Preparing By Cleavage Of Hydroperoxide Or Other Peroxide Patents (Class 568/798)
  • Patent number: 6576798
    Abstract: A system for purifying a cumene hydroperoxide cleavage product mixture comprises a cumene hydroperoxide cleavage product mixture feed containing impurities in fluid communication with an aqueous alkaline solution feed; the cumene hydroperoxide cleavage product mixture and aqueous alkaline solution feeds in fluid communication with a neutralization drum having a aqueous salt phase outlet; a aqueous salt phase feed containing impurities in fluid communication with a decomposer reactor having an oxidized aqueous salt phase outlet; an oxidizing agent feed in fluid communication with the aqueous salt phase feed containing the impurities prior to the decomposer reactor; and an oxidized aqueous salt phase feed containing water-soluble oxidized derivatives of the impurities in fluid communication with the cumene hydroperoxide cleavage product mixture prior to the neutralization drum.
    Type: Grant
    Filed: November 29, 2001
    Date of Patent: June 10, 2003
    Assignee: General Electric Company
    Inventors: Yuri Valerievich Aristovich, Valeri Yurievich Aristovich, John William Fulmer, Andrey Yurievich Sokolov, Svetlana Ananyevna Ulyanova, Sergey Nikolaevich Voyakin
  • Patent number: 6573408
    Abstract: A system for purifying a cumene hydroperoxide cleavage product mixture comprises a cumene hydroperoxide cleavage product mixture feed containing impurities in fluid communication with an aqueous alkaline solution feed; the cumene hydroperoxide cleavage product mixture and aqueous alkaline solution feeds are in fluid communication with a neutralization drum having an aqueous salt phase outlet; an aqueous salt phase feed containing impurities in fluid communication with a heat treatment vessel having a heat-treated aqueous salt phase outlet; and a heat-treated aqueous salt phase feed containing water-soluble derivatives of the impurities in fluid communication with the cumene hydroperoxide cleavage product mixture prior to the neutralization drum.
    Type: Grant
    Filed: November 29, 2001
    Date of Patent: June 3, 2003
    Assignee: General Electric Company
    Inventors: John William Fulmer, Pramod S. Kumbhar, Marakani Venkata Ramani, Bharat Singh
  • Publication number: 20030097025
    Abstract: The invention relates to a method for producing a mixture of alcohols/ketones by decomposing an alkyl hydroperoxide, particularly to a method for producing a cyclohexanol/cyclohexanone by decomposing cyclohexyl hydroperoxide in the presence of a heterogeneous catalyst. According to the invention, the reaction is carried out in the presence of a heterogeneous catalyst containing an organometallic segment fixed on the surface of a porous solid compound such as silicon. The organometallic segment ca be formula (1).
    Type: Application
    Filed: October 15, 2002
    Publication date: May 22, 2003
    Inventors: James Clark, Eric Fache, Ducan Macquarrie, Peter Price, John Rafelt
  • Publication number: 20030088129
    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: Application
    Filed: July 19, 2002
    Publication date: May 8, 2003
    Inventors: Bernard K. Marshall,, Anthony J. DeCaria, Richard R. Hertzog, Stylianos Sifniades, William B. Fisher
  • Patent number: 6555719
    Abstract: The cleavage product from the acid-catalyzed cleavage of cumene hydroperoxide into phenol and acetone is subjected to thermal after-treatment by a process, which comprises heating the cleavage product in a reactor, wherein the heat supplied for the thermal treatment is the heat generated by at least one exothermic reaction which occurs in the reactor. The exothermic reaction which proceeds in the cleavage product is preferably the cleavage of cumene hydroperoxide.
    Type: Grant
    Filed: May 3, 2001
    Date of Patent: April 29, 2003
    Assignee: Phenolchemie GmbH & Co. KG
    Inventors: Reinhard Sigg, Uwe Tanger, Manfred Weber, Otto Schnurr, Hugo H.J.M. Liefooghe
  • Publication number: 20030050513
    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: Application
    Filed: June 20, 2002
    Publication date: March 13, 2003
    Inventors: Ralph Birchard Lloyd, Qun Sun, Mark Andrew Harmer, Edward George Howard
  • Publication number: 20020183563
    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.
    Type: Application
    Filed: March 4, 2002
    Publication date: December 5, 2002
    Inventors: Uwe Tanger, Reinhard Sigg, Siegmund Greschek, Manfred Weber
  • Patent number: 6444861
    Abstract: A process for the cleavage of alkylaryl hydroperoxides includes steps for producing a mixture of a concentrate that contains at least one alkylaryl hydroperoxide to be cleaved and a cleavage product obtained from the cleavage of an alkylaryl hydroperoxide, dividing this mixture into at least two parts and cleaving the alkylaryl hydroperoxides in parallel at different temperatures. One of the two parts is treated at a temperature sufficiently high for an integrated thermal post-treatment to be achieved. The process consumes less energy since less steam has to be used. Problems which can result from fouling in heat exchangers are largely prevented. No second feed point for alkylaryl hydroperoxide has to be provided. The process can be used in the preparation of phenol and acetone by the Hock method.
    Type: Grant
    Filed: October 18, 2001
    Date of Patent: September 3, 2002
    Assignee: Phenolchemie GmbH & Co. KG
    Inventors: Uwe Tanger, Manfred Weber
  • Patent number: 6441251
    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 an inorganic, porous, crystalline material, designated as M41S, exhibiting, after calcination, an x-ray diffraction pattern with at least one peak at a d-spacing greater than about 18 Angstrom Units with a relative intensity of 100 and a benzene adsorption capacity of greater than 15 grams of benzene per 100 grams of said material at 50 torr and 25° C., wherein said material comprises sulfonate functionality.
    Type: Grant
    Filed: September 4, 2001
    Date of Patent: August 27, 2002
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Doron Levin, Jose G. Santiesteban, Lei Zhang
  • Patent number: 6441252
    Abstract: An apparatus for producing phenol and acetone from cumene hydroperoxide comprises a reactive distillation column comprising at its upper portion a distillation column and at its lower portion a catalyst bed.
    Type: Grant
    Filed: November 14, 2001
    Date of Patent: August 27, 2002
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Doron Levin, Jose G. Santiesteban
  • 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: 20020068840
    Abstract: The present invention claims a process and an apparatus for the work-up by distillation of cleavage product mixtures produced in the cleavage of alkylaryl hydroperoxides. Usually, in the work-up by distillation of cleavage product mixtures which are produced in the cleavage of alkylaryl hydroperoxides, the cleavage product mixture is divided into three main fractions, for which at least two distillation columns are used. The use of two distillation columns has the disadvantage that the capital costs, and also the energy costs, in these conventional processes are relatively high.
    Type: Application
    Filed: November 13, 2001
    Publication date: June 6, 2002
    Applicant: INEOS Phenol GMBH & CO. KG
    Inventors: Markus Weber, Christoph Schwarz, Uwe Tanger, Hermann-Josef Korte, Jochen Ullrich
  • Publication number: 20020066661
    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: Application
    Filed: October 5, 2001
    Publication date: June 6, 2002
    Applicant: PHENOLCHEMIE GMBH & CO. KG
    Inventors: Christoph Schwarz, Mark Weber, Uwe Tanger, Hermann-Josef Korte, Jochen Ullrich
  • Patent number: 6331654
    Abstract: Disclosed is a method for the production of product acetone of higher oxidation stability where the product acetone is produced by a multi-step rectification process in the presence of alkali catalyst. The embodiments of the method of present invention utilize a two-column and a one-column scheme of product acetone rectification from an acetone stream. In a two-column embodiment of the present invention, acetone is taken off in a vapor phase as a side-draw in a first column and directed to a partial condenser wherein it is separated into liquid and vapor phases with a simultaneous feed of aqueous sodium hydroxide solution to the first column above the feed tray.
    Type: Grant
    Filed: February 10, 2000
    Date of Patent: December 18, 2001
    Assignee: Illa International LLC
    Inventors: Vladimir Mikhailovitch Zakoshansky, Irina Ivanovna Vassilieva
  • Patent number: 6329553
    Abstract: A process for a combined selective thermal oxidation and photooxidation of hydrocarbons adsorbed onto zeolite matrices. A highly combined selective thermal oxidation and photooxidation of unsubstituted or alkyl substituted alkanes, alkenes, aromatics and cycloalkyls in solvent free zeolites under dark thermal conditions or under irradiation with visible light. The process oxidizes hydrocarbons almost completely selectively without substantial production of byproducts.
    Type: Grant
    Filed: November 10, 2000
    Date of Patent: December 11, 2001
    Assignee: The Regents of the University of California
    Inventors: Heinz Frei, Fritz Blatter, Hai Sun
  • Patent number: 6307112
    Abstract: Phenol and acetone are prepared by a process comprising homogeneously cleaving cumene hydroperoxide in the presence of acid catalyst in a cleavage apparatus comprising at least one reactor having plug flow characteristics thereby producing a cleavage product; recycling some of the cleavage product stream by combining the recycled cleavage product stream with the cumene hydroperoxide-containing feed stream fed to said cleavage apparatus under the condition that the mass flow ratio of the recycled partial cleavage product stream to the cumene hydroperoxide-containing feed stream sent to the cleavage reactor is less than 10.
    Type: Grant
    Filed: December 20, 1999
    Date of Patent: October 23, 2001
    Assignee: Phenolchemie GmbH & Co. KG
    Inventors: Manfred Weber, Otto Gerlich, Michael Kleine-Boymann, Werner Pompetzki, Reinhard Sigg, Christian Michalik, Jürgen Volke
  • 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: 6252124
    Abstract: A new phenol and acetone production process reduces the amount of necessary stages for obtaining phenol and acetone, results in higher yield of desired products and requires less complex equipment implementation and less energy than current processes of a similar type.
    Type: Grant
    Filed: April 29, 1999
    Date of Patent: June 26, 2001
    Assignee: ILLA International, LLC
    Inventors: Vladimir Mikhailovitch Zakoshansky, Irina Ivanovna Vassilieva
  • Patent number: 6225513
    Abstract: The present invention relates to an improved method for producing phenol and acetone by oxidizing cumene into technical cumol hydroperoxide (CHP) through catalytic cleavage of the CHP. According to the invention, the oxidation products are concentrated to up to a cumene content ranging from 21 to 30 wt % in the technical cumol hydroperoxide, said mixture being used for the catalytic cleavage.
    Type: Grant
    Filed: September 15, 1999
    Date of Patent: May 1, 2001
    Assignees: Illa International Ltd., Phenolchemie GmbH & Co. Kg
    Inventors: Vladimir Michailovitch Zakoshansky, Irina Ivanova Vasilieva, Andrei Konstantinovitch Griaznov, Youry Nikolaevitch Youriev, Heinrich Van Barnefeld, Otto Gerlich, Michael Kleine-Boymann, Werner Kleinloh, Christian Michalik
  • Patent number: 6201157
    Abstract: An improved method for production of phenol and acetone by decomposition of cumene hydroperoxide in the presence of an acidic catalyst to phenol and acetone, wherein the improvement comprises neutralization of the acidic catalyst after substantial completion of the decomposition by addition of a substituted amine.
    Type: Grant
    Filed: January 10, 2000
    Date of Patent: March 13, 2001
    Assignee: Sunoco, Inc. (R&M)
    Inventor: Scott R. Keenan
  • 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: 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: 6107527
    Abstract: The process for the production of hydroxy aromatic substances by means of catalytic oxidation of isoalkyl aromatic substance with oxygen, and decomposition of the hydroperoxide thus formed, is based on the concept that isoalkylaromatic substances are emulsified with an aqueous catalyst solution and brought to a temperature ranging from 50.degree. C. up to the boiling temperature of the emulsion; thereupon the oxygen is allowed to act for 2 to 20 hours and the hydroperoxide formed decomposed, in the presence of an inorganic acid as catalyst, into an hydroxyaromatic substance and a ketone.
    Type: Grant
    Filed: March 19, 1997
    Date of Patent: August 22, 2000
    Assignee: Rutgers Kureha Solvents GmbH
    Inventors: Zbigniew Stec, Jan Zawadiak, Ulrich Knips, Robert Zellerhoff, Danuta Gilner, Beata Orlinska, Jerzy Polaczek, Witold Tecza, Zofia Machowska
  • Patent number: 6066767
    Abstract: Purification of cumene hydroperoxide cleavage products from hydroxyacetone and carbonyl compounds is accomplished via extraction of hydroxyacetone and carbonyl compounds from cleavage products with a circulating water-salt solution in an extractor during an extraction stage and subsequent conversion of hydroxyacetone and other carbonyl compounds into deep condensation products in a HAC reactor operating as a plug-flow reactor or mixing reactor or as their combination. The conversion/condensation process is conducted in the water-salt solution by treating the hydroxyacetone and carbonyl compounds with alkaline agents. Various homogenous and/or heterogeneous alkaline catalysts may be used. Optionally multiple sequential extraction stages may be connected to the HAC reactor for improved performance.
    Type: Grant
    Filed: February 10, 1999
    Date of Patent: May 23, 2000
    Assignee: ILLA International, LLC
    Inventors: Vladimir Mikhailovitch Zakoshansky, Irina Ivanovna Vassilieva
  • Patent number: 6057483
    Abstract: Disclosed is a process for the cleavage of technical cumene hydroperoxide (CHP) into phenol, acetone and .alpha.-methylstyrene. In a first stage, the CHP cleavage process is conducted in such a way to maintain the heat generation rate and the heat removal rate balanced in each of the CHP cleavage reactors. The cleavage of the CHP is conducted under substantially isothermal conditions at a temperature in the range of 47-50.degree. C. In the second stage of the process dicumylperoxide (DCP) and dimethylbenzene alcohol (DMBA) cleavage is carried out in a multi-section plug-flow reactor under non-isothermal conditions at a controlled temperature increase. The temperature is controlled with the use of thermocouples installed in each section of the reactor. The obtained temperature profile is compared with the temperature profile required by the kinetic model based on .DELTA.T in each section of the reactor.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: May 2, 2000
    Assignee: Illa International, LLC
    Inventors: Vladimir Mikhailovitch Zakoshansky, Andrei Konstantinovitch Griaznov, Irina Ivanovna Vassilieva
  • Patent number: 6043399
    Abstract: The present invention lies in the field of the manufacture of phenol from cumene. The subject of the invention is a process for the continuous preparation of cumene hydroperoxide by oxidation, in the liquid phase, of cumene in the presence of oxygen. The process according to the invention is carried out in the presence of at least one agent chosen from the hydroxide or the carbonate of an alkali metal and/or alkaline-earth metal; the said agent being used in an amount of between 2 and 10 ppb (expressed as sodium hydroxide) with respect to the amount of cumene introduced. The invention likewise relates to the use of the hydroperoxide thus obtained for preparing phenol.
    Type: Grant
    Filed: February 12, 1999
    Date of Patent: March 28, 2000
    Assignee: Rhodia Chimie
    Inventors: Joao Amadio, Brice Le Corre, Jean-Jacques Charrin, Xavier Houzard, Philippe Laurent, Roland Noyerie, Yves-Michel Quenton
  • 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: 5922920
    Abstract: A method is provided for preparing organic hydroperoxides by oxidizing aryl alkyl hydrocarbons having a benzylic hydrogen with an oxygen containing gas using as a catalyst an oxo (hydroxo) bridged tetranuclear metal complex having a mixed metal core, one metal of the core being a divalent metal selected from Zn, Cu Fe, Co, Ni, Mn or mixtures thereof and another metal being a trivalent metal selected from In, Fe, Mn, Ga, and Al.
    Type: Grant
    Filed: April 2, 1996
    Date of Patent: July 13, 1999
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jeffrey Evans Bond, Sergiu Mircea Gorun, George William Schriver, Robert Timothy Stibrany, Thomas Henry Vanderspurt, Grayson Hall Via, Baoshan Zhang, Jihad Mohammed Dakka
  • Patent number: 5811598
    Abstract: Phenol dissolved in an aqueous sulphatic stream discharged from a reactor in which cumene hydroperoxide is oxidized to phenol and acetone is recovered by extracting phenol present in said aqueous sulphatic stream containing phenol, Na.sub.2 SO.sub.4 and organic impurities, in a multi-step extractor with an organic solvent, thereby forming an extracted product organic phase and a refined aqueous product phase, the ratio of the extracted product phase to the refined product phase ranging from 0.1 to 1 v/v at a temperature ranging from 20.degree.-70.degree. C., and obtaining phenol by distillation or re-extraction of the recovered extracted product organic phase.
    Type: Grant
    Filed: December 4, 1995
    Date of Patent: September 22, 1998
    Assignee: Enichem S.p.A.
    Inventors: Vanni Alessi, Sabrina Astori, Francesco Celin, Cecilia Gradella, Renzo Penzo
  • Patent number: 5639922
    Abstract: A process is described for the selective decomposition of aromatic primary hydroperoxides by contacting a hydroperoxide mixture containing aromatic primary hydroperoxides and aromatic tertiary hydroperoxides obtained by oxidation of alkylaromatic compounds under non-aqueous conditions with an alkali and an organic aromatic carboxylic acid salt.
    Type: Grant
    Filed: July 14, 1995
    Date of Patent: June 17, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoichi Ikeda, Motoo Hazama, Nobuhiro Kawara, Maki Okumura, Takanori Ito
  • Patent number: 5600026
    Abstract: There is disclosed a process for the production of cresols, including the steps of: (a) conducting oxygenation of cymene with oxygen gas or an oxygen-containing gas, thereby obtaining a solution of oxygenation products containing tertiary and primary hydroperoxides of cymene; (b) reacting the solution of oxygenation products obtained in the step (a) with an organic quaternary ammonium salt and an alkali, or with an organic quaternary ammonium hydroxide, thereby decreasing the content of primary hydroperoxide; (c) subjecting the reaction mixture in the step (b) to decomposition in the presence of a catalyst; and (d) subjecting the decomposition mixture in the step (c) to hydrogenation, thereby obtaining the desired cresols.
    Type: Grant
    Filed: February 23, 1995
    Date of Patent: February 4, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kiyoshi Ikimi, Yoichi Ikeda, Akira Murakami, Kazushige Okamoto, Tooru Tokumaru, Motoo Hazama
  • Patent number: 5550301
    Abstract: Organic hydroperoxides are decomposed by drying a reaction mixture containing the organic hydroperoxide and an organic solvent such that said dried reaction mixture comprises approximately 1 weight percent or less of water and contacting the dried reaction mixture with a metal organic ligand catalyst under hydroperoxide decomposition conditions. An organic co-solvent for the hydroperoxide may also be used. Particularly effective catalysts are cobalt acetylacetonates and ruthenium acetylacetonates and combinations thereof.
    Type: Grant
    Filed: March 3, 1995
    Date of Patent: August 27, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Manoj V. Bhinde, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 5530166
    Abstract: Technical cumylhydroperoxide of a wide composition range is cleaved in circulating reactors of a shell and tube design at the same elevated pressure as dicumyl peroxide is cleaved in a plug flow reactor with a recirculation ratio of at least 26. The cleavage process is controlled using two calorimeters and controlling the absolute .DELTA.T value which is the difference in the temperature drop between the two calorimeters.
    Type: Grant
    Filed: January 13, 1995
    Date of Patent: June 25, 1996
    Assignees: General Electric Company, Illa International
    Inventors: Vladimir M. Zakoshansky, Andrei K. Griaznov
  • Patent number: 5512175
    Abstract: An assembly for removing hydrophilic contaminants and a method of removing hydrophilic contaminants such as sodium included in an oil-state liquid using the removing assembly, which is able to remove positively the hydrophilic contaminants such as the sodium included in the oil-state liquid in each process of the plant such as a phenol producing apparatus as well as maintain a certain level of the removing performance for a long duration, consisting of: a coalescing element for coalescing and separating from the oil-state liquid the moisture including the hydrophilic contaminants such as sodium by being penetrated the fiber layer having the characteristics of alkali resistance and solvent resistance, typified by a carbon fiber; a liquid feeding means for feeding and supplying a mixed liquid of the moisture including the hydrophilic contaminants and the oil-state liquid; a water collecting means for collecting the moisture including the hydrophilic contaminants which is coalesced and separated; and a oil colle
    Type: Grant
    Filed: April 19, 1994
    Date of Patent: April 30, 1996
    Assignee: Wako Industrial Co., Ltd.
    Inventors: Mikio Saito, Tsuneo Yamaguchi
  • Patent number: 5510543
    Abstract: The present invention is an improved method for the recovery of phenol from a cleavage mass resulting from the sulfuric acid cleavage of cumene hydroperoxide comprising neutralizing the cleavage mass, forming an aqueous phase and an organic phase, separating the organic phase into an acetone-rich stream and a phenol-rich stream, removing phenol tars from the phenol-rich stream and cracking the phenol tars wherein the improvement comprises maintaining the pH of the cleavage mass during neutralization between 4.0 and about 4.9 whereby the sulfuric acid is converted to the bisulfate salt and substantially no free sulfuric acid remains in the cleavage mass and corrosion of process equipment is reduced.As a result of this improved process, a phenol tar waste stream containing less than about 4 parts per million by weight of chromium is obtained.
    Type: Grant
    Filed: December 9, 1994
    Date of Patent: April 23, 1996
    Assignee: General Electric Company
    Inventors: John W. Fulmer, Andrei K. Griaznov, William D. Kight, Vladimir M. Zakoshansky
  • 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: 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: 5463136
    Abstract: A process for the decomposition of cumene hydroperoxide to phenol, acetone, and alpha-methylstyrene is presented. In this process, cumene hydroperoxide and sulfuric acid are reacted in a reflux cooled reactor the products of which are transported under inhibited conditions to a plug flow reactor, and are reacted to produce phenol, acetone, and alpha-methylstyrene. In one embodiment of the invention, a heat exchanger is used to obtain and maintain the inhibited conditions of the transported reactor products.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Robert L. Blackbourn, Edgar D. Allan, Loc B. Le, Snehal Patel
  • Patent number: 5457244
    Abstract: An improved phenol tar cracking process using a rectification column as a hydrocracker obtains an increased yield of valuable products, phenol, cumene and alpha-methylstyrene, by taking from 50 to 100% of the acetophenone in the reactor overhead with the cracked product stream.
    Type: Grant
    Filed: October 4, 1994
    Date of Patent: October 10, 1995
    Assignee: General Electric Company
    Inventors: Arkadys S. Dyckman, John Fulmer, William D. Kight, Andrey Zinenkov, Vadim P. Boyarsky, Boris I. Gorovits, Leontii M. Krasnov, Alexander S. Malinovski, Yury I. Petrov, Anatoly D. Sorokin, Sergey N. Chernukhin
  • Patent number: 5430200
    Abstract: The present invention provides in a particular embodiment an improvement in the process for producing phenol by the acid-catalyzed cleavage of cumene hydroperoxide (CHP). The reactant stream fed to the cleavage reactor also includes the contaminant by-product dimethyl benzyl alcohol (DMBA) formed during the direct oxidation of cumene to CHP. This contaminant DMBA further reacts in the cleavage reactor to reduce the yield of phenol and produce undesirable and unreclaimable by-products. The improvement provided herein comprises performing the cleavage reaction at a reduced residence time of generally from one-half to five minutes, whereby the formation of .alpha.-methyl styrene from DMBA is promoted and the formation of the undesirable and unreclaimable by-products is reduced; .alpha.-methyl styrene is not only a useful by-product, but can be recycled and hydrogenated to the cumene starting material.
    Type: Grant
    Filed: September 16, 1994
    Date of Patent: July 4, 1995
    Assignee: Hercules Incorporated
    Inventor: Horace E. Hood
  • Patent number: 5414154
    Abstract: A process for the reduction of methylbenzofuran (MBF) impurities in phenol obtained from the decomposition product of cumene hydroperoxide requires treating the phenol to reduce the level of acetol, contacting the phenol containing a low level of acetol with an acid resin at sufficient temperature and residence time to reduce the level of MBF by conversion to higher boiling compounds, then distilling the phenol to separate phenol from higher boiling compounds. The phenol may be treated in known ways, such as by treatment with an amine, to reduce the level of acetol. The phenol containing a low level of acetol is contacted with a strong acid resin to reduce the level MBF.
    Type: Grant
    Filed: June 6, 1994
    Date of Patent: May 9, 1995
    Assignee: AlliedSignal Inc.
    Inventors: Theodore J. Jenczewski, Lamberto Crescentini, James A. Kweeder
  • Patent number: 5399791
    Abstract: There is disclosed a process for the production of cresols, including the steps of: (a) conducting oxygenation of cymene with oxygen gas or an oxygen-containing gas without any addition of an alkali, thereby obtaining a solution of oxygenation products containing tertiary and primary hydroperoxides of cymene; (b) washing the solution of oxygenation products obtained in step (a) with an aqueous alkali solution at a temperature in the range of from 10.degree. to 95.degree. C.; (c) subjecting the solution of oxygenation products obtained in step (b) to hydrogenation at a temperature in the range of from 60.degree. to 100.degree. C. to decrease the content of primary hydroperoxide in such a manner that the weight ratio of primary hydroperoxide to tertiary hydroperoxide is not greater than 1/25 (w/w); (d) subjecting the solution treated in step (c) to decomposition in the presence of a catalyst; and (e) subjecting the solution treated in step (d) to hydrogenation to obtain cresols.
    Type: Grant
    Filed: February 25, 1994
    Date of Patent: March 21, 1995
    Assignee: Suitomo Chemical Company, Limited
    Inventors: Kiyoshi Ikimi, Yoichi Ikeda, Akira Murakami, Kazushige Okamoto, Tooru Tokumaru, Motoo Hazama
  • Patent number: 5371305
    Abstract: The present invention provides in a particular embodiment an improvement in the process for producing phenol by the acid-catalyzed cleavage of cumene hydroperoxide (CHP). The reactant stream fed to the cleavage reactor also includes the contaminant by-product dimethyl benzyl alcohol (DMBA) formed during the direct oxidation of cumene to CHP. This contaminant DMBA further reacts in the cleavage reactor to reduce the yield of phenol and produce undesirable and unreclaimable by-products. The improvement provided herein comprises performing the cleavage reaction at a reduced residence time of generally from one-half to five minutes, whereby the formation of .alpha.-methyl styrene from DMBA is promoted and the formation of the undesirable and unreclaimable by-products is reduced; .alpha.-methyl styrene is not only a useful by-product, but can be recycled and hydrogenated to the cumene starting material.
    Type: Grant
    Filed: December 31, 1992
    Date of Patent: December 6, 1994
    Assignee: Hercules Incorporated
    Inventor: Horace E. Hood
  • Patent number: 5331103
    Abstract: The present invention relates to a process for monohydroxylation of phenolic compounds which allows an increase in the amount of para isomer.The invention relates to a process for monohydroxylation of a phenolic compound having a hydrogen atom in the para position to the hydroxyl group, for the purpose of obtaining a dihydroxylated aromatic compound by reacting the initial phenolic compound with hydrogen peroxide in the presence of an effective amount of a strong acid and of a ketonic compound, said process being characterized by the fact that the reaction is carried out in the presence of an effective amount of a polar aprotic organic solvent with a basicity such that it has a "donor number" below 25.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: July 19, 1994
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Dominique Laucher
  • Patent number: 5304684
    Abstract: sec-Butylbenzene hydroperoxide obtained by oxidizing sec-butylbenzene is decomposed into phenol and methyl ethyl ketone, a resulting liquid comprising a methyl ethyl ketone as the main component is washed with an aqueous alkali solution to remove carboxylic acids, carboxylic acid esters, unsaturated ketones, and aldehydes, and the washed liquid is further subjected to neutralization, dehydration, and distillation.A methyl ethyl ketone can be obtained which has a high quality with regard to purity and potassium permanganate fading.
    Type: Grant
    Filed: July 7, 1993
    Date of Patent: April 19, 1994
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Hiroshi Nishida, Kazuo Kimura, Shouji Hamada, Masaaki Toma, Hirooki Nagaoka
  • Patent number: 5298667
    Abstract: Any one material selected from (A) sec-butylbenzene substantially free from ethyl hydroperoxide, carboxylic acids and phenol, (B) sec-butylbenzene substantially free from styrenes and (C) sec-butylbenzene substantially free from methylbenzyl alcohol is oxidized to obtain sec-butylbenzene hydroperoxide, which is then decomposed to obtain phenol and methyl ethyl ketone.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: March 29, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kiyoshi Iwanaga, Mitsuhisa Tamura, Toshio Nakayama, Masahiro Usui, Hiroyuki Umida, Hirooki Nagaoka
  • Patent number: 5264636
    Abstract: A process for producing a highly pure phenol, in which a crude phenol obtained from an acid-decomposition product of cumene hydroperoxide and having an .alpha.-methylstyrene content of 15% by weight or less is catalytically treated with an acidic .gamma.-alumina catalyst having a specific surface area of 80 to 400 m.sup.2 /g and an acid strength, according to Hammett's acidity function (Ho), of 3.ltoreq.Ho.ltoreq.6.8, in order to convert aliphatic and aromatic carbonyl compounds contained in the crude phenol into high-boiling compounds without causing the substantial formation of a dimer of .alpha.-methylstyrene contained in the crude phenol, and then, a phenol and the so-formed high-boiling compounds were separated by distillation.
    Type: Grant
    Filed: March 30, 1993
    Date of Patent: November 23, 1993
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Tatsuo Shirahata, Tetsuo Imamura
  • Patent number: 5254751
    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.degree. to 110.degree. 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: September 14, 1992
    Date of Patent: October 19, 1993
    Assignee: General Electric Company
    Inventor: Vladimir M. Zakoshansky