The Oxidation of Some Dibasic Acids

Abstract

This paper gives the results obtained when hydrogen peroxide is employed to oxidize malonic, tartronic, succinic, malic, tartaric, maleic and fumaric acids. The rate of reaction for each has been determined and compared with previous findings for other compounds. The mode of oxidation suggests in each case a complex through which decomposition occurs; the rates of reaction indicate the comparability of saturated acids having the same number of carbon atoms, the constancy of mono-hydroxylization in its velocity influence, and the diverse effects of hydrogen ion concentration. The effects of geometrical isomerism and the ethylenic linkage are well-marked. The formation of peracids is to be regarded in the nature of a side-reaction in these oxidations.

The Haloform Reaction.

“…Thus, Wallach (198) found that in the formation of bromoform from hypobromite and acetone in very dilute solutions, the reaction was slow and that carbon tetrabromide was the chief product. This influence of the pH on the course of reactions involving hypohalites is frequently noticed (105,119,79).…”

“…The haloform reaction has also been employed in the quantitative estimation of lactic acid (96), levulinic acid (157), and pyruvic acid (79).…”

Synthesis of Tartaric Acid

“…yield was obtained when the reaction was carried out in the presence of a trace of tungstic acid. Without any catalyst the yields were extremely low (17). Hydrogen peroxide is known to react with tungstic oxide to form the higher unstable pertungstic acids (27).…”