Department of Civil and Resource Engineering, Dalhousie University, Halifax, Nova Scotia, Canada.
Water Res. 2011 Jan;45(3):1414-22. doi: 10.1016/j.watres.2010.10.031. Epub 2010 Oct 31.
High global consumption rates have led to the occurrence of pharmaceutically active compounds (PhACs) in wastewater. The use of chlorine to disinfect wastewater prior to release into the environment may convert PhACs into uncharacterized chlorinated by-products. In this investigation, chlorination of a common pharmaceutical, the antihyperlipidemic agent gemfibrozil, was documented. Gemfibrozil (2,2-dimethyl-5-(2,5-dimethylphenoxy)pentanoic acid) was reacted with sodium hypochlorite and product formation was monitored by gas chromatography-mass spectrometry (GC-MS). The incorporation of one, two or three chlorine atoms into the aromatic region of gemfibrozil was demonstrated using negative-ion electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (ESI-MS/MS). Further analysis using (1)H nuclear magnetic resonance (NMR) spectroscopy identified the reaction products as 4'-ClGem (5-(4-chloro-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid) 4',6'-diClGem (5-(4,6-dichloro-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid), and 3',4',6'-triClGem (5-(3,4,6-trichloro-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid), products consistent with electrophilic aromatic substitution reactions. The rapid reaction of gemfibrozil with free chlorine at pH conditions relevant to water treatment indicates that a mixture of chlorinated gemfibrozils is likely to be found in wastewater disinfected with chlorine.
高全球消耗率导致了制药活性化合物（PhACs）在废水中的出现。在将废水排放到环境中之前，使用氯气进行消毒可能会将 PhACs 转化为未鉴定的氯化副产物。在这项研究中，记录了一种常见药物，即降脂药吉非贝齐的氯化作用。吉非贝齐（2,2-二甲基-5-（2,5-二甲基苯氧基）戊酸）与次氯酸钠反应，并通过气相色谱-质谱联用仪（GC-MS）监测产物形成。使用负离子电喷雾电离质谱（ESI-MS）和串联质谱（ESI-MS/MS）证明了吉非贝齐的芳环区域中一个、两个或三个氯原子的掺入。进一步使用（1）H 核磁共振（NMR）光谱分析确定反应产物为 4'-ClGem（5-（4-氯-2,5-二甲基苯氧基）-2,2-二甲基戊酸）、4',6'-diClGem（5-（4,6-二氯-2,5-二甲基苯氧基）-2,2-二甲基戊酸）和 3',4',6'-triClGem（5-（3,4,6-三氯-2,5-二甲基苯氧基）-2,2-二甲基戊酸），这些产物与亲电芳香取代反应一致。在与水处理相关的 pH 条件下，吉非贝齐与自由氯的快速反应表明，在经过氯气消毒的废水中可能会发现含有氯化吉非贝齐的混合物。
