Formation of iodinated trihalomethanes and haloacetic acids from aromatic iodinated disinfection byproducts during chloramination.

Iodinated disinfection byproducts (DBPs) are widely present in disinfected drinking waters and wastewater effluents, and they have drawn increasing concern owing to their high toxicity. To date, the reported iodinated DBPs mainly include aliphatic and aromatic ones, and iodinated trihalomethanes (THMs) and haloacetic acids (HAAs) are the most commonly detected aliphatic iodinated DBPs in disinfected waters. In this study, the formation of iodinated THMs and HAAs from aromatic iodinated DBPs during chloramination was investigated. The decomposition kinetics of the aromatic iodinated DBPs and the formation of iodinated THMs and HAAs were studied, the formation pathways of iodinated THMs and HAAs from the aromatic iodinated DBPs were explored, the factors affecting the formation were examined, and the toxicity change was evaluated. The results revealed that four aromatic iodinated DBPs (2,4,6-triiodophenol, 3,5-diiodo-4-hydroxybenzaldehyde, 3,5-diiodosalicylic acid, and 2,6-diiodo-4-nitrophenol) all underwent transformation to form triiodomethane (TIM), monoiodoacetic acid (MIAA), and diiodoacetic acid (DIAA) during chloramination. The decomposition of the aromatic iodinated DBPs all followed a pseudo-first-order decay during chloramination, and the rank order of the decomposition rate constants was as follows: 2,4,6-triiodophenol > 3,5-diiodo-4-hydroxybenzaldehyde ≥ 3,5-diiodosalicylic acid > 2,6-diiodo-4-nitrophenol. Several polar iodinated intermediates were detected and identified (e.g., 2,6-diiodo-1,4-benzoquinone and iodobutenedioic acid) during chloramination of 2,4,6-triiodophenol, based on which the formation pathways of TIM, MIAA, and DIAA from 2,4,6-triiodophenol during chloramination were proposed and further validated. The results also revealed that monochloramine dose, pH, temperature, and short free chlorine contact time all affected the formation of TIM, MIAA, and DIAA from 2,4,6-triiodophenol during chloramination. The cytotoxicity order of the eight iodinated DBPs was MIAA > 2,6-diiodo-4-nitrophenol > 2,4,6-triiodophenol > 2,6-diiodo-1,4-benzoquinone > DIAA ≥ 3,5-diiodosalicylic acid >3,5-diiodo-4-hydroxybenzaldehyde > TIM. The toxicity of the chloraminated 2,4,6-triiiodophenol sample first decreased and then increased over time due to the transformation.