Initiator, Accelerator, Or Catalyst Utilized Patents (Class 568/573)
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Patent number: 8921610Abstract: A process for oxidizing a composition comprising contacting an alkylbenzene of the general formula (I): where R1 and R2 each independently represents hydrogen or an alkyl group having from 1 to 4 carbon atoms, wherein R1 and R2 may be joined to form a cyclic group having from 4 to 10 carbon atoms, the 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; and (ii) about 0.05 wt % to about 5 wt % of phenol, with oxygen in the presence of a catalyst containing a cyclic imide having the general formula (II): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group under conditions effective to convert at least a portion of the alkylbenzene to a hydroperoxide.Type: GrantFiled: August 16, 2011Date of Patent: December 30, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Edmund J. Mozeleski, Charles Morris Smith, Christopher L. Becker, Stephen Zushma
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Patent number: 8921609Abstract: In a process for oxidizing a hydrocarbon, the hydrocarbon is contacted with oxygen in the presence of an N-substituted cyclic imide and under conditions to oxidize the hydrocarbon to produce an oxidized hydrocarbon product and at least one decomposition product of the N-substituted cyclic imide. At least a portion of the at least one decomposition product is contacted with hydroxylamine or a salt thereof under conditions to convert the at least one decomposition product back to said imide.Type: GrantFiled: September 30, 2010Date of Patent: December 30, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Stephen Zushma, Nicolas P. Coute, Francisco M. Benitez, Edmund J. Mozeleski
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Patent number: 8791306Abstract: In a process for oxidizing an alkylaromatic compound to the corresponding hydroperoxide, a feed comprising an alkylaromatic compound is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide. The contacting is conducted at a temperature of about 90° C. to about 150° C., with the cyclic imide being present in an amount between about 0.05 wt % and about 5 wt % of the alkylaromatic compound in the feed and the catalyst being substantially free of alkali metal compounds. The contacting oxidizes at least part of the alkylaromatic compound in said feed to the corresponding hydroperoxide.Type: GrantFiled: May 28, 2013Date of Patent: July 29, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Stephen Zushma, Jon E. R. Stanat
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Patent number: 8674145Abstract: The purpose of the present invention is to provide an advantageous method for accelerating the cumene oxidation reaction without the drawbacks of the above-described previously known approaches by utilizing one or more airlift-type tray installed in one or more conventional commercial reactors utilized during the cumene oxidation process. Such a method is of great use in process configurations where it is desirable to achieve a controlled acceleration of the cumene oxidation process without decreasing process selectivity.Type: GrantFiled: June 30, 2008Date of Patent: March 18, 2014Assignee: Illa International, L.L.C.Inventors: Vladimir Zakoshansky, Andrey Budarev
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Publication number: 20130203984Abstract: In a process for oxidizing a hydrocarbon to a product comprising at least one of the corresponding hydroperoxide, alcohol, ketone, carboxylic acid and dicarboxylic acid, the hydrocarbon is contacted with an oxygen-containing compound in at least one oxidation zone in the presence of a catalyst comprising a cyclic imide having an imide group of formula (I): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group and wherein the oxygen-containing compound supplied to said at least one oxidation zone has a water content of less than or equal to 0.6% by weight of the oxygen-containing compound.Type: ApplicationFiled: August 16, 2011Publication date: August 8, 2013Inventors: Christopher L. Becker, Jihad M. Dakka, Franisco M. Benitez, Edmund J. Mozeleski
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Patent number: 8461397Abstract: In a process for oxidizing a hydrocarbon to the corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, a reaction medium comprising a hydrocarbon is contacted with an oxygen-containing gas in a reaction zone and in the presence of a catalyst comprising a cyclic imide. During the oxidation process, a portion of the reaction medium is continuously or intermittently removed from the reaction zone, is stripped of water and organic acid impurities and then returned to the reaction zone.Type: GrantFiled: August 17, 2009Date of Patent: June 11, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: James R. Lattner, Mark Hagemeister, Jon E. R. Stanat, John S. Buchanan, Jihad M. Dakka, Stephen Zushma
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Patent number: 8461398Abstract: In a process for oxidizing an alkylaromatic compound to the corresponding hydroperoxide, a feed comprising an alkylaromatic compound is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide. The contacting is conducted at a temperature of about 90° C. to about 150° C., with the cyclic imide being present in an amount between about 0.05 wt % and about 5 wt % of the alkylaromatic compound in the feed and the catalyst being substantially free of alkali metal compounds. The contacting oxidizes at least part of the alkylaromatic compound in said feed to the corresponding hydroperoxide.Type: GrantFiled: September 17, 2009Date of Patent: June 11, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Stephen Zushma, Jon E. R. Stanat
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Patent number: 8445730Abstract: In a process for producing phenol or a substituted phenol, an alkylaromatic hydroperoxide having a general formula (I): in which R1 and R2 each independently represents 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 a catalyst comprising an oxide of at least one metal from Groups 3 to 5 and Groups 7 to 14 of the Periodic Table of the Elements and an oxide of at least one metal from Group 6 of the Periodic Table of the Elements.Type: GrantFiled: July 14, 2009Date of Patent: May 21, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Kun Wang, Edmund J. Mozeleski, Stephen Zushma
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Patent number: 8445729Abstract: Process for the preparation of hydroperoxides of alkylbenzenes characterized by the fact that the alkylbenzene reacts with oxygen in the presence of a catalytic system which includes an N-hydroxyimide or an N-hydroxysulfamide and a polar solvent.Type: GrantFiled: March 13, 2009Date of Patent: May 21, 2013Assignee: Polimeri Europa S.p.A.Inventors: Francesco Minisci, Carlo Punta, Francesco Recupero, Cristian Gambarotti, Raffaele Spaccini, Angelo Clerici, Alberto Clerici
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Publication number: 20110251436Abstract: Process for the preparation of hydroperoxides of alkylbenzenes characterized by the fact that the alkylbenzene reacts with oxygen in the presence of a catalytic system which includes an N-hydroxyimide or an N-hydroxysulfamide and a polar solvent.Type: ApplicationFiled: March 13, 2009Publication date: October 13, 2011Applicant: POLIMERI EUROPA S.P.A.Inventors: Francesco Minisci, Carlo Punta, Francesco Recupero, Christian Gambarotti, Raffaele Spaccini, Ombretta Porta, Angelo Clerici, Alberto Clerici
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Publication number: 20110172466Abstract: In a process for oxidizing a hydrocarbon to the corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, a reaction medium comprising a hydrocarbon is contacted with an oxygen-containing gas in a reaction zone and in the presence of a catalyst comprising a cyclic imide. During the oxidation process, a portion of the reaction medium is continuously or intermittently removed from the reaction zone, is stripped of water and organic acid impurities and then returned to the reaction zone.Type: ApplicationFiled: August 17, 2009Publication date: July 14, 2011Applicant: EXXONMOBIL CHEMICAL PATENTS INC.Inventors: James R. Lattner, Mark Hagemeister, Jon E.R. Stanat, John S. Buchanan, Jihad M. Dakka, Stephen Zushma
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Publication number: 20110092742Abstract: In a process for producing alkylbenzene hydroperoxides, a feed comprising (i) sec-butylbenzene, (ii) cumene in an amount greater than 10 wt % of the total feed and (iii) at least one of iso-butylbenzene and tert-butylbenzene in an amount up to 20 wt % of the total feed is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide of the general formula (I): wherein each of R1 and R2 is independently selected from hydrocarbyl and substituted hydrocarbyl radicals having 1 to 20 carbon atoms, or from the groups SO3H, NH2, OH, and NO2 or from the atoms H, F, Cl, Br, and I, provided that R1 and R2 can be linked to one another via a covalent bond; each of Q1 and Q2 is independently selected from C, CH, N and CR3; each of X and Z is independently selected from C, S, CH2, N, P and elements of Group 4 of the Periodic Table; Y is O or OH; k is 0, 1, or 2; l is 0, 1, or 2; m is 1 to 3; and R3 can be any of the entities listed for R1.Type: ApplicationFiled: July 14, 2009Publication date: April 21, 2011Inventors: Jihad M. Dakka, Stephen Zushma
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Patent number: 7763755Abstract: To provide a method for producing dialkylhydroperoxybenzene by liquid-phase oxidation of dialkylbenzene, wherein the method comprises the following steps, Oxidation step: a step of obtaining a oxidation reaction liquid having pH of 9 to 12, which contains dialkylhydroperoxybenzene, unreacted dialkylbenzene, and by-produced hydroperoxybenzenes by subjecting an oxidation raw material solution containing dialkylbenzene to oxidation reaction, Aqueous solution extracting step: a step of extracting the oxidation reaction liquid with an alkaline aqueous solution to obtain a water layer mainly containing dialkylhydroperoxybenzene and by-produced hydroperoxybenzenes, and an oil layer mainly containing dialkylbenzene, and Recycle step: a step of recycling and feeding at least a part of the oil layer obtained in the aqueous solution extracting step to the oxidation step, wherein the oxidation step comprises two or more reaction sections of a first section and subsequent sections arranged in series, and the temperatureType: GrantFiled: February 14, 2007Date of Patent: July 27, 2010Assignee: Sumitomo Chemical Company, LimitedInventor: Mitsuru Onuma
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Patent number: 7476769Abstract: Process for the preparation of a hydroperoxide functionalized olefinic compound in an oxidation reactor containing a particulate catalyst bed comprising a light induced photosensitized catalyst component supported on a particulate substrate material forming a permeable catalyst bed. The photoenergized catalyst component is a photoreductant material which is effective for the conversion of triplet oxygen to singlet oxygen under illumination with ultraviolet or visible light. An oxygen containing feed stream containing triplet oxygen is supplied to the catalyst bed. The catalyst bed is irradiated at an intensity to convert triplet oxygen to singlet oxygen to produce a singlet oxygen enriched gas stream.Type: GrantFiled: November 9, 2007Date of Patent: January 13, 2009Assignee: Fina Technology, Inc.Inventors: Olga Khabasheshku, Jason Clark, Steve Harden, Steven Gray, Vance Stevens, Carlos Corleto
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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: 6720462Abstract: The invention relates to a process for preparing phenol derivatives by catalytic oxidation of an aromatic hydrocarbon to the hydroperoxide and subsequent cleavage of the hydroperoxide to give the phenol derivative and a ketone, wherein a compound of the formula I where R1, R2=H, aliphatic or aromatic alkoxy radical, carboxyl radical, alkoxycarbonyl radical or hydrocarbon radical, in each case having from 1 to 20 carbon atoms, SO3H, NH2, OH, F, Cl, Br, I and/or NO2, where R1 and R2 are identical or different radicals or R1 and R2 may be joined to one another via a covalent bond, and X, Z=C, S, CH2 Y=O, OH k=0, 1, 2 l=0, 1, 2 m=1-3; is used as oxidation catalyst in the presence of a free-radical initiator, where the molar ratio of the catalyst to the aromatic hydrocarbon is less than 10 mol %.Type: GrantFiled: September 26, 2002Date of Patent: April 13, 2004Assignee: Degussa AGInventors: Adolf Kuhnle, Mark Duda, Uwe Tanger, Roger Arthur Sheldon, Sasidharan Manickam, Isabella W. C. E. Arends
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Patent number: 6476276Abstract: A process for preparing hydroperoxides which comprises oxidizing hydrocarbon by a gas containing oxygen in the presence of a specific compound and converting them selectively to corresponding hydroperoxides. The specific compound is the compound that can capture radicals. The preferable example may be a compound selected from radicals of oxygen, nitrogen, phosphorus, sulfur, carbon or silicon or a compound that forms radicals of these in the reaction system. The present invention can be applied to oxidation of hydrocarbons including arylalkylhydrocarbons such as cumene, m-diisopropylbenzene, p-diisopropylbenzene, 1,3,5-triisopropylbenzene, isopropylnaphthalene, diisopropylnaphthalene, isopropylbiphenyl, diisopropylbiphenyl, etc.Type: GrantFiled: July 19, 2001Date of Patent: November 5, 2002Assignee: Mitsui Chemicals, Inc.Inventors: Shigekazu Matsui, Hiroshi Kuroda, Nobuya Hirokane, Haruyuki Makio, Toshihiro Takai, Koji Kato, Terunori Fujita, Makoto Kamimura
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Patent number: 6426057Abstract: A continuous process for oxidation, in which the substance to be oxidized and the oxidizing gas flow countercurrently and the oxidizing gas is mixed with a split stream containing preoxidized substance before it enters the reactor. A Venturi nozzle is particularly suitable as the mixing organ in the reactor.Type: GrantFiled: November 15, 2001Date of Patent: July 30, 2002Assignee: Degussa AGInventor: Bernhard Maurer
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Patent number: 6291718Abstract: A process for preparing hydroperoxides which comprises oxidizing hydrocarbon by a gas containing oxygen in the presence of a specific compound and converting them selectively to corresponding hydroperoxides. The specific compound is the compound that can capture radicals. The preferable example may be a compound selected from radicals of oxygen, nitrogen, phosphorus, sulfur, carbon or silicon or a compound that forms radicals of these in the reaction system. The present invention can be applied to oxidation of hydrocarbons including arylalkylhydrocarbons such as cumene, m-diisopropylbenzene, p-diisopropylbenzene, 1,3,5-triisopropylbenzene, isopropylnaphthalene, diisopropylnaphthalene, isopropylbiphenyl, diisopropylbiphenyl, etc.Type: GrantFiled: March 2, 1999Date of Patent: September 18, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Shigekazu Matsui, Hiroshi Kuroda, Nobuya Hirokane, Haruyuki Makio, Toshihiro Takai, Koji Kato, Terunori Fujita, Makoto Kamimura
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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: 5908962Abstract: Greater efficiency in a water-alkaline emulsion cumene oxidation process using a cascade of reactors is obtained by splitting the reactor cascade into 2 stages with the first stage utilizing NH.sub.4 NaCO.sub.3 as the active carbonate in the stage containing less than 18% by weight cumene hydroperoxide and using Na.sub.2 CO.sub.3 as the active carbonate in the stage containing more than 18% by weight cumene hydroperoxide. By directly injecting ammonia into a recycle stream organic acids are efficiently neutralized. A counter current water wash of the second stage also increases process efficiency by scrubbing out unwanted impurities. Control of pH in the process improves efficiency and reduces impurity levels.Type: GrantFiled: February 9, 1998Date of Patent: June 1, 1999Assignee: General Electric Company and Illa InternationalInventors: Vladimir Mikhailovich Zakoshansky, Andrei Konstantinovich Griaznov, Irina I. Vasilieva, John W. Fulmer, William D. Kight
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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: 5395980Abstract: In the non-catalytic liquid phase oxidation of isobutane, it has been found that the reaction is initiated with 0.05 wt % to 0.08 wt % ditertiary butyl peroxide.Type: GrantFiled: March 21, 1994Date of Patent: March 7, 1995Assignee: Texaco Chemical Inc.Inventors: Mark A. Mueller, John R. Sanderson
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Patent number: 5334771Abstract: A secondary carbon atom in an alkane, including alkyl groups attached to aromatic rings, or cycloalkane is peroxidized by molecular oxygen to the corresponding hydroperoxide in the absence of a catalyst. The peroxidation is carried out in the presence of a tertiary hydroperoxide initiator which provides the free radicals needed to maintain the reaction. The amount of tertiary alcohol in the initiator is limited. The initial product of the peroxidation contains the secondary hydroperoxide as well as unreacted hydrocarbon, unreacted tertiary hydroperoxide and tertiary alcohol. The tertiary alcohol is removed as an azeotrope with part of the unreacted hydrocarbon which may be then separated from the alcohol and recycled. A second azeotropic distillation follows where the unreacted tertiary hydroperoxide is removed as an azeotrope with the rest of the unreacted hydrocarbon. This azeotrope is directly recycled to the peroxidation reaction.Type: GrantFiled: July 14, 1993Date of Patent: August 2, 1994Assignees: ABB Lummus Crest Inc., Nitrocarbono S.A.Inventors: George Ember, Edilberto A. De Castro Netro, Rogerio F. De Lacerda
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Patent number: 5220075Abstract: A secondary carbon atom in an alkane, including alkyl groups attached to aromatic rings, or cycloalkane is oxidized by molecular oxygen to the corresponding hydroperoxide in the absence of a catalyst. The oxidation is carried out in the presence of a tertiary hydroperoxide initiator which provides the free radicals needed to maintain the reaction. The amount of tertiary alcohol in the initiator is limited.Type: GrantFiled: July 17, 1992Date of Patent: June 15, 1993Assignee: ABB Lummus Crest Inc.Inventor: George Ember
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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: 5023380Abstract: Compounds have a structure represented by Formula I:CF.sub.2 =CF-X-R-(X-CF=CF.sub.2).sub.mwherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF=CF.sub.2 ; and m is an integer of from 1 to about 3. Polymers formed from such compounds are also prepared. The compounds are preferably prepared by a method by a process comprising the steps of:(a) forming a salt having anion corresponding to a compound of Formula II:HX--R--(XH).sub.m ;wherein X, R and m are as defined for Formula I;(b) reacting the salt with a 1,2-dihalo-1,1,2, 2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III:Z-CF.sub.2 CF.sub.2 -X-R-(X-CF.sub.2 CF.sub.2 - Z).sub.Type: GrantFiled: June 9, 1989Date of Patent: June 11, 1991Assignee: The Dow Chemical CompanyInventors: David A. Babb, Bobby R. Ezzell, Katherine S. Clement
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Patent number: 4906790Abstract: A method of oxidizing secondary alkyl substituted naphthalenes with molecular oxygen in a liquid phase to hydroperoxides, carbinols or mixtures of these, which comprises: oxidizing the secondary alkyl substituted naphthalenes in the presence of an aromatic hydrocarbon having a fused ring which contains at least one methylene group therein in amounts of not more than about 1000 ppm based on the secondary alkyl substituted napththalene used.A process of producing isopropylnaphthols is also disclosed, which comprises: oxidizing diisopropylnaphthalenes with molecular oxygen in a liquid phase to diisopropylnaphthalene monohydroperoxides in the presence of (a) either an aromatic hydrocarbon having a fused ring which contains at least one methylene group therein, or a paladium catalyst soluble in the reaction mixture, and (b) an organic polar compound such as acetonitrile; and then acid-decomposing the diisopropylnaphthalene monohydroperoxide to the isopropylnaphthol.Type: GrantFiled: September 9, 1988Date of Patent: March 6, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Masaharu Ishiguro, Hisaya Miki, Nobuya Hirokane
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Patent number: 4602118Abstract: This invention deals with a process for the production of hydroperoxides from their corresponding hydrocarbons via the use of certain ketones, particularly aryl ketones, generally having strong substituent electrophilic groups, as promoters. These promoters increase the rate of thermal oxidation and improve selectivity to the hydroperoxide products.Type: GrantFiled: November 9, 1984Date of Patent: July 22, 1986Assignee: Exxon Research and Engineering Co.Inventors: Mau-Song Chou, Keith W. Wohltman
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Patent number: 4579978Abstract: Substantially quantitative yields of bibenzyl hydroperoxide and bibenzyl dihydroperoxide can be obtained when oxygen is reacted with bibenzyl (1,2-diphenylethane) in the presence of a minor amount of sodium bicarbonate at a temperature within the range of about 100.degree. to about 160.degree. C. to provide an oxidation product wherein the bibenzyl is substantially selectively converted to the bibenzyl hydroperoxides. The bibenzyl hydroperoxides can be used as raw materials for the production of propylene oxide by reacting the bibenzyl hydroperoxides with propylene.Type: GrantFiled: November 13, 1984Date of Patent: April 1, 1986Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John R. Sanderson
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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: 4487974Abstract: A method of preparing 1-phenyl cyclohexylhydroperoxide by contacting a mixture of cyclohexylbenzene, an alkali or alkaline earth metal salt of cumene hydroperoxide, and an alkali or alkaline earth metal salt of phenol or a substituted phenol with an oxygen containing gas under effective reaction conditions of temperature and pressure.Type: GrantFiled: February 24, 1983Date of Patent: December 11, 1984Assignee: Texaco Inc.Inventor: John R. Sanderson
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Patent number: 4450303Abstract: High selectivities (>90%) for the production of secondary-alkyl substituted benzene hydroperoxides are achieved by heating a secondary-alkyl substituted benzene in the presence of oxygen and a samarium salt. Preferably, a free radical initiator is also present.Type: GrantFiled: February 23, 1983Date of Patent: May 22, 1984Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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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: 4299991Abstract: Hydroperoxidizable hydrocarbons are hydroperoxidized by contacting them at hydroperoxidation conditions in the presence of a catalyst comprising a polymer containing maleimide linkages. For example, cumyl hydroperoxide can be produced by contacting cumene and oxygen with a catalyst comprising polymaleimide.Type: GrantFiled: December 28, 1979Date of Patent: November 10, 1981Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Curtie E. Uebele, Serge R. Dolhyj
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Patent number: 4293719Abstract: Hydroperoxides, such as cyclohexylbenzene hydroperoxide, are manufactured by the oxidation of aryl compounds, such as cyclohexylbenzene, in the presence of a catalyst selected from the group consisting of C.sub.6 -C.sub.18 primary amines and polyvinylpyrrolidone.Type: GrantFiled: March 31, 1980Date of Patent: October 6, 1981Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Serge R. Dolhyj, Marcia H. Sundeen
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Patent number: 4282383Abstract: Cyclohexylbenzene and dicyclohexylbenzenes are converted to the corresponding hydroperoxides in the presence of t-butyl, cumene, or p-diisopropylbenzene hydroperoxides and a free radical initiator. The use of the combination of hydroperoxide and free radical initiator enables the reaction to be carried out at lower temperatures (80.degree.-105.degree. C.) than can be employed with hydroperoxides or free radical initiators alone and gives high (90%) selectivity and good conversion (20% or higher).Type: GrantFiled: December 19, 1977Date of Patent: August 4, 1981Assignee: The Upjohn CompanyInventors: Sheng-Hong A. Dai, Chung-Yuan Lin, Fred A. Stuber
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Patent number: 4282382Abstract: A process for preparation of cyclohexylbenzene hydroperoxide comprising reacting cyclohexylbenzene with oxygen in a diluent consisting essentially of cyclohexane under conditions suitable for converting said cyclohexylbenzene to cyclohexylbenzene hydroperoxide.Type: GrantFiled: July 2, 1979Date of Patent: August 4, 1981Assignee: Phillips Petroleum CompanyInventor: Yulin Wu
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Patent number: 4255592Abstract: An aromatic primary hydroperoxide is produced by oxidizing a methyl-substituted aromatic compound in a liquid phase with a molecular oxygen-containing gas at a temperature of 80.degree.-150.degree. C. under a pressure of the atmospheric to 100 kg/cm.sup.2 gage in the presence of 8-300 parts by weight of an aliphatic tertiary hydroperoxide per 100 parts by weight of the methyl-substituted aromatic compound. The oxidation reaction is promoted, an aromatic primary hydroperoxide content of the reaction products is increased, whereas by-products are reduced, and a selectivity to the aromatic primary hydroperoxide is considerably increased.Type: GrantFiled: September 27, 1979Date of Patent: March 10, 1981Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yoshio Kawai, Koichi Kida, Hideo Ikarashi, Tsukasa Toki, Yoshiharu Suzuki
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Patent number: 4239929Abstract: Alkyl cyclohexa-1,3-dienes are aromatized with sulfur dioxide and oxygen. Cyclohexa-1,4-dienes are aromatized with sulfur dioxide. Conjugated dienic hydrocarbons, including alkyl cyclohexa-1,3-dienes, are converted to beta-olefinic peroxides by sulfur dioxide and oxygen. The aromatization reactions are useful as part of the synthesis of selected aromatics from acyclic olefins. The beta-olefinic peroxides are useful intermediates in the production of 1,4-diols.Type: GrantFiled: November 1, 1978Date of Patent: December 16, 1980Assignee: Allied Chemical CorporationInventors: Divakaran Masilamani, Milorad M. Rogic