Photoconversion of Chlorinated Saline Wastewater DBPs in Receiving Seawater is Overall a Detoxification Process

Chlorine disinfection of wastewater effluents rich in bromide and iodide ions results in the formation of relatively toxic bromo- and iodo-disinfection byproducts (DBPs), especially highly toxic bromophenolic and iodophenolic DBPs, which could harm the marine ecosystem when they are discharged into receiving seawater along with the wastewater effluents. In this study, we investigated the conversion of three individual halophenolic DBPs (5-bromosalicylic acid, 2,5-dibromohydroquinone, and 2,4,6-triiodophenol) and two chlorinated saline wastewater DBP mixtures in seawater. The conversion products were analyzed with ultra performance liquid chromatography/electrospray ionization-triple quadrupole mass spectrometry, and the conversion of overall halo-DBPs in the wastewater DBP mixtures was monitored by measuring total organic halogen. The photoconversion-induced variations in the toxicity were evaluated using the embryos of a marine polychaete. Halophenolic DBPs were found to undergo photoconversion in seawater. The conversion was triggered by photonucleophilic substitution: bromophenolic and iodophenolic DBPs were converted to their chlorophenolic or hydroxyphenolic analogues, via substituting the bromine and iodine atoms with chloride or hydroxide ions in seawater; chlorophenolic DBPs were converted to their hydroxyphenolic analogues, via substituting the chlorine atoms with hydroxide ions in seawater. The hydroxyphenolic analogues thus formed further decomposed and finally cleaved to aliphatic compounds. The photoconversion of chlorinated saline wastewater DBPs in receiving seawater was overall a dehalogenation and detoxification process.