Phthalic Anhydride → Benzoic acid, 2,2'-(dioxydicarbonyl)bis-

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Reaction Steps

Diphthaloyl peroxide was prepared by adding finely powdered phthalic anhydride (7.2g) gradually over a period of five minutes to a solution of hydrogen peroxide (0.46% by weight, 90 cm3) maintained at a temperature of between 1° to 3° C by the use of a cooling jacket, and the pH of 9 plus or minus 0.2 by dropwise addition of sodium hydroxide sufficient to counteract the generation of acidity as the reaction proceeded. The solution was stirred constantly, so that the proportion of the finely powdered phthalic anhydride which did not go into solution, remained in suspension, and the temperature and pH were controlled for a further 25 minutes, by which time substantially all the hydrogen peroxide had been consumed. The suspension was filtered into sulphuric acid (10% by weight, 30 cm3) and substantially all the diphthaloyl peroxide precipitated out. The solid which had been filtered off was washed with water and then dried to recover phthalic anhydride (3.03g). The acidified filtrate was centrifuged and the precipitate, separated thereby, was washed with water (40 cm3) and dried giving diphthaloyl peroxide (3.l g). An iodometric assay of the crude product showed that it contained 89.1% of active material, and negligible amount of monoperoxyphthalic acid, giving a reaction yield of 59.4%, based on consumption of phthalic anhydride.

Provenance & Evidence