Carbon Monoxide Or Peroxy Containing Reactant Patents (Class 568/342)
  • Publication number: 20100137645
    Abstract: The present invention relates to a process for decomposing cyclohexylhydroperoxide into cyclohexanone, said process comprising mixing an organic feed solution comprising cyclohexylhydroperoxide with an aqueous base solution in the absence of a transition metal catalyst resulting in a mixture comprising (i) an aqueous phase and (ii) an organic phase comprising cyclohexanone and cyclohexanol.
    Type: Application
    Filed: December 16, 2005
    Publication date: June 3, 2010
    Inventor: Imre Toth
  • Patent number: 7642384
    Abstract: The present invention relates to a process for preparing cyclohexanone and cyclohexanol, said process comprising (a) neutralising acids and/or carbon dioxide present in an organic solution further comprising cyclohexylhydroperoxide by mixing the organic solution with a first aqueous base solution at a temperature of from 50 to 80° C. to form a first mixture comprising a first aqueous phase with a pH of from 8.5 to 13 and a first organic phase, (b) separating first aqueous phase from the first mixture resulting in a remaining mixture comprising first organic phase, (c) decomposing cyclohexylhydroperoxide present in said remaining mixture by mixing said remaining mixture with a second aqueous base solution at a temperature of from 60 to 110° C. to form a second mixture comprising a second aqueous phase and a second organic phase comprising cyclohexanone and cyclohexanol, (d) separating the second aqueous phase from the second organic phase at a temperature higher than 80° C.
    Type: Grant
    Filed: January 17, 2006
    Date of Patent: January 5, 2010
    Assignee: DSM IP Assets B.V.
    Inventor: Larry Walker Wyatt
  • Patent number: 7619122
    Abstract: Process for preparing cyclohexanone and cyclohexanol, said process comprising (a) neutralising acids and/or carbon dioxide present in an organic solution further comprising cyclohexylhydroperoxide by mixing the organic solution with a first aqueous base solution to form a first mixture comprising a first aqueous phase and a first organic phase, (b) separating first aqueous phase from first organic phase, (c) discharging first aqueous phase, (d) decomposing cyclohexylhydroperoxide present in said first organic phase by mixing said first organic phase with a second aqueous base solution to form a second mixture comprising a second aqueous phase and a second organic phase comprising cyclohexanone and cyclohexanol, (e) separating the second aqueous phase from the second organic phase, (f) feeding at least a portion of said separated second aqueous phase to said neutralising (a), wherein the process further comprises feeding such a portion of the first aqueous phase to the decomposing that the pH of the first aque
    Type: Grant
    Filed: January 17, 2006
    Date of Patent: November 17, 2009
    Assignee: DSM IP Assets B.V.
    Inventor: Larry Walker Wyatt
  • Publication number: 20090093638
    Abstract: The present invention relates to compositions and methods for achieving the efficient allylic oxidation of organic molecules, especially olefins and steroids, under aqueous conditions. The invention concerns the use of dirhodium (II,II) “paddlewheel complexes, and in particular, dirhodium carboximate and tert-butyl hydroperoxide as catalysts for the reaction. The use of aqueous conditions is particularly advantageous in the allylic oxidation of 7-keto steroids, which could not be effectively oxidized using anhydrous methods, and in extending allylic oxidation to enamides and enol ethers.
    Type: Application
    Filed: October 6, 2008
    Publication date: April 9, 2009
    Applicant: UNIVERSITY OF MARYLAND, COLLEGE PARK
    Inventors: Michael P. Doyle, Arthur J. Catino, Hojae Choi, Jason M. Nichols
  • Publication number: 20090054692
    Abstract: Process for preparing cyclohexanone and cyclohexanol, said process comprising (a) neutralising acids and/or carbon dioxide present in an organic solution further comprising cyclohexylhydroperoxide by mixing the organic solution with a first aqueous base solution to form a first mixture comprising a first aqueous phase and a first organic phase, (b) separating first aqueous phase from first organic phase, (c) discharging first aqueous phase, (d) decomposing cyclohexylhydroperoxide present in said first organic phase by mixing said first organic phase with a second aqueous base solution to form a second mixture comprising a second aqueous phase and a second organic phase comprising cyclohexanone and cyclohexanol, (e) separating the second aqueous phase from the second organic phase, (f) feeding at least a portion of said separated second aqueous phase to said neutralising (a), wherein the process further comprises feeding such a portion of the first aqueous phase to the decomposing that the pH of the first aque
    Type: Application
    Filed: January 17, 2006
    Publication date: February 26, 2009
    Inventor: Larry Walker Wyatt
  • Publication number: 20090018367
    Abstract: The present invention relates to a process for preparing cyclohexanone and cyclohexanol, said process comprising (a) neutralising acids and/or carbon dioxide present in an organic solution further comprising cyclohexylhydroperoxide by mixing the organic solution with a first aqueous base solution at a temperature of from 50 to 80° C. to form a first mixture comprising a first aqueous phase with a pH of from 8.5 to 13 and a first organic phase, (b) separating first aqueous phase from the first mixture resulting in a remaining mixture comprising first organic phase, (c) decomposing cyclohexylhydroperoxide present in said remaining mixture by mixing said remaining mixture with a second aqueous base solution at a temperature of from 60 to 110° C. to form a second mixture comprising a second aqueous phase and a second organic phase comprising cyclohexanone and cyclohexanol, (d) separating the second aqueous phase from the second organic phase at a temperature higher than 80° C.
    Type: Application
    Filed: January 17, 2006
    Publication date: January 15, 2009
    Inventor: Larry Walker Wyatt
  • Patent number: 7396961
    Abstract: The present invention relates to a process for decomposing organic hydroperoxides in the presence of a catalyst. It provides a process for decomposing organic hydroperoxides in the presence of a catalyst into a mixture of alcohols and ketones, in which the catalyst comprises at least one ruthenium-based catalytically active metallic element incorporated into a solid support chosen from the group comprising metal oxides and carbon blacks, such as the carbon blacks obtained by the pyrolysis of organic compounds. The process of the invention is especially useful in the decomposition of important chemical intermediates such as cyclohexyl hydroperoxide.
    Type: Grant
    Filed: January 20, 2006
    Date of Patent: July 8, 2008
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Didier Bonnet, Eric Fache, Aline Seigneurin
  • Patent number: 7378557
    Abstract: A method for making isolongifolenone involving reaction (?)-isolongifolene with chromium hexacarbonyl and t-butyl hydroperoxide. Also the use of isolongifolenone to repel arthropods by treating an object or area with an arthropod repelling effective amount of isolongifolenone (and optionally a carrier or carrier material).
    Type: Grant
    Filed: July 13, 2007
    Date of Patent: May 27, 2008
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Aijun Zhang, John Carroll, Shifa Wang, Jerome A. Klun
  • Patent number: 7282611
    Abstract: The present invention provides a process for the preparation of a mixture of alcohols and ketones by the liquid phase oxidation of isoalkanes to alkyl hydroperoxides with simultaneous transfer of oxygen to alkanes (C8-C20) in presence of oxides alkaline earth metals like magnesium, calcium, barium and strontium and oxides of rare earth metals such as lanthanum, cerium, samarium, neodymium and europium, at a temperature ranging between 110°-160° C. and air pressure ranging between 10-1500 psig for a period of 0.5-20 h, cooling the reaction mixture to 5° C., separating the products by conventional methods such as distillation. The catalyst reused for several times without affecting its catalytic performance.
    Type: Grant
    Filed: September 25, 2006
    Date of Patent: October 16, 2007
    Assignee: Council of Scientific and Industrial Research
    Inventors: Deshpande Raj Madhukar, Rane Vilas Hari, Chaudhari Raghunath Vithal
  • Patent number: 7250537
    Abstract: The present invention provides a novel method of hydrogenating a phenol for hydrogenating a phenol industrially advantageously. The present invention relates, in the case of phenol hydrogenation in which carbon dioxide is made to participate in the reaction, to a method of hydrogenating a phenol characterized by using a supported rhodium and/or ruthenium catalyst, whereby the phenol is hydrogenated efficiently at a lower reaction temperature than with prior art; such a method characterized in that carbon dioxide having a temperature of 20 to 250° C. and a pressure of 0.1 to 50 MPa is used as the carbon dioxide; and such a method characterized in that hydrogen under conditions of a temperature of 20 to 250° C. and a pressure of 0.1 to 50 MPa is used. An environmentally friendly phenol hydrogenation process that uses no harmful organic solvents can be realized.
    Type: Grant
    Filed: March 30, 2004
    Date of Patent: July 31, 2007
    Assignee: National Institute of Advanced Industrial Science and Technology
    Inventors: Masayuki Shirai, Chandrashekhar Vasant Rode, Uday Dattopant Joshi, Kazuo Torii, Takafumi Sato
  • Patent number: 7214837
    Abstract: The present invention provides a process for the production of a mixture of alcohols and ketones by the liquid phase oxidation of higher alkanes using a catalyst system consisting of transition group metal such as palladium and support such as alumina, silica, carbon, preferably carbon in the presence of alkyl hydroperoxide as oxygen carrier, under stirring conditions at a temperature range of 10°–120° C. and at atmospheric pressure in a stirred glass reactor for a period of 1–30 h. The present invention produces a mixture of alcohols and ketones with high selectivity (preferably 60–90%) along with other byproducts such as diketones and acids.
    Type: Grant
    Filed: October 29, 2004
    Date of Patent: May 8, 2007
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raj Madhukar Deshpande, Vilas Hari Rane, Raghunath Vitthal Chaudhari
  • Patent number: 7166750
    Abstract: 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone is produced by reacting 1-[(4-chlorophenyl)methyl]-3-methyl-2-oxocyclopentanecarboxylic acid methyl ester or 1-[(4-chlorophenyl)methyl]-3-methyl-2-oxocyclopentanecarboxylic acid ethyl ester with sodium hydride and methyl halide, then hydrolyzing the obtained 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentanecarboxylic acid methyl ester or 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentanecarboxylic acid ethyl ester. The process provides 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone, an important intermediate of an agricultural or horticultural fungicide, e.g., Metconazole.
    Type: Grant
    Filed: August 11, 2000
    Date of Patent: January 23, 2007
    Assignee: Kureha Corporation
    Inventors: Kazuhiko Sunagawa, Hajime Hoshi, Shigeru Mizusawa, Nobuyuki Kusano, Satoru Kumazawa
  • Patent number: 7041854
    Abstract: The present invention relates to a process for the preparation of an xanthophyll, and in particular to a process for the preparation of an xanthophyll through the oxidation of a carotenoid in the presence of hydrogen peroxide and an iodine-containing compound. In particular, the process of the invention applies to the oxidation of beta-carotene to produce canthaxanthin, and to the oxidation of lutein or zeaxanthin to produce astaxanthin.
    Type: Grant
    Filed: April 18, 2002
    Date of Patent: May 9, 2006
    Assignee: Adisseo France S.A.S.
    Inventors: Yannick Quesnel, Richard Flacher
  • Patent number: 6958421
    Abstract: A salt-free process for preparing cyclobutanone, including isomerizing cyclopropylmethanol, preferably in aqueous solution, in the presence of an acidic heterogeneous catalyst to form cyclobutanol and, preferably after extraction and removal of the extractant, dehydrogenating the cyclobutanol over a heterogeneous catalyst.
    Type: Grant
    Filed: June 13, 2003
    Date of Patent: October 25, 2005
    Assignee: Degussa AG
    Inventors: Kerstin Bodmann, Manuela Imig, Günther Köhler, Karl-Heinz Brühl
  • Patent number: 6814867
    Abstract: Disclosed herein is a process for reducing or substantially eliminating chromium in non-volatile residue obtained from a certain processes, and particularly from cyclohexane oxidation processes.
    Type: Grant
    Filed: September 12, 2002
    Date of Patent: November 9, 2004
    Assignee: Inuista North America S.à.r.l.
    Inventors: Ludovic Fodor, Bennett Haines Novak, Jules Charles Joseph Perilloux, Jr., Bhagya Chandra Sutradhar
  • Patent number: 6806390
    Abstract: An improved catalytic process for decomposing alkyl or aromatic hydroperoxides is disclosed which utilizes a caalytic amount of a heterogeneous Au catalyst that has been treated with an organosilicon reagent.
    Type: Grant
    Filed: February 11, 2003
    Date of Patent: October 19, 2004
    Assignee: Inuista North America S.àr.l.
    Inventors: Norman Herron, Stephan Schwarz, Joe Douglas Druliner
  • Patent number: 6806389
    Abstract: The invention relates to the use of an immobilized transition metal carbonyl complex as a catalyst in the Pauson-Khand reaction and to processes using such as catalyst.
    Type: Grant
    Filed: April 19, 2002
    Date of Patent: October 19, 2004
    Assignee: AstraZeneca AB
    Inventors: Alex Christian Comely, Sue Elizabeth Gibson, Neil James Hales
  • Patent number: 6703529
    Abstract: Disclosed herein is a process for the production of a mixture of cyclohexanone and cyclohexanol by oxidation of cyclohexane and decomposition of cyclohexyl hydroperoxide.
    Type: Grant
    Filed: September 12, 2002
    Date of Patent: March 9, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ludovic Fodor, Bhagya Chandra Sutradhar
  • Patent number: 6630075
    Abstract: Fire extinguishing compositions and methods for extinguishing, controlling, or preventing fires are described wherein the extinguishing agent is a fluorinated ketone having up to two hydrogen atoms, alone, or in admixture with a co-extinguishing agent selected from hydrofluorocarbons, hydrochlorofluorocarbons, perfluorocarbons, perfluoropolyethers, hydrofluoroethers, hydrofluoropolyethers, chlorofluorocarbons, bromofluorocarbons, bromochlorofluorocarbons, iodofluorocarbons, hydrobromofluorocarbons, and mixtures thereof.
    Type: Grant
    Filed: October 11, 2002
    Date of Patent: October 7, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: Fred E. Behr, Daniel R. Vitcak, Richard M. Flynn, Michael G. Costello, Michael J. Parent, Zhongxing Zhang
  • Patent number: 6551988
    Abstract: 4,8-cyclododecadienyl ketones having formula (I), in which R has up to 5 carbon atoms, are novel compounds exhibiting woody/amber odor characteristics which find use in perfumes and in perfumed products.
    Type: Grant
    Filed: December 18, 2000
    Date of Patent: April 22, 2003
    Assignee: Quest International B.V.
    Inventor: David Munro
  • Publication number: 20030069450
    Abstract: Dialkyl ketones are prepared by reductive carbonylation of &agr;-olefins by means of carbon monoxide and hydrogen in the presence of a catalyst system comprising
    Type: Application
    Filed: July 18, 2002
    Publication date: April 10, 2003
    Inventors: Michael Slany, Martin Schafer, Michael Roper
  • Patent number: 6500972
    Abstract: A method of oxidizing trimethylphenol (TMP) to trimethylbenzoquinone (TMBQ) by various molecular sieves containing various transition metals. In this method, TMP, a molecular sieve containing a transition metal in its framework, an oxidant and a solvent are mixed together to form a reaction system. The reaction system reacting at a temperature of about room temperature to 150° C. to obtain TMBQ, and the concentration of TMP is about 5-60% wt.
    Type: Grant
    Filed: July 25, 2001
    Date of Patent: December 31, 2002
    Assignee: Chinese Petroleim Corp.
    Inventors: Soofin Cheng, Chia-Lung Tsai, Berryinne Chou, Debasish Das
  • Patent number: 6476274
    Abstract: The invention relates to a process for preparing cyclobutanone by oxidizing cyclobutanol with an alkali metal hypochlorite or alkaline earth metal hypochlorite in the presence of an acid.
    Type: Grant
    Filed: September 6, 2001
    Date of Patent: November 5, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Knops, Bernd Gallenkamp, Lubbertus Mulder, Stefan Antons
  • Patent number: 6469215
    Abstract: A process for the production of an intermediate mixture of &bgr;-isophorone epoxide and its isomer 4-hydroxyisophorone (HIP), comprising reacting &bgr;-isophorone with an organic percarboxylic acid, in the form of its non-aqueous solution, in an inert solvent.
    Type: Grant
    Filed: February 28, 2002
    Date of Patent: October 22, 2002
    Assignee: Degussa AG
    Inventors: Steffen Krill, Klaus Huthmacher, Sylvain Perrin
  • Patent number: 6288281
    Abstract: A process for the carbonylation of saturated hydrocarbons to give an oxygenated saturated hydrocarbon is disclosed and claimed. The process involves using an acidic ionic liquid catalyst to catalyze the carbon monoxide addition to the saturated hydrocarbon at reaction conditions to form an oxygenate. The acidic ionic liquid comprises a Lewis or Bronsted acid in combination with a quaternary nitrogen-containing compound. A specific example is a mixture of aluminum chloride and n-butylpyridinium chloride.
    Type: Grant
    Filed: November 16, 2000
    Date of Patent: September 11, 2001
    Assignee: UOP LLC
    Inventors: Laszlo T. Nemeth, Jeffery C. Bricker, Jennifer S. Holmgren, Lyle E. Monson
  • Patent number: 6284927
    Abstract: An improved process for decomposing alkyl or aromatic hydroperoxides to form a decomposition reaction mixture containing the corresponding alcohol and ketone. The improvement relates to decomposing the hydroperoxide by contacting the hydroperoxide with a catalytic amount of a heterogenous catalyst of Au, Ag, Cu or a sol-gel compound containing particular combinations of Fe, Ni, 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 and used in the presence of an additional metal.
    Type: Grant
    Filed: February 2, 2000
    Date of Patent: September 4, 2001
    Assignee: E. I. du Pont Nemours and Company
    Inventors: Joe Douglas Druliner, Norman Herron, Stephen Paul Jordan, Kostantinos Kourtakis, Samuel Livingston Lane, Leo Ernest Manzer, Bruce Edmund Smart
  • Patent number: 6252119
    Abstract: &Dgr;5-7-oxo-steroids are efficiently prepared from &Dgr;5-steroids using t-BuOOH in the presence of a copper catalyst, such as cuprous and cupric salts and copper metal.
    Type: Grant
    Filed: July 28, 1997
    Date of Patent: June 26, 2001
    Inventors: Jorge António Riberiro Salvador, Maria Luísa Campeão Fernandes Vaz de Sá e Melo, André de Silva Campos Neves
  • Patent number: 6200786
    Abstract: A method of producing nootkatone by laccase catalyzed oxidation of valencene. Valencene and a composition having laccase activity are reacted in the presence of an oxygen source, at a valencene concentration greater than 0.1%, to form valencene hydroperoxide. Optionally, a mediator and/or a solvent at a concentration that maintains laccase activity may also be included. The valencene hydroperoxide is degraded to form nootkatone, and nootkatone is then recovered. The method produces nootkatone in commercially viable yields.
    Type: Grant
    Filed: September 8, 1999
    Date of Patent: March 13, 2001
    Assignee: Givaudan S.A.
    Inventors: Rongmin Huang, Philip A. Christenson, Ivica M. Labuda
  • Patent number: 6191311
    Abstract: An improved process for decomposing alkyl or aromatic hydroperoxides to form a decomposition reaction mixture containing the corresponding alcohol and ketone. The improvement relates to decomposing the hydroperoxide by contacting the hydroperoxide with a catalytic amount of a heterogeneous catalyst of Nb or Hf hydroxide or oxide. The improvement also relates to decomposing a secondary hydroperoxide by contacting the secondary hydroperoxide with a catalytic amount of a heterogeneous catalyst of Zr or Ti hydroxide or oxide. The catalysts may optionally be supported on SiO2, Al2O3, carbon or TiO2.
    Type: Grant
    Filed: March 25, 1999
    Date of Patent: February 20, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Joe Douglas Druliner, Norman Herron
  • Patent number: 6028193
    Abstract: A method for producing aryl alkyl hydroperoxides which comprises selectively oxidizing an aryl alkyl hydrocarbon having the formula: ##STR1## wherein P and Q are hydrogen or an alkyl and may be the same or different from each other; x is an integer of 1-3; and Ar is an aromatic hydrocarbon group having a valence of x, with an oxygen-containing gas in the presence of a transition metal complex which contains, as a ligand, a cyclic polyfunctional amine compound having at least three nitrogen atoms in the ring forming molecular chain or an open chain polyfunctional amine compound having at least three nitrogen atoms in the main chain of the molecule.
    Type: Grant
    Filed: April 15, 1999
    Date of Patent: February 22, 2000
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Terunori Fujita, Shigekazu Matsui, Toshihiro Takai, Hideto Matsuoka, Akifumi Kagayama, Hiroshi Kuroda, Masayasu Ishibashi, Hiroshi Iwasaki, Nobuya Hirokane
  • Patent number: 6008415
    Abstract: Cyclohexane is catalytically oxidized to produce cyclohexanol and cyclohexanone and precursors of these products. The oxidation is carried out in a liquid oxidation reactor at high oxygen concentrations (greater than 30% and preferably greater than 90% oxygen concentration) and at relatively low temperatures (less than 160.degree. C.). The use of the liquid oxidation reactor permits the use of these high oxygen concentrations without forming dangerously high levels of oxygen in the overhead gas phase. The result is an increased yield and selectivity of the desired products.
    Type: Grant
    Filed: July 10, 1998
    Date of Patent: December 28, 1999
    Assignee: ABB Lummus Global Inc.
    Inventors: Marvin I. Greene, Charles Summer, Robert J. Gartside
  • 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: 5922920
    Abstract: A method is provided for preparing organic hydroperoxides by oxidizing aryl alkyl hydrocarbons having a benzylic hydrogen with an oxygen containing gas using as a catalyst an oxo (hydroxo) bridged tetranuclear metal complex having a mixed metal core, one metal of the core being a divalent metal selected from Zn, Cu Fe, Co, Ni, Mn or mixtures thereof and another metal being a trivalent metal selected from In, Fe, Mn, Ga, and Al.
    Type: Grant
    Filed: April 2, 1996
    Date of Patent: July 13, 1999
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jeffrey Evans Bond, Sergiu Mircea Gorun, George William Schriver, Robert Timothy Stibrany, Thomas Henry Vanderspurt, Grayson Hall Via, Baoshan Zhang, Jihad Mohammed Dakka
  • Patent number: 5907065
    Abstract: A method of producing 3,5,5-trimethylcyclohexa-3-ene-1-one (.beta.-isophorone) by isomerization of 3,5,5-trimethylcyclohexa-2-ene-1-one (.alpha.-isophorone) in a liquid phase in the presence of a homogeneous or heterogeneous catalyst in which a mixture with a relatively low concentration of .beta.-isophorone is drawn off from the reaction container and the .beta.-isophorone isolated by vacuum distillation. .beta.-isophorone is an important synthetic structural element for the production of carotinoids, vitamins and pharmaceutical products.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: May 25, 1999
    Assignee: Degussa Aktiengesellschaft
    Inventors: Steffen Krill, Gunes Giray, Frank Hubner, Rainer Hahn, Klaus Huthmacher, Herbert Tanner
  • 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: 5900513
    Abstract: The present invention provide a method for producing 2-cyclohexene-1-ol which comprises using a catalyst containing an inetermetallic compound of palladium and lead and/or bismuth when cyclohexenyl hydroperoxide is subjected to hydrogenolysis to produce 2-cyclohexene-1-ol.If the catalyst of the present invention is employed, it is possible to obtain the desired 2-cyclohexene-1-ol at a high selectivity with a much simpler reaction system than the prior art and, in addition, to inhibit the hydrogenation of coexisting cyclohexene sufficiently.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: May 4, 1999
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hiroshi Ishida, Mitsuji Ono, Masazumi Chono
  • Patent number: 5892123
    Abstract: A method is disclosed for catalytically decomposing cyclododecyl hydroperoxide into cyclododecanone and cyclododecanol using a chromium catalyst.
    Type: Grant
    Filed: February 3, 1998
    Date of Patent: April 6, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Howard Wayne Anderson, James Bernard Sieja
  • Patent number: 5859301
    Abstract: An improved process for preparing alkanones and alkanols by oxidizing an alkane and/or alkene having from 3 to 30 carbon atoms to form an oxidation mixture containing alkylhydroperoxide. A basic, aqueous solution is added to the oxidation mixture so that a separate basic water phase with a pH higher than 8.5 is formed. The alkylhydroperoxide is then decomposed in the presence of a heterogeneous catalyst which contains a metal compound immobilized on a carrier material. The metal of the catalyst is selected from the group consisting of Mn, Fe, Co, Ni, and Cu. The carrier material is stable in the presence of the separate basic water phase.
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: January 12, 1999
    Assignee: DSM N.V.
    Inventors: Ubaldus F. Kragten, Henricus A. C. Baur
  • Patent number: 5780683
    Abstract: Cyclohexane is catalytically oxidized to produce cyclohexanol and cyclohexanone and precursors of these products. The product is then catalytically hydrogenated while the product is still at reaction temperature to produce additional cyclohexanol and cyclohexanone from the precursors. The oxidation is carried out in a liquid oxidation reactor at high oxygen concentrations (greater than 30% and preferably greater than 90% oxygen concentration) and at relatively low temperatures (less than 160.degree. C.). The use of the liquid oxidation reactor permits the use of these high oxygen concentrations without forming dangerously high levels of oxygen in the overhead gas phase. The result is an increased yield and selectivity of the desired products. The hydrogenation is carried out in a reactor using a catalyst of palladium supported on carbon.
    Type: Grant
    Filed: September 11, 1996
    Date of Patent: July 14, 1998
    Assignee: ABB Lummus Global Inc.
    Inventors: Marvin I. Greene, Charles Sumner, Robert J. Gartside
  • Patent number: 5767320
    Abstract: Cyclohexane is oxidized to a mixture of cyclohexanone and cyclohexanol by reaction with oxygen in the presence of a metal complex of phthalocyanine or porphyrin wherein some or all of the hydrogen atoms of the phthalocyanine or porphyrin have been replace by electron withdrawing groups.
    Type: Grant
    Filed: July 26, 1996
    Date of Patent: June 16, 1998
    Assignee: Council of Scientific & Industrial Research
    Inventors: Robert Raja, Paul Ratnasamy
  • Patent number: 5756852
    Abstract: Process for the catalytic oxidation of a saturated hydrocarbon to obtain a ketone which involves carrying out the oxidation simultaneously with the oxidation of H.sub.2 S to form elemental sulfur and the ketone.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: May 26, 1998
    Inventor: Derek H. R. Barton
  • Patent number: 5741939
    Abstract: A process for the copolymerization of carbon monoxide with an olefinically unsaturated compound comprising contacting the monomers in the presence of a liquid diluent with a catalyst composition which is based on(a) a source of a Group VIII metal,(b) a bidentate ligand of the general formulaR.sup.1 R.sup.2 M.sup.1 --R--M.sup.2 R.sup.3 R.sup.4 wherein M.sup.1 and M.sup.2 independently represent a phosphorus, arsenic or antimony atom, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent unsubstituted or substituted hydrocarbyl groups on the understanding that at least one of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 represents a polar substituted aryl group and R represents a bivalent bridging group containing at least two carbon atoms in the bridge, and(c) a boron hydrocarbyl compound,with application of a stirring power transmitted to the polymerization mixture of at least 0.25 kW/m.sup.3.
    Type: Grant
    Filed: March 21, 1996
    Date of Patent: April 21, 1998
    Assignee: Shell Oil Company
    Inventors: Frank Baardman, Arleen Marie Bradford, Jayne Jubb, Pieter Scheerman, Rudolf Jacobus Wijngaarden
  • Patent number: 5723677
    Abstract: The invention comprises a method for the oxidation of alkanes to alcohols and for decomposition of hydroperoxides to alcohols utilizing new compositions of matter, which are metal complexes of porphyrins. Preferred complexes have hydrogen, haloalkyl or haloaryl groups in meso positions, two of the opposed meso atoms or groups being hydrogen or haloaryl, and two of the opposed meso atoms or groups being hydrogen or haloalkyl, but not all four of the meso atoms or groups being hydrogen. Other preferred complexes are ones in which all four of the meso positions are substituted with haloalkyl groups and the beta positions are substituted with halogen atoms. A new method of synthesizing porphyrinogens is also disclosed.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: March 3, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5654487
    Abstract: Catalyst compositions for preparing polyketones comprising (a) a Group VIII metal compound, containing at least one ligand capable of coordinating to the Group VIII metal, and (b) a boron hydrocarbyl compound are disclosed, in particular catalyst compositions wherein the boron hydrocarbyl compound is a Lewis acid of the formula BXYZ where at least one of X, Y and Z is a monovalent hydrocarbyl group. A preferred catalyst composition comprises a palladium complex and B(C.sub.6 F.sub.5).sub.3.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: August 5, 1997
    Assignee: BP Chemicals Limited
    Inventors: Neil Andrew Cooley, Adrian Peter Kirk
  • Patent number: 5616734
    Abstract: The invention relates to the use of compounds of the formula IR.sup.1.sub.a Re.sub.b O.sub.c (I),where a is from 1 to 6, b is from 1 to 4 and c is from 1 to 14 and the sum of a, b and c is in accordance with the valence of from 5 to 7 of the rhenium, with the proviso that c is not greater than 3.multidot.b, and where R.sup.1 is identical or different and is an aliphatic hydrocarbon radical having from 1 to 10 carbon atoms, an aromatic hydrocarbon radical having from 6 to 10 carbon atoms or an arylalkyl radical having from 7 to 9 carbon atoms, with the radicals R.sup.1 being able, if desired, to be identically or differently substituted independently of one another and, in the case of .sigma.-bonded radicals, at least one hydrogen atom still being bonded to the carbon atom in the .alpha. position, as catalysts for the oxidation of electron-rich aromatic compounds and their derivatives and to a process for the oxidation of electron-rich aromatic compounds which comprises oxidizing electron-rich C.sub.6 -C.sub.
    Type: Grant
    Filed: January 25, 1995
    Date of Patent: April 1, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang A. Herrmann, Joao D. G. Correia, Richard Fischer, Waldemar Adam, Jianhua Lin, Chantu R. Saha-Moller, Masao Shimizu
  • Patent number: 5545761
    Abstract: A method of manufacturing 2,6,6-trimethyl-2-cyclohexen-1,4-dione (ketoisophorone) from 3,5,5-trimethyl-2-cyclohexenone (alpha-isophorone). The alpha-isophorone is reacted with hydroperoxide in a solvent, and in the presence of a metal catalyst. The reaction converts the alpha-isophorone directly to ketoisophorone without the intermediate isomerization of alpha-isophorone to beta-isophorone (3,5,5-trimethyl-3-cyclohexenone).
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: August 13, 1996
    Assignee: Aristech Chemical Corporation
    Inventors: Bryan T. Dawson, Joseph Pugach
  • Patent number: 5406002
    Abstract: An organophosphine-treated titanium-containing zeolite is a catalyst for hydrocarbon oxidation.
    Type: Grant
    Filed: February 25, 1994
    Date of Patent: April 11, 1995
    Assignee: Exxon-Chemical Patents Inc.
    Inventors: Luc R. M. Martens, Georges M. K. Mathys
  • 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: 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: 5206441
    Abstract: A process for the conversion of cyclohexyl hydroperoxide to cyclohexanone and cyclohexanol by turbulent high-intensity mixing with aqueous caustic containing a metal salt that accelerates the decomposition of cyclohexyl hydroperoxide.
    Type: Grant
    Filed: April 6, 1992
    Date of Patent: April 27, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ronald A. Reimer