Using Al Halide Catalyst Patents (Class 585/459)
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Patent number: 8299310Abstract: Processes for conversion of lignin to products such as phenolic compounds and biofuels prepared from such phenolic compounds are disclosed and described. A process for conversion of a lignin material to bio-fuels can include subjecting the lignin material to a base catalyzed depolymerization reaction to produce a partially depolymerized lignin. The partially depolymerized lignin can then be subjected to a stabilization/partial hydrodeoxygenation reaction to form a partially hydrodeoxygenated product. Following partial hydrodeoxygenation, the partially hydrodeoxygenated product can be reacted in a hydroprocessing step to form a bio-fuel. Each of these reaction steps can be performed in single or multiple steps, depending on the design of the process. The production of an intermediate partially hydrodeoxygenation product and subsequent reaction thereof can significantly reduce or eliminate reactor plugging and catalyst coking.Type: GrantFiled: May 6, 2011Date of Patent: October 30, 2012Assignee: University of Utah Research FoundationInventors: Wlodzimierz W. Zmierczak, Jan D. Miller
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Patent number: 8288602Abstract: The present invention describes a cost-efficient method for preparing di-substituted fluorenes in high yield.Type: GrantFiled: March 28, 2007Date of Patent: October 16, 2012Assignee: Total Petrochemicals Research FeluyInventors: Alexander Z. Voskoboynikov, Artyom Y. Le Bedev, Andrey F. Asachenko, Abbas Razavi
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Publication number: 20110201863Abstract: This invention relates to a method wherein a high-purity paraxylene can be produced efficiently by using a catalyst having a molecular sieving action (or shape selectivity) and being excellent in the catalytic activity without isomerization and adsorption-separation steps. More particularly, it relates to a method of producing a high-purity paraxylene, characterized in that MFI type zeolite having a primary particle size of not more than 100 ?m, a structure defining agent and silica material having an average particle size of not less than 10 nm but less than 1.0 ?m are used as a starting material, and a synthetic zeolite catalyst produced by subjecting the MFI type zeolite to a coating treatment with an aqueous solution obtained by mixing so as to satisfy X×Y<0.05 (wherein X is a concentration of the silica material (mol %) and Y is a concentration of the structure defining agent (mol %)) is used in the alkylation or disproportionation of at least one of benzene and toluene as a starting material.Type: ApplicationFiled: September 29, 2009Publication date: August 18, 2011Applicant: JX NIPPON OIL & ENERGY CORPORATIONInventors: Koichi Matsushita, Chikanori Nakaoka, Norikazu Nishiyama
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Publication number: 20110178355Abstract: The present invention relates to a method and a reactor system for preparing linear alpha-olefins by oligomerization of ethylene in the presence of an organic solvent and an oligomerization catalyst, wherein a product fraction of C10+ alpha-olefins contaminated with aromatic C9+ compounds is separated from a product main stream and transferred into a conversion reactor, where C10+ alpha-olefins and aromatic C9+ components are reacted in the presence of a Friedel-Crafts alkylation catalyst to produce aromatic C19+ compounds.Type: ApplicationFiled: January 31, 2007Publication date: July 21, 2011Applicants: LINDE AG, SAUDI BASIC INDUSTRIES CORPORATIONInventors: Peter M. Fritz, Wolfgang Müller, Florian Winnkler
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Patent number: 7737312Abstract: This invention relates to a process for producing linear alkyl benzene, the process including the steps of obtaining a hydrocarbon condensate containing olefins, paraffins and oxygenates from a low temperature Fischer-Tropsch reaction; a) fractionating a desired carbon number distribution from the hydrocarbon condensate to form a fractionated hydrocarbon condensate stream; b) extracting oxygenates from the fractionated hydrocarbon condensate stream from step (a) to form a stream containing olefins and paraffins; c) combining the stream containing olefins and paraffins from step (b) with the feed stream from step (g) to form a combined stream; d) alkylating olefins in the combined stream from step (c) with benzene in the presence of a suitable alkylation catalyst in an alkylation reactor; e) recovering linear alkyl benzene from the alkylation reactor; f) recovering unreacted paraffins from the alkylation reactor; g) dehydrogenating the unreacted paraffins in the presence of a suitable dehydrogenation catalystType: GrantFiled: March 10, 2004Date of Patent: June 15, 2010Assignee: Sasol Technology (Proprietary) LimitedInventors: Ivan Greager, Jan Hendrik Scholtz, Johan Pieter de Wet, Mieke Ann Desmet, Wilhelmina Jansen, Paul Jacobson, Luis Pablo Fidel Dancuart
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Publication number: 20090036722Abstract: A process is described for producing an alkylaromatic compound, in which a first feed comprising an alkylatable aromatic compound and a second feed comprising an alkene are introduced into a first alkylation reaction zone comprising a first alkylation catalyst. The first alkylation reaction zone is operated under conditions effective to cause alkylation of the alkylatable aromatic compound by the alkene to produce said alkylaromatic compound, the conditions being such that the alkylatable aromatic compound is at least predominantly in the vapor phase. A first effluent comprising the alkylaromatic compound and unreacted alkylatable aromatic compound is withdrawn from the first alkylation reaction zone and at least part of the unreacted alkylatable aromatic compound is treated to remove catalyst poisons therefrom and produce a treated unreacted alkylatable aromatic stream.Type: ApplicationFiled: July 30, 2007Publication date: February 5, 2009Inventors: Michael C. Clark, Vijay Nanda, Maruti Bhandarkar, Joseph C. Peters, Chung-Ming Chi, Brian Maerz
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Publication number: 20090005622Abstract: Methods and systems for the production of linear alkylbenzens are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and mixing of one or more olefins (e.g. propylene) with an aromatic. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time with existing catalysts.Type: ApplicationFiled: June 23, 2008Publication date: January 1, 2009Applicant: H R D CORPORATIONInventors: Abbas HASSAN, Ebrahim BAGHERZADEH, Rayford G. ANTHONY, Gregory BORSINGER, Aziz HASSAN
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Patent number: 7297827Abstract: Disclosed is an alkylation reactor for preparing ethylbenzene. The reactor comprises a monolith catalyst system that includes a monolith support impregnated or co-formed with a catalyst suitable to catalyze the alkylation of benzene with ethylene. The catalyst may be selected from, for example, zeolites such as beta zeolite and MCM-22 zeolite, and fixed super acids. Also disclosed is a method of preparing ethylbenzene by alkylating a mixture of benzene and ethylene in an alkylation reactor comprising a monolith catalyst system, including a monolith support impregnated or co-formed with a suitable catalyst. In one embodiment the invention provides a convenient means of upgrading an existing reactor that has previously been used for conventional liquid phase alkylations such as those catalyzed by aluminum trichloride. The inventive alkylation method may be effectively and advantageously carried out under critical or near critical conditions, if desired.Type: GrantFiled: November 29, 2004Date of Patent: November 20, 2007Assignee: Fina Technology, Inc.Inventor: Kevin Kelly
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Patent number: 7294420Abstract: A method of producing hydrogen for a fuel cell from a hydrocarbon fuel composition, by providing a hydrocarbon fuel composition, which is obtained by contacting a liquid hydrocarbon feed comprising an alkylating agent with an acidic catalyst, under conditions effective to alkylate at least a portion of the hydrocarbon feed; converting the hydrocarbon fuel composition into hydrogen; and optionally, introducing the hydrogen produced into a fuel cell. In a preferred embodiment the liquid hydrocarbon feed further comprises sulphur-containing impurities, at least a portion of which are alkylated during the alkylation step.Type: GrantFiled: August 28, 2002Date of Patent: November 13, 2007Assignee: BP P.L.C.Inventor: Michael Graham Hodges
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Patent number: 7148388Abstract: In a process for preparing an olefinic hydrocarbon mixture comprising at least 5% by weight of mono-olefin oligomers of the empirical formula: CnH2n where n is greater than or equal to 6, a feedstock comprising n-butene and propylene in a molar ratio of about 1:0.01 to about 1:0.49 is contacted under oligomerization conditions with surface deactivated ZSM-23. The resultant mono-olefin oligomers comprise at least 20 percent by weight of olefins having at least 12 carbon atoms, wherein said olefins having at least 12 carbon atoms have an average of from about 0.8 to about 2.0 C1–C3 alkyl branches per carbon chain.Type: GrantFiled: March 28, 2003Date of Patent: December 12, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen W. Beadle, Cesar M. Cheng-Guajardo, Carolyn B. Duncan, David Wayne Turner, Ramzi Y. Saleh
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Patent number: 6787438Abstract: A microelectromechanical device is provided which includes a contact structure interposed between a pair of electrodes arranged beneath a beam. In some embodiments, the device may include additional contact structures interposed between the pair of electrodes. For example, the device may include at least three contact structures between the pair of electrodes. In some embodiments, the beam may be suspended above the pair of electrodes by a support structure affixed to a first end of the beam. Such a device may further include an additional support structure affixed to a second end of the beam. In some cases, the device may be adapted to pass a signal from the first end to the second end of the beam. In addition or alternatively, the device may be adapted to pass the signal between one or both ends of the beam and one or more of the contact structures.Type: GrantFiled: October 16, 2001Date of Patent: September 7, 2004Assignee: Teravieta Technologies, Inc.Inventor: Richard D. Nelson
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Patent number: 6303840Abstract: A process for the alkylation of aromatic substrates under supercritical or near-critical reaction conditions is described. In particular, a method for performing Friedel-Crafts alkylation reactions is disclosed under those conditions. Friedel-Crafts reactions may be effected using a heterogeneous catalyst in a continuous flow reactor containing a supercritical or near-critical reaction medium. Selectivity of product formation can be achieved by varying one or more of temperature, pressure, catalyst, flow rates and also by varying the ratios of aromatic substrate to alkylating agent.Type: GrantFiled: June 18, 1999Date of Patent: October 16, 2001Assignee: Thomas Swan & Co., LimitedInventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland, Fiona Ruth Smail
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Patent number: 6218591Abstract: The present invention relates to new crystalline zeolite SSZ-36 prepared using a cyclic or polycyclic quaternary ammonium cation templating agent.Type: GrantFiled: June 11, 1999Date of Patent: April 17, 2001Assignee: Chevron U.S.A. Inc.Inventors: Gregory S. Lee, Stacey I. Zones, Yumi Nakagawa, Susan T. Evans
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Patent number: 6096680Abstract: Liquid clathrate compositions useful as reusable aluminum catalysts in Friedel-Crafts reactions are described. In one embodiment, the liquid clathrate composition is formed from constituents comprising (i) at least one aluminum trihalide, (ii) at least one salt selected from alkali metal halide, alkaline earth metal halide, alkali metal pseudohalide, quaternary ammonium salt, quaternary phosphonium salt, or ternary sulfonium salt, or a mixture of any two or more of the foregoing, and (iii) at least one aromatic hydrocarbon compound.Type: GrantFiled: April 22, 1998Date of Patent: August 1, 2000Assignee: Albemarle CorporationInventor: Won S. Park
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Patent number: 6010617Abstract: A process for reducing the mutagenicity of a coal-tar-based product containing polynuclear aromatic compounds. The process includes the step of contacting the coal-tar-based product in the presence of an alkylating agent with an acid catalyst under alkylation conditions sufficient to reduce the mutagenicity of the polynuclear aromatic containing coal-tar-based material to a level less than the initial mutagenicity index value. Also provided are non-carcinogenic coal-tar-derived products.Type: GrantFiled: June 6, 1994Date of Patent: January 4, 2000Assignee: Mobil Oil CorporationInventors: Carl R. Mackerer, Timothy A. Roy, Gary R. Blackburn
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Patent number: 5994602Abstract: This invention relates to a process for the alkylation of aromatics by reacting an aromatic hydrocarbon with an olefin in the presence of an ionic liquid comprising (a) a compound of the formula R.sub.n MX.sub.3-n wherein R is a C1-C6 alkyl radical, M is aluminium or gallium, X is a halogen atom and n is 0, 1 or 2 and, (b) a hydrocarbyl substituted imidazolium halide or a hydrocarbyl substituted pyridinium halide wherein at least one of the said hydrocarbyl substituents in the imidazolium halide is an alkyl group having 1-18 carbon atoms. The process allows ready separation of reaction products from the ionic liquid and improves selectivity to alkylated products.Type: GrantFiled: July 29, 1997Date of Patent: November 30, 1999Assignee: BP Chemicals LimitedInventors: Ala'a K Abdul-Sada, Martin Philip Atkins, Brian Ellis, Philip Kenneth Gordon Hodgson, Mark Louis Michael Morgan, Kenneth Richard Seddon
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Patent number: 5986155Abstract: Treating low reactivity alkylating agents in the vapor phase with catalysts converts the low reactivity alkylating agents to high reactivity alkylating agents. The alkylating agents are useful in synthesis of alkyl aromatics with Lewis acid catalysts.Type: GrantFiled: July 10, 1996Date of Patent: November 16, 1999Assignee: The Lubrizol CorporationInventors: James D. Burrington, Stuart L. Bartley, Douglas C. Rhubright, Paul A. Lewis, Marvin B. DeTar, Alicia L. Kliever, Frank A. Del Greco, Lawrence T. Novak
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Patent number: 5977422Abstract: This invention relates to an improved catalytic process for the alkylation of benzene or substituted benzene with alkyl halides for the continuous production of diarylalkanes or substituted derivatives thereof using ethylaluminum dichloride or methylaluminum dichloride as an organoaluminum dichloride catalyst. A process and apparatus are provided for reacting either benzene (or a substituted benzene compound) together with either an alkyl halide or an aromatic halide.Type: GrantFiled: June 9, 1997Date of Patent: November 2, 1999Assignee: The Dow Chemical CompanyInventors: Steven A. Costello, Douglas L. Potts, Randall F. Pogue
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Patent number: 5962760Abstract: A process for the alkylation of aromatic compounds with an olefin or alkyl halide having from 1 to 24 carbon atoms utilizes a novel catalyst comprising: a) a refractory inorganic oxide, b) the reaction product of a first metal halide and bound surface hydroxyl groups of the refractory inorganic oxide, c) a second metal cation, and d) optionally a zerovalent third metal. The refractory inorganic oxide is selected from the group consisting of alumina, titania, zirconia, chromia, silica, boria, silica-alumina, and combinations thereof and the first metal halide is a fluoride, chloride, or bromide of aluminum, gallium, zirconium, or boron. The second metal cation is selected from the group consisting of: monovalent metal cations in an amount from 0.0026 up to about 0.20 gram atoms per 100 grams refractory inorganic oxide for lithium, potassium, cerium, rubidium, silver, and copper, and from 0.012 to about 0.20 gram atoms for sodium; and alkaline earth metal cations in an amount from about 0.0013 up to about 0.Type: GrantFiled: August 4, 1997Date of Patent: October 5, 1999Assignee: UOP LLCInventors: Joseph A. Kocal, Anil R. Oroskar
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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: 5859302Abstract: Described are novel processes which employ reusable aluminum catalysts in Friedel-Crafts reactions.Type: GrantFiled: October 28, 1996Date of Patent: January 12, 1999Assignee: Albemarle CorporationInventor: Won S. Park
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Patent number: 5824832Abstract: A low temperature molten ionic liquid composition comprising a mixture of a metal halide and an alkyl-containing amine hydrohalide salt can be used in linear alkylbenzene formation. The metal halide is a covalently bonded metal halide which can contain a metal selected from the group comprised of aluminum, gallium, iron, copper, zinc, and indium, and is most preferably aluminum trichloride. The alkyl-containing amine hydrohalide salt may contain up to three alkyl groups, which are preferably lower alkyl, such as methyl and ethyl.Type: GrantFiled: March 27, 1997Date of Patent: October 20, 1998Assignee: Akzo Nobel NVInventors: Fawzy G. Sherif, Lieh-Jiun Shyu, Carl C. Greco
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Patent number: 5648580Abstract: A supported Lewis acid catalyst system for catalyzing hydrocarbon conversion reactions including cationic polymerization, alkylation, isomerization and cracking reactions is disclosed, wherein the catalyst system comprises an inorganic oxide support having immobilized thereon at least one relatively strong Lewis acid and at least one relatively weak Lewis acid.Type: GrantFiled: September 4, 1996Date of Patent: July 15, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Frank Joung-yei Chen, Christophe Le Deore, Roger Spitz, Alan Guyot
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Patent number: 5574198Abstract: The present invention relates to an improved process for preparing linear alkylbenzenes falling within such range as used in detergency (C.sub.10 -C.sub.14), which process consists of alkylating aromatic hydrocarbons (above all, benzene) with n-olefins in the presence of AlCl.sub.3, wherein said n-olefins are obtained by dehydrogenating n-paraffins.Type: GrantFiled: April 10, 1995Date of Patent: November 12, 1996Assignee: Enichem Augusta S.p.A.Inventors: Pierino Radici, Pierluigi Cozzi, Giuseppe Giuffrida, Agostino Zatta
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Patent number: 5488193Abstract: A process for reducing the mutagenicity of a polynuclear aromatic containing material containing from three to seven fused aromatic rings, especially a hydrocarbon refinery stream. The process reduces the initial mutagenicity index to a lower value by alkylating the compound with an alkylating agent which introduces an alkyl substituent having from three to five carbon atoms into the aromatic compound in the presence of an acid catalyst under alkylation conditions.Type: GrantFiled: January 25, 1995Date of Patent: January 30, 1996Assignee: Mobil Oil CorporationInventors: Carl R. Mackerer, Timothy A. Roy, Gary R. Blackburn
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Patent number: 5481054Abstract: Immobilized Lewis Acid catalyst comprising polymer having at least one Lewis Acid immobilized within the structure therein, said polymer having monomer units represented by the structural formula:--[A].sub.a --[B].sub.b --[C].sub.c --whereina represents about 1 to about 99 mole %b represents about 0 to about 50 mole %c represents about 1 to about 99 mole %a+b+c is preferably about 100%; ##STR1## C is selected from the group consisting of: ##STR2## (III) combinations thereof, wherein D is OH, halide, OR.sup.4, NH.sub.2, NHR.sup.3, OM', or OM";E is the residue of the reaction of at least one Lewis Acid with the D substituent of monomer unit B;R.sup.1 represents proton, C.sub.1 -C.sub.24 alkyl group, or C.sub.3 -C.sub.24 cycloalkyl;R.sup.2 represents C.sub.1 -C.sub.24 alkylene group, C.sub.3 -C.sub.24 cycloalkylene, C.sub.6 -C.sub.18 arylene, or C.sub.7 -C.sub.30 alkylarylene;R.sup.3 represents C.sub.1 -C.sub.24 alkyl, C.sub.3 -C.sub.24 cycloalkyl, C.sub.1 -C.sub.24 aryl, or C.sub.7 -C.sub.30 alkylaryl;R.sup.Type: GrantFiled: March 3, 1995Date of Patent: January 2, 1996Assignee: Exxon Chemical Patents Inc.Inventors: Tze-Chiang Chung, Frank J. Chen, Jon E. Stanat, Alok Kumar
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Patent number: 5476977Abstract: 1,1,2,3,4,4,6-Heptamethyl-1,2,3,4-tetrahydronaphthalene, a novel naphthalenic compound, is useful as an intermediate for the preparation of 5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarbaldehyde. It is prepared by a process consisting of the addition of an olefin of formula ##STR1## wherein R.sup.1 and R.sup.2 represent different substituents and each defines a hydrogen atom or a methyl radical, with p-cymene. 4,4-Dimethyl-2-pentene [compound (III): R.sup.1 =CH.sub.3 ; R.sup.2 =H] is obtained by the co-metathesis reaction of an olefin of formula ##STR2## wherein R.sup.1 and R.sup.2 represent identical substituents designating each a hydrogen atom or a methyl radical, with an olefin of formula ##STR3## wherein R.sup.3 and R.sup.4 identical or different, designate each a hydrogen atom or a methyl radical in the presence of an appropriate catalyst consisting of Re.sub.2 O.sub.7 on an inert solid carrier, or of WCl.sub.6 /(C.sub.2 H.sub.5))/Bu.sub.4 Sn.Type: GrantFiled: August 5, 1994Date of Patent: December 19, 1995Assignee: Firmenich SAInventors: Jean-Paul Leresche, Yves Mentha
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Patent number: 5430015Abstract: A method of acetylating 1,2,3,4,-tetrahydro-1,1,2,4,4,7-hexamethylnapthalene (HMT) to produce 6-acetyl-1,2,3,4-tetrahydro-1,1,2,4,4,7-hexamethlnaphthalene (acetyl-HMT), comprises subjecting a mixture of 1,2,3,4-tetrahydro-1,1,2,4,4,7-hexamethlnaphthalene and or one or more substituted indanes or substituted acetylindanes to a Friedel-Crafts acetylation reaction in the presence of a saturated hydrocarbon solvent.Type: GrantFiled: March 16, 1993Date of Patent: July 4, 1995Assignee: Unilever Patent Holdings, BVInventors: Christopher P. Newman, Karen J. Rossiter, Terence L. Miller
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Patent number: 5386072Abstract: Process for the preparation of linear alkylbenzenes, wherein the benzene is reacted, in the presence of aluminum chloride or aluminum in powder form, with a mixture composed of C.sub.7 -C.sub.20 n-olefins and C.sub.7 -C.sub.20 chloroparaffins, with a molar ratio n-olefins/chloroparaffins between 70:30 and 99:1.Type: GrantFiled: January 29, 1993Date of Patent: January 31, 1995Assignee: Enichem Augusta S.p.A.Inventors: Pierluigi Cozzi, Giuseppe Giuffrida, Tullio Pellizzon, Pierino Radici
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Patent number: 5210353Abstract: A process is provided for transaralkylating a class of starting compounds comprised of aryl-substituted lower alkanes and aryl-substituted fused alkylene ring compounds to produce derivatives of such compounds wherein benzyl substituents thereof have different alkyl substituents compared to the starting compounds. The process is carried out by admixing such a starting compound with a lower alkyl-substituted aromatic compound under liquid phase conditions in the presence of a catalytically effective amount of a Friedel-Crafts catalyst. The process makes possible new and economical routes for synthesizing desired lower alkyl-substituted benzyl group containing compounds, such as 2,2-di(lower alkyl-substituted) phenyl propanes and 1,3,3-trimethyl-1-(lower alkyl-substituted)-phenyl indans. Thus, there is provided a three-step process for making dixylylpropane from alpha methyl styrene and also a two-step process for making 1,3,3,6-tetramethyl-1-o-xylyl indan from alpha-4-dimethyl styrene.Type: GrantFiled: November 30, 1990Date of Patent: May 11, 1993Assignee: Amoco CorporationInventors: Carl A. Udovich, E. William Breder, Jr., Ibrahim Ghanayem, Mark W. Meszaros, Thomas E. Nemo, Thomas G. Smith
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Patent number: 5191136Abstract: A process for production of sec-butylbenzene is disclosed, comprising reacting benzene and n-butene in the presence of a liquid aluminum chloride complex catalyst is disclosed, wherein the reaction is carried out under conditions satisfying formulae (1) to (4):40>C.times.T.times.2.sup.(K-20)/10 > (1)C.ltoreq.0.9 (2)T.ltoreq.0.7 (3)K.gtoreq.80 (4)wherein C is a concentration (% by weight) of a complex catalyst in the reaction mixture; T is a reaction time (hr); and K is a reaction temperature (.degree.C). sec-Butylbenzene is produced in high yield while suppressing the amount of isobutylbenzene formed as a by-product.Type: GrantFiled: September 9, 1991Date of Patent: March 2, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Kazuteru Takahashi, Yasuhiko Higashio
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Patent number: 5132478Abstract: Aromatic compounds are alkylated with C.sub.20 -C.sub.1300 olefinic oligomers using an acidic alkylation catalyst to produce alkylated aromatic products, usually alkylaromatic hydrocarbons. The olefinic oligomers used as alkylating agents are prepared from 1-alkene oligomerization in contact with reduced metal oxide catalyst, preferably reduced chromium oxide on a silica support. The alkylated aromatic hydrocarbons retain the unique features of the alkylating olefinic oligomer and exhibit high viscosity index and low pour point. If the alkylation is carried out under certain combinations of conditions, especially using a Lewis acid catalysts such as aluminum trichloride and at higher temperatures, the alkyl portion of the product will undergo isomerization. The alkylaromatic compositions show improved thermal stability and are useful as lubricant basestocks and additives for improved antiwear properties, antioxidant and other properties.Type: GrantFiled: December 19, 1990Date of Patent: July 21, 1992Assignee: Mobil Oil CorporationInventors: Suzzy C. Ho, Margaret M. Wu
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Patent number: 5087785Abstract: Improved processes for the production of secondary alkyl indanes, particularly mixtures of 1,1,3,5-tetramethyl-3-isopropylindanes and 1,3,3,5-tetramethyl-3-isopropylindane, and alkylated tetrahydronaphthalenes, particularly mixtures of 1,1,3,4,4,6-hexametyl-1,2,3,4-tetrahydronaphthalene and 1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene, are described. In the processes of the invention, alkylated tetrahydronaphthalenes or secondary alkyl indanes are isomerized in the presence of a Lewis acid and a solvent which may be a halogenated or unhalogenated solvent and, optionally, a phase transfer agent, to produce, in the case of an alkylated tetrahydronaphthalene starting material, a secondary alkyl indane, and in the case of a secondary alkyl indane starting material, an aklylated tetrahydronaphthalene. The Lewis acid is present in the reaction medium in an amount of less than about 50 mole percent based on the amount of the alkylated tetrahydronaphthalene or secondary alkylindane charged.Type: GrantFiled: December 3, 1990Date of Patent: February 11, 1992Assignee: Union Camp CorporationInventor: Walter C. Frank
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Patent number: 5059736Abstract: A process for production of sec-butylbenzene from benzene and n-butene in the presence of a liquid aluminum chloride complex catalyst is disclosed, wherein the amount of aluminum chloride used as a component of the complex catalyst is from 0.3 to 5 wt % of the benzene used, the reaction temperature is from 20.degree. to 90.degree. C., and the weight ratio of isobutylbenzene formed as a by-product to sec-butylbenzene formed is not more than 0.01:1.Type: GrantFiled: April 24, 1990Date of Patent: October 22, 1991Assignee: Sumitomo Chemical Co., Ltd.Inventors: Mitsuhisa Tamura, Kazuhiro Yamauchi, Yasuhiko Higashio, Kazuteru Takahashi
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Patent number: 4943668Abstract: A process for producing an alkylated aromatic product having high selectivity to the thermodynamically preferred isomer by contacting meta-xylene and a C.sub.13 to C.sub.20 alpha-olefinic compound at a reaction temperature of about 40.degree. to about 80.degree. C. in the presence of a catalyst comprising an aluminum halide and elemental iodine.Type: GrantFiled: August 29, 1988Date of Patent: July 24, 1990Assignee: Phillips Petroleum CompanyInventor: Michael S. Matson
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Patent number: 4913178Abstract: Disclosed is a process for removing polychlorinated biphenyls from electrical apparatus, particularly transformers, to achieve concentration levels of 50 ppm or less as required by the EPA. A dielectric fluid having a relatively low boiling point as compared to polychlorinated biphenyls and other contaminants and in which PCB's are soluble is selected. There is an external cooling loop through which the dielectric fluid is circulated maintaining the temperature and pressure of the transformer within its design limits. There is an external distillation loop where the liquid removed from the transformer is heated to boiling point of the selected dielectric fluid thereby vaporizing the dielectric fluid and leaving the polychlorinated biphenyls in liquid phase in the distillation vessel. The dielectric fluid vapor is then condensed and returned to solubilize remaining PCB's in the transformer.Type: GrantFiled: August 18, 1988Date of Patent: April 3, 1990Assignee: Quadrex HPS Inc.Inventor: David E. Fowler
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Patent number: 4877915Abstract: A process is disclosed for the production of polyalkyl tetrahydronaphthalenes wherein a cyclialkylation reaction between an olefinic compound of the general formula ##STR1## wherein R.sup.4, R.sup.5, and R.sup.6 are substituents which do not interfere with a Friedel-Crafts-type reaction and R.sup.5 and R.sup.6 are other than H, and a substituted benzene compound is carried out in the presence of a hydride abstracting reagent, a Lewis acid, and, optionally, a phase transfer agent. In some embodiments, the subject process is specifically carried out in the absence of elemental iodine. The subject process produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using better, more convenient or less expensive process methodology than many processes known heretofore.Type: GrantFiled: January 27, 1989Date of Patent: October 31, 1989Assignee: Union Camp CorporationInventor: Walter C. Frank
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Patent number: 4877911Abstract: A process for the production of polyalkyl tetrahydronaphthalenes is disclosed wherein a cyclialkylation reaction between an olefinic compound of the general Formula ##STR1## wherein R.sup.5, R.sup.6 and R.sup.7 are independently defined and each is a substituent which does not interfere with a Friedel-Crafts type alkylation reaction, and a substituted benzene compound is carried out in the presence of an alkyl halide, a Lewis acid and a phase transfer agent. The subject process, which may be practiced in an unhalogenated hydrocarbon solvent, produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using safer solvents and better, more convenient, or less expensive process methodology than many processes known heretofore.Type: GrantFiled: January 27, 1989Date of Patent: October 31, 1989Assignee: Union Camp CorporationInventor: Walter C. Frank
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Patent number: 4877914Abstract: A process is disclosed for the production of polyalkyl tetrahydronaphthalenes is disclosed wherein a cyclialkylation reaction between an olefinic compound of the general Formula ##STR1## wherein R.sup.4, R.sup.5 and R.sup.6 are independently defined and each represents a substituent which does not interfere substantially in Friedel-Crafts type reactions and R.sup.5 and R.sup.6 are other than H, and a substituted benzene compound is carried out in the presence of an alkyl halide, a Lewis acid and a phase transfer agent. The subject process produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using better, more convenient, or less expensive process methodology than many processes known heretofore.Type: GrantFiled: January 27, 1989Date of Patent: October 31, 1989Assignee: Union Camp CorporationInventor: Walter C. Frank
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Patent number: 4877913Abstract: A process is disclosed for the production of polyalkyl tetrahydronaphthalenes wherein a cyclialkylation reaction between an olefinic compound of the general formula ##STR1## and a substituted benzene compound is carried out in the presence of a hydride abstracting reagent, a Lewis acid, and, optionally, a phase transfer agent. In some embodiments, the subject process is specifically carried out in the absence of elemental iodine. The subject process, which may be practiced in an unhalogenated hydrocarbon solvent, produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using better, more convenient or less expensive process methodology than many processes known heretofore.Type: GrantFiled: January 27, 1989Date of Patent: October 31, 1989Assignee: Union Camp CorporationInventor: Walter C. Frank
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Patent number: 4877910Abstract: A process is disclosed for the production of polyalkyl tetrahydronaphthalenes is disclosed wherein a cyclialkylation reaction between an olefinic compound of the general Formula ##STR1## wherein R.sup.4, R.sup.5, and R.sup.6 are independently defined and each represents a substituent which does not substantially interfere with a Friedel-Crafts type reaction and where R.sup.5 and R.sup.6 are other than H, and a substituted benzene compound is carried out in the presence of a hydride abstracting reagent, an alkyl halide or hydrogen halide, a Lewis acid, and, optionally, a phase transfer agent. In some embodiments, the subject process is specifically carried out in the absence of elemental iodine. The subject process produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using better, more convenient, or less expensive process methodology than many processes known heretofore.Type: GrantFiled: January 27, 1989Date of Patent: October 31, 1989Assignee: Union Camp CorporationInventor: Walter C. Frank
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Patent number: 4877916Abstract: A process is disclosed for the production of polyalkyl tetrahydronaphthalenes wherein a cyclialkylation reaction between an olefinic compound of the general formula ##STR1## where R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are independently defined and each is a substituent which does not interfere substantially with a Friedel-Crafts reaction, and a substituted benzene compound is carried out in the presence of a hydride abstracting reagent, an alkyl halide or hydrogen halide, a Lewis acid, and, optionally, a phase transfer agent. In some embodiments, the subject process is specifically carried out in the absence of elemental iodine. The subject process, which may be practiced in an unhalogenated hydrocarbon solvent, produces the desired compounds in a surprisingly high yield, with a surprisingly high selectivity to the desired product, and at a relatively high rate of reaction, using better, more convenient or less expensive process methodology than many processes known heretofore.Type: GrantFiled: January 27, 1989Date of Patent: October 31, 1989Assignee: Union Camp CorporationInventor: Walter C. Frank
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Patent number: 4877912Abstract: A process is disclosed for the production of 1,1,3,4,4,6-Hexamethyl-1,2,3,4-Tetrahydronaphthalene comprising reacting para-cymene with an olefinic compound selected from the group consisting of 2,3-dimethyl-1-butene and neohexene, in the presence of a reagent of the formula ##STR1## and further in the presence of an aluminum halide and I.sub.2, wherein in the above formula, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, independently, are H or a C.sub.1 -C.sub.3 straight chain, or branched alkyl, provided that no more than one of R.sup.1, R.sup.2 and R.sup.3 are H, and no more than one of R.sup.4, R.sup.5 and R.sup.6 are H.The subject process produces the desired compound in a surprisingly high yield, with a surprisingly high selectivity, and at a relatively high rate of reaction, using better, more convenient and/or less expensive process methodology than many processes known heretofore.Type: GrantFiled: January 27, 1989Date of Patent: October 31, 1989Assignee: Union Camp CorporationInventor: Walter C. Frank
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Patent number: 4734528Abstract: The present invention provides a method for preparing 3-ethylbenzophenone in a high purity which comprises the steps of alkylating benzene with ethylene in the presence of an alkylating catalyst to obtain an alkylated product composed mainly of unreacted benzene, ethylbenzene, polyethylbenzenes and heavier substances; subjecting the alkylated product to rectification in order to recover therefrom a fraction which has a temperature range of boiling points within the range of 275.degree. to 310.degree. C.Type: GrantFiled: September 8, 1986Date of Patent: March 29, 1988Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Atsushi Sato
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Patent number: 4731483Abstract: The present invention provides a method for preparing 3-ethylbenzophenone in a high purity which comprises the steps of alkylating benzene with ethylene with the aid of an alkylating catalyst to obtain an alkylated product composed mainly of unreacted benzene, ethylbenzene, polyethylbenzenes and heavier by-products; subjecting the alkylated product to distillation in order to recover therefrom a fraction which has a temperature range of boiling points within the range of 275.degree. to 310.degree. C. (in terms of atmospheric pressure); dehydrogenating the recovered fraction at a reaction temperature within the range of 200.degree. to 700.degree. C.Type: GrantFiled: September 8, 1986Date of Patent: March 15, 1988Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Shigenobu Kawakami, Atsushi Sato
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Patent number: 4714794Abstract: A synthetic oil having excellent oxidation stability, comprising a mixture of monoalkylnaphthalenes which have each a secondary alkyl group of 6 to 24 carbon atoms and in which the specific molar ratio of .alpha.- to .beta.-substituted monalkylnaphthalenes is at least 1.0. The synthetic oil is useful as a thermal medium oil or as the main component of a synthetic lubricating oil.Type: GrantFiled: May 15, 1987Date of Patent: December 22, 1987Assignee: Nippon Oil Co., Ltd.Inventors: Toshio Yoshida, Harumichi Watanabe
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Patent number: 4668835Abstract: The alkylation of para-substituted isopropyl benzenes with dipentenes employing an aluminum halide catalyst system produces novel tetracyclic compounds.Type: GrantFiled: October 4, 1985Date of Patent: May 26, 1987Assignee: Phillips Petroleum Co.Inventor: Raymond L. Cobb
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Patent number: 4665275Abstract: A thermal medium oil comprising at least one monosubstituted naphthalene derivative such as .beta.-(1,1-dimethyloctyl) naphthalene, .beta.-(1,1-dimethylhexyl) naphthalene and 2-t.-amylnaphthalene.Type: GrantFiled: June 17, 1985Date of Patent: May 12, 1987Assignee: Nippon Oil Co., Ltd.Inventors: Toshio Yoshida, Harumichi Watanabe
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Patent number: 4599472Abstract: Hydrocarbon solutions containing iodine or iodine-containing impurities are rendered essentially color-free by distillation in the presence of small amounts of a hydrocarbon soluble organometallic compound.Type: GrantFiled: June 27, 1985Date of Patent: July 8, 1986Assignee: Phillips Petroleum CompanyInventor: Raymond L. Cobb
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Patent number: 4551573Abstract: The alkylation of aromatic compounds with olefinic compounds is catalyzed by catalyst consisting essentially of aluminum halide and elemental iodine.Type: GrantFiled: October 1, 1984Date of Patent: November 5, 1985Assignee: Phillips Petroleum CompanyInventor: Raymond L. Cobb