Of Phenol Prepared By Cleavage Of Hydroperoxide Or Other Peroxide Patents (Class 568/754)
  • Patent number: 11407694
    Abstract: In a process of decomposing byproducts of a phenol production process using a reactive distillation column in which a reactor and a distillation column are integrated, since acetophenone is mixed with tar recovered to a lower part of the reactive distillation column and transferred, viscosity of the tar may be lowered so that the tar may be transferred at room temperature, and since the reactive distillation column may be operated at 0.5 to 3 bar, an operating temperature of the reactive distillation column is low as compared with a method of separating acetophenone by pressurization with high pressure, significantly reducing an operation cost of a heater required for a reaction. Also, since acetophenone is separately recovered at a position of 25 to 90% of a total number of stages in the reactive distillation column, recovery of an active ingredient may be enhanced.
    Type: Grant
    Filed: August 17, 2018
    Date of Patent: August 9, 2022
    Assignee: LG CHEM, LTD.
    Inventors: Min Suk Kang, Sang Beom Lee, Sung Ho Lee, Joon Ho Shin, Chul Han Park
  • Patent number: 11247958
    Abstract: The present disclosure relates to a method and an apparatus for decomposing a phenolic by-product generated in a bisphenol A preparation process, the method including: a step (S10) of feeding the phenolic by-product to a multistage reactive distillation column; a step (S20) of separating the phenolic by-product into an upper discharge stream containing an active component, a side discharge stream containing acetophenone, and a bottom discharge stream containing tar by the multistage reactive distillation column; and a step (S30) of mixing the side discharge stream discharged from the multistage reactive distillation column and the bottom discharge stream discharged from the multistage reactive distillation column to form a mixed discharge stream.
    Type: Grant
    Filed: October 15, 2019
    Date of Patent: February 15, 2022
    Assignee: LG Chem, Ltd.
    Inventors: Min Suk Kang, Sang Beom Lee, Joon Ho Shin
  • Patent number: 11192047
    Abstract: A method of decomposing a phenol by-product produced in a phenol preparation process, in which acetophenone separated from a distillation column is mixed with tar separated and collected in a decomposition reactor, thereby significantly decreasing viscosity of tar. The decomposition method according to the present invention allows tar to have sufficient viscosity for flowability even at room temperature, whereby transfer and storage of tar may be more smoothly done without using any heating device for transfer of tar.
    Type: Grant
    Filed: August 17, 2018
    Date of Patent: December 7, 2021
    Assignee: LG CHEM, LTD.
    Inventors: Minsuk Kang, Sang Beom Lee, Sung Ho Lee, Joon Ho Shin, Sangeun Kim
  • Patent number: 11148987
    Abstract: A method of reducing the salt content of a neutralized aralkyl hydroperoxide cleavage mass stream comprising passing the neutralized stream into a vessel, the vessel having an inlet, two outlets, an aqueous layer and a hydrocarbon layer wherein the neutralized stream enters the vessel through a first inlet and a hydrocarbon stream exits the vessel through a first outlet that is in fluid communication with the hydrocarbon layer.
    Type: Grant
    Filed: August 22, 2018
    Date of Patent: October 19, 2021
    Assignee: SHELL OIL COMPANY
    Inventors: Garry Morgan McCauley, Jamie Jerrick Juliette, David Randall Faske, Thomas Robert Porter
  • Patent number: 9193652
    Abstract: Methods and systems for purifying phenol. The method can include contacting a feed that includes phenol and an aldehyde containing compound with a first ion exchange material to produce a first treated product. The first treated product can have a pH that is less than a pH of the feed. The first treated product can contain less of the aldehyde containing compound than the feed. The first treated product can be contacted with a second ion exchange material to produce a second treated product. The second treated product can have a pH that is greater than the pH of the first treated product. Each of the first ion exchange material and the second ion exchange material can be a solid, a semi-solid, or a combination thereof.
    Type: Grant
    Filed: February 26, 2015
    Date of Patent: November 24, 2015
    Assignee: KELLOGG BROWN & ROOT LLC
    Inventor: Theodor Wilks
  • Publication number: 20150094495
    Abstract: In a process for separating a mixture comprising cyclohexanone and phenol, at least a portion of the mixture is distilled in the presence of a solvent including at least two alcoholic hydroxyl groups attached to non-adjacent saturated carbon atoms, water, and in the presence or absence of a hemiketal defined by the formula (I) or the formula (II): wherein R1, the same or different at each occurrence, is independently an alkylene group having from 2 to 10 carbon atoms, R2 is an alkylene group having from 4 to 10 carbon atoms and/or R3 is hydrogen or the following group: and in the presence or absence of an enol-ether derived from the hemiketal defined by the formula (I) or the formula (II), wherein the total concentration of the hemiketal and enol-ether, expressed in term of weight percentage of the total weight of the feed to the distilling step, is at most 0.01%.
    Type: Application
    Filed: April 9, 2013
    Publication date: April 2, 2015
    Applicant: ExxonMobil Chemical Company Patents Inc.
    Inventors: Keith H. Kuechler, Francisco M. Benitez, Krystle J. Chavez, Christopher L. Becker, John L. Heidman
  • Publication number: 20140148569
    Abstract: In a process for oxidizing a feed comprising cyclohexylbenzene, the feed is contacted with oxygen and an oxidation catalyst in a plurality of reaction zones connected in series, the contacting being conducted under conditions being effective to oxidize part of the cyclohexylbenzene in the feed to cyclohexylbenzene hydroperoxide in each reaction zone. At least one of the plurality of reaction zones has a reaction condition that is different from another of the plurality of reaction zones. The different reaction conditions may include one or more of (a) a progressively decreasing temperature and (b) a progressively increasing oxidation catalyst concentration as the feed flows from one reaction zone to subsequent reaction zones in the series.
    Type: Application
    Filed: August 16, 2011
    Publication date: May 29, 2014
    Applicant: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad Mohammed Dakka, Francisco Manuel Benitez, Bryan Amrutlal Patel, Edmund John Mozeleski
  • Patent number: 8389776
    Abstract: A process for the removal of by-products from a phenolic mixture, which process may include the following steps: subjecting a phenolic mixture to extractive distillation to produce an initial phenolic mixture, contacting the initial phenolic mixture containing phenol and one or more by products with a catalyst to produce a first purified phenol product mixture, and distilling the first purified phenol product mixture to produce a second purified phenol product mixture; wherein the extractive distillation is carried out in two columns, a higher pressure column and a lower pressure column.
    Type: Grant
    Filed: December 22, 2008
    Date of Patent: March 5, 2013
    Assignee: Borealis Technology Oy
    Inventor: Veli-Matti Purola
  • Patent number: 8298378
    Abstract: A method for treating a wastewater containing oxygen-containing compound having a phenolic hydroxyl group or a carbonyl group, including a step of adding an alkali agent to the wastewater containing the oxygen-containing compound having a phenolic hydroxyl group or a carbonyl group to control a pH of the wastewater to 10 or more; and a step of separating a discharge in which the oxygen-containing compound having a phenolic hydroxyl group or a carbonyl group is concentrated through distillation of the wastewater to which the alkali agent has been added.
    Type: Grant
    Filed: March 24, 2006
    Date of Patent: October 30, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Kenji Itoh
  • Patent number: 7902408
    Abstract: The present disclosure enables phenol recovery, purification and recycle in a simple, economic manner from waste streams from, for example, a phenol/acetone production process, e.g., a phenol/acetone plant or an upstream cumene hydroperoxide cleavage process step, and BPA production step, for use in the reaction with acetone to produce BPA. The disclosure therefore reduces the overall consumption of phenol in the production of BPA.
    Type: Grant
    Filed: May 1, 2008
    Date of Patent: March 8, 2011
    Assignee: Stone & Webster, Inc.
    Inventor: David P. Palmer
  • Publication number: 20100280285
    Abstract: A process for the removal of by-products from a phenolic mixture, which process may include the following steps: subjecting a phenolic mixture to extractive distillation to produce an initial phenolic mixture, contacting the initial phenolic mixture containing phenol and one or more by products with a catalyst to produce a first purified phenol product mixture, and distilling the first purified phenol product mixture to produce a second purified phenol product mixture; wherein the extractive distillation is carried out in two columns, a higher pressure column and a lower pressure column.
    Type: Application
    Filed: December 22, 2008
    Publication date: November 4, 2010
    Applicant: BOREALIS TECHNOLOGY OY
    Inventor: Veli-Matti Purola
  • Patent number: 7759524
    Abstract: In a process for producing phenol and methyl ethyl ketone, benzene and a C4 olefin are contacted under alkylation conditions and in the presence of an alkylation catalyst to produce sec-butylbenzene. The sec-butylbenzene is then oxidized to produce an oxidation effluent comprising sec-butylbenzene hydroperoxide and acetophenone. At least part of the sec-butylbenzene hydroperoxide in the oxidation effluent is cleaved to produce phenol and methyl ethyl ketone, while at least part of the acetophenone is hydrogenated to produce at least one of methyl benzyl alcohol, styrene and ethylbenzene.
    Type: Grant
    Filed: December 18, 2008
    Date of Patent: July 20, 2010
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: John Scott Buchanan, Jihad Mohammed Dakka, Stephen Zushma, Francisco Manuel Benitez, Steven E. Silverberg
  • Patent number: 7488853
    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: Grant
    Filed: February 15, 2007
    Date of Patent: February 10, 2009
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventor: Tomoyuki Noritake
  • Patent number: 7446232
    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, 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: Grant
    Filed: July 13, 2007
    Date of Patent: November 4, 2008
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad Mohammed Dakka, Doron Levin, John Scott Buchanan, Jon Edmond Randolph Stanat
  • Patent number: 7282613
    Abstract: A process for producing phenol and methyl ethyl ketone (MEK).
    Type: Grant
    Filed: January 21, 2004
    Date of Patent: October 16, 2007
    Assignee: Shell Oil Company
    Inventors: Jesse Raymond Black, Jiemin Yang, James Laurel Buechele
  • Patent number: 7102036
    Abstract: The goal of this invention is to produce phenol of high purity by conversion of impurities that are present in the starting phenol, which is produced by the decomposition of cumyl hydroperoxide. The indicated goal is achieved by purifying the phenol containing admixtures of aliphatic and aromatic carbonyl compounds with an aluminum zirconium catalyst.
    Type: Grant
    Filed: January 30, 2003
    Date of Patent: September 5, 2006
    Assignee: General Electric Company
    Inventors: Arkady Samuilovich Dyckman, John William Fulmer, Boris V. Krasy, Viktor Vladimirovich Pinson, Yury Alekseevich Shavandin, Genrikh Petrovich Yavshits, Andrey Vladimirovich Zinenkov
  • Patent number: 7067680
    Abstract: A process for preparing organic hydroperoxide having a reduced content of contaminants, which process involves: (a) oxidation of an organic compound to obtain reaction product containing an organic hydroperoxide; (b) contacting at least part of the organic hydroperoxide containing reaction product with a basic aqueous solution; (c) separating the hydrocarbonaceous phase containing organic hydroperoxide from the aqueous phase; (d) washing at least part of the separated hydrocarbonaceous phase containing organic hydroperoxide; and (e) contacting at least part of the hydrocarbonaceous phase containing organic hydroperoxide with a guard bed having solid adsorbent with a void content of from 50% to 98% by volume.
    Type: Grant
    Filed: December 17, 2001
    Date of Patent: June 27, 2006
    Assignee: Shell Oil Company
    Inventor: Carolus Matthias Anna Maria Mesters
  • Patent number: 7034192
    Abstract: A method is provided for the efficient, low cost removal of acetol from a phenol stream. The method results in removal of substantially all of the acetol from the phenol stream without the formation of substantial amounts of additional methylbenzofuran. The method also avoids the use of expensive reagents and capital intensive distillation equipment.
    Type: Grant
    Filed: August 9, 2004
    Date of Patent: April 25, 2006
    Assignee: Sunoco Inc. (R&M)
    Inventor: Tilak P. Wijesekera
  • Patent number: 7019180
    Abstract: A method of purifying a phenol stream that contains a concentration of a contaminating compound is provided. The phenol stream is treated or purified by contacting the stream, under suitable process conditions, with a treatment catalyst that has a low silica content but comprises alumina and a Group VIA metal.
    Type: Grant
    Filed: January 21, 2004
    Date of Patent: March 28, 2006
    Assignee: Shell Oil Company
    Inventor: Larry Wayne Payne
  • Patent number: 7002048
    Abstract: A method is provided for the efficient, low cost removal of acetol from a phenol stream. The method results in removal of substantially all of the acetol from the phenol stream without the formation of substantial amounts of additional methylbenzofuran. The method also avoids the use of expensive reagents and capital intensive distillation equipment.
    Type: Grant
    Filed: September 16, 2004
    Date of Patent: February 21, 2006
    Assignee: Sunoco, Inc. (R&M)
    Inventors: Tilak P. Wijesekera, Manoj V. Bhinde
  • 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: 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: 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.
  • Patent number: 6824687
    Abstract: A method is provided herein for the extraction of phenol from a waste water stream. The method is used in conjunction with a process for producing acetone and phenol from cumene. The method for extracting phenol from waste water includes contacting in a countercurrent mode a phenol-containing waste water stream with a hydrocarbon stream derived from a bottoms stream from the acetone finishing column to produce a dephenolated waste water stream and a phenol-containing hydrocarbon stream. The phenol-containing hydrocarbon stream is preferably washed with an aqueous caustic solution to provide a hydrocarbon stream, which is then conveyed to the alpha-methylstyrene recovery system. Preferably the hydrocarbon stream derived from the bottoms stream of the acetone finishing column is water washed prior to contacting the phenol-containing waste water stream.
    Type: Grant
    Filed: November 20, 2002
    Date of Patent: November 30, 2004
    Assignee: ABB Lummus Global Inc.
    Inventors: Sunil S. Panditrao, Amit Kelkar, Sanjeev Ram, Ajay Gami, James M. Hildreth
  • Patent number: 6720461
    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: December 1, 2000
    Date of Patent: April 13, 2004
    Assignee: Shell Oil Company
    Inventors: Austin Dale Taggart, II, Edgar Donald Allan, Roberto Carlos Longoria, David Werner Daum, Robert Lawrence Blackbourn
  • Patent number: 6657087
    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. By means of the inventive process for the work-up by distillation of cleavage product mixtures, the equipment requirements and the energy consumption can be markedly reduced in comparison with customary plants, since the cleavage product mixture can be resolved into the three main fractions in only one apparatus.
    Type: Grant
    Filed: November 13, 2001
    Date of Patent: December 2, 2003
    Assignee: INEOS Phenol GmbH & Co. KG
    Inventors: Markus Weber, Christoph Schwarz, Uwe Tanger, Hermann-Josef Korte, Jochen Ullrich
  • Publication number: 20030220528
    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: Application
    Filed: April 4, 2003
    Publication date: November 27, 2003
    Inventors: Manfred Weber, Reinhard Sigg, Michael Lausmann, Siegmund Greschek
  • Patent number: 6635789
    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: Grant
    Filed: March 6, 2002
    Date of Patent: October 21, 2003
    Assignee: General Electric Company
    Inventors: John W. Fulmer, Nitin Vaish, Pramod Kumbhar, Jacob L. Oberholtzer, R. Jothi Mahalingam
  • 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
  • Patent number: 6620980
    Abstract: An improved method for the recovery of phenol from aqueous streams comprises adding a relatively non-polar solvent to a phenol containing aqueous stream to improve the separation of the phenol form the aqueous stream. The improvement results in a phenol stream with a reduced level of salt carried over from the aqueous stream.
    Type: Grant
    Filed: April 12, 2002
    Date of Patent: September 16, 2003
    Assignee: Sunoco Inc (R&M)
    Inventors: Robert W. Emblidge, Scott R. Keenan
  • Publication number: 20030163007
    Abstract: The goal of this invention is to produce phenol of high purity by conversion of impurities that are present in the starting phenol, which is produced by the decomposition of cumyl hydroperoxide. The indicated goal is achieved by purifying the phenol containing admixtures of aliphatic and aromatic carbonyl compounds with an aluminum zirconium catalyst.
    Type: Application
    Filed: January 30, 2003
    Publication date: August 28, 2003
    Inventors: Arkady Samuilovich Dyckman, John William Fulmer, Boris V. Krasy, Viktor Vladimirovich Pinson, Yury Alekseevich Shavandin, Genrikh Petrovich Yavshits, Andrey Vladimirovich Zinenkov
  • 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: 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
  • Patent number: 6489519
    Abstract: Impurities are removed from phenol by a process, comprising: first treating phenols containing impurities with at least one acid catalyst which converts the impurities into compounds which can be separated from phenol; separating the acid treated phenol from the compounds; and treating the distilled phenol a second time with at least one acid catalyst; thereby effectively removing the impurities from phenol.
    Type: Grant
    Filed: October 26, 2000
    Date of Patent: December 3, 2002
    Assignee: Phenolchemie GmbH & Co. KG
    Inventors: Heinrich van Barneveld, Otto Gerlich, Wilfried Jordan, Otto Schnurr, Hugo H. J. M. Liefooche
  • Patent number: 6489518
    Abstract: A process for reducing the salt content of fractions comprising high boilers obtained in the preparation of phenol from cumene, by extraction, is claimed. In the preparation of phenol from cumene, not only phenol and acetone but also by-products such as dimethyl phenyl carbinol or acetophenone are formed in the cleavage of cumene hydroperoxide. In the work-up of the cleavage product phase by distillation, these by-products are obtained as a fraction which boils only at high temperatures. These fractions further comprise alkali metal in the form of salts as a result of the neutralization by means of aqueous sodium hydroxide after the acid catalyzed cleavage. The presence of salt in this phase makes the work-up of this phase considerably more difficult. The salt is usually removed from the fraction by extraction of the fraction with water. However, considerable problems can occur if the aqueous phase cannot be cleanly separated from the organic phase.
    Type: Grant
    Filed: November 13, 2000
    Date of Patent: December 3, 2002
    Assignee: Phenolchemie GmbH & Co. KG
    Inventors: Manfred Weber, Markus Weber, Heinrich van Barneveld, Peter Bickert, Wilfried Jordan
  • 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: 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
  • Patent number: 6388144
    Abstract: A process for treating phenol with a strong acid ion exchange resin to reduce the level of methylbenzofuran is provided. The process is capable of being carried out at elevated temperatures for extended periods, such that cooling of the phenol from distillation temperatures prior to the resin treatment is not required. The process can reduce or eliminate the substantial costs associated with conventional processes that require cooling and re-heating the phenol.
    Type: Grant
    Filed: June 15, 2001
    Date of Patent: May 14, 2002
    Assignee: Sunoco, Inc. (R&M)
    Inventors: Tilak P. Wijesekera, Scott R. Keenan
  • 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: 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: 6180834
    Abstract: Process for the extraction of the salts contained in the neutralized separated product obtained in the preparation of phenol by the oxidation of cumene, wherein the flow-rate of the aqueous stream of the separation section of cumene hydroperoxide is reduced by substituting the stream of fresh water used for washing the neutralized separated product, generally obtained by the demineralization of well or running water, with process water taken from another section of the production plant.
    Type: Grant
    Filed: April 8, 1999
    Date of Patent: January 30, 2001
    Assignee: Enichem S.p.A.
    Inventors: Vanni Alessi, Renzo Penzo
  • 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: 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: 6034282
    Abstract: A method for reduction of salt content in phenol tars with no additional solvent which washes the tars with water alone in a countercurrent flow extractor and substantially reduces the level of salt in the tar.
    Type: Grant
    Filed: July 31, 1998
    Date of Patent: March 7, 2000
    Assignee: General Electric Company
    Inventors: Arkady S. Dyckman, Vladimir I. Sarge, Yelena N. Sarge, Boris I. Gorovits