Mechanisms of Phenol Ozonation—Kinetics of Formation of Primary and Secondary Reaction Products

Abstract

Organic acids are part of assimilable organic carbon (AOC) formed from natural organic matter (NOM) during ozonation for drinking water production. To elucidate the formation of organic acids, phenol as surrogate compound for NOM was ozonated while suppressing reactions of ^·OH radicals by addition of tert-butanol. Batch experiments show benzoquinone (40 and 18%), catechol (33 and 1%), cis,cis-muconic acid (6 and 3%), and hydroquinone (2 and 7%) to be the most abundant primary products at pH 7 and 3, respectively. The tertiary product oxalic acid was obtained in similar yields from phenol ozonation (0.8%) as during ozonation of lake water (1.6%). Together with other low molecular weight organic acids it was formed upon small ozone exposures, as was shown by time-dependent experiments in time ranges of 0.4–23 and 0.07–1.0 seconds for pH 3 and 7.25, respectively.

Keywords:

• Ozone
• Phenol
• Organic Acids
• Assimilable Organic Carbon
• Kinetics

ACKNOWLEDGMENTS

The authors thank Elisabeth Salhi for technical assistance, Werner Angst for advice in MSMS-data interpretation, and Professor Clemens von Sonntag and Yunho Lee for fruitful discussions.