Polycarbon Alkyl Group Containing Patents (Class 568/834)
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Patent number: 5057630Abstract: 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: GrantFiled: April 6, 1990Date of Patent: October 15, 1991Assignee: Glaxo Inc.Inventors: John W. Lackey, Robert A. Mook, Jr., John J. Partridge
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Patent number: 4990692Abstract: 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: GrantFiled: July 21, 1989Date of Patent: February 5, 1991Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Gosch, Rolf Fischer
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Patent number: 4982017Abstract: 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: GrantFiled: May 3, 1989Date of Patent: January 1, 1991Assignee: Metallgesellschaft AktiengesellschaftInventors: Jurgen Deberitz, Wilfried Weiss
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Patent number: 4933508Abstract: 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: GrantFiled: September 23, 1988Date of Patent: June 12, 1990Assignee: Mitsubishi Kasei CorporationInventors: Haruo Habu, Kouji Watanabe, Takeshi Matsuoka
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Patent number: 4916252Abstract: 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: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4885409Abstract: 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: GrantFiled: May 4, 1988Date of Patent: December 5, 1989Assignee: Montedison S.p.A.Inventors: Andrea Gardano, Francesco Casagrande, Marco Foa, Guido Petrini, Riccardo Barisone, Lawrence Chapoy
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Patent number: 4820879Abstract: 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: GrantFiled: June 5, 1987Date of Patent: April 11, 1989Assignee: Lithium Corporation of AmericaInventor: Vijay C. Mehta
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Patent number: 4757051Abstract: 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: GrantFiled: August 11, 1987Date of Patent: July 12, 1988Assignee: BASF AktiengesellschaftInventors: Walter Gramlich, Werner Hoffman, Ludwig Schuster
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Patent number: 4751214Abstract: 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: GrantFiled: August 6, 1987Date of Patent: June 14, 1988Assignee: BASF AktiengesellschaftInventors: Walter Gramlich, Werner Hoffmann, Klaas Jansen, Wolfgang Lengsfeld, Ludwig Schuster
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Patent number: 4720558Abstract: 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: GrantFiled: March 11, 1986Date of Patent: January 19, 1988Assignee: Bayer AktiengesellschaftInventor: Johannes Kaulen
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Patent number: 4719041Abstract: 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: GrantFiled: March 20, 1987Date of Patent: January 12, 1988Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Ulf-Armin Schaper, Siegfried Bloesl, Klaus Bruns, Benno Streschnak
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Patent number: 4711875Abstract: 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: GrantFiled: October 17, 1985Date of Patent: December 8, 1987Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Gunther Ohloff, Bernard L. Muller, Wolfgang K. Giersch
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Patent number: 4631147Abstract: 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: GrantFiled: February 6, 1986Date of Patent: December 23, 1986Assignee: Kao CorporationInventors: Kiyoshi Matsumoto, Yoshiaki Fujikura, Motoki Nakajima
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Patent number: 4626381Abstract: 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: GrantFiled: December 17, 1985Date of Patent: December 2, 1986Assignee: Firmenich SAInventor: Karl-Heinrich Schulte-Elte
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Patent number: 4617145Abstract: 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: GrantFiled: November 21, 1985Date of Patent: October 14, 1986Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, Anubhav P. S. Narula, Marie R. Hanna
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Patent number: 4588849Abstract: 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: GrantFiled: February 28, 1984Date of Patent: May 13, 1986Assignee: Firmenich SAInventor: Karl-Heinrich Schulte-Elte
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Patent number: 4560811Abstract: 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: GrantFiled: January 18, 1984Date of Patent: December 24, 1985Assignee: Massachusetts Institute of TechnologyInventors: Karl B. Sharpless, Roy A. Johnson
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Patent number: 4551564Abstract: 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: GrantFiled: October 22, 1984Date of Patent: November 5, 1985Assignee: Chemische Werke Huels, AGInventors: Werner Otte, Rudolf Nehring, Manfred zur Hausen
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Patent number: 4508918Abstract: 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: GrantFiled: November 20, 1979Date of Patent: April 2, 1985Assignee: Toray Industries, Inc.Inventors: Yutaka Yasuhara, Masaki Nishino, Seikichi Matsuhisa
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Patent number: 4371722Abstract: Disclosed are novel cyclic terpenoid amines which can be prepared by cyclizing the corresponding acyclic terpenoid amine.Type: GrantFiled: June 26, 1981Date of Patent: February 1, 1983Assignee: SCM CorporationInventors: Bernard J. Kane, Richard A. Von Genk
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Patent number: 4346240Abstract: 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: GrantFiled: September 29, 1981Date of Patent: August 24, 1982Assignee: Allied CorporationInventors: Roger A. Grey, Guido P. Pez
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Patent number: 4343955Abstract: 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: GrantFiled: March 6, 1979Date of Patent: August 10, 1982Assignees: Shin-Etsu Chemical Co., Ltd., Sankio Chemical Co., Ltd.Inventors: Mituyoshi Oshima, Jun Yoshimoto
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Patent number: 4326997Abstract: 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: GrantFiled: October 8, 1980Date of Patent: April 27, 1982Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman, John M. Yurecko, Jr.
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Patent number: 4307255Abstract: Disclosed are novel cyclic terpenoid amines which can be prepared by cyclizing the corresponding acyclic terpenoid amine.Type: GrantFiled: March 14, 1980Date of Patent: December 22, 1981Assignee: SCM CorporationInventors: Bernard J. Kane, Richard A. Von Genk
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Patent number: 4290961Abstract: 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: GrantFiled: March 7, 1980Date of Patent: September 22, 1981Assignee: Montedison S.p.A.Inventors: Giovanni Mestroni, Grazia Zassinovich, Annamaria Camus
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Patent number: 4277618Abstract: 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: GrantFiled: December 4, 1978Date of Patent: July 7, 1981Assignee: Givaudan CorporationInventors: Daniel Helmlinger, Peter Naegeli
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Patent number: 4220795Abstract: 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: GrantFiled: August 14, 1978Date of Patent: September 2, 1980Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Henry C. Arndt
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Patent number: 4212990Abstract: 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: GrantFiled: August 5, 1977Date of Patent: July 15, 1980Assignee: Toray Industries, Inc.Inventors: Yutaka Yasuhara, Masaki Nishino, Seikichi Matsuhira
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Patent number: 4156101Abstract: 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: GrantFiled: March 20, 1974Date of Patent: May 22, 1979Assignee: Dart Industries Inc.Inventors: Michael Erchak, George E. Cremeans, Elmer J. Bradbury