Arylene Bond Formed Using Metal-containing Agent Patents (Class 585/427)
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Patent number: 10294172Abstract: Provided here are processes and systems for conversion of alkyl-bridged non-condensed alkyl multi-aromatic compounds to alkyl mono-aromatic compounds. One system includes a hydrodearylation reactor adapted to receive a hydrogen stream and a feed stream and to produce a reactor effluent stream in presence of a catalyst. The feed stream contains one or more of heavy alkyl aromatic compounds and one or more alkyl-bridged non-condensed alkyl multi-aromatic compounds. The reactor effluent stream contains one or more alkyl mono-aromatic compounds. The system also includes a first separator fluidly coupled to the hydrodearylation reactor and adapted to receive the reactor effluent stream and to produce a hydrodearylated gas stream and a hydrodearylated liquid stream. The system also includes a second separator fluidly coupled to the first separator and adapted to receive a portion of the hydrodearylated gas stream and to produce a hydrocarbon liquid stream and a vapor stream rich in hydrogen.Type: GrantFiled: July 11, 2018Date of Patent: May 21, 2019Assignee: SAUDI ARABIAN OIL COMPANYInventors: Bruce Richard Beadle, Vinod Ramaseshan, Rakan Sulaiman Bilaus, Omer R. Koseoglu, Robert P. Hodgkins
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Patent number: 10053401Abstract: Embodiments in the present disclosure describe a process for recovery of lighter mono-aromatic compounds from a stream containing alkyl bridged non-condensed alkyl multi-aromatic compounds by conversion to non-condensed alkyl mono-aromatic compounds. The process includes supplying, to a reactor, a hydrocarbon feedstock containing alkyl bridged non-condensed alkyl aromatic compounds and a hydrogen stream. The process further includes allowing the alkyl-bridged non-condensed alkyl multi-aromatic compounds to react with hydrogen in the presence of a suitable catalyst to produce alkyl mono-aromatic compounds. The process may include processing the alkyl mono-aromatic compounds to produce valuable products, such as para-xylene. Various other embodiments are disclosed and claimed.Type: GrantFiled: February 16, 2017Date of Patent: August 21, 2018Assignee: SAUDI ARABIAN OIL COMPANYInventors: Bruce Richard Beadle, Vinod Ramaseshan, Rakan Sulaiman Bilaus, Omer R. Koseoglu, Robert P. Hodgkins
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Patent number: 9233887Abstract: In a process for producing mono-cycloalkyl-substituted aromatic compound, benzene and cyclic monoolefin are contacted with a catalyst under alkylation conditions to produce an effluent containing mono-cycloalkyl-substituted aromatic compound. The catalyst comprises a molecular sieve.Type: GrantFiled: November 4, 2011Date of Patent: January 12, 2016Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Teng Xu, Edward A. Lemon, James R. Lattner, Jane C. Cheng
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Patent number: 9150783Abstract: Organic light emitting diodes (OLEds) are provided. In one embodiment, an OLED includes a first electrode, a second electrode and an organic layer positioned between the first and second electrodes. The organic layer comprises an organic metal complex represented by the formula [M(L)2]a, in which L is an anionic ligand, M is a metal that can be five-coordinated or six-coordinated with L, and a is an integer ranging from 2 to 4.Type: GrantFiled: April 13, 2007Date of Patent: October 6, 2015Assignee: Samsung Display Co., Ltd.Inventors: Kyung-Hoon Choi, Kwan-Hee Lee, Min-Seung Chun, Choon-Woo Lim
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Publication number: 20140212668Abstract: Provided are graphene nanoribbons (GNRs), methods of making GNRs, and uses of the GNRs. The methods can provide control over GNR parameters such as, for example, length, width, and edge composition (e.g., edge functional groups). The methods are based on a metal catalyzed cycloaddition reaction at the carbon-carbon triple bonds of a poly(phenylene ethynylene) polymer. The GNRs can be used in devices such a microelectronic devices.Type: ApplicationFiled: April 27, 2012Publication date: July 31, 2014Applicant: CORNELL UNIVERSITYInventors: William R. Dichtel, Hasan Arslan, Fernando J. Uribe-Romo
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Patent number: 8766023Abstract: A process for preparing a substituted or unsubstituted 9,10-diarylanthracene including reacting an organometallic substituted or unsubstituted aryl compound with a substituted or unsubstituted anthraquinone to yield a substituted or unsubstituted diol; and reacting the substituted or unsubstituted diol with a reducing agent to yield the substituted or unsubstituted 9,10-diarylanthracene is disclosed. An electroluminescent device comprising a light-emitting layer comprising the substituted or unsubstituted 9,10-diarylanthracene is also disclosed.Type: GrantFiled: July 20, 2005Date of Patent: July 1, 2014Assignee: LG Display Co., Ltd.Inventor: Jennifer A. Coggan
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Publication number: 20140163283Abstract: A method of carrying out Suzuki-Miyaura CC-coupling reactions, includes reacting an aryl halide with an aryl boronic acid in an organic solvent in the presence of an oxide supported palladium catalyst and a base, characterized in that the base is added in the form of an aqueous solution with a constant flow rate within a predetermined period of time at the beginning of the reaction.Type: ApplicationFiled: July 6, 2012Publication date: June 12, 2014Applicant: UNIVERSITE CATHOLIQUE DE LOUVAINInventors: Eric Gaigneaux, Marc Jacquemin, Damien Hauwaert, Caroline Cellier, Alain Merschaert, Raquel Mateos Blanco
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Patent number: 8722942Abstract: A method produces a biphenyl derivative, with an industrially high yield and excellent productivity, by use of a raw material which is low in cost and toxicity. The method for producing the biphenyl derivative represented by Formula (1) is characterized in that a chlorine atom in a benzene derivative represented by Formula (2) reacts with magnesium metal to convert the benzene derivative into a Grignard reagent, and then the Grignard reagent is subjected to a coupling reaction in the presence of a catalyst and a dichloropropane: (wherein A represents at least one selected from alkyl groups, alkoxy groups, alkoxymethyl groups, a vinyl group, phenyl groups and chlorine, and n represents an integer of 1 to 4).Type: GrantFiled: October 12, 2007Date of Patent: May 13, 2014Assignee: Toray Fine Chemicals Co., Ltd.Inventors: Tamio Hayashi, Jiro Nakatani
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Patent number: 8298683Abstract: The present invention provides an organic light emitting device comprising a first electrode, at least one organic layer and a second electrode, laminated successively, in which at least one layer of the organic layer has a polycyclic aromatic hydrocarbon as a core and comprises at least one of a derivative in which a substituted or unsubstituted C2-30 cycloalkane, or a substituted or unsubstituted C5-50 polycycloalkane is directly fused to the core or fused to a substituent of the core; and a new organic compound usable in the organic light emitting device. Furthermore, the present invention provides a charge carrier extracting, injecting or transporting material which has a polycyclic aromatic hydrocarbon as a core and comprises a derivative in which a substituted or unsubstituted C2-30 cycloalkane, or a substituted or unsubstituted C5-50 polycycloalkane is directly fused to the core or fused to a substituent of the core.Type: GrantFiled: September 14, 2006Date of Patent: October 30, 2012Assignee: LG Chem, Ltd.Inventors: Kong Kyeom Kim, Sung Kil Hong, Hye Young Jang, Dong Seob Jeong
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Publication number: 20120130113Abstract: The disclosure provides methods for the use of open metal frameworks to catalyze coupling reactions.Type: ApplicationFiled: July 27, 2010Publication date: May 24, 2012Applicants: BASF SE, THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: Omar M. Yaghi, Alexander U. Czaja, Bo Wang, Zheng Lu
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Publication number: 20110124755Abstract: The invention relates to a polyisocyanurate comprising isocyanurate rings linked by linker groups coupled to the nitrogen atoms of said rings. The polyisocyanurate may be microporous or mesoporous or both microporous and mesoporous.Type: ApplicationFiled: April 9, 2009Publication date: May 26, 2011Applicant: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCHInventors: Yugen Zhang, Jackie Y. Ying, Siti Nurhanna Binte Riduan
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Publication number: 20110077406Abstract: Embodiments of the invention provide methods and materials for chemical cross-coupling reactions that utilize unconventional phenol derivatives as cross-coupling partners. Embodiments of the invention can be used to synthesize a variety of useful organic compounds, for example the anti-inflammatory drug flurbiprofen.Type: ApplicationFiled: September 24, 2010Publication date: March 31, 2011Applicant: THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: Neil K. Garg, Kyle W. Quasdorf, Xia Tian
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Patent number: 7732652Abstract: The invention aims to provide a perylene derivative preparation process featuring satisfactory yields and improved preparation efficiency, a perylene derivative obtained by the process, and an organic EL device using the same.Type: GrantFiled: October 7, 2004Date of Patent: June 8, 2010Assignee: TDK CorporationInventors: Tetsuji Fujita, Kensuke Ara, Tetsushi Inoue
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Publication number: 20100001262Abstract: Disclosed in an anthracene derivative, an organic electronic device using the anthracene derivative, and an electronic apparatus including the organic electronic device. The anthracene derivative is capable of being used as a hole injecting material, a hole transporting material, an electron injecting material, an electron transporting material, and a light emitting material in an organic electronic device including an organic light emitting device. In particular, the anthracene derivative is capable of being used alone as a light emitting material and a host or a dopant in a host/dopant system. The organic electronic device is excellent in views of efficiency, driving voltage, life time, and stability.Type: ApplicationFiled: July 25, 2007Publication date: January 7, 2010Inventors: Ji-Eun Kim, Jae-Chol Lee, Hye-Young Jang, Tae-Yoon Park, Sung-Kil Hong, Jun-Gi Jang, Jin-Kyoon Park, Hyun Nam, Kong-Kyeom Kim, Yeon-Hwan Kim
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Patent number: 7385095Abstract: The present invention provides an indene derivatives having a new structure and an organic light-emitting diode using the same. The organic light-emitting diode according to the present invention shows improved effects in efficiency, driving voltage and stability.Type: GrantFiled: October 19, 2006Date of Patent: June 10, 2008Assignee: LG Chem, Ltd.Inventors: Dae Woong Lee, Jae Soon Bae, Dong Hoon Lee, Kong Kyeom Kim
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Patent number: 7247761Abstract: The present invention relates to a process for preparing aryl-aryl-coupled compounds and materials. These materials play an important role in industry, for instance as liquid crystals, pharmaceuticals, agrochemicals and as organic semiconductors. The aryl-aryl couplings hitherto carried out by means of Yamamoto coupling require specific additives in order to give a product suitable for the subsequent use. Particularly in the electronics industry, the Yamamoto coupling needs to meet particular requirements.Type: GrantFiled: August 20, 2003Date of Patent: July 24, 2007Assignee: Merck Patent GmbHInventors: Aurelie Falcou, Jochen Schwaiger, Andrea Ritter
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Patent number: 7102045Abstract: The invention relates to a method for carrying out CC-coupling reactions, in particular a Heck and Suzuki reaction, in the presence of supported palladium as the catalyst and a base in a monophase or multiphase solvent mixture. According to said method, palladium detaches itself from the support in a characteristic manner, is redeposited after the reaction and the quantity of palladium not deposited after the reaction is significantly lower than 5000 ppm, in relation to the palladium used.Type: GrantFiled: July 18, 2001Date of Patent: September 5, 2006Assignee: Degussa AGInventors: Jürgen Krauter, Jörg Pietsch, Peter Panster, Klaus Köhler, Roland Heidenreich
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Patent number: 6762330Abstract: Phosphine oxide and sulfoxide compounds were used with transition metals, preferably palladium and nickel, to produce biaryls, arylthiols, arylphosphine oxides and arylamines via cross-coupling reactions with aryl halides and arylboronic acids, aryl Grignard reagents, thiols, phosphine oxides or amines.Type: GrantFiled: July 6, 2001Date of Patent: July 13, 2004Assignee: E. I. du Pont de Nemours and CompanyInventor: George Y. Li
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Patent number: 6608212Abstract: The present invention provides a process for preparing a vinylaromatic compound comprising reacting an arylmetal reagent selected from arylmagnesium reagents and aryllithium reagents with a vinylphosphate in the presence of a palladium catalyst. The present invention also provides a process for preparing a vinylphosphate comprising reacting an enolizable ketone with a sterically hindered Grignard reagent and a halophosphate diester.Type: GrantFiled: June 4, 2002Date of Patent: August 19, 2003Assignees: Pfizer, Inc., DSM NVInventor: Joseph Miller
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Patent number: 6506953Abstract: There is described a process the hydroalkylation of an aromatic hydrocarbon, particularly benzene, to produce a cycloalkyl-substituted aromatic compound, particularly cyclohexylbenzene, comprising the step of contacting the aromatic hydrocarbon with hydrogen in the presence of a catalyst comprising MCM-68 and at least one metal having hydrogenation activity.Type: GrantFiled: January 24, 2000Date of Patent: January 14, 2003Assignee: ExxonMobil Oil CorporationInventors: Jane Chi-Ya Cheng, Ajit B. Dandekar, Michael Alan Steckel, Hye Kyung Cho Timken
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Patent number: 6462245Abstract: A method for polymerizing an alkyl-substituted aromatic compound comprises reacting the alkyl-substituted aromatic compound in the presence of a molecular sieve such that the aromatic compound polymerizes.Type: GrantFiled: April 6, 2001Date of Patent: October 8, 2002Assignee: British Nuclear Fuels plcInventor: Darren Frank Lee
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Patent number: 6417357Abstract: This invention relates to a novel, inventive process for the preparation of biphenyls or aromatic olefins by coupling reactions of the Suzuki coupling and Heck coupling type, using allylpalladium catalysts of the &mgr;-halo(triisopropylphosphine)(&eegr;3-allyl)palladium(II) type.Type: GrantFiled: September 14, 2000Date of Patent: July 9, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Michael Tinkl, Andreas Hafner
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Patent number: 6369265Abstract: This invention provides a process for conducting Kumada coupling reactions. The processes of the present invention make use of N-heterocyclic carbenes as ancillary ligands in Kumada couplings of aryl halides. A Kumada coupling can be carried out by mixing, in a liquid medium, at least one aryl halide, wherein the aryl halide has, directly bonded to the aromatic ring(s), at least one halogen atom selected from the group consisting of a chlorine atom, a bromine atom, and an iodine atom; at least one Grignard reagent; at least one metal compound comprising at least one metal atom selected from nickel, palladium, and platinum, wherein the formal oxidation state of the metal is zero or two; and at least one N-heterocyclic carbene.Type: GrantFiled: February 22, 2000Date of Patent: April 9, 2002Assignee: University of New Orleans Research & Technology FoundationInventors: Steven P. Nolan, Jinkun Huang, Mark L. Trudell, Chunming Zhang
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Patent number: 6291722Abstract: Phosphine oxide compounds were used with transition metals, preferably palladium and nickel, to produce biaryls and arylamines via cross-coupling reactions with aryl halides and arylboronic acids, aryl Grignard reagents or amines.Type: GrantFiled: June 26, 2000Date of Patent: September 18, 2001Assignee: E. I. du Pont de Nemours and CompanyInventor: George Yanwu Li
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Patent number: 6103919Abstract: A catalytic process for production of biphenyl and its derivatives by coupling of substituted or unsubstituted monoaryl compounds in the presence of a catalytic system comprising at least one Pd (II) compound and a strong acid or a mixture of acids. The process provides high conversions and high selectivity under mild temperature conditions and short reaction times. The strong acid or mixture of acids has a Hammett acidity of less than about -10, and contains a predominant amount of counterions which form a weak ligand complex with palladium (II). The method is highly selective to formation of desired biaryl isomers, such as 4,4'-isomers, and allows control of the relative amounts of isomers of biaryl compounds and substituted monoaryl compounds in the final product.Type: GrantFiled: July 7, 1998Date of Patent: August 15, 2000Assignee: Arteva North America S.A.R.L.Inventors: David Anthony Schiraldi, Sheldon Christopher Sherman, Dhiraj Sudesh Sood, Mark Gilmore White
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Patent number: 5869592Abstract: Rigid-rod macromonomers, and methods for preparing such macromonomers, having a polyaromatic backbone, solubilizing side groups, and reactive side groups are provided. The macromonomers are chemically incorporated into polymer systems to provide stronger, stiffened polymers.Type: GrantFiled: August 19, 1991Date of Patent: February 9, 1999Assignee: Maxdem IncorporatedInventors: Robert R. Gagne, Matthew Louis Marrocco III, Mark Steven Trimmer, Neil H. Hendricks
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Patent number: 5849967Abstract: Binderless zeolite L particles are prepared by a method in which particles are formed from silica and from 0 to 95 wt % preformed zeolite L crystallites, and the particles are thereafter reacted with an alkaline solution comprising a source of alumina to convert the silica binder to zeolite L. These particles may comprise cylindrical zeolite L crystallites with a mean diameter of at least 0.05 micron in a zeolite L matrix and may be used as catalyst. Also acyclic hydrocarbons are dehydrocyclized and/or isomerized by contacting them at a temperature of from 370.degree. C. to 600.degree. C. with this catalyst incorporating at least one Group VIII metal having dehydrogenating activity to convert at least part of the acyclic hydrocarbons into aromatic hydrocarbons.Type: GrantFiled: June 7, 1995Date of Patent: December 15, 1998Assignee: Exxon Chemical Patents Inc. (ECPI)Inventors: Johannes Petrus Verduijn, Pieter Ernst Gellings
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Patent number: 5786486Abstract: Acrylamide derivatives represented by General Formula (1) below: ##STR1## (One specific example of General Formula (1) is methyl (S,S)-3,3'-?3,3'-(1,4-phenylenediacryloyl)!-bis?1-chloromethyl-5-hydroxy-7 -triflouromethyl-1, 2,3,6-tetrahydropyrrolo?3,2-e!indole-8-carboxylate.)The acrylamide derivatives represented by General Formula (1) is highly selective to cancer cells, less toxic, and highly active also against solid tumor.Type: GrantFiled: May 13, 1997Date of Patent: July 28, 1998Assignees: Kyorin Pharmaceutical Co., Ltd., Sagami Chemical Research CenterInventors: Yasumichi Fukuda, Shigeki Seto, Yasuo Oomori, Hiroyuki Ebisu, Shiro Terashima
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Patent number: 5602228Abstract: Methods for coupling aryl halides or aryl sulfonates to produce biaryls or polyaryls using novel nickel phosphite catalysts are provided.Type: GrantFiled: June 6, 1995Date of Patent: February 11, 1997Assignee: Maxdem IncorporatedInventors: Ying Wang, Matthew L. Marrocco, III, Mark S. Trimmer
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Patent number: 5167795Abstract: A process for the production of olefins and aromatics from hydrocarbon feedstocks by catalytically cracking alone or cracking and dehydrogenating the hydrocarbons in the presence of an entrained stream of catalytic heat carrying solids at short residence times to preferentially produce olefins having three or more carbon atoms and/or to produce aromatics, especially benzene.Type: GrantFiled: September 6, 1991Date of Patent: December 1, 1992Assignee: Stone & Webster Engineering Corp.Inventor: Robert J. Gartside
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Patent number: 4885423Abstract: A process for preparation of an aromatic dimer compound corresponding to the structureIxAr-ArIxwherein x is 0, 1, 2, 3, 4, or 5 and Ar is a divalent aromatic radical containing 6 to 14 carbon atoms comprising contacting, at a sufficient temperature and pressure in the absence of carbon monoxide and in the absence of an alkali metal compound or an alkaline earth metal compound, platinum and an aromatic iodide compound corresponding to the structureAr-Ixwhere Ar is a monovalent aromatic radical and x is 1, 2, 3, 4, 5, or 6.Type: GrantFiled: May 11, 1989Date of Patent: December 5, 1989Assignee: Eastman Kodak CompanyInventor: Mark Rule
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Patent number: 4720576Abstract: A process for dehalogeno-dimerization reaction of an aromatic halide compound which comprises dimerizing aromatic halide compound having at least one halogen atom attached to a carbon atom in the aromatic nucleus, and optionally having a substituent other than the halogen atom, in the presence of a platinum group metal catalyst, carbon monoxide, and an alkali metal compound and/or an alkaline earth metal compound.Type: GrantFiled: September 18, 1986Date of Patent: January 19, 1988Assignee: Mitsubishi Chemical Industries LimitedInventors: Keisuke Wada, Keiichi Sato
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Patent number: 4675462Abstract: A process for the preparation of (2,2)-paracyclophane by conversion of p.methylbenzyltrimethylammonium halide to the corresponding hydroxide and by Hofmann elimination from p.methylbenzyltrimethylammonium hydroxide, wherein both reactions are carried out in the same aqueous solution of an alkaline hydroxide and in the presence of a copper or iron compound.Type: GrantFiled: October 29, 1986Date of Patent: June 23, 1987Assignee: Montedison S.p.A.Inventors: Raffaele Ungarelli, Maurizio A. Beretta, Loris Sogli
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Patent number: 4607116Abstract: Provided is a process for preparing a diaryl or a mixture of diaryls represented by any or a combination of the following formulae (II), (III) and (V), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted in a solvent in the presence of a transition metal catalyst and a reducing metal at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 -I.sup..sym. -Ar.sub.2 ]X.sup..crclbar. (I)Ar.sub.1 -Ar.sub.1 (II)Ar.sub.1 -Ar.sub.2 (III)Ar.sub.2 -Ar.sub.2 (IV)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups and X.sup..crclbar. is a counter ion which is inert to said reaction.Type: GrantFiled: March 8, 1984Date of Patent: August 19, 1986Assignee: Nippon Petrochemicals Company LimitedInventors: Yasuo Yamazaki, Takehiko Suzuki, Masaharu Uchiyama
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Patent number: 4581380Abstract: New 2,6-disubstituted derivatives of naphthalene have the formula ##STR1## wherein n is 1 or 2,R.sub.1 to R.sub.4 are hydrogen or CH.sub.3,R.sub.5 is ##STR2## (iv) 2-oxazolinyl, wherein m is 0 or 1, R.sub.6 is hydrogen, alkyl, OR.sub.9 wherein R.sub.9 is H, alkyl or ##STR3## wherein R.sub.10 is alkyl or aryl, or R.sub.6 is ##STR4## when m=1, r' and r" representing H, alkyl, mono- or poly-hydroxyalkyl, aryl or a heterocycle when taken together, R.sub.7 is H or alkyl, R.sub.8 is H, alkyl and the acetal of said compounds, and the salts of the compounds of formula I. These compounds are usefully employed in the pharmaceutical and cosmetic fields.Type: GrantFiled: November 28, 1984Date of Patent: April 8, 1986Assignee: Groupement Economique dite: Centre National de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
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Patent number: 4268699Abstract: Hydroalkylation of aromatic hydrocarbons using an acidic crystalline zeolite type support having ruthenium and nickel thereon, the nickel having been placed thereon responsive to correlation of hydroalkylation selectivity and the amount of alkali metal or alkaline earth metal ion removed from the support during cation exchange when preparing a catalyst. In one embodiment benzene is converted to cyclohexylbenzene.Type: GrantFiled: December 7, 1979Date of Patent: May 19, 1981Assignee: Phillips Petroleum CompanyInventors: Timothy P. Murtha, Ernest A. Zuech
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Patent number: 4219687Abstract: Mononuclear aromatic hydrocarbons, e.g. benzene and analogs, are converted by hydroalkylation to the corresponding cycloalkyl aromatics by contacting the mononuclear aromatic hydrocarbons in the presence of hydrogen with a catalyst comprising a rare earth-exchanged Y-type zeolite support carrying a promoter comprising at least one of ruthenium, iridium, rhodium and palladium, the catalyst being calcined in an oxygen-containing atmosphere at a temperature of 250.degree. to 600.degree. C. prior to the hydroalkylation reaction.Type: GrantFiled: July 26, 1978Date of Patent: August 26, 1980Assignee: Standard Oil CompanyInventors: Serge R. Dolhyj, Louis J. Velenyi
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Patent number: 4218572Abstract: Substituted or unsubstituted cyclohexylbenzene is dehydrogenated to substituted or unsubstituted biphenyl in the absence of oxygen over an oxide complex catalyst. The oxide complex catalyst comprises at least one element selected from the group consisting of Group VB and Group VIII elements, optionally promoted with at least one element selected from the group consisting of Group IA, Group IB, Group IIB, Group VIIB and Group VIB.Type: GrantFiled: September 28, 1978Date of Patent: August 19, 1980Assignee: Standard Oil CompanyInventors: Serge R. Dolhyj, Louis J. Velenyi
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Patent number: 4174447Abstract: A decarboxylation process for coupling aromatic compounds wherein cyclic hydrocarbons and heterocyclic compounds having at least one labile ring hydrogen are reacted with the mono silver salts of aromatic carboxylic acids, or mono silver salts of unsaturated compounds such as .alpha.,.beta.-ethylenically unsaturated acid compounds, or silver trifluoroacetate, or the mono silver salts are reacted with themselves, by heating to temperatures of 100.degree. to 500.degree. C. at pressures of 0.1 to 10 atmospheres, or by irradiating the reactants with ultraviolet light of 200 to 400 nanometers at temperatures of -30.degree. to 150.degree. C. The resulting dimers, trimers, polysubstituted polyphenyls, polyheterocyclics and trifluoromethylated aromatics are useful as heat transfer media, as intermediates for high molecular weight polymers, pesticides and petroleum additives, and as scintillation counters.Type: GrantFiled: February 26, 1975Date of Patent: November 13, 1979Assignee: Standard Oil Company (Indiana)Inventor: Ellis K. Fields
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Patent number: 4164518Abstract: The oxidative coupling of benzene or benzene derivatives to form the corresponding diphenyls, comprising contacting benzene or a benzene derivative, such as toluene, with molecular oxygen using as a catalyst .beta.-diketo complexes of palladium such as acetylacetone-palladium complex. Use of at least one zirconium compound such as zirconium oxystearate in conjunction with the catalyst gives an increased catalytic activity. The diphenyls are intermediates for production of dyestuffs, pharmaceuticals and other chemicals, and also find application in the preparation of high-molecular-weight polyesters and polyamides.Type: GrantFiled: October 14, 1977Date of Patent: August 14, 1979Assignee: Teijin LimitedInventors: Yataro Ichikawa, Teizo Yamaji