Preparing From Peroxide Or Preparing By Oxidation Patents (Class 568/741)
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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: 4929771Abstract: Process for the preparation of alkyl-substituted phenols or naphthols by oxidizing the corresponding dialkylbenzenes or dialkylnaphthalenes, respectively, at elevated temperatures of, for example, 70.degree. to 130.degree. C. by means of oxygen or oxygen donors, in the absence of solvents and in the presence of an alkali metal salt or alkaline earth metal salt of an organic carboxylic acid having 5 to 14 carbon atoms, to give the corresponding 2,6-dialkylnaphthalene-or 1,4-dialkylphenyl monohydroperoxides and subsequently hydrolysing the latter in a customary manner.The process results in pure, easily isolatable products in a good yield. The products of the process according to the invention are valuable precursors and intermediates for, inter alia, dyes, plastics or pharmaceuticals.Type: GrantFiled: December 1, 1988Date of Patent: May 29, 1990Assignee: Ciba-Geigy CorporationInventors: Martin Clausen, Paul Rys, Wang Junkuan
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Patent number: 4906790Abstract: A method of oxidizing secondary alkyl substituted naphthalenes with molecular oxygen in a liquid phase to hydroperoxides, carbinols or mixtures of these, which comprises: oxidizing the secondary alkyl substituted naphthalenes in the presence of an aromatic hydrocarbon having a fused ring which contains at least one methylene group therein in amounts of not more than about 1000 ppm based on the secondary alkyl substituted napththalene used.A process of producing isopropylnaphthols is also disclosed, which comprises: oxidizing diisopropylnaphthalenes with molecular oxygen in a liquid phase to diisopropylnaphthalene monohydroperoxides in the presence of (a) either an aromatic hydrocarbon having a fused ring which contains at least one methylene group therein, or a paladium catalyst soluble in the reaction mixture, and (b) an organic polar compound such as acetonitrile; and then acid-decomposing the diisopropylnaphthalene monohydroperoxide to the isopropylnaphthol.Type: GrantFiled: September 9, 1988Date of Patent: March 6, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Masaharu Ishiguro, Hisaya Miki, Nobuya Hirokane
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Patent number: 4898995Abstract: A method is disclosed for the synthesis of phenol and acetone by decomposition over a heterogeneous catalyst from the group consisting of a heteropoly acid on an inert support or an ion exchange resin with a sulfonic acid functionality. The method allows for quantitative conversions with yields of up to >99 mole % or better.Type: GrantFiled: October 24, 1988Date of Patent: February 6, 1990Assignee: Texaco Chemical CompanyInventors: John F. Knifton, John R. Sanderson
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Patent number: 4876397Abstract: A method is disclosed for the synthesis of phenol and acetone by decomposition over a heterogeneous catalyst comprising a fluorine-containing acidic compound on an inert support. The method allows for quantitative conversions with yields of up to >99 mole %.Type: GrantFiled: October 24, 1988Date of Patent: October 24, 1989Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Neal J. Grice
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Patent number: 4870217Abstract: A method is disclosed for the synthesis of phenol and acetone by acid-catalyzed decomposition over a catalyst comprising an acidic smectite clay, particularly an acidic montmorillonite silica-alumina clay. The method allows for quantitative conversions with yields of up to 98% mole or better. Further the method is capable of operating efficiently at high LHSVs.Type: GrantFiled: October 24, 1988Date of Patent: September 26, 1989Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 4861920Abstract: Process for the preparation of 2,6-dihydroxynaphthalene from 2,6-dialkylnaphthalenes, which are dissolved in an inert solvent and are oxidized at temperatures from 50.degree. to 150.degree. C. by means of oxygen or oxygen donors, in the presence of an alkali metal salt or alkaline earth metal salt of an organic carboxylic acid having 5 to 14 carbon atoms, to give the corresponding 2,6-dialkylnaphthalene dihydroperoxides, and the latter are subsequently hydrolysed.The process results in pure, easily isolatable products in a good yield. The process products according to the invention are valuable intermediates for, inter alia, dyes, plastics, synthetic fibres, polymeric liquid crystals or pharmaceuticals.Type: GrantFiled: March 14, 1988Date of Patent: August 29, 1989Assignee: Ciba-Geigy CorporationInventors: Martin Clausen, Paul Rys
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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: 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: 4783557Abstract: Disclosed in accordance with the present invention are processes for the preparation of hydroperoxides and/or carbinols by liquid phase oxidation of secondary alkyl-substituted naphthalenes with molecular oxygen, wherein the oxidation reaction is carried out by dissolving in the reaction mixture containing the secondary alkyl-substituted naphthalenes at least 0.5 ppm in terms of metal, based on the starting secondary alkyl-substituted naphthalenes, of at least one compound of metal selected from the group consisting of palladium and gold, said metal compound being soluble in the reaction mixture of the secondary alkyl-substituted naphthalenes.Type: GrantFiled: September 10, 1987Date of Patent: November 8, 1988Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Yutaka Haneda, Sadao Yoshimoto, Hisaya Miki, Masaaki Yasuda, Shintarou Araki, Masatoshi Nitabaru
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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: 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: 4551562Abstract: 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 13, 1984Date of Patent: November 5, 1985Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Axel Kleemann
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Patent number: 4533766Abstract: The known nuclear hydroxylation of substituted phenols or phenol ethers with organic solutions of hydrogen peroxide in the presence of a catalyst is carried out in improved manner by employing both (1) a special, practically water free solution of hydrogen peroxide in an organic solvent which forms an azeotrope with water, which azeotrope boils below the boiling point of hydrogen peroxide, and (2) sulfur dioxide as a catalyst. Through this, the nuclear hydroxylation is substantially simpler than previously; difficult separations, e.g., from water-phenol, or the separation and recovery of the catalyst are eliminated. Besides, the yields are increased.Type: GrantFiled: March 8, 1984Date of Patent: August 6, 1985Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Axel Kleemann
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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: 4490565Abstract: Phenol and acetone are produced by the cleavage of cumene hydroperoxide in the presence of a solid heterogeneous catalyst with acidic activity comprising zeolite beta.Type: GrantFiled: May 6, 1983Date of Patent: December 25, 1984Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Bruce P. Pelrine
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Patent number: 4490566Abstract: Phenol and acetone are produced by the cleavage of cumene hydroperoxide in the presence of a solid heterogeneous catalyst with acidic activity comprising an intermediate pore size zeolite such as ZSM-5.Type: GrantFiled: May 6, 1983Date of Patent: December 25, 1984Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Bruce P. Pelrine
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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: 4463198Abstract: An improved method for the acid-catalyzed rearrangement of a dialkylbenzene dihydroperoxide to a dihydric phenol which eliminates the formation of an emulsion during the subsequent separation and recovery of the dihydric phenol in a process which utilizes water, the method comprising the addition of the acid as a solution in a water soluble organic solvent, preferably a ketone, which is non-reactive with the acid.Type: GrantFiled: August 23, 1982Date of Patent: July 31, 1984Assignee: The Goodyear Tire & Rubber CompanyInventors: Edward N. Nowak, William S. Hollingshead, Joel Muse, Jr.
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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: 4339614Abstract: Resorcinol is prepared by an improved process through superacid (such as perfluorinated alkanesulfonic acids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as Nafion-H catalyzed cleavage-rearrangement reaction of meta-isopropylphenol hydroperoxide in the form of its protected ether or ester derivatives, including readily cleavable and reusable trimethylsilyl and trifluoromethanesulfonyl derivates. Part of the process is the preparation of needed meta-isopropylphenol in high purity free of other isomers by treating any mixture of isopropylphenol isomers in an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic acid of one to six carbon atoms and a Lewis acid fluoride or by alkylating (transalkylating) phenol with a propyl alkylating agent in the presence of the aforementioned superacid systems.Type: GrantFiled: March 14, 1980Date of Patent: July 13, 1982Assignee: PCUK Produits Chimiques Ugine KuhlmannInventor: George A. Olah
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Patent number: 4339613Abstract: Resorcinol is prepared in high yield and purity by an improved process through superacid (such as perfluorinated alkanesulfonic acids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as acidified Nafion-H, catalyzed cleavage-rearrangement reaction of meta-bis(2-hydroperoxy-2-propyl)-benzene (meta-diisopropylbenzene dihydroperoxide). Part of the process is the preparation of needed meta-diisopropylbenzene in high purity (98-100%) substantially free of other isomers by treating any mixture of diisopropylbenzenes with an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic acid of one to six carbon atoms and a Lewis acid fluoride, or by alkylating (transalkylating) cumene with a propyl alkylating agent in the aforementioned superacid systems.Type: GrantFiled: March 14, 1980Date of Patent: July 13, 1982Assignee: PCUK Produits Chimiques Ugine KuhlmannInventor: George A. Olah
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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: 4324925Abstract: An improved process for the preparation of a polyhydric phenol by hydroxylation of a phenol with a peroxidic hydroxylating agent, is disclosed. The improvement resides in that before the hydroxylation, all or some of the mixture to be hydroxylated is treated with a cation exchanger.Type: GrantFiled: June 30, 1980Date of Patent: April 13, 1982Assignee: Bayer AktiengesellschaftInventors: Christoph Jupe, Helmut Waldmann, Hermann Seifert
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Patent number: 4271322Abstract: Disclosed is a process for the preparation of phenols which comprises the steps of (I) decomposing a hydroperoxide of an isopropyl aromatic compound with an acid catalyst, (II) separating the decomposition product obtained in step (I) into acetone, phenols, hydrocarbons and distillation residue by distillation of the decomposition product and (III) thermally decomposing the distillation residue and recycling the resulting crude phenol to step (II), wherein the crude phenol obtained in step (III) is contacted with a glycol to form a hydrocarbon layer and an extract layer comprising the glycol and phenol, and the phenol in said extract layer is recycled to step (II).According to this process, mingling of impurity components having a boiling point close to that of the desired phenol, which are contained in the thermal decomposition product of the distillation residue, into the product phenol can be effectively prevented, and the desired phenol can be obtained at a high purity and at a high recovery yield.Type: GrantFiled: January 3, 1980Date of Patent: June 2, 1981Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Fujihisa Matsunaga, Hirohiko Nambu
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Patent number: 4246203Abstract: The invention relates to a process in which an aromatic hydroperoxide of formula: ##STR1## wherein independently R.sub.1 is methyl or ethyl, R.sub.2 is hydrogen, methyl or ethyl, or where R.sub.1 and R.sub.2 together form an alicyclic ring of 5 or 6 carbon atoms, R.sub.3 is hydrogen or alkyl and R.sub.4 and R.sub.5 are hydrogen, alkyl or together form an automatic ring, n is 0, 1 or 2 and n.sup.1 is 1 or 2, is converted to a phenol and a carbonyl compound in a catalyzed cleavage decomposition reaction. In particular cumene hydroperoxide is converted to phenol and acetone. Instead of removing the decomposition products from the reactor in the liquid phase and dissipating the reaction heat as in prior art processes the heat is used to remove the phenol and the carbonyl compound in the vapor phase leaving a liquid residue of higher-boiling compounds and catalyst in the case where a liquid cleavage catalyst is employed.Type: GrantFiled: August 9, 1979Date of Patent: January 20, 1981Assignee: BP Chemicals LimitedInventor: Max M. Wirth
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Patent number: 4182918Abstract: A process has been invented for the preparation of dihydric substituted phenols which comprises reacting a solution, which is essentially anhydrous and free from hydrogen peroxide, of a percarboxylic acid in an inert organic solvent with a monohydric substituted phenol, which is derived from benzene, naphthalene or anthracene and still contains at least one free hydrogen atom in the aromatic nucleus, at temperatures from about -20.degree. C. to about 120.degree. C.The dihydric substituted phenols obtained according to the invention are known, important industrial intermediate products used in the fields of photography, dyestuffs and plastics, as well as in the scent and flavoring areas.Type: GrantFiled: December 5, 1977Date of Patent: January 8, 1980Assignee: Bayer AktiengesellschaftInventors: Hermann Seifert, Helmut Waldmann, Wulf Schwerdtel, Wolfgang Swodenk
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Patent number: 4147726Abstract: An organic hydroperoxide is hydrolyzed by acid-catalysis in a reaction medium comprising essentially a mixture of a polar solvent, e.g. a low boiling, low molecular weight alcohol and/or sulfolane and phenol. Specifically cyclohexanone and phenol are obtained from cyclohexylbenzene hydroperoxide.Type: GrantFiled: November 8, 1976Date of Patent: April 3, 1979Assignee: Phillips Petroleum CompanyInventor: Yulin Wu
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Patent number: 4120902Abstract: A process for the separation and purification of reaction product from the oxidation of hydrocarbyl aromatic compounds to hydrocarbyl aromatic hydroperoxides is provided comprising (1) extracting the oxidation effluent with an aqueous alcoholic base, (2) contacting the aqueous phase thus produced with a paraffin hydrocarbon solvent to remove residual unoxidized hydrocarbyl aromatic, (3) extracting the aqueous hydrocarbyl aromatic hydroperoxide phase remaining with an aromatic solvent, and (4) washing of the hydroperoxide-containing aromatic phase with water to remove base. The resulting hydroperoxide phase substantially free of unoxidized hydrocarbyl aromatic can be subjected to acid-catalyzed cleavage to produce hydroxy aromatic and carbonyl compound products without encountering the problem of azeotrope formation between unoxidized hydrocarbyl aromatic reactant with cleavage product.Type: GrantFiled: March 7, 1977Date of Patent: October 17, 1978Assignee: Phillips Petroleum CompanyInventor: Yulin Wu
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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