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The photodegradation of 1,3,6,8-tetrabromocarbazole in n-hexane and in solid-mediated aqueous system: Kinetics and transformation mechanisms
Chemical Engineering Journal ( IF 13.3 ) Pub Date : 2019-06-17 , DOI: 10.1016/j.cej.2019.121986
Xiaoxue Pan , Chenguang Li , Jing Chen , Jiaoqin Liu , Jiali Ge , Jiayi Yao , Siyuan Wang , Zunyao Wang , Ruijuan Qu , An Li

The kinetics and mechanisms of photochemical transformation of 1,3,6,8-tetrabromocarbazole (1368-BCZ) in n-hexane and pre-coated on solid particles in aqueous solution are investigated. Under simulated sunlight irradiation, 1368-BCZ dissolved in n-hexane rapidly photodegraded, obeying the pseudo first-order kinetics model. In the aqueous system, particles of seven different solids with coated 1368-BCZ were suspended during the reaction. The photodegradation kinetics of 1368-BCZ on three pure particles (silica gel, Al2O3, and Kaolin) fitted with the “double-logarithmic” model. At pH = 7.0 and T = 15 °C, 84% of 1368-BCZ with initial coating concentration of 100 μg g−1 silica gel disappeared in 1 h. The products and intermediates identified suggested that debromination and hydroxylation were the two main photochemical transformation pathways of 1368-BCZ in both n-hexane and aqueous systems. The proposed reaction pathways were supported by the results of quantum chemical calculation. However, several products including 1-monobromocarbazole (1-BCZ), 3-monobromocarbazole (3-BCZ), dibromocarbazole-1 (di-BCZ-1), and 3,6-dibromocarbazole (36-BCZ) were found during the reaction in n-hexane but not detected in the aqueous systems. This work provides useful information in the assessment of environmental fate of polyhalogenated carbazoles.



中文翻译:

1,3,6,8- tetrabromocarbazole在光降解ñ -己烷和在固体介导的含水系统:动力学和转化机构

动力学和在1,3,6,8- tetrabromocarbazole(1368-BCZ)的光化学转化的机制ñ -己烷和预涂覆在水溶液进行了研究的固体颗粒。下模拟太阳光的照射下,1368-BCZ溶于Ñ正己烷迅速光降解,服从准一级动力学模型。在水体系中,反应过程中悬浮了7种不同的固体颗粒,这些颗粒的涂层为1368-BCZ。1368-BCZ在装有“双对数”模型的三个纯颗粒(硅胶,Al 2 O 3和高岭土)上的光降解动力学。在pH = 7.0和T = 15°C时,84%的1368-BCZ的初始涂层浓度为100μgg -1硅胶在1小时内消失。的产物和中间体的鉴定表明,脱溴和羟基化分别在两个1368-BCZ的两个主光化学转化途径ñ -己烷和含水系统。所提出的反应途径得到了量子化学计算结果的支持。但是,在反应过程中发现了几种产物,包括1-一溴咔唑(1-BCZ),3-一溴咔唑(3-BCZ),二溴咔唑-1(di-BCZ-1)和3,6-二溴咔唑(36-BCZ)。在正-己烷中,但不是在含水体系中检测到。这项工作为评估多卤代咔唑的环境命运提供了有用的信息。

更新日期:2019-06-17
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