Preparing By Oxidation Utilizing Gaseous Oxygen Patents (Class 568/569)
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Patent number: 9073840Abstract: 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: GrantFiled: August 16, 2011Date of Patent: July 7, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Christopher L. Becker, Jihad M. Dakka, Francisco M. Benitez, Edmund J. Mozeleski
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Patent number: 8975444Abstract: 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: GrantFiled: December 17, 2009Date of Patent: March 10, 2015Assignee: Borealis AGInventors: Veli-Matti Purola, Anja Mannerla
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Patent number: 8952202Abstract: The present invention concerns a process for oxidizing cumene to cumene hydroperoxide using an oxygen containing gas, preferably air, which process comprises —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 formed oxidation mixture from one reactor to the next, preferably after an oxidation reaction has taken place, wherein —the reactors comprise at least one lower pressure oxidizer (1) as the first reactor in the series and at least one higher pressure oxidizer (2) as the last reactor in the series; —any lower pressure oxidizer is operated at a pressure of at least atmospheric pressure and any higher pressure oxidizer is operated at a pressure of at least 0.5 bar higher than said at least one lower pressure oxidizer.Type: GrantFiled: December 17, 2009Date of Patent: February 10, 2015Assignee: Borealis AGInventor: Veli-Matti Purola
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Patent number: 8884065Abstract: In a process for producing a cycloalkylaromatic compound, an aromatic compound and a cyclic olefin are contacted with a first catalyst under conditions effective to produce a reaction product comprising the cycloalkylaromatic compound and at least one non-fused bicyclic by-product. The at least one non-fused bicyclic by-product is then contacted with a second catalyst under conditions effective to convert at least a portion of the at least one non-fused bicyclic by-product to a converted by-product.Type: GrantFiled: October 25, 2011Date of Patent: November 11, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Kun Wang, Jihad M. Dakka, Stephen Zushma, James R. Lattner, Christopher L. Becker, Tan-Jen Chen
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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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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: 8575398Abstract: The purpose of the present invention is to provide an advantageous non-barbotage method for oxidation of hydrocarbons, that, when implemented in various embodiments thereof, provides significantly higher selectivity, a greater level of safety, lower capital costs, etc., than conventional oxidation processes utilizing the barbotage technique. The essence of the inventive non-barbotage oxidation process is ensuring that the oxidizing agent delivered to the process reactor undergoes continued contact only with exposed surfaces of the liquid phase of the hydrocarbons being oxidized configured as at least one of: formed liquid phase thin film(s), liquid phase continuous stream(s), and/or liquid phase globule (e.g., droplets, etc.Type: GrantFiled: October 29, 2010Date of Patent: November 5, 2013Assignee: Illa International, LLCInventor: Vladimir Mikhailovitch Zakoshansky
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Patent number: 8569547Abstract: 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 a naphthalene compound. Further, the present invention relates to a process for preparing alkyl phenyl hydroperoxide incorporating said monoalkylbenzene recovery.Type: GrantFiled: December 21, 2010Date of Patent: October 29, 2013Assignee: Shell Oil CompanyInventor: Johannes Gerhardus Joseph Beckers
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Publication number: 20130211036Abstract: 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: ApplicationFiled: August 16, 2011Publication date: August 15, 2013Applicant: ExxonMobil Chemical Company - Law TechnologyInventors: Jihad M. Dakka, Edmund J. Mozeleski, Charles Morris Smith, Christopher L. Becker, 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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Publication number: 20130131388Abstract: 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: ApplicationFiled: December 24, 2010Publication date: May 23, 2013Inventor: Malcolm John Hawton
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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: 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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Publication number: 20120283481Abstract: 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 a naphthalene compound. Further, the present invention relates to a process for preparing alkyl phenyl hydroperoxide incorporating said monoalkylbenzene recovery.Type: ApplicationFiled: December 21, 2010Publication date: November 8, 2012Inventor: Johannes Gerhardus Joseph Beckers
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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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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: 20110263905Abstract: The present invention concerns a process for oxidizing cumene to cumene hydroperoxide using an oxygen containing gas, preferably air, which process comprises—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 formed oxidation mixture from one reactor to the next, preferably after an oxidation reaction has taken place, wherein—the reactors comprise at least one lower pressure oxidizer (1) as the first reactor in the series and at least one higher pressure oxidizer (2) as the last reactor in the series; —any lower pressure oxidizer is operated at a pressure of at least atmospheric pressure and any higher pressure oxidizer is operated at a pressure of at least 0.5 bar higher than said at least one lower pressure oxidizer.Type: ApplicationFiled: December 17, 2009Publication date: October 27, 2011Applicant: BOREALIS AGInventor: Veli-Matti Purola
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Publication number: 20100317899Abstract: 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: ApplicationFiled: October 28, 2008Publication date: December 16, 2010Applicant: Sumitomo Chemical Company ,LimitedInventor: Masayuki Yoshii
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Publication number: 20100228047Abstract: 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: ApplicationFiled: October 8, 2008Publication date: September 9, 2010Inventors: Francisco M. Benitez, Jihad M. Dakka, Edmund J. Mozeleski, Stephen Zushma, John Scott Buchanan, Jon E. Stanat
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Publication number: 20100222609Abstract: 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; 1 is 0, 1, or 2; m is 1 to 3, and R3 can be any of the entities listed for R1.Type: ApplicationFiled: October 8, 2008Publication date: September 2, 2010Inventors: Jihad M. Dakka, James C. Vartuli, Stephen Zushma
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Publication number: 20090171126Abstract: 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: ApplicationFiled: June 30, 2008Publication date: July 2, 2009Applicant: ILLA INTERNATIONAL, LLCInventors: Vladimir Mikhailovitch Zakoshansky, Andrey Victorovitch Budarev
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Publication number: 20090005606Abstract: Use of a high shear mechanical device incorporated into a process for the production of cumene hydroperoxide as a mixer/reactor device is capable of decreasing mass transfer limitations, thereby enhancing the cumene hydroperoxide production process. A system for the production of cumene hydroperoxide from oxidation of cumene, the system comprising a reactor and an high shear mixer the outlet of which is fluidly connected to the inlet of the reactor; the high shear mixer capable of providing a dispersion air gas bubbles within a liquid, the bubbles having an average bubble diameter of less than about 100 ?m.Type: ApplicationFiled: June 11, 2008Publication date: January 1, 2009Applicant: H R D CORPORATIONInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 7439404Abstract: A process for the continuous production of cumene hydroperoxide (CHP) by oxidizing cumene in a liquid phase in a reactor in the presence of an oxygen-containing gas, wherein the oxygen content of the whole gas fed into the liquid phase in the reactor is adjusted to 22 to 50 mol % and the oxidation is carried out under the condition that: (1) the CHP production per unit volume of the reaction fluid in the reactor is at least 22 kg/m3/hr, (2) the oxygen content of the exhaust gas from the reactor is 2 to 10 mol %, or (3) the oxygen-containing gas is fed into the reactor by the use of a sparger whose aperture pitch is at least twice the aperture diameter. The process enhances CHP production per unit volume of the reaction fluid in the reactor, thus downsizing the reactor permitting required CHP production or enabling increased CHP production in an existing reactor.Type: GrantFiled: March 3, 2005Date of Patent: October 21, 2008Assignee: Mitsubishi Chemical CorporationInventors: Keiji Kuma, Takanori Suzuki
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Patent number: 7393984Abstract: A continuous method of cumene oxidation in a gas-liquid system is provided, where the liquid phase is represented by cumene and its oxidation products and the gas phase is represented by air. The oxidation process can be carried out either in a reactor series or in a single reactor at least one of which is preferably equipped with at least two airlift-type trays. When specific CHP concentration is achieved, the oxidation products are discharged from the to reaction zone and treated in a mixing device with aqueous ammonia or water to remove organic acids such as formic acid, benzoic acid, etc. and to remove phenol, which is an inhibitor of oxidation reaction. The cumene oxidation product stream, free of organic acids and phenol is recycled to the same reactor in the case of single reactor, or is passed to the next reactor of the series in the case of reactor series.Type: GrantFiled: November 1, 2007Date of Patent: July 1, 2008Assignee: ILLA International, LLCInventors: Vladimir Zakoshansky, Irina Vassilieva, Andrey Budarev, Vasiliy Trubaev, Sergey Korchagin
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Patent number: 7087801Abstract: A reactor system for oxidative conversion of hydrocarbons comprising at least one reactor tube being provided with a plurality of perforations along a wall of the tube and a reaction zone with an active catalyst arranged on tube side and/or shell side of the reactor tube; and a bed of particulates material surrounding the at least one reactor tube, the bed of particulate material being adapted to be fluidised by an oxygen containing atmosphere and to transport heat from the reactor tube.Type: GrantFiled: October 17, 2003Date of Patent: August 8, 2006Assignee: Haldor Topsoe A/SInventors: Jens Perregaard, Gregory Patience
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Patent number: 7038089Abstract: The invention relates to a process for preparing hydroperoxides from their corresponding hydrocarbons which comprises oxidizing said hydrocarbons, particularly ethylbenzene, with an oxygen containing gas in the presence of a catalyst comprising a cyclic imide compound and a compound selected from the group consisting of an alkali metal compound or mixture thereof.Type: GrantFiled: January 22, 2004Date of Patent: May 2, 2006Assignee: Respol Quimica, S.A.Inventors: Pilar De Frutos Escrig, Pedro Pablo Toribio Temprado, Raul Martos Calvente, Jose Miguel Campos Martin, Jose Luis Garcia Fierro
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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: 6956137Abstract: The invention relates to a method for oxidizing organic substrates using 1O2 in which hydrophobic organic substrates that react with 1O2 are added to an organic solvent in the presence of a heterogeneous or homogeneous catalyst with 30–70% being compr Afterwards, H2O2 is catalytically decomposed into water and 1O2, and the oxidation into corresponding oxidation products ensues.Type: GrantFiled: March 23, 2000Date of Patent: October 18, 2005Assignee: DSM Fine Chemicals Austria NFG GmbH & CO KGInventors: Jean-Marie Aubry, Veronique Rataj-Nardello, Paul Alsters
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Patent number: 6956136Abstract: The specification provides a method of producing cumene hydroperoxide by continuous aqueous-emulsion oxidation at a high temperature and pressure in a cascade of reactors, wherein the process is conducted in the presence of a mixture of an aqueous solution of an ammonium salt with a concentration of 0.001-0.5 mass % and an aqueous solution of ammonia with a concentration of 0.001-0.5 mass %, which mixture is fed into each oxidation reactor in an ammonia:ammonium salt mass ratio of 1:100 to 100:1.Type: GrantFiled: July 29, 2003Date of Patent: October 18, 2005Assignee: General Electric CompanyInventors: Arkady Samuilovich Dyckman, John William Fulmer, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov, Boris Issakovich Gorovits
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Patent number: 6943270Abstract: A cumene process of producing phenol and acetone comprises the joint oxidation of aldehydes and dimethylbenzene alcohol by aqueous hydrogen peroxide solutions in presence of 16 wt % to 94 wt % of cumene hydroperoxide by contacting of mutually insoluble phases of the organic products from a cumene oxidation stage and hydrogen peroxide containing water with optional addition of acidic catalysts in a conversion reactor for the purpose of conversion of aldehydes into organic acids and dimethylbenzene alcohol into cumene hydroperoxide and therefore significantly simplifying the process of fractionation of organic conversion products into high quality product phenol and product acetone.Type: GrantFiled: February 28, 2001Date of Patent: September 13, 2005Assignee: Illa International, LLCInventor: Vladimir Mikhailovitch Zakoshansky
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Patent number: 6852893Abstract: The invention relates to a method for oxidizing substrates such as hydrocarbons, waxes or soot. The method involves the use of a compound of formula (I) in which: R1 and R2 represent H, an aliphatic or aromatic alkoxy radical, carboxyl radical, alkoxycarbonyl radical or hydrocarbon radical, each having 1 to 20 hydrocarbon atoms, SO3H, NH2, OH, F, Cl, Br, I and/or NO2, whereby R1 and R2 designate identical or different radicals or R1 and R2 can be linked to one another via a covalent bonding; Q1 and Q2 represent C, CH, N, CR5, each being the same or different; X and Z represent C, S, CH2, each being the same or different; Y represents O and OH; k=0, 1, 2; l=0, 1, 2; m=1 to 3, and; R5 represents one of the meanings of R1. Said compound is used as a catalyst in the presence of a radical initiator, whereby the molar ratio of the catalyst to the hydrocarbon is less than 10 mol %. Peroxy compounds or azo compounds can be used as the radical initiator. Preferred substrates are aliphatic or aromatic hydrocarbons.Type: GrantFiled: March 22, 2001Date of Patent: February 8, 2005Assignee: Creavis Gesellschaft fuer Technologie and Innovation mbHInventors: Adolf Kühnle, Mark Duda, Carsten Jost, Guido Fries, Jochen Kirchhoff, Thomas Schiffer, Roger Arthur Sheldon, Sasidharan Manickam, Isabella W. C. E. Arends
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Patent number: 6700024Abstract: A process for preparing organic hydroperoxides, which process comprises: (a) oxidation of an organic compound to obtain reaction product containing organic hydroperoxide, (b) contacting at least part of the organic hydroperoxide containing reaction product with a basic aqueous solution, (c) separating hydrocarbonaceous phase containing organic hydroperoxide from aqueous phase, (d) contacting at least part of the separated hydrocarbonaceous phase containing organic hydroperoxide with an aqueous solution comprising wastewater, and (e) separating the hydrocarbonaceous phase containing organic hydroperoxide from the aqueous phase. The invention further relates to a process for preparing an oxirane compounds with the help of this process, and a to a process for preparing an alkenyl aryl with the help of this process.Type: GrantFiled: September 19, 2002Date of Patent: March 2, 2004Assignee: Shell Oil CompanyInventors: Gerard Du Cauze de Nazelle, Wan Shi Foong, Tjeerd Willem Garritsen, Raymond Lawrence June, Mohammad Azmi Bin Othman, Eduardus Petrus Simon Schouten
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Patent number: 6620974Abstract: A method for manufacturing cumene hydroperoxide comprises reacting cumene and oxygen in the presence of a water phase comprising aqueous ammonia, and in the absence of an additive comprising an alkali or alkaline earth metal, to form cumene hydroperoxide. A system for producing cumene hydroperoxide comprises a cumene feed in fluid communication with a reactor having a cumene hydroperoxide oxidate outlet; an oxygen feed in fluid communication with the reactor; and an ammonia feed in fluid communication with the cumene feed and/or the reactor, wherein the cumene feed, the oxygen feed, the ammonia feed, and the reactor are free of an additive comprising an alkali or alkaline earth metal.Type: GrantFiled: August 21, 2002Date of Patent: September 16, 2003Assignee: General Electric CompanyInventors: John William Fulmer, Eugene Edward Scott, William Dale Kight
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Publication number: 20030158447Abstract: Process for preparing alkylaryl hydroperoxide containing product, which process comprises:Type: ApplicationFiled: February 6, 2003Publication date: August 21, 2003Inventors: Antoon Paul Michael Kremers, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
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Patent number: 6486360Abstract: The invention relates to a method for oxidizing organic substrate by using 1O2. According to the inventive method, organic substrates that react with 1O2 are mixed with 30-70% H2O2 in water, in an organic solvent or in a mixture thereof in the presence of a lanthanide as the catalyst. H2O2 is catalytically decomposed to water and 1O2 and is then oxidized to the corresponding oxidation products.Type: GrantFiled: September 28, 2001Date of Patent: November 26, 2002Assignee: DSM Fine Chemicals Austria NFG GmbH & CO KGInventors: Jean-Marie Aubry, Veronique Rataj-Nardello, Paul Alsters
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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: 6465695Abstract: A method for manufacturing cumene hydroperoxide comprises reacting cumene and oxygen in the presence of a water phase comprising aqueous ammonia, and in the absence of an additive comprising an alkali or alkaline earth metal, to form cumene hydroperoxide. A system for producing cumene hydroperoxide comprises a cumene feed in fluid communication with a reactor having a cumene hydroperoxide oxidate outlet; an oxygen feed in fluid communication with the reactor; and an ammonia feed in fluid communication with the cumene feed and/or the reactor, wherein the cumene feed, the oxygen feed, the ammonia feed, and the reactor are free of an additive comprising an alkali or alkaline earth metal.Type: GrantFiled: July 27, 2001Date of Patent: October 15, 2002Assignee: General Electric CompanyInventors: John William Fulmer, Eugene Edward Scott, William Dale Kight
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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: 6369278Abstract: There are provided: (I) a process for preparing an extract containing at least one hydroperoxide, which comprises the steps of: (1) oxidizing an aromatic hydrocarbon substituted with an alkyl group to obtain a liquid reaction mixture, and (2) extracting at least one hydroperoxide in the liquid reaction mixture to obtain an extract having a concentration of acetone of not more than 1% by weight: and (II) a process for preparing an extract containing at least one hydroperoxide, which comprises the steps of, (1) oxidizing an aromatic hydrocarbon substituted with an alkyl group to obtain a liquid reaction mixture, and (2) extracting at least one hydroperoxide with an aqueous alkali solution having an A value of not more than 10 to obtain an extract.Type: GrantFiled: December 7, 2000Date of Patent: April 9, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Tomoyuki Noritake, Shigeru Goto, Kenji Itoh
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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: 6023001Abstract: Peroxides are prepared from organic compounds and oxygen in a reaction vessel by introducing organic compound and oxygen to the reaction vessel and by simultaneously withdrawing a first liquid product stream from adjacent the top of the reactor and a second liquid product stream from adjacent the bottom of the reaction vessel. Suitable organic compounds include, but are not limited to, alkanes and all aryl compounds.Type: GrantFiled: March 18, 1998Date of Patent: February 8, 2000Assignee: Huntsman ICI Chemicals LLCInventors: William K. Culbreth, III, Mark E. Taylor, Kyle L. Preston, Mark A. Mueller
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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: 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: 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: 5453548Abstract: A process for the separation of ditertiary butyl peroxide form tertiary butanol is provided which includes the step of dehydrating the tertiary butanol to isobutylene and water.Type: GrantFiled: October 25, 1994Date of Patent: September 26, 1995Assignee: ARCO Chemical Technology, L.P.Inventors: Robert Nedwick, Jeffrey M. McFarland, Leonard A. Fabiano
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Patent number: 5436375Abstract: Tertiary butyl hydroperoxide and tertiary butyl alcohol are prepared from isobutane and oxygen in a vertical reactor by sparging a mixture of isobutane with oxygen to the bottom of the reactor, by charging a reaction mixture recycle stream to the reactor above the sparge point, by centrally charging a downwardly flowing stream of cooled fresh isobutane to the top of the reactor to induce central downflow of the fresh isobutane annular and upflow of the sparged mixture and the recycle stream, by withdrawing a liquid product stream adjacent the top of the reactor, by withdrawing a vapor product stream from the top of the reactor, by condensing entrained liquids in the vapor product, by recycling the condensed liquids and by recovering the liquid product stream.Type: GrantFiled: August 26, 1994Date of Patent: July 25, 1995Assignee: Texaco Chemical Inc.Inventors: Karen A. Thomas, Kyle L. Preston
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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: 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: 5243084Abstract: The present invention relates to a process for the oxidation of isobutane in the liquid phase to produce TBA and TBHP wherein at least a portion of the oxidation product mixture is obtained as distillate from fractional distillation of vapors from the oxidation zone.Type: GrantFiled: December 17, 1992Date of Patent: September 7, 1993Assignee: ARCO Chemical Technology, L.P.Inventors: Robert N. Cochran, Shaw-Chan Lin