Alicyclic Hydroperoxide Produced Patents (Class 568/570)
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Patent number: 9586898Abstract: In a process for oxidizing a feed comprising cyclohexylbenzene, the feed is contacted with oxygen and an oxidation catalyst in a plurality of reaction zones connected in series, the contacting being conducted under conditions being effective to oxidize part of the cyclohexylbenzene in the feed to cyclohexylbenzene hydroperoxide in each reaction zone. At least one of the plurality of reaction zones has a reaction condition that is different from another of the plurality of reaction zones. The different reaction conditions may include one or more of (a) a progressively decreasing temperature and (b) a progressively increasing oxidation catalyst concentration as the feed flows from one reaction zone to subsequent reaction zones in the series.Type: GrantFiled: August 16, 2011Date of Patent: March 7, 2017Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad Mohammed Dakka, Francisco Manuel Benitez, Bryan Amrutlal Patel, Edmund John Mozeleski
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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: 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: 8846980Abstract: A method for preparing an alkyl hydroperoxide obtained by the oxidation of a saturated hydrocarbon using oxygen, preferably of a saturated cyclic hydrocarbon, is described. Also described, is a method for preparing cyclohexyl hydroperoxide by oxidizing cyclohexane with molecular oxygen or a gas containing molecular oxygen preferably in the absence of a catalyst.Type: GrantFiled: January 14, 2011Date of Patent: September 30, 2014Assignee: Rhodia OperationsInventors: Françoise Igersheim, Stéphane Streiff, Serge Veracini
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Patent number: 8835695Abstract: A method for oxidizing saturated hydrocarbons with oxygen, preferably saturated cyclic hydrocarbons such as cyclohexane, to produce alkyl hydroperoxide is described. A method for oxidizing saturated hydrocarbons with oxygen in a plurality of consecutive steps to control the rate of the reaction and obtain a high degree of alkyl hydroperoxide selectivity is also described. The described methods can relate to methods for condensing oxidation gases recovered in an oxidation reactor and recycling thereof.Type: GrantFiled: December 7, 2010Date of Patent: September 16, 2014Assignee: Rhodia OperationsInventors: Philippe Le Port, Thierry Mante
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Patent number: 8809595Abstract: The invention relates to a process for recovering monoalkylbenzene from a gas stream comprising oxygen and monoalkylbenzene, —wherein the gas stream comprising oxygen and monoalkylbenzene is contacted with a liquid stream comprising polyalkylbenzene, a compound comprising two phenyl groups connected to each other via a C1-C3 alkylene bridge or a mixture thereof. Further, the present invention relates to a process for preparing alkyl phenyl hydroperoxide incorporating said monoalkylbenzene recovery.Type: GrantFiled: December 24, 2010Date of Patent: August 19, 2014Assignee: Shell Oil CompanyInventor: Malcolm John Hawton
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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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Publication number: 20140148569Abstract: In a process for oxidizing a feed comprising cyclohexylbenzene, the feed is contacted with oxygen and an oxidation catalyst in a plurality of reaction zones connected in series, the contacting being conducted under conditions being effective to oxidize part of the cyclohexylbenzene in the feed to cyclohexylbenzene hydroperoxide in each reaction zone. At least one of the plurality of reaction zones has a reaction condition that is different from another of the plurality of reaction zones. The different reaction conditions may include one or more of (a) a progressively decreasing temperature and (b) a progressively increasing oxidation catalyst concentration as the feed flows from one reaction zone to subsequent reaction zones in the series.Type: ApplicationFiled: August 16, 2011Publication date: May 29, 2014Applicant: ExxonMobil Chemical Patents Inc.Inventors: Jihad Mohammed Dakka, Francisco Manuel Benitez, Bryan Amrutlal Patel, Edmund John Mozeleski
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Patent number: 8722941Abstract: A method for making alkyl hydroperoxide compounds, specifically the preparation of cyclohexyl hydroperoxide is described. The preparation of cyclohexyl hydroperoxide by means of the oxidation of cyclohexane by oxygen in a multi-stage reactor or in reactors connected in series is also described. In these methods, the reactor surfaces in contact with the oxidation medium can be protected by a layer of heat-resistant PFA polymer.Type: GrantFiled: November 2, 2010Date of Patent: May 13, 2014Assignee: Rhodia OperationsInventors: Fabien Bellenger, Laurent Diguet, Stéphane Streiff
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Patent number: 8710100Abstract: The present invention relates to compounds comprising the general formula (I), in which R1 and R2, which may be identical or different, are selected from the group comprising —H or a linear or branched alkyl group having from 1 to 6 carbon atoms or together form an aromatic or aliphatic ring with 5 or 6 atoms; Y and Z, which may be identical or different, are selected from the group comprising —H, —OH, —COOH, —OR3, —CH(OR3)COOH, in which R3 is selected from H, phenyl, benzyl, —CF3 or —CF2CF3, vinyl, allyl and a linear or branched alkyl group having from 1 to 6 carbon atoms.Type: GrantFiled: February 29, 2012Date of Patent: April 29, 2014Assignee: Nogra Pharma LimitedInventors: Giancarlo Naccari, Sergio Baroni
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Patent number: 8658836Abstract: 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 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 an element 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: GrantFiled: October 8, 2008Date of Patent: February 25, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Francisco M. Benitez, Jihad M. Dakka, Edmund J. Mozeleski, Stephen Zushma, John Scott Buchanan, Jon E. Stanat
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Patent number: 8658835Abstract: In a process for oxidizing a hydrocarbon to a corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, the hydrocarbon is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide. The contacting produces an effluent comprising an oxidized hydrocarbon product and unreacted imide catalyst and the effluent is treated with at least one solid sorbent to remove at least part of the unreacted imide catalyst and produce a treated effluent comprising said oxidized hydrocarbon product. The organic phase can then be recovered.Type: GrantFiled: July 13, 2010Date of Patent: February 25, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Kun Wang, Jihad M. Dakka, Stephen Zushma
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Publication number: 20130274524Abstract: 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: ApplicationFiled: May 28, 2013Publication date: October 17, 2013Inventors: Jihad M. Dakka, Stephen Zushma, Jon E.R. Stanat
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Publication number: 20130202522Abstract: The invention relates to hydroalkylation processes. In the processes, a hydrogen stream comprising hydrogen and an impurity is treated to reduce the amount of the impurity in the hydrogen stream. The hydrogen is then hydroalkylated with benzene to form at least some cyclohexylbenzene. The processes also relate to treating a benzene stream comprising benzene and an impurity with an adsorbent to reduce the amount of the impurity in the benzene stream. The hydroalkylation processes described herein may be used as part of a process to make phenol.Type: ApplicationFiled: April 4, 2011Publication date: August 8, 2013Inventors: Tan-Jen Chen, Teng Xu, Terry Helton, Francisco M. Benitez, Charles M. Smith
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Publication number: 20130184494Abstract: According to the first embodiment of the present invention, an oxide of a hydrocarbon compound can be produced with high yield and high productivity by oxidizing the hydrocarbon compound with molecular oxygen in the co-presence of an N-hydroxy compound, such as methyl ethyl ketone or N-hydroxysuccinimide, and a phosphate ester, such as dibutyl phosphate. According to another embodiment of the present invention, an oxide of a hydrocarbon compound can be produced with high yield by using an oxidation catalyst that comprises an oxime compound, such as methyl ethyl ketone. According to another embodiment of the present invention, an alcohol and/or a ketone can be produced with high yield by oxidizing the hydrocarbon compound at a temperature of 160° C. or less, and by decomposing the resulting hydroperoxide, for example, in a unit having an inner surface formed by a material from which no transition metal ion is generated.Type: ApplicationFiled: September 26, 2011Publication date: July 18, 2013Applicant: USE Industries, Ltd.Inventors: Kazunori Kurosawa, Joji Funatsu, Naoya Katagiri, Junichi Kugimoto
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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: 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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Patent number: 8420867Abstract: 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 consisting of an N-hydroxyimide associated with a peroxide activator having a peracid or dioxyrane structure, possibly generated in situ.Type: GrantFiled: March 13, 2009Date of Patent: April 16, 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: 20130046115Abstract: A method for preparing an alkyl hydroperoxide obtained by the oxidation of a saturated hydrocarbon using oxygen, preferably of a saturated cyclic hydrocarbon, is described. Also described, is a method for preparing cyclohexyl hydroperoxide by oxidizing cyclohexane with molecular oxygen or a gas containing molecular oxygen preferably in the absence of a catalyst.Type: ApplicationFiled: January 14, 2011Publication date: February 21, 2013Applicant: RHODIA OPERATIONSInventors: Françoise Igersheim, Stéphane Streiff, Serge Veracini
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Publication number: 20120310017Abstract: A method for oxidizing saturated hydrocarbons with oxygen, preferably saturated cyclic hydrocarbons such as cyclohexane, to produce alkyl hydroperoxide is described. A method for oxidizing saturated hydrocarbons with oxygen in a plurality of consecutive steps to control the rate of the reaction and obtain a high degree of alkyl hydroperoxide selectivity is also described. The described methods can relate to methods for condensing oxidation gases recovered in an oxidation reactor and recycling thereof.Type: ApplicationFiled: December 7, 2010Publication date: December 6, 2012Inventors: Philippe Le Port, Thierry Mante
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Publication number: 20120283482Abstract: A method for making alkyl hydroperoxide compounds, specifically the preparation of cyclohexyl hydroperoxide is described. The preparation of cyclohexyl hydroperoxide by means of the oxidation of cyclohexane by oxygen in a multi-stage reactor or in reactors connected in series is also described. In these methods, the reactor surfaces in contact with the oxidation medium can be protected by a layer of heat-resistant PFA polymer.Type: ApplicationFiled: November 2, 2010Publication date: November 8, 2012Applicant: RHODIA OPERATIONSInventors: Fabien Bellenger, Laurent Diguet, Stéphane Streiff
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Publication number: 20120157647Abstract: A rubber-modified polymeric composition having predominately core-shell morphology is disclosed. The rubber-modified polymeric composition can be a polystyrene comprising styrene, polybutadiene, and a high-grafting initiator formed by contacting singlet oxygen with an olefin containing an allylic hydrogen or a diene to form a hydroperoxide or peroxide. The singlet oxygen can be formed by contacting ground state oxygen with a photo catalyst, such a photosensitive dye exposed to light.Type: ApplicationFiled: February 15, 2012Publication date: June 21, 2012Applicant: Fina Technology, Inc.Inventor: Olga Khabashesku
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Publication number: 20120149941Abstract: In a process for oxidizing a hydrocarbon to a corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, the hydrocarbon 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 13, 2010Publication date: June 14, 2012Inventors: Kun Wang, Jihad M. Dakka, Stephen Zushma
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Patent number: 8093433Abstract: A process for producing an alkylbenzene hydroperoxide from an alkylbenzene solution containing 0.01 to 10 mmol/kg of phenols by subjecting the solution to oxidation with an oxygen-containing gas, including allowing a compound represented by formula (I) to be present in the alkylbenzene solution: wherein R1, R2, R3, R4 and R5 independently represent a hydrogen atom, an alkyl group or an aryl group and may combine with each other to form a non-aromatic ring, the molar ratio of the compound represented by formula (I) to the phenols in the alkylbenzene solution being 0.4 mol/mol or higher; is advantageous in providing economical and high-yield production of an alkylbenzene hydroperoxide.Type: GrantFiled: October 28, 2008Date of Patent: January 10, 2012Assignee: Sumitomo Chemical Company, LimitedInventor: Masayuki Yoshii
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Publication number: 20110301384Abstract: A process for oxidizing cumene to cumene hydroperoxide using an oxygen containing gas, which process composes—conducting a cumene feed and an oxygen containing gas feed to at least the first oxidation reactor in a series of 3-8 reactors, thereby forming an oxidation mixture, and—conducting the oxidation mixture from one oxidation reactor to at least one subsequent reactor, wherein—the reactors are operated with reducing liquid levels; —the oxidation is operated as a dry oxidation, whereby the only gaseous feeds conducted to the oxidation reactors are the cumene feed and the oxygen containing gas feed; —the oxygen containing gas feed is washed with caustic and then with water to remove all acidic or caustic traces before conducting it into an oxidation reactor; —the pressure within each oxidation reactor is in the range of 0-10 barg; —the off-gases from the top section of each oxidation reactor are separated and cooled, whereby a condensate containing unreacted cumene is formed, and—washing the condensate andType: ApplicationFiled: December 17, 2009Publication date: December 8, 2011Applicant: BOREALIS AGInventors: Veli-Matti Purola, Anja Mannerla
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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: 20110082320Abstract: 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 consisting of an N-hydroxyimide associated with a peroxide activator having a peracid or dioxyrane structure, possibly generated in situ.Type: ApplicationFiled: March 13, 2009Publication date: April 7, 2011Applicant: Polimeri Europa S.P.A.Inventors: Francesco Minisci, Ombretta Porta, Carlo Punta, Francesco Recupero, Cristian Gambarotti, Raffaele Spaccini, Angelo Clerici, Alberto Clerici
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Publication number: 20100234589Abstract: In a process for oxidizing a hydrocarbon to a corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, the hydrocarbon 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 an element of Group 4 of the Periodic Table; Y is O or OH; k is 0, 1, or 2; 1 is 0, 1, or 2; m is 1 to 3, and R3 can be any of the entities listed for R1.Type: ApplicationFiled: July 11, 2008Publication date: September 16, 2010Inventors: Jihad M. Dakka, James C. Vartuli, Stephen Zushma
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Patent number: 7741523Abstract: The present invention relates to a continuous method for oxidizing saturated cyclic hydrocarbons by oxygen to obtain a mixture of hydroperoxides, alcohols and ketones. It relates more particularly to a method for oxidizing cyclohexane in a column forming a bubble reactor, for the formation of cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone. According to the invention, the column may be supplied with oxygen-enriched air, while meeting the maximum oxygen concentration requirements in the headspace of the reactor to avoid any risk of explosion.Type: GrantFiled: October 6, 2005Date of Patent: June 22, 2010Assignee: Rhodia ChimieInventors: Serge Veracini, Frédéric Augier
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Patent number: 7692046Abstract: A promoter can have utility in selective heterogeneous oxidation of arylalkyl hydrocarbons such as, for example, cyclohexyl benzene and/or sec-butyl benzene to form hydroperoxides. The promoter can include the product of contacting a solid support comprising a metal oxide surface and an iron compound. The solid support can include, for example, titanium dioxide and/or an iron oxide such as magnetite and can have magnetic susceptibility. A method for the oxidation of arylalkyl hydrocarbons to form hydroperoxides can include contacting 16 an arylalkyl hydrocarbon with oxygen in the presence of the promoter under catalytic oxidation conditions to form arylalkyl hydroperoxide, which can then be converted to phenol via cleavage 26. The method can include recovery 22 of the promoter from the arylalkyl hydroperoxide and can further include recycling the recovered promoter to the contacting 16. Where the solid support has magnetic susceptibility, the recovery 22 can include magnetic separation of the promoter.Type: GrantFiled: June 21, 2007Date of Patent: April 6, 2010Assignee: ExxonMobil Chemical Patents Inc.Inventors: Matthew W. Holtcamp, Renuka N. Ganesh, Tan-Jen Chen, Jihad M. Dakka
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Publication number: 20080319234Abstract: A promoter can have utility in selective heterogeneous oxidation of arylalkyl hydrocarbons such as, for example, cyclohexyl benzene and/or sec-butyl benzene to form hydroperoxides. The promoter can include the product of contacting a solid support comprising a metal oxide surface and an iron compound. The solid support can include, for example, titanium dioxide and/or an iron oxide such as magnetite and can have magnetic susceptibility. A method for the oxidation of arylalkyl hydrocarbons to form hydroperoxides can include contacting 16 an arylalkyl hydrocarbon with oxygen in the presence of the promoter under catalytic oxidation conditions to form arylalkyl hydroperoxide, which can then be converted to phenol via cleavage 26. The method can include recovery 22 of the promoter from the arylalkyl hydroperoxide and can further include recycling the recovered promoter to the contacting 16. Where the solid support has magnetic susceptibility, the recovery 22 can include magnetic separation of the promoter.Type: ApplicationFiled: June 21, 2007Publication date: December 25, 2008Inventors: Matthew W. Holtcamp, Renuka N. Ganesh, Tan-Jen Chen, Jihad M. Dakka
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Patent number: 7446232Abstract: In a process for oxidizing alkylaromatic compounds to the corresponding hydroperoxide, an alkylaromatic compound of 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, with oxygen in the presence of an added catalyst comprising tert-butyl hydroperoxide and in the absence of any other catalyst, to produce a hydroperoxide of general formula (II): in which R1, R2 and R3 have the same meaning as in formula (I). The hydroperoxide may then be converted into a phenol and a ketone of the general formula R1COCH2R2 (III), in which R1 and R2 have the same meaning as in formula (I).Type: GrantFiled: July 13, 2007Date of Patent: November 4, 2008Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad Mohammed Dakka, Doron Levin, John Scott Buchanan, Jon Edmond Randolph Stanat
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Patent number: 7053161Abstract: A process for producing organic peroxide initiators useful in the polymerization of ethylenically unsaturated monomers. The process for making the organic peroxides includes forming an aqueous emulsion of the organic peroxide. The organic peroxide is dispersed as small droplets of from 1 to 10 microns in size in the aqueous emulsion. The organic peroxide may be added to a polymerization reactor containing an ethylenically unsaturated monomer. The organic peroxide functions as a free radical initiator to polymerize the monomer. The organic peroxide may be substantially free of organic solvents and plasticizers. The resulting polymers are of high quality.Type: GrantFiled: January 12, 2005Date of Patent: May 30, 2006Assignee: Oxy Vinyls, L.P.Inventors: Ross J. Cozens, Qi Wang, M. Fredrick V. Glock, Jr., Daniel A. Zust
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Patent number: 6459002Abstract: Cyclohexanone, cyclohexanol and/or cyclohexyl hydroperoxide are prepared at a high productivity by allowing cyclohexane to be in contact with an oxygen-containing gas using a catalyst comprising a cyclic N-hydroxyimide and a transition metal compound in the presence of cyclohexanone and optional cyclohexanol.Type: GrantFiled: November 26, 2001Date of Patent: October 1, 2002Assignees: Sumitomo Chemical Company, Limited, Daicel Chemical Industries, Ltd.Inventors: Shuzo Murata, Nobuhiro Tani
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Patent number: 6037491Abstract: This invention relates to methods and devices of preparing acids, such as adipic acid for example, by oxidizing a hydrocarbon, such as cyclohexane for example, with a gas containing an oxidant, preferably oxygen. A respective hydrocarbon is reacted, preferably at a steady state, with a gaseous oxidant to form an acid in a liquid mixture which preferably contains a solvent, a catalyst, water, and an initiator. The ratio of solvent to hydrocarbon may be controlled in a manner to maintain in the reaction zone maximum reaction rate and/or reactivity, or reaction rate and/or reactivity within a desired range, or reaction rate and/or reactivity directed toward a desired range. In addition, the ratio of solvent to hydrocarbon is controlled in a manner to maintain in the reaction zone substantially maximum selectivity and/or yield, or selectivity and/or yield within a desired range, or selectivity and/or yield directed toward a desired range.Type: GrantFiled: July 25, 1997Date of Patent: March 14, 2000Assignee: RPC Inc.Inventors: Eustathios Vassiliou, Mark W. Dassel, Sharon M. Aldrich, Ader M. Rostami, David C. DeCoster
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Patent number: 6011183Abstract: The invention relates to a process for preparing organic hydroperoxides by oxidation of a hydrocarbon feed with molecular oxygen at supercritical conditions, which process is carried out in the presence of a separate liquid water phase that is present in an amount of 0.5 to 20% weight on the weight of the feed as a water film on the inner walls of the reactor vessel.Type: GrantFiled: November 13, 1998Date of Patent: January 4, 2000Assignee: Shell Oil CompanyInventors: Stephen William Bourne, Pieter Oldenhove
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Patent number: 5817868Abstract: Methods and devices for controlling the oxidation of a hydrocarbon to an acid by regulating the temperature, hold-up time, and conversion in consecutive reaction zones. The temperature in the consecutive reaction zones progressively decreases, while the hold-up time increases. Preferably, the conversion also increases. One of the major advantages of the methods and devices of the present invention is that an outstanding balance between productivity and selectivity/yield of the desired acid may be achieved. In this respect high yields and selectivities may be obtained without sacrificing productivity.Type: GrantFiled: May 21, 1997Date of Patent: October 6, 1998Assignee: Twenty-First Century Research CorporationInventors: Ader M. Rostami, Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster
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Patent number: 5801273Abstract: Methods and devices for controlling the reaction rate of a hydrocarbon to an acid or other intermediate oxidation product by pressure drop rate adjustments. The pressure drop rate measurements are conducted at predetermined time intervals, after stopping the feeding and exiting of gases. The pressure drop at a predetermined time interval is measured or the time it takes for the pressure to drop by a certain degree. Adjustments are then made in one or more temperature, feeding rates of hydrocarbon, solvent, catalyst, promoter, and the like until the pressure drop rate and the reaction rate fall within desirable predetermined limits.Type: GrantFiled: May 21, 1997Date of Patent: September 1, 1998Assignee: Twenty-First Century Research CorporationInventors: Eustathios Vassiliou, Mark W. Dassel, David C. DeCoster, Ader M. Rostami, Sharon M. Aldrich
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Patent number: 5801282Abstract: Methods of making intermediate oxidation products by atomizing a first liquid (in the form of droplets) containing a reactant into a gas containing an oxidant in a manner to form an intermediate oxidation product different than carbon monoxide and/or carbon dioxide. The oxidation is controlled by monitoring the pre-coalescing temperature (temperature of the droplets just before they coalesce into a mass of liquid), or transient temperature difference (difference between the pre-coalescing temperature and the temperature of the droplets just before atomized), or transient conversion (conversion taking place in the time interval between the formation of the droplets and their coalescence into a mass of liquid) or a combination thereof.Type: GrantFiled: June 7, 1995Date of Patent: September 1, 1998Assignee: Twenty-First Century Research CorporationInventors: Mark William Dassel, Eustathios Vassiliou
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Patent number: 5654475Abstract: Methods of making intermediate oxidation products by atomizing a first liquid (in the form of droplets) containing a reactant into a gas containing an oxidant in a manner to form an intermediate oxidation product different than carbon monoxide and/or carbon dioxide. The oxidation rate is controlled by monitoring and adjusting the temperatures and/or conversions at critical points of the process.Type: GrantFiled: March 25, 1996Date of Patent: August 5, 1997Assignee: Twenty-First Century Research CorporationInventors: Eustathios Vassiliou, Mark William Dassel
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Patent number: 5502245Abstract: Methods of making intermediate oxidation products by atomizing a first liquid containing a reactant into a gas containing an oxidant in a manner to form an intermediate oxidation product different than carbon monoxide and/or carbon dioxide. The oxidation is controlled by monitoring the transient conversion (conversion taking place in the time interval between the formation of the droplets and their coalescence into a mass of liquid) of first reactant to oxidation product just before the droplets coalesce into a mass of a second liquid.Type: GrantFiled: June 7, 1995Date of Patent: March 26, 1996Assignee: Twenty-First Century Research CorporationInventors: Mark W. Dassel, Eustathios Vassiliou
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Patent number: 5475147Abstract: Isobutane containing a significant amount of isobutylene is treated at conditions effective to oligomerize a predominance of the isobutylene, isobutane substantially free of isobutylene is separated from the oligomer products, and the isobutane substantially free of isobutylene is oxidized to tertiary butyl hydroperoxide.Type: GrantFiled: October 19, 1994Date of Patent: December 12, 1995Assignee: ARCO Chemical Technology, L.P.Inventor: Thomas S. Zak
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Patent number: 5406001Abstract: The present invention relates to a method for the continuous preparation of a mixture of a cycloalkanone, a cycloalkanol and a cycloalkylhydroperoxide. In the method, a cycloalkane, corresponding to the cycloalkenone, cycloalkenol and cycloalkylhydroperoxide, is oxidized in a continuous process, with the aid of an oxygen-containing gas, in the absence of a metal catalyst, at a temperature of between 130.degree. C. and 200.degree. C. The oxidation is at least partly carried out in the presence of between 0.002 and 2 mmol of a phenolic compound per kg of reaction mixture (mmol/kg).Type: GrantFiled: December 15, 1993Date of Patent: April 11, 1995Assignee: DSM N.V.Inventors: Johannes G. H. M. Housmans, Ubaldus F. Kragten
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Patent number: 5399777Abstract: 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 % tertiary butyl hydroperoxide.Type: GrantFiled: March 21, 1994Date of Patent: March 21, 1995Assignee: Texaco Chemical Inc.Inventor: Mark A. Mueller
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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: 5095143Abstract: A method to oxidize an oxidizable component in a liquid phase with an oxygen-containing gas is disclosed. The method comprises mixing the liquid phase and gas phase in a reactor with a rotating agitator element operated at constant power.Type: GrantFiled: June 13, 1990Date of Patent: March 10, 1992Assignee: Amoco CorporationInventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
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Patent number: 5043481Abstract: The present invention relates to the oxidation of a cycloalkane to produce a product comprised of cycloalkylhydroperoxide with the removal of a vapor stream from the oxidation zone wherein oxidation products such as hydroperoxide, cycloalkanol and cycloalkanone are separated from the removed stream before the stream is recycled to the oxidation zone.Type: GrantFiled: September 28, 1990Date of Patent: August 27, 1991Assignee: Arco Chemical Technology, Inc.Inventor: Robert Nedwick
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Patent number: 5030739Abstract: The invention is directed to a process for the catalytic oxidation of an isoprenoid containing at least one allylic hydrogen atom, which process comprises reacting the isoprenoid with oxygen or an oxygen-containing gas in an inert solvent in the presence of a N-hydroxydicarboxylic acid imide of the formula ##STR1## wherein A-B stands for CH.sub.2 -CH.sub.2, CH.dbd.CH, an aromatic hydrocarbon residue or a group derived from one of these groups in which one or more hydrogen atoms is/are replaced by alkyl or halogen,to produce a primary of secondary hydroperoxide.The process of the invention is suitable for the manufacture of steroids, vitamins, odorant substances, carotinoids and the like.Type: GrantFiled: August 31, 1990Date of Patent: July 9, 1991Assignee: Hoffman-La Roche Inc.Inventors: Joseph Foricher, Claude Furbringer, Karlheinz Pfoertner
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Patent number: 4962040Abstract: 2-Hydrazono-4,6-dinitrobenzthiazolones of the formula ##STR1## in which X.sub.1 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -hydroxyalkyl, C.sub.1 -C.sub.4 -sulphoalkyl or C.sub.1 -C.sub.4 -sulphatoalkyl, andX.sub.2 represents hydrogen or --SO.sub.2 X.sub.3, whereX.sub.3 may represent hydrogen, C.sub.1 -C.sub.8 -alkyl or optionally substituted aryl andX.sub.1 also represents a double bond between the cyclic nitrogen atom and the carbon atom 2 according to the formula II below: ##STR2## where X.sub.2 has the meaning specified under the above formula. These hydrazones may be employed in the preparation of azo dyestuffs and as color formers for detecting of biological substances, and in the determination of H.sub.2 O.sub.2.Type: GrantFiled: August 10, 1989Date of Patent: October 9, 1990Assignee: Bayer AktiengesellschaftInventors: Herbert Hugl, Aloysius Engel, Klaus Wehling