By Double-bond Shift In Side-chain Patents (Class 585/363)
  • Patent number: 8704022
    Abstract: Embodiments of the present invention are directed generally to methods for producing high purity exo-alkenylnorbornenes from a mixture of conformational isomers thereof.
    Type: Grant
    Filed: August 6, 2008
    Date of Patent: April 22, 2014
    Assignee: Promerus, LLC
    Inventors: Andrew Bell, Dane Jablonski, Elaine Koronich, Brian Knapp, Dino Amoroso
  • 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
  • Publication number: 20090054714
    Abstract: Embodiments of the present invention are directed generally to methods for producing high purity exo-alkenylnorbornenes from a mixture of conformational isomers thereof.
    Type: Application
    Filed: August 6, 2008
    Publication date: February 26, 2009
    Applicant: PROMERUS LLC
    Inventors: Andrew Bell, Dane Jablonski, Elaine Koronich, Brian Knapp, Dino Amoroso
  • 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: 20040049090
    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: Application
    Filed: August 11, 2003
    Publication date: March 11, 2004
    Inventors: Christopher Lynn Becker, James Richardson Lattner, Mark T. Swihart
  • 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: 5849966
    Abstract: A process and catalyst for isomerizing olefins are disclosed. The process and catalyst are particularly useful for isomerizing alkenyl bridged ring compounds to the corresponding alkyladiene bridged ring compounds. In one embodiment, the isomerization catalyst comprises an oxygen treated mixture of an alkali metal on a dried support having a surface area of 125 to 195 m.sup.2 /g when the support consists essentially of alumina wherein the alumina precursor is a large crystallite pseudoboehmite. The catalyst is particularly useful for isomerizing 5-vinyl-2-norbornene to 5-ethylidiene-2-norbornene. The catalyst is very active and highly selective and resistant to catalyst poisons. The process contacts the catalyst with an alkenyl bridged ring compound and yields the corresponding alkyladiene bridged ring compound.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 15, 1998
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Robert Scott Smith, Christopher Lynn Becker
  • Patent number: 4891460
    Abstract: The present invention provides a process for producing alkylidenenorbornenes by reacting C.sub.4 -C.sub.6 acyclic conjugated dienes with cyclopentadiene, dicyclopentadiene, or a methyl- or dimethyl-substituted derivative thereof in the presence of a catalyst derivative composed of:(A) a titanium-containing compound, and(B) at least one metallic reducing agent containing the group IA, IIA or IIIA metals in the periodic table.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: January 2, 1990
    Assignee: San-Petrochemicals Co., Ltd.
    Inventor: Yasutaka Ishii
  • Patent number: 4861931
    Abstract: A process for producing a 5-alkylidenenorbornene, which comprises contacting a 5-alkenylnorbornene with an organolithium compound and at least one compound selected from the group consisting of ammonia, a hydrazine compound and an aliphatic amine compound wherein at least one nitrogen atom in the molecule bonds to at least one hydrogen atom to isomerize the 5-alkenylnorbornene. This process enables the easy and efficient production of a 5-alkylidenenorbornene from an easily available raw material.
    Type: Grant
    Filed: June 20, 1988
    Date of Patent: August 29, 1989
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Yasuo Hara, Ryuji Oashi, Yoshitaka Kawahara, Mikio Takeuchi
  • 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: 4289917
    Abstract: Alkali metal oxides of cis- and trans-2,6,6-trimethylbicyclo(3.1.1)-heptan-2-ol are surprisingly effective bases in organic reactions calling for the use of a strong base, especially those reactions wherein abstraction of a proton from attachment to a carbon atom is postulated to occur in the mechanism.
    Type: Grant
    Filed: August 17, 1979
    Date of Patent: September 15, 1981
    Assignee: SCM Corporation
    Inventors: Bernard J. Kane, Sean G. Traynor
  • Patent number: 4205192
    Abstract: A process for producing a 5-alkylidenenorbornene, which comprises subjecting a 5-alkenylnorbornene to catalytic reaction in the presence of ammonia and at least one alkali metal hydride selected from the group consisting of lithium, sodium and potassium hydrides. By using said alkali metal hydride supported on a carrier, the above-noted isomerization can be efficiently carried out with a relatively small amount of the catalyst.
    Type: Grant
    Filed: September 25, 1978
    Date of Patent: May 27, 1980
    Assignee: Japan Synthetic Rubber Company, Limited
    Inventor: Tetsuya Harada