水环境中四溴双酚A(TBBPA)的非生物甲基化与甲基碘的生成

Abiotic Methylation of Tetrabromobisphenol A (TBBPA) with the Occurrence of Methyl Iodide in Aqueous Environments.

作者信息

Hou Xingwang, Kong Wenqian, Wang Xiaoyun, Liu Yanwei, Chen Weifang, Liu Jiyan, Schnoor Jerald L, Jiang Guibin

机构信息

State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, P.O. Box 2871, Beijing 100085, China.

College of Resources and Environment, University of Chinese Academy of Sciences, Beijing 100049, China.

出版信息

Environ Sci Technol Lett. 2019 Sep 10;6(9):558-564. doi: 10.1021/acs.estlett.9b00445. Epub 2019 Aug 5.

Abstract

Tetrabromobisphenol A (TBBPA) is the most widely used brominated flame retardant in the world. Its biotic methylation products, tetrabromobisphenol A mono- and dimethyl ether (TBBPA MME and TBBPA DME, respectively), are frequently detected in the environment, but the importance of abiotic methylation reactions of TBBPA in the environment is not known. In this study, the methylation of TBBPA mediated by methyl iodide (CHI), a ubiquitous compound in aqueous environments, was investigated in simulated waters in the laboratory. It was found that abiotic methylation occurred under both light and dark conditions and was strongly affected by the pH, temperature, and natural organic matter concentration of the water. Abiotic methylation was further verified in natural river water, and the yield of TBBPA MME mediated abiotically by CHI was much greater than that of biotic methylation. According to our calculations and by comparison of the activation energies ( ) for the abiotic methylation of TBBPA and the other four typical phenolic contaminants and/or metabolites (bisphenol A, triclosan, 5-OH-BDE-47, and 4'-OH-CB-61) mediated by CHI, those phenolic compounds all show great methylation potentials. The results indicate a new abiotic pathway for generating TBBPA MME and TBBPA DME from TBBPA, and they also confirm the potentials for abiotic methylation of other phenolic contaminants in aqueous environments.

摘要

四溴双酚A(TBBPA)是世界上使用最广泛的溴化阻燃剂。其生物甲基化产物,即四溴双酚A单甲醚和二甲醚(分别为TBBPA MME和TBBPA DME),在环境中经常被检测到,但TBBPA在环境中的非生物甲基化反应的重要性尚不清楚。在本研究中,在实验室模拟水中研究了由水环境中普遍存在的化合物碘甲烷(CHI)介导的TBBPA甲基化。结果发现,非生物甲基化在光照和黑暗条件下均会发生,并且受到水的pH值、温度和天然有机物浓度的强烈影响。在天然河水中进一步验证了非生物甲基化,由CHI非生物介导的TBBPA MME的产量远高于生物甲基化的产量。根据我们的计算,并通过比较CHI介导的TBBPA以及其他四种典型酚类污染物和/或代谢物(双酚A、三氯生、5-OH-BDE-47和4'-OH-CB-61)非生物甲基化的活化能,这些酚类化合物都显示出很大的甲基化潜力。结果表明了一种由TBBPA生成TBBPA MME和TBBPA DME的新的非生物途径,同时也证实了水环境中其他酚类污染物非生物甲基化的潜力。

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