Heavy Metal Patents (Class 568/575)
  • Patent number: 7906686
    Abstract: In a process for producing hydroperoxides, an alkylaromatic compound of general formula (I): in which R1 and R2 each independently represents hydrogen or an alkyl group having from 1 to 4 carbon atoms, provided that R1 and R2 may be joined to form a cyclic group having from 4 to 10 carbon atoms, said cyclic group being optionally substituted, and R3 represents hydrogen, one or more alkyl groups having from 1 to 4 carbon atoms or a cyclohexyl group, is contacted with oxygen in the presence of a catalyst comprising a polyoxometalate to produce a hydroperoxide of general formula (II): in which R1, R2 and R3 have the same meaning as in formula (I) and wherein the polyoxometalate comprises a polyoxotungstate substituted with at least one further transition metal.
    Type: Grant
    Filed: April 7, 2008
    Date of Patent: March 15, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Helge Jaensch, Jihad M. Dakka, Francisco M. Benitez, Ulrich Kortz, Ryan Matthew Richards
  • Publication number: 20100185016
    Abstract: In a process for producing hydroperoxides, an alkylaromatic compound of general formula (I): in which R1 and R2 each independently represents hydrogen or an alkyl group having from 1 to 4 carbon atoms, provided that R1 and R2 may be joined to form a cyclic group having from 4 to 10 carbon atoms, said cyclic group being optionally substituted, and R3 represents hydrogen, one or more alkyl groups having from 1 to 4 carbon atoms or a cyclohexyl group, is contacted with oxygen in the presence of a catalyst comprising a polyoxometalate to produce a hydroperoxide of general formula (II): in which R1, R2 and R3 have the same meaning as in formula (I) and wherein the polyoxometalate comprises a polyoxotungstate substituted with at least one further transition metal.
    Type: Application
    Filed: April 7, 2008
    Publication date: July 22, 2010
    Inventors: Helge Jaensch, Jihad M. Dakka, Francisco M. Benitez, Ulrich Kortz, Ryan Matthew Richards
  • Patent number: 7038090
    Abstract: A process and catalyst for preparing organic hydroperoxides by oxidizing hydrocarbon compounds in the presence of an oxygen-containing gas and a catalyst containing a transition metal on a solid support.
    Type: Grant
    Filed: April 1, 2004
    Date of Patent: May 2, 2006
    Assignee: UOP LLC
    Inventors: Timothy A. Brandvold, Gregory J. Lewis, Lisa M. King, Lawrence E. Brewer
  • Patent number: 6107527
    Abstract: The process for the production of hydroxy aromatic substances by means of catalytic oxidation of isoalkyl aromatic substance with oxygen, and decomposition of the hydroperoxide thus formed, is based on the concept that isoalkylaromatic substances are emulsified with an aqueous catalyst solution and brought to a temperature ranging from 50.degree. C. up to the boiling temperature of the emulsion; thereupon the oxygen is allowed to act for 2 to 20 hours and the hydroperoxide formed decomposed, in the presence of an inorganic acid as catalyst, into an hydroxyaromatic substance and a ketone.
    Type: Grant
    Filed: March 19, 1997
    Date of Patent: August 22, 2000
    Assignee: Rutgers Kureha Solvents GmbH
    Inventors: Zbigniew Stec, Jan Zawadiak, Ulrich Knips, Robert Zellerhoff, Danuta Gilner, Beata Orlinska, Jerzy Polaczek, Witold Tecza, Zofia Machowska
  • 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: 5646304
    Abstract: A petrochemical is produced by the vapor phase reaction of a hydrocarbon with air in the presence of a suitable catalyst. The petrochemical is removed from the reactor effluent, and part or all of the remaining petrochemical-free gas stream is passed through a hydrocarbon-selective adsorbent, which adsorbs hydrocarbon from the gas stream, leaving a hydrocarbon-depleted waste gas. Hydrocarbon is purged from the adsorbent with air, and the air-hydrocarbon mixture is recycled to the partial oxidation reactor. The purge air, and preferably both the purge air and the petrochemical-free gas stream are dried by passage through beds of zeolite 3A prior to being introduced into the hydrocarbon-selective adsorbent, and the beds of zeolite 3A are regenerated by passing heated hydrocarbon-depleted waste gas therethrough.
    Type: Grant
    Filed: June 23, 1995
    Date of Patent: July 8, 1997
    Assignee: The BOC Group, Inc.
    Inventors: Divyanshu R. Acharya, Satish S. Tamhankar
  • Patent number: 5504256
    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: March 10, 1995
    Date of Patent: April 2, 1996
    Assignee: Exxon Research and Engineering Company
    Inventors: Jeffrey E. Bond, Sergiu M. Gorun, George W. Schriver, Robert T. Stibrany, Thomas H. Vanderspurt
  • Patent number: 5286902
    Abstract: A process is disclosed for the synthesis of 2-(6-methoxy-2-naphthyl)propionic acid that utilizes 2,6-diisopropylnaphthalene.
    Type: Grant
    Filed: April 15, 1991
    Date of Patent: February 15, 1994
    Assignee: Koch Industries, Inc.
    Inventors: Dustin K. James, Andrew P. Komin, John R. Siegman
  • Patent number: 5196598
    Abstract: A process for producing a polyhydroperoxy aromatic compound by oxidation of an aromatic hydrocarbon, e.g., 4,4'-diisopropylbiphenyl and 4,4'-diisopropylnaphthalene, with molecular oxygen is disclosed, in which the oxidation is carried out in the presence of a metal ion selected from cobalt, nickel, zinc and lead ions. Even in using a reaction apparatus made of an iron-containing metal generally employed in industry, a high conversion of secondary alkyl groups can be reached, and the desired polyhydroperoxy aromatic compound can be obtained in a high yield.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: March 23, 1993
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki, Kimiko Kaneko
  • Patent number: 5183945
    Abstract: This invention relates to a process for preparing organic hydroperoxides by selectively oxidizing aryl alkyl hydrocarbons to their corresponding organic hydroperoxides using a catalyst certain tetranuclear manganese complexes. The process is carried out without appreciable decomposition by the catalyst of the resulting organic hydroperoxides, and without oxidation by the catalyst of other hydrocarbons present in the starting mixture.The process of the present invention is useful for producing organic hydroperoxides, which themselves are useful as starting materials for a number of commercial reactions, for example, phenol and acetone production.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: February 2, 1993
    Assignee: Exxon Research and Engineering Company
    Inventors: Robert T. Stibrany, Sergiu M. Gorun
  • Patent number: 4801755
    Abstract: The oxidation of isobutane in the presence of a novel, soluble propylene glycol/vanadium catalyst is disclosed. Tertiary-butyl alcohol, tertiary-butyl hydroperoxide, and acetone are produced. A significant increase in isobutane conversion is obtained without a large decrease in selectivity to tertiary-butyl alcohol and tertiary-butyl hydroperoxide using a small amount of catalyst. Tertiary-butyl alcohol is useful as a gasoline additive and tertiary-butyl hydroperoxide is used for the production of propylene oxide. Acetone has a variety of uses as well.
    Type: Grant
    Filed: November 27, 1987
    Date of Patent: January 31, 1989
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Edward T. Marquis
  • Patent number: 4508923
    Abstract: There is disclosed an improved process for oxidizing a hydrocarbon to produce a reaction mixture containing the corresponding organic hydroperoxide of said hydrocarbon and decomposing said hydroperoxide to provide a mixture containing reaction products of said decomposition reaction, including alcohol and/or ketone products, comprising effecting said oxidation and/or decomposition in the presence of a catalytic quantity of a catalyst system comprised of ruthenium and chromium.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: April 2, 1985
    Assignee: Atlantic Richfield Company
    Inventors: Paul D. Taylor, Michael T. Mocella
  • Patent number: 4503262
    Abstract: A process is disclosed for the preparation of 2,6-dihydroisopropylnaphthalene, dihydroperoxide involving the oxidation of 2,6-diisopropylnaphthalene in the presence of a catalyst wherein the improvement comprises carrying out said oxidation in the presence of a C.sub.5 -C.sub.14 aliphatic hydrocarbon solvent.
    Type: Grant
    Filed: August 4, 1983
    Date of Patent: March 5, 1985
    Assignee: Virginia Chemicals, Inc.
    Inventors: B. Franklin Gupton, Edwin D. Little
  • Patent number: 4341907
    Abstract: A process is disclosed for the catalytic oxidation of a cycloparaffin, e.g., cyclohexane, to partial oxidation products thereof, especially for the production of mixtures of cycloalkanols and cycloalkanones. In the process, molecular oxygen, usually in the presence of an inert gas, is introduced into the cycloparaffin at elevated pressure and a temperature of 130.degree.-180.degree. C., in the presence of an oxidation catalyst comprising a heavy metal compound along with an N-heterocyclic compound. The heavy metal of the heavy metal compound may be cobalt, vanadium, manganese, copper, iron or nickel. The heavy metal compound may have ligands of alkanoate, dialkylphosphate, dicycloalkylphosphate or alkylcycloalkylphosphate. The N-heterocyclic compound may be dipyridyl, pyrimidine, pyrazine, pyridine and pyridine substituted with --CN, --R, and/or --OR where R is alkyl. A preferred catalyst is cobalt bis[di(2-ethylhexyl)phosphate] in combination with pyridine.
    Type: Grant
    Filed: January 30, 1981
    Date of Patent: July 27, 1982
    Assignee: Du Pont Canada Inc.
    Inventor: Ronald A. Zelonka
  • Patent number: 4293720
    Abstract: Disclosed is a process for the preparation of hydroperoxides comprising liquid-phase oxidizing an aromatic compound having a secondary alkyl group with molecular oxygen in the presence of a basic aqueous solution and a copper compound catalyst, wherein an aqueous solution containing (A) cupric carbonate and (B) an alkali metal carbonate and/or an alkali metal bicarbonate is prepared outside the oxidation system and this aqueous solution is supplied to the oxidation system.According to the process, even under basic conditions, inactivation of the catalyst owing to precipitation is prevented, and the intended aromatic hydroperoxide can be obtained at a high oxidation speed.
    Type: Grant
    Filed: May 2, 1980
    Date of Patent: October 6, 1981
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Tetsuo Iwaki, Yukio Takahashi, Shuji Moriuchi, Hisamitsu Kaneko
  • Patent number: 4288637
    Abstract: Disclosed is a process for the preparation of aromatic hydroperoxides comprising contacting two liquid phases comprising an oily phase containing an aromatic compound having a secondary alkyl group and a basic aqueous phase under agitation with a molecular oxygen-containing gas in the presence of a copper compound catalyst such as an inorganic salt or organic acid salt of copper, thereby to oxidize the aromatic compound to a corresponding aromatic hydroperoxide, wherein the liquid phase catalytic oxidation is carried out while maintaining the catalyst concentration in the liquid phases at 0.005 to 10 ppm as the copper atom and the pH value of the basic aqueous phase at 7.6 to 10. According to this process, by adoption of the above-mentioned specific catalyst concentration and pH value in combination, the rate of oxidation of the aromatic compound is increased and the selectivity to the hydroperoxide is improved.
    Type: Grant
    Filed: April 24, 1980
    Date of Patent: September 8, 1981
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Fujihisa Matsunaga, Yoshiyuki Shinohara, Isamu Okubo, Takayuki Nakamura, Seiichi Tanaka
  • Patent number: 4202992
    Abstract: Organic hydroperoxides are prepared by reacting an organic compound with oxygen in the absence of light and in the presence of a suitable nickel or copper porphine complex.
    Type: Grant
    Filed: March 3, 1978
    Date of Patent: May 13, 1980
    Assignee: Phillips Petroleum Company
    Inventors: Michael E. Coltrin, Yulin Wu
  • Patent number: 4201875
    Abstract: Organic hydroperoxides are prepared by reacting an organic compound with oxygen in the presence of a novel catalyst comprising metallic silver supported upon an inorganic support selected from the oxides and carbonates of metals of Groups IIa, IIb, IIIb, and IVb.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: May 6, 1980
    Assignee: Phillips Petroleum Company
    Inventors: Yulin Wu, Marvin M. Johnson, Gerhard P. Nowack
  • Patent number: 4136123
    Abstract: Metallo phthalocyanines which have been rendered water soluble by substituting an alkali metal or alkaline earth metal sulfate or carboxylate salt onto the phthalocyanine structure have been found to be effective catalysts for the oxidation of aromatic compounds having benzylic carbon atoms to form the corresponding hydroperoxides.
    Type: Grant
    Filed: July 22, 1974
    Date of Patent: January 23, 1979
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: David A. Hutchings