卤代醛/酮消毒副产物的生成潜能及其前驱物的结构特征
Formation potential of halogenated aldehydes and ketones disinfection by-products and structural characteristics of their precursors
-
摘要: 卤代醛和卤代酮类消毒副产物因具有"致畸、致癌、致突变"作用而倍受关注.对卤代醛/酮类消毒副产物控制及其前体物识别对饮用水安全保障具有重要意义.以大分子酸、疏水性酸、芳香族类亲水酸、亲水酸、糖类和氨基酸6类共14种常见有机物为对象,研究了不同有机物在氯化消毒过程中的卤代醛/酮生成潜力.结果表明,富里酸、柠檬酸、苹果酸、L-苏氨酸和L-天冬酰胺具有较高的卤代醛/酮生成势.有机物生成卤代醛/酮的过程包括2个阶段:前体物首先经氧化、脱羧等过程生成乙醛和丙酮,乙醛和丙酮被逐步氯代而生成氯代醛和氯代酮.实际水体的消毒实验表明,卤代醛/酮的生成势与水样中有机物的浓度无必然联系,但与水样中醇羟基及羰基官能团的含量呈正相关(R2=0.69—0.98).Abstract: Disinfection by-products of halogenated aldehydes and ketones have attracted great attention due to their teratogenic, carcinogenic and mutagenic effects. The prevention of halogenated aldehydes/ketones and the identification of their precursors are of great significance for the safety of drinking water. The formation potential of halogenated aldehydes/ketones in chlorination disinfection process was investigated with 14 natural organic substances in 6 categories, including macromoleculer acids, hydrophobic acids, aromatic hydrophilic acids, hydrophilic acids, saccharides and amino acids. The results showed that high halogenated aldehyde/ketone formation potential was observed when fulvic acid, citric acid, malic acid, L-threonine and L-asparagine were used as precursors. And the formation pathway of halogenated aldehydes/ketones from organic compounds included two stages:the precursors were first transformed into acetaldehyde and acetone through oxidation and decarboxylation, and then acetaldehyde and acetone were gradually chlorinated to produce chloroacetaldehydes and chloroacetones. The disinfection experiments in real water samples showed that the formation potential of halogenated aldehydes/ketones was not necessarily related to the concentration of organic compounds in the water samples, but positively related to the content of alcohol hydroxyl and carbonyl functional groups(R2=0.69-0.98).
-
-
[1] ROOK J J. Formation of haloforms during chlorination of natural water[J]. Acta Polytechnica, 2002, 42(2):234-243. [2] WEI J, YE B, WANG W, et al. Spatial and temporal evaluations of disinfection by-products in drinking water distribution systems in Beijing, China[J]. Science of the Total Environment, 2010, 408(20):4600-4606. [3] KOUDJONOU B, LEBEL GL, DABEKA L. Formation of halogenated acetaldehydes, and occurrence in Canadian drinking water[J]. Chemosphere, 2008, 72(6):875-881. [4] ZHANG L, XU L, ZENG Q, et al. Comparison of DNA damage in human-derived hepatoma line (HepG2) exposed to the fifteen drinking water disinfection byproducts using the single cell gel electrophoresis assay[J]. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 2012, 741(1-2):89-94. [5] DANIEL F B, DEANGELO A B, STOBER J A, et al. Hepatocarcinogenicity of chloral hydrate, 2-chloroacetaldehyde, and dichloroacetic acid in the male B6C3F1 mouse[J]. Fundamental & Applied Toxicology, 1992, 19(2):159-168. [6] US-EPA. National primary drinking water regulations:Long term 2 enhanced surface water treatment rule[J]. Federal Register, 2006, 71(3):654-702. [7] 董丽丽, 黄骏雄. 饮用水消毒副产物及其分析技术[J]. 化学进展, 2005, 1(2):172-180. DONG L L, HUANG J X. Status and analytical techniques of disinfection by-products in drinking water[J]. Progress in Chemistry, 2005, 1(2):172-180(in Chinese).
[8] BOUGEARD C. Haloacetic acids and other disinfection by-products in UK treated waters:Occurrence, formation and precursor investigation[D]. England:Cranfield University, 2009. [9] 江瑞, 黄璜, 吴乾元, 等. 再生水氯消毒过程中三氯丙酮生成特性及其前体物组成[J]. 给水排水, 2013, 39(s1):171-176. JIANG R, HUANG H, WU Q Y, et al. Formation and precursor composition of drichloroacetone in chlorine disinfection of reclaimed water[J]. Water & Wastewater Engineering, 2013, 39(s1):171-176(in Chinese).
[10] 蔡广强, 刘丽君, 张金松, 等. 水合三氯乙醛前体物的分子量分布和荧光特性[J]. 净水技术, 2014, 33(5):17-23. CAI G Q, LIU L J, ZHANG J S, et al. Molecular weight distribution and fluorescence characteristics of precursor of chloral hydrate[J].Water Purification Technology, 2014, 33(5):17-23(in Chinese).
[11] 张永吉, 周玲玲, 刘志生, 等. 水中天然有机物的分类特性及其卤代活性[J]. 环境科学, 2005, 26(1):104-107. ZHANG Y J, ZHOU L L, LIU Z S, et al. Characteristics and chlorination activity of natural organic matter in water[J]. Environmental Science, 2005, 26(1):104-107(in Chinese).
[12] MARHABA TF, VAN D. The variation of mass and disinfection by-product formation potential of dissolved organic matter fractions along a conventional surface water treatment plant[J]. Journal of Hazardous Materials, 2000, 74(3):133-147. [13] 王丽花, 周鸿, 张晓健, 等. 水源水中有机物特性及其氯化活性研究[J]. 环境科学学报, 2001, 21(5):573-576. WANG L H, ZHOU H, ZHANG X J, et al. Characteristics and chlorination activity of dissolved organic matter fractions in surface source water[J]. Acta Scientiae Circumstantiae, 2001, 21(5):573-576(in Chinese).
[14] BOND T, HENRIET O, GOSLAN EH, et al. Disinfection byproduct formation and fractionation behavior of natural organic matter surrogates[J]. Environmental Science & Technology, 2009, 43(15):5982-5989. [15] NIKOLAOU A D, LEKKAL T D, GOLFINOPOULOS S K, et al. Application of different analytical methods for determination of volatile chlorination by-products in drinking water[J]. Talanta, 2002, 56(4):717-726. [16] LIU Y, DUAN J, LI W, et al. Determination of volatile disinfection byproducts in water by gas chromatography-triple quadrupole mass spectrometry[J]. Analytical Letters, 2015, 48(1):188-203. [17] 刘立行. 仪器分析-第2版[M]. 北京:中国石化出版社, 2008:241-245. LIU L X. Instrumental analysis 2nd edition[M]. Beijing:China Petrochemical Press, 2008 :241-245(in Chinese).
[18] YANG X, SHANG C, WESTERHOFF P. Factors affecting formation of haloacetonitriles, haloketones, chloropicrin and cyanogen halides during chloramination[J]. Water Research, 2007, 41(6):1193-1200. [19] 陈丹霞, 黄富, 朱世翠, 等. 氯消毒过程中水中色氨酸产生THMs和HAAs的特征研究[J]. 中国环境科学, 2018, 38(11):4061-4067. CHEN D X, HUANG F, ZHU S C, et al. Generation characteristics of THMs and HAAs during tryptophan chlorination in aqueous system[J]. China Environmental Science, 2018, 38(11):4061-4067(in Chinese).
[20] NIKOLAOU A D, LEKKAS T D, KOSTOPOULOU M N, et al. Investigation of the behaviour of haloketones in water samples[J]. Chemosphere, 2001, 44(5):907-912. [21] HOW Z T, LINGE K L, BUSETTI F, et al. Chlorination of amino acids:Reaction pathways and reaction rates[J]. Environmental Science & Technology, 2017, 51(9):4870-4876. [22] 陈娇, 甘国娟, 伍欢, 等. 不同种类氨基酸在氯化后形成三卤甲烷和卤乙酸潜能特性[J]. 环境化学, 2018, 37(2):216-222. CHEN J, GAN G J, WU H, et al. Trihalomethanes and haloacetic acids formation upon chlorination of typical amino acids[J]. Environmental Chemistry, 2018, 37(2):216-222(in Chinese).
[23] FANG J, MA J, YANG X, et al. Formation of carbonaceous and nitrogenous disinfection by-products from the chlorination of Microcystis aeruginosa[J]. Water Research, 2010, 44(6):1934-1940. [24] 马圣存. 水中水合氯醛稳定性的影响因素及降解产物研究[D]. 哈尔滨:哈尔滨工业大学, 2017. MA S C. Toward better understanding of influencing factors and products of chloral hydrate in water[D]. Harbin:Harbin Institute of Technology, 2017(in Chinese). [25] CHUAN T, RUIPING L, HUIJUAN L, et al. Disinfection by-products formation and precursors transformation during chlorination and chloramination of highly-polluted source water:Significance of ammonia[J]. Water Research, 2013, 47(15):5901-5910. [26] WESTERHOFF P, MASH H. Dissolved organic nitrogen in drinking water supplies:A review[J]. Journal of Water Supply Research and Technology-Aqua, 2002, 51(8):415-448. [27] DOTSON A, WESTERHOFF P. Occurrence and removal of amino acids during drinking water treatment[J]. Journal-American Water Works Association, 2009, 101(9):101-115. [28] BROSILLON S, LEMASLE M, RENAULT E, et al. Analysis and occurrence of odorous disinfection by-products from chlorination of amino acids in three different drinking water treatment plants and corresponding distribution networks[J]. Chemosphere, 2009, 77(8):1035-1042. [29] 刘伟, 蔡广强, 卢小艳, 等. 典型南方水源氨基酸浓度变化与去除[J]. 环境科学, 2016, 37(10):3877-3883. LIU W, CAI G Q, LU X Y, et al. Concentration variation and removal of amino acids in typical drinking sources in the south of China[J]. Environmental Science, 2016, 37(10):3877-3883(in Chinese).
[30] 张健, 华伟, 张璐, 等. 水处理工艺过程中有机物分子量分布规律[J]. 水资源保护, 2012, 28(1):95-99. ZHANG J, HUA W, ZHANG L, et al. Molecular weight distribution of organic matter during water treatment process[J]. Water Resources Protection, 2012, 28(1):95-99(in Chinese).
[31] 蔡广强, 张金松, 刘丽君, 等. 常规处理工艺对有机物及三氯乙醛生成潜能的去除[J]. 中国给水排水, 2017, 33(19):46-50. CAI G Q, ZHANG J S, LIU L J, et al. Removal of organic matter and chloral hydrate formation potential by conventional treatment process[J]. China Water & Wastewater, 2017, 33(19):46-50(in Chinese).
[32] ZHONG X, CUI C, YU S. The determination and fate of disinfection by-products from ozonation-chlorination of fulvic acid[J]. Environmental Science & Pollution Research, 2017, 24(7):1-9. [33] TIAN C, LIU R, LIU H, et al. Disinfection by-products formation and precursors transformation during chlorination and chloramination of highly-polluted source water:significance of ammonia[J]. Water Research, 2013, 47(15):5901-5910. [34] 刘立超, 李静, 李征, 等. Cu2+对富里酸(FA)形态结构与其三卤甲烷生成能力的影响[J]. 环境化学, 2018, 37(2):249-254. LIU L C, LI J, LI Z, et al. Effect of Cu2+ on the structure of fulvic acid (FA) and its subsequent trihalomethane formation potential[J]. Environmental Chemistry, 2018, 37(2):249-254(in Chinese).
-

计量
- 文章访问数: 2719
- HTML全文浏览数: 2719
- PDF下载数: 107
- 施引文献: 0