The chlorination of the common polyphenol resorcinol via exposure to hypochlorous acid has been studied well with respect to mechanism and product distribution. Heasley, et al. (Env. Tox. & Chem, 1989) report the predominance of the trichlorinated product at mid- to low-pH conditions. Rebenne, et al. (Env. Sci. & Tech, 1996) suggest a sequential chlorination mechanism and report kinetic rate constants indicating a comparable reaction rate for each chlorination step. Such a mechanism would predict the predominance of mono- and dichlorinated products from reaction mixtures of the composition reported by Heasley. To investigate this conflict in the literature, the reaction was modeled numerically per the proposed mechanism using Wolfram Mathematica�.  The product distribution predicted by this model will be compared to experimental product distribution, and an analysis of this comparison will be the subject of this presentation.

Modeling the mechanism of the chlorination of resorcinol

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.