Mitsubishi Gas Chemical Company, Inc.

Hiroshi Kurata

Minoru Kakuda

Takashi Onozawa

Takanobu Okamoto

Kikuo Furukawa

Shoichiro Kajiwara

Ryozo Kawai

Yukari Shimizu

Adamantanediols are produced by the hydroxylation of adamantane compounds in a water/organic solvent two-phase system in the presence of a ruthenium compound and a hypochlorite. Throughout the hydroxylation, the hypochlorite concentration in the water phase is regulated within a narrow limited range, for example, by monitoring the pH of the reaction system. With such a control of the hypochlorite concentration, the adamantanediols are produced in a high selectivity and a high yield.

Production of adamantanediols

A process for efficiently separating and recovering a ruthenium compound used as the catalyst in the production of adamantanols. The adamantanols are produced by hydroxylating an adamantane compound in the presence of a ruthenium compound and a salt of hypochlorous acid in a water/organic solvent two-phase system. The hydroxylation product liquid is added with an oxidizing agent to allow the ruthenium compound to be extracted into the organic phase. The ruthenium compound is separated and recovered from the organic phase. Alternatively, the ruthenium compound is back-extracted into the aqueous phase by adding an aqueous alkali solution to the organic phase. Then, the ruthenium compound is separated and recovered from the aqueous phase.

Process for producing adamantanols

Adamantanols are produced in high selectivity and high yields by hydroxylation of adamantane compounds in a specific two-phase solvent system of water and an organic solvent in the presence of a ruthenium compound and hypochlorous acid or its salt. Adamantanediols transfer into the organic phase by adding a specific alcohol to a reaction liquid containing the adamantanols, thereby facilitating extraction of the adamantanediols. The ruthenium compound transfers into the water phase by treating the reaction liquid with alkali prior to the addition of the alcohol and precipitates therein, thereby facilitating the recovery of the ruthenium compound.

Process of producing adamantanols

A water-soluble polymer prepared by melting and reacting a mixture of an oxycarboxylic acid having a melting point of 170.degree. C. or less and maleamic acid, or a mixture of a plurality of oxycarboxylic acids including at least one oxycarboxylic acid having a melting point of 170.degree. C. or less and maleamic acid, at a temperature of 170.degree. C. or less at the start of the reaction to obtain a polymer; and then hydrolyzing the polymer.

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Ibaraki-ken, Japan

Hiroshi Kurata