Related Experiment Video
Updated: Nov 2, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Formation and influence factors of halonitromethanes in chlorination of nitro-aromatic compounds
Junjie Wang1, Zhigang Li1, Shaoyang Hu1
1State Key Laboratory of Pollution Control and Resource Reuse, School of the Environment, Nanjing University, Nanjing, 210023, China.
Abstract:
Halonitromethanes (HNMs), typical nitrogenous disinfection byproducts generated during disinfection of chlorination and chloramination, are widely detected in drinking water. This study investigated the formation of two dominant HNMs, trichloronitromethane (TCNM) and dichloronitromethane (DCNM) during chlorination/chloramination of ten nitro-aromatic compounds (NACs), including six aromatic mono-nitro compounds, three aromatic di-nitro compounds and one aromatic tri-nitro compound. The results showed that 2-nitrophenol and 3-nitrophenol could be the main precursors of TCNM and DCNM, and the yields of TCNM were one order of magnitude higher than that of DCNM. HNMs formation in chlorination was much higher than that in chloramination. However, HNMs were hardly produced during chlorination and chloramination of the other eight NACs. In chlorination of 2-nitrophenol, a pH range of 5.0-7.0 facilitated the TCNM formation. Besides, the concentration of ferric and manganese ions had different influences on TCNM formation. While the concentration ranges were 0-2 mg/L, ferric ion significantly decreased TCNM formation but manganese ion had not any influence on TCNM formation. Contrary to a previous finding, nitrite significantly reduced TCNM formation, which implied that nitrite has different effects on TCNM formation from various precursors. Moreover, dissolved organic matter (DOM, 0-5 mg/L as C) significantly influenced the formation of TCNM in chlorination of 2-nitrophenol despite the low TCNM formation in chlorination of DOM. Several chlorinated intermediates were detected and identified as mono/di/tri-chloro-2-nitrophenol during chlorination of 2-nitrophenol. It is effectively to reduce the production of TCNM and DCNM formation from chlorination of 2-nitrophenol by controlling disinfection conditions in drinking water.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
08:43Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Related Concept Videos
Reactions at the Benzylic Position: Halogenation
Radical Halogenation: Thermodynamics
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
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...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene