Toray Industries, Inc.

Daijiro Tsukamoto

Katsushige Yamada

Kenji Kawamura

Masato Akahira

Masateru Ito

Koji Yamauchi

Satoshi Sakami

Daisuke Yamamoto

Kohei Yamashita

Tetsu Yonehara

The present invention relates to a method of producing ε-caprolactam, the method including the following steps (A) and (B): (A) a step of reacting 5-cyanovaleramide with hydrogen in an aqueous solvent in a presence of a hydrogenation catalyst to obtain a 5-cyanovaleramide hydrogenation reaction mixture; (B) a step of heating the 5-cyanovaleramide hydrogenation reaction mixture at a temperature of 180° C. or higher and 300° C. or lower in an aqueous solvent to obtain ε-caprolactam.

Method for producing ε-caprolactam

A method relates to producing 3-hydroxyadipic acid-3,6-lactone, the method including the following steps (A) and (B): (A) a step of adding an acid to a 3-hydroxyadipic acid-containing aqueous solution to obtain a 3-hydroxyadipic acid-3,6-lactone-containing aqueous solution; and (B) a step of obtaining a 3-hydroxyadipic acid-3,6-lactone extract by bringing the 3-hydroxyadipic acid-3,6-lactone-containing aqueous solution obtained in step (A) into contact with an extraction solvent that is phase-separated from the solution.

Method of producing 3-hydroxyadipic acid-3,6-lactone

A method produces &#x3b5;-caprolactam through adipamide as an intermediate, and characteristically includes a lactamization step of reacting adipamide, formed from a material compound, with hydrogen and ammonia in the presence of a catalyst containing: a metal oxide mainly containing an oxide(s) of one or more metallic elements selected from the group consisting of metallic elements of group 5 and groups 7 to 14 in the 4th to 6th periods of the periodic table; and a metal and/or a metal compound having a hydrogenation ability.

Method for producing &#x3f5;-caprolactam

A method of producing &#x3b5;-caprolactam from 3-oxoadipic acid includes: step 1 of mixing at least one selected from the group consisting of 3-oxoadipic acid and salts thereof with a catalyst and a solvent in the presence of hydrogen to produce 3-hydroxyadipic acid; and step 2 of reacting the 3-hydroxyadipic acid which is a product of step 1, a salt or carboxylic acid derivative thereof, or a mixture of these with hydrogen and ammonia.

Method of producing epsilon-caprolactam

A method for selective production of &#x3b5;-caprolactam, wherein a substance inducible from a biomass resource is used as a material; the reaction process is short; ammonium sulfate is not produced as a by-product; and production of by-products is suppressed; is disclosed. The method for producing &#x3b5;-caprolactam comprises the step of reacting a particular compound inducible from a biomass resource, such as &#x3b1;-hydromuconic acid, 3-hydroxyadipic acid, or 3-hydroxyadipic acid-3,6-lactone, or a salt thereof with hydrogen or ammonia.

Method for producing epsilon-caprolactam

A method for producing highly pure p-toluic acid by a simple solid-liquid separation operation using as a raw material a substance inducible from a biomass resource and suitable for fermentation production by a microorganism is disclosed. The method for producing p-toluic acid includes: a dehydration reaction step of dehydrating Compound(s) (1)-(4), which are substances inducible from biomass resources and suitable for fermentation production by microorganisms; and a solid-liquid separation step of recovering a solid produced by this dehydration reaction by a simple solid-liquid separation operation.

P-toluic acid production method

A method for producing butadiene from 2,3-butanediol with high selectivity without using a radioactive substance is disclosed. The method for producing butadiene comprises the step of dehydrating 2,3-butanediol in the presence of a catalyst containing an alkali metal salt of phosphoric acid such as an alkali metal dihydrogen phosphate supported on silica. Preferred examples of the alkali metal herein include K, Rb, and Cs. The catalyst is preferably a catalyst prepared by calcination of the silica to which the alkali metal of phosphoric acid is attached.

Method for producing butadiene

Disclosed is a method for producing p-xylene and/or p-tolualdehyde with high yield through a short process using biomass resource-derived substances as raw materials. The method for producing p-xylene and/or p-tolualdehyde of the present invention comprises: a cyclization step of producing 4-methyl-3-cyclohexenecarboxaldehyde from isoprene and acrolein; and an aromatization step of producing p-xylene and/or p-tolualdehyde from 4-methyl-3-cyclohexenecarboxaldehyde by gas-phase flow reaction using a catalyst(s).

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Kamakura, Japan

Daijiro Tsukamoto