Polycyclic Patents (Class 585/320)
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Patent number: 7323610Abstract: 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: GrantFiled: July 27, 2004Date of Patent: January 29, 2008Assignee: Eastman Kodak CompanyInventors: William J. Begley, Manju Rajeswaran, Natasha Andrievsky
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Patent number: 7019186Abstract: 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: GrantFiled: February 4, 2003Date of Patent: March 28, 2006Assignees: Enichem S.p.A., ENI S.p.A., Enitecnologie S.p.A.Inventors: Giannino Pazzuconi, Carlo Perego, Giuseppe Bellussi
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Publication number: 20020119391Abstract: 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: ApplicationFiled: February 23, 2001Publication date: August 29, 2002Applicant: Shipley Company, L.L.C.Inventors: George G. Barclay, Anthony Zampini
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Patent number: 6380450Abstract: 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: GrantFiled: April 15, 2000Date of Patent: April 30, 2002Assignee: Nippon Petrochemicals Company, LimitedInventor: Yasuo Matsumura
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Patent number: 6350930Abstract: 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: GrantFiled: April 19, 2000Date of Patent: February 26, 2002Assignee: Nippon Petrochemicals Company, LimitedInventors: Hideyuki Dohi, Shozo Hayashi
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Patent number: 6339179Abstract: 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: GrantFiled: July 25, 2000Date of Patent: January 15, 2002Assignee: UOP LLCInventors: Russell C. Schulz, Gregory J. Gajda, Guy B. Woodle, Andrew S. Zarchy
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Patent number: 6096935Abstract: 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: GrantFiled: July 28, 1998Date of Patent: August 1, 2000Assignee: UOP LLCInventors: Russell C. Schulz, Gregory J. Gajda
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Patent number: 6057487Abstract: 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: GrantFiled: December 30, 1997Date of Patent: May 2, 2000Assignee: Chevron Chemical CompanyInventors: Curtis L. Munson, Patrick C. Bigot, Zunqing Alice He
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Patent number: 6018086Abstract: The present invention relates to a process of preparing dialkylnaphthylenes and polyalkylenenaphthyleneates.Type: GrantFiled: October 10, 1997Date of Patent: January 25, 2000Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil CorporationInventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul Mc Williams, Susan Patricia Donnelly
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Patent number: 6015930Abstract: 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: GrantFiled: July 14, 1997Date of Patent: January 18, 2000Assignee: Chevron Chemical CompanyInventors: Donald S. Santilli, Cong-Yan Chen
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Patent number: 6011190Abstract: 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: GrantFiled: July 2, 1997Date of Patent: January 4, 2000Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil CorporationInventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul McWilliams
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Patent number: 5955641Abstract: 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: GrantFiled: May 28, 1998Date of Patent: September 21, 1999Assignee: Chevron Chemical Company LLCInventors: Cong-Yan Chen, William L. Schinski, Dennis J. O'Rear, Thomas V. Harris
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Patent number: 5952534Abstract: 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: GrantFiled: March 20, 1998Date of Patent: September 14, 1999Assignee: Optatech OyInventors: Kari Vahteristo, Erkki Halme, Salme Koskimies, Sigmund M. Csicsery, Markku Laatikainen, Vesa Niemi
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Patent number: 5744670Abstract: 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: GrantFiled: June 10, 1996Date of Patent: April 28, 1998Assignees: Kobe Steel, Ltd., Mobil Oil CorporationInventors: Masahiro Motoyuki, Koji Yamamoto, John Paul McWilliams, Robert Glenn Bundens
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Patent number: 5401892Abstract: 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: GrantFiled: February 26, 1993Date of Patent: March 28, 1995Assignee: Amoco CorporationInventors: David L. Sikkenga, Ian C. Zaenger, Joyce D. Lamb, Gregory S. Williams
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Patent number: 5396008Abstract: 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: GrantFiled: July 9, 1993Date of Patent: March 7, 1995Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Shinji Ozawa, Makoto Takagawa, Kenji Dnamasa
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Patent number: 5300717Abstract: 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: GrantFiled: April 8, 1993Date of Patent: April 5, 1994Assignee: Hoechst AktiengesellschaftInventor: Freimund Rohrscheid
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Patent number: 5284987Abstract: 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: GrantFiled: February 5, 1992Date of Patent: February 8, 1994Assignee: Amoco CorporationInventors: David L. Sikkenga, Ian C. Zaenger, Gregory S. Williams
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Patent number: 5276230Abstract: 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: GrantFiled: September 14, 1992Date of Patent: January 4, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kenji Inamasa, Norio Fushimi, Makoto Takagawa
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Patent number: 5189234Abstract: 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: GrantFiled: October 31, 1991Date of Patent: February 23, 1993Assignee: Amoco CorporationInventor: Jeffrey A. Amelse
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Patent number: 5136114Abstract: 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: GrantFiled: April 30, 1990Date of Patent: August 4, 1992Assignee: Bayer AktiengesellschaftInventor: Dieter Arlt
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Patent number: 5118892Abstract: 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: GrantFiled: July 20, 1990Date of Patent: June 2, 1992Assignee: Amoco CorporationInventors: David L. Sikkenga, Ian C. Zaenger, Gregory S. Williams
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Patent number: 5073670Abstract: 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: GrantFiled: July 20, 1990Date of Patent: December 17, 1991Assignee: Amoco CorporationInventors: David L. Sikkenga, Joyce D. Lamb, Ian C. Zaenger, Gregory S. Williams
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Patent number: 5068480Abstract: 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: GrantFiled: December 3, 1990Date of Patent: November 26, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Makoto Takagawa, Ken Yamagishi, Jyun Yoshihara, Kenji Inamasa, Kumiko Watabe
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Patent number: 5030781Abstract: 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: GrantFiled: June 15, 1990Date of Patent: July 9, 1991Assignee: Amoco CorporationInventors: David L. Sikkenga, Ian C. Zaenger, Gregory S. Williams
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Patent number: 5023390Abstract: 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: GrantFiled: September 12, 1989Date of Patent: June 11, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takafumi Abe, Shuji Ebata, Hiroshi Machida, Koichi Kida
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Patent number: 5013424Abstract: 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: GrantFiled: July 30, 1990Date of Patent: May 7, 1991Assignee: UOPInventors: Robert B. James, Jr., Tom N. Kalnes, Steven P. Lankton
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Patent number: 5012024Abstract: 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: GrantFiled: February 27, 1989Date of Patent: April 30, 1991Assignee: Amoco CorporationInventors: David L. Sikkenga, Ian C. Zaenger, Gregory S. Williams
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Patent number: 5008479Abstract: 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: GrantFiled: July 5, 1989Date of Patent: April 16, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takafumi Abe, Seiji Uchiyama, Takahiro Ojima, Koichi Kida
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Patent number: 4999450Abstract: 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: GrantFiled: March 23, 1990Date of Patent: March 12, 1991Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
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Patent number: 4982029Abstract: 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: GrantFiled: December 16, 1988Date of Patent: January 1, 1991Assignee: The Dow Chemical CompanyInventor: Kuo-Yuan Chang, deceased
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Patent number: 4957815Abstract: 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: GrantFiled: July 1, 1988Date of Patent: September 18, 1990Assignee: Societe AtochemInventors: Raymond Commandeur, Bernard Gurtner
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Patent number: 4956120Abstract: 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: GrantFiled: July 1, 1988Date of Patent: September 11, 1990Assignee: AtochemInventors: Raymond Commandeur, Bernard Gurtner
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Patent number: 4950824Abstract: 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: GrantFiled: August 2, 1989Date of Patent: August 21, 1990Assignees: Chiyoda Corporation, NKK CorporationInventors: Yoshimi Shiroto, Mitsunori Shimura, Kenji Shimokawa, Yoshio Fukui, Sachio Asaoka, Hiroto Tajima, Kazuaki Ueda, Yakudo Tachibana, Kazuhiko Tate, Hiroaki Taniguchi
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Patent number: 4950825Abstract: 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: GrantFiled: February 27, 1989Date of Patent: August 21, 1990Assignee: Amoco CorporationInventors: David L. Sikkenga, Joyce D. Lamb, Ian C. Zaenger, Gregory S. Williams
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Patent number: 4929781Abstract: 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 hyType: GrantFiled: November 30, 1988Date of Patent: May 29, 1990Assignee: UOPInventors: Robert B. James, Jr., Tom N. Kalnes
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Patent number: 4902842Abstract: 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) contType: GrantFiled: February 13, 1989Date of Patent: February 20, 1990Assignee: UOPInventors: Tom N. Kalnes, Robert B. James, Jr.
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Patent number: 4899001Abstract: 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 frType: GrantFiled: November 21, 1988Date of Patent: February 6, 1990Assignee: UOPInventors: Tom N. Kalnes, Robert B. James, Jr.
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Patent number: 4895995Abstract: 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 absorptType: GrantFiled: December 2, 1988Date of Patent: January 23, 1990Assignee: UOPInventors: Robert B. James, Jr., Tom N. Kalnes
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Patent number: 4855519Abstract: 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: GrantFiled: November 14, 1988Date of Patent: August 8, 1989Assignee: Nippon Petrochemicals CompanyInventors: Isoo Shimizu, Hitoshi Mitsuyuki, Kazumichi Uchida, Yuuichi Tokumoto
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Patent number: 4855518Abstract: 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: GrantFiled: July 19, 1988Date of Patent: August 8, 1989Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yuuichi Tokumoto
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Patent number: 4827065Abstract: 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: GrantFiled: July 10, 1985Date of Patent: May 2, 1989Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Ryotaro Hirano, Yasuo Matsumura, Hideki Nomura, Kazumichi Uchida, Atsushi Sato
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Patent number: 4802058Abstract: 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: GrantFiled: March 9, 1988Date of Patent: January 31, 1989Assignee: Nippon Petrochemicals Company, LimitedInventors: Shigenobu Kawakami, Keiji Endo, Hideyuki Dohi, Atsushi Sato
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Patent number: 4775460Abstract: 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: GrantFiled: December 24, 1987Date of Patent: October 4, 1988Assignee: UOP, Inc.Inventor: Mark E. Reno
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Patent number: 4665246Abstract: 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: GrantFiled: March 9, 1984Date of Patent: May 12, 1987Assignee: Chem Biochem Research, Inc.Inventor: Chris Anderson
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Patent number: 4649207Abstract: 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: GrantFiled: May 13, 1986Date of Patent: March 10, 1987Assignee: Hughes Aircraft CompanyInventors: Kreisler S. Y. Lau, William J. Kelleghan
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Patent number: 4596896Abstract: 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: GrantFiled: June 3, 1985Date of Patent: June 24, 1986Assignee: Phillips Petroleum CompanyInventor: Raymond L. Cobb
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Patent number: 4523044Abstract: 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: GrantFiled: September 13, 1984Date of Patent: June 11, 1985Assignee: AtochemInventors: Raymond Commandeur, Bernard Gurtner
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Patent number: 4440957Abstract: 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: GrantFiled: August 3, 1981Date of Patent: April 3, 1984Assignee: Bergwerksverband GmbHInventors: Kurt Handrick, Georg Kolling, Paul Kiedel
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Patent number: 4405513Abstract: 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: GrantFiled: June 16, 1982Date of Patent: September 20, 1983Assignee: American Cyanamid CompanyInventor: Victor M. Kamhi