Preparing By Oxidation Patents (Class 568/771)
  • Patent number: 9376359
    Abstract: Disclosed herein is a process for preparing an isomeric mixture comprising a major amount of a para-linear mono-alkyl-substituted hydroxyaromatic compound.
    Type: Grant
    Filed: October 31, 2013
    Date of Patent: June 28, 2016
    Assignee: Chevron Oronite Company LLC
    Inventors: Cedrick Mahieux, Curtis B. Campbell, Alexander E. Kuperman
  • Patent number: 8957260
    Abstract: The invention relates to a process for the oxidation of mesitol with singlet oxygen, which is released from hydrogen peroxide, this release taking place in the presence of a bismuth compound as catalyst. In the process, 2,4,6-trimethylquinol is formed in high yield and selectivity as product, which can be used in further reactions for the synthesis of vitamins and in particular of vitamin A and vitamin E.
    Type: Grant
    Filed: February 2, 2012
    Date of Patent: February 17, 2015
    Assignee: BASF SE
    Inventors: Martine Weis, Joaquim Henrique Teles, Klaus Ebel, Peter Deglmann, Vivien Ellinor Weyrauch, Gunhild Weyrauch
  • Publication number: 20140296544
    Abstract: The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C—H bonds and one or more activated C—H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C—H bonds; oxidizing selectively one of the one or more aromatic C—H bonds in preference to the one or more activated C—H bonds; adding a hydroxyl group to the one of the one or more aromatic C—H bonds to form one or more phenols; and purifying the one or more phenols.
    Type: Application
    Filed: August 14, 2013
    Publication date: October 2, 2014
    Inventors: Dionicio Siegel, Andrew M. Camelio, Anders Eliasen, Trevor C. Johnson, Abram Axelrod, Changxia Yuan
  • Publication number: 20140221698
    Abstract: The present invention relates to a method for the hydroxylation of phenols and phenol ethers by means of hydrogen peroxide. The invention specifically relates to a method for the hydroxylation of phenol by means of the hydrogen peroxide. The method of the invention for the hydroxylation of a phenol ether by means of reacting said phenol or phenol ether with the hydrogen peroxide in the presence of an acid catalyst is characterized in that it includes mixing a phenol or phenol ether with a hydrogen peroxide solution in a mixing device under conditions enabling the conversion rate of the hydrogen peroxide to be minimized, and in that said reaction mixture is then placed in a piston flow reactor where the reaction leading to the production of the hydroxylated material takes place, the acid catalyst being fed into the mixing device and/or into the piston flow reactor.
    Type: Application
    Filed: February 15, 2012
    Publication date: August 7, 2014
    Applicant: RHODIA OPERATIONS
    Inventors: Laurent Garel, Jean-Christophe Bigouraux, Stéphanie Normand, Pascal Pitiot
  • Patent number: 8791308
    Abstract: A process for the hydroxylation of phenols and of phenol ethers by hydrogen peroxide is described. More particularly a process for the hydroxylation of phenol by hydrogen peroxide is described. The described process can include hydroxylation of a phenol or of a phenol ether having at least one hydrogen atom at the ortho and para position of the hydroxyl group or of the ether group, by reaction of said phenol or phenol ether, with hydrogen peroxide, in the presence of an acid catalyst, wherein the reaction is carried out in the presence of an effective amount of a catalyst which is a mixture of at least two strong acids and wherein one of the acids is chosen from strong protonic acids and the other acid is chosen from superacids.
    Type: Grant
    Filed: March 30, 2010
    Date of Patent: July 29, 2014
    Assignee: Rhodia Operations
    Inventor: Laurent Garel
  • Publication number: 20140179956
    Abstract: A method for preparing catechol is provided. The method includes performing hydroxylation of phenol by using zirconium-containing titanium silicalite as a catalyst in the presence of phenol, a solvent and hydrogen peroxide. The method uses zirconium-containing titanium silicalite as a catalyst to increase the selectivity of phenol and utilization of hydrogen peroxide, and thus to increase the overall reaction yield.
    Type: Application
    Filed: December 11, 2013
    Publication date: June 26, 2014
    Applicant: China Petrochemical Development Corporation, Taipei (Taiwan)
    Inventors: I-Hui Lin, Cheng-Fa Hsieh, Pin-To Yao
  • Publication number: 20120203013
    Abstract: The invention relates to a process for the oxidation of mesitol with singlet oxygen, which is released from hydrogen peroxide, this release taking place in the presence of a bismuth compound as catalyst. In the process, 2,4,6-trimethylquinol is formed in high yield and selectivity as product, which can be used in further reactions for the synthesis of vitamins and in particular of vitamin A and vitamin E.
    Type: Application
    Filed: February 2, 2012
    Publication date: August 9, 2012
    Applicant: BASF SE
    Inventors: Jan Philipp Weyrauch, Martine Weis, Joaquim Henrique Teles, Klaus Ebel, Peter Deglmann, Vivien Ellinor Weyrauch, Gundhild Weyrauch
  • Publication number: 20120035397
    Abstract: A process for the hydroxylation of phenols and of phenol ethers by hydrogen peroxide is described. More particularly a process for the hydroxylation of phenol by hydrogen peroxide is described. The described process can include hydroxylation of a phenol or of a phenol ether having at least one hydrogen atom at the ortho and para position of the hydroxyl group or of the ether group, by reaction of said phenol or phenol ether, with hydrogen peroxide, in the presence of an acid catalyst, wherein the reaction is carried out in the presence of an effective amount of a catalyst which is a mixture of at least two strong acids and wherein one of the acids is chosen from strong protonic acids and the other acid is chosen from superacids.
    Type: Application
    Filed: March 30, 2010
    Publication date: February 9, 2012
    Applicant: RHODIA OPERATIONS
    Inventor: Laurent Garel
  • Patent number: 7906667
    Abstract: A method for producing an optically active alcohol compound comprising reacting a cyclic ether compound with a phenol compound in the presence of an asymmetric complex obtained by reacting an optically active metal complex represented by the formula (1): wherein R1, R2, R3, R4, R5, R6, R7 and R8 are the same or different and each independently represent a hydrogen atom, an alkyl group or the like; one of R9 and R10 is a hydrogen group and the other is a substituted or unsubstituted phenyl group or the like; Q represents a single bond, a C1-C4 alkylene group or the like; M represents a metal ion; and when an ionic valency of the metal ion is same as a coordination number of a ligand, A is nonexistent, and when the above-mentioned ionic valency is different from the coordination number, and A represents a counter ion or a ligand, with a metal sulfonate.
    Type: Grant
    Filed: January 31, 2007
    Date of Patent: March 15, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Kazuaki Sasaki
  • Publication number: 20100174105
    Abstract: The present disclosure is directed to the production of 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate and the purification thereof. Synthesis pathways for a precursor to 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate are provided. The precursor is 5-tert-butyl-3-methylcatechol.
    Type: Application
    Filed: December 31, 2009
    Publication date: July 8, 2010
    Inventors: Tak W. Leung, Gary A. Roth, Tao Tao, Kuanqiang Gao, Linfeng Chen
  • Patent number: 7714175
    Abstract: According to the present invention, two hydroxyl groups can be introduced into the 1-position and the 4-position of the benzene ring of an aromatic compound highly efficiently and highly selectively by a one step process to give the corresponding aromatic hydroxide. The present invention provides a production method of an aromatic hydroxide represented by the formula (2) wherein R1, R2, R3, and, R4 are each independently a hydrogen atom or an alkyl group having a carbon atom number of 1-20, and R1, R2 and/or R3 and R4 are optionally bonded to each other to form a ring, which comprises irradiating light to a photoelectrode comprised of metal oxide while applying a given potential in the presence of an aromatic compound represented by the formula (1) wherein R1, R2, R3, and R4 are as defined above.
    Type: Grant
    Filed: March 27, 2009
    Date of Patent: May 11, 2010
    Assignees: Sumitomo Chemical Company, Limited, National University Corporation Hokkaido University
    Inventors: Ryu Abe, Bunsho Ohtani, Osamu Tomita
  • Publication number: 20090192337
    Abstract: The present invention provides a process for direct hydroxylation of aromatic hydrocarbons like benzene to phenol, toluene to cresols and anisole to methoxy phenols by using hydrogen peroxide as environmentally benign oxidant in polar solvent like acetonitrile using vanadium phthalocyanine or its derivative as a catalyst, at a temperature in the range of 25-100° C.
    Type: Application
    Filed: October 30, 2008
    Publication date: July 30, 2009
    Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
    Inventors: Suman Lata JAIN, Jomy K. JOSEPH, Sweety SINGHAL, Bir SAIN, Ragunathan SIVAKUMARAN, Basant KUMAR
  • Patent number: 7557252
    Abstract: A process for simultaneously producing a dihydroxybenzene and a diisopropylbenzene dicarbinol, which contains subjecting a diisopropylbenzene with an oxygen containing gas to obtain an oxidation reaction mixture containing a diisopropylbenzene dihydroperoxide and a diisopropylbenzene hydroxy hydroperoxide followed by an extraction separation step, a decomposition step, a distillation separation step, a reduction step and a post-treatment step in this order, the process containing purifying the diisopropylbenzene dicarbinol from the liquid containing the diisopropylbenzene dicarbinol obtained in the reduction step through purification operations containing crystallization, filtration and subsequent drying, and supplying a filtrate obtained by the filtration to the decomposition step and/or distillation separation step.
    Type: Grant
    Filed: February 12, 2007
    Date of Patent: July 7, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Mamoru Seino
  • Publication number: 20080227984
    Abstract: This invention relates to the selective oxidation of organic compounds. According to the invention organic compounds are selectively oxidized using a peracid or a source of peracid, a transition metal based heterogeneous catalysts and a borate or boric acid in the presence of water. Using the process of the present invention, both excellent conversion and product selectivity maybe obtained.
    Type: Application
    Filed: October 21, 2005
    Publication date: September 18, 2008
    Applicant: U.S. Borax, Inc.
    Inventors: Michael John Greenhill-Hooper, Robert Raja, John Meurig-Thomas
  • Patent number: 7148386
    Abstract: A process for the preparation of hydroquinone compounds comprising, reacting an aromatic hydroxy compound with an oxidizing agent in a biphasic solvent system. The reaction is carried out in the presence of a transition metal hydroxy phosphate catalyst to produce the corresponding hydroquinone compound.
    Type: Grant
    Filed: July 30, 2004
    Date of Patent: December 12, 2006
    Assignee: General Electric Company
    Inventors: Jegadeesh Thampi, Sunil Ashtekar, Pramod Kumbhar, Rathinam Jothi Mahalingam
  • Patent number: 6930219
    Abstract: A process for treating organic compounds includes providing a composition which includes a substantially mesoporous structure of silica containing at least 97% by volume of pores having a pore size ranging from about 15 ? to about 30 ? and having a micropore volume of at least about 0.01 cc/g, wherein the mesoporous structure has incorporated therewith at least about 0.02% by weight of at least one catalytically and/or chemically active heteroatom selected from the group consisting of Al, Ti, V, Cr, Zn, Fe, Sn, Mo, Ga, Ni, Co, In, Zr, Mn, Cu, Mg, Pd, Pt and W, and the catalyst has an X-ray diffraction pattern with one peak at 0.3° to about 3.5° at 2?. The catalyst is contacted with an organic feed under reaction conditions wherein the treating process is selected from alkylation, acylation, oligomerization, selective oxidation, hydrotreating, isomerization, demetalation, catalytic dewaxing, hydroxylation, hydrogenation, ammoximation, isomerization, dehydrogenation, cracking and adsorption.
    Type: Grant
    Filed: December 6, 2002
    Date of Patent: August 16, 2005
    Assignee: ABB Lummus Global Inc.
    Inventors: Zhiping Shan, Jacobus Cornelius Jansen, Chuen Y. Yeh, Philip J. Angevine, Thomas Maschmeyer, Mohamed S. Hamdy
  • 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: 6872857
    Abstract: The present invention relates to a process for the conversion of phenol to hydroquinone and quinones. More particularly this invention relates to a process for the oxidation of phenol to a mixture of 1,4-benzoquinone and hydroquinone using an oxidant in the presence of titanium superoxide as a reusable catalyst in a liquid phase condition.
    Type: Grant
    Filed: September 29, 2003
    Date of Patent: March 29, 2005
    Assignee: Council of Scientific and Industrial Research
    Inventors: Gajanan Kundali Dewkar, Vinay Vijayraj Thakur, Sanjeevani Amrit Pardhy, Arumugam Sudalai, Sukumar Devotta
  • Publication number: 20030203460
    Abstract: A bioengineered synthesis scheme for the production of quinic acid from a carbon source is provided. Methods of producing quinic acid from a carbon source based on the synthesis scheme as well as conversion of quinic acid to hydroquinone are also provided.
    Type: Application
    Filed: May 9, 2003
    Publication date: October 30, 2003
    Inventors: John W. Frost, Karen M. Frost
  • Patent number: 6573413
    Abstract: A method for catalytic production of hydroxylated aromatics by exposing zeolite catalyst to a reducing atmosphere to activate said catalyst, and reacting an aromatic with nitrous oxide in the presence of said activated catalyst.
    Type: Grant
    Filed: April 18, 2001
    Date of Patent: June 3, 2003
    Assignee: Solutia Inc.
    Inventors: Valery S. Chernyavsky, Alexander Sergeevich Kharitonov, Gennady I. Panov, Konstantin A. Dubkov
  • Patent number: 6531615
    Abstract: This invention relates to a composition comprising antimony trifluoride and silica, a method for the preparation of said composition and use of said composition as a catalyst in a process for the oxidation of cyclohexanone to &egr;-caprolactone.
    Type: Grant
    Filed: January 30, 2001
    Date of Patent: March 11, 2003
    Assignee: Solvay (Societe Anonyme)
    Inventors: Michael C. Rocca, Graham Carr, Arnold B. Lambert, Duncan J. MacQuarrie, James H. Clark
  • 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: 6441250
    Abstract: There are disclosed a process for producing a dihydric phenol which comprises oxidizing a monohydric phenol by a peroxide compound in the presence of a &bgr;-zeolite, a ketone and a phosphoric acid, and a process for producing a dihydric phenol which comprises oxidizing a monohydric phenol in the presence of a &bgr;-zeolite, a ketone and a phosphoric acid, by feeding a monohydric phenol, hydrogen peroxide, a ketone and a phosphoric acid into a reactor in which a &bgr;-zeolite is charged, to oxidize the monohydric phenol into a dihydric phenol, and delivering the resultant reaction mixture from the reactor.
    Type: Grant
    Filed: June 19, 2001
    Date of Patent: August 27, 2002
    Assignee: UBE Industries, Ltd.
    Inventors: Takashi Atoguchi, Shigeru Yao, Tomonori Kanougi
  • Patent number: 6441249
    Abstract: An inexpensive method for producing trimethylhydroquinone free from the problem of the disposal of waste catalyst, which method comprises the steps of: (1) reacting isophorone in the presence of an acid catalyst and recovering &bgr;-isophorone by distiiulation, (2) oxidizing the &bgr;-isophorone in the presence of amorphous carbon and a base to obtain 4-oxoisophorone, (3) reacting the 4-oxoisophorone with an acid anhydride in a liquid phase or with a carboxylic acid in a vapor phase in the presence of a solid acid catalyst to obtain trimethylhydroquinones, and (4) hydrolyzing the trimethylhydroquinones to obtaining trimethylhydroquinone.
    Type: Grant
    Filed: June 18, 2001
    Date of Patent: August 27, 2002
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Kazuharu Suyama, Noboru Kiyota, Tomohiro Konishi, Yasuo Matsumura
  • Patent number: 6423877
    Abstract: The present invention is directed to a new synthetic route to pseudopterosin aglycone (3): a key intermediate for the synthesis of a group of antiinflammatory natural products including pseudopterosin A (1) and E (2). The pathway of synthesis starts with the abundant and inexpensive (S)-(−)-limonene and its long-known cyclic hydroboration product (4) and leads to the chiral hydroxy ketone (6). Conversion of (6) to (10) followed by a novel aromatic annulation produced (15) which underwent highly diastereoselective cyclization to afford the protected pseudopterosin aglycone (16). The naturally occurring pseudopterosins such as (1) and (2) are readily available from this key intermediate.
    Type: Grant
    Filed: November 15, 2000
    Date of Patent: July 23, 2002
    Assignee: President and Fellows of Harvard College
    Inventor: Elias J. Corey
  • Patent number: 6414197
    Abstract: A method and a catalyst are described for selective oxidation of aromatic compounds (e.g., benzene and its derivatives) into hydroxylated aromatic compounds (e.g., corresponding phenols). For example, benzene can be converted into phenol with a yield of at least 30-40%, and a selectivity on the basis of benzene of at least 95-97%. The selectivity for this reaction based on N2O is at least 90-95%. Therefore, no substantial N2O decomposition or consumption for complete benzene oxidation to CO+CO2 or other side products occurs. Similar results are obtained with benzene derivatives (e.g., fluorobenzene, difluorobenzene, phenol), although the selectivity is somewhat lower in the case of derivatives (e.g., about 80-85% in the case of fluorosubstituted benzenes). A preferred catalyst for this process is a composition containing a high-silica pentasil-type zeolite (e.g, an HZSM-5 type zeolite) which contains no purposefully introduced additives such as transition or noble metals.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: July 2, 2002
    Assignee: General Electric Company
    Inventors: Leonid Modestovich Kustov, Viktor Ignatyevich Bogdan, Vladimir Borisovich Kazansky
  • Publication number: 20020040168
    Abstract: A method and a catalyst are described for selective oxidation of aromatic compounds (e.g., benzene and its derivatives) into hydroxylated aromatic compounds (e.g., corresponding phenols). For example, benzene can be converted into phenol with a yield of at least 30-40%, and a selectivity on the basis of benzene of at least 95-97%. The selectivity for this reaction based on N2O is at least 90-95%. Therefore, no substantial N2O decomposition or consumption for complete benzene oxidation to CO+CO2 or other side products occurs. Similar results are obtained with benzene derivatives (e.g., fluorobenzene, difluorobenzene, phenol), although the selectivity is somewhat lower in the case of derivatives (e.g., about 80-85% in the case of fluorosubstituted benzenes). A preferred catalyst for this process is a composition containing a high-silica pentasil-type zeolite (e.g, an HZSM-5 type zeolite) which contains no purposefully introduced additives such as transition or noble metals.
    Type: Application
    Filed: May 13, 1998
    Publication date: April 4, 2002
    Inventors: LEONID MODESTOVICH KUSTOV, VIKTOR IGNATYEVICH BOGDAN, VLADIMIR BORISOVICH KAZANSKY
  • Patent number: 6350921
    Abstract: Improved methods for the simultaneous production of dihydroxybenzene and dicarbinol from diisopropylbenzene are provided. These methods provide for continuous and simultaneous production of diisopropylbenzene dihydroperoxide (DHP) and diisopropylbenzene hydroxyhydroperoxide (HHP) using Karr Column extractors operated in series. A very high purity DHP-containing solution, the precursor to the dihydroxybenzene, can be produced according to the reported methods. A safe and efficient method for producing dicarbinol from HHP is also disclosed.
    Type: Grant
    Filed: February 24, 1998
    Date of Patent: February 26, 2002
    Assignee: Indspec Chemical Corporation
    Inventors: Raj B. Durairaj, Vaughn J. Romell, Michael N. Tackie, Thomas K. Volek
  • Patent number: 6320086
    Abstract: An inexpensive method for producing trimethylhydroquinone free from the problem of the disposal of waste catalyst, which method comprises the steps of: (1) reacting isophorone in the presence of an acid catalyst and recovering &bgr;-isophorone by distillation, (2) oxidizing the &bgr;-isophorone in the presence of amorphous carbon and a base to obtain 4-oxoisophorone, (3) reacting the 4-oxoisophorone with an acid anhydride in a liquid phase or with a carboxylic acid in a vapor phase in the presence of a solid acid catalyst to obtain trimethylhydroquinones, and (4) hydrolyzing the trimethylhydroquinones to obtaining trimethylhydroquinone.
    Type: Grant
    Filed: May 17, 2000
    Date of Patent: November 20, 2001
    Assignee: Nippon Petrochemicals Company Limited
    Inventors: Kazuharu Suyama, Noboru Kiyota, Tomohiro Konishi, Yasuo Matsumura
  • Publication number: 20010039365
    Abstract: A method and composition are disclosed for the hydroxylation of aromatic substrates in the presence of oxygen, hydrogen, and a catalyst. In a preferred embodiment, benzene is oxidized to phenol in the presence of oxygen, a vanadium catalyst, and hydrogen. The method is economical, safe, and amenable to commercial scale-up.
    Type: Application
    Filed: January 16, 2001
    Publication date: November 8, 2001
    Inventor: Terence Michael Barnhart
  • Publication number: 20010039366
    Abstract: An inexpensive method for producing trimethylhydroquinone free from the problem of the disposal of waste catalyst, which method comprises the steps of: (1) reacting isophorone in the presence of an acid catalyst and recovering &bgr;-isophorone by distiiulation, (2) oxidizing the &bgr;-isophorone in the presence of amorphous carbon and a base to obtain 4-oxoisophorone, (3) reacting the 4-oxoisophorone with an acid anhydride in a liquid phase or with a carboxylic acid in a vapor phase in the presence of a solid acid catalyst to obtain trimethylhydroquinones, and (4) hydrolyzing the trimethylhydroquinones to obtaining trimethylhydroquinone.
    Type: Application
    Filed: June 18, 2001
    Publication date: November 8, 2001
    Applicant: Nippon Petrochemicals Company Limited
    Inventors: Kazuharu Suyama, Noboru Kiyota, Tomohiro Konishi, Yasuo Matsumura
  • Patent number: 6262315
    Abstract: A dihydric phenolic compound is produced, with a high selectivity thereof, by a plurality of oxidation reactors connected to each other in series, by (1) feeding a monohydric phenolic compound with a temperature of 30 to 100° C.
    Type: Grant
    Filed: May 26, 1999
    Date of Patent: July 17, 2001
    Assignee: Ube Industries, Ltd.
    Inventors: Yukio Inaba, Kazunori Fujita, Hiroshi Kofuji
  • Publication number: 20010004673
    Abstract: There are provided:
    Type: Application
    Filed: December 7, 2000
    Publication date: June 21, 2001
    Inventors: Tomoyuki Noritake, Shigeru Goto, Kenji Itoh
  • Patent number: 6080895
    Abstract: An improved process for producing a catechol derivative (1) useful as a intermediate of pharmaceuticals and agricultural chemicals, being shown by the following reaction scheme. The process is characterized in that formulation in the first step is carried out in the two stages, that is, the reaction is carried out in the presence of a tin catalyst at 60-85.degree. C. to a conversion of 30 to 80% and then is completed at 95-105.degree. C. to produce a salicylaldehyde derivative (3) in a high yield and a high selectivity. Thereby, the objective catechol derivative (1) can be obtained in a high yield and with a high purity. ##STR1## In the above formula, R is alkyl, cycloalkyl, aralkyl, alkoxy, halogen atom, allyl, or aryl, and R.sup.1 is a hydroxy protective group.
    Type: Grant
    Filed: June 19, 1998
    Date of Patent: June 27, 2000
    Assignee: Daiso Co., Ltd.
    Inventors: Yoshiro Furukawa, Keishi Takenaka
  • Patent number: 6040484
    Abstract: The present invention relates to a process for the hydroxylation of phenolic compounds and, more particularly, to a process for the hydroxylation of phenols and phenolic ethers with hydrogen peroxide. The invention relates to a process for the hydroxylation of phenolic compounds using hydrogen peroxide, said process being characterized in that the reaction is carried out in the presence of an effective quantity of at least one rare earth or bismuth triflate.
    Type: Grant
    Filed: August 13, 1998
    Date of Patent: March 21, 2000
    Assignee: Rhodia Chimie
    Inventors: Michel Costantini, Laurent Gilbert, Michel Spagnol
  • Patent number: 5985927
    Abstract: Medicinal products for the selective control of tumor tissue and a method for control of such tumor tissue by administration of such product to a host. The products comprise: (a) two different compounds having a pH below 7 when the compounds are present in a protonated form, such compounds having the formula set forth below and (b) a pharmaceutically acceptable inert medicinal product carrier. The compounds have the following ##STR1## wherein R.sub.1 is hydrogen or a moiety which completes an ester group or an ether group, R.sub.2 is independently selected from the group consisting of an amino group, hydroxyl, an ester group, an ether group and a halogen, and n is an integer of 1 to 4.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: November 16, 1999
    Inventor: Werner Kreutz
  • Patent number: 5892132
    Abstract: A continuous process for converting benzene or a derivative thereof to phenol or a derivative thereof comprises continuously activating .alpha.-sites on a zeolite catalyst by contacting the catalyst with a free oxidant activator, thereby producing an activated zeolite hydroxylation catalyst, and separately and continuously contacting benzene or a derivative thereof with the activated zeolite catalyst, thereby producing phenol or a derivative thereof.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: April 6, 1999
    Assignee: Solutia Inc.
    Inventors: Charles W. Rooks, Anthony K. Uriarte, Michael J. Gross
  • Patent number: 5874596
    Abstract: A titanosilicate catalyst and method for preparing the same, comprising primary titanosilicate particles which are combined with one another, wherein the titanosilicate catalyst comprises pores having a pore diameter of from 50 to 300 .ANG.. The inventive catalyst exhibits activity in a hydroxylation reaction of an aromatic compound, or an epoxidation reaction of an olefin, or an ammoximation reaction of a ketone using hydrogen peroxide as an oxidant.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: February 23, 1999
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takashi Onozawa, Osamu Kondo
  • Patent number: 5874646
    Abstract: In a process for converting an aromatic compound such as benzene into its hydroxylated derivative, generation of carbon monoxide during catalyst regeneration is reduced if the catalyst is a zeolite that contains ruthenium, rhodium, platinum, palladium, or irridium.
    Type: Grant
    Filed: August 7, 1996
    Date of Patent: February 23, 1999
    Assignee: Solutia Inc.
    Inventors: Jerry R. Ebner, Timothy R. Felthouse, Denton C. Fentress
  • 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: 5811587
    Abstract: The present invention concerns a process for the hydroxyalkylation of a carbocyclic aromatic ether.The invention preferably relates to the preparation of 3-methoxy-4-hydroxybenzyl alcohol by the hydroxymethylation of guaiacol.It also concerns the oxidation of the hydroxyalkylated ethers obtained, in particular the oxidation of 3-methoxy-4-hydroxybenzyl alcohol to 3-methoxy-4-hydroxybenzaldehyde, commonly known as "vanillin".The process for the hydroxyalkylation of a carbocyclic aromatic ether of the invention consists of reacting the aromatic ether with a carbonyl compound in the presence of a catalyst and is characterized in that the hydroxyalkylation reaction is carried out in the presence of an effective quantity of a zeolite.
    Type: Grant
    Filed: January 23, 1997
    Date of Patent: September 22, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Claude Moreau, Sylvie Razigade-Trousselier, Annie Finiels, Francois Fajula, Laurent Gilbert
  • Patent number: 5714641
    Abstract: Phenolic compounds, e.g., phenol, are hydroxylated, preponderantly into the para-isomer, e.g., hydroquinone, by reaction with hydrogen peroxide in the presence of an effective amount of a strong acid and a catalytically effective amount of a keto compound having the formula (II): ##STR1## in which R.sub.1 and R.sub.2, which may be identical or different, are each a hydrogen atom or an electron-donating group; n.sub.1 and n.sub.2, which may be identical or different, are numbers equal to 0, 1, 2 or 3, with the proviso that the two carbon atoms located at the .alpha.-position with respect to the two carbon atoms bearing the --CO group may be bonded together via a valence bond or via a --CH.sub.2 -- group, thereby forming a keto-containing ring member which may either be saturated or unsaturated.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: February 3, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Adrien Dromard, Michel Jouffret
  • Patent number: 5675042
    Abstract: Phenols, and related aromatic compounds, phenolic ethers, can be hydroxylated selectively using hydrogen peroxide in the presence of an amorphous or crystalline tin or cerium phosphate catalyst in a solvent containing an aliphatic carboxylic acid. The process is particularly suitable for phenol itself, and advantageously employs a catalyst obtained by heating an hydrated amorphous or crystalline tin or cerium phosphate for example at about 100.degree. C. A convenient hydroxylation temperature is in the range of 50.degree. to 90.degree. C., and a convenient solvent is acetic acid.
    Type: Grant
    Filed: August 3, 1995
    Date of Patent: October 7, 1997
    Assignee: Solvay Interox Limited
    Inventor: Robert Alexander Walker Johnstone
  • Patent number: 5672777
    Abstract: Zeolite catalysts useful for the production of phenol and its derivatives by oxidative hydroxylation of benzene and its derivatives by nitrous oxide, e.g. at temperatures of 225.degree.-450.degree. C., having substantially enhanced process characteristics resulting from hydrothermal treatment using a gas containing from about 3 to 100 mole percent water vapor, e.g. in nitrogen, at a temperature ranging from about 500.degree. to 1000.degree. C. Two hours of hydrothermal treatment has been shown to be effective.
    Type: Grant
    Filed: February 28, 1996
    Date of Patent: September 30, 1997
    Assignee: Monsanto Company
    Inventors: Alexander Sergeevich Kharitonov, Gennady Ivanovich Panov, Galina Anatolievna Sheveleva, Larisa Vladimirovna Pirutko, Tatyana Pavlovna Voskresenskaya, Vladimir Ivanovich Sobolev
  • 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: 5585526
    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: December 17, 1996
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Daniel Manaut, Daniel Michelet
  • Patent number: 5578744
    Abstract: A catalytically active gel is described consisting of a silica matrix with uniform porosity, monomodal pore distribution and high surface area, within which one or metal oxides possessing catalytic activity are dispersed. A process for preparing this catalytic gel is also described.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: November 26, 1996
    Assignees: Eniricerche S.p.A., Snamprogetti S.p.A.
    Inventors: Angela Carati, Enrico Davini, Mario G. Clerici, Giuseppe Bellussi
  • Patent number: 5559274
    Abstract: Phenol is produced from a hydrocarbon feedstock using a process combination offering unexpected synergy. Benzene is produced from the hydrocarbon feedstock using a highly selective aromatization catalyst which provides substantial quantities of high-purity hydrogen. The hydrogen is converted to hydrogen peroxide, which in turn is used to convert the benzene to phenol in high yield.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: September 24, 1996
    Assignee: UOP
    Inventors: John I. Hammerman, Peter R. Pujado
  • 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