Related Experiment Video
Updated: Jul 11, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Dissolved organic nitrogen as a precursor for chloroform, dichloroacetonitrile, N-nitrosodimethylamine, and
Wontae Lee1, Paul Westerhoff, Jean-Philippe Croué
1HDR Engineering, Inc., 3200 East Camelback Road, Suite 350, Phoenix, Arizona 85018, USA. wontae.lee@hdrinc.com
Abstract:
Nitrogen-containing disinfection byproducts (N-DBPs) are potentially toxic. This study assessed the formation of three N-DBPs (dichloroacetonitrile (DCAN), trichloronitromethane (TCNM), and N-nitrosodimethylamine (NDMA)) and one regulated DBP (chloroform) upon adding free chlorine and monochloramine into solutions containing different fractions (hydrophobic, transphilic, hydrophilic, and colloidal) of dissolved organic matter (DOM) isolates (n=17). We hypothesized that N-DBP formation would increase for organic matter enriched in organic nitrogen. Formation potential tests were conducted with free chlorine or preformed monochloramine. Chloramination formed, on average, 10 times lower chloroform concentrations, but 5 times higher DCAN concentrations, as compared with free chlorine addition. The formation of the two halogenated N-DBPs (DCAN and TCNM) increased as the dissolved organic carbon (DOC) to dissolved organic nitrogen (DON) ratio decreased upon adding free chlorine, but the N-DBP formation was relatively constant upon adding monochloramine. NDMA, a nonhalogenated N-DBP, formed on average 0.26 nmol per mg of DOC (4.5 nmol per mg of DON) upon adding monochloramine; no NDMA formation occurred upon adding free chlorine. NDMA formation increased as the DOC/DON ratio decreased (i.e., increasing nitrogen content of DOM). NDMA formation also increased as the amino sugar to aromatic ratio of DOM increased. The results support the hypothesis that DON promotes the formation of N-DBPs.
Related Concept Videos
Preparation of Nitriles
Preparation of Carboxylic Acids: Hydrolysis of Nitriles
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
2° Amines to N-Nitrosamines: Reaction with NaNO2
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
Preparation of Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...

