Cyclohexanol Per Se Patents (Class 568/835)
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Patent number: 6160183Abstract: A catalytic process is disclosed for oxidizing cycloalkanes directly to form, in a single step, a mixture containing the corresponding alcohol and ketone. In particular, the invention relates to oxidizing a cycloalkane by contacting it with a source of oxygen and a catalytic amount of a heterogeneous catalyst. The catalysts of the invention include gold (including gold sol-gel compounds) and sol-gel compounds containing particular combinations of Cr, Co, Zr, Ta, Si, Mg, Nb, Al and Ti, wherein certain of those metals have been combined with an oxide, such as an inorganic matrix of hydroxides or oxides, or combinations thereof. The catalysts may also optionally be supported on a suitable support member.Type: GrantFiled: February 8, 1999Date of Patent: December 12, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Joe Douglas Druliner, Norman Herron, Kostantinos Kourtakis
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Patent number: 6156933Abstract: Process for the selective hydrogenation of alphatic or aromatic substrates under supercritical or near critical conditions. Hydrogenation is effected using a heterogeneous catalyst in a continuous flow reactor containing a supercritical or near critical reaction medium and selectively of product formation is achieved by varying one or more of the temperature, pressure, catalyst and flow rate.Type: GrantFiled: February 18, 1999Date of Patent: December 5, 2000Assignees: Degussa-Huls AG, Thomas Swan & Co. Ltd.Inventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland
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Patent number: 6074708Abstract: A photoinitiator is represented by general formula (I): ##STR1## where n is an integer of 1 or greater; A and B are each a trans cyclohexane ring or a benzene ring, the benzene ring being allowed to include a fluorine atom or a methyl group as a substituent, the benzene ring adjacent to a carbonyl group being allowed to include a fluorine atom or a methyl group as a substituent; p and q are each 0 or 1, p and q are not simultaneously 0; X is an alkyl group of C.sub.1 through C.sub.3 or hydrogen atom, Y is a methyl group, ethyl group or alkoxy group of C.sub.1 through C.sub.3, and Z is a methyl group, ethyl group, alkyl-substituted phenyl group or a group represented by general formula (II), Y and Z being allowed to bonded together to form a ring: ##STR2## where A, B, n, p and q are identical with those in general formula (I).Type: GrantFiled: December 22, 1998Date of Patent: June 13, 2000Assignees: Sharp Kabushiki Kaisha, Nippon Kayaku Co., Ltd.Inventors: Noriaki Onishi, Aya Miyazaki, Daisaku Matsunaga, Touru Ozaki
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Patent number: 6034283Abstract: A process for producing a cyclic alcohol by a catalytic hydration reaction of a starting cyclic olefin represented by the following formula (1) and water:C.sub.s H.sub.2s-2-t R.sub.t (1)wherein R is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a phenyl group or a cyclohexyl group; s is an integer of 5 to 12; and t is an integer of 1 to 4, which comprises supplying a part or the whole of a residue left after separation of said cyclic alcohol from an oil phase containing said cyclic alcohol, unreacted cyclic olefin and impurities having a boiling point between the boiling point of said starting cyclic olefin and that of said cyclic alcohol to a distillation column(s), and recycling the unreacted cyclic olefin obtained after removal of said impurities.Type: GrantFiled: July 8, 1998Date of Patent: March 7, 2000Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Masakazu Ban, Mineyuki Iwasaki
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Patent number: 5977402Abstract: 4-tert.-Butylcyclohexanol having a larger content of its cis-isomer is prepared by hydrogenating 4-tert.-butylphenol in a solvent in the presence of a rhodium catalyst and a compound selected from the group consisting of hydrogen chloride and (anhydrous) sulfuric acid. Furthermore, 4-tert.-butylcyclohexanol obtained by the above hydrogenation is acetylated to give 4-tert.-butylcyclohexyl acetate.Type: GrantFiled: April 22, 1998Date of Patent: November 2, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Masahito Sekiguchi, Shin Tanaka
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Patent number: 5959153Abstract: Process for decomposing a mixture containing cycloalkylhydroperoxide, which mixture includes an organic phase and an aqueous phase wherein, during the decomposition, at least one compound is present which meets the following parameters:A>-0.5 and B>-1.0 (1)A and B being dependent on T.sub.b, .rho., n.sub.d, .epsilon..sub.r, .delta..sub.d, .delta..sub.p, .delta..sub.h, .delta., .mu. and E.sub.T(30), where T.sub.b is the normal boiling point (.degree. C.), .rho. is the density measured at 25.degree. C. (kg/m.sup.3), n.sub.d is the refractive index (-), .epsilon..sub.r is the relative dielectric constant (-), .delta..sub.d is the Hansen solubility parameter for a dispersion (MPa.sup.1/2), .delta..sub.p is the Hansen solubility parameter for polarity (MPa.sup.1/2), .delta..sub.h is the Hansen solubility parameter for hydrogen bridges (MPa.sup.1/2), .delta. is the Scatchard-Hildebrant solubility parameter (MPa.sup.1/2), .mu. is the dipole moment (Debey), and E.sub.Type: GrantFiled: March 11, 1998Date of Patent: September 28, 1999Assignee: DSM N.V.Inventors: Ubaldus F. Kragten, Henricus A. C. Baur
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Patent number: 5942645Abstract: A process for hydrogenating aromatic compounds in which at least one hydroxyl group is bonded to an aromatic ring comprises bringing at least one of these compounds into contact with free hydrogen in the presence of a catalyst, wherein the catalyst comprises ruthenium and, if desired, at least one metal of transition groups I, VII and VIII in an amount of from 0.01 to 30% by weight, preferably from 0.2 to 15% by weight, based on the total weight of the catalyst, applied to a support, where the support has a mean pore diameter of at least 0.1 .mu.m, preferably at least 0.5 .mu.m, and a surface area of at most 15 m.sup.2 /g, preferably at most 10 m.sup.2 /g.Type: GrantFiled: February 3, 1997Date of Patent: August 24, 1999Assignee: BASF AktiengesellschaftInventors: Heinz Rutter, Thomas Ruhl, Boris Breitscheidel, Jochem Henkelmann, Thomas Wettling
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Patent number: 5905173Abstract: The invention relates to a process for decomposing a mixture containing cycloalkyl hydroperoxide with an aqueous phase containing alkali metal hydroxide where, besides the alkali metal hydroxide, there is also at least 10 wt. % of the aqueous phase of one or more alkali metal salts. The alkali metal salts are preferably alkali metal carbonates, or alkali metal salts of mono- and poly-carboxylic acids, with the carboxylic acid moiety containing 1-24 carbon atoms.Type: GrantFiled: October 11, 1996Date of Patent: May 18, 1999Assignee: DSM NVInventors: Ubaldus F. Kragten, Henricus A.C. Baur, Johannes G.H.M. Housmans
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Patent number: 5856590Abstract: A process whereby 4-t-butylcyclohexanol with a high content of the cis-isomer, which is useful as a perfume ingredient, can be economically produced on an industrially available scale at a low cost. The process comprises hydrogenating 4-t-butylcyclohexanone by using a specific ruthenium-phosphine complex as a catalyst in the presence of a base containing an alkali metal and an alkylenediamine having from 1 to 6 carbon atoms.Type: GrantFiled: March 7, 1997Date of Patent: January 5, 1999Assignee: Takasago International CorporationInventors: Makoto Emura, Takaaki Toyoda, Nobuo Seido, Ryoji Noyori, Takao Ikariya, Takeshi Ohkuma
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Patent number: 5853613Abstract: The present invention describes liquid crystal compounds which are suitable for use in liquid crystal devices including those which exploit the electroclinic effect.Type: GrantFiled: January 16, 1997Date of Patent: December 29, 1998Assignee: Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: John William Goodby, Kenneth Johnson Toyne, Michael Hird, Stephen John Lock
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Patent number: 5767328Abstract: A process for producing a cyclic alcohol which comprises subjecting a cyclic olefin represented by the formula: C.sub.n H.sub.2n-2-m R.sub.m (wherein R represents a hydrogen atom, an alkyl group of 1-4 carbon atoms, a phenyl group or a cyclohexyl group, n represents an integer of 5-12, and m represents an integer of 1-4) to a catalytic hydration reaction with water in the presence of a crystalline aluminosilicate having a primary particle diameter of 0.5 .mu.m or less as a catalyst, extracting the resulting liquid of an oil phase containing a cyclic alcohol and the crystalline aluminosilicate, evaporating the liquid and feeding the vapor to a rectifying column and/or filtering the liquid and feeding the filtrate to the rectifying column, thereby to adjust the concentration of the crystalline aluminosilicate contained in the liquid in the rectifying column to 1000 ppm by weight or less, and subjecting the liquid to distillation to separate the cyclic alcohol.Type: GrantFiled: December 19, 1996Date of Patent: June 16, 1998Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Shigeru Ono, Mineyuki Iwasaki
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Patent number: 5756849Abstract: The invention relates to a process and a nucleophilic reagent which is useful for grafting a substituted difluoromethyl group onto a compound containing at least one electrophilic function, characterized in that it comprises:a) a fluorocarboxylic acid of formula Ew--CF.sub.2 --COOH where Ew represents an electron-withdrawing atom or group, at least partially salified with an organic or inorganic cation, andb) a polar aprotic solvent;and in that the content of releasable protons carried by its various components, including their impurities, is at most equal to half the initial molar concentration of the said fluorocarboxylic acid.Type: GrantFiled: March 22, 1996Date of Patent: May 26, 1998Assignee: Rhone-Poulenc ChimieInventors: Gerard Forat, Jean-Manuel Mas, Laurent Saint-Jalmes
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Patent number: 5728890Abstract: A cycloalkylhydroperoxide, preferably having a C.sub.5-20 cycloalkyl group, is decomposed by bringing it into contact with a ruthenium complex of the formula:?RuCl.sub.2 L.sub.n !.sub.m (I)wherein L=a neutral ligand, n=1-4 and m.gtoreq.1, for example, ?RuCl.sub.2 (PPh.sub.3).sub.3 !, to produce a cycloalkanol and cycloalkanone.Type: GrantFiled: January 30, 1996Date of Patent: March 17, 1998Assignee: Ube Industries, Ltd.Inventors: Toshikazu Hamamoto, Mitsuo Yamanaka, Takato Nakamura, Tetsuro Shimano
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Patent number: 5726321Abstract: Process for carrying out gas/liquid reactions at from (-50.degree.) to 300.degree. C. and from 0.1 to 100 bar by carrying out the reaction in the absence of a continuous gas phase, and, as a special case, a process for the batchwise reaction of acetylene in the liquid phase at from 0.degree. to 300.degree. C. and from 2 to 30 bar, in which acetylene is introduced a) in the absence of a continuous gas phase and b) under isobaric conditions to a degree of saturation of from 5 to 100%.Type: GrantFiled: March 22, 1996Date of Patent: March 10, 1998Assignee: BASF AktiengesellschaftInventors: Klaus Bittins, Marc Heider, Martin Schmidt-Radde, Jochen Kellenbenz, Kurt Josef Wagner, Peter Zehner, Stefan Berg
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Patent number: 5672778Abstract: The invention comprises a method for the catalytic conversion of alkanes and alkylhydroperoxides to oxygenates, particularly alcohols, comprising the oxidation of alkanes to yield alkylhydroperoxides, alcohols, other reaction products and unreacted alkane, and the decomposition of said alkylhydroperoxides to form alcohols and oxygen. Decomposition of the alkylhydroperoxide in the presence of unreacted alkane increases the yield of alcohol. The process further comprises drying of the reaction mixture comprising alkylhydroperoxide. Suitable catalysts for the process of the invention comprise metal containing catalysts, including metal organic ligand catalysts such as unsubstituted and substituted metal complexes of porphyrins, phthalocyanines and acetylacetonates.Type: GrantFiled: August 26, 1996Date of Patent: September 30, 1997Assignee: Sun Company, Inc. (R & M)Inventors: James E. Lyons, Paul E. Ellis, Jr., Manoj V. Bhinde
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Patent number: 5585527Abstract: A process for separating a first component of a process stream from a second component of a process stream in a single vessel has been developed. The separation process uses an apparatus having a distillation zone to separate a first component from a second component of a process stream, thereby producing a distillation zone overhead stream enriched in the first component, and a membrane separation zone containing a membrane capable of selectively removing additional amounts of the second component from the distillation overhead stream. The benefit is the production of a high purity process at lower capital equipment costs.Type: GrantFiled: October 31, 1994Date of Patent: December 17, 1996Assignee: UOPInventor: Terry L. Marker
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Patent number: 5550301Abstract: Organic hydroperoxides are decomposed by drying a reaction mixture containing the organic hydroperoxide and an organic solvent such that said dried reaction mixture comprises approximately 1 weight percent or less of water and contacting the dried reaction mixture with a metal organic ligand catalyst under hydroperoxide decomposition conditions. An organic co-solvent for the hydroperoxide may also be used. Particularly effective catalysts are cobalt acetylacetonates and ruthenium acetylacetonates and combinations thereof.Type: GrantFiled: March 3, 1995Date of Patent: August 27, 1996Assignee: Sun Company, Inc. (R&M)Inventors: Manoj V. Bhinde, James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5475158Abstract: A process for the preparation of cycloalkanols by the hydrolysis of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters, which comprises the following steps:a) reaction of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters with water at a temperature of from 30.degree. to 250.degree. in the liquid phase yielding a reaction mixture consisting of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters, cycloalkanol, C.sub.1 -C.sub.4 fatty acids, and water.b) separation of the reaction mixture obtained in stage a) at a temperature of from 0.degree. to 200.degree. C. into a top phase consisting substantially of cycloalkanol and cycloalkyl C.sub.1 -C.sub.4 fatty acid esters and a bottom phase consisting substantially of water and C.sub.1 -C.sub.4 fatty acids.c) separation of cycloalkanol from the top phase obtained in stage b) by distillation and recycling unconverted cycloalkyl C.sub.1 -C.sub.4 fatty acid esters to stage a).Type: GrantFiled: December 1, 1993Date of Patent: December 12, 1995Assignee: BASF AktiengesellschaftInventors: Thomas Krug, Rolf Fischer, Rolf Pinkos
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Patent number: 5403964Abstract: The present invention relates to enhanced process for converting certain ethers, such as sec-butyl ether and isopropyl ether to their corresponding reaction products in the presence of water. This may be accomplished by adding a rate enhancing surfactant, such as an anionic or cationic surfactant to a mixture of the ether and water, preferably least about 10.sup.-5 molar surfactant. Under those conditions the reaction shows an increase in reaction rate over the rate of the process wherein surfactant is not used.Type: GrantFiled: January 27, 1994Date of Patent: April 4, 1995Assignee: Exxon Research & Engineering Co.Inventors: Ramzi Y. Saleh, Joel R. Livingston, Jr., Michael Siskin, Glen B. Brons
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Patent number: 5395976Abstract: In the hydrogenation of phenol with H.sub.2 over Pd supported catalysts, the ratio of the products formed, cyclohexanone and cyclohexanol, can be predetermined by specific treatment of the catalysts during the initial activation and regeneration by O.sub.2 pretreatment and H.sub.2 treatment, the following time/temperature conditions being used:a) Cyclohexanone:cyclohexanol=85:15 to 98:2a1) for initial activation, no O.sub.2 pretreatment and H.sub.2 treatment for 50-10 hours at 300.degree.-500.degree. C.;a2) for regeneration, O.sub.2 pretreatment for 30-0.5 hours at 220.degree.-380.degree. C. and H.sub.2 treatment for 2-6 hours at 150.degree.-250.degree. C.;b) Cyclohexanone:cyclohexanol=30:70 to below 85:15b1) for initial activation, O.sub.2 pretreatment for 40-3 hours at 250.degree.-500.degree. C. and H.sub.2 treatment for 2-6 hours at 150.degree.-250.degree. C.;b2) for regeneration, O.sub.2 pretreatment for 30-0.5 hours at 380.degree.-600.degree. C. and H.sub.2 treatment for 2-6 hours at 150.degree.-250.Type: GrantFiled: December 10, 1993Date of Patent: March 7, 1995Assignee: Bayer AktiengesellschaftInventors: Jurgen Scharschmidt, Christine Mendoza-Frohn, Hans-Josef Buysch, Rainer Klotzbucher
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Patent number: 5395988Abstract: Organic hydroperoxides are decomposed by drying a reaction mixture containing the organic hydroperoxide and an organic solvent and contacting the dried reaction mixture with a metal organic ligand catalyst under hydroperoxide decomposition conditions. An organic co-solvent for the hydroperoxide may also be used.Type: GrantFiled: April 4, 1994Date of Patent: March 7, 1995Assignee: Sun Company, Inc. (R&M)Inventors: Manoj V. Bhinde, James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5334768Abstract: The invention relates to a process for the preparation of cycloalkanone and optionally cycloalkanol by causing a mixture containing cycloalkylhydroperoxide to react with cycloalkene under the influence of a catalyst, characterised in that the reaction is carried out with a short measure of cycloalkene relative to the cycloalkylhydroperoxide, under such conditions that virtually all of the cycloalkene reacts to cycloalkene oxide and optionally cycloalkanol and/or cycloalkanone, after which the mixture, optionally after decomposition of cycloalkylhydroperoxide and distillation of cycloalkane, is subjected to a first separation, in which cycloalkene oxide--and optionally other components--is separated, after which the cycloalkene oxide in the separated mixture is isomerised to substantially cycloalkanone, after which the cycloalkanone obtained--and optionally cycloalkanol--is recovered.Type: GrantFiled: February 3, 1993Date of Patent: August 2, 1994Assignee: DSM N.V.Inventors: Johannes G. van Hinsberg, Cornelis G. M. van de Moesdijk, Ivo Spaargaren, Otto E. Sielcken
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Patent number: 5302762Abstract: Disclosed is a method for hydrating a cycloolefin, in which the hydration is conducted in a reaction system comprising a continuous aqueous phase including water and a crystalline aluminosilicate catalyst suspended therein and an oil phase including a cycloolefin, while dispersing the oil phase as globules having a specific diameter. By the method of the present invention, not only can a cyclic alcohol be produced at high selectivity and in high yield, but the activity of the catalyst can also be stably maintained at a high level for a prolonged period of time, and the produced cyclic alcohol can be readily separated.Type: GrantFiled: March 17, 1993Date of Patent: April 12, 1994Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Kunihiko Yamashita, Hideaki Obana, Tadashi Kai
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Patent number: 5298665Abstract: The invention relates to a process for preparing an alkanone and/or alkanol by oxidizing an alkane with 3-30 C-atoms, using oxygen, to form an alkyl hydroperoxide, followed by a decomposition of the resulting alkyl hydroperoxide in the presence of a metal compound immobilized on a carrier, which carrier carries aliphatic or aromatic amine groups or sulphide groups. The process is preferably applied to cycloalkanes.Type: GrantFiled: March 15, 1993Date of Patent: March 29, 1994Assignee: DSM N.V.Inventors: Ludovicus H. W. Janssen, Peter Hoogendoorn, Ubaldus F. Kragten, Henricus A. C. Baur
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Patent number: 5258555Abstract: A process for the preparation of a cycloalkanol by the reaction of a cycloolefin with water in the presence of a solid acidic catalyst at a temperature of from 50.degree. to 280.degree. C. and under superatmospheric pressure, provided that the temperature and pressure conditions suffice for the formation of a liquid phase comprising water and cycloolefin, wherein a mixture of water and cycloolefin is passed through a fixed bed of solid acidic catalyst with the proviso that no visible liquid phase forms in the bed of solid acidic catalyst.Type: GrantFiled: October 6, 1992Date of Patent: November 2, 1993Assignee: BASF AktiengesellschaftInventors: Rolf Pinkos, Rolf Fischer
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Patent number: 5208392Abstract: The present invention provides a novel Fe-Pd catalyst prepared by impregnating, either together or respectively, an iron source compound and a palladium source compound onto a carrier selected from the group consisting of silica, alumina and silica-alumina, and drying and calcining said Fe-Pd impregnated carrier in a flow of air or H.sub.2 /N.sub.2 ; and a method for preparing a mixture of cyclohexanol and cyclohexanone by selectively oxidizing cyclohexane in a reaction medium provided with hydrogen and oxygen gases in the presence of said Fe-Pd catalyst.Type: GrantFiled: April 27, 1992Date of Patent: May 4, 1993Assignee: Korea Research Institute of Chemical TechnologyInventors: Kyu-Wan Lee, Ki-Won Jun, Eun-Kyung Shim
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Patent number: 5202502Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo, and a process of using such for the production of optically active alcohols.Type: GrantFiled: March 23, 1992Date of Patent: April 13, 1993Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5169993Abstract: The invention provides cyclohexenol derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; and R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group, with the provisos that when R.sup.1, R.sup.2 and R.sup.3 all represent a hydrogen atom then n is not 0 and, when R.sup.1, R.sup.2 and R.sup.3 all represent a hydrogen atom and n is 1, R does not represent a fluorine atom substituted at the 4-position of the phenyl ring; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidal active cyclopentane derivatives.Type: GrantFiled: August 19, 1991Date of Patent: December 8, 1992Assignee: Shell Research LimitedInventor: Paul H. Briner
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Patent number: 5160498Abstract: A process for the preparation of 4-tert-butyl-cyclohexanol, comprising the hydrogenation of 4-tert-butyl-phenol or of 4-tert-butyl-cyclohexanone in the presence of a catalytic system composed of rhodium on a Al.sub.2 O.sub.3, SiO.sub.2, TiO.sub.2, SiO.sub.2.Al.sub.2 O.sub.3 or charcoal support, in combination with HBF.sub.4 or BF.sub.3.[Y].sub.n wherein Y designates a R.sub.2 O group, R being a C.sub.1 to C.sub.6 lower alkyl radical, or a CH.sub.3 CO.sub.2 H, H.sub.3 PO.sub.4 or H.sub.2 O group and index n is equal to zero, 1 or 2.Type: GrantFiled: December 20, 1991Date of Patent: November 3, 1992Assignee: Firmenich S.A.Inventor: Robert M. Weinstein
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Patent number: 5120886Abstract: Hydroperoxides are decomposed by contact with metal ligand catalysts of coordination complexes in which hydrogen in the ligand molecule has been substituted with electron-withdrawing elements or groups, for example halogen or nitro or cyano groups. Preferred catalysts are iron perhaloporphyrins.Type: GrantFiled: July 9, 1991Date of Patent: June 9, 1992Assignee: Sun Refining and Marketing CompanyInventors: James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5043486Abstract: The present invention provides for a simplified process for converting ethers into their corresponding alcohols comprising forming an aqueous mixture of the ether and at least about 50% by weight water and heating the mixture under autogeneous pressure at a temperature of from about 250.degree. to 450.degree. C., more preferably from about 250.degree. C. up to the critical temperature of water which is about 374.degree. C. Heating is continued for a period of time sufficient to convert at least about 20% by weight of the ether, usually from about 5 up to about 120 minutes, depending on temperature and the amount of water present, and the identity of the starting ether feedstock.The process may be characterized as an aquathermolysis reaction wherein the reaction proceeds in water primarily through ionic routes rather than through free radical routes.Type: GrantFiled: August 23, 1990Date of Patent: August 27, 1991Assignee: Exxon Research and Engineering CompanyInventors: Michael Siskin, Glen B. Brons, Ramzi Y. Saleh, Stephen N. Vaughn
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Patent number: 5041682Abstract: Reaction mixtures which contain cyclohexanol, cyclohexanone and cyclohexyl hydroperoxide and are obtained in the oxidation of cyclohexane with molecular oxygen, or with a gas containing this, in the liquid phase are worked up by a process in which the reaction mixture is hydrogenated in the presence of a noble metal catalyst at elevated temperatures and under superatmospheric pressure, the resulting mixture is treated with an aqueous alkali metal carbonate solution, and cyclohexanol and cyclohexanone are separated off by distillation.Type: GrantFiled: September 19, 1988Date of Patent: August 20, 1991Assignee: BASF AktiengesellschaftInventors: Juergen Hartig, Armin Stoessel, Ekhart Lucas
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Patent number: 5015787Abstract: In a process for production of cyclohexanol comprising the selective catalytic hydrogenation of phenol to a product mixture comprising a major portion of cyclohexanol and a substantially smaller portion of cyclohexanone, then distillation of said product mixture to obtain cyclohexanol containing a minor amount of cyclohexanone meeting desired specification levels; the improvement comprising adding to said product mixture an effective amount of a polyamine such as hexamethylene diamine and distilling the product mixture to obtain an improved yield of said cyclohexanol containing a minor amount of cyclohexanone.Type: GrantFiled: April 10, 1989Date of Patent: May 14, 1991Assignee: Allied-Signal Inc.Inventor: Jan F. Van Peppen
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Patent number: 5004837Abstract: The invention relates to a process for preparing a cycloalkanone and/or cycloalkanol by oxidation of a cycloalkane using oxygen to form a hydroperoxide, followed by a decomposition of the hydroperoxide, in the presence of an organic metal complex, the decomposition being carried out in the presence of a phthalocyanine or porphyrin metal complex immobilized on a carrier material.Type: GrantFiled: October 20, 1989Date of Patent: April 2, 1991Assignee: Stamicarbon B.V.Inventors: Henricus A. C. Baur, Ubaldus F. Kragten
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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: 4990688Abstract: Cyclohexanol is removed from aqueous solutions containing it and aromatic sulfonic acid by extraction using as the extractant a mixture of(a) one or more liquid aliphatic, cyloaliphatic or aromatic hydrocarbons, halohydrocarbons or ethers which are inert under extraction conditions and(b) one or more phenols.Type: GrantFiled: July 21, 1989Date of Patent: February 5, 1991Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Gosch, Rolf Fischer
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Patent number: 4982018Abstract: Cyclohexanol is removed from aqueous solutions containing it and aromatic sulfonic acids, obtained by hydrating cyclohexene in aqueous solutions of aromatic sulfonic acids at elevated temperatures and subsequent removal of excess cyclohexene, by(a) feeding the aqueous solution which contains the cyclohexanol and the aromatic sulfonic acid into the upper third of a first column and from 1 to 50 parts by weight of steam per part by weight of cyclohexanol into the bottom third of the column, withdrawing at the top of the column a vapor which consists essentially of cyclohexanol, cyclohexene and water, and obtaining as a bottom product an aqueous solution of the aromatic sulfonic acid,(b) condensing the vapor which consists essentially of cyclohexanol, cyclohexene and water and(b1) obtaining a cyclohexanol-rich phase and(b2) an aqueous phase,(c) utilizing the aqueous phase (b2) for generating the steam required in stage (a) and any remainder for the hydration of cyclohexene, and(d) distilling off from the cycloheType: GrantFiled: August 30, 1989Date of Patent: January 1, 1991Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Gosch, Rolf Fischer, Hermann Luyken
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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: 4978430Abstract: An improved method for dehydration and concentration of an aqueous solution containing an organic compound is disclosed. The solution is evaporated to produce a gaseous mixture comprising an organic compound vapor and a water vapor. The water vapor is selectively removed from the gaseous mixture by permeation through an aromatic polyimide gas separation membrane while the gaseous mixture being kept in contact with a surface on one side of the gas separation membrane at a temperature of 70.degree. C. or higher to obtain a gaseous mixture comprising the organic compound vapor and a reduced amount of a water vapor.Type: GrantFiled: July 24, 1989Date of Patent: December 18, 1990Assignee: UBE Industries, Ltd.Inventors: Kanji Nakagawa, Yoshio Asakura, Shigeru Yamamoto, Kohei Ninomiya, Masayuki Kinouchi
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Patent number: 4960960Abstract: Hydrogen is supplied first to a last hydrogenation zone, and gases recovered from the last hydrogenation zone are passed to the first hydrogenation zone of a continuous multi-zone liquid phase process for hydrogenating an organic compound to a corresponding hydrogenation product. The organic compound, with a suitable diluent or recycle hydrogenation product, flows successively through the zones beginning with the first and ending with the last hydrogenation zone to undergo hydrogenation with the hydrogenation product being recovered from the last hydrogenation zone.Type: GrantFiled: October 5, 1988Date of Patent: October 2, 1990Assignee: Davy McKee (London) LimitedInventors: George E. Harrison, John R. Hensman
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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: 4927974Abstract: The invention relates to a process for preparing cyclohexanol and/or cyclohexanone, in which cyclohexene in a feed stream containing cyclohexene, cyclohexane and benzene is hydrated into cyclohexanol and/or oxidized into cyclohexanone, the cyclohexanol and/or cyclohexanone formed is separated from the reaction mixture thus obtained and the remaining cyclohexane and benzene are recycled to a preconnected cyclohexene preparation section, part of the stream that is recycled to the cyclohexene preparation section being subjected to a dehydrogenation reaction and the remaining part to a hydrogenation reaction, and the reaction streams thus obtained being combined to form the feed stream to the hydration and/or oxidation step.Type: GrantFiled: April 6, 1989Date of Patent: May 22, 1990Assignee: Stamicarbon B.V.Inventors: Paul C. van Geem, Franciscus T. B. van den Brink
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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: 4879422Abstract: A method for producing a cycloalkanol in high yield by hydrating cycloalkene with a specific catalyst is disclosed. The catalyst is obtainable by ion-exchanging all or a part of the cations of a crystalline gallium silicate with hydrogen ions. It has a specific composition defined by the general formula and is characterized by the X-ray diffraction pattern.Type: GrantFiled: June 27, 1988Date of Patent: November 7, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Tamio Shirafuji, Kiyomi Sakai
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Patent number: 4849550Abstract: A industrially excellent method for producing a cycloalkanol by the hydration of a cycloalkene having from 4 to 8 carbon atoms with an aromatic sulfonic acid as a catalyst which comprises carrying out said hydration in the presence of a phenol.Type: GrantFiled: March 24, 1988Date of Patent: July 18, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Tamio Shirafuji, Itaru Kawata
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Patent number: 4814511Abstract: Cyclohexyl hydroperoxide containing reaction mixtures obtained by oxidation of cyclohexane with molecular oxygen or molecular oxygen containing gases in the liquid phase at from 130.degree. to 200.degree. C. and under from 5 to 125 bar are worked up by reaction with cycloolefins at elevated temperature in the presence of catalysts to react cyclohexyl hydroperoxide with cyclohexene at elevated temperatures in the presence of cyclohexene-soluble compounds of transition metals of groups 4 or 5 or 6 of the periodic table or of one or more cyclohexane-insoluble compounds of a transition metal of group 4 or 5 or 6, or in the presence of selenium, tellurium or a boride, and the resulting cyclohexene oxide at elevated temperatures to cyclohexanol in the presence of hydrogenation catalysts.Type: GrantFiled: October 23, 1987Date of Patent: March 21, 1989Assignee: BASF AktiengesellschaftInventors: Gerald Neubauer, Rolf Schnabel, Juergen Hartig, Josef Ritz
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Patent number: 4801719Abstract: Compounds of the formula Ia ##STR1## in which X and R.sup.1 to R.sup.6 are as defined in the claims, are obtainable by reacting monochlorosilanes of the formula II ##STR2## with tetrasubstituted ethylenes of the formula III ##STR3## X as Cl and Br can be replaced by ester groups of inorganic and organic acids. The compounds of the formula I and those with other ester groups are suitable especially as a protective-group reagent for hydroxyl, mercapto, carboxyl, amino and amide groups.Type: GrantFiled: June 8, 1987Date of Patent: January 31, 1989Assignee: Ciba-Geigy CorporationInventors: Konrad Oertle, Hansjurg Wetter
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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: 4720592Abstract: The reaction mixture obtained by oxidation of cyclohexane using a cobalt catalyst is extracted with water to remove undesirable oxidation products such as diacids, hydroxy acids, and cobalt catalyst. The resulting mixture is then hydrogenated using a fixed bed hydrogenation catalyst to convert cyclohexyl hydroperoxide to cyclohexanol and cyclohexanone.Type: GrantFiled: September 5, 1986Date of Patent: January 19, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Usamah N. Besmar, John B. Lyon, Francis J. Miller, Michael T. Musser
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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