Preparing By Oxidation Patents (Class 568/800)
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Patent number: 6080895Abstract: An improved process for producing a catechol derivative (1) useful as a intermediate of pharmaceuticals and agricultural chemicals, being shown by the following reaction scheme. The process is characterized in that formulation in the first step is carried out in the two stages, that is, the reaction is carried out in the presence of a tin catalyst at 60-85.degree. C. to a conversion of 30 to 80% and then is completed at 95-105.degree. C. to produce a salicylaldehyde derivative (3) in a high yield and a high selectivity. Thereby, the objective catechol derivative (1) can be obtained in a high yield and with a high purity. ##STR1## In the above formula, R is alkyl, cycloalkyl, aralkyl, alkoxy, halogen atom, allyl, or aryl, and R.sup.1 is a hydroxy protective group.Type: GrantFiled: June 19, 1998Date of Patent: June 27, 2000Assignee: Daiso Co., Ltd.Inventors: Yoshiro Furukawa, Keishi Takenaka
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Patent number: 5892132Abstract: A continuous process for converting benzene or a derivative thereof to phenol or a derivative thereof comprises continuously activating .alpha.-sites on a zeolite catalyst by contacting the catalyst with a free oxidant activator, thereby producing an activated zeolite hydroxylation catalyst, and separately and continuously contacting benzene or a derivative thereof with the activated zeolite catalyst, thereby producing phenol or a derivative thereof.Type: GrantFiled: August 8, 1996Date of Patent: April 6, 1999Assignee: Solutia Inc.Inventors: Charles W. Rooks, Anthony K. Uriarte, Michael J. Gross
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Patent number: 5874646Abstract: In a process for converting an aromatic compound such as benzene into its hydroxylated derivative, generation of carbon monoxide during catalyst regeneration is reduced if the catalyst is a zeolite that contains ruthenium, rhodium, platinum, palladium, or irridium.Type: GrantFiled: August 7, 1996Date of Patent: February 23, 1999Assignee: Solutia Inc.Inventors: Jerry R. Ebner, Timothy R. Felthouse, Denton C. Fentress
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Patent number: 5874647Abstract: A zeolite catalyst for hydroxylating benzene to phenol is treated hydrothermally with a gas comprising approximately 1-100 mole percent water at a temperature between approximately 350.degree.-950.degree. C., and subsequently is treated with an acid. This treatment selectively removes aluminum species from the zeolite catalyst in a manner that increases catalyst stability in phenol production without reducing the activity of the catalyst.Type: GrantFiled: August 20, 1996Date of Patent: February 23, 1999Assignee: Solutia Inc.Inventors: William D. McGhee, Patrick P. B. Notte
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Patent number: 5808167Abstract: A zeolite catalyst, which can be used in a process for hydroxylating benzene to phenol, is treated with an aqueous solution containing ferric or ferrous ions, and is treated with an aqueous solution containing dithionate ions. The treated catalyst exhibits improved selectivity and stability in the benzene hydroxylation process.Type: GrantFiled: August 20, 1996Date of Patent: September 15, 1998Assignee: Solutia Inc.Inventor: William D. McGhee
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Patent number: 5756861Abstract: A method for partial oxidation of aromatic compounds such as benzene, phenol, chlorobenzene, fluorobenzene, toluene, ethylbenzene and the like, with a molar deficiency of nitrous oxide over a catalyst such as a ZSM-5 or ZSM-11 zeolite. The method is advantageous for producing phenol from benzene at high production rates, high nitrous oxide conversion and high selectivity toward the production of phenol.Type: GrantFiled: January 7, 1997Date of Patent: May 26, 1998Assignee: Monsanto CompanyInventors: Gennady Ivanovich Panov, Alexandr Sergeevich Kharitonov, Galina Antolievan Sheveleva
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Patent number: 5672777Abstract: Zeolite catalysts useful for the production of phenol and its derivatives by oxidative hydroxylation of benzene and its derivatives by nitrous oxide, e.g. at temperatures of 225.degree.-450.degree. C., having substantially enhanced process characteristics resulting from hydrothermal treatment using a gas containing from about 3 to 100 mole percent water vapor, e.g. in nitrogen, at a temperature ranging from about 500.degree. to 1000.degree. C. Two hours of hydrothermal treatment has been shown to be effective.Type: GrantFiled: February 28, 1996Date of Patent: September 30, 1997Assignee: Monsanto CompanyInventors: Alexander Sergeevich Kharitonov, Gennady Ivanovich Panov, Galina Anatolievna Sheveleva, Larisa Vladimirovna Pirutko, Tatyana Pavlovna Voskresenskaya, Vladimir Ivanovich Sobolev
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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: 5430181Abstract: Process for improving a controlled oxidation reaction between at least one reactant and oxygen, in which at least one reactant is reacted with oxygen or an oxygen containing gas, constituting a reaction mixture, in the presence of at least one additional gas which is introduced into said reaction mixture and is selected from methane, ethane and helium, and the resulting reaction product from the oxidation reaction is possibly treated so as to give a final product.Type: GrantFiled: February 19, 1993Date of Patent: July 4, 1995Assignee: L'Air Liquide Societe Anonyme Pour L'Etude et L'Exploitation des Procedes Georges ClaudeInventors: Philippe Arpentinier, Jacques Koenig, Yves Torre
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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: 5364978Abstract: The invention relates to a process for the preparation of a phenol by oxidative decarboxylation of benzoic acid in the presence of a copper-containing catalyst, wherein accumulation of tar components in the reactor is avoided by continuously removing a portion of the reaction mixture from the reactor and subjecting the removed portion to an extraction by contacting the removed portion with water and an auxiliary liquid, which auxiliary liquid is not miscible with water, wherein after extraction an aqueous liquid is obtained with benzoic acid and copper salts and an inorganic solution with tar components, wherein the aqueous solution is recycled to the reactor, the extraction being performed with 0.2 to 14 volume parts of auxiliary liquid per volume part of removed reaction mixture and with 0.Type: GrantFiled: August 20, 1993Date of Patent: November 15, 1994Assignee: D.S.M. N.V.Inventors: Johannes A. Kroon, Wim Buijs
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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: 5268512Abstract: A catalyst for producing phenol consisting essentially of a nickel compound supported on a metal oxide carrier, or a catalyst for producing phenol consisting essentially of iron oxide and nickel oxide, and processes for producing phenol using either of the above catalyst. The catalysts of the invention exercise a high conversion of benzoic acid and a high selectivity to phenol, and phenol can be produced in a high yield, particularly in a high space time yield through the processes of the invention using the above catalysts. The above conversion, selectivity and space time yield can be improved by calcining the catalyst at 600.degree. to 900.degree. C.Type: GrantFiled: July 10, 1992Date of Patent: December 7, 1993Assignee: NKK CorporationInventors: Jun Miki, Toshifumi Suzuki, Tsutomu Shikada, Kazuhiko Tate, Yakudo Tachibana
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Patent number: 5210331Abstract: The invention relates to a process for the preparation of a phenol by oxidative decarboxylation of a corresponding arylcarboxylic acid in the presence of a Cu-containing catalyst, the phenol being obtained through a hydrolysis step. The characteristic part of the process is oxidation of a Cu(I)-containing catalyst and reduction and hydrolysis in the absence of oxygen. The process can be carried out under liquid phase or gas phase conditions in a one-step or multi-step process and nucleation agents can be added for crystallization during catalyst oxidation. In a preferred embodiment, at least 0.04 wt.% copper remains present as Cu(I) after oxidation.Type: GrantFiled: December 31, 1991Date of Patent: May 11, 1993Assignee: DSM NVInventors: Wim Buijs, Leon H. B. Frijns, Matthias R. J. Offermanns
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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: 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: 4618730Abstract: The known 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 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: GrantFiled: March 8, 1984Date of Patent: October 21, 1986Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Axel Kleemann
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Patent number: 4588845Abstract: A process is provided for oxidizing unsaturated organic compounds with hydrogen peroxide in the presence of a strong-acid type of polymer containing a cation of a transition metal. The process results in a decrease in undesired side reactions in epoxidations and improved isomer control in the hydroxylation of aromatic compounds.Type: GrantFiled: May 25, 1984Date of Patent: May 13, 1986Assignee: FMC CorporationInventor: Randy A. Bull
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Patent number: 4338471Abstract: Benzene is catalytically oxidized in the vapor phase with oxygen in the presence of an alcohol to be converted to phenol. The catalyst used is represented by the formula: M.sub.a Ag.sub.b P.sub.c O.sub.d wherein M is selected from zinc, titanium, zirconium, tin, bismuth and vanadium, Ag is silver, P is phosphorus and O is oxygen, and a=1, b=0.005.about.5 and c=0 to 6. Phenol is obtained at an enhanced yield even though the catalytic oxidation is carried out at a relatively low temperature as compared with conventional catalytic oxidation processes.Type: GrantFiled: December 17, 1980Date of Patent: July 6, 1982Assignee: Ube Industries, Inc.Inventors: Sumio Umemura, Ryozo Kitoh, Taizo Uda
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Patent number: 4335263Abstract: A process for preparing an aromatic aldehyde represented by the following general formula: ##STR1## wherein R.sub.1 and R.sub.2 each represents a hydrogen atom or a lower alkyl group or R.sub.1 and R.sub.2 may jointly form an alkylene group, provided that R.sub.1 and R.sub.2 do not represent a hydrogen atom at the same time.Type: GrantFiled: December 19, 1980Date of Patent: June 15, 1982Assignee: Sumitomo Chemical Company, LimitedInventor: Masayoshi Minai
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Patent number: 4301307Abstract: 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: GrantFiled: December 20, 1979Date of Patent: November 17, 1981Assignee: Rhone-Poulenc IndustriesInventor: Michel Jouffret
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Patent number: 4212825Abstract: Aldehydes or ketones of not less than 4 or 5 carbon atoms, respectively, are manufactured in a one stage process in the liquid phase by subjecting aldehydes and/or ketones of not less than 2 or 3 carbon atoms, respectively, to an aldol condensation and hydrogenating the resulting olefinically unsaturated aldehyde, the catalyst used for the aldol condensation and hydrogenation containing a mixture of nickel and cobalt, zinc oxide and at least one of the elements iron, arsenic, antimony, bismuth, gallium, indium, thallium, germanium, tin, lead, cadmium and mercury or compounds of the said elements.Type: GrantFiled: November 16, 1977Date of Patent: July 15, 1980Assignee: BASF AktiengesellschaftInventors: Axel Nissen, Gerd Heilen, Ekkehard Sapper, Werner Fliege, Arnold Wittwer
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Patent number: 4208536Abstract: Aromatic compounds of the general formula ##STR1## in which R and R.sub.o represents a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms are hydroxylated by reaction with hydrogen peroxide in the presence of a catalytic amount of a strong acid and the reaction is carried out in the presence of an activator which is a juxtanuclear aromatic aldehyde or derivative thereof selected from an acetal or a benzhydrol.Type: GrantFiled: December 21, 1976Date of Patent: June 17, 1980Assignee: Rhone-Poulenc IndustriesInventors: Michel Costantini, Adrien Dromard, Michel Jouffret, Roland Nantermet
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Patent number: 4154967Abstract: A process for producing phenols which comprises oxidizing an aromatic hydrocarbon ring-substituted by an isopropyl group in one step in the liquid phase using molecular oxygen or a gas containing molecular oxygen in the presence or absence of a solvent, wherein the oxidation is carried out in the presence of an aromatic mercaptan having an acid dissociation constant (pKa) of less than 7.8.Type: GrantFiled: May 6, 1977Date of Patent: May 15, 1979Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Fujihisa Matsunaga, Hirohiko Nambu
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Patent number: 4094912Abstract: Aromatic aldehydes wherein the aldehyde group is directly attached to the aromatic ring are oxidized directly to phenolic compounds in the vapor phase. Tar and carbonaceous product formation are minimized by the method of preheating and mixing the reactants and by a rapid reaction temperature quench of the reaction mixture to below 0.degree. C. Mixing temperature is 300.degree.-350.degree. C. and reaction temperature is 400.degree.-600.degree. C. at 1-10 atmosphere pressure.Type: GrantFiled: November 2, 1976Date of Patent: June 13, 1978Assignee: Standard Oil Company (Indiana)Inventors: Allen I. Feinstein, Shantaram G. Kane, Ellis K. Fields
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Patent number: RE36856Abstract: Zeolite catalysts useful for the production of phenol and its derivatives by oxidative hydroxylation of benzene and its derivatives by nitrous oxide, e.g. at temperatures of 225.degree.-450.degree. C., having substantially enhanced process characteristics resulting from hydrothermal treatment using a gas containing from about 3 to 100 mole percent water vapor, e.g. in nitrogen, at a temperature ranging from about 500.degree. to 1000.degree. C. Two hours of hydrothermal treatment has been shown to be effective.Type: GrantFiled: May 6, 1998Date of Patent: September 5, 2000Inventors: Alexander Sergeevich Kharitonov, Gennady Ivanovich Panov, Galina Anatolievna Sheveleva, Larisa Vladimirovna Pirutko, Tatyana Pavlovna Voskresenskaya, Vladimir Ivanovich Sobolev