Using Halogen-containing Catalyst Patents (Class 585/462)
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Patent number: 5220087Abstract: A fluorinated cation exchange resin catalyst is prepared by contacting a polymer containing pendant acid groups, particularly the radical --SO.sub.3 X with elemental fluorine in the presence of a water-free halogenated hydrocarbon liquid and thereafter converting the resulting pendant --SO.sub.3 X radical to a free acid.Type: GrantFiled: December 13, 1991Date of Patent: June 15, 1993Assignee: Allied-Signal Inc.Inventors: Morris B. Berenbaum, Thomas P. J. Izod, Donald R. Taylor, John D. Hewes
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Patent number: 5202514Abstract: Benzyltoluene/dibenzyltoluene oligomers essentially devoid of contaminating amounts of chlorine values, well adapted as dielectric liquids, are prepared by (a) condensing benzyl chloride with toluene or with lower benzyltoluene oligomers in the presence of a catalytically effective amount of ferric chloride, and then (b) directly dechlorinating the crude product of condensation, e.g., by contacting same with sodium methylate.Type: GrantFiled: December 28, 1990Date of Patent: April 13, 1993Assignee: AtochemInventors: Raymond Commandeur, Daniel Missos
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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: 5181992Abstract: Mixtures of isomers, e.g., mixtures of phenethyl bromide and 1-phenyl-1-bromoethane, are separated by (a) selectively condensing one such isomer with an aromatic compound bearing at least one aryl (nuclear) hydrogen atom, e.g., xylene, in the presence of a catalytically effective amount of a Friedel-Crafts catalyst, e.g., ferric chloride, and then (b) separating the product of condensation, e.g., phenylxylylethane, from the unreacted isomer.Type: GrantFiled: June 13, 1990Date of Patent: January 26, 1993Assignee: AtochemInventors: Raymond Commandeur, Gilles Drivon, Elie Ghenassia
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Patent number: 5171915Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support.Type: GrantFiled: February 21, 1989Date of Patent: December 15, 1992Assignee: Mobil Oil CorporationInventors: Thomas R. Forbus, Bruce P. Pelrine
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Patent number: 5135642Abstract: This invention relates to novel silicon enhanced aluminas (SEAL), processes to prepare them, and hydrocarbon conversion processes using the SEALs. The SEAL compositions have a bulk empirical formula of Al.sub.2-x Si.sub.x O.sub.3 F.sub.x where x varies from about 0.01 to about 0.5. This SEAL material has a three-dimensional pore structure with the pores having diameters in the range of about 20 to about 300.ANG., a crystal structure characteristic of alumina, and where the surface of the SEAL has a higher silicon concentration than the interior of the SEAL. The SEAL is prepared by contacting an alumina with a fluorosilicate salt. This SEAL can be calcined to give a calcined seal with a formula Al.sub.2-x Si.sub.x O.sub.3 F.sub.y where x is as defined above and y varies from 0.01 to x. The calcined SEAL contains both strong and weak acid sites. These SEAL compositions are particularly useful in hydrocracking, cracking and alkylation processes.Type: GrantFiled: February 19, 1991Date of Patent: August 4, 1992Assignee: UOPInventor: Susan L. Lambert
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Patent number: 5105047Abstract: Improved processes for acid-catalyzed oligomerization of olefins and alkylation of toluene are disclosed using a catalyst blend of at least one perfluorinated ion-exchange polymer containing sulfonic acid groups and at least one polymer diluent in a nonpolar reaction mixture.Type: GrantFiled: August 2, 1989Date of Patent: April 14, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Francis J. Waller
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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: 5003120Abstract: A process for the selective manufacture of 2,6-diisopropylnaphthalene from naphthalene advantageously combines an equilibration reactor to enhance the amount of monoisopropylnaphthalene fed to the alkylation reactor, and the use of a shape selective catalyst in the alkylation reactor, to obtain an alkylation reaction product in which the 2,6-diisopropylnaphthalene isomer comprises greater than 39 mole percent of the total diisopropylnaphthalene obtained. Further, this combination of reaction steps and conditions produces a reaction product in which the ratio of 2,6-diisopropylnaphthalene to 2,7-diisopropylnaphthalene is greater than 1.0, preferably greater than 1.2. Recycled process components are fed to the equilibration reactor where they are combined with fresh naphthalene feed to provide a monoisopropylnaphthalene enriched feed to the alkylation reactor.Type: GrantFiled: January 27, 1989Date of Patent: March 26, 1991Assignee: Catalytica, Inc.Inventors: Stanley F. Newman, Jere D. Fellmann, Peter H. Kilner
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Patent number: 4950832Abstract: Dialkylnaphthalenes, especially 2,6-dialkylnaphthalene can be prepared with good yield for a long time by reacting naphthalene and/or monoalkylnaphthalenes with C.sub.2 -C.sub.4 olefin in the presence of silica-alumina catalyst containing 0.1-15 weight percent of fluorine under suitable conditions.Type: GrantFiled: July 19, 1988Date of Patent: August 21, 1990Assignee: Nikki Chemical Co., Ltd.Inventor: Mitsuo Kojima
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Patent number: 4891465Abstract: In a process for producing an alkyl group-substituted aromatic hydrocarbon according to the present invention, (i) an aromatic hydrocarbon is reacted with (ii) an alkylating agent selected from the group consisting of olefins, lower aliphatic alcohols and alkyl halides in the presence of a mordenite-type zeolite catalyst treated with a fluorine-containing compound, and therefore the conversion of the aromatic compound can be increased and further it is possible to introduce the specific number of alkyl groups into the specific position of the aromatic compound.In particular, when biphenyl is used as the aromatic hydrocarbon and propylene is used as the alkylating agent, p,p'-diisopropylbiphenyl can be obtained in a high yield and high selectivity.Type: GrantFiled: July 6, 1988Date of Patent: January 2, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Katsuo Taniguchi, Michio Tanaka, Kazunori Takahata, Naoya Sakamoto, Toshihiro Takai, Yoshito Kurano, Masayasu Ishibashi
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Patent number: 4814483Abstract: Optionally substituted 2-benzyl-toluenes can be prepared by reaction of optionally substituted 2-benzyl-tert.-alkyl-toluenes with an optionally substituted aromatic hydrocarbon in the presence of anhydrous iron-(III) halide. The reaction is carried out at ambient to elevated temperature. The optionally substituted aromatic hydrocarbon is employed in molar excess, relative to the 2-benzly-tert.-alkyl-toluenes.Type: GrantFiled: December 12, 1986Date of Patent: March 21, 1989Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Gunter Silber
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Patent number: 4721825Abstract: A process for producing xylene from toluene or benzene by the use as a catalyst of a fluorine-containing crystalline aluminosilicate or a fluorine-containing crystalline borosilicate. The specified crystalline silicate catalyst increases the conversion of toluene or benzen and the selectivity of xylene. This catalyst can keep its high catalytic activity for long periods of time during the reaction.Type: GrantFiled: June 8, 1984Date of Patent: January 26, 1988Assignee: Idemitsu Kosan Company LimitedInventors: Sumihiro Oda, Haruhito Sato
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Patent number: 4673769Abstract: This invention provides a catalyst product for hydrocarbon conversion reactions and a method for reacting hydrocarbons employing such catalyst product. The catalyst product is a composite of a perfluorinated polymersulfonic acid and an ion-stabilizing agent such as hexafluoroisopropanol or trifluoroacetic acid. The composite catalyst has a significantly higher Bronsted acidity than the perfluorinated polymersulfonic acid. When the catalyst composite is used to catalyze the alkylation of toluene with 1-hexene, for example, the rate of alkylation is from about 20 to 30 times greater than using the perfluorinated polymersulfonic acid alone.Type: GrantFiled: December 13, 1985Date of Patent: June 16, 1987Assignee: Exxon Research and Engineering CompanyInventor: Dan Farcasiu
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Patent number: 4658072Abstract: A lubricant composition having an improved viscosity index and flash point is prepared by reacting diisopropylbenzenes and hexylbenzenes with alpha olefins using a tantalum (V) halide/oxide-gel oxide catalyst.Type: GrantFiled: August 22, 1984Date of Patent: April 14, 1987Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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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: 4562280Abstract: The invention is a process for the chloromethylation of an aromatic compound, substituted with an alkyl group and a deactivating moiety, which comprises contacting an aromatic compound, substituted with an alkyl group and a deactivating group, with a chloromethyl alkyl ether in the presence of a catalytic amount of ferric chloride or stannic chloride, under conditions such that an aromatic compound, substituted with an alkyl group, a chloromethyl group, and a deactivating group, wherein the alkyl and chloromethyl groups are on adjacent carbon atoms, is prepared.Type: GrantFiled: October 18, 1984Date of Patent: December 31, 1985Assignee: The Dow Chemical CompanyInventors: Jo Ann Gilpin, Lowell B. Lindy
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Patent number: 4547604Abstract: Resorcinol is prepared in high yield and purity by an improved process through superacid (such as perfluorinated alkanesulfonic acids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as acidified Nafion-H, catalyzed cleavage rearrangement reaction of meta-bis(2-hydroperoxy-2-propyl)benzene (meta-diisopropylbenzene dihydroperoxide). Part of the process is the preparation of needed meta-diisopropylbenzene in high purity (98-100%) substantially free of other isomers by treating any mixture of diisopropylbenzenes with an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic acid of one to eighteen carbon atoms and a Lewis acid fluoride, or by alkylating (transalkylating) cumene with a propyl alkylating agent in the aforementioned superacid systems.Type: GrantFiled: February 6, 1984Date of Patent: October 15, 1985Assignee: PCUK Produits Chimiques Ugine KuhlmannInventor: George A. Olah
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Patent number: 4524229Abstract: Benzene and substituted benzene compounds are alkylated with olefins by contact with a catalyst which comprises a metal oxide substrate having niobium (V) halide/oxide bound to the surface of the substrate.Type: GrantFiled: January 16, 1985Date of Patent: June 18, 1985Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 4520219Abstract: A process for producing pseudocueme or durene is described, comprising methylating xylene by the use as a catalyst of at least one crystalline silicate selected from the group consisting of crystalline borosilicate, fluorine-containing crystalline borosilicate, fluorine-containing crystalline aluminosilicate, and fluorine-containing crystalline boroaluminosilicate. The specific crystalline silicate catalyst increases the conversion of xylene and the selectivity of pseudocumene or durene. The process of the invention can be performed either in one step or in two steps. The two-step reaction provides various industrial advantages, such as a high degree of utilization of the methylating agent and a great increase in the selectivity of the product.Type: GrantFiled: September 14, 1983Date of Patent: May 28, 1985Assignee: Idemitsu Kosan Company LimitedInventor: Haruhito Sato
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Patent number: 4476340Abstract: Benzene and substituted benzene compounds are alkylated with alkyl halides by contact with a catalyst which comprises a metal oxide substrate having tantalum (V) halide/oxide bound to the surface of the substrate.Type: GrantFiled: September 23, 1983Date of Patent: October 9, 1984Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 4469804Abstract: Catalysts containing niobium or tantalum halides which have been deactivated by contact with oxygen are regenerated by being contacted with a halogenated hydrocarbon.Type: GrantFiled: September 23, 1983Date of Patent: September 4, 1984Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 4463207Abstract: Benzene and substituted benzene compounds are alkylated with olefins by contact with a catalyst which comprises a metal oxide substrate having tantalum (V) halide/oxide bound to the surface of the substrate.Type: GrantFiled: September 23, 1983Date of Patent: July 31, 1984Assignee: Shell Oil CompanyInventor: Thomas H. Johnson