Ube Industries, Inc.

Nobuhiro Ii

Junichi Kugimoto

Hideo Shimomura

Ryouta Yasumatsu

Takashi Doi

Satoru Fujitsu

Nobuyuki Kuroda

Yasuhisa Fukuda

Joji Kawai

Takato Nakamura

Joji Funatsu

Tadashi Gotou

The present invention relates to a process for producing laurolactam from cyclododecanone oxime by liquid-phase rearrangement reaction using trichlorotriazine as a rearrangement catalyst. The present invention can provide a process which can solve the problem of termination of the reaction at a certain conversion, can prevent an inactive precipitate generated from trichlorotriazine from precipitating in the course of the reaction process, and can remove an inactive precipitate, an active intermediate and a residual catalyst.

Process for producing laurolactam

Provided is a process for efficiently producing laurolactam by simple steps from cyclododecanone and hydroxylamine. This production process comprises the steps of: (a) reacting cyclododecanone with hydroxylamine in an aqueous solution in the presence of an oxime-formation solvent to produce cyclododecanone oxime; (b) separating the reaction mixture obtained after the oxime-forming step into an oil and an aqueous phases and collecting a solution of cyclododecanone oxime of the oil phase; (c) removing a part or all of the oxime-formation solvent and dissolved water from the solution of cyclododecanone oxime which is collected as an oil phase in the oil/aqueous phase separation step, whereby preparing a solution containing a rearrangement solvent to be used in a rearrangement reaction in a later step and the cyclododecanone oxime; (d) producing laurolactam from cyclododecanone oxime by rearrangement reaction using an aromatic-ring containing compound as a rearrangement catalyst; and (e) separating and removing the rearrangement solvent and the rearrangement catalyst from the reaction mixture after the rearrangement step, and purifying the laurolactam.

An epoxycyclododecane compound is produced by a catalytic hydrogenation reaction of 1,2-epoxy-5,9-cyclododecadiene, using a specific platinum-containing catalyst having a long life, under a hydrogen gas pressure of 0.8 to 9 MPa, and with a high yield of the target compound.

Method of producing an epoxycyclododecane compound

Growing community of inventors

Ube, Japan

Nobuhiro Ii