饮用水中微污染物质的快速检测及藻毒素降解动力学研究
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摘要
越来越多的研究结果证实饮用水中微污染物质诸如内分泌干扰物、消毒副产物、藻毒素等对人体有害，且这类物质在饮用水中通常以很低的浓度（μg/L甚至是ng/L级别）存在，因此开发快速、廉价和精确的检测方法对饮用水水质管理至关重要。本论文第一部分选择了对饮用水水质安全有较大威胁且常见的邻苯二甲酸酯（PAEs）、卤乙酸（HAAs）和微囊藻毒素-LR（MC-LR）作为研究对象，应用超高效液相色谱-电喷雾-串联四级杆质谱联用仪（UPLC-ESI-MS/MS），开发出快速检测这些物质方法。
世界卫生组织（WHO）将饮用水中MC-LR的建议值设为1μg/L（相当于人体摄入量为0.04μg/kg bw/day），但此设定值没有考虑低浓度、长期接触条件下对人体健康的影响。最新研究表明，当人类长期摄入低浓度MC-LR时（如0.04μg/kgbw/day），会出现不同症状的慢性疾病。本文第二部分研究了氯和高锰酸钾氧化降解低浓度MC-LR（初始浓度为1μg/L）的动力学特征，并对MC-LR在水处理过程中能够达到的最低限值进行了讨论。
本论文得到的主要成果有：
（1）随着塑料制品的大量使用，内分泌干扰物PAEs已广泛存在于各类环境中，对人类健康造成较大威胁。本研究首先使用UPLC-ESI-MS/MS梯度洗脱方式对邻苯二甲酸二乙酯（DEP）、邻苯二甲酸二正丁酯（DBP）、邻苯二甲酸丁基苄酯（BBP）和邻苯二甲酸二（2-乙基己基）酯（DEHP）进行了分离测定研究。研究发现，在分离过程中色谱图会出现“鬼峰”，干扰DEHP的准确定量。实验分析发现：在梯度洗脱的初始阶段（有机相比例较低时），流动相中含有的痕量DEHP会吸附在色谱柱上，这些物质随着有机相比例的升高而被快速压缩，最终进入检测器，就像进了样品一样，从而形成“鬼峰”。与梯度洗脱方式不同，尽管等度洗脱会减小DBP和BBP的分离度，但是能够避免出现“鬼峰”。本研究采用等度洗脱方式结合多通道检测（MRM）技术，开发出能够对PAEs精确定量的检测方法。本研究同时也讨论了真实样品检测中，基质效应对色谱分离及信号强度的影响。研究发现饮用水中的无机离子对目标物质的检测信号有很大影响，向实际样品中投加一定比例的甲醇能够提高质谱信号强度，从而能够缓解因基质效应引起的信号压缩现象。本研究开发的方法线性范围为0.5~50μg/L，样品无需富集处理检测限能够达到0.32~0.54μg/L，满足饮用水中痕量PAEs的检测需求。
（2）当使用氯对饮用水进行消毒处理时，除三卤甲烷（THMs）外，HAAs是第二大类常见的、毒性较大的消毒副产物。现有检测HAAs的方法大多具有样品预处理复杂、9种HAAs不能完全分离和检测限过高等缺点。本研究使用HSS T3色谱柱，在UPLC-ESI-MS/MS MRM模式下开发出一种能够实现9种HAAs完全分离、样品预处理简单、价格低廉且分离快速的检测方法，并且根据实验结果提出并讨论了HSS T3色谱柱分离离子型化合物的机理。研究同时也讨论了甲醇-水流动相体系的水相中加入0.125mM甲酸作为修饰剂分离小分子HAAs（如一卤乙酸、二卤乙酸）的作用和机理。样品无需进行富集处理的条件下，9种HAAs即可得到很低的检测限（0.06~0.16μg/L），建立标准曲线的线性范围为0.5~100μg/L（R2=0.9993~0.9997，n=6）。当使用开发的方法检测真实水样中HAAs时，样品中的无机离子导致HAAs分离度变差和信号减弱，进一步研究发现将样品pH值调至3.0或以下时能够基本消除基质效应。以地表水（总溶解固体（TDS）：145±3mg/L）和地下水（TDS：362±1mg/L）为研究对象，采用“标准添加法”进行方法验证表明，所开发的方法具有很高的精确度和回收率。
（3）MC-LR是自然水体中常见的、毒性极强的微囊藻毒素，因此加强MC-LR的监测对供水安全具有重要意义。本研究使用UPLC-ESI-MS/MS结合样品稀释法开发出检测饮用水中痕量MC-LR的方法，其检测限为0.04μg/L，定量限为0.1μg/L。同时，本研究探讨了水中离子强度、溶解态有机碳（DOC）和pH值对基质效应的影响规律。研究发现在超纯水背景条件下，加入的离子浓度越高，MC-LR检测信号压缩的越厉害；而信号强度随着样品pH值和低浓度DOC的增加而略有增强。实验还发现向样品中投加一定比例的甲醇（<30%，v/v）能够提高质谱信号强度。在本研究中，向自来水中投加4%甲醇（v/v）能够解决因基质效应产生的信号压缩问题。向三种含有不同离子浓度的空白自来水样品中添加0.2、1.0和10μg/L的MC-LR进行方法验证，结果表明样品的回收率为84.4~112.9%，完全满足水质分析的需求。
（4）氯和高锰酸钾是水处理中常用的消毒剂，探究其氧化降解微量有机物质的特征具有现实意义。本文研究了使用氯、高锰酸钾降解浓度为1μg/L的MC-LR至ng/L级别的动力学特征及其机理，结果表明与之前氧化降解高浓度MC-LR（初始浓度>20μg/L）的结果相似，超纯水中低浓度区间（1μg/L~2ng/L）的MC-LR降解依然符合准一级反应，然而当MC-LR浓度降至10ng/L以下时，反应动力学常数减小。另外，溶液中腐植酸浓度对两种氧化剂降解MC-LR的反应速率及最终浓度具有不同影响，这可能与这两种氧化剂降解MC-LR的机理不同有关。本研究结果表明使用氯或高锰酸钾依然能够将水中MC-LR浓度降低至10ng/L甚至更低，但是，在水处理过程中确定所需CT值之前，必须仔细考察水的溶液性质（特别是pH和腐植酸浓度）。
More and more studies show that some micro-organic substances such asendocrine disruptors, disinfection byproducts and microcystins in drinking water havecarcinogenic, teratogenic and mutagenic effect for human. The concentration of thesubstance usually stays in drinking water at μg/L or ng/L grade, thus, developingsensitively and fast detection methods have becaming more and more important inwater quality management. There are two parts in this thesis, in part1, simple and rapidmethods are developed using ultra performance liquid chromatography-electrosprayionization tandem mass spectrometry (UPLC-ESI-MS/MS) for determining phthalates(PAEs), haloacetic acids (HAAs) and microcystin-LR (MC-LR) in drinking water.
The World Health Organization (WHO) recommends a guideline value of MC-LR1μg/L; however, since the guideline value is based on the acute toxicity, it does not takeinto account the effects of possible long-term exposure to MC-LR at a lowconcentration. A new study indicated that there were kinds of chronic health effectswhen human intake the WHO value at long time. In order to safeguide the drinkingwater, in part2of this study investigated the reaction kinetic characteristics of MC-LRat low concentrations, and discussed the final concentration of MC-LR in drinkingwater treatment processes.
The main conclusions of this study are as follows.
（1）With a large number and diverse of commercial plastic products in use, PAEshave found their way ubiquitously into environmental compartments. In the analysis ofphthalates, specifically diethyl phthalate (DEP), dibutyl phthalate (DBP), butylbenzylphthalate (BBP), and diethylhexyl phthalate (DEHP) using UPLC-ESI-MS/MS,‘ghostpeaks’ appeared when a gradient liquid chromatography elution mode was employed. A systematic diagnostic analytical protocol was designed to show that the source of thepersistent ‘ghost peaks’, which jeopardized a quantitative analysis of these endocrinedisruptors was the mobile phase. A trace amount of DEHP in the mobile phase, eitherfrom ultrapure water or organic solvent, was responsible for the observed phenomenon.In contrast to gradient elution, isocratic chromatographic elution mode (ICEM) wasfound to be free of the problem at the expense of less effective separation of DBP andBBP. Thus, a detection method for analyzing the phthalates is proposed based on ICEMand the multiple reaction monitoring (MRM) modes with multi-channel detection in theUPLC-MS/MS. In the method development, tap water matrix effects were examinedand a solution for detection intensity suppression in the analysis of tap water sampleswas proposed. An addition of methanol into tap water samples could basically relievethe signal detection suppression by the real water matrix. This provides a detectionmethod of these trace environmental pollutants with a linear range between0.5to50μg/L and detection limits (LODs)(0.32-0.54μg/L) without need of samplepre-concentration. It is a simple, fast and sensitive method for determining PAEs indrinking water.
（2）After trihalomethanes (THMs), haloacetic acids (HAAs) are the second mostprevalent group of disinfection byproducts in chlorinated water. There are manydisadvantages in methods for detecting haloacetic acids (HAAs), for example, complexpreparation, large amounts of toxic organic reagents, high detection limits and nineHAAs can not be separated completely. In this paper, a simple and rapid detectionmethod for nine HAAs in water has been developed using UPLC-ESI-MS/MS inmultiple reactions monitoring (MRM) mode. A separation mechanism of the ionicanalytes using a reversed phase liquid chromatographic column (HSS T3) possessing ahydrophilic affinity has been proposed and discussed. Addition of a small amount offormic acid (FA) as a modifier for the methanol-water eluent was found to be critical forseparation of the analytes with smaller molecular size (i.e. the mono and di-haloaceticacids). Without the need of sample preconcentration, very low limits of detection (LODs)for the nine HAAs were achieved (0.06-0.16μg/L). The linear calibration rangeextended from0.5up to100μg/L (R2=0.9993-0.9997, n=6). The water matrix effect hasbeen examined, and seems to be related to the ions in real water samples. Interestingly, an adjustment of the pH of the tap water samples to an acidic value of3.0or belowbasically eliminated the matrix effect. The method has been tested using tap watersamples sourced from both surface water (total dissolved solid (TDS):145±3mg/L) andgroundwater (TDS:362±1mg/L) with high precision and recovery.
（3）MC-LR has been identified as the most common and most toxic ofmicrocystins in the natural water, and analysis of MC-LR in drinking water is veryimportant. A simple detection method using UPLC–ESI–MS–MS coupled with thesample dilution method for determining trace microcystin-LR (MC-LR) in drinkingwater is presented. The limit of detection (LOD) was0.04μg/L and the limit ofquantitation (LOQ) was0.1μg/L. Water matrix effects of ionic strength, dissolvedorganic carbon (DOC) and pH were examined. The results indicate that signal detectionintensity for MC-LR was significantly suppressed as the ionic strength increased fromultrapure water condition, whereas it increased slightly with solution pH and DOC atlow concentrations. However, addition of methanol (MeOH) into the sample was able tocounter the signal suppression effects. In this study, dilution of the tap water sample byadding4%MeOH (v/v) was observed to be adequate to compensate for the signalsuppression. The recoveries of the samples fortified with MC-LR (0.2,1, and10μg/L)for three different tap water samples ranged from84.4%to112.9%.
（4）Chlorine and permanganate are common used disinfectant in drinking watertreatment, therefore, study the degradation characterism of trace organic substances bychlorine and permanganate are very important. In response to the increasing concerns inthe literature about its human toxicity in drinking water at very low concentration levels,this study investigated the destruction of MC-LR down to concentrations of ng/L byboth chlorine and permanganate. The results showed that, similar to the previous studiesof MC-LR oxidation in the high concentration range (1g/L) the decomposition in thelow concentration range (1g/L-2ng/L) exhibits the features of pseudo-first-orderreaction with respect to each of the two oxidants in pure water solution conditions.However, when reaction proceeded down to a very low concentration (10ng/L) adifferent or a much smaller rate constant dictates the kinetics. In addition, in thepresence of humic acids (HA) in solution the reaction rates and the final concentrationremoval limit were affected presumably due to competition from reactions between the oxidant and HA. The behavior and the extent of such detrimental influence variedbetween the two oxidants. This creates some profound effects of the governance of anoxidant exposure CT over MC-LR degradation between the two oxidants, likely relatedto different reaction mechanisms of the two oxidants with MC-LR under the solutionconditions. This study indicates that chlorine and permanganate may be still effectivefor MC-LR decomposition down to a concentration of10ng/L or below; however theinfluence of solution chemistry (particularly pH for chlorine, and natural organic matterfor permanganate) must be carefully examined before a feasible CT is determined forthe control of this toxin in a water treatment system.
世界卫生组织（WHO）将饮用水中MC-LR的建议值设为1μg/L（相当于人体摄入量为0.04μg/kg bw/day），但此设定值没有考虑低浓度、长期接触条件下对人体健康的影响。最新研究表明，当人类长期摄入低浓度MC-LR时（如0.04μg/kgbw/day），会出现不同症状的慢性疾病。本文第二部分研究了氯和高锰酸钾氧化降解低浓度MC-LR（初始浓度为1μg/L）的动力学特征，并对MC-LR在水处理过程中能够达到的最低限值进行了讨论。
本论文得到的主要成果有：
（1）随着塑料制品的大量使用，内分泌干扰物PAEs已广泛存在于各类环境中，对人类健康造成较大威胁。本研究首先使用UPLC-ESI-MS/MS梯度洗脱方式对邻苯二甲酸二乙酯（DEP）、邻苯二甲酸二正丁酯（DBP）、邻苯二甲酸丁基苄酯（BBP）和邻苯二甲酸二（2-乙基己基）酯（DEHP）进行了分离测定研究。研究发现，在分离过程中色谱图会出现“鬼峰”，干扰DEHP的准确定量。实验分析发现：在梯度洗脱的初始阶段（有机相比例较低时），流动相中含有的痕量DEHP会吸附在色谱柱上，这些物质随着有机相比例的升高而被快速压缩，最终进入检测器，就像进了样品一样，从而形成“鬼峰”。与梯度洗脱方式不同，尽管等度洗脱会减小DBP和BBP的分离度，但是能够避免出现“鬼峰”。本研究采用等度洗脱方式结合多通道检测（MRM）技术，开发出能够对PAEs精确定量的检测方法。本研究同时也讨论了真实样品检测中，基质效应对色谱分离及信号强度的影响。研究发现饮用水中的无机离子对目标物质的检测信号有很大影响，向实际样品中投加一定比例的甲醇能够提高质谱信号强度，从而能够缓解因基质效应引起的信号压缩现象。本研究开发的方法线性范围为0.5~50μg/L，样品无需富集处理检测限能够达到0.32~0.54μg/L，满足饮用水中痕量PAEs的检测需求。
（2）当使用氯对饮用水进行消毒处理时，除三卤甲烷（THMs）外，HAAs是第二大类常见的、毒性较大的消毒副产物。现有检测HAAs的方法大多具有样品预处理复杂、9种HAAs不能完全分离和检测限过高等缺点。本研究使用HSS T3色谱柱，在UPLC-ESI-MS/MS MRM模式下开发出一种能够实现9种HAAs完全分离、样品预处理简单、价格低廉且分离快速的检测方法，并且根据实验结果提出并讨论了HSS T3色谱柱分离离子型化合物的机理。研究同时也讨论了甲醇-水流动相体系的水相中加入0.125mM甲酸作为修饰剂分离小分子HAAs（如一卤乙酸、二卤乙酸）的作用和机理。样品无需进行富集处理的条件下，9种HAAs即可得到很低的检测限（0.06~0.16μg/L），建立标准曲线的线性范围为0.5~100μg/L（R2=0.9993~0.9997，n=6）。当使用开发的方法检测真实水样中HAAs时，样品中的无机离子导致HAAs分离度变差和信号减弱，进一步研究发现将样品pH值调至3.0或以下时能够基本消除基质效应。以地表水（总溶解固体（TDS）：145±3mg/L）和地下水（TDS：362±1mg/L）为研究对象，采用“标准添加法”进行方法验证表明，所开发的方法具有很高的精确度和回收率。
（3）MC-LR是自然水体中常见的、毒性极强的微囊藻毒素，因此加强MC-LR的监测对供水安全具有重要意义。本研究使用UPLC-ESI-MS/MS结合样品稀释法开发出检测饮用水中痕量MC-LR的方法，其检测限为0.04μg/L，定量限为0.1μg/L。同时，本研究探讨了水中离子强度、溶解态有机碳（DOC）和pH值对基质效应的影响规律。研究发现在超纯水背景条件下，加入的离子浓度越高，MC-LR检测信号压缩的越厉害；而信号强度随着样品pH值和低浓度DOC的增加而略有增强。实验还发现向样品中投加一定比例的甲醇（<30%，v/v）能够提高质谱信号强度。在本研究中，向自来水中投加4%甲醇（v/v）能够解决因基质效应产生的信号压缩问题。向三种含有不同离子浓度的空白自来水样品中添加0.2、1.0和10μg/L的MC-LR进行方法验证，结果表明样品的回收率为84.4~112.9%，完全满足水质分析的需求。
（4）氯和高锰酸钾是水处理中常用的消毒剂，探究其氧化降解微量有机物质的特征具有现实意义。本文研究了使用氯、高锰酸钾降解浓度为1μg/L的MC-LR至ng/L级别的动力学特征及其机理，结果表明与之前氧化降解高浓度MC-LR（初始浓度>20μg/L）的结果相似，超纯水中低浓度区间（1μg/L~2ng/L）的MC-LR降解依然符合准一级反应，然而当MC-LR浓度降至10ng/L以下时，反应动力学常数减小。另外，溶液中腐植酸浓度对两种氧化剂降解MC-LR的反应速率及最终浓度具有不同影响，这可能与这两种氧化剂降解MC-LR的机理不同有关。本研究结果表明使用氯或高锰酸钾依然能够将水中MC-LR浓度降低至10ng/L甚至更低，但是，在水处理过程中确定所需CT值之前，必须仔细考察水的溶液性质（特别是pH和腐植酸浓度）。
More and more studies show that some micro-organic substances such asendocrine disruptors, disinfection byproducts and microcystins in drinking water havecarcinogenic, teratogenic and mutagenic effect for human. The concentration of thesubstance usually stays in drinking water at μg/L or ng/L grade, thus, developingsensitively and fast detection methods have becaming more and more important inwater quality management. There are two parts in this thesis, in part1, simple and rapidmethods are developed using ultra performance liquid chromatography-electrosprayionization tandem mass spectrometry (UPLC-ESI-MS/MS) for determining phthalates(PAEs), haloacetic acids (HAAs) and microcystin-LR (MC-LR) in drinking water.
The World Health Organization (WHO) recommends a guideline value of MC-LR1μg/L; however, since the guideline value is based on the acute toxicity, it does not takeinto account the effects of possible long-term exposure to MC-LR at a lowconcentration. A new study indicated that there were kinds of chronic health effectswhen human intake the WHO value at long time. In order to safeguide the drinkingwater, in part2of this study investigated the reaction kinetic characteristics of MC-LRat low concentrations, and discussed the final concentration of MC-LR in drinkingwater treatment processes.
The main conclusions of this study are as follows.
（1）With a large number and diverse of commercial plastic products in use, PAEshave found their way ubiquitously into environmental compartments. In the analysis ofphthalates, specifically diethyl phthalate (DEP), dibutyl phthalate (DBP), butylbenzylphthalate (BBP), and diethylhexyl phthalate (DEHP) using UPLC-ESI-MS/MS,‘ghostpeaks’ appeared when a gradient liquid chromatography elution mode was employed. A systematic diagnostic analytical protocol was designed to show that the source of thepersistent ‘ghost peaks’, which jeopardized a quantitative analysis of these endocrinedisruptors was the mobile phase. A trace amount of DEHP in the mobile phase, eitherfrom ultrapure water or organic solvent, was responsible for the observed phenomenon.In contrast to gradient elution, isocratic chromatographic elution mode (ICEM) wasfound to be free of the problem at the expense of less effective separation of DBP andBBP. Thus, a detection method for analyzing the phthalates is proposed based on ICEMand the multiple reaction monitoring (MRM) modes with multi-channel detection in theUPLC-MS/MS. In the method development, tap water matrix effects were examinedand a solution for detection intensity suppression in the analysis of tap water sampleswas proposed. An addition of methanol into tap water samples could basically relievethe signal detection suppression by the real water matrix. This provides a detectionmethod of these trace environmental pollutants with a linear range between0.5to50μg/L and detection limits (LODs)(0.32-0.54μg/L) without need of samplepre-concentration. It is a simple, fast and sensitive method for determining PAEs indrinking water.
（2）After trihalomethanes (THMs), haloacetic acids (HAAs) are the second mostprevalent group of disinfection byproducts in chlorinated water. There are manydisadvantages in methods for detecting haloacetic acids (HAAs), for example, complexpreparation, large amounts of toxic organic reagents, high detection limits and nineHAAs can not be separated completely. In this paper, a simple and rapid detectionmethod for nine HAAs in water has been developed using UPLC-ESI-MS/MS inmultiple reactions monitoring (MRM) mode. A separation mechanism of the ionicanalytes using a reversed phase liquid chromatographic column (HSS T3) possessing ahydrophilic affinity has been proposed and discussed. Addition of a small amount offormic acid (FA) as a modifier for the methanol-water eluent was found to be critical forseparation of the analytes with smaller molecular size (i.e. the mono and di-haloaceticacids). Without the need of sample preconcentration, very low limits of detection (LODs)for the nine HAAs were achieved (0.06-0.16μg/L). The linear calibration rangeextended from0.5up to100μg/L (R2=0.9993-0.9997, n=6). The water matrix effect hasbeen examined, and seems to be related to the ions in real water samples. Interestingly, an adjustment of the pH of the tap water samples to an acidic value of3.0or belowbasically eliminated the matrix effect. The method has been tested using tap watersamples sourced from both surface water (total dissolved solid (TDS):145±3mg/L) andgroundwater (TDS:362±1mg/L) with high precision and recovery.
（3）MC-LR has been identified as the most common and most toxic ofmicrocystins in the natural water, and analysis of MC-LR in drinking water is veryimportant. A simple detection method using UPLC–ESI–MS–MS coupled with thesample dilution method for determining trace microcystin-LR (MC-LR) in drinkingwater is presented. The limit of detection (LOD) was0.04μg/L and the limit ofquantitation (LOQ) was0.1μg/L. Water matrix effects of ionic strength, dissolvedorganic carbon (DOC) and pH were examined. The results indicate that signal detectionintensity for MC-LR was significantly suppressed as the ionic strength increased fromultrapure water condition, whereas it increased slightly with solution pH and DOC atlow concentrations. However, addition of methanol (MeOH) into the sample was able tocounter the signal suppression effects. In this study, dilution of the tap water sample byadding4%MeOH (v/v) was observed to be adequate to compensate for the signalsuppression. The recoveries of the samples fortified with MC-LR (0.2,1, and10μg/L)for three different tap water samples ranged from84.4%to112.9%.
（4）Chlorine and permanganate are common used disinfectant in drinking watertreatment, therefore, study the degradation characterism of trace organic substances bychlorine and permanganate are very important. In response to the increasing concerns inthe literature about its human toxicity in drinking water at very low concentration levels,this study investigated the destruction of MC-LR down to concentrations of ng/L byboth chlorine and permanganate. The results showed that, similar to the previous studiesof MC-LR oxidation in the high concentration range (1g/L) the decomposition in thelow concentration range (1g/L-2ng/L) exhibits the features of pseudo-first-orderreaction with respect to each of the two oxidants in pure water solution conditions.However, when reaction proceeded down to a very low concentration (10ng/L) adifferent or a much smaller rate constant dictates the kinetics. In addition, in thepresence of humic acids (HA) in solution the reaction rates and the final concentrationremoval limit were affected presumably due to competition from reactions between the oxidant and HA. The behavior and the extent of such detrimental influence variedbetween the two oxidants. This creates some profound effects of the governance of anoxidant exposure CT over MC-LR degradation between the two oxidants, likely relatedto different reaction mechanisms of the two oxidants with MC-LR under the solutionconditions. This study indicates that chlorine and permanganate may be still effectivefor MC-LR decomposition down to a concentration of10ng/L or below; however theinfluence of solution chemistry (particularly pH for chlorine, and natural organic matterfor permanganate) must be carefully examined before a feasible CT is determined forthe control of this toxin in a water treatment system.
引文
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