Preparing By Hydroxylation Of Benzene Ring Patents (Class 568/629)
  • Patent number: 9630899
    Abstract: The present disclosure relates to an improved, environmentally friendly, process for producing compounds such as hydroquinone (benzene-1,4-diol) and its derivatives. The process can be carried out at ambient temperature and pressure using a recyclable copper catalyst and recyclable intermediate materials. The process generally entails reacting an aromatic compound such as benzene with hydrogen peroxide in the present of a pure elemental copper catalyst or a copper (I) salt catalyst to form oxidation product such as benzoquinone, and reducing the compound to hydroquinone or a hydroquinone derivative.
    Type: Grant
    Filed: October 26, 2015
    Date of Patent: April 25, 2017
    Assignee: Chang Chun Plastics Co. Ltd.
    Inventors: Chien Fu Huang, Yi Hung Chou
  • Publication number: 20150045580
    Abstract: Selectively fluorinated molecules are important as materials, pharmaceuticals, and agrochemicals, but their synthesis by simple, mild, laboratory methods is challenging. We report a straightforward method for the cross-coupling of a difluoromethyl group with readily available reagents to form difluoromethylarenes. The reaction of electron-neutral, electronrich, and sterically hindered aryl and vinyl iodides with the combination of Cul, CsF and TMSCF2H leads to the formation of difluoromethylarenes in high yield with good functional group compatibility. This transformation is surprising, in part, because of the prior observation of the instability of CuCF2H.
    Type: Application
    Filed: March 5, 2013
    Publication date: February 12, 2015
    Inventors: John Hartwig, Patrick Fier
  • 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: 20140073818
    Abstract: A method for hydroxylating phenols and phenol ethers using hydrogen peroxide and specifically, a method for hydroxylating phenol using hydrogen peroxide. The method for hydroxylating a phenolic substrate selected from a phenol or a phenol ether by reacting such phenolic substrate with hydrogen peroxide in the presence of an acid catalyst comprises the following steps, implemented consecutively or simultaneously: a first step consisting of mixing a phenolic substrate with a hydrogen peroxide solution under conditions in which the temperature is sufficient for the initial phenolic substrate to remain liquid and for minimizing the conversion rate of the hydrogen peroxide; a second step consisting of carrying out the phenolic substrate hydroxylation reaction under adiabatic conditions, the acid catalyst being added at the mixing stage and/or at the beginning of the hydroxylation reaction; and a third step, if necessary, consisting of recovering the hydroxylated product.
    Type: Application
    Filed: May 15, 2012
    Publication date: March 13, 2014
    Applicant: RHODIA OPERATIONS
    Inventors: Laurent Garel, Stephanie Normand, Pascal Pitiot, Jean-Christophe Bigouraux
  • Publication number: 20130211102
    Abstract: The present invention relates to the scaled-up synthesis of biologically active compounds which display useful therapeutic activity in treating proliferative disorders. In particular the invention relates to process methods for the kilogram scale synthesis of a particular class of substituted benzofuran tubulin polymerisation inhibitors.
    Type: Application
    Filed: July 15, 2011
    Publication date: August 15, 2013
    Applicant: BIONOMICS LIMITED
    Inventor: Bernard Luke Flynn
  • 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
  • Publication number: 20100286451
    Abstract: The present invention relates to a process for producing a 2-fluoro-6-halophenol as an intermediate; a process for producing a 2-alkoxy-3-fluorophenol and further a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; a second process for producing a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; and a 2-alkoxy-3-fluorophenol. The 2-fluoro-6-halophenol can be obtained using a 2-fluorophenol as a starting material and through a sulfonation reaction, a halogenation reaction, and a deprotection reaction. The 2-fluoro-6-halophenol is alkyl-etherified, and subsequently the halogen atom is converted into a hydroxyl group to obtain the 2-alkoxy-3-fluorophenol, which is further alkyl-etherified to thereby obtain the 1,2-dialkoxy-3-fluorobenzene. Alternatively, a 1,2-dialkoxy-3-fluorobenzene is also obtained by converting the halogen atom of the 2-fluoro-6-halophenol into a hydroxyl group to thereby form 3-fluorocatechol and subsequently alkyl-etherifying two hydroxyl groups thereof.
    Type: Application
    Filed: July 14, 2010
    Publication date: November 11, 2010
    Inventors: Mingjian Qiu, Wei Zhang, Zhaohui Chen, Chunshan Zhang, Yali Zhang
  • Patent number: 7828991
    Abstract: This invention relates to novel polyether polyols which are prepared by alkoxylation of renewable resource materials, and particularly cashew nutshell liquid (CNSL), and to a process for the preparation of these novel polyether polyols. This invention also relates to flexible polyurethane foams prepared from these long chain polyether polyols, and to a process for the production of these flexible polyurethane foams.
    Type: Grant
    Filed: December 8, 2006
    Date of Patent: November 9, 2010
    Assignee: Bayer MaterialScience LLC
    Inventors: Jack R. Reese, Micah N. Moore, Don S. Wardius, Stanley L. Hager
  • Patent number: 7786330
    Abstract: The present invention relates to a process for producing a 2-fluoro-6-halophenol as an intermediate; a process for producing a 2-alkoxy-3-fluorophenol and further a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; a second process for producing a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; and a 2-alkoxy-3-fluorophenol. The 2-fluoro-6-halophenol can be obtained using a 2-fluorophenol as a starting material and through a sulfonation reaction, a halogenation reaction, and a deprotection reaction. The 2-fluoro-6-halophenol is alkyl-etherified, and subsequently the halogen atom is converted into a hydroxyl group to obtain the 2-alkoxy-3-fluorophenol, which is further alkyl-etherified to thereby obtain the 1,2-dialkoxy-3-fluorobenzene. Alternatively, a 1,2-dialkoxy-3-fluorobenzene is also obtained by converting the halogen atom of the 2-fluoro-6-halophenol into a hydroxyl group to thereby form 3-fluorocatechol and subsequently alkyl-etherifying two hydroxyl groups thereof.
    Type: Grant
    Filed: February 24, 2009
    Date of Patent: August 31, 2010
    Assignees: Asahi Glass Company, Limited, Charna Chemicals, Ltd.
    Inventors: Mingjian Qiu, Wei Zhang, Zhaohui Chen, Chunshan Zhang, Yali Zhang
  • Patent number: 7781622
    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: Grant
    Filed: October 30, 2008
    Date of Patent: August 24, 2010
    Assignee: Council of Scientific & Industrial Research
    Inventors: Suman Lata Jain, Jomy K. Joseph, Sweety Singhal, Bir Sain, Ragunathan Sivakumaran, Basant Kumar
  • Patent number: 7625499
    Abstract: The present invention provides a conductive liquid-crystal material having features including that, for example, excellent conductivity is exhibited at a low threshold voltage of about 5 V even in a room temperature range, the value of resistance varies with an applied voltage, the current density rises sharply at a voltage of about 5 V, and an excellent charge mobility is exhibited, as well as a process for producing the conductive liquid-crystal material, a liquid-crystal composition which is used for the conductive liquid-crystal material, a liquid-crystal semiconductor element, and an information recording medium.
    Type: Grant
    Filed: November 30, 2005
    Date of Patent: December 1, 2009
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventor: Yuichiro Haramoto
  • Patent number: 7482494
    Abstract: The present invention provides a benzene derivative having a long, linear conjugated structure, the benzene derivative being capable of exhibiting a satisfactory ability to transport charge without photoexcitation, a process for producing the benzene derivative, and a liquid-crystal material and a charge-transport material containing the benzene derivative having a long, linear conjugated structure. That is, a benzene derivative having a long, linear conjugated structure represented by general formula (1): (wherein R1 represents a methyl group or a hydrogen atom, A represents an alkylene group, —CO—O—(CH2)n—, —C6H4—CH2—, or —CO—).
    Type: Grant
    Filed: March 22, 2004
    Date of Patent: January 27, 2009
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventor: Yuichiro Haramoto
  • Patent number: 7414157
    Abstract: The present invention pertains to a process for preparing a compound of Formula I that is achiral, racemic or enantiomerically enriched at the hydroxylation center indicated by comprising contacting a compound of Formula II with an oxidant selected from oxygen, hydrogen peroxide, peracids or alkyl hydroperoxides in the presence of a zirconium complex, wherein R1, R2 and R3 are as defined in the disclosure. This invention also pertains to zirconium complexes useful in this procedure comprising zirconium and a ligand of Formula III or its enantiomer wherein J, R6 and n are as defined in the disclosure. This invention further pertains to a compound of Formula III or its enantiomer.
    Type: Grant
    Filed: June 6, 2002
    Date of Patent: August 19, 2008
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Albert Loren Casalnuovo
  • Patent number: 7393465
    Abstract: A process for preparing hydrophobic polyols that includes reacting A) a mixture having an OH content of from 180 to 300 mg KOH/g, a viscosity at 23° C. of from 5000 to 20 000 mPas and an OH functionality of from 2.8 to 4.5 including from 5 to 20 wt. % of 3-pentadecadienylphenol, from 5 to 10 wt. % of 3-pentadecadienyl-recorcinol and from 1 to 5 wt. % of 2-methyl 3-pentadecadienylrecorcinol; with B) alkylene oxides (AO) with addition of the AO monomers onto the AO-reactive groups of component A); the ratio of the amounts of A) to B) being from 1:9 to 9:1; where the hydrophobic polyols have an OH number of from 140 to 220 mg KOH/g and a viscosity at 23° C. of from 1000 to 4000 mPas. The hydrophobic polyols can be used in polyurethane systems, in coatings, adhesive bonds, sealants or moulding compounds, which can be used to coat substrates.
    Type: Grant
    Filed: February 24, 2005
    Date of Patent: July 1, 2008
    Assignee: Bayer MaterialScience AG
    Inventors: Meike Niesten, Jack Reese, Joachim Simon, Gerhard Ruttmann
  • Patent number: 6977236
    Abstract: The present invention relates to a process for the preparation of a double metal cyanide (DMC) catalyst, which process involves: (a) combining an aqueous solution of metal salt with an aqueous solution of a metal cyanide salt and reacting these solutions; and (b) recovering the DMC catalyst from the reaction mixture, in which process the DMC catalyst is prepared in the presence of from 0.03 to 0.4 mole of alkaline metal compound, based on amount of metal salt. Further, the present invention relates to DMC catalyst obtainable by such process, to DMC catalyst prepared from a metal salt and a metal cyanide salt in which the molar ratio of metal derived from the metal salt to metal derived from the metal cyanide salt is at least 2.25 and to a process for polymerization of alkylene oxides which process involves reacting initiator with alkylene oxide in the presence of at most 15 ppm of DMC catalyst.
    Type: Grant
    Filed: February 17, 2004
    Date of Patent: December 20, 2005
    Assignee: Shell Oil Company
    Inventors: Michiel Barend Eleveld, Robert Adrianus Wilhelmus Grotenbreg, Ronald van Kempen
  • Patent number: 6765079
    Abstract: Novel cross linked polymer films prepared from poly4-[(4-cardanylazo]benzoic acid and poly4-[(4-acryloylcardanylazo]benzoic acid are disclosed. The invention also relates to novel monomers 4-[(4-cardanylazo] benzoic acid and 4-[(4-acryloylcardanylazo] benzoic acid and polymers thereof as well processes for the preparation thereof.
    Type: Grant
    Filed: March 24, 2003
    Date of Patent: July 20, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Muthusamy Saminathan, Chennakkattu Krishna Sadasivan Pillai
  • Patent number: 6756512
    Abstract: The invention relates to a novel process for preparing 2-alkyl-3-chlorophenols.
    Type: Grant
    Filed: October 30, 2002
    Date of Patent: June 29, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Hübsch, Reinhard Lantzsch, Thorsten Müh, Holger Weintritt
  • 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
  • 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
  • Patent number: 6229054
    Abstract: The present invention comprises a process for the hydroxyalkylation of cardanol with cyclic organic carbonates in the presence of organic or inorganic catalysts and a novel composition of matter produced by that process. The unique molecular structure of cardanol allows the use of a variety of organic or inorganic basic catalysts, including triethylamine, imidazol, sodium hydroxide and sodium carbonate, in the hydroxyalkylation reaction without forming quantities of undesirable side-products. According to this invention, the final product, monohydroxyalkylcardanyl ether, can be obtained with high yield and high purity. The product has a light color and its color stability is enhanced by replacing the phenol's hydroxyl group with a more stable hydroxyalkoxyl group.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: May 8, 2001
    Assignee: Cardolite Corporation
    Inventors: Zhisheng Dai, Meng J. Chen
  • Patent number: 6156939
    Abstract: The invention relates to a process for the hydroxylation of aromatic hydrocarbons by direct oxidation with hydrogen peroxide. The process is carried out in the presence of a catalyst comprising:iron, administered as inorganic salt;iron ligand, consisting of carboxylic acids of ether-aromatic compounds containing nitrogen, in particular pyrazin-2-carboxylic acid and derivatives;acidifying agent, especially trifluoracetic acid, and a solvent system comprising an organic phase consisting of a substrate and acetonitrile and an aqueous phase containing the catalyst and hydrogen peroxide.
    Type: Grant
    Filed: April 4, 2000
    Date of Patent: December 5, 2000
    Assignee: Enichem S.p.A.
    Inventors: Rodolfo Vignola, Ezio Battistel, Daniele Bianchi, Rossella Bortolo, Roberto Tassinari
  • Patent number: 5811592
    Abstract: Described are compounds defined according to the structure: ##STR1## wherein Z represents meta or para cyclohexylene or meta or para phenylene and wherein R.sub.1 and R.sub.2 are the same or different methyl or hydrogen; and wherein R.sub.3 represents C.sub.1 -C.sub.3 alkyl; and wherein the moiety: ##STR2## is ortho with respect to R.sub.2 and para or meta with respect to the moiety: ##STR3## with the proviso that the sum of the number of carbon atoms in R.sub.1, R.sub.2 and R.sub.3 is 3 or 4; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations; as well as processes for preparing alkyl-substituted-C.sub.1 -C.sub.3 alkoxy-C.sub.6 -cycloaliphatic compounds.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: September 22, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael G. Monteleone, Richard A. Weiss, Marc D. Evans, Marie R. Hanna
  • Patent number: 5786519
    Abstract: An improved process is provided for the preparation of a mixture of guaiacol and p-methoxy phenol which comprises reacting anisole 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 groups, and isolating the mixture of guaiacol and p-methoxy phenol formed.
    Type: Grant
    Filed: February 16, 1996
    Date of Patent: July 28, 1998
    Assignee: Council of Scientific & Industrial Research
    Inventors: Pramod Prabhakar Moghe, Paul Ratnasamy, Robert Raja, Ashwini Vinayak Pol, Madhav Gopal Kotasthane, Prakash Kondiba Bahirat
  • Patent number: 5688975
    Abstract: Molecular sieve compositions have been synthesized which are resistant to the loss of framework atoms. Specifically, the molecular sieves of the invention have the empirical formulamA: (M.sub.w Al.sub.x Si.sub.y)O.sub.2where A is at least one rare earth metal, M is chromium or titanium and "m", "w", "x" and "y" are the mole fractions of A, M, Al and Si respectively. Applicants have discovered that the rare earth metals prevent loss of chromium and titanium from the framework and degradation of the molecular sieve. Along with the composition, a process for preparing the composition and processes using the composition are disclosed and claimed.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: November 18, 1997
    Assignee: UOP
    Inventors: Vinayan Nair, Deng-Yang Jan, Robert Lyle Patton, Ben A. Wilson, Donald F. Best
  • Patent number: 5658927
    Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: August 19, 1997
    Assignee: Research Corporation Technologies
    Inventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
  • Patent number: 5658951
    Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: August 19, 1997
    Assignee: Research Corporation Technologies
    Inventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
  • Patent number: 5602283
    Abstract: A multistage process of preparing N-alkyl-3,4-dialkyl-2,6-dinitroanilines starts from 3,4-dialkyl phenol and goes through the stages of 3,4-dialkyl-2,6-dinitrophenol and 3,4-dialkyl-2,6-ditro alkoxybenzene, wherein the latter are new compounds.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: February 11, 1997
    Assignee: Agan Chemical Manufacturers Ltd.
    Inventor: Morris Sarel
  • Patent number: 5416235
    Abstract: A process for the preparation of aromatic compounds of the general formula I,Ar--X Iin which Ar represents an optionally substituted aryl group and X represents a group OH, Cl, Br or CN, by reaction of an aryl diazoniumsalt of the formula II,Ar--N.dbd.N.sup.+ Y.sup.- IIin which Ar is as defined above and Y represents a suitable counterion, with water, hydrogen chloride or a salt thereof, hydrogen bromide or a salt thereof, or a cyanide in the presence of a copper(I)salt, characterized in that the copper(I)salt is a copper(I)salt derived from an hydroxy carboxylic acid.
    Type: Grant
    Filed: November 1, 1993
    Date of Patent: May 16, 1995
    Assignee: Octel Chemicals Limited
    Inventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
  • Patent number: 5414153
    Abstract: Phenolic compounds, e.g., the phenols and phenol ethers, are selectively hydroxylated whereby the amounts of the final product para isomer are enhanced, for example in favor of hydroquinone versus pyrocatechol in the event of the hydroxylation of phenol, by reacting such phenolic compounds with hydrogen peroxide, advantageously in a polar, aprotic, organic solvent reaction medium, in the presence of a catalytically effective amount of a sulfonated polymer and a cocatalytically effective amount of an aromatic ketone compound.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: May 9, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Dominique Laucher
  • Patent number: 5360938
    Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: November 1, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James E. Babin, Gregory T. Whiteker
  • Patent number: 5254746
    Abstract: The phenols and phenol ethers are hydroxylated by reaction with hydrogen peroxide in the presence of a catalytically effective amount of a titanozeosilite, advantageously a silicon oxide/titanium oxide MFI zeolite having the general formula:SI.sub.(96-x), Ti.sub.x O.sub.192.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: October 19, 1993
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Jean-Michel Popa, Michel Gubelmann
  • Patent number: 5245086
    Abstract: The phenols/phenol ethers are hydroxylated by reaction with hydrogen peroxide, in the presence of a catalytically effective amount of (a) at least one alkali metal or alkaline earth metal salt of a protonic acid having a pKa in water of less than -0.1 and (b) a free protonic acid.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: September 14, 1993
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Dominique Laucher
  • 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: 5160496
    Abstract: The phenols and phenol ethers are economically and efficiently hydroxylated using hydrogen peroxide, in the presence of a catalytically effective amount of a bridged clay, e.g., a zeolite or smectite.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: November 3, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Constantini, Jean-Michel Popa
  • Patent number: 5149888
    Abstract: The phenols and phenol ethers, e.g., phenol itself, are effectively hydroxylated by reacting hydrogen peroxide therewith, in the presence of a catalytically effective amount of titanium dioxide.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: September 22, 1992
    Assignee: Rone-Poulenc Chimie
    Inventors: Michel Costantini, Eric Garcin, Michel Gubelmann, Jean-Michel Popa
  • Patent number: 4954653
    Abstract: The invention discloses a catalyst on the basis of silicon and titanium having the form of microspheres and constituted by oligomeric silica and by titanium-silica-lite crystals having an oligomeric silica/titanium-silicalite molar ratio comprised within the range of from 0.05 to 0.11, wherein the crystals of titanium-silicalite are encaged by means of Si-O-Si bridges.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: September 4, 1990
    Assignee: Enichem Sintesi S.p.A.
    Inventors: Giuseppe Bellussi, Franco Buonomo, Antonio Esposito, Mario Clerici, Ugo Romano, Bruno Notari
  • Patent number: 4814521
    Abstract: Disclosed herein is a process for producing 2,6-dihydroxynaphthalene which comprises oxidizing 2,6-di(2-hydroxy-2-propyl)naphthalene in acetonitrile, 1,4-dioxane or a mixture thereof with hydrogen peroxide in the presence of an inorganic acid or a solid acid at a temperture in the range of room temperature to the boiling point of the solution of the 2,6-di(2-hydroxy-2-propyl)naphthalene in acetonitrile or 1,4-dioxane, the acetonitrile, 1,4-dioxane or a mixture thereof being used in an amount of 3 to 30 ml to one gram of the 2,6-di(2-hydroxy-2-propyl)naphthalene.
    Type: Grant
    Filed: August 26, 1987
    Date of Patent: March 21, 1989
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Takayuki Tanonaka, Takashi Yamauchi, Hiroyuki Enari, Yutaka Konai
  • Patent number: 4551562
    Abstract: The nuclear hydroxylation of phenol with organic solutions of hydrogen peroxide in the presence of a catalyst is carried out in improved manner by employing both (1) a special, practically water free solution of hydrogen peroxide in an organic solvent which does not form an azeotrope with water or whose highest azeotrope with water, boil near or above the boiling point of hydrogen peroxide, and (2) employing as a catalyst XO.sub.2 where X is sulfur, selenium, or tellurium. Besides increasing the yield and the ability to carry out the reaction in a simpler manner when selenium dioxide is employed as a catalyst, there can also be controlled the ortho-para ratio, respectively, the ortho-ortho ratio of the product.
    Type: Grant
    Filed: March 13, 1984
    Date of Patent: November 5, 1985
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karlheinz Drauz, Axel Kleemann
  • Patent number: 4533766
    Abstract: The known nuclear hydroxylation of substituted phenols or phenol ethers with organic solutions of hydrogen peroxide in the presence of a catalyst is carried out in improved manner by employing both (1) a special, practically water free solution of hydrogen peroxide in an organic solvent which forms an azeotrope with water, which azeotrope boils below the boiling point of hydrogen peroxide, and (2) sulfur dioxide as a catalyst. Through this, the nuclear hydroxylation is substantially simpler than previously; difficult separations, e.g., from water-phenol, or the separation and recovery of the catalyst are eliminated. Besides, the yields are increased.
    Type: Grant
    Filed: March 8, 1984
    Date of Patent: August 6, 1985
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karlheinz Drauz, Axel Kleemann
  • Patent number: 4422955
    Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula --O--R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: December 27, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Robert J. Bryant
  • Patent number: 4301307
    Abstract: Aromatic hydrocarbons and particularly phenols and phenol ethers can be hydroxylated by reacting the aromatic compound with hydrogen peroxide in a reaction medium comprising trifluoromethanesulfonic acid. High yields of hydroxylated aromatic compounds are obtained by this process which avoids the use of extremely corrosive and difficult to handle agents. Phenol is hydroxylated predominantly to hydroquinone by this process.
    Type: Grant
    Filed: December 20, 1979
    Date of Patent: November 17, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Michel Jouffret
  • Patent number: 4174460
    Abstract: A process for the hydroxylation of phenols and phenol ethers in the nucleus with hydrogen peroxide wherein a phenol or a phenol ether is reacted at the start of the reaction with substantially anhydrous hydrogen peroxide and wherein the reaction is carried out in the presence of a strong acid.
    Type: Grant
    Filed: March 31, 1977
    Date of Patent: November 13, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Seifert, Helmut Waldman, Wulf Schwerdtel, Wolfgang Swodenk