Chlorination of tramadol: Reaction kinetics, mechanism and genotoxicity evaluation

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	Chlorination of tramadol: Reaction kinetics, mechanism and genotoxicity evaluation
	Cheng, Hanyang; Song, Dean; Chang, Yangyang; Liu, Huijuan; Qu, Jiuhui
刊名	CHEMOSPHERE
	2015-11
卷号	141 期号:0 页码:282-289
关键词	Chlorination Tramadol Kinetics Pathway and mechanism Genotoxicity
英文摘要	Tramadol (TRA) is one of the most detected analgesics in environmental matrices, and it is of high significance to study the reactivity of TRA during chlorination considering its potential toxicity to the environment. The chlorine/TRA reaction is first order with respect to the TRA concentration, and a combination of first-order and second-order with respect to chlorine concentration. The pH dependence of the observed rate constants (k(obs)) showed that the TRA oxidation reactivity increased with increasing pH. /cobs can be quantitatively described by considering all active species including C-12, CL2O and HOCI, and the individual rate constants of HOCl/TRA(0), HOCl/TRAH(+), Cl-2/TRA and Cl2O/TRA reactions were calculated to be (2.61 +/- 0.29) x 10(3) M-1 s(-1), 14.73 +/- 4.17 M-1 s(-1), (3.93 +/- 0.34) x 10(5) M-1 s(-1) and (5.66 +/- 1.83) x 10(6) M(-1)s(-1), respectively. Eleven degradation products were detected with UPLC-Q-TOF-MS, and the corresponding structures of eight products found under various pH conditions were proposed. The amine group was proposed to be the initial attack site under alkaline pH conditions, where reaction of the deprotonated amine group with HOCI is favorable. Under acidic and neutral pH conditions, however, two possible reaction pathways were proposed. One is an electrophilic substitution on the aromatic ring, and another is an electrophilic substitution on the nitrogen, leading to an N-chlorinated intermediate, which can be further oxidized. Finally, the SOS/umu test showed that the genotoxicity of TRA chlorination products increased with increasing dosage of chlorine, which was mostly attributed to the formation of some chlorine substitution products. (C) 2015 Elsevier Ltd. All rights reserved.
研究领域[WOS]	Environmental Sciences
WOS记录号	WOS:000363824400039
公开日期	2016-03-15
内容类型	期刊论文
源URL	[http://ir.rcees.ac.cn/handle/311016/32739]
专题	生态环境研究中心_环境水质学国家重点实验室
推荐引用方式 GB/T 7714	Cheng, Hanyang,Song, Dean,Chang, Yangyang,et al. Chlorination of tramadol: Reaction kinetics, mechanism and genotoxicity evaluation[J]. CHEMOSPHERE,2015,141(0):282-289.
APA	Cheng, Hanyang,Song, Dean,Chang, Yangyang,Liu, Huijuan,&Qu, Jiuhui.(2015).Chlorination of tramadol: Reaction kinetics, mechanism and genotoxicity evaluation.CHEMOSPHERE,141(0),282-289.
MLA	Cheng, Hanyang,et al."Chlorination of tramadol: Reaction kinetics, mechanism and genotoxicity evaluation".CHEMOSPHERE 141.0(2015):282-289.