Acetic Anhydride → 3-Tolunitrile

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A glass three-neck flask was charged with 106.3 g of acetic anhydride, 0.67 g of cerous (III) acetate monohydrate, 0.88 g of zinc (II) acetate dehydrate and 0.78 g of ammonium bromide, and the mixture was stirred at 500 rpm using stirring blades, while air was bubled in at 150 ml/min at atmospheric pressure. In succession, the three-neck flask was heated in an oil back, to be kept at 90° C., and 14.9 g of m-cyanotoluene was added at a time from a dropping funnel, to start reaction. After initiation of reaction, 0.1 g of ammonium bromide was added every hour 8 times. The reaction solution was sampled at predetermined time intervals and analyzed by high performance liquid chromatography. The m-cyanotoluene conversion and m-cyanobenzylidene diacetate yield were calculated from the following formulae:

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