Polycyclic Patents (Class 585/320)
  • Patent number: 7323610
    Abstract: A process for synthesizing a naphthacene compound comprises the steps of: (a) reacting a propargyl alcohol compound with a reagent capable of forming a leaving group to form a reaction mixture containing an intermediate; and then (b) heating the intermediate in the presence of a solvent and in the absence of any oxidizing agent and in the absence of any base, to form the naphthacene compound.
    Type: Grant
    Filed: July 27, 2004
    Date of Patent: January 29, 2008
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Manju Rajeswaran, Natasha Andrievsky
  • Patent number: 7019186
    Abstract: A highly selective process is described for preparing 2,6-dimethylnaphthalene which comprises reacting a naphthalene hydrocarbon selected from naphthalene, methylnaphthalenes, dimethylnaphthalenes, trimethylnaphthalenes, polymethylnaphthalenes, and/or their mixtures with one or more benzene hydrocarbons selected from benzene, toluene, xylenes, trimethylbenzenes, tetramethylbenzenes, pentamethylbenzene and/or hexamethylbenzene, under at least partially liquid phase conditions and in the presence of a catalytic composition comprising a zeolite belonging to the MTW structural type and at least one element selected from P, B and Si. The process is preferably carried out in the presence of a methylating agent.
    Type: Grant
    Filed: February 4, 2003
    Date of Patent: March 28, 2006
    Assignees: Enichem S.p.A., ENI S.p.A., Enitecnologie S.p.A.
    Inventors: Giannino Pazzuconi, Carlo Perego, Giuseppe Bellussi
  • Publication number: 20020119391
    Abstract: Disclosed are polymers containing as polymerized units one or more cyclic olefin monomers having fused cyclic electron withdrawing groups, methods of preparing such polymers, photoresist compositions including such polymers as resin binders and methods of forming relief images using such photoresist compositions.
    Type: Application
    Filed: February 23, 2001
    Publication date: August 29, 2002
    Applicant: Shipley Company, L.L.C.
    Inventors: George G. Barclay, Anthony Zampini
  • Patent number: 6380450
    Abstract: Tetrahydroindene is dehydrogenated in a vapor phase in the presence of a metallic catalyst, e.g., a nickel-molybdenum catalyst, to produce indene, which is industrially useful in high yield while inhibiting the catalyst from suffering a decrease in activity. In particular, a higher yield can be attained by a method in which tetrahydroindene is dehydrogenated to first convert it into indane, which is further dehydrogenated to obtain indene.
    Type: Grant
    Filed: April 15, 2000
    Date of Patent: April 30, 2002
    Assignee: Nippon Petrochemicals Company, Limited
    Inventor: Yasuo Matsumura
  • Patent number: 6350930
    Abstract: A method for producing an aromatic compound styrenic compound adduct comprising the steps of: (1) reacting an aromatic compound and a styrenic compound in a first reactor 1 of fixed-bed flow type in a liquid phase in the presence of a solid acid catalyst, (2) circulating a part of the reaction mixture from the above step to the first reactor 1, (3) feeding a reaction mixture flowing out from the first reactor to a second reactor 3, thereby reducing the content of unsaturated components with the aid of a solid acid catalyst, and (4) distilling the resultant reaction mixture, to thereby obtain a fraction having a reduced content of unsaturated components. The method can be used for producing an aromatic compound/styrenic compound adduct having a reduced content of unsaturated components in high yield and at a low cost.
    Type: Grant
    Filed: April 19, 2000
    Date of Patent: February 26, 2002
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Hideyuki Dohi, Shozo Hayashi
  • Patent number: 6339179
    Abstract: A process for producing alkyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. One portion of the transalkylation reaction zone effluent passes to an alkylation reaction zone where an aromatic substrate is alkylated to the desired alkyl aromatic. At least a portion of the alkylation reaction zone effluent and another portion of the transalkylation reaction zone effluent pass to a product recovery zone. This process decreases the capital and operating costs of recycling aromatic substrate to the transalkylation and/or alkylation reaction zone while maintaining operational flexibility. This process is well suited for solid transalkylation and alkylation catalysts. Ethylbenzene and cumene may be produced by this process.
    Type: Grant
    Filed: July 25, 2000
    Date of Patent: January 15, 2002
    Assignee: UOP LLC
    Inventors: Russell C. Schulz, Gregory J. Gajda, Guy B. Woodle, Andrew S. Zarchy
  • Patent number: 6096935
    Abstract: A process for producing alkyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. The transalkylation reaction zone effluent passes to the alkylation reaction zone where aromatics in the transalkylation reaction zone effluent are alkylated to the desired alkyl aromatics. This process decreases the capital and operating costs of recycling the aromatics in the transalkylation reaction zone effluent. This process is well suited for solid transalkylation and alkylation catalysts. Ethylbenzene and cumene may be produced by this process.
    Type: Grant
    Filed: July 28, 1998
    Date of Patent: August 1, 2000
    Assignee: UOP LLC
    Inventors: Russell C. Schulz, Gregory J. Gajda
  • Patent number: 6057487
    Abstract: A method is disclosed to produce 2,6-dimethylnaphthalene (2,6-DMN), used for the production of polyethylene naphthalate, at high purity and high yield from a mixture of dimethylnaphthalene isomers without limitation to the specific isomers present in the feed by a series of fractionation, crystallization and adsorption steps.
    Type: Grant
    Filed: December 30, 1997
    Date of Patent: May 2, 2000
    Assignee: Chevron Chemical Company
    Inventors: Curtis L. Munson, Patrick C. Bigot, Zunqing Alice He
  • Patent number: 6018086
    Abstract: The present invention relates to a process of preparing dialkylnaphthylenes and polyalkylenenaphthyleneates.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: January 25, 2000
    Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil Corporation
    Inventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul Mc Williams, Susan Patricia Donnelly
  • Patent number: 6015930
    Abstract: The invention discloses a method of making 2,6-dimethylnaphthalene from any DMN with one methyl on each ring in a two-step hydroisomerization/dehydrogenation process. The catalyst used in the hydroisomerization step is an acidic catalyst such as a silica aluminum catalyst with a hydrogenation/dehydrogenation metal. The catalyst used in the dehydrogenation step is a reforming type catalyst.
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: January 18, 2000
    Assignee: Chevron Chemical Company
    Inventors: Donald S. Santilli, Cong-Yan Chen
  • Patent number: 6011190
    Abstract: 2,6-Dialkylnaphthalene is prepared from a feedstock comprising naphthalene and an alkylating agent, by a process comprising the steps:(I) transalkylating isomers of dialkylnaphthalene and naphthalene to produce monoalkylnaphthalene and isomers of dialkylnaphthalene;(II) separating the product obtained in step (I) into naphthalene, monoalkylnaphthalene, dialkylnaphthalene and other components;(III) alkylating the monoalkylnaphthalene fraction from step (II) with an alkylating agent to produce dialkylnaphthalene; and(IV) separating 2,6-dialkylnaphthalene from the dialkylnaphthalene fraction in step (II),wherein at least step (I) or step (III) is conducted in the presence of a catalyst having a composition comprising a synthetic zeolite having an X-ray diffraction pattern with an interplanar d-spacing (.ANG.)______________________________________ 12.36 .+-. 0.4 11.03 .+-. 0.2 8.83 .+-. 0.14 6.18 .+-. 0.12 6.00 .+-. 0.10 4.06 .+-. 0.07 3.91 .+-. 0.07 3.42 .+-. 0.06.
    Type: Grant
    Filed: July 2, 1997
    Date of Patent: January 4, 2000
    Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil Corporation
    Inventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul McWilliams
  • Patent number: 5955641
    Abstract: The method of the invention includes making dimethyinaphthalenes by first contacting, in an alkylation zone, at alkylation conditions, a toluene-containing stream with a pentene-containing stream in the presence of an acid alkylation catalyst. At least a portion of the toluene and pentenes react to form pentyltoluenes. At least a portion of the pentyltoluenes is then contacting in a reforming zone with reforming catalyst, at reforming conditions. At least a portion of the pentyltoluenes is converted to dimethylnaphthalenes.
    Type: Grant
    Filed: May 28, 1998
    Date of Patent: September 21, 1999
    Assignee: Chevron Chemical Company LLC
    Inventors: Cong-Yan Chen, William L. Schinski, Dennis J. O'Rear, Thomas V. Harris
  • Patent number: 5952534
    Abstract: The invention is related to a process for making 2,6-dimethylnaphthalene from p-xylene and 1- or 2-butene or butadiene via 1-(p-tolyl)-2-methylbutane or 1-(p-tolyl)-2-methylbutane. 2,6-dimethylnaphthalene can be used for making polyethylenenaphthalate.
    Type: Grant
    Filed: March 20, 1998
    Date of Patent: September 14, 1999
    Assignee: Optatech Oy
    Inventors: Kari Vahteristo, Erkki Halme, Salme Koskimies, Sigmund M. Csicsery, Markku Laatikainen, Vesa Niemi
  • Patent number: 5744670
    Abstract: A process for producing alkylnaphthalene from a feedstock comprising isomers of dialkylnaphthalene and naphthalene by contacting the feedstock with a catalyst composition, in which the process comprising transalkylation between isomers of dialkylnaphthalene and naphthalene to produce monoalkylnaphthalene, and isomerization of dialkylnaphthalene, wherein the catalyst composition comprising a synthetic zeolite characterized by an X-ray diffraction pattern including interplanar d-spacing as set forth in Table A of the specification.
    Type: Grant
    Filed: June 10, 1996
    Date of Patent: April 28, 1998
    Assignees: Kobe Steel, Ltd., Mobil Oil Corporation
    Inventors: Masahiro Motoyuki, Koji Yamamoto, John Paul McWilliams, Robert Glenn Bundens
  • Patent number: 5401892
    Abstract: A method for preparing one or more specific dimethyltetralins from either 5-(o-, m-, or p-tolyl)-pent-1- or -2-ene or 5-phenyl-hex-1- or -2-ene, and optionally for preparing one or more specific dimethylnaphthalenes from the aforesaid dimethyltetralins is disclosed wherein the orthotolylpentene or phenylhexane is cyclized to the dimethyltetralin using an ultra-stable crystalline aluminosilicate molecular sieve Y-zeolite.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: March 28, 1995
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Ian C. Zaenger, Joyce D. Lamb, Gregory S. Williams
  • Patent number: 5396008
    Abstract: There is disclosed a process for producing dimethyltetralin consisting of 1,5-, 1,6- and 2,6-dimethyltetralin which comprises cyclizing 5-tolyl-penta-2-ene in gaseous state in the presence of diluent by the use of a catalyst comprising a crystalline aluminosilicate and a carrier and optionally a molding assistant. The abovementioned process is capable of producing industrially useful dimethyltetralin as the starting raw material for dimethylnaphthalene with high yield and high selectivity with minimized side reactions over a long stabilized period.
    Type: Grant
    Filed: July 9, 1993
    Date of Patent: March 7, 1995
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Shinji Ozawa, Makoto Takagawa, Kenji Dnamasa
  • Patent number: 5300717
    Abstract: In a multi-step process, dixylylpropane is obtained inter alia via the hitherto unknown 1,2-dimethyl-4-(.alpha.-chloroisopropyl)benzene, the readily accessible compounds o-xylene and propene being employed as starting compounds. The process yields the desired compound in high yield and isomer purity and is distinguished by a small amount of by-products. It is therefore particularly suitable for further processing without problems. The process involves the sequence of (a) Friedel-Crafts alkylation of ortho-xylene with propylene, (b) dehydrogenation of the isoproplyxlene into isopropenylxylene, (c) which is then hydrochlorinated into chloroisopropylxylene, (d) and then alkylated with a second ortho-xylene modecule to obtain the final product dixylylpropane.
    Type: Grant
    Filed: April 8, 1993
    Date of Patent: April 5, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Freimund Rohrscheid
  • Patent number: 5284987
    Abstract: A method for the acid catalyzed cyclization of an alkenylbenzene feedstock to a dimethyltetralin in a liquid phase reaction wherein the desired dimethyltetralin is removed from the reaction mixture by distillation simultaneously with the addition of the feedstock to the reaction mixture.
    Type: Grant
    Filed: February 5, 1992
    Date of Patent: February 8, 1994
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Ian C. Zaenger, Gregory S. Williams
  • Patent number: 5276230
    Abstract: There is disclosed a process for efficiently producing 2,6-dimethylnaphthalene used for the production of polyethylene naphthalate which comprises subjecting 2-methyl-1-(p-tolyl)butene and/or 2-methyl-1-(p-tolyl)butane as a starting raw material to cyclization dehydrogenation reaction by the use of a catalyst comprising a platinum component and at least one component selected from the group consisting of alkali metals and alkaline earth metals each being supported on aluminum oxide. The above process enables the production of the objective compound in a high yield at a low cost by using the catalyst having high safety and stability from the widely available starting material, thereby enhancing the industrial significance of the process.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: January 4, 1994
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kenji Inamasa, Norio Fushimi, Makoto Takagawa
  • Patent number: 5189234
    Abstract: A process for selectively dehydrogenating organic compounds, and particularly for dehydrogenating dimethyltetralins to dimethylnaphthalenes, by contacting the organic compound at an elevated temperature with a catalyst prepared by treating a composition comprising an alumina support material and platinum group metal with an excess amount of an alkaline solution of an alkali metal salt.
    Type: Grant
    Filed: October 31, 1991
    Date of Patent: February 23, 1993
    Assignee: Amoco Corporation
    Inventor: Jeffrey A. Amelse
  • Patent number: 5136114
    Abstract: The invention relates to a new process for the preparation of geminal diarylalkanes of the formula ##STR1## by Friedel-Crafts alkylation of aromatic compounds with specific aliphatic halogen compounds (addition compounds of CCl.sub.4 , to .alpha.-olefins), to new geminal diarylalkanes and the aralkyl compounds resulting as intermediates.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 5118892
    Abstract: A method for preparing one or more diemthylnaphthalenes from one or more dimethyltetralins, and optionally for preparing one or more other specific dimethylnaphthalenes by isomerization of the aforesaid dimethylnaphthalene(s) is disclosed.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: June 2, 1992
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Ian C. Zaenger, Gregory S. Williams
  • Patent number: 5073670
    Abstract: A method for preparing one or more specific dimethyltetralins from either 5-(o-, m-, or p-tolyl)-pent-1-or -2-ene or 5-phenyl-hex-1- or -2-ene, and optionally for preparing one or more specific dimethylnaphthalenes from the aforesaid dimethyltetralins is disclosed.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: December 17, 1991
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Joyce D. Lamb, Ian C. Zaenger, Gregory S. Williams
  • Patent number: 5068480
    Abstract: A process for producing 2,6-dimethylnaphthalene, which comprises subjecting 2-methyl-1-(p-tolyl)-butene, 2-methyl-1-(p-tolyl)-butane or a mixture of these to cyclization and dehydrogenation in the presence of a catalyst comprising lead oxide and/or indium oxide and aluminum oxide.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: November 26, 1991
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Makoto Takagawa, Ken Yamagishi, Jyun Yoshihara, Kenji Inamasa, Kumiko Watabe
  • Patent number: 5030781
    Abstract: A method for preparing one or more specific dimethyltetralins by cyclization of either 5-(o-, m, or p-tolyl)-pent-1- or -2-ene or 5-phenyl-hex-1- or -2-ene, with additional cyclization treatment, and optionally cracking, of a heavy fraction of the cyclization product, is disclosed.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: July 9, 1991
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Ian C. Zaenger, Gregory S. Williams
  • Patent number: 5023390
    Abstract: A process for production of 2,6-dimethylnaphthalene is disclosed; comprising the steps: (1) an acylation step where 2,4-dimethylisobutyrophenone is produced from m-xylene, propylene and carbon monoxide: (2) a hydrogenation step where the carbonyl group of the above 2,4-dimethylisobutyrophenone is hydrogenated: and (3) a dehydrogenation and cyclization step where the above hydrogenated product is subjected to dehydrogenation and cyclization to produce the desired 2,6-dimethylnaphthalene. The process enables efficiently producing high quality or high purity 2,6-dimethylnaphthalene.
    Type: Grant
    Filed: September 12, 1989
    Date of Patent: June 11, 1991
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takafumi Abe, Shuji Ebata, Hiroshi Machida, Koichi Kida
  • Patent number: 5013424
    Abstract: A process for the production of hydrogenated, distillable hydrocarbonaceous product from a feed comprising hydrocarbonaceous compounds and having a non-distillable component, and a feed comprising halogenated organic compounds by means of contacting the feed comprising hydrocarbonaceous compounds and having a non-distillable component with a hot hydrogen-rich gaseous stream to increase the temperature of this feed stream to vaporize at least a portion of the distillable hydrocarbonaceous compounds thereby producing a distillable hydrocarbonaceous product which is immediately hydrogenated in an integrated hydrogenation zone. The feed comprising halogenated organic compounds is contacted in a second hydrogenated hydrocarbonaceous product and at least one water-soluble inorganic halide compound.
    Type: Grant
    Filed: July 30, 1990
    Date of Patent: May 7, 1991
    Assignee: UOP
    Inventors: Robert B. James, Jr., Tom N. Kalnes, Steven P. Lankton
  • Patent number: 5012024
    Abstract: A method for preparing one or more dimethylnaphthalenes from one or more dimethyltetralins, and optionally for preparing one or more other specific dimethylnaphthalenes by isomerization of the aforesaid dimethylnaphthal-dimethylnaphthalene(s) is disclosed.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: April 30, 1991
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Ian C. Zaenger, Gregory S. Williams
  • Patent number: 5008479
    Abstract: A process for production of 2,6-dimethylnaphthalene is disclosed, comprising the steps: (1) an acylation step where p-tolyl sec-butyl ketone is produced from toluene, n-butene and carbon monoxide: (2) a hydrogenation step where the carbonyl group of the p-tolyl sec-butyl ketone is hydrogenated: and (3) a dehydrogenation and cyclization step where the hydrogenated product obtained above is subjected to dehydrogenation and cyclization to produce the desired 2,6-dimethylnaphthalene. The process enables efficiently producing a high quality or high purity 2,6-dimethylnaphthalene.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: April 16, 1991
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takafumi Abe, Seiji Uchiyama, Takahiro Ojima, Koichi Kida
  • Patent number: 4999450
    Abstract: A process for preparing .alpha.-(3-benzylphenyl)-propionic acid or its derivative, a precursor of ketoprofen (trade name), which comprises dehydrogenating a by-product oil fraction formed in the production of ethylbenzene using synthetic zeolite as an alkylating catalyst, and carbonylating the product with carbon monoxide or the like. This precursor can be easily converted into ketoprofen, a useful medicine as an anti-inflammatory agent.
    Type: Grant
    Filed: March 23, 1990
    Date of Patent: March 12, 1991
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
  • Patent number: 4982029
    Abstract: A method for the direct preparation of olefins from ketones and Grignard reagents without isolation of the intermediate alcohol and in the absence of acidic dehydration catalysts. Ketones are reacted with a Grignard reagent in the presence of a low boiling solvent for the Grignard reagent to form a Grignard reaction mixture. An active hydrogen-containing compound is added to the Grignard reaction mixture to form a reaction mixture comprising an alcohol and Grignard salts. The alcohol is dehydrated in the presence of the Grignard salts and a solvent which has a higher boiling point than solvents typically emloyed during the Grignard condensation. The higher boiling solvent can be an active hydrogen-containing compound such as n-octanol and otherwise can be added at any time, including the initial condensation step.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: January 1, 1991
    Assignee: The Dow Chemical Company
    Inventor: Kuo-Yuan Chang, deceased
  • Patent number: 4957815
    Abstract: Polyarylalkane oligomer compositions consisting essentially of a mixture of isomers of xylyl-xylene and of higher homologues and a mixture of isomers of bis(dimethylphenyl)xylylene and of higher homologues; the method of making such compositions by first reacting toluene, xylene, or a mixture of toluene and xylene with chlorine in the presence of a radical generator, removing the unreacted toluene, and then subjecting the reaction product to the action of an inorganic halide or inorganic acid in the presence of xylene, and microcapsules containing color-forming material wherein the compositions are used as solvents for the color-forming material.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: September 18, 1990
    Assignee: Societe Atochem
    Inventors: Raymond Commandeur, Bernard Gurtner
  • Patent number: 4956120
    Abstract: Polyarylalkane oligomer compositions containing essentially of a mixture of isomers of benzylcumene and its higher homologues and a mixture of isomers of bis(isopropylphenyl)phenylmethane; the method of making such compositions by first reacting chlorine with toluene, xylene, or a mixture of toluene and xylene in the presence of a radical generator, removing the unreacted toluene and/or xylene, and then subjecting the reaction product to the action of an inorganic halide or of an inorganic acid in the presence of a benzene-related compound; and microcapsules containing color-forming material wherein the compositions are used as solvents for the color-forming material.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: September 11, 1990
    Assignee: Atochem
    Inventors: Raymond Commandeur, Bernard Gurtner
  • Patent number: 4950825
    Abstract: A method for preparing one or more specific dimethyltetralins from either 5-(o-, m-, or p-tolyl)-pent-1- or -2-ene or 5-phenyl-hex-1- or -2-ene, and optionally for preparing one or more specific dimethylnaphthalenes from the aforesaid dimethyltetralins is disclosed.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: August 21, 1990
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, Joyce D. Lamb, Ian C. Zaenger, Gregory S. Williams
  • Patent number: 4950824
    Abstract: A process for the production of 2,6-diisopropylnaphthalene is disclosed wherein an isopropylation reaction mixture containing isopropylated naphthalenes is subjected to transalkylation with a triisopropylnaphthalene-containing mixture to obtain a mixture containing mono-, di- and tri-isopropylnaphthalenes which is then separated into a first fraction containing monisopropylnaphthalenes, a second fraction containing diisopropylnaphthalenes and a third fraction containing triisopropylnaphthalenes. The first and third fractions are recycled to the above system, while the second fraction is subjected to separation treatments for the recovery of 2,6-diisopropylnaphthalene. The second fraction from which 2,6-diisopropylnaphthalene has been removed is subjected to transalkylation with naphthalene to obtain a monoisopropylnaphthalene-rich mixture which is to be fed to the isopropylation step.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: August 21, 1990
    Assignees: Chiyoda Corporation, NKK Corporation
    Inventors: Yoshimi Shiroto, Mitsunori Shimura, Kenji Shimokawa, Yoshio Fukui, Sachio Asaoka, Hiroto Tajima, Kazuaki Ueda, Yakudo Tachibana, Kazuhiko Tate, Hiroaki Taniguchi
  • Patent number: 4929781
    Abstract: A process for the simultaneous hydroconversion of a first feedstock comprising unsaturated, halogenated organic compounds and a second feedstock comprising saturated, halogenated organic compounds which process comprises: (a) contacting the first feedstock comprising unsaturated, halogenated organic compounds with hydrogen in a first hydrogenation reaction zone operated at hydrogenation conditions selected to minimize the polymerization of unsaturated organic compounds and to produce a first hydrogenated hydrocarbonaceous stream; (b) contacting at least a portion of the first hydrogenated hydrocarbonaceous stream and the second feedstock comprising saturated, halogenated organic compounds with hydrogen in a second hydrogenation reaction zone operated at hydrogenation conditions selected to produce a second hydrogenated hydrocarbonaceous stream and to generate at least one water-soluble hydrogen halide compound; (c) contacting the resulting effluent from the second hydrogenation zone containing hydrogenated hy
    Type: Grant
    Filed: November 30, 1988
    Date of Patent: May 29, 1990
    Assignee: UOP
    Inventors: Robert B. James, Jr., Tom N. Kalnes
  • Patent number: 4902842
    Abstract: A process for the simultaneous hydroconversion of a first feedstock comprising unsaturated, halogenated organic compounds and a second feedstock comprising saturated, halogenated organic compounds which process comprises: (a) contacting the first feedstock comprising unsaturated, halogenated organic compounds with a first dried hydrogen-rich gas stream in a first hydrogenation reaction zone operated at hydrogenation conditions selected to minimize the polymerization of unsaturated organic compounds and to produce a first hydrogenated stream comprising hydrocarbonaceous compounds; (b) reacting at least a portion of the first hydrogenated stream comprising hydrocarbonaceous compounds and the second feedstock comprising saturated, halogenated organic compounds with hydrogen in a second hydrogenation reaction zone operated at hydrogenation conditions selected to produce a second hydrogenated stream comprising hydrocarbonaceous compounds and to generate at least one water-soluble hydrogen halide compound; (c) cont
    Type: Grant
    Filed: February 13, 1989
    Date of Patent: February 20, 1990
    Assignee: UOP
    Inventors: Tom N. Kalnes, Robert B. James, Jr.
  • Patent number: 4899001
    Abstract: A process for the simultaneous hydroconversion of a first feedstock comprising unsaturated, halogenated organic compounds and a second feedstock comprising saturated, halogenated organic compounds which process comprises: (a) reacting the first feedstock comprising unsaturated, halogenated organic compounds with hydrogen in a first hydrogenation reaction zone operated at hydrogenation conditions selected to minimize the polymerization of unsaturated organic compounds and to produce a first hydrogenated stream comprising hydrocarbonaceous compounds; (b) reacting at least a portion of the first hydrogenated stream comprising hydrocarbonaceous compounds and the second feedstock comprising saturated, halogenated organic compounds with hydrogen in a second hydrogenated reaction zone operated at hydrogenation conditions selected to produce a second hydrogenated stream comprising hydrocarbonaceous compounds and to generate at least one water-soluble inorganic halide compound; (c) contacting the resulting effluent fr
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: February 6, 1990
    Assignee: UOP
    Inventors: Tom N. Kalnes, Robert B. James, Jr.
  • Patent number: 4895995
    Abstract: A process for the simultaneous hydroconversion of a first feestock comprising unsaturated, halogenated organic compounds and a second feedstock comprising saturated, halogenated organic compounds which process comprises: (a) contacting the first feedstock comprising unsaturated, halogenated organic compounds with hydrogen in a first hydrogenation reaction zone (b) contacting at least a portion of the first hydrogenated stream and the second feedstock comprising saturated, halogenated organic compounds with hydrogen in a second hydrogenation reaction zone; (c) contacting the resulting effluent from the second hydrogenation zone comprising hydrogenated hydrocarbonaceous compounds, residual trace quantities of halogenated organic compounds, a hydrogen-rich gas and at least one water-soluble hydrogen halide compound with a halide-lean absorber solution in an absorption zone; (d) withdrawing a halide-rich absorber solution containing at least a portion of the water-soluble hydrogen halide compound from the absorpt
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: January 23, 1990
    Assignee: UOP
    Inventors: Robert B. James, Jr., Tom N. Kalnes
  • Patent number: 4855518
    Abstract: A method for producing p-alkylstyrene which is characterized in that side reaction scarcely occurs, catalyst and unreacted material are easily recovered for the reuse, the p-position selectivity is excellent and yield of aimed product is high. In the method, monoalkylbenzene having an alkyl group with 3 or more carbon atoms is reacted with acetaldehyde in the presence of hydrogen fluoride catalyst under the conditions of a temperature of 0.degree. C. or lower, a molar ratio of 2 to 100 in "alkylbenzene/acetaldehyde", the other molar ratio of 1.7 to 300 in "hydrogen fluoride/acetaldehyde", the proportion of hydrogen fluoride to the sum of hydrogen fluoride and water in the reaction system of 65% by weight or higher, and the concentration of acetaldehyde in the reaction system of 1.0% by weight or lower to obtain 1,1-bis(p-alkylphenyl)ethane, and then subjecting it to catalytic cracking at a temperature in the range of 200.degree. to 650.degree. C. in the presence of an acid catalyst.
    Type: Grant
    Filed: July 19, 1988
    Date of Patent: August 8, 1989
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Yuuichi Tokumoto
  • Patent number: 4855519
    Abstract: A method for producing arylethylene comprising four steps of: (I) bringing 1,1-diarylethane into contact with an acid catalyst in the presence of an inert gas to crack said compound into arylethylenes and alkylbenzenes; (II) separating the reaction mixture obtained in the above cracking step (I) into at least a fraction mainly containing 1,1-diarylethane; (III) bringing said fraction mainly containing 1,1-diarylethane into contact with hydrogen gas in the presence of a hydrogenation catalyst; and (IV) re-cracking hydrogenated fraction obtained in the preceding hydrogenation step (III) by bringing it into said cracking step (I).Particularly, this method is useful for producing p-isobutylstyrene which is a starting material for preparing a valuable medicine of ibuprofen.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: August 8, 1989
    Assignee: Nippon Petrochemicals Company
    Inventors: Isoo Shimizu, Hitoshi Mitsuyuki, Kazumichi Uchida, Yuuichi Tokumoto
  • Patent number: 4827065
    Abstract: A method for producing p-isobutylstyrene which is characterized in that starting materials are inexpensive, processes are easy to be done and products are highly pure. The method comprises the step of catalytically cracking 1,1-bis(p-isobutylphenyl)ethane at temperatures in the range of 200.degree. to 650.degree. C. in the presence of a protonic acid catalyst and/or a solid acid catalyst to produce p-isobutylstyrene and isobutylbenzene, and at least a portion of said isobutylbenzene is recycled to produce said 1,1-bis(p-isobutylphenyl)ethane by reaction with acetaldehyde in the presence of sulfuric acid.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: May 2, 1989
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Ryotaro Hirano, Yasuo Matsumura, Hideki Nomura, Kazumichi Uchida, Atsushi Sato
  • Patent number: 4802058
    Abstract: The present invention relates to a method for refining an electrical insulating oil by refining a heavy by-product oil obtained in the preparation of ethylbenzene or ethyltoluene. The method comprises distilling off the lighter components from the by-product oil, then dehydrogenating, distilling and hydrogenating.
    Type: Grant
    Filed: March 9, 1988
    Date of Patent: January 31, 1989
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Shigenobu Kawakami, Keiji Endo, Hideyuki Dohi, Atsushi Sato
  • Patent number: 4775460
    Abstract: Problems associated with the formation of polycyclic aromatic compounds within hydrocracking reaction zones are reduced by a feed pretreating sequence which comprises first contacting the feed with a metal-free alumina to produce polycyclic compounds or their precursors followed by their removal by contacting the feed with a bed of adsorbent such as charcoal. The feed pretreatment steps are operated at an elevated temperature but at a very reduced pressure and preferably substantially free of hydrogen.
    Type: Grant
    Filed: December 24, 1987
    Date of Patent: October 4, 1988
    Assignee: UOP, Inc.
    Inventor: Mark E. Reno
  • Patent number: 4665246
    Abstract: The process of producing ethynyl aromatic compounds which are useful as intermediates in the preparation of 3-dimensional carbon-carbon structures for aerospace and military applications and as starting materials in the preparation of organic semi-conductors. The ethynyl aromatic compounds may be any of the classes illustrated in FIGS. 1, 2 and 3 of the drawing. Starting compounds for the process may by any compound from the classes illustrated in FIGS. 4, 5 and 6. The starting compound is reacted in the presence of a Friedel-Crafts catalyst in a suitable solvent with an acyl compound from the class illustrated in FIG. 7 to yield a compound within the classes illustrated in FIGS. 8, 9 and 10. The carbonyl groups in this compound are reduced to yield a corresponding alcohol. Each hydroxy group in the alcohol is converted to an easily eliminatable group, e.g., by reacting it with methane sulfonyl chloride, when subjected to basic conditions.
    Type: Grant
    Filed: March 9, 1984
    Date of Patent: May 12, 1987
    Assignee: Chem Biochem Research, Inc.
    Inventor: Chris Anderson
  • Patent number: 4649207
    Abstract: Derivatives of diphenylhexafluoropropane having the formula: ##STR1## where R is an unsubstituted or substituted alkylene, an epoxy, a silyl or alkoxysilyl group; and where X and Y are hydrogen or halogen. The derivatives are useful in formulating polymer structures.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: March 10, 1987
    Assignee: Hughes Aircraft Company
    Inventors: Kreisler S. Y. Lau, William J. Kelleghan
  • Patent number: 4596896
    Abstract: The self condensation of monovinyl aromatic compounds to acyclic dimers, the cross-reaction of monovinyl aromatic compounds with olefins in the presence of acid catalysts to produce cyclialkylated aromatic compounds, and the production of cyclialkylated aromatic compounds by reaction of olefins with acyclic dimers of monovinyl aromatic compounds in the presence of acid catalysts is improved by employing a tetrahydrothiophene 1,1-dioxide solvent.
    Type: Grant
    Filed: June 3, 1985
    Date of Patent: June 24, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Raymond L. Cobb
  • Patent number: 4523044
    Abstract: Polyarylalkane oligomer compositions comprising a mixture of two oligomers A and B, wherein oligomer A is a mixture of isomers of formula: ##STR1## with n1 and n2=0, 1 and 2, given that n1+n2.ltoreq.3; and oligomer B is a mixture of isomers of formula: ##STR2## with n'1, n"1 and n4=0, 1 and 2, n'2, n"2, n3, n'3 and n5=0 and 1, given that n'1+n"1+n'2+n"2+n3+n'3+n4+n5.ltoreq.2.The invention also comprises the process for the preparation of said oligomer compositions by the action of a halide or inorganic acid on a product of free-radical chlorination of toluene.
    Type: Grant
    Filed: September 13, 1984
    Date of Patent: June 11, 1985
    Assignee: Atochem
    Inventors: Raymond Commandeur, Bernard Gurtner
  • Patent number: 4440957
    Abstract: Process of preparing .beta.-isopropylnaphthalene substantially free of corresponding .alpha.-isomer, in yields amounting to 90% and more by a continuous two-stage process comprising (1) alkylating naphthalene with propylene at a temperature of about 150.degree.-280.degree. C. under a pressure of 5 to 30 atm in the presence of a phosphoric acid catalyst supported on a SiO.sub.2 carrier and using a mol ratio of 1/5 to 1/20 mol propylene to 1 mol naphthalene to isopropylate 45 to 65% of the naphthalene and form a mixture of .alpha.- and .beta.-isopropylnaphthalene and then without separating off the unreacted naphthalene, (2) heating the isomeric mixture from stage (1) in the presence of a phosphoric acid catalyst supported on SiO.sub.2, to a temperature of 180.degree.-280.degree. C. under an inert gas pressure of 5 to 30 atm until no further .beta.-isopropylnaphthalene is formed and recovering said .beta.-isopropylnaphthalene from the isomerization mixture.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: April 3, 1984
    Assignee: Bergwerksverband GmbH
    Inventors: Kurt Handrick, Georg Kolling, Paul Kiedel
  • Patent number: 4405513
    Abstract: Compounds useful as fluorescers in aqueous chemiluminescent mixtures, have the formula ##STR1## wherein X and Y represent hydrogen, or a quaternary ammonium group ##STR2## wherein m is 0 or 1n is an integer from one to fiveR.sub.1, R.sub.2, R.sub.3 represent C.sub.1 -C.sub.8 alkyl, or two of them form ring with N to make piperidinium, morpholinium or pyrrolidinium, andZ is an ion,the compound having at least one such quaternary group.
    Type: Grant
    Filed: June 16, 1982
    Date of Patent: September 20, 1983
    Assignee: American Cyanamid Company
    Inventor: Victor M. Kamhi