Mitsubishi Gas Chemical Company, Inc.

Takasago International Corporation

Tetsuo Tomita

Norio Takeda

Tomiya Isshiki

Mitsuo Abe

Akira Ito

Osamu Aoki

Mitsuo Miura

Yoshiyuki Aoki

Tadashi Yoshii

Hidenori Kumobayashi

Akitoshi Sugio

Noboru Sayo

Takao Saito

Yasushi Kato

Takao Kondo

Kazuhiko Matsumura

Hidemasa Takaya

Eiichi Yonemitsu

Toshiaki Takata

Kyoko Tamao

Shuzabu Sakaguchi

Kaoru Tsuyuki

Masahiro Jono

Toshiaki Kohzaki

Toshiaki Kozaki

Satoshi Mano

Nozomu Sakai

A phosphine compound represented by one of the formulas: ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a halogen atom or a lower alkyl group or taken together form a divalent hydrocarbon group; and R.sup.3 and R.sup.4, which may be the same or different, each represent a lower alkyl group, a phenyl group or a phenyl group substituted with a halogen atom, a lower alkyl group or a lower alkoxy group or taken together form a divalent hydrocarbon group, and wherein R.sup.6 and R.sup.6' which may be the same or different, each represent a hydrogen atom, a lower alkyl group or a lower alkoxy group; R.sup.5, R.sup.5', R.sup.11 and R.sup.11' which may be the same or different, each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; or a pair of R.sup.5 and R.sup.6 or a pair of R.sup.5' and R.sup.6' may form a ring; R.sup.7 and R.sup.8, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a lower alkyl group, a halogen atom or a lower alkoxy group; and R.sup.9 and R.sup.10, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a lower alkyl group, a lower alkoxy group or a halogen atom; or R.sup.9 and R.sup.10 may be taken together to form a divalent hydrocarbon group.

Phosphine compound, complex containing the phosphine compound as ligand,

A process for the preparation of 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-diene-1-one from 2,4,6-trimethylphenol is disclosed, comprising reacting 2,4,6-trimethylphenol with an aqueous solution or suspension of hypohalogenous acid or salt thereof in an aqueous medium or mixed medium of water and specific organic solvents. This process enables to prepare 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-diene-1-one, which is a precursor for 2,3,5-trimethylhydroquinone, a starting material for the preparation of vitamin E, by a simplified operation, safely and at high yields.

Process for producing 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-diene-1-one

A process for producing a benzophenone-azine which comprises reacting the corresponding benzophenone-imine with molecular oxygen or benzophenone with ammonia and molecular oxygen in the presence of a catalyst selected from the group consisting of metals, metal oxides and alloys of two or more metals, particularly copper or copper alloy-containing catalyst, is disclosed.

Process for producing benzophenone-azines

Hydrazine sulfate having a relatively large particle diameter and a high purity is produced by hydrolysis of benzophenoneazines by sulfuric acid having a concentration of 75% by weight or less in an amount of 1.1 times by mole or more the stoichiometric amount in a very high conversion and a high yield with less operational loss.

Process for producing hydrazine sulfate

An imine compound is produced by reacting a benzophenone with ammonia in the presence of 0.01 to 10% by weight of a carboxylic acid as a catalyst at a reaction temperature of 50.degree. to 350.degree. C on the basis of benzophenone. Ammonia is fed to the reaction system continuously under a pressure of 2 to 15 atmospheres. A solvent may be used for the reaction. The catalyst carboxylic acid can be readily recovered and reused without any influence of water formed by the reaction and brings about no problem of corrosion to reactor apparatus.

Process for producing imine compounds

An imine compound is produced in high yield by reacting a benzophenone with ammonia in the presence of 0.01 to 100% by weight of an oxide of at least one of metals selected from the group consisting of metals of the second to fifth periods of Group III to V of the periodic Table, and iron as a catalyst at a reaction temperature of 150.degree. to 250.degree. C on the basis of benzophenone. Ammonia is fed to the reaction system continuously under a pressure of 2 to 15 atmospheres. A solvent may be used for the reaction. The catalyst metal oxide can be readily recovered and reused without any influence of water formed by the reaction.

Polyphenylene oxides, self-condensation products of phenols, are prepared with a high yield through oxidative coupling by employing a catalyst system with higher activity, which comprises a copper compound, iodine or an iodine-containing compound and a primary amine.

Process for preparing polyphenylene oxides

Polyphenylene oxides, self-condensation products of phenols, are produced through oxidative coupling by employing a novel catalyst system which comprises a copper compound, an iodine compound and tertiary diamine which is capable of forming a stable chelate ring with the copper compound. According to this invention, copper compounds, which hitherto have been considered to be unsuitable for using with tertiary amines, act with excellent performance as a component of the catalyst.

Process for producing polyphenylene oxides

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Tokyo, Japan

Tetsuo Tomita