By Double-bond Shift Patents (Class 585/377)
  • Publication number: 20150031927
    Abstract: A fuel and method for conversion of sesquiterpenes to high density fuels. The sesquiterpenes can be either extracted from plants or specifically produced by bioengineered organisms from waste biomass. This approach allows for the synthesis of high performance renewable fuels.
    Type: Application
    Filed: November 14, 2012
    Publication date: January 29, 2015
    Inventors: Benjamin G. Harvey, Heather A. Meylemans
  • Publication number: 20130324688
    Abstract: The preparation of cyclohexadienes from one or more plant oils is disclosed. The cyclohexadiene can be used to form polymers or derivatized to form other monomers that can be used to form polymeric materials.
    Type: Application
    Filed: April 9, 2013
    Publication date: December 5, 2013
    Inventor: Robert T. MATHERS
  • Patent number: 8049050
    Abstract: A method for synthesizing exo-tetrahydrodicyclopentadiene (exo-THDCPD) and adamantane is provided, including isomerization of an endo-tetrahydrodicyclopentadiene (endo-THDCPD) as a reaction feed with an acidic ionic liquid of aluminum trichloride in a pseudo-fixed bed ionic liquid reactor. Reactants float as a droplet from bottom to top of the pseudo-fixed bed reactor, and finally are discharged from a side tube. A mole fraction of aluminum trichloride in the acidic ionic liquid of aluminum trichloride is from 0.5 to 0.9, a feeding rate of the reaction feed is 0.1-10 g/min, and a temperature for the isomerization is between 25-120° C.
    Type: Grant
    Filed: May 11, 2009
    Date of Patent: November 1, 2011
    Assignee: CPC Corporation, Taiwan
    Inventors: Ming-Yu Huang, Jen-Chun Chang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
  • Patent number: 8017821
    Abstract: A process for isomerization of tetrahydrodicyclopentadiene using a supported acidic ionic liquid as catalyst is provided. In the presence of the supported acidic ionic liquid, endo-tetrahydrodicyclopentadiene is isomerized to exo-tetrahydrodicyclo-pentadiene, wherein the supported acidic ionic liquid includes a porous support and an acidic ionic liquid, and the acidic ionic liquid includes an aluminum halide, and a quaternary ammonium halide or a quaternary phosphonium halide. The porous support is impregnated with the acidic ionic liquid. Furthermore, under different reaction conditions, the exo-tetrahydrodicyclopentadiene product can be isomerized to adamantane in the presence of such a supported acidic ionic liquid.
    Type: Grant
    Filed: March 24, 2009
    Date of Patent: September 13, 2011
    Assignee: CPC Corporation, Taiwan
    Inventors: Ming-Yu Huang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
  • Patent number: 7488860
    Abstract: An exo-tetrahydrodicyclopentadiene is produced from endo-tetrahydrodicyclopentadiene through isomerization reaction. An acidic ionic liquid is used in the isomerization. The isomerization of endo-tetrahydrodicyclopentadiene gives a reaction conversion and a selectivity both higher than 99%. Besides, the ionic liquid used is environmental-friendly and recyclable.
    Type: Grant
    Filed: September 13, 2006
    Date of Patent: February 10, 2009
    Assignee: Chinese Petroleum Corp.
    Inventors: Ming-Yu Huang, Jen-Chun Chang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
  • Publication number: 20080064909
    Abstract: An exo-tetrahydrodicyclopentadiene is produced from endo-tetrahydrodicyclopentadiene through isomerization reaction. An acidic ionic liquid is used in the isomerization. The isomerization of endo-tetrahydrodicyclopentadiene gives a reaction conversion and a selectivity both higher than 99%. Besides, the ionic liquid used is environmental-friendly and recyclable.
    Type: Application
    Filed: September 13, 2006
    Publication date: March 13, 2008
    Applicant: CHINESE PETROLEUM CORP.
    Inventors: Ming-Yu Huang, Jen-Chun Chang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
  • Patent number: 7329788
    Abstract: Process for producing gasoline components. The process comprises feeding a fresh olefinic hydrocarbon feedstock to a reaction zone, in which its structure is first isomerized. The isomerized hydrocarbon is drawn out of the first reaction zone and conducted to a second reaction zone, where the isomerized hydrocarbon is dimerized. The dimerized reaction product is drawn out of the second reaction zone and separated from the flow in a separation zone. Because there are more isoolefins present in the dimerization unit feed, more isoolefin dimers useful as fuel components can be produced.
    Type: Grant
    Filed: December 22, 2003
    Date of Patent: February 12, 2008
    Assignee: Neste Oil Oyj
    Inventors: Marja Tiitta, Elina Harlin, Antti Pyhälahti
  • Patent number: 7151199
    Abstract: Hydrocarbon or oxygenate conversion process in which a feedstock is contacted with a non zeolitic molecular sieve which has been treated to remove most, if not all, of the halogen contained in the catalyst. The halogen may be removed by one of several methods. One method includes heating the catalyst in a low moisture environment, followed by contacting the heated catalyst with air and/or steam. Another method includes steam-treating the catalyst at a temperature from 400° C. to 1000° C. The hydrocarbon or oxygenate conversion processes include the conversion of oxygenates to olefins, the conversion of oxygenates and ammonia to alkylamines, the conversion of oxygenates and aromatic compounds to alkylated aromatic compounds, cracking and dewaxing.
    Type: Grant
    Filed: June 10, 2002
    Date of Patent: December 19, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Luc Roger Marc Martens, Stephen N. Vaughn, Albert Edward Schweizer, John K. Pierce, Shun Chong Fung
  • Patent number: 7132582
    Abstract: The present invention relates to a catalytic process for preparation of isolongifolene using nanocrystalline solid super acid. This process is an eco-friendly, single step, solvent free catalytic process for the preparation of a tricyclic sesqui-terpene hydrocarbon, isolongifolene. More particularly, the present invention provides a process for the catalytic isomerisation of longifolene to iso-longifolene using nano-crystalline sulfated zirconia as a solid super acid catalyst.
    Type: Grant
    Filed: May 30, 2003
    Date of Patent: November 7, 2006
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raksh Vir Jasra, Beena Tyagi, Manish Kumar Mishra
  • Patent number: 6559323
    Abstract: A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I), wherein X is oxygen, NR4 or CHR5; R1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R2 is hydrogen, alkyl, aryl, heteroaromatic, CO2R8, CHR14NHR13, heterocyclic or cycloalkyl; or R1 and R2 join together to form a cycloalkyl ring; R3 and R10 are, independently, hydrogen, alkyl, aryl, heteroaromatic, CO2R8, R83Sn, CONR8R9, trialkylsilyl or triarylsilyl; R4 is an electron withdrawing group; R5 is alkyl, cycloalkyl, aryl, heteroaromatic, SO2R8, SO3R8, COR8, CO2R8, CONR8R9, PO(R8)2, PO(OR8)2 or CN; R8 and R9 are independently alkyl or aryl; and R13 and R14 are independently hydrogen, alkyl or aryl is provided. The process comprises degrading a compound of formula (II), (IIa), (IIb) or (IIc): wherein R3 and R10 are as defined above; Y is a cation; depending on the nature of Y, r is 1 or 2; and L is a suitable leaving group, to form a diazo compound.
    Type: Grant
    Filed: February 28, 2000
    Date of Patent: May 6, 2003
    Assignees: Avecia Limited, University of Sheffield
    Inventors: John Richard Studley, Varinder Kumar Aggarwal
  • Publication number: 20010053835
    Abstract: A supported Lewis acid catalyst system effective for hydrocarbon conversion reactions including cationic polymerization, alkylation, isomerization and cracking reactions and comprising at least one Lewis acid immobilized on an anhydrous dihalide of Cd, Fe, Co, Ni, Mn or Mg is disclosed.
    Type: Application
    Filed: December 19, 2000
    Publication date: December 20, 2001
    Applicant: Exxon Chemical Patents Inc.
    Inventors: Frank Joung-yei Chen, Christophe Le Deore, Roger Spitz, Alain Louis Pierre Lenack
  • Patent number: 6294707
    Abstract: The present invention is directed to a continuous process for producing a desired hydrocarbon product using a heterogeneous slurry catalyst, to the product of said process, and to the reactor utilized in such process.
    Type: Grant
    Filed: August 29, 1997
    Date of Patent: September 25, 2001
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Christopher Lynn Becker, James Richardson Lattner, Mark T. Swihart
  • Patent number: 6077492
    Abstract: A titanium oxide photocatalyst having metal ions of one or more metals incorporated therein selected from the group consisting of Cr, V, Cu, Fe, Mg, Ag, Pd, Ni, Mn and Pt, wherein the metal ions are implanted from the surface to deep inside of the bulk of the photocatalyst in an amount of at least 1.times.10.sup.15 ions per g of the titanium oxide; a process for producing the photocatalyst; and a photocatalytic reaction method using the photocatalyst.
    Type: Grant
    Filed: August 21, 1997
    Date of Patent: June 20, 2000
    Assignee: Petroleum Energy Center
    Inventors: Masakazu Anpo, Hiromi Yamashita, Sakunobu Kanai, Kazuhito Sato, Takanori Fujimoto
  • 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: 5446222
    Abstract: The invention provides a two-step process for converting cyclopentadiene dimer to a high density fuel mixture comprising the steps of:(a) reacting said cyclopentadiene dimer in the presence of a solid catalyst comprising a porous crystalline material having a Constraint Index of from about 0.1 to about 12 under oligomerization/isomerization conditions to convert at least a portion of said cyclopentadiene dimer to a normally liquid intermediate product containing cyclopentadiene trimer, cyclopentadiene tetramer, and the isomerized and oligomerized products derived from the reaction of at least three cyclopentadiene monomer units;(b) hydrogenating said normally liquid intermediate product of step (a) in the presence of a hydrogenation catalyst to form a normally liquid high energy density fuel.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: August 29, 1995
    Assignee: Mobil Oil Corporation
    Inventors: James R. Boulton, Ross A. Kremer
  • Patent number: 5011990
    Abstract: Compounds having the formula ##STR1## wherein R is an aromatic or aliphatic group; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen, C.sub.1-4 alkyl or phenyl; X is halogen; and Y is halogen or an aromatic group; are prepared in a regioselective manner by treating a compound having the formula ##STR2## with a catalytic amount of a palladium(O) or a palladium(II) transition metal catalyst.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: April 30, 1991
    Inventor: Raymond A. Felix
  • Patent number: 4727204
    Abstract: 5-Ethylidene-2-norbornene with high quality is effectively prepared by isomerization 5-vinyl-2-norbornene containing 1 ppm to 0.5% by weight of 4-vinylcyclohexene in the presence of at least one catalyst selected from the group consisting of a solid base catalyst which is prepared by reacting alumina, an alkali metal hydroxide and an alkali metal in a temperature range of 200.degree. to 500.degree. C. and a solid base catalyst which is prepared by reacting water-containing alumina and an alkali metal in such an amount that exceeds a molar equivalent of water contained in alumina at a temperature in a range between a melting point of the alkali metal and 500.degree. C. in an inert gas atmosphere.
    Type: Grant
    Filed: December 18, 1986
    Date of Patent: February 23, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Gohfu Suzukamo, Masami Fukao, Fujio Masuko, Masahiro Usui, Kazuo Kimura
  • Patent number: 4720601
    Abstract: 5-Ethylidene-2-norbornene is effectively prepared by isomerization 5-vinyl-2-norbornene in the presence of at least one catalyst selected from a group consisting of a solid base catalyst which is prepared by reacting alumina and an alkali metal hydroxide at a temperature of 200.degree. to 500.degree. C. and then reacting the reaction produce with an alkali metal at a temperature of 180.degree. to 350.degree. C. and a solid base catalyst which is prepared by reacting water-containing alumina and an alkali metal in such an amount that corresponds to a molar equivalent of water contained in alumina at a temperature in a range between a melting point of the alkali metal and 500.degree. C. and then reacting the reaction product with an alkali metal at a temperature of 180.degree. to 350.degree. C.
    Type: Grant
    Filed: August 15, 1986
    Date of Patent: January 19, 1988
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Gohfu Suzukamo, Masami Fukao
  • Patent number: 4625069
    Abstract: Coordination compounds of rhodium are solid salts having donor ligands of [(aryl).sub.3 P].sub.3 Rh.sup.+ and a non-coordinated counterion derived from a fluorochemical acid, the salts having the formula:[(aryl).sub.3 P].sub.3 Rh.sup.+ (counterion).sup.-.The salts are prepared by reacting [(aryl).sub.3 P].sub.4 RhH, which is and uncharged rhodium hydride, with a fluorochemical acid selected form acids having the formulae:HC(R)(SO.sub.2 R.sub.f).sub.2, R.sub.f 'SO.sub.3 H, and HN(SO.sub.2 R.sub.f).sub.2wherein R.sub.f and R.sub.f ' are perfluoroalkyl groups and R is lower alkyl substituted or unsubstituted phenyl, hydrogen, Cl, SO.sub.2 R.sub.f or R.sub.f. Carbonylation of the [(aryl).sub.3 P].sub.3 Rh.sup.+ (counterion).sup.- compounds of this invention, e.g., by contacting the salts of the invention with carbon monoxide gas, produces salts having the formula:[(aryl).sub.3 P].sub.3 Rh(CO).sub.n.sup.+(counterion).sup.-,wherein n is 1 or 2, and (counterion).sup.- is as defined above.
    Type: Grant
    Filed: August 26, 1985
    Date of Patent: November 25, 1986
    Assignee: Minnesota Mining and Manufacturing
    Inventors: Allen R. Siedle, Richard D. Howells
  • Patent number: 4551570
    Abstract: A process for isomerizing limonene to terpinolene in the presence of an acidic catalyst and in the presence of a buffer.
    Type: Grant
    Filed: January 14, 1985
    Date of Patent: November 5, 1985
    Assignee: SCM Corporation
    Inventor: Walter E. Johnson, Jr.
  • Patent number: 4544780
    Abstract: A process for the isomerization of a tertiary double bonded olefin having a hydrogen atom attached to a carbon atom vicinal to the tertiary carbon of the double bond comprises treating the olefin in a solution of dry liquid sulfur dioxide in the presence of a catalyst selected from oxygen, a hydroperoxide or a protic acid or mixtures thereof.
    Type: Grant
    Filed: April 27, 1984
    Date of Patent: October 1, 1985
    Assignee: Shell Oil Company
    Inventor: Stanley E. Wilson
  • Patent number: 4533651
    Abstract: Catalyst systems for the oligomerization and/or isomerization of olefins which comprise a nickel (II) complex and a co-catalyst. The nickel (II) complex is a square planar species with a trivalent Group V donor ligand, preferably a phosphine or phosphite ligand, a halogen or pseudo-halogen ligand and a bidentate dithio ligand, especially a substituted dithio-.beta.-diketone ligand.
    Type: Grant
    Filed: October 17, 1983
    Date of Patent: August 6, 1985
    Assignee: Commonwealth Scientific and Industrial Research Organization
    Inventors: Anthony F. Masters, Kingsley J. Cavell
  • Patent number: 4508930
    Abstract: There is disclosed a process for the conversion of terpenes to limonene which comprises contacting at least one terpene, selected from the group comprised of mono- and bi-cyclic unsaturated hydrocarbons having the formula C.sub.10 H.sub.16 with an alkali metal sulfide catalyst on a support at a temperature of 300.degree. to 450.degree. C.
    Type: Grant
    Filed: July 20, 1984
    Date of Patent: April 2, 1985
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Lawson G. Wideman, Lynn A. Bente
  • Patent number: 4434310
    Abstract: A process for the isomerization of isolated double bonds to conjugated double bonds in optionally substituted cyclooctadienes using alkali metal or alkaline earth metal amides, if desired in the presence of a solvent, requires that the alkali metal or alkaline earth metal amide be produced with exclusion of moisture and under a protective gas atmosphere in the presence of the cyclooctadiene to be isomerized; and that the isomerization be conducted at temperatures of 70.degree.-200.degree. C.
    Type: Grant
    Filed: January 13, 1983
    Date of Patent: February 28, 1984
    Assignee: Chemische Werke Huels Aktiengesellschaft
    Inventor: Wolfgang Kampf
  • Patent number: 4260842
    Abstract: It has been found that catalysts comprising zirconium hydrides, hydride alkyls and dihydrides bonded to metal or metalloid oxides in particular zirconium hydride bonded to silica, when contacted with olefins under mild conditions rapidly cause isomerization to thermodynamic mixtures.
    Type: Grant
    Filed: November 7, 1979
    Date of Patent: April 7, 1981
    Assignee: The Trustees of Princeton University
    Inventors: Jeffrey Schwartz, Michael D. Ward
  • Patent number: 4228035
    Abstract: Novel polymer supported catalysts are prepared by irradiation of low valent transition metal compounds such as iron carbonyl in the presence of solid polymers containing ligands such as phosphinated polystyrene. Hydrogenation of olefins at ambient conditions has been demonstrated.
    Type: Grant
    Filed: May 3, 1976
    Date of Patent: October 14, 1980
    Assignee: California Institute of Technology
    Inventors: Harry B. Gray, Claude C. Frazier
  • Patent number: 4227028
    Abstract: A process for regioselective isomerization of organic compounds having a carbon-carbon double bond at a tertiary carbon atom by sulfur dioxide induced allylic rearrangement of a hydrogen atom and/or replacement of a proton in the allylic position by a deuteron. The organic compound is contacted with sulfur dioxide at temperatures between about 0.degree. and 70.degree. C. for a time sufficient to effect such isomerization to a more stable isomer; and if deuteration is to take place D.sub.2 O is provided in the solution.
    Type: Grant
    Filed: March 1, 1979
    Date of Patent: October 7, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Divakaran Masilamani, Milorad M. Rogic
  • Patent number: 4202996
    Abstract: Isomerizable hydrocarbons including paraffins, cycloparaffins, olefins and alkyl aromatics are isomerized by contacting the hydrocarbon at isomerization conditions with a catalytic composite comprising a combination of a nickel component, a molybdenum component and a platinum component with a zeolitic carrier material wherein said platinum component is present in an amount sufficient to result in the composite containing, on an elemental basis, about 0.2 to about 0.5 percent by weight platinum.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: May 13, 1980
    Assignee: UOP Inc.
    Inventor: Lee Hilfman
  • Patent number: 4190612
    Abstract: Beta pinene is converted to alpha pinene in liquid sulfur dioxide. The process is a regioselective isomerization of organic compounds having a carbon-carbon double bond at a tertiary carbon atom, by sulfur dioxide-induced allylic rearrangement of a hydrogen atom and/or replacement of a proton in the allylic position by a deuteron. The organic compound is contacted with sulfur dioxide at temperatures between about 0.degree. and 70.degree. C. for a time sufficient to effect such isomerization to a more stable isomer; and if deuteration is to take place D.sub.2 O is provided in the solution.
    Type: Grant
    Filed: December 20, 1977
    Date of Patent: February 26, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Divakaran Masilamani, Milorad M. Rogic
  • Patent number: 4180524
    Abstract: Double bond isomerization and disproportionation of olefins is obtained by contact with a catalyst in a single-stage composition containing a support, uranium, and at least one of tungsten, molybdenum, or rhenium.
    Type: Grant
    Filed: February 16, 1978
    Date of Patent: December 25, 1979
    Assignee: Phillips Petroleum Company
    Inventors: Robert E. Reusser, William B. Hughes