Preparing By Oxidation Patents (Class 568/800)
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Patent number: 11319559Abstract: The invention relates to a process for the preparation of a sugar and/or fermentation product from lignocellulosic material.Type: GrantFiled: October 8, 2018Date of Patent: May 3, 2022Assignee: DSM IP ASSETS B.V.Inventors: Johannes Augustinus Kroon, Pierre Louis Woestenborghs
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Publication number: 20150141708Abstract: A process for purifying at least one product from coal tar is described. The process involves separating a coal tar fraction having a boiling point in the range of about 180° C. to about 230° C. into an acidic portion and a non-acidic portion by contacting the fraction with a caustic compound. The acidic portion is separated into a cresol portion and a xylenol portion, and the non-acidic portion is separated into a naphthalene portion and a naphthalene co-boiler portion. The acidic portion and the non-acidic portions are separated by contacting with an adsorbent comprising small, discrete crystallites, the adsorbent having less than 10 wt % amorphous binder component. The various portions can be separated in a similar manner.Type: ApplicationFiled: August 28, 2014Publication date: May 21, 2015
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Publication number: 20150141700Abstract: A process for producing alkylated aromatic compounds includes pyrolyzing a coal feed to produce a coke stream and a coal tar stream. The coal tar stream is hydrotreated and the resulting hydrotreated coal tar stream is cracked. A portion of the cracked coal tar stream is separated to obtain a fraction having an initial boiling point in the range of about 60° C. to about 180° C., and an aromatics-rich hydrocarbon stream is extracted by contacting the fraction with one or more solvents. The aromatics-rich hydrocarbon stream is contacted with an alkylating agent to produce an alkylated aromatic stream, or the aromatics-rich hydrocarbon stream is reacted with an aliphatic compound or methanol in the presence of a catalyst to produce a methylated aromatic stream. The alkylated aromatic stream, the methylated aromatic stream, or both are separated into at least a benzene stream, a toluene stream, and a xylenes stream.Type: ApplicationFiled: August 22, 2014Publication date: May 21, 2015Inventors: James A. Johnson, Paul T. Barger, Maureen L. Bricker, John Q. Chen, Peter K. Coughlin, Stanley J. Frey, Joseph A. Kocal, Matthew Lippmann, Vasant P. Thakkar
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Patent number: 9029612Abstract: In a process for producing phenol, cyclohexylbenzene is contacted with oxygen in the presence of an oxidation catalyst comprising a cyclic imide under oxidation conditions effective to produce a product comprising cyclohexylbenzene hydroperoxide and unreacted cyclic imide catalyst. At least a portion of the product is contacted with a cleavage catalyst under conditions effective to convert at least a portion of the cyclohexylbenzene hydroperoxide into a second product comprising further unreacted cyclic imide catalyst, phenol, and cyclohexanone. A portion of the further unreacted cyclic imide catalyst may then be removed from the second product and optionally recycled back to the oxidation step.Type: GrantFiled: December 15, 2011Date of Patent: May 12, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Kun Wang, Jihad M. Dakka
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Publication number: 20150038688Abstract: A method of decomposing an organic substrate includes identifying an organic substrate or its constituents having one or more desired or undesired properties; and contacting the organic substrate with an oxidizing agent and a catalyst selected from the group consisting of sterically hindered and electronically activated metallotetraphenylporphyrins, metallophthalocyanines and metallosalen complexes in an aqueous or aqueous-organic solution to produce a treated composition comprising one or more degradation products, wherein the degradation products have one or more desired properties and/or lack the undesired properties of the organic substrate.Type: ApplicationFiled: August 15, 2014Publication date: February 5, 2015Inventor: Mukund CHORGHADE
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Publication number: 20140296581Abstract: In a process for producing phenol, cyclohexylbenzene is contacted with oxygen in the presence of an oxidation catalyst comprising a cyclic imide under oxidation conditions effective to produce a product comprising cyclohexylbenzene hydroperoxide and unreacted cyclic imide catalyst. At least a portion of the product is contacted with a cleavage catalyst under conditions effective to convert at least a portion of the cyclohexylbenzene hydroperoxide into a second product comprising further unreacted cyclic imide catalyst, phenol, and cyclohexanone. A portion of the further unreacted cyclic imide catalyst may then be removed from the second product and optionally recycled back to the oxidation step.Type: ApplicationFiled: December 15, 2011Publication date: October 2, 2014Applicant: ExxonMobil Chemical Patents Inc.Inventors: Kun Wang, Jihad M. Dakka
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Patent number: 8704012Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using a low energy process and an entrainer. The crude ethanol product is separated in an distillation column to produce a distillate stream comprising the entrainer. The ethanol product is recovered from the residue stream.Type: GrantFiled: June 16, 2011Date of Patent: April 22, 2014Assignee: Celanese International CorporationInventors: David Lee, Lincoln Sarager, Trinity Horton, Victor J. Johnston
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Patent number: 8563461Abstract: A process to activate a titanium silicalite catalyst for the oxidation of benzene to phenol is provided. The catalyst is activated in the reactor for the oxidation by feeding to a reactor containing the titanium silicalite catalyst, during a time of from 2 to 6 hours, at a temperature ranging from 20 to 120° C., an aqueous solution of ammonium acid fluoride in a concentration ranging from 0.1% to 1% by weight; and hydrogen peroxide in a concentration ranging from 3% to 10% by weight; feeding water to the reactor at the end of the reaction; and drying or calcining the catalyst contained in the reactor to obtain the activated catalyst. The catalyst is represented by the formula: xTiO2.(1?x)SiO2 wherein x is from 0.0001 to 0.04.Type: GrantFiled: March 17, 2010Date of Patent: October 22, 2013Assignee: Polimeri Europa S.p.A.Inventors: Daniele Bianchi, Rossella Bortolo, Chiara Busto, Carla Lazzari
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Patent number: 8501999Abstract: The process provided herein is concerned with recovery of hydrocarbons from sulfones using an individual alkali and alkaline-earthy base and a mixture of thereof. As the starting materials are sulfones generated by ODS and commercially inexpensive alkali and alkaline-earth bases, the cost and ecological impact of solid waste disposal is minimized.Type: GrantFiled: November 4, 2010Date of Patent: August 6, 2013Assignees: Saudi Arabian Oil Company, The Chancellor, Masters and Scholars of the University of OxfordInventors: Farhan M. Al-Shahrani, Tiancun Xiao, Huahong Shi, Malcolm L. H. Green
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Publication number: 20120277472Abstract: The present invention relates to a hydrogenation process that may be used in connection with the production of phenol. In the process, a composition comprising: (i) cyclohexylbenzene; and (ii) a hydrogenable component are contacted with hydrogen in the presence of a hydrogenation catalyst under hydrogenation conditions. The hydrogenable component can be one or more of an olefin, a ketone or phenol. The hydrogenation catalyst has hydrogenation component and a support.Type: ApplicationFiled: November 23, 2010Publication date: November 1, 2012Inventors: Jihad M. Dakka, Keith H. Kuechler, James R. Lattner, Edmund J. Mozeleski
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Patent number: 8247622Abstract: A process is described for the preparation of phenol by the hydrodeoxygenation of polyhydroxylated benzene derivatives or by the selective hydroxylation of benzene under depletive conditions, characterized in that the above-mentioned reactions are carried out in the presence of a catalyst based on multi component metal oxides comprising at least one metal selected from the groups VB, VIB, VIII, IB, IIB, IVA, VA.Type: GrantFiled: October 20, 2010Date of Patent: August 21, 2012Assignee: Polimeri Europa S.p.A.Inventors: Leonardo Dalloro, Alberto Cesana, Roberto Buzzoni, Fausto Genoni, Guido Spano, Franco Rivetti
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Publication number: 20120088937Abstract: One exemplary embodiment can be a method for processing polyisopropylbenzene for producing cumene. The method can include passing a transalkylation feed stream to a transalkylation zone, and passing a reaction product to a separation zone. Typically, the separation zone produces a stream including di-isopropylbenzene, tri-isopropylbenzene, and one or more heavy compounds. Moreover, the stream may include at least about 0.7%, by weight, of the one or more heavy compounds based on the weight of the di-isopropylbenzene, tri-isopropylbenzene, and the one or more heavy compounds in the stream, and at least a portion of the stream is recycled to the transalkylation zone.Type: ApplicationFiled: October 12, 2010Publication date: April 12, 2012Applicant: UOP, LLCInventors: Deng-Yang Jan, Christopher Lepine Standing, James Albert Johnson, Margo W. Steward, Mathias P. Koljack
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Patent number: 8115029Abstract: Oxidations of hydrocarbons, cycloalkanes and alkenes, arylalkanes, and a variety of other organic substrates are accomplished by cobalt-N-hydroxysuccinimide co-catalyzed reactions with dioxygen under unusually mild, near ambient conditions of temperature and pressure. The improved safety of the oxidation method and the high yields of product obtained make use of a unique combination of cobalt (II) complexes with N-hydroxysuccinimide. These autoxidation reactions do not have prolonged initiation times. Many of these reactions can be safely performed under normal chemical laboratory conditions and do not require specialized equipment or reagents.Type: GrantFiled: November 2, 2007Date of Patent: February 14, 2012Assignee: University of KansasInventors: Richard S. Givens, Chi Cheng Ma, Daryle H. Busch, Bala Subramaniam, Bhuma Rajagopalan
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Publication number: 20120016127Abstract: The invention at hand describes Cu-(II)-oxygen adduct complexes, which are stable at room temperature, as well as methods for their production. In this, compounds of the general formula [L-Cu—O—O—Cu-L](BAr4)2 are concerned. Here, BAr4? is a tetraarylborate anion, selected from tetraphenylborate and tetrakis(3,5-trifluoromethyl)phenylborate. L represents a tripodal tetradentate ligand, wherein, each of the four binding sites of the tripodal tetradentate ligand is a nitrogen atom. Each of the three podal ligands is suitable for comprising an aliphatic amine or a nitrogen-containing heteroaromatic compound independently of one another. A bridge of one to four carbon atoms is located between the central nitrogen atom and the nitrogen atom of each of the podal ligands. The Cu-(II)-oxygen adduct complexes according to the present invention are produced, by initially reacting the ligand L with a Cu-(I) salt to [Cu-L]X.Type: ApplicationFiled: October 27, 2008Publication date: January 19, 2012Inventors: Siegfried Schindler, Christian Würtele
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Publication number: 20110184204Abstract: This invention discloses methods and processes for selectively converting hydrocarbons such as methane to materials such as alcohols or other materials containing more reactive functionalities.Type: ApplicationFiled: February 7, 2011Publication date: July 28, 2011Inventors: ROY A. PERIANA, William A. Goddard, III
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Publication number: 20110184191Abstract: Two zone (11, 12; 21, 22; 31, 32; 41, 42) fluidized bed reactor (10, 20, 30, 40), wherein the upper zone (11, 21, 31, 41) presents a different section than the lower zone (12, 22, 32, 42). In one of the two zones (11, 12; 21, 22; 31, 32; 41, 42), a zone of reducing atmosphere is created and, in the other zone, a zone of oxidising atmosphere is created. In a preferred embodiment, the section of the upper zone (11, 21, 31, 41) is larger than that of the lower zone (12, 22, 32, 42), creating a reducing atmosphere in the upper zone (11, 21, 31, 41) and an oxidising atmosphere in the lower zone (12, 22, 32, 42). Rows of flow distributor tubes exist in the upper zone (11, 21, 31, 41) to avoid the appearance of dead zones.Type: ApplicationFiled: June 19, 2009Publication date: July 28, 2011Applicant: UNIVERSIDAD DE ZARAGOZAInventors: Miguel Menéndez Sastre, Javier Herguido Huerta, Carlos Téllez Ariso, Jaime Soler Herrero, Maria Pilar Gimeno Tolosa
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Publication number: 20110178342Abstract: A process is described for producing cumene comprising contacting a feed stream comprising benzene and a further feed stream comprising isopropanol or a mixture of isopropanol and propylene in the presence of an alkylation catalyst comprising at least a molecular sieve of the MCM-22 family in an alkylation zone under alkylation conditions of at least partial liquid phase and with a water concentration in the liquid phase of at least 50 ppm to react at least part of said isopropanol and benzene to produce an effluent stream containing cumene.Type: ApplicationFiled: September 23, 2009Publication date: July 21, 2011Applicant: BADGER LICENSING LLCInventors: Shyh-Yuan Henry Hwang, Dana E. Johnson, Joseph C. Peters, Chung-Ming Chi, Kevin J. Fallon, Francis A. Demers
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Publication number: 20110092746Abstract: A process is described for the preparation of phenol by the hydrodeoxygenation of polyhydroxylated benzene derivatives or by the selective hydroxylation of benzene under depletive conditions, characterized in that the above-mentioned reactions are carried out in the presence of a catalyst based on multi component metal oxides comprising at least one metal selected from the groups VB, VIB, VIII, IB, IIB, IVA, VA.Type: ApplicationFiled: October 20, 2010Publication date: April 21, 2011Applicant: POLIMERI EUROPA S.p.A.Inventors: Leonardo DALLORO, Alberto Cesana, Roberto Buzzoni, Fausto Genoni, Guido Spano, Franco Rivetti
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Publication number: 20100234550Abstract: In this disclosure, a system is described, comprising a shear device with at least one inlet and at least one outlet and a mixing vessel with at least one inlet and at least one outlet, wherein an inlet of the shear device is in fluid communication with an outlet of the mixing vessel. In certain embodiments, the shear device and the mixing vessel form a loop for fluid communication. Also disclosed herein is a method of high shear oxidation, comprising mixing an oxidant with a substrate to form a substrate-oxidant mixture and applying shear to the substrate-oxidant mixture to form a product. The product includes ethylene oxide, propylene oxide, terephthalic acid, phenol, acrylonitrile, maleic anhydride, phthalic anhydride, nitric acid, caprolactam, oxidized polyethylene, oxidized polypropylene, oxidized polyethylene copolymers, and oxidized polypropylene copolymers. Suitable oxidant includes air, oxygen, ozone, peroxide, organic peroxide, halogen, oxygen-containing gas, and halogen-containing gas.Type: ApplicationFiled: December 14, 2009Publication date: September 16, 2010Applicant: H R D CORPORATIONInventors: Abbas Hassan, Harshad M. Bhatt, Aziz Hassan, Gregory G. Borsinger
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Patent number: 7759529Abstract: The invention relates to a continuous process for the preparation of phenol by means of the direct oxidation of benzene with hydrogen peroxide in the presence of a catalyst based on titanium silicalite TS-1 comprising: (a) running the process in a fixed bed reactor containing the catalyst based on TS-1 at a temperature ranging from 80-120° C. and at a pressure ranging from 3-15 atm; (b) feeding to the reactor a stream containing H2O2, benzene, sulfolane and water in a single or double phase, wherein the quantities of the single components are within the range of 0.2-6, 15-60, 30-80, 0.5-30 parts by weight, respectively, for every 100 units fed and whose total flow rate is calculated so that the residence time in the reactor (defined as the ratio between the quantity of catalyst by weight and the feeding flow rate) ranges from 0.3 to 2 min; (c) recovery of the products, by-products and solvent from the liquid stream leaving the reactor.Type: GrantFiled: October 26, 2005Date of Patent: July 20, 2010Assignee: Polimeri Europa S.p.A.Inventors: Daniele Bianchi, Rossella Bortolo, Chiara Busto, Carla Lazzari
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Patent number: 7586014Abstract: The present invention provides an improved process for the liquid phase selective hydroxylation of benzene. The process provides a direct single step selective liquid phase hydroxylation of benzene to phenol using environment friendly green oxidant, hydrogen peroxide, and vanadyl pyrophosphate as the catalyst under mild reaction conditions. The process provides benzene conversion of 30-70% and selectivity for phenol of up to 100%.Type: GrantFiled: March 11, 2008Date of Patent: September 8, 2009Assignee: Council of Scientific and Industrial ResearchInventors: Datta Arunabha, S. Sakthivel, Satyarthi Jitendra Kumar
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Patent number: 7544845Abstract: The present invention relates to a continuous method for treating a crude phenol stream comprising methylbenzofuran and hydroxyacetone by passing the crude phenol stream through at least two reactors connected in series the reactors containing an acidic ion exchange resin, whereby the temperature in successive reactors decreases in flow direction of the phenol stream so that the temperature in the first reactor in flow direction of the phenol stream is between 100° C. and 200° C. and the temperature in the last reactor in flow direction of the phenol stream is between 50° C. and 90° C. without a thermal separation step between any of two successive reactors and to the use of this method in a process for making phenol.Type: GrantFiled: April 17, 2007Date of Patent: June 9, 2009Assignee: Ineos Phenol GmbH & Co. KGInventors: Gunther Lohmer, Otto Schnurr, Manfred Weber, Markus Weber
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Publication number: 20090005608Abstract: Use of a high shear mechanical device incorporated into a process for the production of cyclohexanol is capable of decreasing mass transfer limitations, thereby enhancing the cyclohexanol production process. A system for the production of cyclohexanol from air oxidation of cyclohexane, the system comprising a high shear device, the outlet of the high shear device fluidly connected to the inlet of a reactor; the high shear device capable of providing a dispersion of air bubbles within a liquid comprising cyclohexane, the bubbles having an average bubble diameter of less than about 100 ?m.Type: ApplicationFiled: June 12, 2008Publication date: January 1, 2009Applicant: H R D CORPORATIONInventors: Abbas HASSAN, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20080221369Abstract: A substituted phenolic compound is prepared by oxidizing a substituted diarylethane compound with oxygen in the presence of a nitrogen-containing cyclic compound, and treating the oxidized product with an acid. The nitrogen-containing cyclic compound includes, as a constituent of its ring, a skeleton represented by following Formula (I): wherein X is oxygen atom or an —OR group, where R is hydrogen atom or a hydroxyl-protecting group. The substituted diarylethane compound is represented by following Formula (1): wherein each of Ring Ar1 and Ring Ar2 is independently a monocyclic or polycyclic aromatic carbocyclic ring; Y1 is an electron-donating group; Y2 is an electron-withdrawing group; “p” is an integer of 1 or more; and “q” is an integer of 0 or more. The substituted phenolic compound is represented by following Formula (2): wherein Ring Ar1, Y1, and “p” are as defined above.Type: ApplicationFiled: February 14, 2008Publication date: September 11, 2008Applicant: DAICEL CHEMICAL INSDUSTRIES, LTD.Inventors: Yasutaka Ishii, Takahiro Iwahama
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Patent number: 6936740Abstract: Phenol is formed by reaction of oxidant and benzene over a solid catalyst such as Pd on TS-1, the reaction being carried out in carbon dioxide solvent at conditions effective to provide a dense phase reaction mixture.Type: GrantFiled: August 19, 2004Date of Patent: August 30, 2005Assignee: ARCO Chemical Technology, L.P.Inventors: Robert N. Cochran, Jay F. Miller, Eric John Beckman, Sarah Emma Jones
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Patent number: 6900358Abstract: A process for hydroxylating benzene under catalytic distillation conditions to produce hydroxylated products such as phenol is provided. The process provides for direct hydroxylation of liquid phase benzene with an oxidant and a zeolite catalyst under conditions effective to prevent coke formation on the catalyst.Type: GrantFiled: April 24, 2001Date of Patent: May 31, 2005Assignee: Shell Oil CompanyInventor: David Morris Hamilton, Jr.
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Patent number: 6828466Abstract: A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.Type: GrantFiled: July 15, 2003Date of Patent: December 7, 2004Assignee: Board of Trustees of Michigan State UniversityInventors: Robert E. Maleczka, Jr., Milton R. Smith, III, Daniel Holmes, Feng Shi
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Publication number: 20040236155Abstract: The invention relates to a technique for preparing aromatic organozinc compounds and to a composition therefore. This composition constitutes a reactant that can be used to carry out the synthesis of organozinc compounds, and comprises a cobalt salt, a zinc salt, a polar aprotic solvent and elemental zinc in divided form, the elemental zinc being in solid form, the other elements being in a form dissolved in the solvent. Application to organic synthesis.Type: ApplicationFiled: June 18, 2004Publication date: November 25, 2004Inventors: Jacques Perichon, Corinne Gosmini, Hyacinthe Fillon
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Publication number: 20040122264Abstract: The invention relates to a process for the preparation of phenol comprising the following phases:Type: ApplicationFiled: November 20, 2003Publication date: June 24, 2004Applicant: POLIMERI EUROPA S.p.A.Inventors: Daniele Bianchi, Rossella Bortolo, Roberto Buzzoni, Alberto Cesana, Leonardo Dalloro, Rino D'Aloisio
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Patent number: 6740785Abstract: Improved oxidation methods are provided wherein a reaction mixture comprising a substrate to be oxidized (e.g., phenols, alkenes) and an oxidation catalyst (typically dispersed in an organic solvent system) is supplemented with a compressed gas which expands the reaction mixture, thus accelerating the oxidation reaction. In preferred practice pressurized subcritical or supercritical carbon dioxide is used as the expanding gas, which is introduced into the reaction mixture together with an oxidizing agent. The inventive methods improve the substrate conversion and product selectivity by increasing the solubility of the oxidizing agent in the reaction mixture.Type: GrantFiled: July 26, 2002Date of Patent: May 25, 2004Assignee: The University of KansasInventors: Bala Subramaniam, Daryle H. Busch, Ghezai T. Musie, Ming Wei
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Publication number: 20040030197Abstract: A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.Type: ApplicationFiled: July 15, 2003Publication date: February 12, 2004Applicant: Board of Trustees of Michigan State UniversityInventors: Robert E. Maleczka, Milton R. Smith, Daniel Holmes, Feng Shi
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Publication number: 20030120121Abstract: A reactant selected from the group consisting of alkanes, alkenes, and aromatics is reacted with a metal halide to form the halide of the reactant and reduced metal. The reduced metal is oxidized to form metal oxide. The metal oxide is reacted with the halide of the reactant to produce the alcohol and/or the ether corresponding to the reactant and the original metal halide which is recycled.Type: ApplicationFiled: February 12, 2003Publication date: June 26, 2003Applicant: GRT, Inc.Inventors: Jeffrey H. Sherman, Eric McFarland
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Patent number: 6573413Abstract: A method for catalytic production of hydroxylated aromatics by exposing zeolite catalyst to a reducing atmosphere to activate said catalyst, and reacting an aromatic with nitrous oxide in the presence of said activated catalyst.Type: GrantFiled: April 18, 2001Date of Patent: June 3, 2003Assignee: Solutia Inc.Inventors: Valery S. Chernyavsky, Alexander Sergeevich Kharitonov, Gennady I. Panov, Konstantin A. Dubkov
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Publication number: 20030069452Abstract: A reactant selected from the group consisting of alkanes, alkenes, and aromatics is reacted with a metal halide to form the halide of the reactant and reduced metal. The reduced metal is oxidized to form metal oxide. The metal oxide is reacted with the halide of the reactant to produce the alcohol and/or the ether corresponding to the reactant and the original metal halide which is recycled.Type: ApplicationFiled: November 19, 2002Publication date: April 10, 2003Inventors: Jeffrey H. Sherman, Eric McFarland
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Patent number: 6531615Abstract: This invention relates to a composition comprising antimony trifluoride and silica, a method for the preparation of said composition and use of said composition as a catalyst in a process for the oxidation of cyclohexanone to &egr;-caprolactone.Type: GrantFiled: January 30, 2001Date of Patent: March 11, 2003Assignee: Solvay (Societe Anonyme)Inventors: Michael C. Rocca, Graham Carr, Arnold B. Lambert, Duncan J. MacQuarrie, James H. Clark
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Publication number: 20030040646Abstract: The present invention relates to industrial applications of nitrous oxide, e.g. the hydroxylation of benzene to phenol, requires large quantities of nitrous oxide having a very low impurity content. According to the present invention, nitrous oxide which is obtained by reaction of ammonia with nitric acid can be used for the hydroxylation of aromatics, the use of nitrous oxide from the reaction of ammonia with nitric acid in particular being economically advantageous because all starting materials are available in sufficient quantity and at a favorable price.Type: ApplicationFiled: July 5, 2002Publication date: February 27, 2003Inventors: Uwe Tanger, Johan Van Den Tillaart
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Patent number: 6476277Abstract: The present invention relates to a process for preparing hydroxyaromatics by oxidizing aromatics with dinitrogen monoxide in the gas phase in the presence of nanocrystalline zeolites.Type: GrantFiled: July 24, 2001Date of Patent: November 5, 2002Assignee: Bayer AktiengesellschafterInventors: Bernd Vogel, Elias Klemm, Mathias Seitz, Jochen Heller, Jörg Reiser
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Patent number: 6448454Abstract: Improved oxidation methods are provided wherein a reaction mixture comprising a substrate to be oxidized (e.g., phenols, alkenes) and an oxidation catalyst (typically dispersed in an organic solvent system) is supplemented with a compressed gas which expands the reaction mixture, thus accelerating the oxidation reaction. In preferred practice pressurized subcritical or supercritical carbon dioxide is used as the expanding gas, which is introduced into the reaction mixture together with an oxidizing agent. The inventive methods improve the substrate conversion and product selectivity by increasing the solubility of the oxidizing agent in the reaction mixture.Type: GrantFiled: April 7, 2000Date of Patent: September 10, 2002Assignee: The University of KansasInventors: Bala Subramaniam, Daryle H. Busch, Ghezai T. Musie, Ming Wei
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Patent number: 6437197Abstract: A process for increasing catalyst stability during the direct hydroxylation of liquid phase benzene or benzene derivatives with an oxidant and a solid catalyst under conditions effective to prevent coke formation on the catalyst. The process can be used to form phenol or phenol derivatives.Type: GrantFiled: April 27, 2000Date of Patent: August 20, 2002Assignee: Shell Oil CompanyInventor: David Morris Hamilton, Jr.
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Patent number: 6414197Abstract: A method and a catalyst are described for selective oxidation of aromatic compounds (e.g., benzene and its derivatives) into hydroxylated aromatic compounds (e.g., corresponding phenols). For example, benzene can be converted into phenol with a yield of at least 30-40%, and a selectivity on the basis of benzene of at least 95-97%. The selectivity for this reaction based on N2O is at least 90-95%. Therefore, no substantial N2O decomposition or consumption for complete benzene oxidation to CO+CO2 or other side products occurs. Similar results are obtained with benzene derivatives (e.g., fluorobenzene, difluorobenzene, phenol), although the selectivity is somewhat lower in the case of derivatives (e.g., about 80-85% in the case of fluorosubstituted benzenes). A preferred catalyst for this process is a composition containing a high-silica pentasil-type zeolite (e.g, an HZSM-5 type zeolite) which contains no purposefully introduced additives such as transition or noble metals.Type: GrantFiled: May 13, 1998Date of Patent: July 2, 2002Assignee: General Electric CompanyInventors: Leonid Modestovich Kustov, Viktor Ignatyevich Bogdan, Vladimir Borisovich Kazansky
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Patent number: 6388145Abstract: The invention relates to the field of organic synthesis, more specifically to a method for the production of phenol and cresol by the direct selective oxidation of benzene and toluene with nitrous oxide in the presence of a heterogeneous catalyst. Commercial high-silica zeolites are first calcined at a temperature of 500-950° C. sufficient to dehydroxylate it. It is then modified by the addition of modifying agents—zinc ions or zinc oxide—by applying a zinc compound to it. The catalyst is then activated in air or an inert gas at 300-850° C. The mixture of benzene or toluene with the nitrous oxide is brought into contact with the modified catalyst at 225 to 500° C.Type: GrantFiled: March 23, 2000Date of Patent: May 14, 2002Assignee: General Electric CompanyInventors: Leonid Modestovich Kustov, Andrei Leonidovich Tarasov, Aleksandr Arunovich Tyrlov, Viktor Ignatyevich Bogdan
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Publication number: 20020042544Abstract: The invention relates to the field of organic synthesis, more specifically to a method for the production of phenol and cresol by the direct selective oxidation of benzene and toluene with nitrous oxide in the presence of a heterogeneous catalyst. Commercial high-silica zeolites are first calcined at a temperature of 500-950° C. sufficient to dehydroxylate it. It is then modified by the addition of modifying agents—zinc ions or zinc oxide—by applying a zinc compound to it. The catalyst is then activated in air or an inert gas at 300-850° C. The mixture of benzene or toluene with the nitrous oxide is brought into contact with the modified catalyst at 225 to 500° C.Type: ApplicationFiled: March 23, 2000Publication date: April 11, 2002Inventors: Leonid Modestovich Kustov, Andrei Leonidovich Tarasov, Aleksandr Arunovich Tyrlov, Viktor Ignatyevich Bogdan
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Publication number: 20020040168Abstract: A method and a catalyst are described for selective oxidation of aromatic compounds (e.g., benzene and its derivatives) into hydroxylated aromatic compounds (e.g., corresponding phenols). For example, benzene can be converted into phenol with a yield of at least 30-40%, and a selectivity on the basis of benzene of at least 95-97%. The selectivity for this reaction based on N2O is at least 90-95%. Therefore, no substantial N2O decomposition or consumption for complete benzene oxidation to CO+CO2 or other side products occurs. Similar results are obtained with benzene derivatives (e.g., fluorobenzene, difluorobenzene, phenol), although the selectivity is somewhat lower in the case of derivatives (e.g., about 80-85% in the case of fluorosubstituted benzenes). A preferred catalyst for this process is a composition containing a high-silica pentasil-type zeolite (e.g, an HZSM-5 type zeolite) which contains no purposefully introduced additives such as transition or noble metals.Type: ApplicationFiled: May 13, 1998Publication date: April 4, 2002Inventors: LEONID MODESTOVICH KUSTOV, VIKTOR IGNATYEVICH BOGDAN, VLADIMIR BORISOVICH KAZANSKY
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Publication number: 20020026085Abstract: A method for catalytic production of hydroxylated aromatics by exposing zeolite catalyst to a reducing atmosphere to activate said catalyst, and reacting an aromatic with nitrous oxide in the presence of said activated catalyst.Type: ApplicationFiled: April 18, 2001Publication date: February 28, 2002Inventors: Valery S. Chernyavsky, Alexander Sergeevich Kharitonov, Gennady I. Panov, Konstantin a. Dubkov
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Publication number: 20020016514Abstract: There are disclosed a process for producing a dihydric phenol which comprises oxidizing a monohydric phenol by a peroxide compound in the presence of a &bgr;-zeolite, a ketone and a phosphoric acid, and a process for producing a dihydric phenol which comprises oxidizing a monohydric phenol in the presence of a &bgr;-zeolite, a ketone and a phosphoric acid, by feeding a monohydric phenol, hydrogen peroxide, a ketone and a phosphoric acid into a reactor in which a &bgr;-zeolite is charged, to oxidize the monohydric phenol into a dihydric phenol, and delivering the resultant reaction mixture from the reactor.Type: ApplicationFiled: June 19, 2001Publication date: February 7, 2002Applicant: UBE Industries, LtdInventors: Takashi Atoguchi, Shigeru Yao, Tomonori Kanougi
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Patent number: 6255539Abstract: Inert gas additive is utilized in the catalytic oxidation of benzene with nitrous oxide to produce phenol in order to prevent excessive exothermic temperature increases and to render gaseous mixtures throughout the process non-flammable.Type: GrantFiled: October 2, 1997Date of Patent: July 3, 2001Assignee: Solutia Inc.Inventors: Anthony K. Uriarte, Christopher R. Buechler, Jerry R. Ebner, Michael J. Gross, William D. McGhee, Jayne E. Morris, Erik D. Sall
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Patent number: 6180835Abstract: A cyclopropylacetylene derivative of the formula (V): is prepared by reacting a propynol derivative of the formula (I): with a propane derivative of the formula (VI): in the presence of a base in an amount of 2 or more equivalents relative to the propynol derivative to give a cyclopropane derivative of the formula (III): deprotecting the protecting group for the hydroxyl group of the cyclopropane derivative to give a cyclopropylpropynol derivative of the formula (IV): and subjecting the cyclopropylpropynol derivative to retro-ethynylation. In the above formulas R1, R2, R3, R4 and R5 represent hydrogen; or an alkyl, alkenyl, aryl or aralkyl group, each of which may have a substituent, R6 and R7 is hydrogen; or an alkyl, alkenyl, aryl or aralkyl group, each of which may have a substituent, or R6 and R7 taken together form a ring, R8 is a protecting group for the hydroxyl group and X and Y are each a leaving group.Type: GrantFiled: February 5, 1999Date of Patent: January 30, 2001Assignee: Kuraray Co., Ltd.Inventors: Goro Asanuma, Kazuya Takaki, Shigeo Ohzono, Manzo Shiono
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Patent number: 6166268Abstract: The invention relates to a process for preparing hydroxyl-containing aromatic compounds by catalytic oxidation.Type: GrantFiled: April 29, 1999Date of Patent: December 26, 2000Assignee: Creavis Gesellschaft fuer Technologie und Innovation mbHInventors: Adolf Kuehnle, Mark Duda
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Patent number: 6156938Abstract: A process for hydroxylating an aromatic compound comprises the steps of: (a) contacting an aromatic compound with a catalyst having an average concentration of .alpha.-sites of at least about 1.multidot.10.sup.16 per gram of catalyst, the catalyst having .alpha.-oxygen loaded thereon, whereby an hydroxylated derivative of the aromatic compound is produced; and (b) regenerating the catalyst when the concentration of .alpha.-sites falls below a predetermined value. The predetermined value will depend on the process design, but can suitably be about 1.multidot.10.sup.16 per gram of catalyst or higher.Another embodiment of the process comprises: (a) contacting an aromatic compound with a catalyst having an average concentration of .alpha.-sites of at least about 1.multidot.10.sup.16 per gram of catalyst, the catalyst having .alpha.-oxygen loaded thereon, whereby an hydroxylated derivative of the aromatic compound is produced; and (b) reloading the catalyst with .alpha.Type: GrantFiled: March 31, 1998Date of Patent: December 5, 2000Assignee: Solutia, Inc.Inventors: Vladimir I. Sobolev, Mikhail A. Rodkin, Anthony K. Uriarte, Gennady I. Panov
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Patent number: 6133487Abstract: An improved process is described for the synthesis of hydroxylated aromatic compounds by means of the oxidation of an aromatic substrate with hydrogen, peroxide in an organic solvent, in the presence of synthetic zeolites, wherein the improvement consists in the fact that the organic solvent is selected from compounds having general formula (I) ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3 and R.sub.4, the same or different, represent a hydrogen atom or an alkyl group with from 1 to 4 carbon atoms or from compounds having general formula (II) ##STR2## wherein R and R', the same or different, represent an alkyl radical with from 1 to 4 carbon atoms.Type: GrantFiled: October 22, 1998Date of Patent: October 17, 2000Assignee: Enichem S.p.A.Inventors: Raffaele Ungarelli, Luigi Balducci, Daniele Bianchi