Dickenson Eric R V, Summers R Scott, Croué Jean-Philippe, Gallard Hervé
Civil, Environmental and Architectural Engineering Department, University of Colorado, 428 UCB, Boulder, Colorado 80309, USA.
Environ Sci Technol. 2008 May 1;42(9):3226-33. doi: 10.1021/es0711866.
While it is known that resorcinol- and phenol-type aromatic structures within natural organic matter (NOM) react during drinking water chlorination to form trihalomethanes (THMs), limited studies have examined aliphatic-type structures as THM and haloacetic acid (HAA) precursors. A suite of aliphatic acid model compounds were chlorinated and brominated separately in controlled laboratory-scale batch experiments. Four and two beta-dicarbonyl acid compounds were found to be important precursors for the formation of THMs (chloroform and bromoform (71-91% mol/mol)), and dihaloacetic acids (DXAAs) (dichloroacetic acid and dibromoacetic acid (5-68% mol/mol)), respectively, after 24 h at pH 8. Based upon adsorbable organic halide formation, THMs and DXAAs, and to a lesser extent mono and trihaloacetic acids, were the majority (> 80%) of the byproducts produced for most of the aliphatic beta-dicarbonyl acid compounds. Aliphatic beta-diketone-acid-type and beta-keto-acid-type structures could be possible fast- and slow-reacting THM precursors, respectively, and aliphatic beta-keto-acid-type structures are possible slow-reacting DXAA precursors. Aliphatic beta-dicarbonyl acid moieties in natural organic matter, particularly in the hydrophilic fraction, could contribute to the significant formation of THMs and DXAAs observed after chlorination of natural waters.
虽然已知天然有机物（NOM）中的间苯二酚型和苯酚型芳香结构在饮用水氯化过程中会反应形成三卤甲烷（THMs），但仅有有限的研究考察了脂肪族型结构作为三卤甲烷和卤乙酸（HAA）前体的情况。在可控的实验室规模间歇实验中，分别对一组脂肪族酸模型化合物进行了氯化和溴化处理。在pH值为8的条件下反应24小时后，发现有四种和两种β - 二羰基酸化合物分别是形成三卤甲烷（氯仿和溴仿（71 - 91%摩尔/摩尔））以及二卤乙酸（DXAAs，二氯乙酸和二溴乙酸（5 - 68%摩尔/摩尔））的重要前体。基于可吸附有机卤化物的生成情况，对于大多数脂肪族β - 二羰基酸化合物而言，三卤甲烷和二卤乙酸是产生的副产物中的主要成分（> 80%），单卤乙酸和三卤乙酸的占比相对较小。脂肪族β - 二酮酸型和β - 酮酸型结构可能分别是反应较快和较慢的三卤甲烷前体，而脂肪族β - 酮酸型结构可能是反应较慢的二卤乙酸前体。天然有机物中的脂肪族β - 二羰基酸部分，尤其是在亲水性部分，可能是天然水氯化后观察到的大量三卤甲烷和二卤乙酸形成的原因。
