|
|
|
| Products and pathways of 2-bromophenol oxidation by potassium permanganate |
| PANG Su-yan1,2, YANG Yue2, JIANG Cheng-chun3, ZHOU Yang4, JIANG Jin4, MA Jun4 |
1. School of Municipal and Environmental Engineering, Jilin Jianzhu University, Changchun 130118, China;
2. College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China;
3. School of Civil and Environmental Engineering, Shenzhen Polytechnic, Shenzhen 518055, China;
4. State Key Laboratory of Urban Water Resource and Environment, Harbin Institute of Technology, Harbin 150090, China |
|
|
|
|
Abstract The purpose of this article was to investigate the mechanism responsible for the formation of brominated polymeric products from oxidation of bromophenols by aqueous potassium permanganate. Experiments were conducted to determine brominated oxidation products of 2-bromophenol by aqueous potassium permanganate using liquid chromatography-triple quadrupole mass spectrometry (LC-MS/MS). The results showed that four polymeric products of m/z 341/343 (at m/z 79) and 343/345 (at m/z 81) containing two bromine atoms were detected by the precursor ion scan (PIS) approach at m/z 79 and 81, respectively, and their abundance was about 1:1, consistent with the natural isotope of bromine atom. The four polymeric products were isomers, and they were formed by the C-O and C-C coupling of 2-bromophenoxy radicals, where the C-C coupling products eluted faster than the C-O coupling ones in LC-MS/MS. According to phenolic coupling theory, there would be eight brominated polymeric products. However, they were partially detected, probably due to the difference in coupling rates of phenoxy radicals.
|
|
Received: 03 May 2017
|
|
|
|
|
|
| [1] |
Sim W J, Lee I S, Choi S D, et al. Distribution and formation of chlorophenols and bromophenols in marine and riverine environments[J]. Chemosphere, 2009,77:552-558.
|
| [2] |
Xiong J, Li G, An T, et al. Emission patterns and risk assessment of polybrominated diphenyl ethers and bromophenols in water and sediments from the Beijiang River, South China[J]. Environ. Pollut., 2016,219:596-603.
|
| [3] |
Hassenklover T, Predehl S, Pilli J, et al. Bromophenols, both present in marine organisms and in industrial flame retardants, disturb cellular Ca2+ signaling in neuroendocrine cells (PC12)[J]. Aquat. Toxicol., 2006,76:37-45.
|
| [4] |
Kammann U, Vobach M, Wosniok W. Toxic effects of brominated iodoles and phenols on zebrafish embryos. Arch[J]. Environ. Contam. Toxicol., 2006,51:97-102.
|
| [5] |
Bruchajzer E, Szymanska J A, Piotrowski J K. Acute and subacute nephrotoxicity of 2-bromophenol in rats[J]. Toxicol. Letters, 2002,134:245-252.
|
| [6] |
Yang M, Zhang X. Comparative developmental toxicity of new aromatic halogenated DBPs in a chlorinated saline sewage effluent to the marine polychaete platynereis dumerilii[J]. Environ. Sci. Technol., 2013,47:10868-10876.
|
| [7] |
Acero J L, Piriou P, von Gunten U. Kinetics and mechanisms of formation of bromophenols during drinking water chlorination:Assessment of taste and odor development[J]. Water Res., 2005,39:2979-2993.
|
| [8] |
Lin K, Yan C, Gan J. Production of hydroxylated polybrominated diphenyl ethers (OH-PEDEs) from bromophenols by manganese dioxide[J]. Environ. Sci. Technol., 2014,48:263-271.
|
| [9] |
Eriksson J, Rahm S, Green N, et al. Photochemical transformations of tetrabromobisphenol A and related phenols in water[J]. Chemosphere, 2004,54:117-126.
|
| [10] |
Liu H, Zhao H, Quan X, et al. Formation of 2'-hydroxy-2, 3',4,5'-tetrabromodipheyl ether (2'-HO-BDE68) from 2,4-dibromophenol in aqueous solution under simulated sunlight irradiation[J]. Chemosphere, 2011,84:512-518.
|
| [11] |
Saeed A, Altarawneh M, Dlugogorski B Z. Photodecomposition of bromophenols[J]. Chemosphere, 2016,150:749-758.
|
| [12] |
Zhu Q, Igarashi M, Sasaki M, et al. Degradation and debromination of bromophenols using a free-base porphyrin and metalloporphyrins as photosensitizers under conditions of visible light irradiation in the absence and presence of humic substances[J]. Appl. Catal. B-Environ., 2016,183:61-68.
|
| [13] |
Xie B, Li X, Huang X, et al. Enhanced debromination of 4-bromophenol by the UV/sulfite process:Efficiency and mechanism[J]. J. Environ. Sci., 2017,54:231-238.
|
| [14] |
Guan C, Jiang Jin, Luo C, et al. Oxidation kinetics of bromophenols by nonradical activation of peroxydisulfate in the presence of carbon nanotube and formation of brominated polymeric products. Environ. Sci. Technol., 2017,51:10718-10728.
|
| [15] |
Jiang J, Gao Y, Pang S Y, et al. Oxidation of bromophenols and formation of brominated polymeric products of concern during water treatment with potassium permanganate[J]. Environ. Sci. Technol., 2014,48:10850-10858.
|
| [16] |
Zhang X, Talley J W, Boggess B, et al. Fast selective detection of polar brominated disinfection byproducts in drinking water using precursor ion scans[J]. Environ. Sci. Technol., 2008,42:6598-6603.
|
| [17] |
罗从伟,马军,江进,等.UV/H2O2降解2,4,6-三氯苯甲醚动力学及产物研究[J]. 中国环境科学, 2017,37(5):1831-1837.
|
| [18] |
Zhai H, Zhang X. Formation and decomposition of new and unknown polar brominated disinfection byproducts during chlorination[J]. Environ. Sci. Technol., 2011,45:2194-2201.
|
| [19] |
Pan Y, Zhang X. Four groups of new aromatic halogenated disinfection byproducts:Effect of bromide concentration on their formation and speciation in chlorinated drinking water[J]. Environ. Sci. Technol., 2013,47:1265-1273.
|
| [20] |
Xiao F, Zhang X, Zhai H, et al. New halogenated disinfection byproducts in swimming pool water and their permeability across skin[J]. Environ. Sci. Technol., 2012,46:7112-7119.
|
| [21] |
Ding G, Zhang X, Yang M, et al. Formation of new brominated disinfection byproducts during chlorination of saline sewage effluents[J]. Water Res., 2013,47:2710-2718.
|
| [22] |
Pang S Y, Jiang J, Gao Y, et al. Oxidation of flame retardant tetrabromobisphenol A by aqueous permanganate:Reaction kinetics, brominated products, and pathways[J]. Environ. Sci. Technol., 2014,48:615-623.
|
| [23] |
Dec J, Haider K, Bollag J M. Release of substituents from phenolic compounds during oxidative coupling reactions[J]. Chemosphere, 2003,52:549-556.
|
| [24] |
Poerschmann J, Trommler U. Pathways of advanced oxidation of phenol by Fenton's reagent-Identification of oxidative coupling intermediates by extractive acetylation[J]. J. Chromatogr. A, 2009,1216:5570-5579.
|
| [25] |
Castillo I, Pérez V, Monsalvo I, et al. Copper (Ⅱ) complexes of piperazine-derived tetradentate ligands and their chiral diazabicyclic analogues for catalytic phenol oxidative C-C coupling[J]. Inorg. Chem. Commun., 2013,38:1-4.
|
| [26] |
Gao R, Xu F, Li S, et al. Formation of bromophenoxy radicals from complete series reactions of bromophenols with H and OH radicals[J]. Chemosphere, 2013,92:382-390.
|
| [27] |
Lin K, Zhou S, Chen X, et al. Formation of hydroxylated polybrominated diphenyl ethers from laccase-catalyzed oxidation of bromophenols[J]. Chemosphere, 2015,138:806-813.
|
| [28] |
Huguet M, Deborde M, Papot S, et al. Oxidative decarboxylation of diclofenac by manganese oxide bed filter[J]. Water Res., 2013,47:5400-5408.
|
|
|
|
