Can reductive deiodination improve the sorption of iodinated X-ray contrast media to aquifer material during bank filtration?

Iodinated X-ray contrast media (ICM) as well as their aerobic transformation products (TPs), are highly polar triiodobenzoic acid derivatives, ubiquitously found in the urban water cycle. Based on their polarity, their sorption affinity to sediment and soil is negligible. However, we hypothesize that the iodine atoms bound to the benzene ring play a decisive role for sorption, due to their large atom radius, high electron number and symmetrical positioning within the aromatic system. The aim of this study is to investigate, if the (partial) deiodination, occurring during anoxic/anaerobic bank filtration, improves the sorption to aquifer material. Tri, di, mono and deiodinated structures of two ICMs (iopromide and diatrizoate) and one precursor/TP of ICM (5-amino-2,4,6-triiodoisophtalic acid) were tested in batch experiments, using two aquifer sands and a loam soil with and without organic matter. The di, mono and deiodinated structures were produced by (partial) deiodination of the triiodinated initial compounds. The results demonstrated that the (partial) deiodination increases the sorption to all tested sorbents, even though the theoretical polarity increases with decreasing number of iodine atoms. Whereas lignite particles positively affected the sorption, mineral components decreased it. Kinetics tests show biphasic sorption for the deiodinated derivatives. We have concluded that iodine affects the sorption by sterical hindrance, repulsive forces, resonance and inductive effects, depending on the number and position of iodine, side chain characteristics and composition of the sorbent material. Our study has revealed an increased sorption potential of ICMs and their iodinated TPs to aquifer material during anoxic/anaerobic bank filtration as a result of (partial) deiodination, whereby a complete deiodination is not necessary for efficient removal by sorption. Furthermore, it suggests that the combination of an initial aerobic (side chain transformations) and a subsequent anoxic/anaerobic (deiodination) redox milieu supports the sorption potential.