methane (3) mixed with oxygen (6) crosses the oxidizing reactor (5), receives the C.sub.2 + hydrocarbons (7) and the mixture crosses the pyrolysis reactor (8). A hydrocarbons flow containing olefins (10) is collected.
    Type: Grant
    Filed: April 4, 1989
    Date of Patent: June 18, 1991
    Assignee: Institut Francais du Petrole
    Inventors: Charles Cameron, Hubert Mimoun, Alain Robine, Serge Bonnaudet, Patrick Chaumette, Quang Dang Vu
  • Patent number: 4996340
    Abstract: A novel migratory insertion reaction is disclosed utilizing organoaluminum compounds. An intramolecular transfer of a carbon group from the aluminum complex E-1-halo-1-alkenyl)trialkylalanate occurs to produce an E-alkenyl(alkoxy)dialkylalanate or an E-dialkylalkenylalane or an (E,E)-3-alkyl-2-dialkylalumino-1,3-diene depending on process conditions. Novel organic aluminates are also disclosed.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: February 26, 1991
    Assignee: Ethyl Corporation
    Inventor: Joseph A. Miller