Preparing By Cleavage Of Hydroperoxide Or Other Peroxide Patents (Class 568/798)
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Patent number: 7847128Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone. The benzene and hydrogen are then contacted in the at least one reaction zone under hydroalkylation conditions with a catalyst system comprising a molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom, and at least one hydrogenation metal to produce an effluent containing cyclohexylbenzene. The catalyst system has an acid-to-metal molar ratio of from about 75 to about 750.Type: GrantFiled: August 12, 2008Date of Patent: December 7, 2010Assignee: ExxonMobil Chemical Patents Inc.Inventors: Tan-Jen Chen, Jane C. Cheng, Terry E. Helton, John Scott Buchanan
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Patent number: 7834218Abstract: A process for producing phenol and methyl ethyl ketone comprises contacting benzene and a C4 alkylating agent under alkylation conditions and in the presence of an alkylation catalyst comprising at least one molecular sieve of the MCM-22 family to produce an alkylation effluent comprising secbutylbenzene; wherein the contacting is conducted in a plurality of reaction zones and the C4 alkylating agent secbutylbenzene fraction is recovered from the alkylation effluent and comprises at least 95 wt % sec-butylbenzene, less than 100 wt ppm of C8+ olefins, and less than 0.5 wt % of isobutylbenzene and tert-butylbenzene. The sec-butylbenzene fraction is then oxidized to produce sec-butylbenzene hydroperoxide and the hydroperoxide is cleaved to produce phenol and methyl ethyl ketene.Type: GrantFiled: February 8, 2007Date of Patent: November 16, 2010Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Jon E. Stanat, Francisco M. Benitez, John S. Buchanan, Jane C. Cheng, Jeffrey T. Elks
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Patent number: 7812196Abstract: A process for producing phenol and methyl ethyl ketone comprises contacting benzene and a C4 olefin under alkylation conditions and in the presence of an alkylation catalyst to produce an alkylation effluent comprising sec-butylbenzene and C8+ olefins. The alkylation effluent is then treated to reduce the amount of said C8+ olefins and produce a treated effluent, whereafter the sec-butylbenzene in the treated effluent is oxidized to produce a hydroperoxide and the hydroperoxide is cleaved to produce phenol and methyl ethyl ketone.Type: GrantFiled: February 8, 2007Date of Patent: October 12, 2010Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Edmund J. Mozeleski, Jane C. Cheng, Francisco M. Benitez, Jon E. Stanat, John S. Buchanan
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Patent number: 7799958Abstract: The present invention relates to a process for the production of iso-propanol by liquid phase hydrogenation of acetone to iso-propanol in at least two hydrogenation reaction stages, each reaction stage comprising a hydrogenation reaction zone, wherein the hydrogenation reaction product leaving the reaction zone of the first reaction stage contains unreacted acetone and a product stream comprising acetone and iso-propanol is transferred to the reaction zone of a subsequent reaction stage said product stream having at the inlet to the reaction zone of said subsequent reaction stage a temperature of 60 to 100° C., wherein the temperature of the product stream leaving the reaction zone of said subsequent reaction stage at the outlet from said reaction zone is at most 40° C. higher than the temperature of the product stream entering said reaction zone at the inlet to said reaction zone and the temperature in said subsequent reaction zone does not exceed 125° C.Type: GrantFiled: October 3, 2008Date of Patent: September 21, 2010Assignee: Barclays Bank PLCInventors: Ralf Bonmann, Werner Pompetzki, Markus Weber
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Patent number: 7799956Abstract: A process for producing phenol and methyl ethyl ketone comprises contacting benzene with a C4 alkylating agent under alkylation conditions with catalyst comprising zeolite beta or a molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom to produce an alkylation effluent comprising sec-butylbenzene. The sec-butylbenzene is then oxidized to produce a hydroperoxide and the hydroperoxide is decomposed to produce phenol and methyl ethyl ketone.Type: GrantFiled: August 5, 2005Date of Patent: September 21, 2010Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jane Chi-ya Cheng, John S. Buchanan, Doron Levin, Michael A. Steckel, Jihad M. Dakka, James P. Stokes, John L. Robbins, Jon E. Stanat, Charles M. Smith, José G. Santiesteban
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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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Publication number: 20100234637Abstract: An integrated process for producing aromatic hydrocarbons and ethylene and/or propylene and optionally other lower olefins from low molecular weight hydrocarbons, preferably methane, which comprises: (a) contacting one or more low molecular weight alkanes, preferably methane, with a halogen, preferably bromine, under process conditions sufficient to produce a monohaloalkane, preferably monobromomethane, (b) reacting a first portion of the monohaloalkane in the presence of a coupling catalyst under process conditions sufficient to produce aromatic hydrocarbons and C2-5 alkanes, (c) separating the aromatic hydrocarbons from the product mixture of step (b) to produce aromatic hydrocarbons, (d) reacting a second portion of the monohaloalkane in the presence of a coupling catalyst under process conditions sufficient to produce ethylene and/or propylene.Type: ApplicationFiled: March 15, 2010Publication date: September 16, 2010Inventors: Howard Lam Ho FONG, Richard Dale Swain
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Publication number: 20100217048Abstract: In a process for producing hydroperoxides, 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 a catalyst comprising a manganese oxide molecular sieve to produce a hydroperoxide of general formula (II): in which R1, R2 and R3 have the same meaning as in formula (I). The hydroperoxide of formula (II) may then be converted to a phenol and an aldehyde or a ketone of the general formula R1COCH2R2 (III), in which R1 and R2 have the same meaning as in formula (I). In the case where the ketone is cyclohexanone, this may then be dehydrogenated to produce further phenol.Type: ApplicationFiled: July 8, 2008Publication date: August 26, 2010Inventors: James C. Vartuli, Jihad M. Dakka, Robert C. Lemon
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Publication number: 20100197971Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone. The benzene and hydrogen are then contacted in the at least one reaction zone under hydroalkylation conditions with a catalyst system comprising a molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom, and at least one hydrogenation metal to produce an effluent containing cyclohexylbenzene. The ratio of the total number of moles of hydrogen fed to said at least one reaction zone to the number of moles of benzene fed to said at least one reaction zone is between 0.4 and 0.9:1.Type: ApplicationFiled: August 12, 2008Publication date: August 5, 2010Inventors: Tan-Jen Chen, Francisco M. Benitez, Jane C. Cheng, Jon E. Stanat, John Scott Buchanan
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Publication number: 20100179351Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone. The benzene and hydrogen are then contacted in the at least one reaction zone under hydroalkylation conditions with a catalyst system comprising a molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom, and at least one hydrogenation metal to produce an effluent containing cyclohexylbenzene. The catalyst system has an acid-to-metal molar ratio of from about 75 to about 750.Type: ApplicationFiled: August 12, 2008Publication date: July 15, 2010Inventors: Tan-Jen Chen, Jane C. Cheng, Terry E. Helton, John Scott Buchanan
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Publication number: 20100099919Abstract: A method for producing phenol and acetone in a multi-stage process at an elevated temperature from a cumene hydroperoxide mixture comprising cumene, the method comprising the steps of a) reacting the cumene hydroperoxide mixture with a 2-hydroxybenzenesulfonic acid catalyst having a concentration of 0.1 to 1 mmol/L acid catalyst to form a second mixture comprising phenol, acetone and dicumyl peroxide in a first stage and decomposing the second mixture in a second stage to produce a third mixture comprising phenol and acetone.Type: ApplicationFiled: October 13, 2009Publication date: April 22, 2010Applicant: SABIC INNOVATIVE PLASTICS IP B.V.Inventors: Mark E. Nelson, Arkady Samuilovich Dykman, Andrey Vladimirovich Zinenkov, Victor Vladimirovich Pinson, Ilja Nikolayevich Grebenshchikov, Dmitrij Nikolayevich Zhukov
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Publication number: 20100087686Abstract: An integrated process for producing aromatic hydrocarbons and ethylene and/or propylene and optionally other lower olefins from low molecular weight hydrocarbons, preferably methane, which comprises: (a) contacting at least one low molecular weight alkane, preferably methane, with a halogen, preferably bromine. under process conditions sufficient to produce a monohaloalkane, preferably monobromomethane, (b) reacting the monohaloalkane in the presence of a coupling catalyst to produce aromatic hydrocarbons and C2+ alkanes, (c) separating the aromatic hydrocarbons from the product mixture of step (b) to produce aromatic hydrocarbons, and (d) cracking at least part of the C2+ alkanes in an alkane cracking system to produce ethylene and/or propylene and optionally other lower olefins.Type: ApplicationFiled: October 5, 2009Publication date: April 8, 2010Inventors: Howard Lam Ho FONG, Richard Dale SWAIN
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Publication number: 20090306433Abstract: A process for producing phenol and methyl ethyl ketone comprises contacting benzene and a C4 olefin under alkylation conditions and in the presence of an alkylation catalyst to produce an alkylation effluent comprising sec-butylbenzene and C8+ olefins. The alkylation effluent is then treated to reduce the amount of said C8+ olefins and produce a treated effluent, whereafter the sec-butylbenzene in the treated effluent is oxidized to produce a hydroperoxide and the hydroperoxide is cleaved to produce phenol and methyl ethyl ketone.Type: ApplicationFiled: February 8, 2007Publication date: December 10, 2009Inventors: Jihad M. Dakka, Edmund J. Mozeleski, Jane C. Cheng, Francisco M. Benitez, Jon E. Stanat, John S. Buchanan
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Publication number: 20090264685Abstract: A method for producing phenol and acetone in a multi-stage process at an elevated temperature from a cumene hydroperoxide mixture comprising cumene, comprises the steps of: a) distilling an amount of cumene from the cumene hydroperoxide mixture until the cumene mass % is 0 to 7 mass % relative to the total mass of the cumene hydroperoxide mixture, b) reacting the cumene hydroperoxide mixture with an acid catalyst form to a second mixture comprising phenol, acetone and dicumyl peroxide in a first stage, and c) decomposing the second mixture in a second stage to produce phenol and acetone, wherein an amount of phenol approximately equal to the amount of distilled from the cumene hydroperoxide mixture is added to the cumene hydroperoxide mixture before the reacting step b). The amount of hydroxyacetone is reduced, thereby, improving the quality of commercial-grade phenol and the products made from the phenol.Type: ApplicationFiled: April 15, 2009Publication date: October 22, 2009Applicant: SABIC Innovative Plastics IP B.V.Inventors: Mark E. Nelson, Arkady Samuilovich Dykman, Andrey Vladimirovich Zinenkov, Victor Vladimirovich Pinson, Ilja Nikolayevich Grebenshchikov
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Publication number: 20090156870Abstract: A process for producing aromatic hydrocarbons which comprises a) contacting ethane or mixed lower alkanes with an aromatic hydrocarbon conversion catalyst to produce reaction products including benzene, b) separating methane, hydrogen, and C2-5 hydrocarbons from the reaction products of step a), and c) hydrodealkylating the remaining reaction products to produce benzene. In a preferred embodiment, the feed is split into two streams, one of which is catalytically or thermally cracked to produce ethylene which is then combined with the remaining ethane or lower alkanes and contacted with the aromatic hydrocarbon conversion catalyst.Type: ApplicationFiled: December 10, 2008Publication date: June 18, 2009Inventors: Ann Marie Lauritzen, Ajay Madhav Madgavkar
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Publication number: 20090093656Abstract: The present invention relates to a process for the production of iso-propanol by liquid phase hydrogenation of acetone to iso-propanol in at least two hydrogenation reaction stages, each reaction stage comprising a hydrogenation reaction zone, wherein the hydrogenation reaction product leaving the reaction zone of the first reaction stage contains unreacted acetone and a product stream comprising acetone and iso-propanol is transferred to the reaction zone of a subsequent reaction stage said product stream having at the inlet to the reaction zone of said subsequent reaction stage a temperature of 60 to 100° C., wherein the temperature of the product stream leaving the reaction zone of said subsequent reaction stage at the outlet from said reaction zone is at most 40° C. higher than the temperature of the product stream entering said reaction zone at the inlet to said reaction zone and the temperature in said subsequent reaction zone does not exceed 125° C.Type: ApplicationFiled: October 3, 2008Publication date: April 9, 2009Applicant: INEOS PHENOT GMBH & CO. KGInventors: Ralf Bonmann, Werner Pompetzki, Markus Weber
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Patent number: 7491855Abstract: Use of a specific combination of catalysts for the first and second steps of the process for the conversion of CHP to BPA provides high yields of BPA and low impurity yields, without a requirement for the intermediate purification steps. In the first step, CHP is cleaved in the presence of an acid treated clay such as acid treated Montmorillonite clay to produce phenol and acetone. In the second step, the phenol and acetone produced is reacted, preferably without intermediate purification, in the presence of a cation exchange resin catalyst that includes a cation exchange resin and a mercaptan or mercaptoalkanoic acid promoter to produce BPA.Type: GrantFiled: June 4, 2003Date of Patent: February 17, 2009Assignee: Sabic Innovative Plastics IP B.V.Inventors: Pramod Shankar Kumbhar, Jegadeesh Thampi, Bharat Singh, John W. Fulmer, Prashant Anil Tatake
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Patent number: 7485758Abstract: A method for the production of phenol and acetone from a cumene hydroperoxide mixture comprises a first stage and a second stage and at least two serially connected reactors, wherein the first stage comprises decomposition of a cumene hydroperoxide mixture in the presence of a catalyst mixture to form a dicumyl peroxide mixture, and the second stage comprises formation of a phenol and acetone mixture from decomposition of the dicumyl peroxide mixture formed in the first stage, wherein, the first stage further comprises: a) forming a catalyst mixture by combining sulfuric acid and phenol in a weight ratio of from 2:1 to 1:1000 in a catalyst formation reactor, b) holding the catalyst mixture in the catalyst formation reactor at a temperature of about 20 to 80° C. for about 1 to 600 minutes; and, c) adding the catalyst mixture to the cumene hydroperoxide mixture to form the phenol and acetone mixture.Type: GrantFiled: September 26, 2007Date of Patent: February 3, 2009Assignee: SABIC Innovative Plastics IP B.V.Inventors: Mark Nelson, Willem Lodewyk Sederel, Arkady Samuilovich Dyckman, Ilya Nikolaevich Grebenshchikov, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov
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Patent number: 7482493Abstract: A method for the production of phenol and acetone from a cumene hydroperoxide mixture comprises: decomposing the cumene hydroperoxide mixture in the presence of a catalyst mixture to form a mixture comprising phenol and acetone, wherein the method further comprises: a) forming the catalyst mixture in a catalyst formation reactor by combining sulfuric acid and phenol in a weight ratio of from 2:1 to 1:1000; b) holding the catalyst mixture in the catalyst formation reactor at a temperature of about 20 to 80° C. for about 1 to 600 minutes; and c) adding the catalyst mixture to the cumene hydroperoxide mixture to form the phenol and acetone mixture. Running the process in this manner reduces the yield of hydroxyacetone and, consequently, improves the quality of the commercial phenol. Moreover, this method reduces consumption of sulfuric acid in comparison with the process in which sulfuric acid is used as catalyst.Type: GrantFiled: September 26, 2007Date of Patent: January 27, 2009Assignee: SABIC Innovative Plastics IP B.V.Inventors: Mark Nelson, Willem Lodewyk Sederel, Arkady Samuilovich Dyckman, Ilya Nikolaevich Grebenshchikov, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov
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Publication number: 20080214873Abstract: A method for the production of phenol and acetone from a cumene hydroperoxide mixture comprises a first stage and a second stage and at least two serially connected reactors, wherein the first stage comprises decomposition of a cumene hydroperoxide mixture in the presence of a catalyst mixture to form a dicumyl peroxide mixture, and the second stage comprises formation of a phenol and acetone mixture from decomposition of the dicumyl peroxide mixture formed in the first stage, wherein, the first stage further comprises: a) forming a catalyst mixture by combining sulfuric acid and phenol in a weight ratio of from 2:1 to 1:1000 in a catalyst formation reactor, b) holding the catalyst mixture in the catalyst formation reactor at a temperature of about 20 to 80° C. for about 1 to 600 minutes; and, c) adding the catalyst mixture to the cumene hydroperoxide mixture to form the phenol and acetone mixture.Type: ApplicationFiled: September 26, 2007Publication date: September 4, 2008Inventors: Mark Nelson, Willem Lodewyk Sederel, Arkady Samuilovich Dyckman, Ilya Nikolaevich Grebenshchikov, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov
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Publication number: 20080214872Abstract: A method for the production of phenol and acetone from a cumene hydroperoxide mixture comprises: decomposing the cumene hydroperoxide mixture in the presence of a catalyst mixture to form a mixture comprising phenol and acetone, wherein the method further comprises: a) forming the catalyst mixture in a catalyst formation reactor by combining sulfuric acid and phenol in a weight ratio of from 2:1 to 1:1000; b) holding the catalyst mixture in the catalyst formation reactor at a temperature of about 20 to 80° C. for about 1 to 600 minutes; and c) adding the catalyst mixture to the cumene hydroperoxide mixture to form the phenol and acetone mixture. Running the process in this manner reduces the yield of hydroxyacetone and, consequently, improves the quality of the commercial phenol. Moreover, this method reduces consumption of sulfuric acid in comparison with the process in which sulfuric acid is used as catalyst.Type: ApplicationFiled: September 26, 2007Publication date: September 4, 2008Inventors: Mark Nelson, Willem Lodewyk Sederel, Arkady Samuilovich Dyckman, Ilya Nikolaevich Grebenshchikov, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov
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Publication number: 20080188694Abstract: The present invention provides a process for decomposing a cumene hydroperoxide to produce phenol and acetone. The process utilizes a solid catalyst that can be non-layered or layered. The process includes: (1) introducing a process stream containing cumene hydroperoxide into a reaction vessel; (2) contacting the process stream with catalyst particles to form a process stream; and (3) withdrawing a portion of the product stream from the reactor and recovering phenol and acetone products.Type: ApplicationFiled: December 19, 2007Publication date: August 7, 2008Inventors: Robert J. Schmidt, Deng-Yang Jan, Raelynn M. Miller, James A. Johnson
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Patent number: 7396961Abstract: The present invention relates to a process for decomposing organic hydroperoxides in the presence of a catalyst. It provides a process for decomposing organic hydroperoxides in the presence of a catalyst into a mixture of alcohols and ketones, in which the catalyst comprises at least one ruthenium-based catalytically active metallic element incorporated into a solid support chosen from the group comprising metal oxides and carbon blacks, such as the carbon blacks obtained by the pyrolysis of organic compounds. The process of the invention is especially useful in the decomposition of important chemical intermediates such as cyclohexyl hydroperoxide.Type: GrantFiled: January 20, 2006Date of Patent: July 8, 2008Assignee: Rhodia Polyamide IntermediatesInventors: Didier Bonnet, Eric Fache, Aline Seigneurin
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Publication number: 20080033217Abstract: 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, is contacted 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: ApplicationFiled: July 13, 2007Publication date: February 7, 2008Inventors: Jihad Mohammed Dakka, Doron Levin, John Scott Buchanan, Jon Edmond Randolph Stanat
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Patent number: 7312365Abstract: A process for cleaving an oxidation product comprising s-butyl benzene hydroperoxide and/or cumene hydroperoxide which reduces the production of non-recoverable by-products from dimethylbenzyl alcohol (DMBA) and ethyl methyl benzyl carbinol (EMBA).Type: GrantFiled: January 21, 2004Date of Patent: December 25, 2007Assignee: Shell Oil CompanyInventor: Jesse Raymond Black
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Publication number: 20070244346Abstract: The present invention relates to method for producing phenol which includes: a) oxidizing cumene to form an oxidation product containing cumene hydroperoxide; b) cleaving the oxidation product using an acidic catalyst to form a cleavage product containing phenol, acetone and impurities; c) neutralizing and washing the cleavage product with a basic aqueous medium to obtain a neutralized cleavage product; d) separating the neutralized cleavage product by at least one distillation step into at least a phenol containing fraction and an aqueous fraction comprising hydroxyacetone; e) treating the aqueous fraction with an oxidizing agent in presence of a base to obtain a basic aqueous medium reduced in hydroxyacetone; f) recycling at least a portion of the basic aqueous medium to the neutralizing and washing step c); and g) recovering phenol from the phenol containing fraction obtained in step d).Type: ApplicationFiled: April 17, 2007Publication date: October 18, 2007Applicant: INEOS Phenol GmbH & Co. KGInventors: Otto Schnurr, Manfred Weber, Markus Weber
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Patent number: 7154010Abstract: Use of a specific combination of catalysts for the first and second steps of the process for the conversion of CHP to BPA provides high yields of BPA and low impurity yields, without a requirement for the intermediate purification steps. In the first step, CHP is cleaved in the presence of a sulfated metal oxide catalyst such as sulfated Zirconia to produce phenol and acetone. In the second step, the phenol and acetone produced is reacted, preferably without intermediate purification, in the presence of a cation exchange resin catalyst that includes a cation exchange resin and a mercaptan or mercaptoalkanoic acid promoter to produce BPA.Type: GrantFiled: June 4, 2003Date of Patent: December 26, 2006Assignee: General Electric CompanyInventors: Pramod Shankar Kumbhar, Jegadeesh Thampi, Bharat Singh, John W. Fulmer, Prashant Anil Tatake
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Patent number: 7141701Abstract: A process for decomposing a cumene oxidation product mixture containing cumene hydroperoxide (CHP) and dimethylphenolcarbinol (DMPC) to produce phenol and acetone.Type: GrantFiled: August 19, 2005Date of Patent: November 28, 2006Assignee: UOP LLCInventors: Robert J. Schmidt, Russell C. Schulz, Patrick J. Bullen, Constante P. Tagamolila, Steven P. Lankton, Gary A. Peterson, Michael E. Fettis
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Patent number: 7141700Abstract: A process for the decomposition of a cumene oxidation product mixture to produce phenol and acetone with reduced by-product formation by introducing the cumene oxidation mixture into an inlet of a decomposing vessel containing indirect heat exchange surfaces wherein the cumene oxidation product mixture and a circulating stream are admixed, reacted and cooled by passage around the indirect heat exchange surfaces.Type: GrantFiled: August 19, 2005Date of Patent: November 28, 2006Assignee: UOP LLCInventors: Robert J. Schmidt, Russell C. Schulz, Patrick J. Bullen, Constante P. Tagamolila, Steven P. Lankton, Gary A. Peterson, Michael E. Fettis
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Patent number: 7126029Abstract: The present invention provides a method and apparatus for in-process handling of concentrated cumene hydroperoxide (“CHP”) in a process for the production of phenol and acetone by the decomposition of CHP. The method of the present invention makes use of a tube and shell type heat exchanger as a vessel to accumulate a working volume of concentrated CHP from a distillation unit. Concentrated CHP is then fed to a decomposer unit from the accumulated working volume. Use of a tube and shell type heat exchanger improves safety over designs that make use of an unmodified tank or drum.Type: GrantFiled: February 2, 2004Date of Patent: October 24, 2006Assignee: Sunoco, Inc. (R&M)Inventors: James G. Skipworth, James M. Delabar
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Patent number: 7109385Abstract: A process for producing a phenol product generally comprises a first step comprising reacting in a first reactor a feed stream comprising cumene hydroperoxide and water with an acid catalyst to produce an effluent comprising the phenol product, acetone, and at least 1% by weight residual cumene hydroperoxide, and a second step comprising passing the effluent into a second reactor and decomposing the residual cumene hydroperoxide, wherein during said process the ratio of phenol to acetone is maintained at a molar ratio of greater than 1:1, and wherein the water in each of the first and second steps is present in an amount more than 0 and less than or equal to 5 weight percent based on the total weight of the feed stream or effluent, and wherein the process is continuous.Type: GrantFiled: March 29, 2005Date of Patent: September 19, 2006Assignee: General Electric CompanyInventors: Prashant Anil Tatake, Pramod Shankar Kumbhar, Bharat Singh, John William Fulmer, Sabyasachi Mandal, Arun N. Kumar, Rupesh Pawar
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Patent number: 6984761Abstract: A process is disclosed for producing ?-methylstyrene, acetone, and phenol wherein the amount of ?-methylstyrene produced may be controlled by selectively converting a portion of the cumene hydroperoxide to dimethyl phenyl carbinol, the hydrated form of ?-methylstyrene. The dimethyl phenyl carbinol thus produced will lead to increased production of ?-methylstyrene upon dehydration in the acid cleavage unit of the phenol plant. By controlling the fraction of the cumene hydroperoxide reduced to dimethyl phenyl carbinol, the amount of ?-methylstyrene produced in the plant can be continuously set to meet the demand of the market for ?-methylstyrene. Also disclosed is a non-acidic catalyst for reduction of cumene hydroperoxide.Type: GrantFiled: December 16, 2002Date of Patent: January 10, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Doron Levin, C. Morris Smith, Jose Guadalupe Santiesteban, James C. Vartuli
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Patent number: 6939995Abstract: Process for the preparation of isopropanol is provided, wherein a benzene-containing feed of acetone is hydrogenated to obtain isopropanol and hydrogenation products of benzene. Combination of such a process with a process for the preparation of phenol and combination of such a process with a series of separation steps is provided.Type: GrantFiled: November 14, 2002Date of Patent: September 6, 2005Assignee: Shell Oil CompanyInventors: Leslie Andrew Chewter, Wilhelmus Cornelis Nicolaas Dekker, Stephane Jean Pierre Lecrivain, Carolus Matthias Anna Maria Mesters, Andrew Neave Rogers, Lydia Singoredjo
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Patent number: 6888035Abstract: A method for producing phenol is disclosed which includes oxidizing cumene to form cumene hydroperoxide and acid cleavage to form cumene, phenol, acetone, and various byproducts, including alpha methylstyrene, followed by a subsequent hydrogenation of at least a part of the acetone and substantially all of the alpha methylstyrene.Type: GrantFiled: September 25, 2001Date of Patent: May 3, 2005Assignee: ExxonMobil Chemical Patents Inc.Inventors: Kevin J. Fallon, Chung-Ming Chi, Henry Y. Hwang, Frank A. Demers
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Patent number: 6875898Abstract: The present invention relates to a process for preparing phenols by adding an aqueous base to the reaction product from the acid-catalyzed cleavage of alkylaryl hydroperoxides while maintaining a homogeneous phase prior to the work-up of the product.Type: GrantFiled: April 4, 2003Date of Patent: April 5, 2005Assignee: Ineos Phenol GmbH & Co. KGInventors: Manfred Weber, Reinhard Sigg, Michael Lausmann, Siegmund Greschek
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Patent number: 6841704Abstract: Disclosed is a method for the preparation of cumene by reacting isopropanol or a mixture of isopropanol and propene with benzene in the presence of a ?-zeolite catalyst having a SiO2/Al2O3 molar ratio greater than 10:1 that can be integrated in a process for preparing phenol, which comprises preparing cumene as described above, oxidizing cumene to cumene hydroperoxide, acid-catalyzed cleavage of cumene hydroperoxide to give phenol and acetone, and hydrogenating acetone to form isopropanol.Type: GrantFiled: February 19, 2001Date of Patent: January 11, 2005Assignee: Ineos Phenol GmbH & Co. KGInventors: Michael Sakuth, Uwe Tanger, Markus Weber
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Publication number: 20040267052Abstract: The present invention relates to a process for decomposing organic hydroperoxides in the presence of a catalyst. It provides a process for decomposing organic hydroperoxides in the presence of a catalyst into a mixture of alcohols and ketones, in which the catalyst comprises at least one ruthenium-based catalytically active metallic element incorporated into a solid support chosen from the group comprising metal oxides and carbon blacks, such as the carbon blacks obtained by the pyrolysis of organic compounds. The process of the invention is especially useful in the decomposition of important chemical intermediates such as cyclohexyl hydroperoxide.Type: ApplicationFiled: August 18, 2004Publication date: December 30, 2004Inventors: Didier Bonnet, Eric Fache, Aline Seigneurin
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Patent number: 6825387Abstract: Washed cleavage product (WCP) in a phenol manufacturing process is treated to remove sodium ions. The WCP is contacted with a cation exchange resin in hydrogen form, and then with anion exchange resin in free base or hydroxide form, to produce a WCP essentially free of sodium ions. The cation and anion exchange resins are regenerated with acid and caustic, respectively. The treatment improves productivity and product quality of new and existing phenol processes.Type: GrantFiled: September 11, 2003Date of Patent: November 30, 2004Assignee: Kellogg Brown & Root, Inc.Inventors: Theodor Robert Wilks, Mark Thornton Vandersall, William Frederick Rogers, Jr.
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Publication number: 20040236152Abstract: A process for producing phenol and methyl ethyl ketone (MEK).Type: ApplicationFiled: January 21, 2004Publication date: November 25, 2004Inventors: Jesse Raymond Black, Jiemin Yang, James Laurel Buechele
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Patent number: 6800787Abstract: A catalyst for acidolysis of an aromatic hydroperoxy compound, containing little scale, prepared by gasifying liquid sulfuric anhydride and dissolving gasified sulfuric anhydride in a ketone solvent, and a process for producing a hydroxy aromatic compound using the catalyst.Type: GrantFiled: September 30, 2003Date of Patent: October 5, 2004Assignee: Sumitomo Chemical Company, LimitedInventor: Mitsuru Oonuma
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Publication number: 20040082817Abstract: The present invention describes a high yield and simplified method of preparing phenols and carbonyl compounds, such as acetaldehyde, through the catalytic decomposition of aromatic hydroperoxides. The synthetic process generally consists of decomposing hydroperoxides under a positive gas atmosphere and at an elevated temperature (80 to 100° C.) in the presence of a catalytic amount (0.01-0.8 mass percent (%)) of an anionic surface-active agent of the formula R—OSO3M or R—OP3Z2, where “M” is Na or K, where “Z” is Na, K or an alkyl groups containing between ten and fourteen carbons (C10-C14) and where “R” is an alkyl group consisting of between ten and fourteen carbons (C10-C14).Type: ApplicationFiled: October 24, 2002Publication date: April 29, 2004Applicant: NEUROK LLCInventor: Olga Tarasovna Kasaikina
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Publication number: 20040073071Abstract: A catalyst for acidolysis of an aromatic hydroperoxy compound, containing little scale, prepared by gasifying liquid sulfuric anhydride and dissolving gasified sulfuric anhydride in a ketone solvent, and a process for producing a hydroxy aromatic compound using the catalyst.Type: ApplicationFiled: September 30, 2003Publication date: April 15, 2004Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Mitsuru Oonuma
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Publication number: 20040015021Abstract: A composition of an antioxidant of the formula 1Type: ApplicationFiled: October 30, 2002Publication date: January 22, 2004Inventors: Paul E. Adams, Thomas J. Wolak
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Patent number: 6680414Abstract: The present invention provides a process, which includes: in a homogeneous liquid phase including water, and over a fixed-bed catalyst, continuously hydrogenating at least one hydroformylation product obtained from a hydroformylation of one or more C4-16 olefins to produce at least one output mixture; wherein the fixed-bed catalyst includes at least one element of transition group eight of the Periodic Table of the Elements; wherein the output mixture includes at least one corresponding alcohol and from 0.05 to 10% by weight of water; and wherein in a steady-state operation of the process, from 3 to 50% more hydrogen is fed to the hydrogenation than is consumed by the hydrogenation.Type: GrantFiled: December 14, 2001Date of Patent: January 20, 2004Assignee: Oxeno Olefinchemie GmbHInventors: Cord Knoop, Bernhard Scholz, Alfred Kaizik, Dietmar Gubisch, Joachim Schuler, Walter Tötsch, Wilfried Büschken
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Patent number: 6630608Abstract: The present invention relates to a process for preparing phenols, in which the pH of the reaction product from the acid-catalyzed cleavage of alkylaryl hydroperoxides is set to a value of at least 8 at a temperature of at least 100° C. prior to the work-up of the product. This measure enables the content of undesirable by-products, e.g. hydroxyacetone, in the cleavage product to be significantly reduced. This procedure is particularly advantageously integrated into a process for preparing phenols by: a) acid-catalyzed cleavage of alkylaryl hydroperoxides and b) thermal after-treatment of the cleavage product from step a), with the temperature in step b) being higher than in step a) and is at least 100° C., wherein the adjustment to a pH of at least 8 is carried out after the thermal after-treatment and prior to cooling of the cleavage product.Type: GrantFiled: March 4, 2002Date of Patent: October 7, 2003Assignee: INEOS Phenol & GmbH Co., KGInventors: Uwe Tanger, Reinhard Sigg, Siegmund Greschek, Manfred Weber
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Publication number: 20030168329Abstract: A process for separating sulfonic acid compounds from a phenolic solvent is provided by contacting the phenolic solvent with a hydrotalcite-type material (HTM). The process can be applied in the conventional industrial process for converting cumene to phenol to remove sulfonic acid compounds from the phenol product. A process and a facility for producing purified phenol by converting cumene to phenol are provided. In the conversion of cumene to phenol, the phenol often contains carbonyl-type impurities. The phenol and carbonyl-type impurities are reacted in the presence of a sulfonic acid cation exchange resin catalyst (IER) to produce a reaction product that may contain sulfonic acid compounds. The reaction product is contacted with an HTM to reduce the amount of sulfonic acid compounds which may be present and to produce a purified phenol-containing stream. The purified phenol-containing stream may be further purified using conventional separation techniques, such as distillation.Type: ApplicationFiled: March 6, 2002Publication date: September 11, 2003Inventors: John W. Fulmer, Nitin Vaish, Pramod Kumbhar, Jacob L. Oberholtzer, R. Jothi Mahalingam
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Publication number: 20030153793Abstract: The invention relates to a process for the preparation of cumene by reacting isopropanol or a mixture of isopropanol and propene with benzene in presence of a &bgr;-zeolite catalyst having a SiO2/Al2O3 molar ratio greater than 10:1 that can be integrated in a process for preparing phenol, which comprises the steps I. preparation of cumene as described above, II. oxidation of cumene to cumene hydroperoxide, III. acid-catalyzed cleavage of cumene hydroperoxide to give phenol and acetone and IV. hydrogenation of acetone to form isopropanol. In the reaction of isopropanol with benzene, propene is formed by dehydration of isopropanol simultaneously with the alkylation of benzene to cumene by means of isopropanol and the propene formed is likewise used for the alkylation of benzene to cumene. Formation of n-propylbenzene in this process step according to the invention is barely observed or is in the range below 150 wppm.Type: ApplicationFiled: January 27, 2003Publication date: August 14, 2003Inventors: Michael Sakuth, Uwe Tanger, Markus Weber
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Patent number: 6586640Abstract: A process for the manufacture of a hydroxy-substituted organic compound comprising decomposing an organic hydroperoxide, preferably a compound of the formula Ar—C(CH3)2O2H, wherein Ar is a substituted or unsubstituted mononuclear or polynuclear aromatic group. The decomposition is carried out in the presence of a catalyst comprising highly fluorinated polymer having sulfonic acid groups with the catalyst being in the form of particles of which at least about 20 weight % have a particle size less than about 300 &mgr;m. Cumene hydroperoxide can be decomposed in the process to phenol and acetone which can be reacted to form bisphenol A in the presence of the same catalyst that was used for the decomposition.Type: GrantFiled: June 20, 2002Date of Patent: July 1, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Birchard Lloyd, Qun Sun, Mark Andrew Harmer, Edward George Howard, Jr.
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Patent number: 6583326Abstract: Phenol is separated from a mixture containing hydroxyacetone, cumene, water and phenol, by fractionating the mixture in a process with a fractional distillation step and a phase separation step to provide a single phenol fraction containing less than 300 ppm of hydroxyacetone. In the work-up by distillation of cleavage product mixtures, the hydroxyacetone can be removed from the cleavage product mixture together with a phenol fraction from which the hydroxyacetone has to be removed. A process can be used for purifying cleavage product mixtures obtained in the cleavage of alkylaryl hydroperoxides such as cumene hydroperoxide. The process allows separation of phenol and acetone from mixtures obtained in the cleavage of cumene hydroperoxide.Type: GrantFiled: October 5, 2001Date of Patent: June 24, 2003Assignee: Phenolchemie GmbH & Co. KGInventors: Christoph Schwarz, Markus Weber, Uwe Tanger, Hermann-Josef Korte, Jochen Ullrich
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Patent number: RE40668Abstract: A method for the enhanced decomposition of cumene hydroperoxide by acidic catalyst to phenol and acetone which comprises decomposing cumene hydroperoxide in a non-isothermal manner in the presence of excess acetone whereby the molar ratio of acetone to phenol in a decomposition reactor is from about 1.1:1 to 1.5:1. A method for the selectivity of the decomposition of dicumyl peroxide to alpha methylstyrene also phenol and acetone in the presence of an acidic catalyst which comprises carrying out the decomposition at a temperature of from about 80° to 110° C. A method for carrying out the decomposition of dicumyl peroxide with an acidic catalyst system which comprises performing such decomposition in the presence of the reaction product of (1) an amine with (2) an acidic material which can catalyze the decomposition of CHP.Type: GrantFiled: October 19, 1995Date of Patent: March 17, 2009Assignees: SABIC Innovative Plastics IP B.V., ILLA International Ltd.Inventor: Vladimir M. Zakoshansky