title: Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds.
abstract: The potential formation of nitrogenous disinfection byproducts (N-DBPs) was investigated from the chloramination of nitrogenous and non-nitrogenous aromatic compounds. All molecules led to the formation of known N-DBPs (e.g., dichloroacetonitrile, dichloroacetamide) with various production yields. Resorcinol, a major precursor of chloroform, also formed di/trichloroacetonitrile, di/trichloroacetamide, and haloacetic acids, indicating that it is a precursor of both N-DBPs and carbonaceous DBPs (C-DBPs) upon chloramination. More detailed experiments were conducted on resorcinol to understand N-DBPs formation mechanisms and to identify reaction intermediates. Based on the accurate mass from high resolution Quadrupole Time-of-Flight GC-MS (GC-QTOF) and fragmentation patterns from electronic impact and positive chemical ionization modes, several products were tentatively identified as nitrogenous heterocyclic compounds (e.g., 3-chloro-5-hydroxy-1H-pyrrole-2-one with dichloromethyl group, 3-chloro-2,5-pyrroledione). These products were structurally similar to the heterocyclic compounds formed during chlorination, such as the highly mutagenic MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone) or halogenated pyrroles. To our knowledge, this is the first time that the formation of halogenated nitrogenous heterocyclic compounds is reported from chloramination process. The formation of these nitrogenous byproducts during chloramination might be of concern considering their potential toxicity.
authors.affiliation: Curtin Water Quality Research Centre, Department of Chemistry, Curtin University , GPO Box U1987, Perth, Western Australia 6845, Australia.
authors.forename: Maolida
authors.identifier: 0000-0002-0004-2003
authors.initials: M
authors.lastname: Nihemaiti
authors.affiliation: LEESU (UMR MA 102), Université Paris-Est - AgroParisTech , 61 avenue du Général de Gaulle, 94010 Créteil cedex, France.
authors.forename: Julien
authors.initials: J
authors.lastname: Le Roux
authors.affiliation: Department of Chemical and Environmental Engineering, The University of Arizona , P.O. Box 210011, Tucson, Arizona, United States.
authors.forename: Christiane
authors.initials: C
authors.lastname: Hoppe-Jones
authors.affiliation: Department of Civil and Environmental Engineering, University of Massachusetts Amherst , 18 Marston Hall, 130 Natural Resources Rd., Amherst, Massachusetts 01003-9293, United States.
authors.forename: David A
authors.initials: DA
authors.lastname: Reckhow
authors.affiliation: Curtin Water Quality Research Centre, Department of Chemistry, Curtin University , GPO Box U1987, Perth, Western Australia 6845, Australia.
authors.forename: Jean-Philippe
authors.initials: JP
authors.lastname: Croué
mesh_terms: D002700:Chloramines / Q000737:chemistry*; D004202:Disinfectants / Q000737:chemistry; D004203:Disinfection; D054879:Halogenation; D009584:Nitrogen / Q000737:chemistry*; D014874:Water Pollutants, Chemical; D018508:Water Purification
chemical_list: D002700:Chloramines; D004202:Disinfectants; D014874:Water Pollutants, Chemical; D009584:Nitrogen