Preparing By Cleavage Of Hydroperoxide Or Other Peroxide Patents (Class 568/798)
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Patent number: 8575413Abstract: The invention relates to a process for the alkylation of benzene with isopropanol (IPA) as alkylating agent, or blends of isopropanol and propylene, which comprises effecting said reaction completely in gaseous phase and in the presence of a catalytic system containing a zeolite belonging to the MTW family.Type: GrantFiled: September 7, 2009Date of Patent: November 5, 2013Assignee: Polimeri Europa S.p.A.Inventors: Loreno Lorenzoni, Paolo Calaresu, Pier Gianni Cabras
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Patent number: 8546633Abstract: A method for producing an alkylated aromatic compound includes a step (i) of producing a reaction product (a1) containing the alkylated aromatic compound and water by the reaction of an aromatic compound, a ketone, and hydrogen using a metal component containing at least one metallic element of copper, nickel, cobalt, and rhenium and a solid acid substance; a step (ii) of forming a dehydrated product (a2) from at least a portion of the reaction product (a1) by removing at least a portion of the water in the reaction product (a1); and a step (iii) of producing a reaction product (a3) containing the alkylated aromatic compound by bringing at least a portion of the dehydrated product (a2) into contact with a solid acid substance.Type: GrantFiled: October 22, 2009Date of Patent: October 1, 2013Assignee: Mitsui Chemicals, Inc.Inventors: Kenji Fujiwara, Tsuneyuki Ohkubo, Terunori Fujita, Shinobu Aoki, Masayasu Ishibashi, Masao Imai, Kozo Yasuda
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Patent number: 8536394Abstract: According to a process of the invention, a ketone, an aromatic compound and hydrogen as starting materials are reacted together in a single reaction step to produce an alkylaromatic compound in high yield. A process for producing phenols in the invention includes a step of performing the above alkylation process and does not increase the number of steps compared to the conventional cumene process. The process for producing alkylated aromatic compounds includes reacting an aromatic compound such as benzene, a ketone such as acetone and hydrogen in the presence of a solid acid substance, preferably a zeolite, and a silver-containing catalyst.Type: GrantFiled: March 12, 2010Date of Patent: September 17, 2013Assignee: Mitsui Chemicals, Inc.Inventors: Tsuneyuki Ohkubo, Shinobu Aoki, Masayasu Ishibashi, Masao Imai, Terunori Fujita, Kenji Fujiwara
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Patent number: 8530705Abstract: A purification method of dihydroxybenzene comprising the following steps, for obtaining purified dihydroxybenzene from crude dihydroxybenzene containing at least isopropenylphenol and hydroxyacetophenone as impurities: first extraction step, distillation step, second extraction step, and recovery step.Type: GrantFiled: March 24, 2010Date of Patent: September 10, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Mayumi Nishimura, Shigeru Goto, Tomoyuki Noritake
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Publication number: 20130217921Abstract: In a process for producing phenol and cyclohexanone, a feed comprising cyclohexylbenzene is oxidized to produce an oxidation reaction product comprising cyclohexyl-1-phenyl-1-hydroperoxide. At least a portion of the oxidation reaction product is then cleaved to produce a cleavage reaction product comprising phenol, cyclohexanone, and at least one contaminant. At least a portion of the cleavage reaction product is contacted with an acidic material to convert at least a portion of the at least one contaminant to a converted contaminant and thereby produce a modified reaction product.Type: ApplicationFiled: August 16, 2011Publication date: August 22, 2013Applicant: ExxonMobil Chemical Patents Inc.Inventors: Keith H. Kuechler, Francisco M. Benitez
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Publication number: 20130217922Abstract: Disclosed herein is a process for producing phenol. The process includes oxidizing at least a portion of a feed comprising cyclohexylbenzene to produce an oxidation composition comprising cyclohexyl-1-phenyl-1-hydroperoxide. The oxidation composition may then be cleaved in the presence of an acid catalyst to produce a cleavage reaction mixture comprising the acid catalyst, phenol and cyclohexanone. At least a portion of the cleavage reaction mixture may be neutralized with a basic material to form a treated cleavage reaction mixture. In various embodiments, the treated cleavage reaction mixture contains no greater than 50 wppm of the acid catalyst or no greater than 50 wppm of the basic material.Type: ApplicationFiled: August 16, 2011Publication date: August 22, 2013Inventors: Keith H. Kuechler, Francisco M. Benitez, Kun Wang, James R. Lattner, Christopher L. Becker
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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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Publication number: 20130203984Abstract: In a process for oxidizing a hydrocarbon to a product comprising at least one of the corresponding hydroperoxide, alcohol, ketone, carboxylic acid and dicarboxylic acid, the hydrocarbon is contacted with an oxygen-containing compound in at least one oxidation zone in the presence of a catalyst comprising a cyclic imide having an imide group of formula (I): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group and wherein the oxygen-containing compound supplied to said at least one oxidation zone has a water content of less than or equal to 0.6% by weight of the oxygen-containing compound.Type: ApplicationFiled: August 16, 2011Publication date: August 8, 2013Inventors: Christopher L. Becker, Jihad M. Dakka, Franisco M. Benitez, Edmund J. Mozeleski
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Publication number: 20130202522Abstract: The invention relates to hydroalkylation processes. In the processes, a hydrogen stream comprising hydrogen and an impurity is treated to reduce the amount of the impurity in the hydrogen stream. The hydrogen is then hydroalkylated with benzene to form at least some cyclohexylbenzene. The processes also relate to treating a benzene stream comprising benzene and an impurity with an adsorbent to reduce the amount of the impurity in the benzene stream. The hydroalkylation processes described herein may be used as part of a process to make phenol.Type: ApplicationFiled: April 4, 2011Publication date: August 8, 2013Inventors: Tan-Jen Chen, Teng Xu, Terry Helton, Francisco M. Benitez, Charles M. Smith
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Patent number: 8487140Abstract: In a process for producing phenol, cyclohexylbenzene is oxidized to produce cyclohexylbenzene hydroperoxide and then the resultant cyclohexylbenzene hydroperoxide is cleaved to produce an effluent stream comprising phenol and cyclohexanone. At least a portion of the effluent stream is then fed to at least one dehydrogenation reaction zone, where the effluent stream portion is contacted with a dehydrogenation catalyst under conditions effective to convert at least part of the cyclohexanone in the effluent portion into phenol and hydrogen.Type: GrantFiled: July 14, 2009Date of Patent: July 16, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: John S. Buchanan, Jon E. Stanat, Tan-Jen Chen, Jihad M. Dakka, James R. Lattner
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Publication number: 20130172514Abstract: In a process for producing a cycloalkylaromatic compound, an aromatic compound, hydrogen and at least one diluent are supplied to a hydroalkylation reaction zone, such that the weight ratio of the diluent to the aromatic compound supplied to the hydroalkylation reaction zone is at least 1:100. The aromatic compound, hydrogen and the at least one diluent are then contacted under hydroalkylation conditions with a hydroalkylation catalyst in the hydroalkylation reaction zone to produce an effluent comprising a cycloalkylaromatic compound.Type: ApplicationFiled: June 28, 2011Publication date: July 4, 2013Applicant: ExxonMobil Chemical Patents Inc.Inventors: Teng Xu, Wenyih F. Lai
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Patent number: 8445738Abstract: 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: GrantFiled: September 23, 2009Date of Patent: May 21, 2013Assignee: Badger Licensing LLCInventors: Shyh-Yuan Hwang, Dana E. Johnson, Joseph C. Peters, Chung-Ming Chi, Kevin J. Fallon, Francis A. Demers
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Patent number: 8440864Abstract: In a process for producing sec-butylbenzene, a C4 olefinic hydrocarbon feedstock comprising isobutene and at least one n-butene is contacted with methanol and/or water in the presence of an acid catalyst to selectively oxygenate isobutene to produce an effluent stream rich in n-butene and containing less isobutene than the feedstock. The effluent stream is then contacted with benzene under alkylation conditions and in the presence of an alkylation catalyst to produce alkylation stream comprising sec-butylbenzene.Type: GrantFiled: August 4, 2009Date of Patent: May 14, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: John S. Buchanan, Jon E. R. Stanat, James R. Lattner, Jane C. Cheng
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Patent number: 8436213Abstract: In a process for reducing the level of tert-butylbenzene in a mixed butylbenzene feed comprising tert-butylbenzene and sec-butylbenzene, the feed is contacted under dealkylation conditions with a catalyst system comprising a dealkylation catalyst whereby the tert-butylbenzene is selectively dealkylated to produce an effluent stream which comprises benzene and which has a lower concentration of tert-butylbenzene than said feed.Type: GrantFiled: August 4, 2009Date of Patent: May 7, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, Jane C. Cheng, John S. Buchanan
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Publication number: 20130090499Abstract: A catalyst composition comprising: (i) a support; (ii) a first component comprising at least one metal component selected from Group 1 and Group 2 of the Periodic Table of Elements; and (iii) a second component comprising at least one metal component selected from Groups 6 to 10 of the Periodic Table of Elements, wherein the catalyst composition exhibits an oxygen chemisorption of greater than 50%.Type: ApplicationFiled: December 17, 2010Publication date: April 11, 2013Inventors: Teng Xu, Terry E. Helton, Jihad M. Bakka, Tan-Jen Chen, Sabato Miseo, Lorenzo C. Decaul, Edward A. Lemon, JR.
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Patent number: 8404914Abstract: The invention provides an efficient process for producing alkylated aromatic compounds such as cumene in a compact reactor. The invention also provides a process for producing phenol which includes a step of producing cumene by the above process. The process for producing alkylated aromatic compounds of the invention includes feeding raw materials including an aromatic compound and an alcohol in a gas-liquid downward concurrent flow mode to a fixed-bed reactor packed with a solid acid catalyst thereby to produce an alkylated aromatic compound, wherein the raw materials are fed to the reactor in a stream of a gas, and the reaction gas flow rate defined by the equation below is not less than 0.05 at an entrance of a solid acid catalyst layer: ?g·ug·[?air·?water/(?g·?l)]1/2(kgm?2s?1).Type: GrantFiled: June 3, 2009Date of Patent: March 26, 2013Assignee: Mitsui Chemicals, Inc.Inventors: Shinji Senoo, Kazuhiko Kato, Kenji Doi, Katsunari Higashi
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Patent number: 8329956Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted under hydroalkylation conditions with a catalyst system comprising a MCM-22 family molecular sieve and at least one hydrogenation metal. The conditions comprise a temperature of about 140° C. to about 175° C., a pressure of about 135 psig to about 175 psig (931 kPag to 1207 kPag), a hydrogen to benzene molar ratio of about 0.30 to about 0.65 and a weight hourly space velocity of benzene of about 0.26 to about 1.05 hr?1.Type: GrantFiled: March 1, 2012Date of Patent: December 11, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jane C. Cheng, Tan-Jen Chen, Prasenjeet Ghosh
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Publication number: 20120302799Abstract: A catalyst composition comprises (i) a support; (ii) a dehydrogenation component comprising at least one metal or compound thereof selected from Groups 6 to 10 of the Periodic Table of Elements; and (iii) potassium or a potassium compound present in an amount of about 0.15 to about 0.6 wt % of potassium based upon the total weight of the catalyst composition, wherein the catalyst composition has an oxygen chemisorption of greater than 50%.Type: ApplicationFiled: December 17, 2010Publication date: November 29, 2012Inventors: Jihad M. Dakka, Lorenzo C. Decaul, Terry E. Helton, Teng Xu, Jenna L. Wallace
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Publication number: 20120302798Abstract: A dehydrogenation process for the dehydrogenation of at least one dehydrogenatable hydrocarbon, the process comprising contacting a feed comprising the at least one dehydrogenatable hydrocarbon under dehydrogenation conditions with a catalyst composition comprising a support and at least one dehydrogenation component wherein said conditions include a temperature of from 400° C. to 750° C. and a pressure of at least 50 psig (345 kPag).Type: ApplicationFiled: December 17, 2010Publication date: November 29, 2012Inventors: Jihad M. Dakka, Lorenzo C. Decaul, Sabato Miseo, James R. Lattner, Tan-Jen Chen, Terry E. Helton, Teng Xu
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Publication number: 20120283486Abstract: Process for the production in continuous or semi-continuous of phenol/acetone from cumene, via cumene hy-droperoxide (CHP), which comprises: a. producing CHP in an air-lift reactor in which at least the upper and/or lower part of the downcomer has a flaring; b. cleaving the cumene hydroperoxide by means of acid treatment in a loop reactor comprising two heat exchangers connected in series and wherein the feedings of CHP and fresh acetone are in pairs and each pair is positioned up-stream of each exchanger.Type: ApplicationFiled: October 29, 2010Publication date: November 8, 2012Applicant: versalis S.p.A.Inventors: Mauro Burattini, Roberto Bagatin
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Patent number: 8298378Abstract: A method for treating a wastewater containing oxygen-containing compound having a phenolic hydroxyl group or a carbonyl group, including a step of adding an alkali agent to the wastewater containing the oxygen-containing compound having a phenolic hydroxyl group or a carbonyl group to control a pH of the wastewater to 10 or more; and a step of separating a discharge in which the oxygen-containing compound having a phenolic hydroxyl group or a carbonyl group is concentrated through distillation of the wastewater to which the alkali agent has been added.Type: GrantFiled: March 24, 2006Date of Patent: October 30, 2012Assignee: Sumitomo Chemical Company, LimitedInventor: Kenji Itoh
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Patent number: 8247627Abstract: In a process for producing phenol and/or cyclohexanone, benzene and hydrogen are contacted with a first catalyst in a hydroalkylation step to produce a first effluent stream comprising cyclohexylbenzene, cyclohexane, and unreacted benzene. At least part of the first effluent stream is supplied to a first separation system to divide the first effluent stream part into a cyclohexylbenzene-rich stream and a C6 product stream comprising unreacted benzene and cyclohexane.Type: GrantFiled: March 16, 2009Date of Patent: August 21, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jihad M. Dakka, J. Scott Buchanan, Jane C. Cheng, Tan-Jen Chen, Lorenzo C. DeCaul, Terry E. Helton, Jon E. Stanat, Francisco M. Benitez
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Patent number: 8247616Abstract: A method of producing phenol, acetone and alpha-methyl styrene. A mixture of cumene hydroperoxide and dimethylbenzyl alcohol is provided. The mixture is subjected to a first stage reaction in the presence of about 0.5 to 1.5 wt. % water and about 20 to 400 ppm sulfuric acid at a reactor pressure of about 450 to 760 mm Hg, a temperature of about 60 to 85° C., and a residence time of 4 to 45 minutes to produce a composition having an acetone to phenol mole ratio of about 1 to 1.5. The composition is subjected to a second stage reaction in the presence of about 0.5 to 3 wt. % additional water with a second stage reactor temperature of about 110 to 150° C. and a residence time of 0.5 to 30 minutes.Type: GrantFiled: March 28, 2012Date of Patent: August 21, 2012Assignee: Honeywell International Inc.Inventors: Scott R. Keenan, Michael K. Hagans
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Publication number: 20120149942Abstract: There is provided a method for handling an aqueous solution containing a water-soluble substance that changes into a water-insoluble substance over time, including a step of bringing the aqueous solution to be treated containing the water-soluble substance that changes into the water-insoluble substance over time into contact with a water-insoluble organic solvent, and extracting the water-soluble substance into the water-insoluble organic solvent. Preferably, the water-soluble substance is alkylbenzene hydroperoxide, and the water-insoluble substance is alkylbenzene hydroperoxide-derived alcohol. Preferably, the aqueous solution to be treated is an alkaline aqueous phase separated in a water-washing step in a process of manufacturing the alkylbenzene hydroperoxide that has an alkali extraction step, the water-washing step, an oxidation step, and a reaction solution separation step.Type: ApplicationFiled: August 19, 2010Publication date: June 14, 2012Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Mitsuru Onuma, Tomoyuki Noritake, Shigeru Goto
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Patent number: 8178728Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted under hydroalkylation conditions with a catalyst system comprising a MCM-22 family molecular sieve and at least one hydrogenation metal. The conditions comprise a temperature of about 140° C. to about 175° C., a pressure of about 135 psig to about 175 psig (931 kPag to 1207 kPag), a hydrogen to benzene molar ratio of about 0.30 to about 0.65 and a weight hourly space velocity of benzene of about 0.26 to about 1.05 hr?1.Type: GrantFiled: February 24, 2009Date of Patent: May 15, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jane C. Cheng, Tan-Jen Chen, Prasenjeet Ghosh
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Publication number: 20120046499Abstract: In a process for the transalkylation of polycyclohexylbenzenes, a feed containing at least one polycyclohexylbenzene is contacted with benzene under transalkylation conditions with a catalyst comprising a zeolite USY having a silica to alumina molar ratio in excess of 10 to convert at least part of said polycyclohexylbenzene to cyclohexylbenzene.Type: ApplicationFiled: April 14, 2010Publication date: February 23, 2012Inventors: Kun Wang, Jane C. Cheng, Terry E. Helton
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Publication number: 20120004471Abstract: According to a process of the invention, a ketone, an aromatic compound and hydrogen as starting materials are reacted together in a single reaction step to produce an alkylaromatic compound in high yield. A process for producing phenols in the invention includes a step of performing the above alkylation process and does not increase the number of steps compared to the conventional cumene process. The process for producing alkylated aromatic compounds includes reacting an aromatic compound such as benzene, a ketone such as acetone and hydrogen in the presence of a solid acid substance, preferably a zeolite, and a silver-containing catalyst.Type: ApplicationFiled: March 12, 2010Publication date: January 5, 2012Inventors: Tsuneyuki Ohkubo, Shinobu Aoki, Masayasu Ishibashi, Masao Imai, Terunori Fujita, Kenji Fujiwara
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Patent number: 8084648Abstract: In a process for producing cyclohexylbenzene, hydrogen and a liquid feed comprising benzene are introduced into a reaction zone and are contacted in the reaction zone under hydroalkylation conditions to produce cyclohexylbenzene. An effluent stream comprising cyclohexylbenzene and unreacted benzene is removed from the reaction zone and is divided into at least first and second portions, wherein the mass ratio of the effluent stream first portion to the effluent stream second portion is at least 2:1. The effluent stream first portion is then cooled and the cooled effluent stream first portion is recycled to the reaction zone.Type: GrantFiled: January 13, 2009Date of Patent: December 27, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: John S. Buchanan, Jane C. Cheng, Tan-Jen Chen, James R. Lattner
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Publication number: 20110306800Abstract: An improved method for the production of phenol, acetone and alpha-methyl styrene (AMS) from a cumene hydroperoxide and dimethylbenzyl alcohol (DMBA) mixture is described, wherein 0.5-5% additional water by weight is added prior to the final DMBA dehydration step, carried out in the presence of about 20-400 ppm mineral acid catalyst at 110-150° C. for 0.5 to 40 minutes residence time. The use of additional water allows greater flexibility in maintaining optimum temperature in the second stage over a much broader turndown range with fixed equipment, decreases the residual dicumyl peroxide (DCP) at the yield optimum for a given temperature, and increases the overall yield of AMS at optimum conditions at a given temperature.Type: ApplicationFiled: June 9, 2010Publication date: December 15, 2011Inventors: Scott Roy Keenan, Michael Keith Hagans
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Publication number: 20110301387Abstract: Disclosed is a process for producing phenol or a substituted phenol and a co-product comprising the steps of (i) contacting a first stream comprising an alkylaromatic compound with a second stream comprising an oxygen-containing gas in the presence of a first catalyst comprising a cyclic imide under conditions to convert at least a portion of said alkylaromatic compound to an alkylaromatic hydroperoxide, (ii) producing an effluent stream comprising said cyclic imide, said alkylaromatic hydroperoxide, and said alkylaromatic compound wherein said effluent stream has an alkylaromatic hydroperoxide concentration of from 10 to 40 wt %; and (iii) contacting in a second reactor at least a portion of said effluent stream with a second catalyst to convert said alkylaromatic hydroperoxide to a product stream comprising phenol and said co-product.Type: ApplicationFiled: January 25, 2010Publication date: December 8, 2011Inventors: Kun Wang, Francisco M. Benitez, James R. Lattner, Jihad M. Dakka, Edmund J. Mozeleski, Stephen Zushma
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Patent number: 8030525Abstract: 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: GrantFiled: October 13, 2009Date of Patent: October 4, 2011Assignee: 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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Patent number: 8017822Abstract: 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: GrantFiled: October 5, 2009Date of Patent: September 13, 2011Assignee: Shell Oil CompanyInventors: Howard Lam Ho Fong, Richard Dale Swain
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Publication number: 20110218366Abstract: The invention relates to a process for the alkylation of benzene with isopropanol (IPA) as alkylating agent, or blends of isopropanol and propylene, which comprises effecting said reaction completely in gaseous phase and in the presence of a catalytic system containing a zeolite belonging to the MTW family.Type: ApplicationFiled: September 7, 2009Publication date: September 8, 2011Applicant: POLIMERI EUROPA S.P.A.Inventors: Loreno Lorenzoni, Paolo Calaresu, Pier Gianni Cabras
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Patent number: 8003827Abstract: 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: GrantFiled: April 15, 2009Date of Patent: August 23, 2011Assignee: 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: 20110201846Abstract: It is an object of the present invention to provide a method for producing an alkylated aromatic compound and a method for producing cumene that can greatly reduce the amount of solid acid substance, and a method for producing phenol including a step of producing cumene by the method for producing cumene.Type: ApplicationFiled: October 22, 2009Publication date: August 18, 2011Applicant: MITSUI CHEMICALS, INC.Inventors: Kenji Fujiwara, Tsuneyuki Ohkubo, Terunori Fujita, Shinobu Aoki, Masayasu Ishibashi, Masao Imai, Kozo Yasuda
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Publication number: 20110190546Abstract: 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: ApplicationFiled: July 14, 2009Publication date: August 4, 2011Inventors: Jihad M. Dakka, Kun Wang, Edmund J. Mozeleski, Stephen Zushma
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Patent number: 7985883Abstract: 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: GrantFiled: July 8, 2008Date of Patent: July 26, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: James C. Vartuli, Jihad M. Dakka, Robert C. Lemon
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Publication number: 20110172466Abstract: In a process for oxidizing a hydrocarbon to the corresponding hydroperoxide, alcohol, ketone, carboxylic acid or dicarboxylic acid, a reaction medium comprising a hydrocarbon is contacted with an oxygen-containing gas in a reaction zone and in the presence of a catalyst comprising a cyclic imide. During the oxidation process, a portion of the reaction medium is continuously or intermittently removed from the reaction zone, is stripped of water and organic acid impurities and then returned to the reaction zone.Type: ApplicationFiled: August 17, 2009Publication date: July 14, 2011Applicant: EXXONMOBIL CHEMICAL PATENTS INC.Inventors: James R. Lattner, Mark Hagemeister, Jon E.R. Stanat, John S. Buchanan, Jihad M. Dakka, Stephen Zushma
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Publication number: 20110152577Abstract: In a process for producing sec-butylbenzene, a C4 olefinic hydrocarbon feedstock comprising isobutene and at least one n-butene is contacted with methanol and/or water in the presence of an acid catalyst to selectively oxygenate isobutene to produce an effluent stream rich in n-butene and containing less isobutene than the feedstock. The effluent stream is then contacted with benzene under alkylation conditions and in the presence of an alkylation catalyst to produce alkylation stream comprising sec-butylbenzene.Type: ApplicationFiled: August 4, 2009Publication date: June 23, 2011Inventors: John S. Buchanan, Jon E.R. Stanat, James R. Lattner, Jane C. Cheng
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Patent number: 7939693Abstract: A process for producing sec-butylbenzene comprises feeding reactants comprising benzene and a C4 olefin to a distillation column reactor having a first reaction zone containing an alkylation catalyst and a second distillation zone, which is located below said first reaction zone and which is substantially free of alkylation catalyst, wherein the ratio of the number of distillation stages in said first reaction zone to the number of distillation stages in said second distillation zone is less than 1:1. Concurrently in the distillation reactor, the reactants are contacted with the alkylation catalyst in the first reaction zone under conditions such that the C4 olefin reacts with the benzene to produce sec-butylbenzene and the sec-butylbenzene is fractioned from the unreacted C4 olefin. The sec-butylbenzene thereby passes as a liquid phase stream from the first reaction zone to the second distillation zone and the liquid phase steam is withdrawn from the distillation column reactor as bottoms.Type: GrantFiled: July 11, 2008Date of Patent: May 10, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jane C. Cheng, Jihad M. Dakka, Travis A. Reine, Jon E. Stanat
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Publication number: 20110105805Abstract: In a process for producing phenol, cyclohexylbenzene is oxidized to produce cyclohexylbenzene hydroperoxide and then the resultant cyclohexylbenzene hydroperoxide is cleaved to produce an effluent stream comprising phenol and cyclohexanone. At least a portion of the effluent stream is then fed to at least one dehydrogenation reaction zone, where the effluent stream portion is contacted with a dehydrogenation catalyst under conditions effective to convert at least part of the cyclohexanone in the effluent portion into phenol and hydrogen.Type: ApplicationFiled: July 14, 2009Publication date: May 5, 2011Inventors: John S. Buchanan, Jon E. Stanat, Tan-Jen Chen, Jihad M. Dakka, James R. Lattner
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Publication number: 20110098509Abstract: The invention relates to a process for the preparation of phenol which comprises the aerobic oxidation of cumene to hydroperoxide with high conversions and selectivities, in the presence of new catalytic systems, extremely mild conditions and the subsequent acid decomposition of the hydroperoxide to phenol and acetone.Type: ApplicationFiled: September 20, 2007Publication date: April 28, 2011Applicant: POLIMERI EUROPA S.p.A.Inventors: Francesco Minisci, Ombretta Porta, Angelo Clerici, Alberto Clerici, Francesco Recupero, Carlo Punta, Cristian Gambarotti, Monica Pierini
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Publication number: 20110092742Abstract: In a process for producing alkylbenzene hydroperoxides, a feed comprising (i) sec-butylbenzene, (ii) cumene in an amount greater than 10 wt % of the total feed and (iii) at least one of iso-butylbenzene and tert-butylbenzene in an amount up to 20 wt % of the total feed is contacted with an oxygen-containing gas in the presence of a catalyst comprising a cyclic imide of the general formula (I): wherein each of R1 and R2 is independently selected from hydrocarbyl and substituted hydrocarbyl radicals having 1 to 20 carbon atoms, or from the groups SO3H, NH2, OH, and NO2 or from the atoms H, F, Cl, Br, and I, provided that R1 and R2 can be linked to one another via a covalent bond; each of Q1 and Q2 is independently selected from C, CH, N and CR3; each of X and Z is independently selected from C, S, CH2, N, P and elements of Group 4 of the Periodic Table; Y is O or OH; k is 0, 1, or 2; l is 0, 1, or 2; m is 1 to 3; and R3 can be any of the entities listed for R1.Type: ApplicationFiled: July 14, 2009Publication date: April 21, 2011Inventors: Jihad M. Dakka, Stephen Zushma
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Publication number: 20110092745Abstract: The invention provides an efficient process for producing alkylated aromatic compounds by directly reacting an aromatic compound with a ketone and hydrogen in a compact reactor. The invention further provides a process for producing phenol which includes a step of producing cumene by the above alkylation process. The process for producing alkylated aromatic compounds includes feeding raw materials including an aromatic compound, a ketone and hydrogen in a gas-liquid downward concurrent flow mode to a fixed-bed reactor packed with a catalyst thereby to produce an alkylated aromatic compound, wherein the catalyst includes a solid acid component and a metal component, the catalyst is loaded in the fixed-bed reactor such that the catalyst forms a catalyst layer, and the reaction gas flow rate defined by Equation (1) below is not less than 0.Type: ApplicationFiled: June 3, 2009Publication date: April 21, 2011Applicant: MITSUI CHEMICALS, INC.Inventors: Shinji Senoo, Kazuhiko Kato, Kenji Doi, Katsunari Higashi
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Publication number: 20110087053Abstract: The invention provides an efficient process for producing alkylated aromatic compounds such as cumene in a compact reactor. The invention also provides a process for producing phenol which includes a step of producing cumene by the above process. The process for producing alkylated aromatic compounds of the invention includes feeding raw materials including an aromatic compound and an alcohol in a gas-liquid downward concurrent flow mode to a fixed-bed reactor packed with a solid acid catalyst thereby to produce an alkylated aromatic compound, wherein the raw materials are fed to the reactor in a stream of a gas, and the reaction gas flow rate defined by the equation below is not less than 0.05 at an entrance of a solid acid catalyst layer: ?g·ug·[?air·?water/(?g·?l)]1/2(kgm?2s?1).Type: ApplicationFiled: June 3, 2009Publication date: April 14, 2011Applicant: MITSUI CHEMICALS, INC.Inventors: Shinji Senoo, Kazuhiko Kato, Kenji Doi, Katsunari Higashi
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Patent number: 7910779Abstract: 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: October 14, 2010Date of Patent: March 22, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Tan-Jen Chen, Jane C. Cheng, Terry E. Helton, John Scott Buchanan
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Patent number: 7910778Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted with a catalyst under hydroalkylation conditions to produce an effluent containing cyclohexylbenzene. The catalyst comprises a composite of a molecular sieve, an inorganic oxide different from said molecular sieve and at least one hydrogenation metal, wherein at least 50 wt % of said hydrogenation metal is supported on the inorganic oxide.Type: GrantFiled: July 11, 2008Date of Patent: March 22, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Tan-Jen Chen, John Scott Buchanan, Jane Chi-ya Cheng, Terry E. Helton
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Patent number: 7906685Abstract: 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: GrantFiled: August 12, 2008Date of Patent: March 15, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Tan-Jen Chen, Francisco M. Benitez, Jane C. Cheng, Jon E. Stanat, John Scott Buchanan
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Patent number: 7888537Abstract: 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: GrantFiled: December 19, 2007Date of Patent: February 15, 2011Assignee: UOP LLCInventors: Robert J. Schmidt, Deng-Yang Jan, Raelynn M. Miller, James A. Johnson
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Patent number: 7858832Abstract: A process for producing sec-butylbenzene comprises contacting a feed comprising benzene and a C4 alkylating agent under alkylation conditions comprising a temperature of about 110° C. to about 150° C. with a catalyst comprising at least one 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. The sec-butylbenzene can be then oxidized to produce a hydroperoxide and the hydroperoxide decomposed to produce phenol and methyl ethyl ketone.Type: GrantFiled: February 8, 2007Date of Patent: December 28, 2010Assignee: ExxonMobil Chemical Patents Inc.Inventors: Jane C. Cheng, John S. Buchanan, Jon E. Stanat, Christine N. Elia, Jihad M. Dakka