By Double-bond Shift Patents (Class 585/377)
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Publication number: 20150031927Abstract: 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: ApplicationFiled: November 14, 2012Publication date: January 29, 2015Inventors: Benjamin G. Harvey, Heather A. Meylemans
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Publication number: 20130324688Abstract: 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: ApplicationFiled: April 9, 2013Publication date: December 5, 2013Inventor: Robert T. MATHERS
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Patent number: 8049050Abstract: 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: GrantFiled: May 11, 2009Date of Patent: November 1, 2011Assignee: CPC Corporation, TaiwanInventors: Ming-Yu Huang, Jen-Chun Chang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
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Patent number: 8017821Abstract: 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: GrantFiled: March 24, 2009Date of Patent: September 13, 2011Assignee: CPC Corporation, TaiwanInventors: Ming-Yu Huang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
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Patent number: 7488860Abstract: 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: GrantFiled: September 13, 2006Date of Patent: February 10, 2009Assignee: Chinese Petroleum Corp.Inventors: Ming-Yu Huang, Jen-Chun Chang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
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Publication number: 20080064909Abstract: 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: ApplicationFiled: September 13, 2006Publication date: March 13, 2008Applicant: CHINESE PETROLEUM CORP.Inventors: Ming-Yu Huang, Jen-Chun Chang, Jann-Chen Lin, Kun-Hai Lin, Jung-Chung Wu
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Patent number: 7329788Abstract: 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: GrantFiled: December 22, 2003Date of Patent: February 12, 2008Assignee: Neste Oil OyjInventors: Marja Tiitta, Elina Harlin, Antti Pyhälahti
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Patent number: 7151199Abstract: 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: GrantFiled: June 10, 2002Date of Patent: December 19, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Luc Roger Marc Martens, Stephen N. Vaughn, Albert Edward Schweizer, John K. Pierce, Shun Chong Fung
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Patent number: 7132582Abstract: 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: GrantFiled: May 30, 2003Date of Patent: November 7, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Raksh Vir Jasra, Beena Tyagi, Manish Kumar Mishra
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Patent number: 6559323Abstract: 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: GrantFiled: February 28, 2000Date of Patent: May 6, 2003Assignees: Avecia Limited, University of SheffieldInventors: John Richard Studley, Varinder Kumar Aggarwal
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Publication number: 20010053835Abstract: 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: ApplicationFiled: December 19, 2000Publication date: December 20, 2001Applicant: Exxon Chemical Patents Inc.Inventors: Frank Joung-yei Chen, Christophe Le Deore, Roger Spitz, Alain Louis Pierre Lenack
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Patent number: 6294707Abstract: 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: GrantFiled: August 29, 1997Date of Patent: September 25, 2001Assignee: ExxonMobil Chemical Patents Inc.Inventors: Christopher Lynn Becker, James Richardson Lattner, Mark T. Swihart
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Patent number: 6077492Abstract: 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: GrantFiled: August 21, 1997Date of Patent: June 20, 2000Assignee: Petroleum Energy CenterInventors: Masakazu Anpo, Hiromi Yamashita, Sakunobu Kanai, Kazuhito Sato, Takanori Fujimoto
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Patent number: 5648583Abstract: Exo-isomers of polyalkylcyclopentadienes are converted to endo-isomers by contacting the exo-isomers with an acid such as aqueous HCl.Type: GrantFiled: April 27, 1995Date of Patent: July 15, 1997Assignee: Albemarle CorporationInventors: John Y. Lee, Meng-Sheng Ao, Stephen E. Belmont, Lawrence H. Shepherd, Jr.
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Patent number: 5446222Abstract: 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: GrantFiled: June 17, 1994Date of Patent: August 29, 1995Assignee: Mobil Oil CorporationInventors: James R. Boulton, Ross A. Kremer
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Patent number: 5011990Abstract: 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: GrantFiled: December 27, 1988Date of Patent: April 30, 1991Inventor: Raymond A. Felix
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Patent number: 4727204Abstract: 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: GrantFiled: December 18, 1986Date of Patent: February 23, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Gohfu Suzukamo, Masami Fukao, Fujio Masuko, Masahiro Usui, Kazuo Kimura
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Patent number: 4720601Abstract: 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: GrantFiled: August 15, 1986Date of Patent: January 19, 1988Assignee: Sumitomo Chemical Company LimitedInventors: Gohfu Suzukamo, Masami Fukao
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Patent number: 4625069Abstract: 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: GrantFiled: August 26, 1985Date of Patent: November 25, 1986Assignee: Minnesota Mining and ManufacturingInventors: Allen R. Siedle, Richard D. Howells
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Patent number: 4551570Abstract: A process for isomerizing limonene to terpinolene in the presence of an acidic catalyst and in the presence of a buffer.Type: GrantFiled: January 14, 1985Date of Patent: November 5, 1985Assignee: SCM CorporationInventor: Walter E. Johnson, Jr.
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Patent number: 4544780Abstract: 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: GrantFiled: April 27, 1984Date of Patent: October 1, 1985Assignee: Shell Oil CompanyInventor: Stanley E. Wilson
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Patent number: 4533651Abstract: 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: GrantFiled: October 17, 1983Date of Patent: August 6, 1985Assignee: Commonwealth Scientific and Industrial Research OrganizationInventors: Anthony F. Masters, Kingsley J. Cavell
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Patent number: 4508930Abstract: 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: GrantFiled: July 20, 1984Date of Patent: April 2, 1985Assignee: The Goodyear Tire & Rubber CompanyInventors: Lawson G. Wideman, Lynn A. Bente
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Patent number: 4434310Abstract: 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: GrantFiled: January 13, 1983Date of Patent: February 28, 1984Assignee: Chemische Werke Huels AktiengesellschaftInventor: Wolfgang Kampf
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Patent number: 4260842Abstract: 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: GrantFiled: November 7, 1979Date of Patent: April 7, 1981Assignee: The Trustees of Princeton UniversityInventors: Jeffrey Schwartz, Michael D. Ward
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Patent number: 4228035Abstract: 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: GrantFiled: May 3, 1976Date of Patent: October 14, 1980Assignee: California Institute of TechnologyInventors: Harry B. Gray, Claude C. Frazier
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Patent number: 4227028Abstract: 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: GrantFiled: March 1, 1979Date of Patent: October 7, 1980Assignee: Allied Chemical CorporationInventors: Divakaran Masilamani, Milorad M. Rogic
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Patent number: 4202996Abstract: 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: GrantFiled: December 26, 1978Date of Patent: May 13, 1980Assignee: UOP Inc.Inventor: Lee Hilfman
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Patent number: 4190612Abstract: 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: GrantFiled: December 20, 1977Date of Patent: February 26, 1980Assignee: Allied Chemical CorporationInventors: Divakaran Masilamani, Milorad M. Rogic
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Patent number: 4180524Abstract: 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: GrantFiled: February 16, 1978Date of Patent: December 25, 1979Assignee: Phillips Petroleum CompanyInventors: Robert E. Reusser, William B. Hughes