Preparing By Oxidation Patents (Class 568/771)
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Patent number: 5504260Abstract: 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: GrantFiled: September 9, 1994Date of Patent: April 2, 1996Assignee: Bayer AktiengesellschaftInventors: Zoltan Kricsfalussy, Helmut Waldmann, Hans-Joachim Traenckner
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Patent number: 5493061Abstract: 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: GrantFiled: December 9, 1994Date of Patent: February 20, 1996Assignee: Council of Scientific & Industrial ResearchInventors: Paul Ratnasamy, Subramanian Sivasanker
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Patent number: 5435985Abstract: 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: GrantFiled: February 8, 1994Date of Patent: July 25, 1995Assignee: Kemira OyInventors: Arto Pukkinen, Lauri Heikkinen, Rauni Ruuska
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Patent number: 5434317Abstract: 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: GrantFiled: December 9, 1993Date of Patent: July 18, 1995Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Adrien Dromard, Michel Jouffret
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Patent number: 5426244Abstract: 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: GrantFiled: May 2, 1994Date of Patent: June 20, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Ryuji Sugai, Osamu Kondo, Yuki Motoyama, Shu Yoshida
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Patent number: 5414155Abstract: 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: GrantFiled: January 10, 1994Date of Patent: May 9, 1995Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Daniel Manaut, Daniel Michelet
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Patent number: 5414153Abstract: 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: GrantFiled: April 5, 1993Date of Patent: May 9, 1995Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 5387724Abstract: 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: GrantFiled: October 12, 1993Date of Patent: February 7, 1995Assignee: Solvay Interox LimitedInventors: Alexander Johnstone, William R. Sanderson, Robert C. Wasson
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Patent number: 5364982Abstract: 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: GrantFiled: August 3, 1993Date of Patent: November 15, 1994Assignee: Solvay Interox LimitedInventors: Scott W. Brown, Anthony Hackett, Angela M. King, Alexander Johnstone, William R. Sanderson
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Patent number: 5364983Abstract: 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: GrantFiled: October 7, 1993Date of Patent: November 15, 1994Assignee: Hoechst AktiengesellschaftInventors: Laurent Weisse, Heinz Strutz
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Patent number: 5331103Abstract: 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: GrantFiled: February 26, 1993Date of Patent: July 19, 1994Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 5276216Abstract: 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: GrantFiled: October 27, 1992Date of Patent: January 4, 1994Assignee: Ausimont S.p.A.Inventors: Ivan Wlassics, Fulvio Burzio
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Patent number: 5254746Abstract: 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: GrantFiled: August 19, 1992Date of Patent: October 19, 1993Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Jean-Michel Popa, Michel Gubelmann
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Patent number: 5245086Abstract: 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: GrantFiled: December 5, 1990Date of Patent: September 14, 1993Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 5233097Abstract: 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: GrantFiled: October 15, 1992Date of Patent: August 3, 1993Assignee: UOPInventors: Laszlo T. Nemeth, Eric M. Hyatt, Thomas P. Malloy
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Patent number: 5208391Abstract: Processes for the preparation of tetracyano-1,4-hydroquinone and its conversion to tetracyano-1,4-benzoquinone via a disilver salt are disclosed.Type: GrantFiled: July 18, 1991Date of Patent: May 4, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carlos Vazquez
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Patent number: 5160496Abstract: 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: GrantFiled: July 16, 1990Date of Patent: November 3, 1992Assignee: Rhone-Poulenc ChimieInventors: Michel Constantini, Jean-Michel Popa
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Patent number: 5149888Abstract: 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: GrantFiled: February 28, 1990Date of Patent: September 22, 1992Assignee: Rone-Poulenc ChimieInventors: Michel Costantini, Eric Garcin, Michel Gubelmann, Jean-Michel Popa
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Patent number: 5138104Abstract: 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: GrantFiled: July 25, 1991Date of Patent: August 11, 1992Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Katsuji Takahashi, Misao Uohama, Takayuki Akiyama
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Patent number: 5110995Abstract: 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: GrantFiled: March 12, 1991Date of Patent: May 5, 1992Assignee: Institute of CatalysisInventors: Alexandr S. Kharitonov, Gennadii I. Panov, Kazimira G. Ione, Vyacheslav N. Romannikov, Galina A. Sheveleva, Lidia A. Vostrikova, Vladimir I. Sobolev
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Patent number: 5097078Abstract: 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: GrantFiled: July 6, 1990Date of Patent: March 17, 1992Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Dominique Laucher
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Patent number: 5095143Abstract: 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: GrantFiled: June 13, 1990Date of Patent: March 10, 1992Assignee: Amoco CorporationInventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
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Patent number: 5055623Abstract: 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: GrantFiled: June 22, 1990Date of Patent: October 8, 1991Assignee: Rhone-Poulenc ChimieInventors: Michel Gubelmann, Jean-Michel Popa, Philipe-Jean Tirel
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Patent number: 5026925Abstract: 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: GrantFiled: January 27, 1987Date of Patent: June 25, 1991Assignee: Degussa AktiengesellschaftInventors: Karl-Heinz Drauz, Axel Kleeman, Gunter Prescher, Gebhard Ritter
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Patent number: 5003114Abstract: 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: GrantFiled: June 7, 1989Date of Patent: March 26, 1991Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Michel Gubelmann, Jean-Pierre Lecomte, Jean-Michel Popa
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Patent number: 4992600Abstract: 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: GrantFiled: September 26, 1989Date of Patent: February 12, 1991Assignee: Shell Oil CompanyInventors: Kuo-Hua Chao, Raymond T. Moy
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Patent number: 4982015Abstract: 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: GrantFiled: September 26, 1989Date of Patent: January 1, 1991Assignee: Shell Oil CompanyInventors: Kuo-Hua Chao, Raymond T. Moy
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Patent number: 4982013Abstract: 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: GrantFiled: May 2, 1989Date of Patent: January 1, 1991Assignee: Rhone-Poulenc ChimieInventors: Michel Gubelmann, Philippe-Jean Tirel
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Patent number: 4954653Abstract: 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: GrantFiled: June 7, 1989Date of Patent: September 4, 1990Assignee: Enichem Sintesi S.p.A.Inventors: Giuseppe Bellussi, Franco Buonomo, Antonio Esposito, Mario Clerici, Ugo Romano, Bruno Notari
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Patent number: 4950809Abstract: 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: GrantFiled: December 8, 1988Date of Patent: August 21, 1990Assignee: Rhone-Poulenc ChimieInventor: Michel Gubelmann
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Patent number: 4933506Abstract: 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: GrantFiled: November 22, 1988Date of Patent: June 12, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Takao Ogino, Shunji Arita, Masayuki Takeda, Masaru Kaya
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Patent number: 4861921Abstract: 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: GrantFiled: March 3, 1987Date of Patent: August 29, 1989Assignee: Catalytica AssociatesInventors: Jere D. Fellmann, Robert J. Saxton, Paul Tung
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Patent number: 4849549Abstract: 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: GrantFiled: December 22, 1987Date of Patent: July 18, 1989Assignee: Indspec Chemical CorporationInventor: Ching-Yong Wu
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Patent number: 4847429Abstract: 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: GrantFiled: August 3, 1987Date of Patent: July 11, 1989Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, Bruce L. Gustafson, Dale E. Van Sickle, Joseph S. Bowers, Jr.
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Patent number: 4847436Abstract: 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: GrantFiled: December 22, 1987Date of Patent: July 11, 1989Assignee: Indspec Chemical CorporationInventor: Ching-Yong Wu
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Patent number: 4847437Abstract: 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: GrantFiled: December 22, 1987Date of Patent: July 11, 1989Assignee: Indspec Chemical CorporationInventor: Ching-Yong Wu
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Patent number: 4835325Abstract: 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: GrantFiled: March 25, 1988Date of Patent: May 30, 1989Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hisaya Miki, Shintarou Araki, Masatoshi Nitabaru
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Patent number: 4825011Abstract: 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: GrantFiled: December 4, 1987Date of Patent: April 25, 1989Assignee: Degussa AGInventors: Karl-Heinz Drauz, Axel Kleeman, Gunter Prescher, Gebhard Ritter
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Patent number: 4814521Abstract: 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: GrantFiled: August 26, 1987Date of Patent: March 21, 1989Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Takayuki Tanonaka, Takashi Yamauchi, Hiroyuki Enari, Yutaka Konai
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Patent number: 4804788Abstract: 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: GrantFiled: November 4, 1987Date of Patent: February 14, 1989Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yutaka Konai, Tadashi Nakamura, Takayuki Tanonaka, Kazuo Yoshida, Yoshihisa Machida
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Patent number: 4801758Abstract: 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: GrantFiled: May 18, 1987Date of Patent: January 31, 1989Assignee: Neste OyInventors: Salme Koskimies, Taru Haimala
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Patent number: 4762953Abstract: 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: GrantFiled: February 26, 1987Date of Patent: August 9, 1988Assignee: Degussa AktiengesellschaftInventors: Guenter Prescher, Gebhard Ritter, Holger Sauerstein
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Patent number: 4760199Abstract: 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: GrantFiled: August 4, 1987Date of Patent: July 26, 1988Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Axel Kleemann
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Patent number: 4751333Abstract: 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: GrantFiled: February 26, 1987Date of Patent: June 14, 1988Assignee: Degussa AktiengesellschaftInventors: Guenter Prescher, Gebhard Ritter, Holger Sauerstein
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Patent number: 4751332Abstract: 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: GrantFiled: September 14, 1987Date of Patent: June 14, 1988Assignee: Degussa AktiengesellschaftInventors: Guenter Prescher, Gebhard Ritter, Holger Sauerstein
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Patent number: 4718994Abstract: 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: GrantFiled: June 14, 1985Date of Patent: January 12, 1988Assignee: Latviisky Gosudarstvenny Universaitet Imeni P. StuchkiInventors: Andrei K. Zhagars, Voldemar Y. Grinshtein, Sniedzite A. Ozola, Andris K. Zitsmanis, Avgust K. Arens
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Patent number: 4686010Abstract: 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: GrantFiled: September 7, 1984Date of Patent: August 11, 1987Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Axel Kleemann
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Patent number: 4670609Abstract: 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: GrantFiled: September 29, 1982Date of Patent: June 2, 1987Assignee: The Goodyear Tire & Rubber CompanyInventors: Ronald Q. Bennett, Donald E. Smith, Joel Muse, Jr.
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Patent number: 4628126Abstract: 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: GrantFiled: March 12, 1984Date of Patent: December 9, 1986Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Axel Kleemann
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Patent number: RE33779Abstract: 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: GrantFiled: August 13, 1990Date of Patent: December 24, 1991Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yutaka Konai, Tadashi Nakamura, Takayuki Tanonaka, Kazuo Yoshida, Yoshihisa Machida