Acetonitrile and N-Chloroacetamide Formation from the Reaction of Acetaldehyde and Monochloramine

Susana Y. Kimura, Trang Nha Vu, Yukako Komaki, Michael J. Plewa, Benito J. Mariñas

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Nitriles and amides are two classes of nitrogenous disinfection byproducts (DBPs) associated with chloramination that are more cytotoxic and genotoxic than regulated DBPs. Monochloramine reacts with acetaldehyde, a common ozone and free chlorine disinfection byproduct, to form 1-(chloroamino)ethanol. Equilibrium (K1) and forward and reverse rate (k1,k-1) constants for the reaction between initial reactants and 1-(chloroamino)ethanol were determined between 2 and 30 °C. Activation energies for k1 and k-1 were 3.04 and 45.2 kJ·mol-1, respectively, and enthalpy change for K1 was -42.1 kJ·mol-1. In parallel reactions, 1-(chloroamino)ethanol (1) slowly dehydrated (k2) to (chloroimino)ethane that further decomposed to acetonitrile and (2) was oxidized (k3) by monochloramine to produce N-chloroacetamide. Both reactions were acid/base catalyzed, and rate constants were characterized at 10, 18, and 25 °C. Modeling for drinking water distribution system conditions showed that N-chloroacetamide and acetonitrile concentrations were 5-9 times higher at pH 9.0 compared to 7.8. Furthermore, acetonitrile concentration was found to form 7-10 times higher than N-chloroacetamide under typical monochloramine and acetaldehyde concentrations. N-chloroacetamide cytotoxicity (LC50 = 1.78 × 10-3 M) was comparable to dichloroacetamide and trichloroacetamide, but less potent than N,2-dichloroacetamide and chloroacetamide. While N-chloroacetamide was not found to be genotoxic, N,2-dichloroacetamide genotoxic potency (5.19 × 10-3 M) was on the same order of magnitude as chloroacetamide and trichloroacetamide.

Original languageEnglish (US)
Pages (from-to)9954-9963
Number of pages10
JournalEnvironmental Science and Technology
Issue number16
StatePublished - Jul 13 2015

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry


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