Polycarbon Alkyl Group Containing Patents (Class 568/834)
  • Patent number: 5057630
    Abstract: This invention relates to a new process for preparing certain optically active purine substituted cyclopentene derivatives including the antiviral agent, carbovir, and novel intermediates used in this process. In particular, this invention concerns a synthesis of (1R-cis)-4-hydroxymethyl-2-cyclopenten-1-ol, an intermediate in this process.
    Type: Grant
    Filed: April 6, 1990
    Date of Patent: October 15, 1991
    Assignee: Glaxo Inc.
    Inventors: John W. Lackey, Robert A. Mook, Jr., John J. Partridge
  • Patent number: 4990692
    Abstract: Cyclohexanol is removed from aqueous solutions containing it and aromatic sulfonic acids by extraction with one or more cyclohexyl ethers liquid under extraction conditions and having the formula ##STR1## where R is alkyl of from 1 to 16 catbon atoms, cycloalkyl of from 5 to 8 carbon atoms, aralkyl of from 7 to 10 carbon atoms or phenyl, which may additionally have substituents which are inert under reaction conditions.
    Type: Grant
    Filed: July 21, 1989
    Date of Patent: February 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Gosch, Rolf Fischer
  • Patent number: 4982017
    Abstract: A composition for use in synthesis reactions comprises a mixture of an organolithium compound and an inert inorganic pulverulent carrier and consists of methyllithium and ethyllithium, one or more of the group consisting of SiO.sub.2, Al.sub.2 O.sub.3, CaO and synthetic anhydrous aluminosilicate, and paraffin. That composition is flowable and non-pyrophoric.
    Type: Grant
    Filed: May 3, 1989
    Date of Patent: January 1, 1991
    Assignee: Metallgesellschaft Aktiengesellschaft
    Inventors: Jurgen Deberitz, Wilfried Weiss
  • Patent number: 4933508
    Abstract: A method for producing a cycloalkanol, which comprises oxidizing a cycloalkane with a molecular oxygen-containing gas in a liquid phase in the presence of a catalyst, wherein an aromatic nitro compound is present in the oxidation reaction system.
    Type: Grant
    Filed: September 23, 1988
    Date of Patent: June 12, 1990
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Haruo Habu, Kouji Watanabe, Takeshi Matsuoka
  • Patent number: 4916252
    Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.
    Type: Grant
    Filed: June 16, 1988
    Date of Patent: April 10, 1990
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 4885409
    Abstract: Process for the hydrogenation of bis-phenols by reacting bis-phenols with hydrogen in the presence of a catalytic system consisting of palladium supported on activated carbon.
    Type: Grant
    Filed: May 4, 1988
    Date of Patent: December 5, 1989
    Assignee: Montedison S.p.A.
    Inventors: Andrea Gardano, Francesco Casagrande, Marco Foa, Guido Petrini, Riccardo Barisone, Lawrence Chapoy
  • Patent number: 4820879
    Abstract: The present invention provides a process for making hydrocarbyloxy magnesium halides by reacting in an inert atmosphere under anhydrous conditions activated magnesium metal with an oxygen containing compound of 1 to 20 carbon atoms and an anhydrous hydrogen halide to produce a hydrocarbyloxy magnesium halide.
    Type: Grant
    Filed: June 5, 1987
    Date of Patent: April 11, 1989
    Assignee: Lithium Corporation of America
    Inventor: Vijay C. Mehta
  • Patent number: 4757051
    Abstract: Novel 2-tert-butyl-4-methylcyclohexanol derivatives of the general formula I ##STR1## where R.sup.1 is alkyl of 1 to 3 carbon atoms or an acyl group ##STR2## where R.sup.2 is alkyl of 1 to 5 carbon atoms, and a process for their preparation, their use as scents, and scent compositions containing compounds of the formula I.Particularly interesting compounds are 2-tert-butyl-4-methylcyclohexyl acetate and propionate.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: July 12, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Gramlich, Werner Hoffman, Ludwig Schuster
  • Patent number: 4751214
    Abstract: 2-tert-butyl-4-methylcyclohexanol is used as a scent and as a component of scent compositions.Scent compositions contain 2-tert-butyl-4-methylcyclohexanol (I), which influences their fragrance. It has a very intense earthy woody vetiver-like fragrance and is stable in neutral, acidic and alkaline solutions.
    Type: Grant
    Filed: August 6, 1987
    Date of Patent: June 14, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Gramlich, Werner Hoffmann, Klaas Jansen, Wolfgang Lengsfeld, Ludwig Schuster
  • Patent number: 4720558
    Abstract: Process for inverting the configuration of secondary alcohols in which the hydroxyl group is attached to an asymmetric carbon atom, in accordance with which the secondary alcohols are esterified, with inversion of their configuration, by conversion into isourea ethers and reaction of these isourea ethers with carboxylic acids, and the esters are then saponified with retention of the configuration of the secondary alcohols.
    Type: Grant
    Filed: March 11, 1986
    Date of Patent: January 19, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventor: Johannes Kaulen
  • Patent number: 4719041
    Abstract: The invention relates to the use as perfumes of 1-alkyl/alkenyl cyclohexan-1-ols corresponding to the general formula ##STR1## in which R is a C.sub.1-4 alkyl or a C.sub.2-4 alkenyl, 0 to 3 of the 10 substituents R' are methyl and the balance of the 10 substituents R' are hydrogen, in compositions containing active chlorine, and perfumed compositions so obtained.
    Type: Grant
    Filed: March 20, 1987
    Date of Patent: January 12, 1988
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Ulf-Armin Schaper, Siegfried Bloesl, Klaus Bruns, Benno Streschnak
  • Patent number: 4711875
    Abstract: Composition consisting of from less than 100% to more than about 80% of trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol and a definite amount, but not more than about 20%, of cis-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol.Process for preparing same from .beta.-cyclocitral via a three-, optionally, four-step pathway.Utilization of the said composition as effective perfume ingredient.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: December 8, 1987
    Assignee: Firmenich SA
    Inventors: Karl-Heinrich Schulte-Elte, Gunther Ohloff, Bernard L. Muller, Wolfgang K. Giersch
  • Patent number: 4631147
    Abstract: Novel cycloalkan-1-ol derivatives having a formula (I): ##STR1## wherein R represents a hydrogen atom, lower alkyl group or an allyl group, and n is an integer of 3 or 4 provided that when n is 3, R is not a hydrogen atom or lower alkyl group, have a woody, green and earthy odor and may be prepared according to one of the following reaction formulae: ##STR2## where R.sub.1 represents a lower alkyl group or allyl group, M represents MgX or lithium atom, n is a value of 3 or 4, and X represents a halogen atom. ##STR3## The derivatives (I) may be blended with other perfumes to give perfume compositions and thus obtained compositions can be widely applied to various articles which require aromatizing such as perfumes, soaps, shampoos, hair rinses, cosmetics, hair sprays and the like.
    Type: Grant
    Filed: February 6, 1986
    Date of Patent: December 23, 1986
    Assignee: Kao Corporation
    Inventors: Kiyoshi Matsumoto, Yoshiaki Fujikura, Motoki Nakajima
  • Patent number: 4626381
    Abstract: Process for the preparation of an isomeric mixture of cis- and trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol according to a three-step pathway starting from trimethylcyclohexanone.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: December 2, 1986
    Assignee: Firmenich SA
    Inventor: Karl-Heinrich Schulte-Elte
  • 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: 4588849
    Abstract: Process for the preparation of an isomeric mixture of cis- and trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol according to a three-step pathway starting from trimethylcyclohexanone.
    Type: Grant
    Filed: February 28, 1984
    Date of Patent: May 13, 1986
    Assignee: Firmenich SA
    Inventor: Karl-Heinrich Schulte-Elte
  • Patent number: 4560811
    Abstract: Novel methods for making chlorohydrins are provided using a Lewis acid catalyst with an olefin and peroxy compound or where an enantiomer is desired, a Lewis acid catalyst in combination with a chiral alcohol, particularly glycol, and a combination of a peroxy compound and alkenol. In certain situations, an epoxide may be employed.
    Type: Grant
    Filed: January 18, 1984
    Date of Patent: December 24, 1985
    Assignee: Massachusetts Institute of Technology
    Inventors: Karl B. Sharpless, Roy A. Johnson
  • 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: 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: 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: 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: 4343955
    Abstract: An improved method for selectively hydrogenating an alkylphenol to produce the corresponding cis-alkylcyclohexanol by employing a solid catalyst is disclosed. The catalyst useful in this method is a ruthenium catalyst supported on an alumina carrier. This catalyst exhibits excellent reactivity, selectivity and durability in the catalytic hydrogenation compared to conventional rhodium or ruthenium catalysts, such as ruthenium oxide and ruthenium catalysts supported on carbon. The alkylcyclohexanol product contains so much cis-isomer that it is suitable as such for use as an intermediate for the synthesis of varous chemicals, such as perfumes.
    Type: Grant
    Filed: March 6, 1979
    Date of Patent: August 10, 1982
    Assignees: Shin-Etsu Chemical Co., Ltd., Sankio Chemical Co., Ltd.
    Inventors: Mituyoshi Oshima, Jun Yoshimoto
  • Patent number: 4326997
    Abstract: Alicyclic ketone and alcohol derivatives having the structure: ##STR1## wherein the dotted line represents a carbon-carbon double bond or a carbon-carbon single bond; wherein Z is ##STR2## and wherein each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 is hydrogen or lower alkyl are useful as odor-modifying ingredients in perfumes and perfumed products and as flavor-modifying ingredients in foodstuffs and tobacco products.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: April 27, 1982
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Robert G. Eilerman, John M. Yurecko, Jr.
  • Patent number: 4307255
    Abstract: Disclosed are novel cyclic terpenoid amines which can be prepared by cyclizing the corresponding acyclic terpenoid amine.
    Type: Grant
    Filed: March 14, 1980
    Date of Patent: December 22, 1981
    Assignee: SCM Corporation
    Inventors: Bernard J. Kane, Richard A. Von Genk
  • Patent number: 4290961
    Abstract: Catalytic reduction of carbonyl compounds by transfer of hydrogen from alcohols to aliphatic, alicyclic, aromatic, homo- and heterocyclic ketones or aldehydes, catalyzed by rhodium or iridium complexes, characterized in that a primary or secondary alcohol of formula (I) or a glycol: ##STR1## is reacted with a ketonic compound of formula (II): ##STR2## in which R and R' and, respectively, R" and R'", optionally linked with each other according to homo- or heterocycles, indifferently represent a hydrogen atom or a hydrocarbyl group having up to 30 atoms of carbon, also substituted, provided that at least one of symbols R" and/or R'" is different respectively from R and/or R', in the presence of a complex catalyst of rhodium or of iridium selected from those having formulas (III) and (IV): ##STR3## wherein: M is selected from Rh and Ir;Chel is a chelating bidentate nitrogenous compound;L-L is a molecule of a preferably non-conjugated diolefin or two molecules of a monoolefin;X.sup.
    Type: Grant
    Filed: March 7, 1980
    Date of Patent: September 22, 1981
    Assignee: Montedison S.p.A.
    Inventors: Giovanni Mestroni, Grazia Zassinovich, Annamaria Camus
  • Patent number: 4277618
    Abstract: Novel odorants, having the formula ##STR1## wherein R represents sec. butyl, tert. butyl or cyclohexyl. A process for preparing the novel odorants from novel intermediates and fragrance compositions containing the odorants are also taught.
    Type: Grant
    Filed: December 4, 1978
    Date of Patent: July 7, 1981
    Assignee: Givaudan Corporation
    Inventors: Daniel Helmlinger, Peter Naegeli
  • Patent number: 4220795
    Abstract: Novel C15 cyclobutyl analogs or derivatives of prostaglandins of the E-, A- and F-classes are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties such as platelet antiaggregating agents, gastric antisecretory agents and brochodilating agents.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: September 2, 1980
    Assignee: Miles Laboratories, Inc.
    Inventors: Harold C. Kluender, Henry C. Arndt
  • 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: 4156101
    Abstract: Process for the telomerization of olefins with secondary alcohols comprising admixing a secondary alcohol telogen with a mono-olefinically unsaturated hydrocarbon taxogen in catalytically effective amounts of a free radical generating initiator in a reaction zone, the telogen to taxogen molar ratio in the reaction zone being greater than about 1:1 as measured on the effluent stream from the reaction zone, at a temperature ranging from about 125.degree. C. to about 275.degree. C. and that a pressure varying from about 2000 psi to about 10,000 psi.
    Type: Grant
    Filed: March 20, 1974
    Date of Patent: May 22, 1979
    Assignee: Dart Industries Inc.
    Inventors: Michael Erchak, George E. Cremeans, Elmer J. Bradbury