Attachment To Side-chain, E.g., Telomerization, Etc. Patents (Class 585/452)
  • Patent number: 5227561
    Abstract: The invention concerns a process for the co-dimerization of a vinyl aromatic monomer (e.g. styrene) with an .alpha.-monoolefin monomer (e.g. ethylene, propylene or 1-butylene), using a catalyst composition comprising palladium, an anion of a strong acid and an aliphatic diphosphine.
    Type: Grant
    Filed: August 12, 1992
    Date of Patent: July 13, 1993
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5227559
    Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by heating an alumina, an alkali metal hydroxide and an alkali metal or an alumina containing at least 1.3% by weight of water and an alkali metal in an inert gas atmosphere at a specific temperature as a catalyst.
    Type: Grant
    Filed: January 7, 1992
    Date of Patent: July 13, 1993
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Masami Fukao, Takuo Hibi, Kazuo Kimura, Masahiro Usui, Gohfu Suzukamo
  • Patent number: 5202515
    Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an alkyl aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by heating and reacting an alumina with at least one carbonate of an alkali metal and at least one material selected from the group consisting of potassium and alkali metal hydrides at a temperature of from 180.degree. to 800.degree. C. in an inert gas atmosphere, as a catalyst.
    Type: Grant
    Filed: May 14, 1991
    Date of Patent: April 13, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Fukao, Takuo Hibi, Kiyoshi Ikimi, Gohfu Suzukamo
  • Patent number: 5198594
    Abstract: An improved process for alkylating an alkylaromatic having at least one benzylic hydrogen atom with an olefinic compound comprising contacting the alkylaromatic under liquid phase conditions with an olefinic compound in the presence of at least one alkali metal activated by sonication.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: March 30, 1993
    Assignee: Amoco Corporation
    Inventors: Lawrence D. Lillwitz, Anne M. Karachewski
  • Patent number: 5198595
    Abstract: Monoalkylated benzene such as ethylbenzene and cumene or monoalkylated substituted benzene are produced by alkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 40:1, preferably 160:1. In a subsequent, optional process, the polyalkylated benzene or polyalkylated substituted benzene produced in the alkylation is transalkylated in the presence of an acidic mordenite zeolite catalyst.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: March 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
  • Patent number: 5196622
    Abstract: A process is provided comprising contacting a hydrocarbyl alkali metal compound with a nitrogen-containing compound in the presence of an aromatic compound and at least one alpha-olefin. Optionally, a catalytic support is present during this contacting. In another embodiment of this invention a process is provided comprising: (a) contacting a hydrocarbyl alkali metal compound with a nitrogen-containing compound in the presence of an aromatic compound; and thereafter (b) recovering an aromatic/alkali metal/nitrogen complex; and thereafter (c) contacting said aromatic/alkali metal/nitrogen complex with an alpha-olefin. Optionally, a catalytic support is present during steps a, b, and c.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: March 23, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Ted M. Pettijohn, Mark E. Lashier
  • Patent number: 5180872
    Abstract: The title compounds can be prepared by reaction of a styrene derivative with ethylene in the presence of a nickel catalyst which carries a phosphorus-oxygen chelate ligand, at a temperature of 20.degree.to 160.degree. C. and an ethylene pressure of 1 to 200 bar. Styrene derivatives extended with ethylene, of the formula ##STR1## in which R.sup.19 denotes hydrogen, C.sub.1 -C.sub.4 -alkyl, vinyl or chlorine and R.sup.38 denotes C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.7 -acyl, flourine, chlorine or bromine andm assumes values of 4-104,with the exception of compounds wherein R.sup.19 denotes hydrogen and R.sup.38 denotes i-butyl or benzoyl, and m assumes the value 4, are new.
    Type: Grant
    Filed: May 23, 1991
    Date of Patent: January 19, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Karl-Heinz A. O. Starzewski
  • Patent number: 5118895
    Abstract: An alkyl-substituted hydrocarbon is prepared effectively under mild conditions by alkylating an alkyl aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by treating a water-containing oxide of an alkaline earth metal with at least one material selected from the group consisting of alkali metals and alkali metal hydrides in an amount of 0.5 to 3.5 equivalents per one mole of water in said oxide in an inert gas atmosphere.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: June 2, 1992
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Takuo Hibi, Masami Fukao, Kiyoshi Ikimi, Gohfu Suzukamo
  • Patent number: 5097061
    Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step A of forming p-isobutylstyrene from p-isobutylethylbenzene and a step B of forming .alpha.-(4-isobutylphenyl)propionaldehyde from p-isobutylstyrene or a step C of forming .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester from p-isobutylstyrene.Furthermore, a method for preparing said p-isobutylethylbenzene is also disclosed which comprises alkylating isobutylbenzene or 4-ethyltoluene with ethylene or propylene.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: March 17, 1992
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yuuichi Tokumoto, Kazumichi Uchida
  • Patent number: 5097088
    Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an alkylaromatic hydrocarbon having at least one hydrogen atom on an alpha-carbon in a side chain with an olefin in the presence of a solid base which is obtainable by treating an alumina with at least one compound of an alkaline earth metal at a temperature of from 200.degree. to 800.degree. C. and then with at least one compound selected from the group consisting of an alkali metal and an alkali metal hydride in an inert gas at a temperature of from 200.degree. to 800.degree. C.
    Type: Grant
    Filed: September 21, 1990
    Date of Patent: March 17, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Fukao, Takuo Hibi, Kiyoshi Ikimi, Gohfu Suzukamo
  • Patent number: 5068476
    Abstract: Liquid olefin oligomers are produced by the oligomerization of C.sub.2 -C.sub.5 alpha olefin alone or with ethylene as a co-monomer. The oligomers having high viscosity index and a structure which is characterized by a regio-irregularity of at least 20 percent, usually from 20 to 40 percent. The olefins are oligomerized with a reduced valence state chromium oxide catalyst on a silica support, usually at a temperature from 90.degree. to 250.degree. C., although lower temperatures can also be used with ethylene as a con-monomer. The liquid oligomerization products can be produced in wide range of viscosities including the direct production of low viscosity lubricants having high viscosity index.
    Type: Grant
    Filed: January 29, 1991
    Date of Patent: November 26, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Margaret M. Wu, Suzzy C. Ho
  • Patent number: 5043507
    Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an alkyl aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by reacting an alumina with an alkali metal carbonate and/or aluminate and an alkali metal amd/or its hydride in an inert gas atmosphere at a temperature of 180.degree. to 800.degree. C. as a catalyst.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: August 27, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Fukao, Takuo Hibi, Kiyoshi Ikimi, Gohfu Suzukamo
  • Patent number: 5034562
    Abstract: An acid-sulfolane catalyzed process of preparing cyclic alkylated compounds such as indanes by reacting a monovinyl aromatic compound with an olefinic compound, such reaction further improved by the addition of a lanthanide oxide, or Group VI A elements and/or oxides or a mixture of such oxides.
    Type: Grant
    Filed: June 8, 1990
    Date of Patent: July 23, 1991
    Assignee: Phillips Petroleum Company
    Inventor: Raymond L. Cobb
  • Patent number: 5030784
    Abstract: The instant invention relates to a process for converting methyl- and/or ethyl-substituted benzene or naphthalene and butadiene to 4-aryl-1-butene or 4-aryl-1-pentene and propylene by:a) reacting a methyl- and/or ethyl-substituted benzene or naphthalene and 1,3-butadiene in the presence of an alkali metal catalyst,b) reacting the butenylated reaction product of step a) with ethylene in the presence of of a disproportionation catalyst, andc) separating from the reaction product of step b) product 4-aryl-1-butene or 4-aryl-1-pentene and propylene.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: July 9, 1991
    Assignee: Shell Oil Company
    Inventor: Lynn H. Slaugh
  • Patent number: 5008480
    Abstract: The instant invention relates to a process for converting toluene and butadiene to styrene and 1-pentene by:(a) reacting touene and 1,3-butadiene in the presence of an alkali metal catalyst,(b) contacting the butenylated reaction product of step (a) with a double bond isomerization catalyst at a temperature sufficient to cause double isomerization,(c) reacting the isomerized product of step (b) with ethylene in the presence of a disproportionation catalyst, and(d) separating from the reaction product of step (c) product styrene and 1-pentene.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: April 16, 1991
    Assignee: Shell Oil Company
    Inventor: Lynn H. Slaugh
  • Patent number: 5004841
    Abstract: Aromatic compounds, such as benzene or biphenyl, are alkylated with an alkylating agent having from one to eight carbons atoms, such as propylene, in the presence of an acidic mordenite zeolite catalyst under conditions sufficient to produce a mixture of substituted aromatic compounds enriched in the linear alkylated isomers, such as p-diisopropylbenzene or p,p'-di(isopropyl)biphenyl, respectively. The novel acidic mordenite catalyst is characterized by its silica/alumina molar ratio, its porosity, and a Symmetry Index. The p,p'-disubstituted isomers of aromatic compounds are useful as monomers in the preparation of thermotropic, liquid crystal polymers.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: April 2, 1991
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Joseph J. Maj, Stephen C. Rocke
  • Patent number: 4990717
    Abstract: A method for the production of a monoalkenylated benzene is disclosed. In this method an alkylbenzene is reacted with a C.sub.4 to C.sub.5 conjugated diene in a fixed catalyst bed containing a supported alkali metal catalyst. A monoalkenylated reaction product is produced and is separated from the reactants.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: February 5, 1991
    Assignee: Amoco Corporation
    Inventor: David L. Sikkenga
  • Patent number: 4990709
    Abstract: A process is disclosed for the oligomerization of C.sub.2 -C.sub.5 alpha olefin mixtures or C.sub.3 -C.sub.5 alpha-olefins alone to produce novel lubricant range products having high viscosity index and regio-regularity not greater than 40%. Lower hydrocarbon fractions useful as gasoline and distillate fuels are also produced. The process comprises contacting said mixtures or C.sub.3 -C.sub.5 alpha-olefins with a reduced valence state chromium oxide catalyst on a silica support in an oligomerization zone under oligomerization conditions comprising a temperature from 90.degree. C. to 250.degree. C. The process can be carried out in dilute form using an inert solvent such as octane. The lubricant products can be produced in wide range of viscosities including the direct production of low viscosity lubricants having high viscosity index.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: February 5, 1991
    Assignee: Mobil Oil Corporation
    Inventor: Margaret M. Wu
  • Patent number: 4982035
    Abstract: An alkene selected from ethene, propene, and mixtures thereof is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of a supported potassium or potassium alloy as a catalyst and cesium oxide as a co-catalyst. In a preferred embodiment of the invention, the active hydrogen-containing aromatic hydrocarbon is an alkylbenzene, such as toluene.
    Type: Grant
    Filed: June 27, 1989
    Date of Patent: January 1, 1991
    Assignee: Ethyl Corporation
    Inventor: R. Scott Smith
  • Patent number: 4982034
    Abstract: A process to purify t-butylstyrene from product containing substantial amounts of t-butylethylbenzene and small amounts of alkenyl-substituted styrene impurities by a combination of vacuum fractionation and vacuum evaporation in the presence a polymerization inhibitor, and treatment with a carbonaceous adsorbent. Such a product to be purified can be prepared by catalytically, oxidatively dehydrogenating over an alkaline pyrophosphate in the vapor phase t-butylethylbenzene containing about 95 wt. % or more of the p-isomer which can be made by alkylating ethylbenzene with isobutylene in a controlled manner in the presence of cooled concentrated sulfuric acid.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: January 1, 1991
    Assignee: Amoco Corporation
    Inventors: Eric J. Moore, Marc L. Kullberg, Lori B. Lane
  • Patent number: 4977124
    Abstract: A catalyst composition having enhanced effectiveness in coupling an alkene with an aromatic hydrocarbon having an active hydrogen on a saturated .alpha.-carbon is obtained by dispersing an alkali metal onto a supported oxide of sodium, potassium, rubidium, cesium, barium, strontium, calcium, or magnesium in the absence of a diluent.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: December 11, 1990
    Assignee: Ethyl Corporation
    Inventor: R. Scott Smith
  • Patent number: 4967029
    Abstract: Alpha-olefins such as 1-decene are copolymerized with vinylaromatic monomers, especially styrene or the alkylstyrenes, to produce liquid lubricant oligomers having a broad range of viscosities, high viscosity index(VI), improved thermal stability and additive solubility characteristics. The lubricant oligomers are random copolymers containing recurring units of 1-alkene and vinyl aromatic monomer in mole ratios between 2:1 and 500:1, but preferably between 5:1 and 100:1 and more preferably from about 10:1 to 50:1. The recurring 1-alkene units of the copolymer have a branch ratio of less than 0.19, indicative of a poly 1-alkene segment of the copolymer chain or backbone that is essentially linear. The copolymerization catalyst is a reduced Group VIB metal catalyst on porous support, preferably reduced chromium oxide on a silica support.
    Type: Grant
    Filed: September 7, 1989
    Date of Patent: October 30, 1990
    Assignee: Mobil Oil Corporation
    Inventor: Margaret M. Wu
  • Patent number: 4962254
    Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an alkyl aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by heating an alumina, an alkali metal hydroxide and an alkali metal hydride or an alumina containing at least 1.3% by weight of water and an alkali metal hydride in an inert gas atmosphere at a temperature of 200.degree. to 800.degree. C. as a catalyst.
    Type: Grant
    Filed: August 9, 1989
    Date of Patent: October 9, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Fukao, Takuo Hibi, Kiyoshi Ikimi, Gohfu Suzukamo
  • Patent number: 4952546
    Abstract: The object of the invention is a catalyst system for selective alkylation of toluene with propylene. The catalyst system contains metallic sodium on a K.sub.2 CO.sub.3 carrier and transition metal oxide, which advantageously is CeO.sub.2, Dy.sub.2 O.sub.3 or Fe.sub.2 O.sub.3, as promoter. The invention also concerns a procedure for selective alkylation of toluene with propylene in the presence of a catalyst system.
    Type: Grant
    Filed: August 11, 1988
    Date of Patent: August 28, 1990
    Assignee: Neste Oy
    Inventors: Pekka Knuuttila, Erkki Halme, Leila Lahtinen, Salme Koskimies
  • Patent number: 4950831
    Abstract: An alkene is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of an unsupported alkali metal as a catalyst under high shear agitation conditions. In preferred embodiments of the invention, the alkene is an alkene of 2-20 carbons, such as ethene or propene; the active hydrogen-containing aromatic hydrocarbon is an alkyl-benzene, such as toluene; the alkali metal is potassium or a potassium alloy; and the high shear agitation conditions are attained by operating a turbine-type impeller at a tip speed of at least about 5 m/sec.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: August 21, 1990
    Assignee: Ethyl Corporation
    Inventors: James S. Staton, Ronald A. Turnblad, Jr., Robert B. Agee
  • Patent number: 4929783
    Abstract: An alkene selected from ethene, propene, and mixtures thereof is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of a supported potassium or potassium alloy as a catalyst and an alkaline earth metal oxide as a co-catalyst. In a preferred embodiment of the invention, the active hydrogen-containing aromatic hydrocarbon is an alkylbenzene, such as toluene.
    Type: Grant
    Filed: June 27, 1989
    Date of Patent: May 29, 1990
    Assignee: Ethyl Corporation
    Inventor: R. Scott Smith
  • Patent number: 4922054
    Abstract: An alkene selected from ethene, propene, and mixtures thereof is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of a supported potassium or potassium alloy as a catalyst and sodium oxide, potassium oxide, rubidium oxide, or a mixture of any two or all three thereof as a co-catalyst. In preferred embodiments of the invention, the active hydrogen-containing aromatic hydrocarbon is an alkylbenzene, such as toluene; and the co-catalyst is sodium oxide.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: May 1, 1990
    Assignee: Ethyl Corporation
    Inventor: R. Scott Smith
  • Patent number: 4914251
    Abstract: The present invention concerns a catalyst for alkylation of alkyl aromatics with olefins, i.e. alkylating toluene, a procedure for the production of the catalyst, and a procedure for carrying out the alkylating of the toluene. The catalyst system contains sodium oxide (Na.sub.2 O) on a potassium carbonate (K.sub.2 CO.sub.3) carrier, preferably at about 10 to 70%.
    Type: Grant
    Filed: February 10, 1989
    Date of Patent: April 3, 1990
    Assignee: Neste OY
    Inventors: Pekka Knuuttila, Aila Ali-Hokka
  • Patent number: 4914250
    Abstract: An alkene selected from ethene, propene, and mixtures thereof is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of a supported potassium or potassium alloy as a catalyst and sodium hydroxide, potassium hydroxide, or a mixture thereof as a co-catalyst. In preferred embodiments of the invention, the active hydrogen-containing aromatic hydrocarbon is an alkylbenzene, such as toluene; and the co-catalyst is a hydroxide or hydroxide mixture formed in situ by adding water to the potassium or potassium alloy.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: April 3, 1990
    Assignee: Ethyl Corporation
    Inventor: R. Scott Smith
  • Patent number: 4891448
    Abstract: Polycyclic aromatic compounds, such as biphenyl, are alkylated with an alkylating agent, such as propylene, in the presence of an acidic mordenite zeolite catalyst under conditions sufficient to produce a mixture of substituted polycyclic aromatic compounds enriched in the para alkylated isomers, such as p,p'-di(isopropyl)biphenyl. The novel acidic mordenite catalyst is characterized by its silica/alumina molar ratio, its porosity, and a Symmetry Index. The p,p'-disubstituted isomers of polycyclic aromatic compounds are useful as monomers in the preparation of thermotropic, liquid crystal polymers.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: January 2, 1990
    Assignee: The Dow Chemical Company
    Inventors: Juan Garces, Joseph J. Maj, G. John Lee, Stephen C. Rocke
  • Patent number: 4877916
    Abstract: 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: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877910
    Abstract: 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: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877915
    Abstract: 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: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877912
    Abstract: 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: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877911
    Abstract: 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: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877914
    Abstract: 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: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 4877913
    Abstract: 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: Grant
    Filed: January 27, 1989
    Date of Patent: October 31, 1989
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • 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: 4620056
    Abstract: A method for producing an aromatic hydrocarbon easily and safely without the use of carrier-supported catalyst and is characterized in that an unsaturated compound having a double bond or bonds that are conjugated with the benzene ring is allowed to coexist in the process to alkylate a substituted aromatic hydrocarbon with olefins in the presence of 5 mM or more of metallic sodium and potassium compound to provide 3 mM or more of potassium ions relative to 1 mole of the substituted aromatic hydrocarbon, said substituted aromatic hydrocarbon having at least one alkyl group or alkylene group which has at least one hydrogen atom in the .alpha.-position relative to the aromatic ring of said substituted aromatic hydrocarbon.
    Type: Grant
    Filed: August 28, 1985
    Date of Patent: October 28, 1986
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Hideki Nomura, Kazumichi Uchida, Hitoshi Mitsuyuki
  • Patent number: 4547477
    Abstract: The viscosity of hydrocarbon solutions of dialkylmagnesium compounds are reduced by using a reducing agent comprising a defined benzene derivative, a substance produced by reacting such a benzene derivative with magnesium or a dialkylmagnesium compound or a mixture of one of the foregoing with an organoaluminum viscosity reducing agent.
    Type: Grant
    Filed: March 21, 1984
    Date of Patent: October 15, 1985
    Assignee: Texas Alkyls, Inc.
    Inventors: Dennis B. Malpass, Dale W. Webb
  • Patent number: 4517075
    Abstract: A process is provided for conducting organic compound conversion over a catalyst comprising a high silica crystalline zeolite which has been treated by contact with aluminum chloride vapor.
    Type: Grant
    Filed: December 28, 1983
    Date of Patent: May 14, 1985
    Assignee: Mobil Oil Corporation
    Inventors: Ralph M. Dessau, George T. Kerr
  • Patent number: 4515682
    Abstract: A process is provided for conducting organic compound conversion over a catalyst composition comprising a specially treated crystalline zeolite having a high initial silica-to-alumina mole ratio, said zeolite having been synthesized from a reaction mixture comprising a diamine as a cation source. The treatment of the zeolite material comprises the sequential steps of reacting the zeolite with a dilute hydrogen fluoride solution, contacting the hydrogen fluoride solution reacted material with aluminum chloride vapor, and then treating the aluminum chloride contacted material to convert it to hydrogen form.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: May 7, 1985
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Joseph N. Miale
  • Patent number: 4205189
    Abstract: Benzene or alkylbenzene (e.g., toluene) is alkylated with propylene to produce diisopropylbenzenes or isopropylalkylbenzenes, which in turn are selectively cracked to remove the 1,4-isomer. The resultant product, containing a high level of the 1,3-isomer, is then oxidized to 1,3-dihydroxybenzene or 3-alkylphenol (e.g. 3-methylphenol) in significant yield.
    Type: Grant
    Filed: December 14, 1978
    Date of Patent: May 27, 1980
    Assignee: Mobil Oil Corporation
    Inventors: Lewis B. Young, George T. Burress
  • Patent number: 4179472
    Abstract: A process whereby alkyl substituted aromatics are alkylated with a monoolefin in the presence of an alkali metal catalyst and a promoter composition selected from the group consisting of (1) biphenyl and a conjugated diene, (2) biphenyl, a conjugated diene, and a tertiary amine, and (3) naphthalene and a tertiary amine.
    Type: Grant
    Filed: December 14, 1978
    Date of Patent: December 18, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Raymond L. Cobb
  • Patent number: 4179471
    Abstract: A process whereby alkyl-substituted aromatics are alkylated with a monoolefin in the presence of an alkali metal catalyst and a promoter composition selected from the group consisting of (1) naphthalene, at least one tertiary amine, and at least one tertiary alcohol or alkali metal salt thereof, and (2) naphthalene and at least one tertiary alcohol or alkali metal salt thereof.
    Type: Grant
    Filed: December 14, 1978
    Date of Patent: December 18, 1979
    Assignee: Phillips Petroleum Company
    Inventors: Raymond L. Cobb, Lawrence M. Fodor
  • Patent number: 4179580
    Abstract: A process for increasing the reaction rate of condensation reactions which occur between non-conjugated non-aromatic olefinically unsaturated hydrocarbons and active hydrogen-containing organic compounds in the presence of alkali metal comprising carrying out the reaction in the presence of titanium metal.
    Type: Grant
    Filed: May 11, 1978
    Date of Patent: December 18, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Raymond L. Cobb