Activated carbon catalyzed nitrosamine formation via amine nitrosation

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Callura, Jonathan C.
Huang, Ching-Hua
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Nitrosamines have garnered increasing attention from researchers and policy makers in recent years due to potential human health implications associated with their unintentional formation in water and wastewater treatment facilities. This work addresses a crucial nitrosamine formation pathway concerning the catalysis of amine nitrosation by activated carbon materials whose use is widespread in municipal and industrial systems. Experimental results show that this catalysis is highly pH dependent, with maximum formation achieved near the pKa value for each of the secondary amines tested. This result suggests that the overall formation potential is governed by individual amine properties and their interactions with carbon surfaces, rather than solely nitrite speciation as previously reported. Formation of the most commonly studied nitrosamine, N-nitrosodimethylamine, was shown to be highly dependent on initial dimethylamine (DMA) solution concentration, with yields of approximately 0.11% of the spiked secondary amine at pH 7.5. Morpholine and dibutylamine, larger and bulkier secondary amines, formed their corresponding nitrosamines at higher yields than DMA (0.21% and 1.69%, respectively). Additionally, select tertiary amines were shown to be capable of undergoing nitrosation on the same order of magnitude as the secondary amines under neutral conditions in the presence of activated carbons. The magnitude of these results indicates that greater attention should be paid to this previously overlooked mechanism for nitrosamine formation.
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