Peroxide Or Peracid Utilized Patents (Class 568/803)
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Patent number: 5120884Abstract: Hydroxy arylcyclobutenes are prepared by the Baeyer-Villiger oxidation of arylcyclobutene aldehydes with permonophosphoric acid.Type: GrantFiled: February 14, 1991Date of Patent: June 9, 1992Assignee: The Dow Chemical CompanyInventors: P. J. Thomas, R. Garth Pews
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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: 5012017Abstract: A method for preparing substituted phenoxyphenols which are useful in the preparation of herbicidal (phenoxyphenoxy)propionates is disclosed. The process involves the oxidation of substituted phenoxyphenones to the corresponding phenoxyphenyl esters and their conversion to the desired phenoxyphenol. Novel intermediates for the process are similarly disclosed.Type: GrantFiled: February 21, 1989Date of Patent: April 30, 1991Assignee: DowElancoInventors: Jon A. Orvik, Norman R. Pearson, Anthony P. Haag, Timothy J. Adaway, Larry D. Kershner, Andrew S. Kende
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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: 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: 4918238Abstract: Mixtures of alcohols and ketones are selectively and actively produced by catalytically oxidizing at least one alkane with an organic hydroperoxide, in the presence of a catalytically effective amount of osmium or an osmium compound, notably osmium tetroxide.Type: GrantFiled: March 3, 1989Date of Patent: April 17, 1990Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Jean-Pierre Lecomte
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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: 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: 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: 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: 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: 4590305Abstract: The known nuclear hydroxylation of phenol or 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) selenium dioxide as a catalyst. Through this, the nuclear hydroxylation is substantially simpler than previously. Besides, for the first time, it is possible to control the ortho to para ratio or the two ortho ratios to each other.Type: GrantFiled: March 8, 1984Date of Patent: May 20, 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: 4578521Abstract: This invention provides a process in which phenol is reacted with hydrogen peroxide to form hydroquinone in the presence of a shape-selective zeolite catalyst such as HZSM-5. Essentially no catechol byproduct is produced.Type: GrantFiled: February 4, 1985Date of Patent: March 25, 1986Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Stuart D. Hellring
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Patent number: 4529824Abstract: Peroxidic complexes of vanadium, niobium or tantalum, wherein the metal is linked to an oxygen molecule carrying two negative charges, are used either as reactants for the oxidation of olefinic substrates or hydrocarbons, or as hydrocarbons oxidation catalysts, particularly for converting olefinic compounds to epoxides or aliphatic or aromatic hydrocarbons to the corresponding alcohols or phenols.Type: GrantFiled: June 21, 1983Date of Patent: July 16, 1985Assignee: Institut Francais du PetroleInventors: Hubert Mimoun, Lucien Saussine, Erick Daire, Alain Robine, Jacques G. de Luzinais
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Patent number: 4469899Abstract: A process for producing phloroglucin important as an intermediate compound of medicine, sensitizer and the like which comprises reacting an oxidation product containing at least one carbinol compound of carbinol dihydroperoxide, dicarbinol hydroperoxide and tricarbinol obtained by oxidation of 1,3,5-triisopropylbenzene, with hydrogen peroxide in a heterogeneous system in the presence of an acid catalyst and an organic solvent inert to the hydrogen peroxide and capable of dissolving the oxidation product, and decomposing the reaction product with an acid.Type: GrantFiled: August 11, 1982Date of Patent: September 4, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Makoto Nakamura, Tsutomu Chiyoda, Shinichi Hasegawa
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Patent number: 4465872Abstract: p-Cresol is produced in one step by direct oxidation of p-tolualdehyde with a peroxide in formic acid as a solvent while keeping 3 to 15% by weight of water in formic acid on the basis of formic acid and a reaction temperature in a range of 50.degree. to 150.degree. C.Type: GrantFiled: June 23, 1982Date of Patent: August 14, 1984Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takashi Suzuki, Shoichiro Hashimoto, Masami Orisaku, Rieko Nakano
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Patent number: 4419528Abstract: A process for the selective preparation of .alpha.- or .beta.-naphthol, respectively, by acid (Lewis or Bronsted, or superacidic mixtures thereof) catalyzed hydroxylation of naphthalene with hydrogen peroxide. Conventional (non-superacidic) acid systems, such as hydrogen fluoride, pyridine-hydrogen fluoride complexes (i.e., pyridinium polyhydrogen fluoride), anhydrous aluminum chloride, and the like give .alpha.-naphthol regioselectivity in isomeric purity of 92 to 98+%. The use of superacidic systems, such as fluorosulfuric acid, fluorosulfuric acid-antimony pentafluoride, hydrogen fluoride-boron trifluoride, hydrogen fluoride-antimony pentafluoride, hydrogen fluoride, tantalum pentafluoride, and the like, result, on the other hand, in the formation of .beta.-naphthol in 92-98% isomeric purity.Type: GrantFiled: October 5, 1979Date of Patent: December 6, 1983Assignee: PCUK - Produits Chimiques Ugine KuhlmannInventor: George A. Olah
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Patent number: 4396783Abstract: A process for the hydroxylation of aromatic hydrocarbons by hydrogen peroxide, consisting in reacting said compounds in the presence of synthetic zeolites which contain heteroatoms, both replaced and exchanged.The reaction is carried out at a temperature comprised between 80.degree. C. and 120.degree. C. and in the presence of the hydrocarbon only or in the presence of a solvent which permits, at least partially, to admix the aromatic hydrocarbon with the hydrogen peroxide.Type: GrantFiled: September 4, 1981Date of Patent: August 2, 1983Assignee: Anic S.p.A.Inventors: Antonio Esposito, Marco Taramasso, Carlo Neri
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Patent number: 4387252Abstract: The invention relates to an improved process for the preparation of polyhydric phenols by hydroxylation of phenols with peroxidic hydroxylating agents and in the presence of 0.00005 to 0.03% by weight (relative to the phenols employed) of substances which can form chelate complexes with metal ions, such as nitrogen-containing di- or poly- carboxylic acids or phosphoric acid derivatives. The products of the process are known to be useful in the fields of photography, dyestuffs, plastics, fragrances and flavors.Type: GrantFiled: October 3, 1980Date of Patent: June 7, 1983Assignee: Bayer AktiengesellschaftInventors: Christoph Jupe, Helmut Waldmann, Hermann Seifert
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Patent number: 4351968Abstract: Pyrogallol, and analogues thereof having an alkyl, carboxy or alkoxycarbonyl substituent in the benzene ring, and their salts, are prepared by oxidizing, preferably by hydrogen peroxide, the corresponding compounds in which 1 or 2 of the OH groups are replaced by --COR.sup.5 groups where R.sup.5 represents hydrogen, alkyl or phenylalkyl. The production of intermediates is also described and some of these are novel.Type: GrantFiled: September 12, 1980Date of Patent: September 28, 1982Assignee: FBC LimitedInventor: John F. Harris
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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: 4334108Abstract: Disclosed is a process for the preparation of phenols which comprises reacting an .alpha.-hydroxyalkyl-substituted aromatic compound and/or an .alpha.,.beta.-unsaturated alkyl-substituted aromatic compound with hydrogen peroxide in the presence of an acid catalyst, in which hydrogen peroxide is diluted with a diluent, especially acetone, so that the volume is at least 10 times the original volume, and the diluted hydrogen peroxide is supplied in a divided manner to at least two portions of a reaction vessel or the diluted hydrogen peroxide is scattered by sprinkling into the reaction vessel. According to a preferred embodiment, the diluted hydrogen peroxide is continuously supplied to the gas phase in the reaction vessel from a scattering device which is similar to but separate from a scattering device for supplying the starting aromatic compound, particularly, a product formed by oxidizing an isopropyl aromatic compound with molecular oxygen.Type: GrantFiled: June 30, 1980Date of Patent: June 8, 1982Assignee: Mitsu Petrochemical Industries Ltd.Inventors: Katsuhiko Hashimoto, Hirohiko Nambu, Kazuhiro Watari, Kenichi Mizuno, Tadateru Murakami, Yutaka Matsuoka, Mitsutoshi Moriyama, Norio Ohno
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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: 4214105Abstract: A process for the production of pyrocatechol and hydroquinone by the hydroxylation of phenol in the nucleus with hydrogen peroxide, wherein phenol 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: GrantFiled: September 15, 1978Date of Patent: July 22, 1980Assignee: Bayer AktiengesellschaftInventors: Hermann Seifert, Helmut Waldmann, Wulf Schwerdtel, Wolfgang Swodenk
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Patent number: 4174460Abstract: 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: GrantFiled: March 31, 1977Date of Patent: November 13, 1979Assignee: Bayer AktiengesellschaftInventors: Hermann Seifert, Helmut Waldman, Wulf Schwerdtel, Wolfgang Swodenk
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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