Re-Examining the Role of Dichloramine in High-Yield N-Nitrosodimethylamine Formation from N,N-Dimethyl-α-arylamines

doi:10.1021/ACS.ESTLETT.7B00572

Paper

Re-Examining the Role of Dichloramine in High-Yield N-Nitrosodimethylamine Formation from N,N-Dimethyl-α-arylamines

Published Jan 22, 2018 · M. Huang, Shi-Yue Huang, Daniel L. McCurry

Environmental Science and Technology Letters

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39

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Abstract

N-Nitrosodimethylamine (NDMA) is a potent carcinogen associated with chloramination of wastewater and wastewater-impacted drinking waters. Substantial effort has been expended to identify the precursors and mechanisms leading to NDMA formation. One of the major discoveries has been that molecules in the N,N-dimethyl-α-arylamine class, including the common pharmaceutical ranitidine, form NDMA in high yield during chloramination. Simultaneously, it was hypothesized that these precursors react with monochloramine, the dominant species in most chloramine mixtures, to form NDMA. This monochloramine hypothesis contradicts past mechanistic work with simple secondary amines, as well as practical experience showing that minimization of dichloramine reduces the level of NDMA formation during wastewater reuse and drinking water treatment. In this work, we address the contradiction between practical experience and model precursor studies by showing that N,N-dimethyl-α-arylamines form NDMA chiefly via reactions with d...

Study Snapshot

N,N-dimethyl--arylamines form NDMA chiefly via reactions with dichloramine, contradicting the monochloramine hypothesis and reducing NDMA formation during wastewater reuse and drinking water treatment.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Re-Examining the Role of Dichloramine in High-Yield N-Nitrosodimethylamine Formation from N,N-Dimethyl-α-arylamines

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References

Citations

Natural vs. anthropogenic sources of N-Nitrosodimethylamine precursors in surface water.

The dominant source of NDMA precursors in surface water may be wastewater near wastewater outfalls, indicating that wastewater-derived precursors may not be responsible for NDMA formation in drinking water sources further downstream.

Bacterial dealkylation of benzalkonium chlorides in wastewater produces benzyldimethylamine, a potent N-nitrosodimethylamine precursor.

Bacterial dealkylation of benzalkonium chlorides in wastewater produces benzyldimethylamine (BDMA), which accounts for 4-to-38% of the NDMA precursor pool in municipal wastewater effluents.

Minimizing N-Nitrosodimethylamine Formation During Disinfection of Blended Seawater and Wastewater Effluent

Disinfecting seawater before blending with wastewater can minimize N-nitrosodimethylamine formation during disinfection of blended wastewater-seawater.

Pressure-driven distillation using air-trapping membranes for fast and selective water purification

Air-trapping membranes with sub-200-nm air layers effectively purify water without sacrificing salt rejection, enabling high-throughput ultraselective separations.

Chloramination of Nitromethane: Incomplete Chlorination and Unexpected Substitution Reaction.

Nitromethane chloramination in wastewater treatment produces a range of products, with chloropicrin being the principal product, but also monochloronitromethane and dichloronitromethane, depending on pH and reaction time.