During chlorination or chloramination (i.e., application of reactive chlorine or Cl[I]) primary amines are rapidly di-chlorinated. Three different decay pathways for these organo chloramines explain the formation of nitrile, aldehyde and halonitroalkane byproducts (see below for cyanogen chloride, formaldehyde and chloropicrin formation from chlorination/chloramination of monomethylamine (MMA)).
Nitrile and aldehyde formation was much more significant than halonitroalkane formation, although the formation of the latter compounds may still be significant due to their toxicity. Our research indicated that for longer alkyl chain primary amines (e.g., propylamine (PA)) that might better mimic primary amine groups in dissolved organic nitrogen, nitrile and aldehyde formation was much more significant (see below).
Joo, S.-H.; Mitch, W.A. Nitrile, aldehyde and halonitroalkane formation
during chlorination/chloramination of primary amines. Environ. Sci. Technol., 2007,
41 (4), 1288-1296
