Preparing From Peroxide Or Preparing By Oxidation Patents (Class 568/741)
  • Patent number: 11208370
    Abstract: The present invention describes compositions comprising at least one compound chosen from hydroquinone and catechol, characterised in that it further comprises between 0.1 and 10,000 ppm of at least one compound chosen from 2-(alkoxy)phenol, 4-(alkoxy)phenol, 2-(alkyl)phenol, 4-(alkyl)phenol, (alkyl)catechol and (alkyl)hydroquinone. Another aspect of this invention concerns a method for preparing a composition comprising at least one compound chosen from hydroquinone and catechol according to the invention, characterised in that it comprises a step (a) of reacting the phenol with hydrogen peroxide in the presence of a catalyst, in a solvent comprising an alcohol.
    Type: Grant
    Filed: June 12, 2018
    Date of Patent: December 28, 2021
    Assignee: RHODIA OPERATIONS
    Inventor: Laurent Garel
  • Patent number: 10486080
    Abstract: The present application relates to a distillation device. When a feedstock containing acetone and methanol is separated using a distillation device according to the present application, a methanol removal distillation column may be located at a position for easily separating methanol to solve a problem due to accumulation of methanol in the process and to lower the methanol content in the acetone product, and thus the lifetime of catalysts can be extended, and moreover, methanol can be removed with good efficiency from a flow of the lower part of the distillation column obtaining the final acetone product by using only the conventional phase separator and one methanol removal distillation column further installed, so that the acetone product obtained from the upper part of the distillation column obtaining the acetone product can be obtained in high purity and the operating cost and the equipment cost of equipments can be greatly reduced.
    Type: Grant
    Filed: July 1, 2016
    Date of Patent: November 26, 2019
    Assignee: LG CHEM, LTD.
    Inventors: Yeon Uk Choo, Sung Kyu Lee, Tae Woo Kim, Jong Suh Park, Joon Ho Shin
  • Patent number: 8932980
    Abstract: The invention discloses three-dimensional, ordered, mesoporous titanosilicates wherein the Ti is in a tetrahedral geometry and exclusively substituted for Si in the silica framework. Such titanosilicates find use as catalysts for epoxidation, hydroxylation, C—H bond oxidation, oxidation of sulfides, aminolysis of epoxide and amoximation, with approx. 100% selectivity towards the products.
    Type: Grant
    Filed: July 20, 2011
    Date of Patent: January 13, 2015
    Assignee: Council of Scientific & Industrial Research
    Inventors: Srinivas Darbha, Anuj Kumar
  • Patent number: 8921609
    Abstract: In a process for oxidizing a hydrocarbon, the hydrocarbon is contacted with oxygen in the presence of an N-substituted cyclic imide and under conditions to oxidize the hydrocarbon to produce an oxidized hydrocarbon product and at least one decomposition product of the N-substituted cyclic imide. At least a portion of the at least one decomposition product is contacted with hydroxylamine or a salt thereof under conditions to convert the at least one decomposition product back to said imide.
    Type: Grant
    Filed: September 30, 2010
    Date of Patent: December 30, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad M. Dakka, Stephen Zushma, Nicolas P. Coute, Francisco M. Benitez, Edmund J. Mozeleski
  • Patent number: 8921610
    Abstract: A process for oxidizing a composition comprising contacting an alkylbenzene of the general formula (I): where R1 and R2 each independently represents hydrogen or an alkyl group having from 1 to 4 carbon atoms, wherein R1 and R2 may be joined to form a cyclic group having from 4 to 10 carbon atoms, the cyclic group being optionally substituted, and R3 represents hydrogen, one or more alkyl groups having from 1 to 4 carbon atoms or a cyclohexyl group; and (ii) about 0.05 wt % to about 5 wt % of phenol, with oxygen in the presence of a catalyst containing a cyclic imide having the general formula (II): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group under conditions effective to convert at least a portion of the alkylbenzene to a hydroperoxide.
    Type: Grant
    Filed: August 16, 2011
    Date of Patent: December 30, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad M. Dakka, Edmund J. Mozeleski, Charles Morris Smith, Christopher L. Becker, Stephen Zushma
  • Publication number: 20130116453
    Abstract: The invention discloses three-dimensional, ordered, mesoporous titanosilicates wherein the Ti is in a tetrahedral geometry and exclusively substituted for Si in the silica framework. Such titanosilicates find use as catalysts for epoxidation, hydroxylation, C—H bond oxidation, oxidation of sulfides, aminolysis of epoxide and amoximation, with approx. 100% selectivity towards the products.
    Type: Application
    Filed: July 20, 2011
    Publication date: May 9, 2013
    Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
    Inventors: Srinivas Darbha, Anuj Kumar
  • Patent number: 7626060
    Abstract: To improve energy efficiency of prior art processes while preserving the standards of quality and total yield of desired end products, a process for the preparation of phenolic compounds is proposed.
    Type: Grant
    Filed: July 9, 2004
    Date of Patent: December 1, 2009
    Assignee: INEOS Phenol GmbH & Co., KG
    Inventors: Christoph Schwarz, Markus Weber, Manfred Weber
  • Patent number: 6900358
    Abstract: A process for hydroxylating benzene under catalytic distillation conditions to produce hydroxylated products such as phenol is provided. The process provides for direct hydroxylation of liquid phase benzene with an oxidant and a zeolite catalyst under conditions effective to prevent coke formation on the catalyst.
    Type: Grant
    Filed: April 24, 2001
    Date of Patent: May 31, 2005
    Assignee: Shell Oil Company
    Inventor: David Morris Hamilton, Jr.
  • 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: 6482989
    Abstract: A method for oxidizing an alkane, comprising the step of oxidizing said alkane with oxygen in the presence of an aldehyde, a copper-based catalyst and a nitrogen-containing compound. This method may be used to convert alkanes to corresponding alcohols and ketone having pharmaceutical activities, etc.
    Type: Grant
    Filed: July 18, 2001
    Date of Patent: November 19, 2002
    Assignee: Osaka University
    Inventors: Shun-ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
  • Patent number: 6479711
    Abstract: A process for producing an aromatic hydroxy compound having hydroxyl group at the para-position with respect to a hydroxy or an alkoxy substituent group present in the aromatic ring at a high yield and at a high selectivity, using a novel and useful hydroxylation catalyst which can afford to introduce hydroxyl group directly into aromatic ring at the para-position with respect to a hydroxy or an alkoxy substituent group, by reacting at least one compound selected from the group consisting of phenols, alkoxybenzenes and derivatives of them with hydrogen peroxide in the presence of the catalyst, wherein the hydroxylation catalyst is constituted of an oleophilized crystalline titanosilicate.
    Type: Grant
    Filed: April 28, 2000
    Date of Patent: November 12, 2002
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Toshihiro Takai, Kazuaki Matsui
  • 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: 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: 6365762
    Abstract: The invention relates to the use of compounds of the formula R1aRebOc.Ld  (I), in which and the total of a, b and c is such as to comply with the pentavalency or heptavalency of rhenium, with the proviso that c is not larger than 3×b, and in which R1 is absent or identical or different, and is an aliphatic hydrocarbon radical having 1 to 10 carbon atoms, an aromatic hydrocarbon radical having 6 to 10 carbon atoms or an arylalkyl radical having 7 to 9 carbon atoms, it being possible for the R1 radicals where appropriate to be substituted identically or differently, independently of one another, as catalysts for oxidizing electron-rich aromatic compounds and their derivatives, the catalysts being employed in a peroxide-containing solution in the presence of an anhydride of a carboxylic acid and/or of a dehydrating agent.
    Type: Grant
    Filed: March 14, 2000
    Date of Patent: April 2, 2002
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Richard Walter Fischer, Joachim Haider, Wolfgang Anton Herrmann, Roland Kratzer
  • 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
  • Publication number: 20010039362
    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: Application
    Filed: May 3, 2001
    Publication date: November 8, 2001
    Applicant: PHENOLCHEMIE GmbH & Co. KG
    Inventors: Sigg Reinhard, Tanger Uwe, Weber Manfred, Schnurr Otto, Liefooghe Hugo H.J. M.
  • 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: 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: 5962752
    Abstract: A process is disclosed for the catalytic hydroxylation of aromatic hydrocarbons which comprises contacting aromatic feedstock with oxidant comprising molecular oxygen, under suitable reaction conditions, in the presence of a catalyst comprising vanadyl (V.sup.IV) on an alumina support, preferably on leached alumina. The process is particularly suited, for example, to the one-step conversion of benzene to phenol.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: October 5, 1999
    Assignee: Sun Company, Inc.
    Inventors: Vincent A. Durante, Tilak P. Wijesekera, Swati Karmakar
  • Patent number: 5932773
    Abstract: This invention relates to a process for the hydroxylation of napthalene to .varies. and .beta. naphthols which comprises reacting napthalene with hydrogen peroxide in the presence of a solid catalyst containing an organotransition metal complex wherein some or all of the hydrogen atoms of the said organotransition metal complex have been substituted by one or more electron withdrawing group in the presence of solvents, with or without promoter and isolating the naphthols formed by conventional methods.
    Type: Grant
    Filed: March 31, 1997
    Date of Patent: August 3, 1999
    Assignee: Council of Scientific & Industrial Research
    Inventors: Paul Ratnasamy, Robert Raja, Pramod Prabhakar Moghe, Madhav Gopal Kotasthane, Ashwini Vinayak Pol, Prakash Kondiba Bahirat
  • Patent number: 5811599
    Abstract: A process for the oxidation of hydrocarbons and their derivatives having the general formula RX, wherein R is from n-alkyl, iso-alkyl, benzyl, cyclohexyl, mono, di or tricyclic aryl, or alkenic groups and X is selected from H, OH or Cl to compounds having formula R.sup.1 XY wherein R.sup.1 =(R--H), X has the meaning defined as above and Y=OH; which comprises of reacting the appropriate hydrocarbon or it's derivative of the formula RX where R and X have the meaning given above, with a solution of aqueous hydrogen peroxide at a temperature in the range of 10.degree.-100.degree. C. in the presence of an amorphous titanium-silicate catalyst having molar chemical composition in terms of the anhydrous oxides of TiO.sub.2 : (5-400) SiO.sub.2, having an average micropore radius between 10 and 40 .ANG., an absorption band around 220 nm in the ultraviolet region, a band around 960 cm.sup.-1 in the infrared region, interatomic vectors around 1.6-1.7, 2.7-2.8, 4.1-4.2 and 5.0-5.2 .ANG.
    Type: Grant
    Filed: August 2, 1995
    Date of Patent: September 22, 1998
    Inventors: Keshavaraja Alive, Ramaswamy Arumugamangalam Venkataraman, Ratnasamy Paul
  • Patent number: 5670465
    Abstract: p-Dihydroxylated aromatic compounds are prepared via the oxidation of p-fuchsones, the latter advantageously being synthesized by reacting a phenolic compound having at least one hydrogen atom in the para-position to the hydroxyl function with a non-enolizable ketonic compound, in the presence of a catalytically effective amount of an acid catalyst and, optionally, a cocatalytically effective amount of an ionizable sulfur-containing compound.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: September 23, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Daniel Manaut, Daniel Michelet
  • 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: 5504260
    Abstract: Organic compounds are selectively oxidized by means of a particularly advantageous process, using elemental oxygen and a catalyst containing palladium and copper and carrying out the process in the presence of carbon monoxide.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: April 2, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Zoltan Kricsfalussy, Helmut Waldmann, Hans-Joachim Traenckner
  • 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: 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: 5426244
    Abstract: Phenols are reacted with a hydrogen peroxide in the presence of a crystalline titanosilicate catalyst and a cyclic ether, such as dioxane, as a solvent. The method provides especially high para-selectivity compared with conventional methods, and, at the same time, provides high yields of dihydric phenols versus hydrogen peroxide.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: June 20, 1995
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Ryuji Sugai, Osamu Kondo, Yuki Motoyama, Shu Yoshida
  • Patent number: 5414155
    Abstract: o-Dihydroxylated aromatic compounds, for example pyrocatechol, are selectively prepared by reacting an o-fuchsone with an oxidizing agent, for example hydrogen peroxide, optionally in the presence of a catalytically effective amount of an acid catalyst.
    Type: Grant
    Filed: January 10, 1994
    Date of Patent: May 9, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Daniel Manaut, Daniel Michelet
  • 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: 5387724
    Abstract: Phenols, and related aromatic compounds, phenolic ethers, can be hydroxylated selectively using hydrogen peroxide in the presence of an amorphous or microcrystalline zirconium phosphate catalyst in a solvent containing an aliphatic carboxylic acid. The process is particularly suitable for phenol itself, and advantageously employs a partially dehydrated microcrystalline catalyst obtained by heating an hydrated microcrystalline zirconium phosphate for example at about 100.degree. C. A convenient reaction temperature is 50.degree. to 90.degree. C., and convenient solvent is acetic acid. In an improved method of producing the catalyst, zirconium phosphate is precipitated from an aqueous phosphoric acid solution of zirconium oxychloride in the presence of a cationic phase transfer agent such as an alkylpyridinium salt or tetraalkylquaternary ammonium salt or a nonionic surfactant such as an alcohol ethoxylate.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: February 7, 1995
    Assignee: Solvay Interox Limited
    Inventors: Alexander Johnstone, William R. Sanderson, Robert C. Wasson
  • 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: 5364983
    Abstract: The present invention relates to a process for the preparation of aromatic polyhydroxy compounds, by reacting an aromatic hydroxyaldehyde with hydrogen peroxide, with or without the addition of a base, in the presence of a nitrile R--CN, in which R is an alkyl radical having 1 to 4 carbon atoms or a phenyl radical, which is unsubstituted or substituted by one or more alkyl groups.
    Type: Grant
    Filed: October 7, 1993
    Date of Patent: November 15, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Laurent Weisse, Heinz Strutz
  • Patent number: 5364982
    Abstract: Hydroxylation of phenol is prone to the production of tarry by-products. Selective hydroxylation of phenol can be obtained by reacting a limited amount of hydrogen peroxide with phenol in solution in a compatible organic solvent and in the presence of a catalyst that is at least partly soluble in the reaction medium and is the salt of a heteropolyacid of general formula: i) Q.sub.3 PMo.sub.m W.sub.12-m O.sub.40 or ii) Q.sub.3+v PM.sub.n V.sub.v O.sub.40, in which Q represents a compatible organic cation, m is zero or an integer less than 6, M represents molybdenum or tungsten, v is an integer which is up to 3, and n is an integer such that n+v=12. A preferred organic cation comprises cetyl pyridinium. Selectivity towards catechol is particularly observed employing heteropolyacid salts in which m=0 in formula i) and when n=11 and M=tungsten in formula ii) and towards hydroquinone when n=11 and M=molybdenum in formula ii). Preferably the reaction medium comprises acetonitrile.
    Type: Grant
    Filed: August 3, 1993
    Date of Patent: November 15, 1994
    Assignee: Solvay Interox Limited
    Inventors: Scott W. Brown, Anthony Hackett, Angela M. King, Alexander Johnstone, William R. Sanderson
  • 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: 5292959
    Abstract: 4,4-Dinitroadamantane-2,6-dione,6, and a method of making the same.
    Type: Grant
    Filed: May 4, 1992
    Date of Patent: March 8, 1994
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Paritosh R. Dave
  • Patent number: 5276216
    Abstract: Process for oxidizing aromatic and aliphatic compounds, by using, in aqueous solution, an enzymatic system constituted by hydrogen, peroxide as the oxidizer compound, peroxidase and activated oxygen, or an enzyme which releases activated oxygen from H.sub.2 O.sub.2.In the preferred process, the enzymatic system is a double-enzyme one, in which peroxidase and catalase are used as enzymes.
    Type: Grant
    Filed: October 27, 1992
    Date of Patent: January 4, 1994
    Assignee: Ausimont S.p.A.
    Inventors: Ivan Wlassics, Fulvio Burzio
  • Patent number: 5233097
    Abstract: Certain crystalline titanoaluminosilicate molecular sieve compositions having titanium, aluminum, and silicon present as framework tetrahedral oxide units are particularly effective in hydroxylating the aromatic nucleus of aromatic compounds using hydrogen peroxide, even where the hydrogen peroxide is used at concentrations of 10 weight percent or less. The variant where the exchangeable hydrogens of the titanoaluminosilicate are replaced by an alkali or alkaline earth metal cation is particularly favored because of the concomitant increase in selectivity. Excellent utilization of hydrogen peroxide often is observed, even when the hydroxylation is effected at temperatures under about 60.degree. C.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: August 3, 1993
    Assignee: UOP
    Inventors: Laszlo T. Nemeth, Eric M. Hyatt, Thomas P. Malloy
  • Patent number: 5160497
    Abstract: Phenol production process wherein:1) benzene is reacted with propene and isopropylic alcohol by contacting a catalyst based on a dealuminized Y zeolite with a SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio ranging from 8 to 70, then the obtained product is fractionated into a first fraction comprising non converted benzene, a second fraction comprising cumene and a third fraction comprising polyisopropylbenzenes,2) said third fraction is reacted with benzene by contacting a catalyst based on a dealuminized Y zeolite with a SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio ranging from 8 to 70 or based on a dealuminized mordenite with a total Si/Al atomic ratio ranging from 20 to 60, and cumene is collected,3) the obtained cumene is converted into a mixture of acetone and phenol,4) the obtained acetone is at least partly hydrogenized into an isopropylic alcohol which is then recycled at least partly to stage 1.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: November 3, 1992
    Assignee: Institut Francais du Petrole
    Inventors: Bernard A. Juguin, Jean-Paul Boitiaux, Germain J. Martino
  • Patent number: 5110995
    Abstract: The invention relates to a process for the production of phenol or phenol derivatives by oxidation of the aromatic nucleus of benzene or benzene derivatives with nitrous oxide over a zeolite catalyst.
    Type: Grant
    Filed: March 12, 1991
    Date of Patent: May 5, 1992
    Assignee: Institute of Catalysis
    Inventors: Alexandr S. Kharitonov, Gennadii I. Panov, Kazimira G. Ione, Vyacheslav N. Romannikov, Galina A. Sheveleva, Lidia A. Vostrikova, Vladimir I. Sobolev
  • Patent number: 5097078
    Abstract: The phenols and phenol ethers are hydroxylated by reacting such phenols/phenol ethers with hydrogen peroxide, in the presence of (a) a catalytically effective amount of an alkali metal or alkaline earth metal salt of at least one protonic acid having a pKa in water of less than -0.1, and (b) an effective amount of at least one phosphorus oxyacid.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: March 17, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Dominique Laucher
  • Patent number: 5017729
    Abstract: Phenol is produced in a recycle manner by (a) reacting benzene with propylene to synthesize cumene, (b) oxidizing the cumene of step (a) into cumene hydroperoxide, (c) acid cleaving cumene hydroperoxide into phenol and acetone, (d) hydrogenating the acetone of step (c) into isopropanol, (e) dehydrating the isopropanol of step (d) into propylene, and (f) recycling the propylene of step (e) to step (a). It is also possible to take propylene from step (e). The acetone by-product produced upon preparation of phenol is converted into propylene which is useful by itself for any other uses or recycled to the phenol producing process.
    Type: Grant
    Filed: September 5, 1989
    Date of Patent: May 21, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Hiroshi Fukuhara, Fujihisa Matsunaga
  • Patent number: 5003114
    Abstract: Phenols/phenol ethers are hydroxylated by reaction with hydrogen peroxide in the presence of a catalytically effective amount of a calcined germanozeosilite MFI zeolite.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: March 26, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Michel Gubelmann, Jean-Pierre Lecomte, Jean-Michel Popa
  • Patent number: 4992600
    Abstract: The instant invention relates to a process for the oxidation of benzene to phenol which comprises contacting benzene and molecular oxygen with a dihydrodihydroxyanthracene-sulfonate salt dissolved in water, optionally in the presence of an oxidation catalyst, and subsequently separating from the reaction product phenol and the corresponding anthraquinone-sulfonate. The by-product anthraquinone is suitably recycled to the benzene oxidation step by hydrogenating the anthraquinone salt to the dihydrodihydroxyanthracene salt.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: February 12, 1991
    Assignee: Shell Oil Company
    Inventors: Kuo-Hua Chao, Raymond T. Moy
  • Patent number: 4982015
    Abstract: The instant invention relates to a process for the oxidation of benzene to phenol which comprises contacting benzene and molecular oxygen with a dihydrodihydroxynaphthoquinone, optionally in the presence of an oxidation catalyst, and subsequently separating from the reaction product phenol and the corresponding naphthoquinone. The by-product napththoquinone is suitably recycled to the benzene oxidation step by hydrogenating the naphthoquinone to the dihydrodihydroxynapththoquinone.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: January 1, 1991
    Assignee: Shell Oil Company
    Inventors: Kuo-Hua Chao, Raymond T. Moy
  • Patent number: 4962241
    Abstract: The process of the present invention for producing dihydroxynaphthalenes comprises hydrolyzing a diacyloxynaphthalene in a water-containing solvent in the presence of an acid catalyst. The use of an acid as a hydrolyzing catalyst enables dihydroxynaphthalenes to be obtained with high purity and in high yield.
    Type: Grant
    Filed: February 3, 1989
    Date of Patent: October 9, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Masaaki Yasuda, Hisaya Miki
  • Patent number: RE33779
    Abstract: 4,4'-Dihydroxybiphenyl is prepared by decomposing 4,4'-di(2-hydroxy-2-propyl)biphenyl with hydrogen peroxide and an acid catalyst in acetonitrile as a solvent. Especially, this process minimizes the formation of by-products and permits easy purification of the intended product.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: December 24, 1991
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yutaka Konai, Tadashi Nakamura, Takayuki Tanonaka, Kazuo Yoshida, Yoshihisa Machida