Ammonia → Benzonitrile, 3-(aminomethyl)-

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A commercially available activated carbon-supported palladium catalyst “PDC-3000” available from Toyo C.C.I. Co., Ltd. (supported palladium: 3% by weight) was activated by reduction with hydrogen. A 100-ml autoclave was successively charged with 3.0 g of the activated catalyst, 12.8 g of isophthalonitrile containing as impurities 0.12% by weight of 3-cyanobenzamide and 0.12% by weight of 3-cyanobenzoic acid, 37 g of liquid ammonia, and 0.1 g of sodium hydroxide. Then, hydrogen was introduced into the autoclave to increase the inner pressure to 20 MPa (gauge). The concentration in the reaction solution was 0.043% by weight for the benzamide compound and 0.043% by weight for the benzoic acid compound. The autoclave was shaken at 50° C. for 30 min. The gas chromatographic analysis on the reaction product solution showed that the conversion of isophthalonitrile was 99.0 mol %, the yields of 3-cyanobenzylamine was 76.0 mol %, and the yield of m-xylylenediamine was 8.4 mol %. The by-products were substantially high-boiling substances.

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