Chlorination of Amino Acids: Reaction Pathways and Reaction Rates
dc.contributor.author | How, Zuo Tong | |
dc.contributor.author | Linge, Kathryn | |
dc.contributor.author | Busetti, Francesco | |
dc.contributor.author | Joll, Cynthia | |
dc.date.accessioned | 2017-03-24T11:53:48Z | |
dc.date.available | 2017-03-24T11:53:48Z | |
dc.date.created | 2017-03-23T06:59:50Z | |
dc.date.issued | 2017 | |
dc.identifier.citation | How, Z. and Linge, K. and Busetti, F. and Joll, C. 2017. Chlorination of Amino Acids: Reaction Pathways and Reaction Rates. Environmental Science & Technology. 51 (9): pp. 4870-4876. | |
dc.identifier.uri | http://hdl.handle.net/20.500.11937/51516 | |
dc.identifier.doi | 10.1021/acs.est.6b04440 | |
dc.description.abstract |
Chlorination of amino acids can result in the formation of organic monochloramines or organic dichloramines, depending on the chlorine to amino acid ratio (Cl:AA). After formation, organic chloramines degrade into aldehydes, nitriles and N-chloraldimines. In this paper, the formation of organic chloramines from chlorination of lysine, tyrosine and valine were investigated. Chlorination of tyrosine and lysine demonstrated that the presence of a reactive secondary group can increase the Cl:AA ratio required for the formation of N,N-dichloramines, and potentially alter the reaction pathways between chlorine and amino acids, resulting in the formation of unexpected by-products. In a detailed investigation, we report rate constants for all reactions in the chlorination of valine, for the first time, using experimental results and modelling. At Cl:AA = 2.8, the chlorine was found to first react quickly with valine (5.4x104 M-1 s-1) to form N-monochlorovaline, with a slower subsequent reaction with N-monochlorovaline to form N,N-dichlorovaline (4.9x102 M-1 s-1), although some N-monochlorovaline degraded into isobutyraldehyde (1.0x10-4 s-1). The N,N-dichlorovaline then competitively degraded into isobutyronitrile (1.3x10-4 s-1) and N-chloroisobutyraldimine (1.2x10-4 s-1). In conventional drinking water disinfection, N-chloroisobutyraldimine can potentially be formed in concentrations higher than its odour threshold concentration, resulting in aesthetic challenges and an unknown health risk. | |
dc.publisher | American Chemical Society | |
dc.relation.sponsoredby | http://purl.org/au-research/grants/arc/LP110100548 | |
dc.relation.sponsoredby | http://purl.org/au-research/grants/arc/LP130100602 | |
dc.title | Chlorination of Amino Acids: Reaction Pathways and Reaction Rates | |
dc.type | Journal Article | |
dcterms.source.issn | 1520-5851 | |
dcterms.source.title | Environmental Science & Technology | |
curtin.department | Department of Chemistry | |
curtin.accessStatus | Open access |