Preparing By Oxidation Patents (Class 568/771)
  • 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: 5493061
    Abstract: This invention relates to a process for the oxidation of phenol to a mixture of hydroquinone and catechol using hydrogen peroxide as oxidant in the presence of titanium silicate molecular sieves in a multistage fixed bed reactor.
    Type: Grant
    Filed: December 9, 1994
    Date of Patent: February 20, 1996
    Assignee: Council of Scientific & Industrial Research
    Inventors: Paul Ratnasamy, Subramanian Sivasanker
  • Patent number: 5435985
    Abstract: The invention relates to a hydrogenation catalyst for use in the preparation of hydrogen peroxide and to a method for the preparation of the catalyst. The hydrogenation catalyst contains in the main platinum group metal, of which more than 50 wt % is palladium. According to the invention, at least one additional metal is added to the platinum group metal.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: July 25, 1995
    Assignee: Kemira Oy
    Inventors: Arto Pukkinen, Lauri Heikkinen, Rauni Ruuska
  • Patent number: 5434317
    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: December 9, 1993
    Date of Patent: July 18, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Adrien Dromard, Michel Jouffret
  • 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: 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: 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: 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: 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: 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: 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: 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: 5208391
    Abstract: Processes for the preparation of tetracyano-1,4-hydroquinone and its conversion to tetracyano-1,4-benzoquinone via a disilver salt are disclosed.
    Type: Grant
    Filed: July 18, 1991
    Date of Patent: May 4, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carlos Vazquez
  • 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: 5138104
    Abstract: A process for producing dihydric phenols is disclosed. The process comprises reacting a phenol with a ketone peroxide or a combination of a ketone and hydrogen peroxide in the presence of a compound having at least one P-S bond. Dihydric phenols can be produced in high yield without requiring neutralization after the reaction.
    Type: Grant
    Filed: July 25, 1991
    Date of Patent: August 11, 1992
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Katsuji Takahashi, Misao Uohama, Takayuki Akiyama
  • 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: 5095143
    Abstract: A method to oxidize an oxidizable component in a liquid phase with an oxygen-containing gas is disclosed. The method comprises mixing the liquid phase and gas phase in a reactor with a rotating agitator element operated at constant power.
    Type: Grant
    Filed: June 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Amoco Corporation
    Inventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
  • Patent number: 5055623
    Abstract: Phenol/substituted phenols are prepared by directly hydroxylating an aromatic substrate with nitrous oxide, in vapor phase, in the presence of a modified (acidified) ZSM-5 or ZSM-11 zeolite, containing such elements as Ga, Fe, B, In, Cr, Sc, Co, Ni, Be, Zn, Cu, Sb, As or V.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: October 8, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Gubelmann, Jean-Michel Popa, Philipe-Jean Tirel
  • Patent number: 5026925
    Abstract: The nuclear hydroxylation of phenol can be carried out in an industrially very simple manner and with at least the yields obtained with the known methods as well as with very good selectivities by means of using aqueous hydrogen peroxide with the simultaneous addition of sulfur dioxide or selenium dioxide as catalyst.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: June 25, 1991
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karl-Heinz Drauz, Axel Kleeman, Gunter Prescher, Gebhard Ritter
  • 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: 4982013
    Abstract: Polyhydroxybenzenes, e.g., the dihydroxybenzenes, are prepared by directly hydroxylating a phenol with nitrous oxide, preferably in vapor phase, on a substrate of acidified zeolite particulates, advantageously ZSM-5 zeolite particulates, and such acidified zeolite particulates advantageously having a molar ratio SiO.sub.2 /Al.sub.2 O.sub.3 of greater than about 90, preferably up to 500.
    Type: Grant
    Filed: May 2, 1989
    Date of Patent: January 1, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Gubelmann, Philippe-Jean Tirel
  • 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: 4950809
    Abstract: A process for preparing a hydroxylated aromatic compound by the Baeyer-Villiger reaction. In a first stage, a solution of peracetic acid is formed. In a second stage, an aryl ketone and/or an aromatic aldehyde is contacted with the above solution for a time sufficient to obtain the hydroxylated aromatic compound. The hydroxylated compound obtained can be used in the pharmaceutical, plant-protection or polymer chemical industries.
    Type: Grant
    Filed: December 8, 1988
    Date of Patent: August 21, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventor: Michel Gubelmann
  • Patent number: 4933506
    Abstract: A process for the production of dihydric phenoles by oxidizing diisopropylbenzenes, which comprises oxidizing diisopropylbenzenes with molecular oxygen to obtain a reaction product mixture (A) containing at least diisopropylbenzene dihydroperoxide (DHP) and diisopropylbenzene monocarbinol monohydroperoxide (HHP), supply said product mixture (A) in a form of oily phase as a solution in an aromatic hydrocarbon solvent to an agitation reactor, supplying thereto at the same time, as an aqueous phase, hydrogen peroxide at a feed rate of 1-5 moles per mole of HHP contained in the product mixture and an acid catalyst in an amount sufficient to reach a concentration in the aqueous phase of 10-40% by weight, the concentration of hydrogen peroxide in the aqueous phase being maintained at a value of at least 20% by weight and the weight ratio of the oily phase/aqueous phase being at least 10, causing oxidization of the HHP into DHP by hydrogen peroxide while maintaining the reaction temperature at 30.degree.-60.degree.
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: June 12, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Takao Ogino, Shunji Arita, Masayuki Takeda, Masaru Kaya
  • Patent number: 4861921
    Abstract: A process for the manufacture of resorcinol is described which relies upon the intermediacy of a .alpha.,.beta.-unsaturated ketone which can be reacted with a hydroxy moiety-containing compound to obtain a resorcinol precursor which is subsequently converted to resorcinol. In a specific embodiment, 2-cyclohexenone is reacted dehydrogenated to resorcinol. In antoher embodiment, 2-cyclohexenone is oxidized to cyclohexane-1,3-dione which is dehydragenated obtain resorcinol.
    Type: Grant
    Filed: March 3, 1987
    Date of Patent: August 29, 1989
    Assignee: Catalytica Associates
    Inventors: Jere D. Fellmann, Robert J. Saxton, Paul Tung
  • Patent number: 4849549
    Abstract: A process for the preparation of resorcinol from diisopropylbenzene includes the steps of oxidizing m-diisopropylbenzene under anhydrous, non-alkaline conditions with oxygen, extracting m-diisopropylbenzene dihydroperoxide and m-diisopropylbenzene hydroxyhydroperoxide with dilute sodium hydroxide, re-extracting with an organic solvent, converting m-diisopropylbenzene hydroxyhydroperoxide to m-diisopropylbenzene dihydroperoxide with hydrogen peroxide, drying the product, decomposing the m-diisopropylbenzene dihydroperoxide in the presence of a catalyst selected from the group consisting of boron trifluoride, ferric chloride and stannic chloride to coproduce resorcinol and actone, and purifying the resorcinol.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: July 18, 1989
    Assignee: Indspec Chemical Corporation
    Inventor: Ching-Yong Wu
  • Patent number: 4847429
    Abstract: Process is disclosed for the preparation of phenylhydroquinones by the alkylation of hydroquinone (or derivatives thereof) with the cyclohexyl moieties, cyclohexanol or cyclohexene (or derivatives thereof), followed by dehydrogenation of the intermediate cyclohexylhydroquinone.
    Type: Grant
    Filed: August 3, 1987
    Date of Patent: July 11, 1989
    Assignee: Eastman Kodak Company
    Inventors: Carl M. Lentz, Bruce L. Gustafson, Dale E. Van Sickle, Joseph S. Bowers, Jr.
  • Patent number: 4847436
    Abstract: An improvement in the preparation of resorcinol includes the decomposition of m-diisopropylbenzene dihydroperoxide (m-DHP) to resorcinol and acetone in the presence of an effective amount of a catalyst selected from the group consisting of boron trifluoride, ferric chloride and stannic chloride. Minute quantities of the catalyst, preferably 10 to 50 ppm, are effective to increase the yields of resorcinol.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: July 11, 1989
    Assignee: Indspec Chemical Corporation
    Inventor: Ching-Yong Wu
  • Patent number: 4847437
    Abstract: An improvement in a process for the preparation of resorcinol which includes the steps of treating an extract of selected oxidation products of diisopropylbenzene with hydrogen peroxide to convert m-HHP to m-DHP, drying the treated extract and thereafter, decomposing the m-DHP in the presence of an effective amount, preferably within the range of about 10 to 50 ppm, of a catalyst selected from the group consisting of boron trifluoride, ferric chloride and stannic chloride.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: July 11, 1989
    Assignee: Indspec Chemical Corporation
    Inventor: Ching-Yong Wu
  • Patent number: 4835325
    Abstract: Hydroxybenzenes can be produced in high yield through a one-step reaction by subjecting (a) an .alpha.,.alpha.-dialkyl-.alpha.-hydroxymethyl group containing benzene and/or (b) a benzene containing both .alpha.,.alpha.-dialkyl-.alpha.-hydroxymethyl and .alpha.,.alpha.-dialkyl-.alpha.-hydroperoxymethyl groups to reaction in the presence of a nitrile, an acid and hydrogen peroxide. In a preferred mode, the reaction system further contains (c) an .alpha.,.alpha.-dialkyl-.alpha.-hydroperoxymethyl group containing benzene.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: May 30, 1989
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Hisaya Miki, Shintarou Araki, Masatoshi Nitabaru
  • Patent number: 4825011
    Abstract: The nuclear hydroxylation of substituted phenols is performed by using aqueous hydrogen peroxide in the presence of sulfur dioxide or selenium dioxide as catalyst in a simple manner with very good space-time yields and good product yields.
    Type: Grant
    Filed: December 4, 1987
    Date of Patent: April 25, 1989
    Assignee: Degussa AG
    Inventors: Karl-Heinz Drauz, Axel Kleeman, Gunter Prescher, Gebhard Ritter
  • 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: 4804788
    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 byproducts and permits easy purification of the intended product.
    Type: Grant
    Filed: November 4, 1987
    Date of Patent: February 14, 1989
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yutaka Konai, Tadashi Nakamura, Takayuki Tanonaka, Kazuo Yoshida, Yoshihisa Machida
  • Patent number: 4801758
    Abstract: A procedure for producing hydroquinone from a hydrocarbon mixture obtained as a by-product when producing cumene, by selectively oxidizing tertiary alkylaromatics to form hydroperoxides, by separating the dihydroperoxide of p-diisopropylbenzene from the oxidation product by selective crystallization through cooling, and by decomposing the dihydroperoxide of p-diisopropylbenzene with the aid of an acid catalyst to form the hydroquinone.
    Type: Grant
    Filed: May 18, 1987
    Date of Patent: January 31, 1989
    Assignee: Neste Oy
    Inventors: Salme Koskimies, Taru Haimala
  • Patent number: 4762953
    Abstract: A method for the production of substituted 1,2,3- and 1,2,4-trihydroxybenzenes in a single process reaction step, wherein the corresponding substituted resorcinol which is a substituted 1,3-dihydroxybenzene is contacted with an aqueous hydrogen peroxide solution and through control of the water content of the initial reaction condition and control of the reaction temperature the desired products are obtained.
    Type: Grant
    Filed: February 26, 1987
    Date of Patent: August 9, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenter Prescher, Gebhard Ritter, Holger Sauerstein
  • Patent number: 4760199
    Abstract: The production of solutions of hydrogen peroxide in phenol or its derivatives, e.g. hydrocarbyl substituted phenols, halo substituted phenols or phenol ethers, is carried out in a single step. Practically no loss of hydrogen peroxide occurs since a total distillation of hydrogen peroxide together with phenol or phenol derivative is avoided. Simultaneously the solutions obtained are practically free from water. The mixture of phenol or phenol derivative and aqueous hydrogen peroxide is treated with a material that boils below the boiling point of hydrogen peroxide, phenol or phenol derivative or forms an azeotrope with water that boils below the boiling point of hydrogen peroxide, phenol or phenol derivative and the water removed as an azeotrope. The solution of hydrogen peroxide in phenol or phenol derivative which remains behind is suitable for carrying out oxidation reactions and above all, also for hydroxylation reactions.
    Type: Grant
    Filed: August 4, 1987
    Date of Patent: July 26, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karlheinz Drauz, Axel Kleemann
  • Patent number: 4751333
    Abstract: Method for the conversion of resorcinol with aqueous hydrogen peroxide to obtain a mixture of 1,2,3- and 1,2,4-trihydroxybenzenes wherein the amount of water present in the initial reaction mixture is controlled to small amounts.
    Type: Grant
    Filed: February 26, 1987
    Date of Patent: June 14, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenter Prescher, Gebhard Ritter, Holger Sauerstein
  • Patent number: 4751332
    Abstract: Resorcinol and substituted resorcinols are converted in one single step reaction into 1,2,3- and 1,2,4-trihydroxybenzenes and substituted hydroxy resorcinol compounds with a benzene solution of peroxypropionic acid.
    Type: Grant
    Filed: September 14, 1987
    Date of Patent: June 14, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenter Prescher, Gebhard Ritter, Holger Sauerstein
  • Patent number: 4718994
    Abstract: A method for perparing hydroxy compounds of the aromatic and heteroaromatic series of the general formula: ##STR1## wherein when R.sub.1 .dbd.--COOH, --CH.sub.2 CH(NH.sub.2)COOH then R.sub.2 .dbd.--OH, --H, --COOH; R.sub.3 .dbd.--H, --OH; R.sub.4, R.sub.5 .dbd.--H with no connecting bond; R.sub.6 .dbd.--OH; and when R.sub.1,R.sub.6,R.sub.3 .dbd.--H, R.sub.2 .dbd.--OH; then R.sub.4 .dbd.>NH; R.sub.5 .dbd.--CR.sub.7 .dbd.CHR.sub.4, where R.sub.7 .dbd.--CH.sub.2 --CH.sub.2 --NH.sub.2, --CH.sub.2 --CH(NH.sub.2)COOH, consists in that aromatic and heteroaromatic compounds of the general formula ##STR2## wherein when R.sub.1 .dbd.--COOH, --CH.sub.2 CH(NH.sub.2)COOH, then R.sub.2 .dbd.--OH, --H, --COOH; R.sub.3 .dbd.--H, --OH; R.sub.4,R.sub.5 .dbd.--H with no connecting bond; and when R.sub.1,R.sub.2,R.sub.3 .dbd.--H, then R.sub.4 .dbd.>NH; R.sub.5 .dbd.--CR.sub.7 .dbd.CHR.sub.4, where R.sub.7 .dbd.--CH.sub.2 --CH.sub.2 --NH.sub.2, --CH.sub.2 --CH(NH.sub.2)COOH.
    Type: Grant
    Filed: June 14, 1985
    Date of Patent: January 12, 1988
    Assignee: Latviisky Gosudarstvenny Universaitet Imeni P. Stuchki
    Inventors: Andrei K. Zhagars, Voldemar Y. Grinshtein, Sniedzite A. Ozola, Andris K. Zitsmanis, Avgust K. Arens
  • Patent number: 4686010
    Abstract: The production of solutions of hydrogen peroxide in phenol or its derivatives, e.g. hydrocarbyl substituted phenols, halo substituted phenols or phenol ethers, is carried out in a single step. Practically no loss of hydrogen peroxide occurs since a total distillation of hydrogen peroxide together with phenol or phenol derivative is avoided. Simultaneously the solutions obtained are practically free from water. The mixture of phenol or phenol derivative and aqueous hydrogen peroxide is treated with a material that boils below the boiling point of hydrogen peroxide, phenol or phenol derivative or forms an azeotrope with water that boils below the boiling point of hydrogen peroxide, phenol or phenol derivative and the water removed as an azeotrope. The solution of hydrogen peroxide in phenol or phenol derivative which remains behind is suitable for carrying out oxidation reactions and above all, also for hydroxylation reactions.
    Type: Grant
    Filed: September 7, 1984
    Date of Patent: August 11, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karlheinz Drauz, Axel Kleemann
  • Patent number: 4670609
    Abstract: An improved process for the manufacture of a dihydric phenol such as hydroquinone wherein a dialkylbenzene is oxidized to a dihydroperoxide, the dihydroperoxide being extracted from the oxidate by a caustic solution, leaving an organic phase for recycle to the oxidizer, the improvement comprising decreasing the caustic concentration in the recycle organic phase and increasing the dihydroperoxide concentration of the recycle phase by washing the organic phase from the caustic extract with an aqueous phase removed from the oxidizer, separating the organic phase from the aqueous phase and subsequently introducing the organic phase to the oxidizer.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: June 2, 1987
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Ronald Q. Bennett, Donald E. Smith, Joel Muse, Jr.
  • Patent number: 4628126
    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 12, 1984
    Date of Patent: December 9, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karlheinz Drauz, Axel Kleemann
  • 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