Carbon Monoxide Or Peroxy Containing Reactant Patents (Class 568/342)
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Publication number: 20100137645Abstract: 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: ApplicationFiled: December 16, 2005Publication date: June 3, 2010Inventor: Imre Toth
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Patent number: 7642384Abstract: 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: GrantFiled: January 17, 2006Date of Patent: January 5, 2010Assignee: DSM IP Assets B.V.Inventor: Larry Walker Wyatt
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Patent number: 7619122Abstract: 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 aqueType: GrantFiled: January 17, 2006Date of Patent: November 17, 2009Assignee: DSM IP Assets B.V.Inventor: Larry Walker Wyatt
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Publication number: 20090093638Abstract: 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: ApplicationFiled: October 6, 2008Publication date: April 9, 2009Applicant: UNIVERSITY OF MARYLAND, COLLEGE PARKInventors: Michael P. Doyle, Arthur J. Catino, Hojae Choi, Jason M. Nichols
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Publication number: 20090054692Abstract: 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 aqueType: ApplicationFiled: January 17, 2006Publication date: February 26, 2009Inventor: Larry Walker Wyatt
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Publication number: 20090018367Abstract: 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: ApplicationFiled: January 17, 2006Publication date: January 15, 2009Inventor: Larry Walker Wyatt
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Patent number: 7396961Abstract: 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: GrantFiled: January 20, 2006Date of Patent: July 8, 2008Assignee: Rhodia Polyamide IntermediatesInventors: Didier Bonnet, Eric Fache, Aline Seigneurin
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Patent number: 7378557Abstract: 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: GrantFiled: July 13, 2007Date of Patent: May 27, 2008Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Aijun Zhang, John Carroll, Shifa Wang, Jerome A. Klun
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Patent number: 7282611Abstract: 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: GrantFiled: September 25, 2006Date of Patent: October 16, 2007Assignee: Council of Scientific and Industrial ResearchInventors: Deshpande Raj Madhukar, Rane Vilas Hari, Chaudhari Raghunath Vithal
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Patent number: 7250537Abstract: 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: GrantFiled: March 30, 2004Date of Patent: July 31, 2007Assignee: National Institute of Advanced Industrial Science and TechnologyInventors: Masayuki Shirai, Chandrashekhar Vasant Rode, Uday Dattopant Joshi, Kazuo Torii, Takafumi Sato
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Patent number: 7214837Abstract: 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: GrantFiled: October 29, 2004Date of Patent: May 8, 2007Assignee: Council of Scientific and Industrial ResearchInventors: Raj Madhukar Deshpande, Vilas Hari Rane, Raghunath Vitthal Chaudhari
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Patent number: 7166750Abstract: 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: GrantFiled: August 11, 2000Date of Patent: January 23, 2007Assignee: Kureha CorporationInventors: Kazuhiko Sunagawa, Hajime Hoshi, Shigeru Mizusawa, Nobuyuki Kusano, Satoru Kumazawa
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Patent number: 7041854Abstract: 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: GrantFiled: April 18, 2002Date of Patent: May 9, 2006Assignee: Adisseo France S.A.S.Inventors: Yannick Quesnel, Richard Flacher
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Patent number: 6958421Abstract: 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: GrantFiled: June 13, 2003Date of Patent: October 25, 2005Assignee: Degussa AGInventors: Kerstin Bodmann, Manuela Imig, Günther Köhler, Karl-Heinz Brühl
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Patent number: 6814867Abstract: 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: GrantFiled: September 12, 2002Date of Patent: November 9, 2004Assignee: Inuista North America S.à.r.l.Inventors: Ludovic Fodor, Bennett Haines Novak, Jules Charles Joseph Perilloux, Jr., Bhagya Chandra Sutradhar
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Patent number: 6806390Abstract: 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: GrantFiled: February 11, 2003Date of Patent: October 19, 2004Assignee: Inuista North America S.àr.l.Inventors: Norman Herron, Stephan Schwarz, Joe Douglas Druliner
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Patent number: 6806389Abstract: 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: GrantFiled: April 19, 2002Date of Patent: October 19, 2004Assignee: AstraZeneca ABInventors: Alex Christian Comely, Sue Elizabeth Gibson, Neil James Hales
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Patent number: 6703529Abstract: 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: GrantFiled: September 12, 2002Date of Patent: March 9, 2004Assignee: E. I. du Pont de Nemours and CompanyInventors: Ludovic Fodor, Bhagya Chandra Sutradhar
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Patent number: 6630075Abstract: 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: GrantFiled: October 11, 2002Date of Patent: October 7, 2003Assignee: 3M Innovative Properties CompanyInventors: Fred E. Behr, Daniel R. Vitcak, Richard M. Flynn, Michael G. Costello, Michael J. Parent, Zhongxing Zhang
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Patent number: 6551988Abstract: 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: GrantFiled: December 18, 2000Date of Patent: April 22, 2003Assignee: Quest International B.V.Inventor: David Munro
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Publication number: 20030069450Abstract: Dialkyl ketones are prepared by reductive carbonylation of &agr;-olefins by means of carbon monoxide and hydrogen in the presence of a catalyst system comprisingType: ApplicationFiled: July 18, 2002Publication date: April 10, 2003Inventors: Michael Slany, Martin Schafer, Michael Roper
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Patent number: 6500972Abstract: 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: GrantFiled: July 25, 2001Date of Patent: December 31, 2002Assignee: Chinese Petroleim Corp.Inventors: Soofin Cheng, Chia-Lung Tsai, Berryinne Chou, Debasish Das
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Patent number: 6476274Abstract: 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: GrantFiled: September 6, 2001Date of Patent: November 5, 2002Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Knops, Bernd Gallenkamp, Lubbertus Mulder, Stefan Antons
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Patent number: 6469215Abstract: 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: GrantFiled: February 28, 2002Date of Patent: October 22, 2002Assignee: Degussa AGInventors: Steffen Krill, Klaus Huthmacher, Sylvain Perrin
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Patent number: 6288281Abstract: 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: GrantFiled: November 16, 2000Date of Patent: September 11, 2001Assignee: UOP LLCInventors: Laszlo T. Nemeth, Jeffery C. Bricker, Jennifer S. Holmgren, Lyle E. Monson
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Patent number: 6284927Abstract: 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: GrantFiled: February 2, 2000Date of Patent: September 4, 2001Assignee: E. I. du Pont Nemours and CompanyInventors: Joe Douglas Druliner, Norman Herron, Stephen Paul Jordan, Kostantinos Kourtakis, Samuel Livingston Lane, Leo Ernest Manzer, Bruce Edmund Smart
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Patent number: 6252119Abstract: &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: GrantFiled: July 28, 1997Date of Patent: June 26, 2001Inventors: Jorge António Riberiro Salvador, Maria Luísa Campeão Fernandes Vaz de Sá e Melo, André de Silva Campos Neves
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Patent number: 6200786Abstract: 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: GrantFiled: September 8, 1999Date of Patent: March 13, 2001Assignee: Givaudan S.A.Inventors: Rongmin Huang, Philip A. Christenson, Ivica M. Labuda
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Patent number: 6191311Abstract: 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: GrantFiled: March 25, 1999Date of Patent: February 20, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Joe Douglas Druliner, Norman Herron
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Patent number: 6028193Abstract: 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: GrantFiled: April 15, 1999Date of Patent: February 22, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Terunori Fujita, Shigekazu Matsui, Toshihiro Takai, Hideto Matsuoka, Akifumi Kagayama, Hiroshi Kuroda, Masayasu Ishibashi, Hiroshi Iwasaki, Nobuya Hirokane
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Patent number: 6008415Abstract: 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: GrantFiled: July 10, 1998Date of Patent: December 28, 1999Assignee: ABB Lummus Global Inc.Inventors: Marvin I. Greene, Charles Summer, Robert J. Gartside
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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: 5922920Abstract: 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: GrantFiled: April 2, 1996Date of Patent: July 13, 1999Assignee: 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
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Patent number: 5907065Abstract: 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: GrantFiled: September 26, 1997Date of Patent: May 25, 1999Assignee: Degussa AktiengesellschaftInventors: Steffen Krill, Gunes Giray, Frank Hubner, Rainer Hahn, Klaus Huthmacher, Herbert Tanner
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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: 5900513Abstract: 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: GrantFiled: February 6, 1998Date of Patent: May 4, 1999Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hiroshi Ishida, Mitsuji Ono, Masazumi Chono
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Patent number: 5892123Abstract: A method is disclosed for catalytically decomposing cyclododecyl hydroperoxide into cyclododecanone and cyclododecanol using a chromium catalyst.Type: GrantFiled: February 3, 1998Date of Patent: April 6, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Howard Wayne Anderson, James Bernard Sieja
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Patent number: 5859301Abstract: 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: GrantFiled: December 23, 1994Date of Patent: January 12, 1999Assignee: DSM N.V.Inventors: Ubaldus F. Kragten, Henricus A. C. Baur
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Patent number: 5780683Abstract: 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: GrantFiled: September 11, 1996Date of Patent: July 14, 1998Assignee: ABB Lummus Global Inc.Inventors: Marvin I. Greene, Charles Sumner, Robert J. Gartside
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Patent number: 5767320Abstract: 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: GrantFiled: July 26, 1996Date of Patent: June 16, 1998Assignee: Council of Scientific & Industrial ResearchInventors: Robert Raja, Paul Ratnasamy
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Patent number: 5756852Abstract: 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: GrantFiled: October 15, 1996Date of Patent: May 26, 1998Inventor: Derek H. R. Barton
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Patent number: 5741939Abstract: 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: GrantFiled: March 21, 1996Date of Patent: April 21, 1998Assignee: Shell Oil CompanyInventors: Frank Baardman, Arleen Marie Bradford, Jayne Jubb, Pieter Scheerman, Rudolf Jacobus Wijngaarden
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Patent number: 5723677Abstract: 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: GrantFiled: June 27, 1996Date of Patent: March 3, 1998Assignee: Sun Company, Inc. (R&M)Inventors: Tilak Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
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Patent number: 5654487Abstract: 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: GrantFiled: June 6, 1995Date of Patent: August 5, 1997Assignee: BP Chemicals LimitedInventors: Neil Andrew Cooley, Adrian Peter Kirk
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Patent number: 5616734Abstract: 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: GrantFiled: January 25, 1995Date of Patent: April 1, 1997Assignee: Hoechst AktiengesellschaftInventors: Wolfgang A. Herrmann, Joao D. G. Correia, Richard Fischer, Waldemar Adam, Jianhua Lin, Chantu R. Saha-Moller, Masao Shimizu
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Patent number: 5545761Abstract: 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: GrantFiled: November 14, 1994Date of Patent: August 13, 1996Assignee: Aristech Chemical CorporationInventors: Bryan T. Dawson, Joseph Pugach
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Patent number: 5406002Abstract: An organophosphine-treated titanium-containing zeolite is a catalyst for hydrocarbon oxidation.Type: GrantFiled: February 25, 1994Date of Patent: April 11, 1995Assignee: Exxon-Chemical Patents Inc.Inventors: Luc R. M. Martens, Georges M. K. Mathys
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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: 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: 5206441Abstract: 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: GrantFiled: April 6, 1992Date of Patent: April 27, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ronald A. Reimer