By Condensation Using Metal-containing Catalyst Patents (Class 585/438)
  • Patent number: 5334794
    Abstract: A process for producing a monoalkenyl aromatic hydrocarbon compound which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at an .alpha.-position of the side chain (such as xylene) with a conjugated diene having 4 or 5 carbon atoms (such as butadiene) in the presence of a catalyst comprising a mixture obtained by heat treating metallic sodium together with a mixture of a zirconium oxide and a potassium compound in an inert gas atmosphere. An industrially useful monoalkenyl aromatic hydrocarbon compound is produced in a high yield at a low cost with enhanced safety from a specific aromatic hydrocarbon compound and a specific conjugated diene compound.
    Type: Grant
    Filed: April 15, 1993
    Date of Patent: August 2, 1994
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Norio Fushimi, Ko Kedo, Kenji Inamasa, Makoto Takagawa
  • Patent number: 5329058
    Abstract: In a process for producing an alkenylbenzene by the reaction of an alkylbenzene having 8 or more carbon atoms and a conjugated diolefin, the improvement in which the reaction is performed in the presence of a catalyst obtained by dispersing (a) an alkali metal and (b) potassium carbonate and/or potassium hydroxide in the presence of (c) an aromatic hydrocarbon having at least a substituent with a double bond.
    Type: Grant
    Filed: October 23, 1992
    Date of Patent: July 12, 1994
    Assignee: Teijin Limied
    Inventors: Keizo Shimada, Koji Sumitani, Seiji Itoh, Kazuhiro Sato
  • Patent number: 5136114
    Abstract: The invention relates to a new process for the preparation of geminal diarylalkanes of the formula ##STR1## by Friedel-Crafts alkylation of aromatic compounds with specific aliphatic halogen compounds (addition compounds of CCl.sub.4 , to .alpha.-olefins), to new geminal diarylalkanes and the aralkyl compounds resulting as intermediates.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 4962252
    Abstract: Alkenyl-substituted benzene derivatives are produced by oxidatively coupling at elevated temperature a benzene having at least one activated saturated hydrocarbyl substituent in vapor form with a gaseous paraffinic hydrocarbon in the presence of a gaseous oxidant and as catalyst therefor a binary metallic or multimetallic composition capable of oxidatively coupling methane.
    Type: Grant
    Filed: July 25, 1989
    Date of Patent: October 9, 1990
    Assignee: The British Petroleum Company p.l.c.
    Inventor: Steven R. Wade
  • Patent number: 4962253
    Abstract: A process for the preparation of vinyl aromatic compounds comprises contacting an aromatic compound and an olefin in the presence of a catalytic amount of a cyclopentadienyl, indenyl, or fluorenyl rhodium complex under reaction conditions sufficient to form the corresponding vinyl aromatic compound. Novel alkyl- or trimethylsilyl-substituted indenyl or fluorenyl compounds are among the compounds suitable for use in the process of the invention.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: October 9, 1990
    Assignee: The Dow Chemical Company
    Inventor: Robert A. Dubois
  • Patent number: 4935559
    Abstract: A method of preparing an aryl alkene compound comprising reacting an iodoaromatic compound an alkene and an alkanol in the presence of a palladium catalyst and the absence of a Bronsted base.
    Type: Grant
    Filed: January 30, 1989
    Date of Patent: June 19, 1990
    Assignee: Eastman Kodak Company
    Inventors: Mark Rule, Eric J. Fugate
  • Patent number: 4912274
    Abstract: The invention relates to azaphospholenes of the type ##STR1## wherein R.sub.1 and R.sub.2 may be alkyl, aryl and aralkyl groups, processes for preparing same and the use thereof.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: March 27, 1990
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Gunther Wilke, Jaroslaw Monkiewicz, Herbert Kuhn
  • Patent number: 4709109
    Abstract: Alkenylaromatics I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, R.sup.2 is H or C.sub.1 -C.sub.10 -alkyl and Ar is aryl, are prepared by reacting a vinylaromatic II ##STR2## with an .alpha.-olefin IIIH.sub.2 C.dbd.CHR.sup.2 IIIin the presence of a nickel-containing catalyst system consisting of (a) a nickel(II) salt of a carboxylic acid, of an alcoholate or of a phenolate, (b) a phosphite or phosphine and (c) an organoaluminum compound V ##STR3## where R.sup.6 is C.sub.1 -C.sub.12 -alkyl, X is halogen and n is 1 or 2, or a mixture of compounds V.
    Type: Grant
    Filed: October 10, 1986
    Date of Patent: November 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Karin Sperling, Martin Fischer
  • Patent number: 4620055
    Abstract: The present invention provides a novel process for the preparation of styrene, stilbene, and/or substituted derivatives thereof. The process involves the reaction of an aryl sulfonyl chloride with an olefinic compound in the presence of a catalytic amount of a metal catalyst consisting essentially of palladium.
    Type: Grant
    Filed: October 7, 1985
    Date of Patent: October 28, 1986
    Assignee: Eastman Kodak Company
    Inventors: Carl M. Lentz, James R. Overton, David D. Cornell
  • Patent number: 4499317
    Abstract: A modified zeolite catalyst composition and process for using the catalyst composition to alkylate toluene (or derivative thereof) with methanol to form e.g. styrene and ethylbenzene (or derivatives thereof) is disclosed. The catalyst composition is exemplified by a type X- or Y-zeolite modified with (1) at least one alkali metal selected from Cs, K, and Rb; (2) at least one metal selected from Mn, Fe, Cu, and Zn; and (3) boron and/or phosphorus.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: February 12, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Huei-Cheng Liu, Ralph J. Spohn
  • Patent number: 4499318
    Abstract: A modified zeolite catalyst composition and process for using the catalyst composition to alkylate toluene (or derivative thereof) with methanol to form e.g. styrene and ethylbenzene (or derivatives thereof) is disclosed. The catalyst composition is exemplified by a type X- or Y-zeolite modified with (1) at least one alkali metal selected from Cs, K, and Rb; (2) at least one metal selected from Li, Ce, Cr, and Ag; and (3) boron and/or phosphorus.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: February 12, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventor: Huei-Cheng Liu
  • Patent number: 4489212
    Abstract: Arenes are reacted with allyl chloride to produce allylarenes and 2-chloropropyl- or propenylarenes using a catalyst comprising a metal oxide substrate having tantalum (V) halide/oxide bound to the surface of the substrate.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: December 18, 1984
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4479024
    Abstract: Toluene and formaldehyde produce styrene in a gas phase catalytic process using a basic hydroxide of Group I or II, at formaldehyde to toluene mole ratios of from 0.001 to 0.10.
    Type: Grant
    Filed: June 1, 1983
    Date of Patent: October 23, 1984
    Assignee: Ashland Oil, Inc.
    Inventors: Philippe M. Bruylants, Robert L. Garten
  • Patent number: 4463204
    Abstract: A process for alkylating toluene (or derivative thereof) with methanol to form e.g. styrene and ethylbenzene (or derivatives thereof) using a modified low sodium content zeolite catalyst composition is disclosed. The zeolite catalyst composition is exemplified by a type X- or Y-zeolite modified with potassium and cesium through a sequential exchange.
    Type: Grant
    Filed: April 22, 1983
    Date of Patent: July 31, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventor: Huei-Cheng Liu
  • Patent number: 4446284
    Abstract: There is disclosed a process for producing polymers that contain pendant unsaturation. The present invention provides a versatile method for the preparation of polymers that contain a wide range of unsaturated pendant groups.
    Type: Grant
    Filed: May 28, 1982
    Date of Patent: May 1, 1984
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Dane K. Parker
  • Patent number: 4334081
    Abstract: Substituted olefins are prepared by the reaction of an organic halide with an olefin in the presence of a catalyst derived from zinc, a triarylphosphine and a nickel salt.
    Type: Grant
    Filed: January 23, 1981
    Date of Patent: June 8, 1982
    Assignee: Union Carbide Corporation
    Inventor: Ismael Colon
  • Patent number: 4324939
    Abstract: A process for preparing a reaction product of a conjugated diolefin and an aromatic hydrocarbon comprises contacting these reactants with a catalyst comprising(1) a phosphorous modified cobalt compound comprising a cobalt compound which is soluble in the aromatic hydrocarbon and a phosphorous compound of the formula ##STR1## wherein R.sup.17, R.sup.18 and R.sup.19 each, independently, is C.sub.1-14 -alkyl, C.sub.2-14 -alkenyl or C.sub.6-14 -aryl(2) a halogen-containing organoaluminum compound; and(3) a modifier of the formula ##STR2## wherein X is chlorine, bromine, or iodine, andR.sub.1 through R.sup.
    Type: Grant
    Filed: January 9, 1981
    Date of Patent: April 13, 1982
    Assignee: Chemische Werke Huels, AG
    Inventors: Karl Hahn, Wolfgang Kampf
  • Patent number: 4284836
    Abstract: A process for preparing an alkenyl derivative of an aromatic hydrocarbon by reacting a conjugated diolefin with the aromatic hydrocarbon comprises conducting the reaction in the presence of a catalyst comprising:1. a nickel compound which is soluble in the aromatic hydrocarbon;2. an organo-aluminum halide; and3. a modifying agent wherein the modifying agent (3) is a compound of the formulae ##STR1## wherein X in each case is chlorine, bromine or iodine; andR.sup.1 to R.sup.16 independently are each a straight-chain or branched, saturated or unsaturated aliphatic or cycloaliphatic hydrocarbon radical of 1-20 carbon atoms, optionally substituted by 1-41 halogen atoms, ora hydrocarbon aryl radical of 6-14 carbon atoms, optionally substituted by(a) 1-5 straight-chain or branched, saturated or unsaturated, aliphatic or cycloaliphatic radicals, each of 1-10 carbon atoms optionally substituted by halogen atoms, or(b) 1-9 halogen atoms, and wherein R.sup.4 to R.sup.16 can alternatively be hydrogen, andR.sup.1 and R.
    Type: Grant
    Filed: November 6, 1979
    Date of Patent: August 18, 1981
    Assignee: Chemische Werke Huels, A.G.
    Inventors: Karl Hahn, Uwe Biethan
  • Patent number: 4263212
    Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: April 21, 1981
    Assignee: Rikagaku Kenkyusho
    Inventors: Pangbu Hong, Hiroshi Yamazaki