Abstract
The behavior of reaction products formed by the ozonation of naphthoresorcinol and of eight carbonyl compounds which were identified in the reaction mixture of ozonated naphthoresorcinol was investigated. During ozonation of naphthoresorcinol, o-phthalic acid and muconic acid reached the maximum concentrations at the beginning of the ozonation, followed by maleic acid and glyoxal and finally by mesoxalic acid, oxalic acid and formic acid increased during further ozonation. No change of the concentration of glyoxylic acid was observed during the ozonation. The ozonation of the eight carbonyl compounds identified demonstrated the following degradation pathways. The ozonolysis of o-phthalic acid occurred through three pathways, leading to maleic acid, mesoxalic acid and glyoxal, which were further degraded to glyoxylic acid, oxalic acid and formic acid. However, muconic acid was not formed by the ozonation of o-phthalic acid and degraded by two pathways through each of maleic acid and glyoxal. Gas chromatography-mass spectrometry indicated that o-carboxy-α-hydroxycinnamic acid may be one of the intermediates to o-phthalic acid or muconic acid. The degradation mechanisms of naphthoresorcinol by aqueous ozonation are discussed on the basis of these results.
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