Sumitomo Chemical Company, Limited

Akira Murakami

Tooru Tokumaru

Motoo Hazama

Kiyoshi Ikimi

Kazushige Okamoto

Yoichi Ikeda

Akira Takeshita

Shinzaburo Masaki

Takeo Fujii

Yoshinori Nakayama

Kan Takamine

Michio Yamato

There is disclosed a process for the production of cresols, including the steps of: (a) conducting oxygenation of cymene with oxygen gas or an oxygen-containing gas, thereby obtaining a solution of oxygenation products containing tertiary and primary hydroperoxides of cymene; (b) reacting the solution of oxygenation products obtained in the step (a) with an organic quaternary ammonium salt and an alkali, or with an organic quaternary ammonium hydroxide, thereby decreasing the content of primary hydroperoxide; (c) subjecting the reaction mixture in the step (b) to decomposition in the presence of a catalyst; and (d) subjecting the decomposition mixture in the step (c) to hydrogenation, thereby obtaining the desired cresols.

Process for production of cresols

There is disclosed a process for producing an aromatic amide compound of the general formula (4), including the steps of subjecting an o-nitrophenol compound of the general formula (1) to catalytic reduction in acetone or an aromatic hydrocarbon solvent under the presence of a nickel catalyst to give an o-aminophenol compound of the general formula (2); and (b) subjecting the o-aminophenol compound of the general formula (2) to condensation with an acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) in acetone or an aromatic hydrocarbon solvent under an atmosphere of an inert gas having an oxygen concentration of 1% or less. The acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) may be obtained by allowing a carboxylic acid compound of the general formula (5) to react with thionyl chloride and by concentrating the reaction mixture. Also disclosed is another process for producing an aromatic amide compound of the general formula (4), including the step of subjecting an o-aminophenol hydrochloride salt of the general formula (6) to condensation with an acid chloride compound having a sulfur content of 0.8% or less, based on the weight of the acid chloride compound, of the general formula (3) in an inert solvent.

Process for producing aromatic amide compounds

There is disclosed a process for the production of cresols, including the steps of: (a) conducting oxygenation of cymene with oxygen gas or an oxygen-containing gas without any addition of an alkali, thereby obtaining a solution of oxygenation products containing tertiary and primary hydroperoxides of cymene; (b) washing the solution of oxygenation products obtained in step (a) with an aqueous alkali solution at a temperature in the range of from 10.degree. to 95.degree. C.; (c) subjecting the solution of oxygenation products obtained in step (b) to hydrogenation at a temperature in the range of from 60.degree. to 100.degree. C. to decrease the content of primary hydroperoxide in such a manner that the weight ratio of primary hydroperoxide to tertiary hydroperoxide is not greater than 1/25 (w/w); (d) subjecting the solution treated in step (c) to decomposition in the presence of a catalyst; and (e) subjecting the solution treated in step (d) to hydrogenation to obtain cresols.

Process for producing hydroxy-containing alkylated aromatic compounds by the liquid phase reaction of an aromatic compound having at least one hydroxyl group with an alkylating agent in the presence of a heteropoly acid and water.

Method for producing hydroxy-containing alkylated aromatic compounds

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Oita, Japan

Akira Murakami