Abstract
Abstract In the course of early experiments on the oxidation of rubber, it was observed that its solutions in commercial xylene, when exposed at 75° to a stream of oxygen, in presence of acetic anhydride (added to accelerate reaction) and a cobalt catalyst, gave m- and p-toluic acid, together with neutral liquids which were clearly not derived from the rubber. For instance, when a solution of 675 g. of rubber in 6075 g. of xylene was mixed with 844 cc. of acetic anhydride and 42 g. of cobalt naphthenate, and the mixture (in 4 batches) was treated at 75° for 2 days with a stream of oxygen, there were obtained, respectively, (1) by extraction of the xylene solution with 10% caustic alkali and (2) by subsequent distillation at approximately 1 mm. pressure of the volatile product from the residual xylene liquor, about 10 g. of crystalline acid and 80 g. of volatile neutral oxidation products. The acid was toluic acid (found: C, 70.6; H, 6.1; equiv., 135; calculated for C8H8O2: C, 70.55; H, 5.95%; equiv. 136), from which samples of both the m- and the p-isomeride (m. p. 110° and 176°, respectively) were isolated by fractional crystallization.
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