Preparing By Cleavage Of Hydroperoxide Or Other Peroxide Patents (Class 568/768)
  • Patent number: 9133088
    Abstract: The invention relates to a process for hydroxylating phenolic substrates such as phenols or phenol ethers. The process comprises reacting the phenolic substrate and hydrogen peroxide in the presence of a catalyst in a reaction mixture; and simultaneously removing water from the reaction mixture. The process improves the reaction rate, yield, and product selectivities.
    Type: Grant
    Filed: February 19, 2015
    Date of Patent: September 15, 2015
    Inventor: Yuan-zhang Han
  • Patent number: 9035106
    Abstract: The present invention relates to a method for the hydroxylation of phenols and phenol ethers by means of hydrogen peroxide. The invention specifically relates to a method for the hydroxylation of phenol by means of the hydrogen peroxide. The method of the invention for the hydroxylation of a phenol or phenol ether by means of reacting said phenol or phenol ether with the hydrogen peroxide in the presence of an acid catalyst is characterized in that it includes mixing a phenol or phenol ether with a hydrogen peroxide solution in a mixing device under conditions enabling the conversion rate of the hydrogen peroxide to be minimized, and in that said reaction mixture is then placed in a piston flow reactor where the reaction leading to the production of the hydroxylated material takes place, the acid catalyst being fed into the mixing device and/or into the piston flow reactor.
    Type: Grant
    Filed: February 15, 2012
    Date of Patent: May 19, 2015
    Assignee: RHODIA OPERATIONS
    Inventors: Laurent Garel, Jean-Christophe Bigouraux, Stéphanie Normand, Pascal Pitiot
  • Patent number: 8946488
    Abstract: A method for hydroxylating phenols and phenol ethers using hydrogen peroxide and specifically, a method for hydroxylating phenol using hydrogen peroxide. The method for hydroxylating a phenolic substrate selected from a phenol or a phenol ether by reacting such phenolic substrate with hydrogen peroxide in the presence of an acid catalyst comprises the following steps, implemented consecutively or simultaneously: a first step consisting of mixing a phenolic substrate with a hydrogen peroxide solution under conditions in which the temperature is sufficient for the initial phenolic substrate to remain liquid and for minimizing the conversion rate of the hydrogen peroxide; a second step consisting of carrying out the phenolic substrate hydroxylation reaction under adiabatic conditions, the acid catalyst being added at the mixing stage and/or at the beginning of the hydroxylation reaction; and a third step, if necessary, consisting of recovering the hydroxylated product.
    Type: Grant
    Filed: May 15, 2012
    Date of Patent: February 3, 2015
    Assignee: Rhodia Operations
    Inventors: Laurent Garel, Stéphanie Normand, Pascal Pitiot, Jean-Christophe Bigouraux
  • Patent number: 8946484
    Abstract: In a process for producing phenol and cyclohexanone a feed comprising cyclohexylbenzene hydroperoxide and water in an amount from 1 to 15,000 ppm, based upon total weight of feed, is contacted with a cleavage catalyst comprising an aluminosilicate of the FAU type under cleavage conditions effective to convert at least a portion of the cyclohexylbenzene hydroperoxide into phenol and cyclohexanone.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: February 3, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Kun Wang, Roberto Garcia
  • Patent number: 8791308
    Abstract: A process for the hydroxylation of phenols and of phenol ethers by hydrogen peroxide is described. More particularly a process for the hydroxylation of phenol by hydrogen peroxide is described. The described process can include hydroxylation of a phenol or of a phenol ether having at least one hydrogen atom at the ortho and para position of the hydroxyl group or of the ether group, by reaction of said phenol or phenol ether, with hydrogen peroxide, in the presence of an acid catalyst, wherein the reaction is carried out in the presence of an effective amount of a catalyst which is a mixture of at least two strong acids and wherein one of the acids is chosen from strong protonic acids and the other acid is chosen from superacids.
    Type: Grant
    Filed: March 30, 2010
    Date of Patent: July 29, 2014
    Assignee: Rhodia Operations
    Inventor: Laurent Garel
  • Publication number: 20140100392
    Abstract: A method for hydroxylation of phenol is disclosed. The method includes the step of performing a reaction of phenol and hydrogen peroxide to form diphenol in the presence of solid catalyst with zeolite framework, wherein the solid catalyst includes silicon oxide, titanium oxide and cobalt oxide. The solid catalyst used in the preparation of diphenol of the present invention has high conversion rate of diphenol, selectivity of diphenol and higher utilization rate of hydrogen peroxide without using high concentration of hydrogen peroxide.
    Type: Application
    Filed: October 2, 2013
    Publication date: April 10, 2014
    Applicant: China Petrochemical Development Corporation, Taipei (Taiwan)
    Inventors: I-Hui Lin, Cheng-Fa Hsieh, Pin-To Yao
  • Patent number: 8680355
    Abstract: A novel olefin production process of the invention can be established as an industrial and practical process of producing an olefin with high selectivity by directly reacting a ketone and hydrogen in a single reaction step. In particular, a novel olefin production process is provided in which propylene is obtained with high selectivity by directly reacting acetone and hydrogen. An olefin production process of the invention includes reacting a ketone and hydrogen at a reaction temperature in the range of 50 to 300° C. in the presence of a Cu-containing hydrogenation catalyst and a solid acid substance.
    Type: Grant
    Filed: October 22, 2009
    Date of Patent: March 25, 2014
    Assignee: Mitsui Chemcials, Inc.
    Inventors: Tsuneyuki Ohkubo, Kenji Fujiwara, Terunori Fujita
  • Publication number: 20140073818
    Abstract: A method for hydroxylating phenols and phenol ethers using hydrogen peroxide and specifically, a method for hydroxylating phenol using hydrogen peroxide. The method for hydroxylating a phenolic substrate selected from a phenol or a phenol ether by reacting such phenolic substrate with hydrogen peroxide in the presence of an acid catalyst comprises the following steps, implemented consecutively or simultaneously: a first step consisting of mixing a phenolic substrate with a hydrogen peroxide solution under conditions in which the temperature is sufficient for the initial phenolic substrate to remain liquid and for minimizing the conversion rate of the hydrogen peroxide; a second step consisting of carrying out the phenolic substrate hydroxylation reaction under adiabatic conditions, the acid catalyst being added at the mixing stage and/or at the beginning of the hydroxylation reaction; and a third step, if necessary, consisting of recovering the hydroxylated product.
    Type: Application
    Filed: May 15, 2012
    Publication date: March 13, 2014
    Applicant: RHODIA OPERATIONS
    Inventors: Laurent Garel, Stephanie Normand, Pascal Pitiot, Jean-Christophe Bigouraux
  • Patent number: 8658835
    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. The contacting produces an effluent comprising an oxidized hydrocarbon product and unreacted imide catalyst and the effluent is treated with at least one solid sorbent to remove at least part of the unreacted imide catalyst and produce a treated effluent comprising said oxidized hydrocarbon product. The organic phase can then be recovered.
    Type: Grant
    Filed: July 13, 2010
    Date of Patent: February 25, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Kun Wang, Jihad M. Dakka, Stephen Zushma
  • Patent number: 8598388
    Abstract: Process for the preparation of phenol and cyclohexanone which comprises: a. the synthesis of cyclohexylbenzene by the hydro-alkylation of benzene by contact with hydrogen or the alkylation of benzene with cyclohexene using Y zeolites; b. the selective aerobic oxidation of cyclohexylbenzene to the corresponding hydroperoxide catalyzed by N-hydroxy-derivatives in the presence of polar solvents; and c. the scission of the hydroperoxide of cyclohexylbenzene to phenol and cyclohexanone by homogeneous or heterogeneous acid catalysts; characterized in that the synthesis of cyclohexylbenzene takes place in the presence of a catalytic system comprising a Y zeolite and an inorganic ligand wherein the Y zeolite has a crystalline structure with openings consisting of 12 tetrahedra and the inorganic ligand is ?-alumina, and wherein said catalytic composition is characterized by a pore volume, obtained by adding the mesoporosity and macroporosity fractions, greater than or equal to 0.
    Type: Grant
    Filed: June 23, 2010
    Date of Patent: December 3, 2013
    Assignee: Polimeri Europa S.p.A.
    Inventors: Elena Bencini, Cristian Gambarotti, Lucio Melone, Nadia Pastori, Simona Prosperini, Carlo Punta, Francesco Recupero
  • Patent number: 8487138
    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: Grant
    Filed: July 11, 2008
    Date of Patent: July 16, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad M. Dakka, James C. Vartuli, Stephen Zushma
  • Patent number: 8440864
    Abstract: 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: Grant
    Filed: August 4, 2009
    Date of Patent: May 14, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: John S. Buchanan, Jon E. R. Stanat, James R. Lattner, Jane C. Cheng
  • Patent number: 8436213
    Abstract: 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: Grant
    Filed: August 4, 2009
    Date of Patent: May 7, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad M. Dakka, Jane C. Cheng, John S. Buchanan
  • Publication number: 20110152579
    Abstract: The subject of the present invention is a method for the hydroxylation of phenol by hydrogen peroxide. The method of the invention for the hydroxylation of phenol to pyrocatechol and hydroquinone in a pyrocatechol/hydroquinone ratio between 1.7 and 2.3, by reaction of the phenol with hydrogen peroxide, in the presence of a catalyst, is characterized by the fact that the reaction is carried out in the presence of an effective amount of a hydroxyaromatic sulfonic acid.
    Type: Application
    Filed: June 8, 2009
    Publication date: June 23, 2011
    Inventor: Laurent Garel
  • Patent number: 7858832
    Abstract: 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: Grant
    Filed: February 8, 2007
    Date of Patent: December 28, 2010
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jane C. Cheng, John S. Buchanan, Jon E. Stanat, Christine N. Elia, Jihad M. Dakka
  • 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: 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
  • Patent number: 7326815
    Abstract: The present invention relates to a process for producing phenol and a ketone of general formula R1COCH2R3 (I), in which R1 and R2 each independently represent an alkyl group having from 1 to 4 carbon atoms, said process comprising: (a) providing an alkylbenzene feedstock comprising (i) an alkylbenzene of general formula (II) in which R1 and R2 have the same meaning as in formula (I) and (ii) at least one structural isomer of said alkylbenzene of formula (II) in an amount of at least 0.
    Type: Grant
    Filed: December 27, 2005
    Date of Patent: February 5, 2008
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad Mohammed Dakka, Doron Levin, Jon Edmond Randolph Stanat
  • Publication number: 20070197839
    Abstract: A process for producing a phenol, which comprises the following steps of: (1) oxidizing an alkylbenzene with an oxygen-containing gas to obtain an oxidation reaction mixture containing a hydroperoxide; (2) subjecting the oxidation reaction mixture to extraction operation with an alkaline aqueous solution to obtain an extract containing the hydroperoxide; (3) subjecting the extract obtained in the step (2) to extraction operation with an organic solvent to obtain an extract containing the hydroperoxide; (4) subjecting the extract obtained in the step (3) to water washing to obtain an oil layer containing the hydroperoxide, in which a content of the alkali has been reduced; and (5) subjecting the hydroperoxide contained in the oil layer obtained in the water washing step (4) to acidolysis to obtain a phenol, wherein a concentration of the hydroperoxide to be subjected to the water washing in the step (4), is 20% by weight or less.
    Type: Application
    Filed: February 15, 2007
    Publication date: August 23, 2007
    Applicant: SUMITOMO CHEMICAL CO., LTD.
    Inventor: Tomoyuki Noritake
  • Publication number: 20070197838
    Abstract: A process for simultaneously producing a dihydroxybenzene and a diisopropylbenzene dicarbinol, which contains subjecting a diisopropylbenzene with an oxygen containing gas to obtain an oxidation reaction mixture containing a diisopropylbenzene dihydroperoxide and a diisopropylbenzene hydroxy hydroperoxide followed by an extraction separation step, a decomposition step, a distillation separation step, a reduction step and a post-treatment step in this order, the process containing purifying the diisopropylbenzene dicarbinol from the liquid containing the diisopropylbenzene dicarbinol obtained in the reduction step through purification operations containing crystallization, filtration and subsequent drying, and supplying a filtrate obtained by the filtration to the decomposition step and/or distillation separation step.
    Type: Application
    Filed: February 12, 2007
    Publication date: August 23, 2007
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Mamoru SEINO
  • Patent number: 7166752
    Abstract: A process for decomposing a cumene oxidation product mixture containing cumene hydroperoxide (CHP) and dimethylphenyl carbinol (DMPC) to produce phenol, acetone and alpha-methyl styrene (AMS) with enhanced safety of operation and reduced by-product formation which comprises the steps: mixing the cumene oxidation product in a stirred or back-mixed reactor with an acid catalyst, with 10 to 100 percent acetone relative to the amount of acetone produced during the decomposition reaction, and with up to 4 weight percent additional amounts of water relative to the reaction mixture, at an average temperature between about 50° C. and about 90° C. for a time sufficient to lower the average CHP concentration of the reactor to between about 0.2 and about 3.0 weight percent, and wherein a portion of DMPC is converted to dicumyl peroxide (DCP); then reacting the reaction mixture from step (a) at a temperature between about 120° C. and 150° C.
    Type: Grant
    Filed: July 19, 2002
    Date of Patent: January 23, 2007
    Assignee: Sunoco, Inc. (R&M)
    Inventors: Bernard K. Marshall, Jr., Anthony J. DeCaria, Richard R. Hertzog, Stylianos Sifniades, William B. Fisher
  • Patent number: 6965056
    Abstract: There is provided a process for the manufacture of phenolic compounds by separating a neutralized aralkyl hydroperoxide cleavage mass stream containing salts of neutralization into a crude ketone stream and a crude phenolic stream containing the salts of neutralization; separating the crude phenolic stream into a concentrated phenolic-rich stream, enriched in phenolic compounds, and a crude phenolic bottoms stream enriched in tars and alpha methyl styrene dimers, each compared to the crude phenolic stream, said crude phenolic bottoms stream containing salts of neutralization; to the crude phenolic bottoms stream, adding water and a diluent composition, thereby forming a phase separable crude phenolic bottoms stream, said diluent composition comprised of hydrocarbons phase compatible with the crude phenolic bottoms stream and having a combined density lower than the density of the crude phenolic bottoms stream; separating the separable crude phenolic bottoms stream into a hydrocarbon phase and an aqueous phase
    Type: Grant
    Filed: May 3, 1999
    Date of Patent: November 15, 2005
    Assignee: Shell Oil Company
    Inventors: Austin Dale Taggart, II, Edgar Donald Allan, Roberto Carlos Longoria, David Werner Daum, Robert Lawrence Blackbourn
  • Patent number: 6960698
    Abstract: A method for treating tar separated from a liquid containing an aromatic hydroxybenzene obtained by acidolysis of a liquid containing an aromatic hydroperoxide, which comprises dissolving the tar with an alkaline aqueous solution.
    Type: Grant
    Filed: March 20, 2003
    Date of Patent: November 1, 2005
    Assignee: Sumitomo Chemical Compnay, Limted
    Inventors: Mamoru Seino, Shigefumi Tokumasu
  • Patent number: 6852893
    Abstract: The invention relates to a method for oxidizing substrates such as hydrocarbons, waxes or soot. The method involves the use of a compound of formula (I) in which: R1 and R2 represent H, an aliphatic or aromatic alkoxy radical, carboxyl radical, alkoxycarbonyl radical or hydrocarbon radical, each having 1 to 20 hydrocarbon atoms, SO3H, NH2, OH, F, Cl, Br, I and/or NO2, whereby R1 and R2 designate identical or different radicals or R1 and R2 can be linked to one another via a covalent bonding; Q1 and Q2 represent C, CH, N, CR5, each being the same or different; X and Z represent C, S, CH2, each being the same or different; Y represents O and OH; k=0, 1, 2; l=0, 1, 2; m=1 to 3, and; R5 represents one of the meanings of R1. Said compound is used as a catalyst in the presence of a radical initiator, whereby the molar ratio of the catalyst to the hydrocarbon is less than 10 mol %. Peroxy compounds or azo compounds can be used as the radical initiator. Preferred substrates are aliphatic or aromatic hydrocarbons.
    Type: Grant
    Filed: March 22, 2001
    Date of Patent: February 8, 2005
    Assignee: Creavis Gesellschaft fuer Technologie and Innovation mbH
    Inventors: Adolf Kühnle, Mark Duda, Carsten Jost, Guido Fries, Jochen Kirchhoff, Thomas Schiffer, Roger Arthur Sheldon, Sasidharan Manickam, Isabella W. C. E. Arends
  • 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: 20040162446
    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: Application
    Filed: January 21, 2004
    Publication date: August 19, 2004
    Inventor: Jesse Raymond Black
  • Publication number: 20040116749
    Abstract: A process is disclosed for producing &agr;-methylstyrene, acetone, and phenol wherein the amount of &agr;-methylstyrene produced may be controlled by selectively converting a portion of the cumene hydroperoxide to dimethyl phenyl carbinol, the hydrated form of &agr;-methylstyrene. The dimethyl phenyl carbinol thus produced will lead to increased production of &agr;-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 &agr;-methylstyrene produced in the plant can be continuously set to meet the demand of the market for &agr;-methylstyrene. Also disclosed is a non-acidic catalyst for reduction of cumene hydroperoxide.
    Type: Application
    Filed: December 16, 2002
    Publication date: June 17, 2004
    Inventors: Doron Levin, C. Morris Smith, Jose Guadalupe Santiesteban, James C. Vartuli
  • Publication number: 20040106831
    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: Application
    Filed: September 11, 2003
    Publication date: June 3, 2004
    Inventors: Theodor Robert Wilks, Mark Thornton Vandersall, William Frederick Rogers
  • Patent number: 6720462
    Abstract: The invention relates to a process for preparing phenol derivatives by catalytic oxidation of an aromatic hydrocarbon to the hydroperoxide and subsequent cleavage of the hydroperoxide to give the phenol derivative and a ketone, wherein a compound of the formula I where R1, R2=H, aliphatic or aromatic alkoxy radical, carboxyl radical, alkoxycarbonyl radical or hydrocarbon radical, in each case having from 1 to 20 carbon atoms, SO3H, NH2, OH, F, Cl, Br, I and/or NO2, where R1 and R2 are identical or different radicals or R1 and R2 may be joined to one another via a covalent bond, and X, Z=C, S, CH2 Y=O, OH k=0, 1, 2 l=0, 1, 2 m=1-3; is used as oxidation catalyst in the presence of a free-radical initiator, where the molar ratio of the catalyst to the aromatic hydrocarbon is less than 10 mol %.
    Type: Grant
    Filed: September 26, 2002
    Date of Patent: April 13, 2004
    Assignee: Degussa AG
    Inventors: Adolf Kuhnle, Mark Duda, Uwe Tanger, Roger Arthur Sheldon, Sasidharan Manickam, Isabella W. C. E. Arends
  • 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.
  • Publication number: 20030083527
    Abstract: The invention relates to a process for preparing phenol derivatives by catalytic oxidation of an aromatic hydrocarbon to the hydroperoxide and subsequent cleavage of the hydroperoxide to give the phenol derivative and a ketone, wherein a compound of the formula I 1
    Type: Application
    Filed: September 26, 2002
    Publication date: May 1, 2003
    Inventors: Adolf Kuhnle, Mark Duda, Uwe Tanger, Roger Arthur Sheldon, Sasidharan Manickam, Isabella W.C.E. Arends
  • Patent number: 6486365
    Abstract: A process for converting carbonyl-type impurities contained in a phenolic solvent to high-boiling derivatives is provided by contacting the phenolic solvent with a hydrotalcite-type material (HTM). The phenol can be separated from the high-boiling derivatives using conventional separation techniques, such as distillation, so the invention also provides a process for separating carbonyl-type impurities, such as hydroxyacetone (HA), from a phenolic solvent. The process can be applied in the conventional industrial process for converting cumene to phenol to remove carbonyl-type impurities 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 an HTM to produce phenol and high-boiling derivatives.
    Type: Grant
    Filed: April 4, 2002
    Date of Patent: November 26, 2002
    Assignee: General Electric Company
    Inventors: John W. Fulmer, Bharat Singh, Pramod Kumbhar, Prashant Anil Tatake, Umesh Hasyagar
  • Patent number: 6452056
    Abstract: A fluorine-containing benzonitrile derivative (formula 1) is subjected to a reduction reaction to obtain a fluorine-containing benzylamine derivative (formula 2), and the amino group in said fluorine-containing benzylamine derivative is replaced with a hydroxyl group to obtain a fluorine-containing benzyl alcohol derivative (formula 3): wherein X is a halogen atom, when m is an integer of 2 or more, each X may be the same or different, and m is an integer of from 0 to 4.
    Type: Grant
    Filed: February 20, 2001
    Date of Patent: September 17, 2002
    Assignee: Asahi Glass Company, Limited
    Inventors: Tsuneo Kawanobe, Osamu Takazawa, Keisuke Yoshikawa, Hiroyuki Watanabe
  • Patent number: 6433232
    Abstract: A process for producing a hydroxyaromatic compound by oxidizing an alkyl group-substituted aromatic hydrocarbon to a hydroperoxyaromatic compound and decomposing the hydroperoxyaromatic compound to the hydroxyaromatic compound in which the step of neutralizing the reaction mixture containing the hydroxyaromatic compound with an aqueous alkali solution is conducted so that an aqueous layer, which is obtained by mixing an oil layer of the neutralized mixture and deionized water in a volume ratio of the oil layer to the deionized water of 2:1 to obtain an oil/water mixture and allowing the oil/water mixture to stand still, may have a pH falling within the range of from 4.5 to 5.5, improves the yield of the hydroxyaromatic compound product while suppressing by-production of heavy substances.
    Type: Grant
    Filed: February 12, 2001
    Date of Patent: August 13, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Tomoyuki Noritake
  • Patent number: 6410804
    Abstract: A process for producing phenol and acetone from cumene hydroperoxide comprises: i) introducing a cumene hydroperoxide feed into a reactive distillation column comprising at its upper portion a distillation column and at its lower portion a catalyst bed, at a point above said catalyst bed; ii) mixing a diluting portion of acetone with said cumene hydroperoxide to provide a diluted cumene hydroperoxide; iii) directing said diluted cumene hydroperoxide through said catalyst bed under conditions sufficient to effect the exothermic decomposition of said cumene hydroperoxide to a product comprising a heavy fraction comprising phenol and a vaporized light fraction comprising acetone; iv) withdrawing said heavy fraction as bottoms from said column; v) flowing said vaporized light fraction upwards through the catalyst bed and at least a portion of the reactive distillation column; vi) condensing said light fraction to provide at least a portion of said diluting portion of acetone for subsequent mixing with said
    Type: Grant
    Filed: December 21, 1999
    Date of Patent: June 25, 2002
    Assignee: Exxon Mobil Oil Corporation
    Inventors: Doron Levin, Jose G. Santiesteban
  • Publication number: 20020058845
    Abstract: A process for producing phenol and acetone from cumene hydroperoxide comprises:
    Type: Application
    Filed: November 14, 2001
    Publication date: May 16, 2002
    Inventors: Doron Levin, Jose G. Santiesteban
  • Publication number: 20020040165
    Abstract: A process for decomposing a cumene oxidation product mixture containing cumene hydroperoxide (CHP) and dimethylphenyl carbinol (DMPC) to produce phenol, acetone and alpha-methyl styrene (AMS) with enhanced safety of operation and reduced by-product formation which comprises the steps:
    Type: Application
    Filed: July 23, 2001
    Publication date: April 4, 2002
    Inventors: Richard R. Hertzog, Stylianos Sifniades, William Bernard Fisher
  • Patent number: 6350921
    Abstract: Improved methods for the simultaneous production of dihydroxybenzene and dicarbinol from diisopropylbenzene are provided. These methods provide for continuous and simultaneous production of diisopropylbenzene dihydroperoxide (DHP) and diisopropylbenzene hydroxyhydroperoxide (HHP) using Karr Column extractors operated in series. A very high purity DHP-containing solution, the precursor to the dihydroxybenzene, can be produced according to the reported methods. A safe and efficient method for producing dicarbinol from HHP is also disclosed.
    Type: Grant
    Filed: February 24, 1998
    Date of Patent: February 26, 2002
    Assignee: Indspec Chemical Corporation
    Inventors: Raj B. Durairaj, Vaughn J. Romell, Michael N. Tackie, Thomas K. Volek
  • Patent number: 6297406
    Abstract: A process for producing phenol and acetone from cumene hydroperoxide is described in which the cumene hydroperoxide is contacted with a solid-acid catalyst comprising a mixed oxide of cerium and a Group IVB metal.
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: October 2, 2001
    Assignee: Mobil Oil Corporation
    Inventors: Doron Levin, Jose G. Santiesteban, James C. Vartuli
  • Patent number: 6281400
    Abstract: The present invention relates to a process for preparing a microcomposite comprising a highly fluorinated ion-exchange polymer containing pendant sulfonate functional groups, said polymer existing as aggregated particles entrapped within and dispersed throughout a network of silica. Due to their high surface area and acid functionality, these microcomposites possess wide utility as improved solid acid catalysts, particularly in the substitution of aromatic compounds, in the decomposition of hydroperoxides, and in the isomerization of olefins.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: August 28, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6169215
    Abstract: A process for producing phenol and acetone from cumene hydroperoxide is described in which the cumene hydroperoxide is contacted with a solid-acid catalyst produced by calcining a source of a Group IVB metal oxide with a source of an oxyanion of a Group VIB metal at a temperature of at least 400°C.
    Type: Grant
    Filed: March 25, 1999
    Date of Patent: January 2, 2001
    Assignee: Mobil Oil Corporation
    Inventors: Doron Levin, Jose G. Santiesteban, James C. Vartuli
  • Patent number: 6169216
    Abstract: A process for producing phenol and acetone from cumene hydroperoxide is described in which the cumene hydroperoxide is contacted with a solid-acid catalyst comprising a sulfated transition metal oxide, preferably sulfated zirconia.
    Type: Grant
    Filed: April 22, 1999
    Date of Patent: January 2, 2001
    Assignee: Mobil Oil Corporation
    Inventors: Doron Levin, Jose G. Santiesteban, James C. Vartuli
  • Patent number: 5998677
    Abstract: The improved process for producing phenol, acetone and .alpha.-methylstyrene in the cumene-phenol process comprising cumene hydroperoxide, cumene and dimethylphenylcarbinol in the presence of sulfuric acid has the steps of decomposing the cumene hydroperoxide in a back mixing reactor with the yield of .alpha.-methylstyrene as produced from dimethylphenylcarbinol being controlled and the step of forming .alpha.-methylstyrene in such a way that the reaction mixture produced in the first step is supplied into a plug-flow reactor after acetone is added to said reaction mixture. The process is capable of consistent production of phenol and .alpha.-methylstyrene in high yields under mild reaction conditions.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: December 7, 1999
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Naoto Yasaka, Tatsuo Shirahata
  • Patent number: 5714641
    Abstract: Phenolic compounds, e.g., phenol, are hydroxylated, preponderantly into the para-isomer, e.g., hydroquinone, by reaction with hydrogen peroxide in the presence of an effective amount of a strong acid and a catalytically effective amount of a keto compound having the formula (II): ##STR1## in which R.sub.1 and R.sub.2, which may be identical or different, are each a hydrogen atom or an electron-donating group; n.sub.1 and n.sub.2, which may be identical or different, are numbers equal to 0, 1, 2 or 3, with the proviso that the two carbon atoms located at the .alpha.-position with respect to the two carbon atoms bearing the --CO group may be bonded together via a valence bond or via a --CH.sub.2 -- group, thereby forming a keto-containing ring member which may either be saturated or unsaturated.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: February 3, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Adrien Dromard, Michel Jouffret
  • Patent number: 5502259
    Abstract: The invention relates to a method for purification of phenol and specifically to a method for purification of phenol produced within the process of joint phenol and acetone production by cumene method.The aim of the invention is to develop a catalyst which has high activity for phenol purification from organic mico-impurities with regeneration of the catalyst and which has high mechanical strength and stability with long catalyst life.This result is obtained by phenol purification using a heterogeneous zeolite catalyst. The acidity of the catalyst measured by butane cracking (K.sub.A) is more than 10.It is preferable to use zeolites which are designated according to the classification of the International Zeolite Association by indices FAU (zeolites X, Y), MFI (for example, ZSM-5), MOR (mordenite), MAZ (omega), BEA (beta), FER (ferrierite) and others. These zeolites can be used with binders (aluminum oxide, silica gel, aluminosilicates or aluminophosphates) and without them.
    Type: Grant
    Filed: August 15, 1994
    Date of Patent: March 26, 1996
    Assignees: General Electric Company, U.S.A., Illa International
    Inventors: Vladimir M. Zakoshansky, Irina I. Vasilieva, Andrei K. Griaznov
  • Patent number: 5476968
    Abstract: A N,N'-bis(p-hydroxymethylphenyl)benzidine compound having the following formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom, a methyl group or a methoxy group; R.sub.2 represents an alkyl group having one to four carbon atoms, a methoxy group or an ethoxy group; and R.sub.3 represents a hydrogen atom or a methyl group, is intended to be used as a charge transporting material of an electrophotographic photoreceptor. A method for preparing the compound includes formylating a N,N'-diphenylbenzidine derivative having the following formula (II): ##STR2## by the conventional Viismeier reaction to obtain a N,N'-bis(p-formylphenyl) benzidine derivative of the following formula (III): ##STR3## and reducing the derivative with a boron hydride salt or an aluminum hydride salt.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: December 19, 1995
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Akira Imai, Katsumi Nukada
  • Patent number: 5475157
    Abstract: There is disclosed a process for producing an aromatic hydroxylic compound by acid decomposition of a hydroperoxide having the general formula (I) ##STR1## wherein Ar represents an aromatic hydrocarbon group having a valence of n; and n represents an integer of 1 or 2, in the presence of an acid catalyst, thereby to provide an aromatic hydroxylic compound having the general formula (II)Ar--(OH)n (II)wherein Ar and n are the same as above defined, characterized in that tetrafluoroboric acid, hexafluorosilicic acid or hexafluorophosphoric acid is used as the acid catalyst. According to this process, the aromatic hydroxylic compound is obtained in a high yield while the by-production of hydroxyacetone is effectively suppressed.
    Type: Grant
    Filed: September 2, 1994
    Date of Patent: December 12, 1995
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Shintaro Araki, Hiroshi Iwasaki, Hiroyasu Ohno, Isao Hashimoto, Teruaki Mukaiyama
  • Patent number: 5434317
    Abstract: Phenolic compounds, e.g., phenol, are hydroxylated, preponderantly into the para-isomer, e.g., hydroquinone, by reaction with hydrogen peroxide in the presence of an effective amount of a strong acid and a catalytically effective amount of a keto compound having the formula (II): ##STR1## in which R.sub.1 and R.sub.2, which may be identical or different, are each a hydrogen atom or an electron-donating group; n.sub.1 and n.sub.2, which may be identical or different, are numbers equal to 0, 1, 2 or 3, with the proviso that the two carbon atoms located at the .alpha.-position with respect to the two carbon atoms bearing the --CO group may be bonded together via a valence bond or via a --CH.sub.2 -- group, thereby forming a keto-containing ring member which may either be saturated or unsaturated.
    Type: Grant
    Filed: December 9, 1993
    Date of Patent: July 18, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Adrien Dromard, Michel Jouffret