N-亞硝胺為含氮新興消毒副產物，在全球的飲用水和回收污水中常被檢出，其濃度多落在屬微量分析範疇的ng/L範圍，除了低濃度增加監測控制上的困難度外，更重要的是亞硝胺具有的高致癌性使其受到來自包含研究領域及管理單位的極大關注，在不同亞硝胺物種中，又以N-二甲基亞硝胺(N-Nitrosodimethylamine, NDMA)受到更為廣泛的研究與調查。目前已知的亞硝胺前驅物有二級胺、三級胺、殺蟲劑或除草劑如達有龍(Diuron)、含胺聚合物如PolyDADMAC (poly-diallyldimethylammoniumchloride)、藥品與個人保健用品如一種主要抑制胃酸分泌的藥物Ranitidine、Nizatidine等，但相關的前驅物及生成機制仍無法有效解釋飲用水和污水處理過程中觀察到的亞硝胺汙染情形，若源頭管制其生成前驅物有一定困難，清楚調查國內現有亞硝胺濃度分佈情形並了解淨水程序中亞硝胺的生成與宿命機制，調整甚至優化淨水處理技術以抑制或去除水體中亞硝胺濃度將是未來另一種亞硝胺危害管末處理的可能策略。
本研究調查六種目前在法規或相關研究領域受到注意的亞硝胺物種，其中包含NDMA、N-Nitrosodimethylamine (NMEA)、N-nitrosodiethylamine (NDEA)、N-nitroso-di-n-propylamine (NDPA)、N-nitrosodi-n-butylamine (NDBA)和N-nitrosopyrrolidine (NPYR)，本研究目的為以下四點(1)針對原水與特定處理單元之放流水進行亞硝胺採樣及定量分析；(2)量化六種亞硝胺在飲用水處理過程中的生成，同時探討氧化技術置於不同階段或與其他處理技術結合使用對亞硝胺生成或去除的可能影響 (3)利用模擬實驗了解選定之處理場其原水中可能的前驅物種類，探討未來原水條件改變含有其他額外的前驅物，對淨水程序所產生什麼影響，這些前驅物在飲用水中亞硝胺負面健康風險增量上所扮演之角色及其重要性；(4)除了從濃度的角度看亞硝胺問題外，也將濃度值轉換為風險進行評估，了解目前飲用水及未來若飲用水條件改變對用戶端所造成之健康危害。
水樣中的亞硝胺先經由固相萃取法(Solid-phase extraction, SPE)進行前處理，再使用氣相層析質譜儀(Gas Chromatography/Mass Spectrometry, GC/MS)及高壓液相層析串聯質譜儀(High Pressure Liquid Chromatography/Triple Quadruple Mass Spectrometry, HPLC/MS/MS)分別分析定量水體NDMA和其他亞硝胺濃度。本研究採樣試驗與討論分為三部份：
(一) 選定位於南台灣三座重要淨水場其原水及不同處理程序（特別針對前氧化處理技術）之放流水採樣並分析其中亞硝胺濃度，採樣於2013~2014年完成，調查結果主要探討目前原水中亞硝胺存在情形、不同處理技術（如前氧化、混凝、沉澱、與過濾、生物活性碳、及後消毒等）對水中六種亞硝胺濃度可能產生的生成或去除之影響，結果顯示原水中已受到亞硝胺汙染，從總亞硝胺濃度的角度，三座淨水處理流程中至配水端前皆可去除部分亞硝胺，但在放流端處理水仍可能存在一定濃度產生足夠風險，當單一前氧化技術為必要之處理策略，使用臭氧較有效減少水中亞硝胺生成比例；當氧化技術以兩階段方式應用（即前氧化後再搭配二次氧化），以加氯為主的處理流程對亞硝胺生成較不明顯；生物活性碳之效果隨不同亞硝胺物種而有所差異前，整體而言在所有技術當中，不論使用何種消毒劑，前氧化技術的使用皆大幅增加水中亞硝胺生成濃度，其中NDMA、NMEA、NDEA、NDBA普遍有生成的現象。
(二) 第二部分研究利用實廠原水於實驗室進行批次前氧化模擬試驗，實驗中添加三種已知NDMA前驅物，包含二甲胺、Diuron、與Ranitidine，實驗參數模擬實場操作條件，探討原水在未添加與添加額外前驅物狀態下，經由前加氯與前臭氧處理可能產生對其六種亞硝胺生成潛勢變化之影響。結果顯示原水本身含有前驅物，當水中沒有其他更強勢的前驅物，DMA可生成NDMA或甚至其他亞硝胺，但水中有時可能會其他更重要之前驅物，使DMA 之亞硝胺生成效果受到抑制，整體而言前驅物在環境水體中轉換成亞硝胺的效率低，顯示原水中其他共同存在的物種可能與氧化劑反應。
(三) 最後將在前兩階段研究中所得到結果，包含不同實場淨水處理程序中六種亞硝胺濃度分布情形及實驗室批次模擬實驗結果，從亞硝胺對下游水使用者可能產生的負面健康風險角度進行探討，計算其平均增量致癌風險與每年可能增加之發生率。結果顯示前氧化確實使部分亞硝胺濃度增加亦伴隨著部分亞硝胺的去除，亞硝胺濃度增加不一定會反應在風險上，當增加的亞硝胺為具有高致癌斜率因子的亞硝胺化合物如NDMA、NDEA，則會使前氧化風險大為增加，而致癌斜率因子較低的物種如NPYR若大幅去除，也會使整體致癌風險下降，以風險的角度而言除了濃度的變化以外，亞硝胺物種的存在也扮演著重要的腳色。
本研究建立亞硝胺管理策略對飲用水處理流程中之亞硝胺汙染進行控管，若以管末處理之角度，宜從前氧化程序之合理應用，評估是否使用前氧化、所使用的氧化劑，針對可能產生之衝擊進行改善，同時避免使用含胺類混凝劑、使用氯胺等處理技術；若以源頭管制為處理手段，宜避免原水污染同時確認不同亞硝胺物種在處理流程中之宿命，再進行其前驅物之管制。

N-Nitrosamines are a group of emerging nitrogenous disinfection byproducts (N-DBPs) that have been frequently detected in drinking water and recycled wastewater worldwide. The observed concentrations of nitrosamines in many drinking water treatment plants (DWTPs) and wastewater treatment plants (WWTPs) typically fall within the trace levels, increasing the difficulties of their detection and quantification. Nitrosamines have been of great concern in these years due to their potent carcinogenesis. Of these nitrosamine species, N-nitrosodimethylamine (NDMA) is the one of the most substantial concern in preceding researches. It has been reported that potential precursors of nitrosamines include secondary, tertiary, and quaternary amines, pesticides or herbicides (e.g., diuron), amine-based polymer (e.g., poly-diallyldimethylammoniumchloride, PolyDADMAC), pharmaceuticals and personal care products (PPCPs, e.g., a pharmaceutical named ranitidine or nizatidine that inhibiting gastric acid secretion). However, the presence of nitrosamines in DWTPs and WWTPs cannot be fully explained by the currently known precursors and associated formation mechanisms. While it is less likely to minimize the formation of nitrosamine by removing the possible precursors, fully investigating and understanding the formation and fate of nitrosamines through DWTPs and WWTPs may represent another important alternative to control the environmental hazards and human health risks posed by the presence of nitrosamines in treated water.
Six nitrosamines, including N-nitrosodimethylamine (NDMA), N-nitrosodimethylethylamine (NMEA), N-nitrosodiethylamine (NDEA), N-nitroso-di-n-propylamine (NDPA), N-nitrosodi-n-butylamine (NDBA), and N-nitrosopyrrolidine (NPYR) are of interest and investigated in this study. The objective of this study breaks into four parts: First, to collect and analyze the nitrosamines in raw water and effluents from various drinking water treatment processes; Second, to understand and quantify the formation of six nitrosamines in drinking water treatment processes and to discuss the associated effects of treatment technologies, notably the oxidation technologies, on the fate of nitrosamines in the DWTPs; Third, to conduct lab-scale batch experiments with addition of selected NDMA precursors to simulate preoxidation in the selected DWTPs, providing insights into the complex array of the relationships amongst potential precursors, oxidation technologies, and raw water characteristics; Fourth, to assess the carcinogenic risks posed by the concentrations of nitrosamines observed in the selected DWTPs and simulated preoxidation experiments during the previous three stages of this study, understanding the current and future possible health risks to downstream users with respect to the formation of nitrosamines in drinking water under different circumstances discussed in this study.
Nitrosamines in water were pretreated by solid-phase extraction (SPE), followed by analysis with gas chromatography coupled with mass spectrometry (GC/MS) or high pressure liquid chromatography coupled with triple quadruple mass spectrometry (HPLC/MS/MS). The experimental results observed in this study were categorized as following:
1. Source water and effluent from different treatment technologies, especially oxidation, from three major DWTPs in southern Taiwan were selected for sampling and analysis of nitrosamines. The sampling was conducted in 2013 and 2014 to investigate the fate of six nitrosamines among different technologies including preoxidation, coagulation, sedimentation, filtration, biological activated carbon (BAC) and post-disinfection. In the results, the presence of nitrosamines was observed in the source water. Nitrosamines were limitedly treated through all three DWTPs. While preoxidation is the important process to enhance the formation of nitrosamines, the use of ozone for preoxidation may reduce the formation of nitrosamines in water. However, different strategies such as using chorine may be more applicable to minimize the reactions producing nitrosamines if multiple oxidation processes were employed through the drinking water treatment processes. The effect of BAC varied with different nitrosamines. NDMA, NMEA, NDEA and NDBA represent the more important species to be considered in DWTPs selected in this study.
2. The lab-scale batch experiments using source water from the DWTPs of interest in this study were conducted, with dimethylamine (DMA), diuron, and ranitidine, three known and commonly used NDMA model precursors, being added to simulate the pre-chlorination and pre-ozonation in conventional DWTPs. It was shown in the results that other unknown precursors existed in the source water. More importantly, the effects of supplying these precursors during simulated preoxidation varied with different oxidation technologies and the extents of nitrosamine formation were less than expected. It appeared that the matrix amongst nitrosamine precursors, oxidation technologies, and source water characteristics were complicated and simultaneously determine the formation of six nitrosamines during preoxidation.
3. Finally, the concentrations of six nitrosamines observed in different circumstances in the first two stages of this study, including different drinking water treatment processes and lab-scale batch simulation experiments, were applied to calculate the corresponding human health risks to downstream users by ingestion of drinking water and were discussed in terms of the average incremental cancer risk and annual increasing incidence. In the results, the conclusions drawn from the cancer risk assessment were slightly different from those when the concentrations of nitrosamines formed or reduced were of concern. Preoxidation seemed to decrease the cancer risks posed by nitrosamines in water under certain circumstances, whereas the concentrations of most nitrosamines were increased during the processes. Different carcinogenicities among nitrosamine species was the possible explanation. Even though several nitrosamines were present or formed after preoxidation, the excess risks posed by the presence of these carcinogens may be limited as long as the nitrosamines with potent carcinogenicities (e.g., higher cancer slope factors) were treated or replaced by those less potent species.
As reducing and treating the presence of potential precursors in source water may represent another important but difficult approach to control the contaminations of drinking water with respect to the existence of carcinogenic nitrosamines, the focuses of this study were to investigate the formation of nitrosamines through various treatment technologies in three major DWTPs and to discuss the relationships amongst nitrosamine precursors, preoxidation technologies, and source water characteristics by conducting the simulated preoxidation experiments. The results of this study presented a comprehensive understanding regarding the current pollutions of nitrosamines in source water, associated fate through conventional DWTPs in southern Taiwan, importance of optimizing the preoxidation technologies to minimize the formation of nitrosamines in water and more importantly, possible human health risks posed by the presence of nitrosamines in treated water. These findings are expected to provide substantial information to develop appropriate management strategies, which may effectively control the environmental hazards and public health risks by these emerging oxidation/disinfection byproducts in the future.

論文審定書 i
致 謝 iii
摘 要 v
Abstract ix
目 錄 xiii
圖目錄 xvii
表目錄 xxi
第一章 前言 1
1.1 研究緣起 1
1.2 研究目的 4
1.3 研究問題 5
1.4 本研究之貢獻與重要性 6
第二章 文獻回顧 7
2.1 亞硝胺介紹 7
2.1.1 物理化學特性 8
2.1.2 危害性與法規規範 10
2.1.3 亞硝胺分析方法 11
2.2 亞硝胺的生成 12
2.2.1 氯化(Chlorination)生成亞硝胺 13
2.2.2 氯胺化(chloramination)生成亞硝胺 14
2.2.3 臭氧(Ozone)生成亞硝胺 19
2.2.4 活性碳(Activated Carbon, AC) 21
2.2.5 溴化物(Bromide)催化反應 22
2.3 亞硝胺的前驅物 23
2.3.1 二級胺(Secondary amines)、三級胺(Tertiary amines)、四級胺(Quaternary amines) 23
2.3.2 尿素系除草劑 (phenylurea herbicide) 29
2.3.3 藥品與個人保健用品(PPCPs) 32
2.4 亞硝胺與其前驅物的去除 38
2.4.1 混凝 38
2.4.2 避免氯胺的使用 38
2.4.3 活性碳(AC)或生物活性碳(BAC)吸附亞硝胺前驅物 39
2.4.4 紫外光(Ultraviolet, UV) 39
2.4.5 生物降解 40
2.4.6 薄膜 40
2.4.7 光催化 (Photocatalysis) 42
2.5 淨水場與環境中亞硝胺濃度 43
2.5.1 國外淨水場與環境中亞硝胺濃度 43
2.5.2 國內淨水 廠與環境中亞硝胺濃度 49
2.5.3 配水管線中亞硝胺濃度 49
第三章 研究方法 51
3.1 研究基本架構 51
3.2 場址選定與說明 53
3.3 實驗方法與設計 58
3.3.1 採樣與保存 59
3.3.2 亞硝胺濃度檢測 59
3.3.3 前氧化模擬實驗 61
3.3.3.1. 加氯實驗 62
3.3.3.2. 臭氧實驗 64
3.4 亞硝胺分析 67
3.4.1 前處理─固相萃取 67
3.4.2 儀器分析 70
3.4.3 品質保證與品質管理 73
3.5 資料分析 74
3.5.1 統計分析 74
3.5.2 亞硝胺暴露量評估(Exposure assessment) 77
3.5.3 亞硝胺致癌風險 79
第四章 結果與討論 83
4.1 各淨水場處理程序之總亞硝胺濃度變化分析 83
4.1.1 原水與放流端處理水中總亞硝胺濃度變化 83
4.1.2 不同淨水場其處理程序間之總亞硝胺濃度變化 86
4.2 不同處理技術對淨水程序中六種亞硝胺濃度變化之影響 89
4.2.1 不同前氧化處理技術 89
4.2.2 混凝、沉澱、過濾後接不同氧化程序 92
4.2.3 後加氯前接混凝、沉澱、過濾或生物活性碳 95
4.2.4 淨水場完整處理流程對六種亞硝胺之處理 97
4.3 亞硝胺濃度分佈之相關性分析 99
4.3.1 不同淨水場原水間相關性分析 99
4.3.2 不同採樣時間原水之相關性分析 101
4.3.3 不同處理流程間相關性分析 101
4.4 實驗室前氧化模擬試驗之亞硝胺生成 106
4.4.1 實場與模擬前氧化實驗結果間之差異 107
4.4.2 原水添加前驅物模擬試驗 108
4.4.3 不同採樣時期原水添加DMA模擬前氧化實驗之亞硝胺生成 111
4.4.4 不同氧化方式對DMA、Ranitidine及Diuron生成亞硝胺的影響 114
4.5 健康風險評估 117
4.5.1 不同淨水場其處理程序間亞硝胺致癌風險變化 117
4.5.2 模擬前氧化試驗中生成的亞硝胺其對應之致癌風險 124
第五章 結論與建議 131
5.1 結論 131
5.2 建議 134
參考文獻 137
附 錄 149
附錄A、 縮寫 149
個人簡歷 153

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