Heavy Metal Patents (Class 568/575)
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Patent number: 7906686Abstract: 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: GrantFiled: April 7, 2008Date of Patent: March 15, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Helge Jaensch, Jihad M. Dakka, Francisco M. Benitez, Ulrich Kortz, Ryan Matthew Richards
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Publication number: 20100185016Abstract: 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: ApplicationFiled: April 7, 2008Publication date: July 22, 2010Inventors: Helge Jaensch, Jihad M. Dakka, Francisco M. Benitez, Ulrich Kortz, Ryan Matthew Richards
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Patent number: 7038090Abstract: 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: GrantFiled: April 1, 2004Date of Patent: May 2, 2006Assignee: UOP LLCInventors: Timothy A. Brandvold, Gregory J. Lewis, Lisa M. King, Lawrence E. Brewer
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Patent number: 6107527Abstract: 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: GrantFiled: March 19, 1997Date of Patent: August 22, 2000Assignee: Rutgers Kureha Solvents GmbHInventors: Zbigniew Stec, Jan Zawadiak, Ulrich Knips, Robert Zellerhoff, Danuta Gilner, Beata Orlinska, Jerzy Polaczek, Witold Tecza, Zofia Machowska
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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: 5646304Abstract: 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: GrantFiled: June 23, 1995Date of Patent: July 8, 1997Assignee: The BOC Group, Inc.Inventors: Divyanshu R. Acharya, Satish S. Tamhankar
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Patent number: 5504256Abstract: 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: March 10, 1995Date of Patent: April 2, 1996Assignee: Exxon Research and Engineering CompanyInventors: Jeffrey E. Bond, Sergiu M. Gorun, George W. Schriver, Robert T. Stibrany, Thomas H. Vanderspurt
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Patent number: 5286902Abstract: A process is disclosed for the synthesis of 2-(6-methoxy-2-naphthyl)propionic acid that utilizes 2,6-diisopropylnaphthalene.Type: GrantFiled: April 15, 1991Date of Patent: February 15, 1994Assignee: Koch Industries, Inc.Inventors: Dustin K. James, Andrew P. Komin, John R. Siegman
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Patent number: 5196598Abstract: 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: GrantFiled: October 18, 1991Date of Patent: March 23, 1993Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki, Kimiko Kaneko
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Patent number: 5183945Abstract: 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: GrantFiled: November 18, 1991Date of Patent: February 2, 1993Assignee: Exxon Research and Engineering CompanyInventors: Robert T. Stibrany, Sergiu M. Gorun
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Patent number: 4801755Abstract: 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: GrantFiled: November 27, 1987Date of Patent: January 31, 1989Assignee: Texaco Inc.Inventors: John R. Sanderson, Edward T. Marquis
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Patent number: 4508923Abstract: 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: GrantFiled: February 22, 1983Date of Patent: April 2, 1985Assignee: Atlantic Richfield CompanyInventors: Paul D. Taylor, Michael T. Mocella
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Patent number: 4503262Abstract: 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: GrantFiled: August 4, 1983Date of Patent: March 5, 1985Assignee: Virginia Chemicals, Inc.Inventors: B. Franklin Gupton, Edwin D. Little
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Patent number: 4341907Abstract: 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: GrantFiled: January 30, 1981Date of Patent: July 27, 1982Assignee: Du Pont Canada Inc.Inventor: Ronald A. Zelonka
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Patent number: 4293720Abstract: 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: GrantFiled: May 2, 1980Date of Patent: October 6, 1981Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Tetsuo Iwaki, Yukio Takahashi, Shuji Moriuchi, Hisamitsu Kaneko
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Patent number: 4288637Abstract: 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: GrantFiled: April 24, 1980Date of Patent: September 8, 1981Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Fujihisa Matsunaga, Yoshiyuki Shinohara, Isamu Okubo, Takayuki Nakamura, Seiichi Tanaka
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Patent number: 4202992Abstract: 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: GrantFiled: March 3, 1978Date of Patent: May 13, 1980Assignee: Phillips Petroleum CompanyInventors: Michael E. Coltrin, Yulin Wu
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Patent number: 4201875Abstract: 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: GrantFiled: August 1, 1978Date of Patent: May 6, 1980Assignee: Phillips Petroleum CompanyInventors: Yulin Wu, Marvin M. Johnson, Gerhard P. Nowack
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Patent number: 4136123Abstract: 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: GrantFiled: July 22, 1974Date of Patent: January 23, 1979Assignee: The Goodyear Tire & Rubber CompanyInventor: David A. Hutchings