Preparing By Cleavage Of Hydroperoxide Or Other Peroxide Patents (Class 568/798)
  • Patent number: 7847128
    Abstract: 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: Grant
    Filed: August 12, 2008
    Date of Patent: December 7, 2010
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Tan-Jen Chen, Jane C. Cheng, Terry E. Helton, John Scott Buchanan
  • Patent number: 7834218
    Abstract: 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: Grant
    Filed: February 8, 2007
    Date of Patent: November 16, 2010
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad M. Dakka, Jon E. Stanat, Francisco M. Benitez, John S. Buchanan, Jane C. Cheng, Jeffrey T. Elks
  • Patent number: 7812196
    Abstract: 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: Grant
    Filed: February 8, 2007
    Date of Patent: October 12, 2010
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad M. Dakka, Edmund J. Mozeleski, Jane C. Cheng, Francisco M. Benitez, Jon E. Stanat, John S. Buchanan
  • Patent number: 7799958
    Abstract: 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: Grant
    Filed: October 3, 2008
    Date of Patent: September 21, 2010
    Assignee: Barclays Bank PLC
    Inventors: Ralf Bonmann, Werner Pompetzki, Markus Weber
  • Patent number: 7799956
    Abstract: 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: Grant
    Filed: August 5, 2005
    Date of Patent: September 21, 2010
    Assignee: 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
  • Publication number: 20100234589
    Abstract: 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: Application
    Filed: July 11, 2008
    Publication date: September 16, 2010
    Inventors: Jihad M. Dakka, James C. Vartuli, Stephen Zushma
  • Publication number: 20100234637
    Abstract: 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: Application
    Filed: March 15, 2010
    Publication date: September 16, 2010
    Inventors: Howard Lam Ho FONG, Richard Dale Swain
  • Publication number: 20100217048
    Abstract: 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: Application
    Filed: July 8, 2008
    Publication date: August 26, 2010
    Inventors: James C. Vartuli, Jihad M. Dakka, Robert C. Lemon
  • Publication number: 20100197971
    Abstract: 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: Application
    Filed: August 12, 2008
    Publication date: August 5, 2010
    Inventors: Tan-Jen Chen, Francisco M. Benitez, Jane C. Cheng, Jon E. Stanat, John Scott Buchanan
  • Publication number: 20100179351
    Abstract: 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: Application
    Filed: August 12, 2008
    Publication date: July 15, 2010
    Inventors: Tan-Jen Chen, Jane C. Cheng, Terry E. Helton, John Scott Buchanan
  • Publication number: 20100099919
    Abstract: 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: Application
    Filed: October 13, 2009
    Publication date: April 22, 2010
    Applicant: 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
  • Publication number: 20100087686
    Abstract: 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: Application
    Filed: October 5, 2009
    Publication date: April 8, 2010
    Inventors: Howard Lam Ho FONG, Richard Dale SWAIN
  • Publication number: 20090306433
    Abstract: 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: Application
    Filed: February 8, 2007
    Publication date: December 10, 2009
    Inventors: Jihad M. Dakka, Edmund J. Mozeleski, Jane C. Cheng, Francisco M. Benitez, Jon E. Stanat, John S. Buchanan
  • Publication number: 20090264685
    Abstract: 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: Application
    Filed: April 15, 2009
    Publication date: October 22, 2009
    Applicant: SABIC Innovative Plastics IP B.V.
    Inventors: Mark E. Nelson, Arkady Samuilovich Dykman, Andrey Vladimirovich Zinenkov, Victor Vladimirovich Pinson, Ilja Nikolayevich Grebenshchikov
  • Publication number: 20090156870
    Abstract: 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: Application
    Filed: December 10, 2008
    Publication date: June 18, 2009
    Inventors: Ann Marie Lauritzen, Ajay Madhav Madgavkar
  • Publication number: 20090093656
    Abstract: 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: Application
    Filed: October 3, 2008
    Publication date: April 9, 2009
    Applicant: INEOS PHENOT GMBH & CO. KG
    Inventors: Ralf Bonmann, Werner Pompetzki, Markus Weber
  • Patent number: 7491855
    Abstract: 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: Grant
    Filed: June 4, 2003
    Date of Patent: February 17, 2009
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Pramod Shankar Kumbhar, Jegadeesh Thampi, Bharat Singh, John W. Fulmer, Prashant Anil Tatake
  • Patent number: 7485758
    Abstract: 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: Grant
    Filed: September 26, 2007
    Date of Patent: February 3, 2009
    Assignee: SABIC Innovative Plastics IP B.V.
    Inventors: Mark Nelson, Willem Lodewyk Sederel, Arkady Samuilovich Dyckman, Ilya Nikolaevich Grebenshchikov, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov
  • Patent number: 7482493
    Abstract: 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: Grant
    Filed: September 26, 2007
    Date of Patent: January 27, 2009
    Assignee: SABIC Innovative Plastics IP B.V.
    Inventors: Mark Nelson, Willem Lodewyk Sederel, Arkady Samuilovich Dyckman, Ilya Nikolaevich Grebenshchikov, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov
  • Publication number: 20080214873
    Abstract: 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: Application
    Filed: September 26, 2007
    Publication date: September 4, 2008
    Inventors: Mark Nelson, Willem Lodewyk Sederel, Arkady Samuilovich Dyckman, Ilya Nikolaevich Grebenshchikov, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov
  • Publication number: 20080214872
    Abstract: 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: Application
    Filed: September 26, 2007
    Publication date: September 4, 2008
    Inventors: Mark Nelson, Willem Lodewyk Sederel, Arkady Samuilovich Dyckman, Ilya Nikolaevich Grebenshchikov, Viktor Vladimirovich Pinson, Andrey Vladimirovich Zinenkov
  • Publication number: 20080188694
    Abstract: 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: Application
    Filed: December 19, 2007
    Publication date: August 7, 2008
    Inventors: Robert J. Schmidt, Deng-Yang Jan, Raelynn M. Miller, James A. Johnson
  • Patent number: 7396961
    Abstract: 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: Grant
    Filed: January 20, 2006
    Date of Patent: July 8, 2008
    Assignee: Rhodia Polyamide Intermediates
    Inventors: Didier Bonnet, Eric Fache, Aline Seigneurin
  • Publication number: 20080033217
    Abstract: 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: Application
    Filed: July 13, 2007
    Publication date: February 7, 2008
    Inventors: Jihad Mohammed Dakka, Doron Levin, John Scott Buchanan, Jon Edmond Randolph Stanat
  • Patent number: 7312365
    Abstract: 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: Grant
    Filed: January 21, 2004
    Date of Patent: December 25, 2007
    Assignee: Shell Oil Company
    Inventor: Jesse Raymond Black
  • Publication number: 20070244346
    Abstract: 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: Application
    Filed: April 17, 2007
    Publication date: October 18, 2007
    Applicant: INEOS Phenol GmbH & Co. KG
    Inventors: Otto Schnurr, Manfred Weber, Markus Weber
  • Patent number: 7154010
    Abstract: 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: Grant
    Filed: June 4, 2003
    Date of Patent: December 26, 2006
    Assignee: General Electric Company
    Inventors: Pramod Shankar Kumbhar, Jegadeesh Thampi, Bharat Singh, John W. Fulmer, Prashant Anil Tatake
  • Patent number: 7141701
    Abstract: A process for decomposing a cumene oxidation product mixture containing cumene hydroperoxide (CHP) and dimethylphenolcarbinol (DMPC) to produce phenol and acetone.
    Type: Grant
    Filed: August 19, 2005
    Date of Patent: November 28, 2006
    Assignee: UOP LLC
    Inventors: Robert J. Schmidt, Russell C. Schulz, Patrick J. Bullen, Constante P. Tagamolila, Steven P. Lankton, Gary A. Peterson, Michael E. Fettis
  • Patent number: 7141700
    Abstract: 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: Grant
    Filed: August 19, 2005
    Date of Patent: November 28, 2006
    Assignee: UOP LLC
    Inventors: Robert J. Schmidt, Russell C. Schulz, Patrick J. Bullen, Constante P. Tagamolila, Steven P. Lankton, Gary A. Peterson, Michael E. Fettis
  • Patent number: 7126029
    Abstract: 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: Grant
    Filed: February 2, 2004
    Date of Patent: October 24, 2006
    Assignee: Sunoco, Inc. (R&M)
    Inventors: James G. Skipworth, James M. Delabar
  • Patent number: 7109385
    Abstract: 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: Grant
    Filed: March 29, 2005
    Date of Patent: September 19, 2006
    Assignee: General Electric Company
    Inventors: Prashant Anil Tatake, Pramod Shankar Kumbhar, Bharat Singh, John William Fulmer, Sabyasachi Mandal, Arun N. Kumar, Rupesh Pawar
  • Patent number: 6984761
    Abstract: 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: Grant
    Filed: December 16, 2002
    Date of Patent: January 10, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Doron Levin, C. Morris Smith, Jose Guadalupe Santiesteban, James C. Vartuli
  • Patent number: 6939995
    Abstract: 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: Grant
    Filed: November 14, 2002
    Date of Patent: September 6, 2005
    Assignee: Shell Oil Company
    Inventors: Leslie Andrew Chewter, Wilhelmus Cornelis Nicolaas Dekker, Stephane Jean Pierre Lecrivain, Carolus Matthias Anna Maria Mesters, Andrew Neave Rogers, Lydia Singoredjo
  • Patent number: 6888035
    Abstract: 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: Grant
    Filed: September 25, 2001
    Date of Patent: May 3, 2005
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Kevin J. Fallon, Chung-Ming Chi, Henry Y. Hwang, Frank A. Demers
  • Patent number: 6875898
    Abstract: 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: Grant
    Filed: April 4, 2003
    Date of Patent: April 5, 2005
    Assignee: Ineos Phenol GmbH & Co. KG
    Inventors: Manfred Weber, Reinhard Sigg, Michael Lausmann, Siegmund Greschek
  • Patent number: 6841704
    Abstract: 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: Grant
    Filed: February 19, 2001
    Date of Patent: January 11, 2005
    Assignee: Ineos Phenol GmbH & Co. KG
    Inventors: Michael Sakuth, Uwe Tanger, Markus Weber
  • Publication number: 20040267052
    Abstract: 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: Application
    Filed: August 18, 2004
    Publication date: December 30, 2004
    Inventors: Didier Bonnet, Eric Fache, Aline Seigneurin
  • Patent number: 6825387
    Abstract: 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: Grant
    Filed: September 11, 2003
    Date of Patent: November 30, 2004
    Assignee: Kellogg Brown & Root, Inc.
    Inventors: Theodor Robert Wilks, Mark Thornton Vandersall, William Frederick Rogers, Jr.
  • Publication number: 20040236152
    Abstract: A process for producing phenol and methyl ethyl ketone (MEK).
    Type: Application
    Filed: January 21, 2004
    Publication date: November 25, 2004
    Inventors: Jesse Raymond Black, Jiemin Yang, James Laurel Buechele
  • Patent number: 6800787
    Abstract: 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: Grant
    Filed: September 30, 2003
    Date of Patent: October 5, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Mitsuru Oonuma
  • Publication number: 20040082817
    Abstract: 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: Application
    Filed: October 24, 2002
    Publication date: April 29, 2004
    Applicant: NEUROK LLC
    Inventor: Olga Tarasovna Kasaikina
  • Publication number: 20040073071
    Abstract: 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: Application
    Filed: September 30, 2003
    Publication date: April 15, 2004
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Mitsuru Oonuma
  • Publication number: 20040015021
    Abstract: A composition of an antioxidant of the formula 1
    Type: Application
    Filed: October 30, 2002
    Publication date: January 22, 2004
    Inventors: Paul E. Adams, Thomas J. Wolak
  • Patent number: 6680414
    Abstract: 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: Grant
    Filed: December 14, 2001
    Date of Patent: January 20, 2004
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Cord Knoop, Bernhard Scholz, Alfred Kaizik, Dietmar Gubisch, Joachim Schuler, Walter Tötsch, Wilfried Büschken
  • Patent number: 6630608
    Abstract: 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: Grant
    Filed: March 4, 2002
    Date of Patent: October 7, 2003
    Assignee: INEOS Phenol & GmbH Co., KG
    Inventors: Uwe Tanger, Reinhard Sigg, Siegmund Greschek, Manfred Weber
  • Publication number: 20030168329
    Abstract: 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: Application
    Filed: March 6, 2002
    Publication date: September 11, 2003
    Inventors: John W. Fulmer, Nitin Vaish, Pramod Kumbhar, Jacob L. Oberholtzer, R. Jothi Mahalingam
  • Publication number: 20030153793
    Abstract: 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: Application
    Filed: January 27, 2003
    Publication date: August 14, 2003
    Inventors: Michael Sakuth, Uwe Tanger, Markus Weber
  • Patent number: 6586640
    Abstract: 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: Grant
    Filed: June 20, 2002
    Date of Patent: July 1, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ralph Birchard Lloyd, Qun Sun, Mark Andrew Harmer, Edward George Howard, Jr.
  • Patent number: 6583326
    Abstract: 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: Grant
    Filed: October 5, 2001
    Date of Patent: June 24, 2003
    Assignee: Phenolchemie GmbH & Co. KG
    Inventors: Christoph Schwarz, Markus Weber, Uwe Tanger, Hermann-Josef Korte, Jochen Ullrich
  • Patent number: RE40668
    Abstract: 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: Grant
    Filed: October 19, 1995
    Date of Patent: March 17, 2009
    Assignees: SABIC Innovative Plastics IP B.V., ILLA International Ltd.
    Inventor: Vladimir M. Zakoshansky