Cyclohexanol Per Se Patents (Class 568/835)
  • Patent number: 6160183
    Abstract: 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: Grant
    Filed: February 8, 1999
    Date of Patent: December 12, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Joe Douglas Druliner, Norman Herron, Kostantinos Kourtakis
  • Patent number: 6156933
    Abstract: 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: Grant
    Filed: February 18, 1999
    Date of Patent: December 5, 2000
    Assignees: Degussa-Huls AG, Thomas Swan & Co. Ltd.
    Inventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland
  • Patent number: 6074708
    Abstract: 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: Grant
    Filed: December 22, 1998
    Date of Patent: June 13, 2000
    Assignees: Sharp Kabushiki Kaisha, Nippon Kayaku Co., Ltd.
    Inventors: Noriaki Onishi, Aya Miyazaki, Daisaku Matsunaga, Touru Ozaki
  • Patent number: 6034283
    Abstract: 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: Grant
    Filed: July 8, 1998
    Date of Patent: March 7, 2000
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Masakazu Ban, Mineyuki Iwasaki
  • Patent number: 5977402
    Abstract: 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: Grant
    Filed: April 22, 1998
    Date of Patent: November 2, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masahito Sekiguchi, Shin Tanaka
  • Patent number: 5959153
    Abstract: 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: Grant
    Filed: March 11, 1998
    Date of Patent: September 28, 1999
    Assignee: DSM N.V.
    Inventors: Ubaldus F. Kragten, Henricus A. C. Baur
  • Patent number: 5942645
    Abstract: 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: Grant
    Filed: February 3, 1997
    Date of Patent: August 24, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Rutter, Thomas Ruhl, Boris Breitscheidel, Jochem Henkelmann, Thomas Wettling
  • Patent number: 5905173
    Abstract: 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: Grant
    Filed: October 11, 1996
    Date of Patent: May 18, 1999
    Assignee: DSM NV
    Inventors: Ubaldus F. Kragten, Henricus A.C. Baur, Johannes G.H.M. Housmans
  • Patent number: 5856590
    Abstract: 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: Grant
    Filed: March 7, 1997
    Date of Patent: January 5, 1999
    Assignee: Takasago International Corporation
    Inventors: Makoto Emura, Takaaki Toyoda, Nobuo Seido, Ryoji Noyori, Takao Ikariya, Takeshi Ohkuma
  • Patent number: 5853613
    Abstract: The present invention describes liquid crystal compounds which are suitable for use in liquid crystal devices including those which exploit the electroclinic effect.
    Type: Grant
    Filed: January 16, 1997
    Date of Patent: December 29, 1998
    Assignee: Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: John William Goodby, Kenneth Johnson Toyne, Michael Hird, Stephen John Lock
  • Patent number: 5767328
    Abstract: 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: Grant
    Filed: December 19, 1996
    Date of Patent: June 16, 1998
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shigeru Ono, Mineyuki Iwasaki
  • Patent number: 5756849
    Abstract: 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: Grant
    Filed: March 22, 1996
    Date of Patent: May 26, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Gerard Forat, Jean-Manuel Mas, Laurent Saint-Jalmes
  • Patent number: 5728890
    Abstract: 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: Grant
    Filed: January 30, 1996
    Date of Patent: March 17, 1998
    Assignee: Ube Industries, Ltd.
    Inventors: Toshikazu Hamamoto, Mitsuo Yamanaka, Takato Nakamura, Tetsuro Shimano
  • Patent number: 5726321
    Abstract: 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: Grant
    Filed: March 22, 1996
    Date of Patent: March 10, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Bittins, Marc Heider, Martin Schmidt-Radde, Jochen Kellenbenz, Kurt Josef Wagner, Peter Zehner, Stefan Berg
  • Patent number: 5672778
    Abstract: 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: Grant
    Filed: August 26, 1996
    Date of Patent: September 30, 1997
    Assignee: Sun Company, Inc. (R & M)
    Inventors: James E. Lyons, Paul E. Ellis, Jr., Manoj V. Bhinde
  • Patent number: 5585527
    Abstract: 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: Grant
    Filed: October 31, 1994
    Date of Patent: December 17, 1996
    Assignee: UOP
    Inventor: Terry L. Marker
  • Patent number: 5550301
    Abstract: 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: Grant
    Filed: March 3, 1995
    Date of Patent: August 27, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Manoj V. Bhinde, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5475158
    Abstract: 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: Grant
    Filed: December 1, 1993
    Date of Patent: December 12, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Krug, Rolf Fischer, Rolf Pinkos
  • Patent number: 5403964
    Abstract: 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: Grant
    Filed: January 27, 1994
    Date of Patent: April 4, 1995
    Assignee: Exxon Research & Engineering Co.
    Inventors: Ramzi Y. Saleh, Joel R. Livingston, Jr., Michael Siskin, Glen B. Brons
  • Patent number: 5395976
    Abstract: 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: Grant
    Filed: December 10, 1993
    Date of Patent: March 7, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Scharschmidt, Christine Mendoza-Frohn, Hans-Josef Buysch, Rainer Klotzbucher
  • Patent number: 5395988
    Abstract: 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: Grant
    Filed: April 4, 1994
    Date of Patent: March 7, 1995
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Manoj V. Bhinde, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5334768
    Abstract: 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: Grant
    Filed: February 3, 1993
    Date of Patent: August 2, 1994
    Assignee: DSM N.V.
    Inventors: Johannes G. van Hinsberg, Cornelis G. M. van de Moesdijk, Ivo Spaargaren, Otto E. Sielcken
  • Patent number: 5302762
    Abstract: 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: Grant
    Filed: March 17, 1993
    Date of Patent: April 12, 1994
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Kunihiko Yamashita, Hideaki Obana, Tadashi Kai
  • Patent number: 5298665
    Abstract: 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: Grant
    Filed: March 15, 1993
    Date of Patent: March 29, 1994
    Assignee: DSM N.V.
    Inventors: Ludovicus H. W. Janssen, Peter Hoogendoorn, Ubaldus F. Kragten, Henricus A. C. Baur
  • Patent number: 5258555
    Abstract: 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: Grant
    Filed: October 6, 1992
    Date of Patent: November 2, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Pinkos, Rolf Fischer
  • Patent number: 5208392
    Abstract: 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: Grant
    Filed: April 27, 1992
    Date of Patent: May 4, 1993
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kyu-Wan Lee, Ki-Won Jun, Eun-Kyung Shim
  • Patent number: 5202502
    Abstract: 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: Grant
    Filed: March 23, 1992
    Date of Patent: April 13, 1993
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5169993
    Abstract: 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: Grant
    Filed: August 19, 1991
    Date of Patent: December 8, 1992
    Assignee: Shell Research Limited
    Inventor: Paul H. Briner
  • Patent number: 5160498
    Abstract: 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: Grant
    Filed: December 20, 1991
    Date of Patent: November 3, 1992
    Assignee: Firmenich S.A.
    Inventor: Robert M. Weinstein
  • Patent number: 5120886
    Abstract: 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: Grant
    Filed: July 9, 1991
    Date of Patent: June 9, 1992
    Assignee: Sun Refining and Marketing Company
    Inventors: James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5043486
    Abstract: 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: Grant
    Filed: August 23, 1990
    Date of Patent: August 27, 1991
    Assignee: Exxon Research and Engineering Company
    Inventors: Michael Siskin, Glen B. Brons, Ramzi Y. Saleh, Stephen N. Vaughn
  • Patent number: 5041682
    Abstract: 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: Grant
    Filed: September 19, 1988
    Date of Patent: August 20, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Hartig, Armin Stoessel, Ekhart Lucas
  • Patent number: 5015787
    Abstract: 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: Grant
    Filed: April 10, 1989
    Date of Patent: May 14, 1991
    Assignee: Allied-Signal Inc.
    Inventor: Jan F. Van Peppen
  • Patent number: 5004837
    Abstract: 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: Grant
    Filed: October 20, 1989
    Date of Patent: April 2, 1991
    Assignee: Stamicarbon B.V.
    Inventors: Henricus A. C. Baur, Ubaldus F. Kragten
  • 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: 4990688
    Abstract: 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: Grant
    Filed: July 21, 1989
    Date of Patent: February 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Gosch, Rolf Fischer
  • Patent number: 4982018
    Abstract: 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 cyclohe
    Type: Grant
    Filed: August 30, 1989
    Date of Patent: January 1, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Gosch, Rolf Fischer, Hermann Luyken
  • 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: 4978430
    Abstract: 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: Grant
    Filed: July 24, 1989
    Date of Patent: December 18, 1990
    Assignee: UBE Industries, Ltd.
    Inventors: Kanji Nakagawa, Yoshio Asakura, Shigeru Yamamoto, Kohei Ninomiya, Masayuki Kinouchi
  • Patent number: 4960960
    Abstract: 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: Grant
    Filed: October 5, 1988
    Date of Patent: October 2, 1990
    Assignee: Davy McKee (London) Limited
    Inventors: George E. Harrison, John R. Hensman
  • 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: 4927974
    Abstract: 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: Grant
    Filed: April 6, 1989
    Date of Patent: May 22, 1990
    Assignee: Stamicarbon B.V.
    Inventors: Paul C. van Geem, Franciscus T. B. van den Brink
  • 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: 4879422
    Abstract: 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: Grant
    Filed: June 27, 1988
    Date of Patent: November 7, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamio Shirafuji, Kiyomi Sakai
  • Patent number: 4849550
    Abstract: 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: Grant
    Filed: March 24, 1988
    Date of Patent: July 18, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamio Shirafuji, Itaru Kawata
  • Patent number: 4814511
    Abstract: 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: Grant
    Filed: October 23, 1987
    Date of Patent: March 21, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerald Neubauer, Rolf Schnabel, Juergen Hartig, Josef Ritz
  • Patent number: 4801719
    Abstract: 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: Grant
    Filed: June 8, 1987
    Date of Patent: January 31, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Konrad Oertle, Hansjurg Wetter
  • 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: 4720592
    Abstract: 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: Grant
    Filed: September 5, 1986
    Date of Patent: January 19, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Usamah N. Besmar, John B. Lyon, Francis J. Miller, Michael T. Musser
  • 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