Transformation of Pyrene in Aqueous Chlorination in the Presence and Absence of Bromide Ion: Kinetics, Products, and Their Aryl Hydrocarbon Receptor-Mediated Activities

详细信息    查看全文

• 作者：Jianying Hu ; Xiaohui Jin ; Shoichi Kunikane ; Yoshiyasu Terao ; and Takako Aizawa
• 刊名：Environmental Science & Technology
• 出版年：2006
• 出版时间：January 15, 2006
• 年：2006
• 卷：40
• 期：2
• 页码：487 - 493
• 全文大小：265K
• 年卷期：v.40,no.2(January 15, 2006)
• ISSN：1520-5851

文摘

To assess the endocrine-disrupting activity stemmingfrom the presence of pyrene in drinking water, thekinetics of chlorination of pyrene was investigated atroom temperature, the products of its aqueous chlorinationwith and without bromide ion were identified, and theiraryl hydrocarbon receptor (AhR)-mediated activities weredetermined. It was found that the presence of bromideion greatly promoted the reaction rate of chlorination ofpyrene accompanied with the formation of brominatedproducts. While the main product was 1-Cl-pyrene withoutthe addition of bromide ion, di-Br-pyrene and 1-Br-pyrene became the main products in the presence ofbromide ion. GC-MS and NMR analysis identified threestructures of dibromopyrene in chlorination with the additionof bromide ion as 1,3-di-Br-pyrene, 1,6-di-Br-pyrene, and 1,8-di-Br-pyrene, and their molar ratio was determined tobe approximately 0.3:1:1. Finally, 1-Br-pyrene, 1,3-di-Br-pyrene, a mixture of 1,6-di-Br-pyrene and 1,8-di-Br-pyrene (di-Br-pyrene), 1-Cl-pyrene, and a mixture of 1,6-di-Cl-pyrene and 1,8-di-Cl-pyrene (di-Cl-pyrene) were fractionatedby HPLC, and their AhR-mediated activities were assessedby a yeast assay. It was found that the effective molarconcentrations (or mass concentration) showing half-maximaltranscriptional response, EC₅₀, for pyrene, 1-Br-pyrene, 1-Cl-pyrene, di-Cl-pyrene, and di-Br-pyrene were 5632 (1.14),3089 (0.86), 1942 (0.46), 597.2 (0.21), and 147.3 (0.04) nM (mg/L), respectively.