Development of an efficient method for preparation of 1,3,5-trihydroxyisocyanuric acid (THICA) and its use as aerobic oxidation catalyst |
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Authors: | Naruhisa Hirai Yoshinobu Tatsukawa Yasutaka Ishii |
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Affiliation: | a Daicel Chemical Industries, Ltd, Shinzaike, Aboshi-ku, Himeji, Hyogo 671-1283, Japan b Department of Applied Chemistry, Faculty of Engineering, Kansai University, Suita, Osaka 564-8680, Japan |
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Abstract: | 1,3,5-Trihydroxyisocyanuric acid (THICA), which serves as an efficient radical-producing catalyst from hydrocarbons, was successfully prepared by two methods. The reaction of O-benzylhydroxyamine with phenyl chloroformate gave formbenzyloxycarbamic acid phenyl ester of which subsequent treatment with dimethylaminopyridine (DMAP) produced 1,3,5-tribenzyloxyisocyanurate leading to THICA by hydrogenation with H2 on Pd/C. The other method involved the direct synthesis of 1,3,5-tribenzyloxyisocyanurate from O-benzylhydroxyamine and diphenyl carbonate. The aerobic oxidation of p-methylanisole catalyzed using THICA as a key catalyst afforded p-anisic acid in almost quantitative yield (>99%). |
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Keywords: | Oxidation Dioxygen 1,3,5-Trihydroxyisocyanuric acid |
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