Predicting total organic halide formation from drinking water chlorination using quantitative structure–property relationships

Abstract

Chlorinating water which contains dissolved organic matter (DOM) produces disinfection byproducts, the majority of unknown structure. Hence, the total organic halide (TOX) measurement is used as a surrogate for toxic disinfection byproducts. This work derives a robust quantitative structure–property relationship (QSPR) for predicting the TOX formation potential of model compounds. Literature data for 49 compounds were used to train the QSPR in moles of chlorine per mole of compound (Cp) (mol-Cl/mol-Cp). The resulting QSPR has four descriptors, calibration of 0.72 and standard deviation of estimation of 0.43 mol-Cl/mol-Cp. Internal and external validation indicate that the QSPR has good predictive power and low bias (<1%). Applying this QSPR to predict TOX formation by DOM surrogates – tannic acid, two model fulvic acids and two agent-based model assemblages – gave a predicted TOX range of 136–184 µg-Cl/mg-C, consistent with experimental data for DOM, which ranged from 78 to 192 µg-Cl/mg-C. However, the limited structural variation in the training data may limit QSPR applicability; studies of more sulfur-containing compounds, heterocyclic compounds and high molecular weight compounds could lead to a more widely applicable QSPR.

Keywords:

• total organic halides
• chlorination
• quantitative structure–property relationship
• fulvic acid
• dissolved organic matter

Acknowledgements

The authors are grateful to Department of Chemistry and Chemical Biology and the National Science Foundation (NSF) (#NSF DEB 0113570) for funding. Thanks to Dr David Reckhow of the Department of Civil and Environmental Engineering at the University of Massachusetts for inspiring the project and providing data access, and to two anonymous reviewers for helpful comments.