The Oxidation of Rubber by Hydrogen Peroxide

Abstract

Abstract It was noticed long ago that rubber changes during storage, and that it loses its valuable qualities. Many authors have tried to explain this phenomenon as a union of oxygen with rubber molecules. The most interesting work on this subject was the early work of Herbst (Ber., 39, 523 (1906)). Herbst blew air for 140 hours through benzene solutions of rubber and obtained two products, C10H16O3, as a main product, and C10H16O, as a very small admixture. Later Peachey and Leon (J. Soc. Chem. Ind., 31, 1103 (1912); 37, 55 (1918)) subjected rubber films to the action of oxygen and found that for each group of C10H16, four atoms of oxygen were added and one atom of carbon was liberated. These workers succeeded in separating several compounds with different degrees of oxidation, viz., C10H16O; C10H16O 4; C6H9O 2. Herbst thought that he had obtained an addition product of oxygen and rubber hydrocarbon, but Peachey considered that the compounds were the result of a splitting and depolymerization of the rubber molecules. Boswell (India-Rubber J., 54, 981, 987 (1922)) and his students investigated the phenomenon of oxidation of rubber and obtained different oxidation products for each oxidizing agent. A solution of rubber in carbon tetrachloride oxidized by means of potassium permanganate in the absence of air (in carbon dioxide) gave a product of the formula, C25H40O, which in turn was readily oxidized in air to C30H48O2. Using 3% hydrogen peroxide as an oxidizing agent, Boswell obtained a product with the formula, C30H48O, which in turn was easily oxidized to C25H40O2.