Hydroxy Bonded Directly To The Ring (e.g., Terpin Hydrate, Etc.) (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/832)
  • Patent number: 4617145
    Abstract: Described are the 1-methyl-2(2-methylbutyl) cyclohexanol derivatives defined according to the generic structure: ##STR1## wherein R represents hydrogen, MgCl, MgBr, lithium or acetyl; and uses of such 1-methyl-2(2-methylbutyl) cyclohexanol derivatives where R is hydrogen or acetyl for their organoleptic properties in augmenting or enhancing the aroma of perfume compositions, colognes or perfumed articles. Also described is the process for preparing such 1-methyl-2(2-methylbutyl) cyclohexanol derivatives including the reactions: ##STR2## wherein the latter reaction takes place using a methane sulfonic acid catalyst.
    Type: Grant
    Filed: November 21, 1985
    Date of Patent: October 14, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, Anubhav P. S. Narula, Marie R. Hanna
  • Patent number: 4600800
    Abstract: An epoxide is isomerized in the liquid phase in the presence of a solid alumina catalyst and preferably an inert gaseous diluent, the isomerization conducted in the downflow mode.
    Type: Grant
    Filed: December 3, 1985
    Date of Patent: July 15, 1986
    Assignee: Shell Oil Company
    Inventors: Robert H. Ellison, Peter S. Friend
  • Patent number: 4588846
    Abstract: A process is provided for producing a cyclic alcohol by catalytic hydration of a cyclic olefin in a liquid phase, which comprises using as a catalyst a zeolite having a population ratio of acid sites on the external surface to total acid sites of 0.07/1 or more, conducting the hydration reaction in a reaction zone in the copresence of an oil phase mainly containing cyclic olefin and an aqueous phase mainly containing water and the catalyst while controlling the cyclic alcohol produced so that the concentration thereof in the oil phase is more than that in the aqueous phase, and separating and recovering the cyclic alcohol produced from the oil phase.
    Type: Grant
    Filed: November 9, 1984
    Date of Patent: May 13, 1986
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Osamu Mitsui, Yohei Fukuoka
  • Patent number: 4551564
    Abstract: 2- and 4-tert-butylcyclohexanols are produced having high proportions of cis-isomers, by hydrogenating the corresponding tert-butylphenols in the presence of Pd and Ru catalysts in two stages under hydrogen pressures of above 200 bar and at temperatures of 70.degree.-280.degree. C. In the first stage, a Pd catalyst is employed, and a Ru catalyst is used in the second stage.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: November 5, 1985
    Assignee: Chemische Werke Huels, AG
    Inventors: Werner Otte, Rudolf Nehring, Manfred zur Hausen
  • Patent number: 4528409
    Abstract: The catalytic hydration of a cycle olefin in the co-presence of an aromatic sulfonic acid and a heteropoly acid has been found to be extremely effective for preparing a cyclic alcohol efficiently and in high yield.
    Type: Grant
    Filed: July 12, 1983
    Date of Patent: July 9, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Osamu Mitsui, Yohei Fukuoka
  • Patent number: 4508918
    Abstract: Cyclohexane derivatives such as cyclohexanol and cyclohexyl carboxylates are produced directly from aromatic hydrocarbons. The reaction may be carried out, under hydrogenation conditions, by reacting an aromatic hydrocarbon with hydrogen and a reagent selected from the group consisting of water, and carboxylic acids in the presence of a strong acid and a hydrogenation catalyst.
    Type: Grant
    Filed: November 20, 1979
    Date of Patent: April 2, 1985
    Assignee: Toray Industries, Inc.
    Inventors: Yutaka Yasuhara, Masaki Nishino, Seikichi Matsuhisa
  • Patent number: 4459419
    Abstract: Zeolite-ruthenium catalysts in which the ruthenium is in the form of a cation are very effective in catalyzing the hydrogenation of a broad range of organic compounds.
    Type: Grant
    Filed: September 2, 1982
    Date of Patent: July 10, 1984
    Assignee: Ethyl Corporation
    Inventor: Paul D. Seemuth
  • Patent number: 4393253
    Abstract: A method for preparing polyols such as diols by catalytic hydroxylation of an olefinic compound by reacting the olefinic compound with an organic hydroperoxide and water in the presence of a catalyst comprising osmium compound and a specific halide co-catalyst is disclosed.
    Type: Grant
    Filed: October 9, 1981
    Date of Patent: July 12, 1983
    Assignee: Exxon Research & Engineering Co.
    Inventors: Robert C. Michaelson, Richard G. Austin
  • Patent number: 4371722
    Abstract: Disclosed are novel cyclic terpenoid amines which can be prepared by cyclizing the corresponding acyclic terpenoid amine.
    Type: Grant
    Filed: June 26, 1981
    Date of Patent: February 1, 1983
    Assignee: SCM Corporation
    Inventors: Bernard J. Kane, Richard A. Von Genk
  • Patent number: 4370257
    Abstract: A process for producing a magnesium containing support for titanium comprising contacting magnesium metal, a halogenated hydrocarbon and a compound represented by the formula X'.sub.m C(OR').sub.4-m wherein X' is a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.10 alkyl, aryl, cycloalkyl or halogenated alkyl, aryl, cycloalkyl group, R' is a C.sub.1 -C.sub.20 alkyl, aryl or cycloalkyl group and m is 0, 1 or 2 to form a magnesium-containing solid represented by the formula R'OMgX and thereafter contacting the magnesium-containing solid with a Lewis base or a compound which can form an ester such as benzoyl chloride and a titanium compound such as titanium tetrachloride. The obtained magnesium supported titanium composition is useful as a catalyst component in combination with a co-catalyst organoaluminum compound for the polymerization of olefins.
    Type: Grant
    Filed: August 11, 1980
    Date of Patent: January 25, 1983
    Assignee: Toa Nenryo Kogyo Kabushiki Kaisha
    Inventors: Masafumi Imai, Hiroshi Ueno, Naomi Inaba, Makoto Yoda, Shozo Wada
  • Patent number: 4346240
    Abstract: A novel class of heterogeneous catalysts, containing Group VIII transition metals in combination with alkali organic compounds is prepared, such as potassium naphthalene on ruthenium on carbon. The catalysts are useful as heterogeneous catalysts in the hydrogenation of carboxylic acid esters. A process for producing the materials is described. The catalysts permit the process of the hydrogenation of carboxylic acid esters to primary alcohols to be conducted with the ester in the liquid phase at a temperature not exceeding about 150.degree. C. with high selectivity. Catalysts of Group VIII transition metals and alkali metal on carbon are also useful in such processes.
    Type: Grant
    Filed: September 29, 1981
    Date of Patent: August 24, 1982
    Assignee: Allied Corporation
    Inventors: Roger A. Grey, Guido P. Pez
  • Patent number: 4326085
    Abstract: The invention relates to a method for removal of alkali metal carboxylates from mixtures which contain a cycloalkanone and a cycloalkanol, in particular cyclohexanone and cyclohexanol, and which have been obtained in oxidation in the liquid phase of the corresponding cycloalkane with gas containing molecular oxygen.According to the invention, alkali metal carboxylates are removed from such mixtures containing a cycloalkanone and a cycloalkanol by washing the mixture with an aqueous acid solution, in particular an aqueous solution of carboxylic acid with 1-6 carbon atoms per molecule.The invention provides a solution to the problem of the so-called alkali entrainment, which leads to loss of cycloalkanone owing to condensation into undesired high-boiling by-products in the following distillation for gaining pure cycloalkone. This substantial loss is prevented by the method according to the invention.
    Type: Grant
    Filed: June 11, 1980
    Date of Patent: April 20, 1982
    Assignee: Stamicarbon B.V.
    Inventor: Mario G. R. T. De Cooker
  • Patent number: 4314088
    Abstract: Method for preparing polyols such as diols and triols by the homogeneous catalytic hydroxylation of an olefinic compound by contacting the olefinic compound with an organic hydroperoxide in an inert polar solvent containing catalytic amounts of an osmium compound and a halide and at least a stoichiometric amount of water based on the amount of said olefinic compound.
    Type: Grant
    Filed: November 24, 1980
    Date of Patent: February 2, 1982
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard G. Austin, Robert C. Michaelson
  • Patent number: 4304943
    Abstract: Alkyl and aryl hydroxy compounds are converted to aldehydes, alcohols, and ketones in the presence of hydrogen using a catalyst comprised of the oxides of manganese, nickel and magnesium.
    Type: Grant
    Filed: August 8, 1979
    Date of Patent: December 8, 1981
    Assignee: Phillips Petroleum Company
    Inventor: Geir Bjornson
  • Patent number: 4212990
    Abstract: Cyclohexane derivatives such as cyclohexanol, and cyclohexyl carboxylates are produced directly from aromatic hydrocarbons. The reaction may be carried out, under hydrogenation conditions, by reacting an aromatic hydrocarbon with hydrogen and a reagent selected from the group consisting of water and carboxylic acids in the presence of a strong acid and a hydrogenation catalyst.
    Type: Grant
    Filed: August 5, 1977
    Date of Patent: July 15, 1980
    Assignee: Toray Industries, Inc.
    Inventors: Yutaka Yasuhara, Masaki Nishino, Seikichi Matsuhira
  • Patent number: 4197414
    Abstract: Olefins are converted to alcohols by a one-step, hydroformylation process comprising contacting an olefin, such as 1-hexene, with a gaseous mixture of carbon monoxide and hydrogen in the presence of a catalyst prepared by loading a bimetallic cluster of the formula: Rh.sub.x Co.sub.y CO.sub.12 wherein both x and y are independently integers 1-3 with the proviso that .SIGMA.(x+y)=4, onto an amine resin, such as Dowex.RTM. MWA-1.
    Type: Grant
    Filed: October 18, 1978
    Date of Patent: April 8, 1980
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Philip E. Garrou