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Alkaline Permanganate Oxidation of Methylated and Unmethylated Fulvic Acid¹

ABSTRACT

The alkaline permanganate oxidation of humic and fulvic acids yields small amounts of benzene polycarboxylic acids that range from the di- to the hexa-form. Low yields may be due to the presence of electron-donating substituents, such as OH groups, on aromatic rings. To make the rings less susceptible to destruction by alkaline KMnO₄, we attempted to reduce the electron-donating effect by converting OH groups via methylation to OCH₃ groups. The alkaline permanganate oxidation of methylated FA, however, yielded the same types and similar amounts of benzene carboxylic acids as that of the untreated FA. Failure of methylation to increase the variety and yield of oxidation products may be due to inability to either methylate all (phenolic) OH groups or, more likely, to reduce electron-donating effects sufficiently.

¹ Contribution no. 314. Soil Research Institute, Can. Dep. of Agr. Ottawa, Ontario.

² Senior Research Scientist and Senior Technician, respectively.

Received for publication August 19, 1969. Accepted for publication September 22, 1969.