Using Halogen-containing Catalyst Patents (Class 585/462)
  • Patent number: 5220087
    Abstract: 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: Grant
    Filed: December 13, 1991
    Date of Patent: June 15, 1993
    Assignee: Allied-Signal Inc.
    Inventors: Morris B. Berenbaum, Thomas P. J. Izod, Donald R. Taylor, John D. Hewes
  • Patent number: 5202514
    Abstract: 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: Grant
    Filed: December 28, 1990
    Date of Patent: April 13, 1993
    Assignee: Atochem
    Inventors: Raymond Commandeur, Daniel Missos
  • Patent number: 5191136
    Abstract: 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: Grant
    Filed: September 9, 1991
    Date of Patent: March 2, 1993
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Kazuteru Takahashi, Yasuhiko Higashio
  • Patent number: 5181992
    Abstract: 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: Grant
    Filed: June 13, 1990
    Date of Patent: January 26, 1993
    Assignee: Atochem
    Inventors: Raymond Commandeur, Gilles Drivon, Elie Ghenassia
  • Patent number: 5171915
    Abstract: 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: Grant
    Filed: February 21, 1989
    Date of Patent: December 15, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas R. Forbus, Bruce P. Pelrine
  • Patent number: 5135642
    Abstract: 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: Grant
    Filed: February 19, 1991
    Date of Patent: August 4, 1992
    Assignee: UOP
    Inventor: Susan L. Lambert
  • Patent number: 5105047
    Abstract: 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: Grant
    Filed: August 2, 1989
    Date of Patent: April 14, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Francis J. Waller
  • Patent number: 5087785
    Abstract: 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: Grant
    Filed: December 3, 1990
    Date of Patent: February 11, 1992
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 5003120
    Abstract: 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: Grant
    Filed: January 27, 1989
    Date of Patent: March 26, 1991
    Assignee: Catalytica, Inc.
    Inventors: Stanley F. Newman, Jere D. Fellmann, Peter H. Kilner
  • Patent number: 4950832
    Abstract: 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: Grant
    Filed: July 19, 1988
    Date of Patent: August 21, 1990
    Assignee: Nikki Chemical Co., Ltd.
    Inventor: Mitsuo Kojima
  • Patent number: 4891465
    Abstract: 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: Grant
    Filed: July 6, 1988
    Date of Patent: January 2, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Katsuo Taniguchi, Michio Tanaka, Kazunori Takahata, Naoya Sakamoto, Toshihiro Takai, Yoshito Kurano, Masayasu Ishibashi
  • Patent number: 4814483
    Abstract: 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: Grant
    Filed: December 12, 1986
    Date of Patent: March 21, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Gunter Silber
  • Patent number: 4721825
    Abstract: 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: Grant
    Filed: June 8, 1984
    Date of Patent: January 26, 1988
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Sumihiro Oda, Haruhito Sato
  • Patent number: 4673769
    Abstract: 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: Grant
    Filed: December 13, 1985
    Date of Patent: June 16, 1987
    Assignee: Exxon Research and Engineering Company
    Inventor: Dan Farcasiu
  • Patent number: 4658072
    Abstract: 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: Grant
    Filed: August 22, 1984
    Date of Patent: April 14, 1987
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4599472
    Abstract: 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: Grant
    Filed: June 27, 1985
    Date of Patent: July 8, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Raymond L. Cobb
  • Patent number: 4562280
    Abstract: 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: Grant
    Filed: October 18, 1984
    Date of Patent: December 31, 1985
    Assignee: The Dow Chemical Company
    Inventors: Jo Ann Gilpin, Lowell B. Lindy
  • Patent number: 4547604
    Abstract: 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: Grant
    Filed: February 6, 1984
    Date of Patent: October 15, 1985
    Assignee: PCUK Produits Chimiques Ugine Kuhlmann
    Inventor: George A. Olah
  • Patent number: 4524229
    Abstract: 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: Grant
    Filed: January 16, 1985
    Date of Patent: June 18, 1985
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4520219
    Abstract: 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: Grant
    Filed: September 14, 1983
    Date of Patent: May 28, 1985
    Assignee: Idemitsu Kosan Company Limited
    Inventor: Haruhito Sato
  • Patent number: 4476340
    Abstract: 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: Grant
    Filed: September 23, 1983
    Date of Patent: October 9, 1984
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4469804
    Abstract: Catalysts containing niobium or tantalum halides which have been deactivated by contact with oxygen are regenerated by being contacted with a halogenated hydrocarbon.
    Type: Grant
    Filed: September 23, 1983
    Date of Patent: September 4, 1984
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4463207
    Abstract: 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: Grant
    Filed: September 23, 1983
    Date of Patent: July 31, 1984
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson