Reactions With Disinfectants
Published in Richard A. Larson, Eric J. Weber, Reaction Mechanisms in Environmental Organic Chemistry, 2018
Richard A. Larson, Eric J. Weber
Thiols were oxidized by HOCl to the corresponding sulfonic acids; thus, cysteine afforded cysteic acid (Equation 5.6: Ingols et al., 1953). This is in contrast to the behavior of NH2Cl, which oxidized cysteine only to the disulfide. Thiophenes were chlorinated in the nucleus as well as undergoing partial oxidation of the sulfur atom (Equation 5.7: Morton, 1946), whereas more highly condensed sulfur heterocycles such as benzo[b] thiophene (1) and dibenzothiophene (2) were oxidized to the sulfone and sulfoxide almost to the exclusion of chlorination (Lin and Carlson, 1984). Tetrachlorothiophene (3), 3–formyl–2,4,5–trichlorothiophene (4), and 3–acetyl–2,4,5– trichlorothiophene (5) were identified in a spent liquor from the bleaching of a softwood kraft pulp (McKague et al., 1989); the precursors of these chemicals were not conjectured upon.
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