A Study of the Oxidation of Naphtosulfonic Acid to the Quinone

Abstract

The purpose of this experiment was to determine, to a certain extent, whether the method of preparation of the 8-sulfonic acid of 2-methyl-1,4-naphthoquinone as carried out by Aaron Bendich and Erwin Chargaff [1] is of very limited or of more general applicability by the use of naphthalene rather than 2-methylnaphthalene as the initial compound. The successful method employed by Bendich and Chargaff was the oxidation of the sulfonamide by means of chromic acid in glacial acetic acid. . . . They had previously unsuccessfully attempted "to prepare the desired substance by direct sulfonation of 2-methyl-1,4-naphthoquinone with chlorosulfonic acid" and also "'by the oxidation of 2-methylnaphthalene-8-sulfonic acid in acetic acid with hydrogen peroxide or chromic acid." In the attempt to perform the direct oxidation, partial hydrolysis of the sulfonic acid occurred, as indicated by the formation of small amounts of 2-methyl-1,4-naphthoquinone. "The oxidation of 2-methyl-naphthalene-8-sulfonyl chloride likewise failed to yield products of sufficient purity." This thesis was likewise to include an attempt to oxidize naphthosulfonic acid directly; however, the work did not proceed beyond the preparation of 1,4-naphthoquinone-8-sulfonamide by the oxidation of naphthosulfonamide. [From Purpose of Research]