Quantitative structure-property relationships for predicting sorption of pharmaceuticals to sewage sludge during waste water treatment processes

摘要

Understanding the sorption of pharmaceuticals to sewage sludge during waste water treatment processes is important for understanding their environmental fate and in risk assessments. The degree of sorption is defined by the sludge/water partition coefficient (Kd). Experimental Kd values (n = 297) for active pharmaceutical ingredients (n = 148) in primary and activated sludge were collected from literature. The compounds were classified by their charge at pH 7.4 (44 uncharged, 60 positively and 28 negatively charged, and 16 zwitterions). Univariate models relating log Kd to log Kow for each charge class showed weak correlations (maximum R² = 0.51 for positively charged) with no overall correlation for the combined dataset (R² = 0.04). Weaker correlations were found when relating log Kd to log Dow. Three sets of molecular descriptors (Molecular Operating Environment, VolSurf and ParaSurf) encoding a range of physico-chemical properties were used to derive multivariate models using stepwise regression, partial least squares and Bayesian artificial neural networks (ANN). The best predictive performance was obtained with ANN, with R² = 0.62–0.69 for these descriptors using the complete dataset. Use of more complex Vsurf and ParaSurf descriptors showed little improvement over Molecular Operating Environment descriptors. The most influential descriptors in the ANN models, identified by automatic relevance determination, highlighted the importance of hydrophobicity, charge and molecular shape effects in these sorbate-sorbent interactions. The heterogeneous nature of the different sewage sludges used to measure Kd limited the predictability of sorption from physico-chemical properties of the pharmaceuticals alone. Standardization of test materials for the measurement of Kd would improve comparability of data from different studies, in the long-term leading to better quality environmental risk assessments.