亞硝胺（Nitrosamines）具有高致癌風險且陸續在世界各國多處飲用水及廢水處理系統中發現而受到關注，本研究利用吸附技術移除環境水體中之亞硝胺前驅物，期望藉此降低水中亞硝胺之生成潛勢（Formation Potential，FP），並挑選亞硝胺前驅物中擁有高莫爾轉換率（Molar Conversions）之氯苯那敏（Chlorpheniramine）作為目標污染物。氧化石墨烯（Graphene Oxide，GO）之高比表面積與親水性等特性，使其具有以吸附機制應用於淨水或廢污水處理程序之潛力，由於GO為奈米尺度之材料，因此本研究利用化學共沉降法製作出擁有高吸附能力及可利用磁鐵快速從水中移除之氧化石墨烯-四氧化三鐵（GO/Fe3O4）複合吸附材料。

本研究主要分為（1）去離子水背景之批次吸附實驗；（2）廢水廠放流水背景之批次吸附實驗；（3）廢水廠放流水之亞硝胺生成潛勢吸附去除實驗。去離子水背景之批次吸附實驗結果顯示，在水質pH為6情況下，氯苯那敏吸附效果為乾基GO/Fe3O4（經烘乾之粉末，後以乾基簡稱之）>濕基GO/Fe3O4（未經烘乾之溶液，後以濕基簡稱之）>活性碳，隨著吸附劑之鐵含量增加，乾基GO/Fe3O4表面可吸附氯苯那敏濃度也逐漸減少，推測為Fe3O4佔據GO表面之吸附位置所導致；而含鐵比例高低則對濕基GO/Fe3O4表面可吸附之氯苯那敏濃度並無顯著影響。乾基GO/Fe3O4因烘乾使水分去除造成GO層狀堆疊，並藉由Fe3O4在GO表面間支撐形成奈米尺寸之空隙，加強氯苯那敏被GO奈米孔隙捕集吸附之可能性。乾基GO/Fe3O4之BET比表面積及孔隙體積分析結果中顯示添加微量Fe3O4於GO表面有助於增加材料本身之微孔體積（< 2nm）及比表面積，並增加其對氯苯那敏之吸附能力，而總孔隙體積並非決定此材料對氯苯那敏可吸附量之關鍵因子。改變水質pH之批次實驗顯示，可根據污染物水中之解離狀態(pKa)及GO/Fe3O4吸附劑本身之表面電荷變化，來判斷有利吸附的最佳水質pH。反應速率部分則是濕基GO/Fe3O4較乾基快，約60分鐘內達到平衡，乾基GO/Fe3O4則需超過360分鐘，而含鐵比例多寡並無顯著影響乾、濕基GO/Fe3O4之反應速率。

廢水廠放流水背景之批次吸附實驗結果顯示，在水質pH為6情況下，氯苯那敏吸附效果為濕基GO/Fe3O4 >乾基GO/Fe3O4 >活性碳，其中乾、濕基GO/Fe3O4與活性碳之Freundlich模型參數n值與去離子水背景時相比，皆有顯著上升之趨勢，水中天然有機物（Natural Organic Matter，NOM）可能附著於本研究吸附劑之表面，進一步使吸附劑表面之異質性下降並增加其同質性；n值上升也代表吸附過程為有利性吸附，氯苯那敏濃度越高其吸附親和力有逐漸增強趨勢。與去離子水背景吸附結果相較之下，乾基吸附劑（乾基GO/Fe3O4或活性碳）對氯苯那敏之吸附效果皆呈現下降趨勢，實廠水樣中之溶解性有機物質（DOM）易與特定結構之PPCPs競爭吸附劑表面之吸附位置；而濕基GO/Fe3O4對氯苯那敏之吸附效果於廢水廠放流水背景下反而上升，可能與水中NOM之存在對吸附劑表面造成變化及水中離子強度增加有關。

廢水廠放流水經過乾基GO/Fe3O4（S2.5）之吸附程序後（pH為6），可有效移除亞硝胺類化合物FP（NDMA-FP移除29±12 %、NPIP-FP移除26±6 %、NMOR-FP移除46±1 %及NDBA-FP移除44 %）。於去離子水背景下添加氯苯那敏，經乾基GO/Fe3O4之吸附程序（pH為6）並測試其亞硝胺類化合物FP後，發現其FP呈上升趨勢，顯示添加乾基GO/Fe3O4不僅無法使亞硝胺類化合物FP下降，反而導致更多亞硝胺生成。廢水廠放流水中添加氯苯那敏，經乾基GO/Fe3O4（S2.5）之吸附程序（pH為6）並測試其亞硝胺類化合物FP後，發現此吸附劑對亞硝胺類化合物之FP同時存在吸附移除與生成增加之現象，即使添加高濃度之亞硝胺前驅物（氯苯那敏，14.6 μM），此吸附劑亦能有效降低亞硝胺類化合物之FP。

Nitrosamines are of concern because thery are highly carcinogenic and were frequently observed in water and wastewater treatment processes in many countries of the world. In this study, a wastewater treatment technology that reduced the formation potentials (FPs) of nitrosamines by removing potential nitrosamine precursors with high molar conversion rate via adsorption was investigated, with chlorpheniramine being selected as the target pollutants. Graphene oxide (GO), due to its large surface area and strong hydrophilicity, has the potential to remove contaminants by adsorption amongst water and wastewater treatment technoloiges. Considered the nano-size of GO material, the GO-iron oxide (GO/Fe3O4) composite with high adsorption capacity was synthesized by using the method of coprecipitation, as this material possesses the property of being quickly removed from water with magnetic force.

This study is divided into: (1) the batch adsorption experiments that removed chlorpheniramine in deionized water; (2) the batch adsorption experiments that removed chlorphenirame in real wastewater effluents; (3) the adsorption experiments that removed nitrosamine’s FP in wastewater effluents. In the 1st stage of the study, the removal efficiencies of chlorpheniramine by adsorption onto the surface of GO/Fe3O4 composite at pH 6 followed the order of: GO/Fe3O4 powder > GO/Fe3O4 suspension > activated carbon. With the increase of the iron content, the chlorpheniramine concentration onto the surface of GO/Fe3O4 powder was reduced because of limited adsorption sites, whereas the iron content of adsorbent did not significantly affect the removal of chlorpheniramine by the GO/Fe3O4 suspension. The stacking of GO layers became more obvious in the GO/Fe3O4 particle due to drying, forming nano-pore structures braced by Fe3O4 among GO layers to enhance the chlorpheniramine adsorption. The BET surface area, pore volume, pore size distribution measurements of GO/Fe3O4 particle supported the assumption that the enhanced chlorphenirame adsorption was associated with the increasing pore volume (diameter < 2 nm) and specific surface area. The total pore volume was not the critical factor to determine the adsorption capacity of chlorpheniramine onto GO/Fe3O4. By changing the reaction pH, the ionization states of chlorpheniramine and the surface charge of GO/Fe3O4 were both affected, affecting the optimal pH of effective adsorption. The chlorpheniramine adsorption onto the GO/Fe3O4 suspension (in 60 minutes) was overall more efficient than that of the GO/Fe3O4 particle (in 360 minutes), as the effect of changing the iron content of GO/Fe3O4 was negligible.

In the 2nd stage of the study, the chlorpheniramine removal in real effluents by adsorption at pH 6 followed the order of: GO/Fe3O4 suspension > GO/Fe3O4 particle > activated carbon. Compared to the results in the 1st stage of the study using deionized water, the n value in the Freundlich model fittings of both GO/Fe3O4 suspension and particle as well as activated carbon were significantly higher. Natural organic matter (NOM) could be attached onto the surface of GO/Fe3O4, declining the heterogeneity of the adsorbent surface. The rise of n value also represents adsorption process is favorable adsorption, meaning that excess chlorpheniramine adsorbed results in stronger adsorption affinity between chlorpheniramine and the GO/Fe3O4 surface. The chlorpheniramine adsorption by the GO/Fe3O4 particle and activated carbon in wastewater effluents were less efficient when compare to the results using deionized water as the background, atributalbe to the potential competition between dissolved organic matter (DOM) in wastewater and specific functional gourps of chlorpheniramine for adsorption sites on the GO/Fe3O4 surface. A different result was observed for the GO/Fe3O4 suspesion possibly due to the presence of NOM in wastewater decreasing the heterogeneity of the adsorbent sites and increasing the ionic strength.

In the 3rd stage of the experiments, the nitrosamine FPs in wastewater effluents were effectively treated by the GO/Fe3O4 particle at pH 6, as the FPs of N-Nitrosodimethylamine (NDMA), N-Nitrosopiperidine (NPIP), N-Nitrosomorpholine (NMOR) and N-Nitrosodi-n-butylamine (NDBA) were reduced by 29±12, 26±6, 46±1 and 44 %. By adding chlorpheniramine to deionized water in the GO/Fe3O4 particle experiment at pH 6, the nitrosamine FPs were increased suggesting that GO/Fe3O4 could possibly assist in nitrosamine formation. By adding chlorpheniramine to wastewater in the same experiment, the GO/Fe3O4 particle was found to simulataneously treat and result in the formation of nitrosamine. Even at a high chlorpheniramine concentration in wastewater, the nitrosamine FPs could still be efficiently treated by employing the GO/Fe3O4 particle as the adsorbent.

論文審定書 i
摘要 ii
Abstract iv
目錄 viii
圖目錄 xii
表目錄 xv
第一章 前言 1
1.1 研究緣起 1
1.2 研究目的 4
1.3 本研究之貢獻與重要性 5
第二章 文獻回顧 6
2.1 亞硝胺類化合物 6
2.1.1 亞硝胺之物理化學特性 7
2.1.2 亞硝胺之致癌風險與法規規範 9
2.2 亞硝胺之生成 11
2.2.1 消毒氧化（加氯）反應生成亞硝胺 11
2.2.2 消毒氧化（加氯胺）反應生成亞硝胺 12
2.2.3 消毒氧化（加臭氧）反應生成亞硝胺 14
2.2.4 活性碳表面反應生成亞硝胺 15
2.3 亞硝胺之前驅物 16
2.3.1 藥品與個人保健用品（PPCPs） 16
2.4 亞硝胺及其前驅物之去除 19
2.4.1 活性碳或生物活性碳吸附移除亞硝胺前驅物 19
2.4.2 薄膜過濾移除亞硝胺及其前驅物 21
2.4.3 紫外光（UV）去除亞硝胺 21
2.4.4 生物降解去除亞硝胺 22
2.5 實場廢水中之亞硝胺類化合物生成潛勢及濃度 23
2.6 石墨烯類衍生材料 24
2.6.1 石墨烯類衍生材料之製備方法 25
2.6.2 氧化石墨烯之表面改質 27
2.7 石墨烯類衍生材料於吸附技術上之應用 29
2.7.1 石墨烯類衍生材料吸附去除染料 29
2.7.2 石墨烯類衍生材料吸附去除PPCPs及環境賀爾蒙 30
2.7.3 石墨烯類衍生材料吸附去除多環芳香烴碳氫化合物 31
2.7.4 石墨烯類衍生材料吸附去除重金屬 31
2.8 石墨烯類衍生材料之環境宿命 36
2.8.1 石墨烯類衍生材料（GFNs）於環境水體中之吸附特性 36
2.8.2 氧化石墨烯（GO）於環境水體中之分散與聚合行為 37
2.8.3 石墨烯類衍生材料（GFNs）於環境水體中之轉化還原 38
2.8.4 石墨烯類衍生材料（GFNs）於環境水體中之降解 39
第三章 研究方法 41
3.1 研究架構 41
3.2 實驗材料與設備 43
3.2.1 材料與試劑 43
3.3 廢水廠放流水 50
3.3.1 採樣與保存 51
3.3.2 廢水廠放流水質分析 52
3.4 實驗方法與設計 53
3.4.1 先期亞硝胺去除實驗測試 53
3.4.2 GO/Fe3O4之合成 54
3.4.3 以去離子水為背景之批次吸附實驗 55
3.4.4 以實際廢水廠放流水為背景之批次吸附實驗 58
3.4.5 廢水廠放流水中亞硝胺生成潛勢之去除實驗 59
3.5 亞硝胺分析 61
3.5.1 固相萃取（前處理） 61
3.5.2 亞硝胺儀器分析 62
3.6 氯苯那敏分析 65
3.6.1 液相萃取之前處理步驟 65
3.6.2 氯苯那敏之儀器分析 66
3.7 品質保證與品質管理 68
3.8 吸附材料特性分析 69
3.8.1 GO含量分析 69
3.8.2 BET比表面積、孔徑分佈及孔隙體積分析 70
3.8.3 界達電位分析 70
3.8.4 晶體結構分析（X射線繞射分析儀） 70
3.8.5 表面結構分析（掃描式電子顯微鏡） 70
3.9 實驗數據分析 71
3.9.1 等溫吸附模式 71
3.9.2 吸附動力方程式 72
第四章 結果與討論 73
4.1 先期實驗測試 73
4.1.1 去離子水背景之二甲基亞硝胺（NDMA）批次吸附實驗 73
4.2 去離子水背景之氯苯那敏批次吸附實驗 75
4.2.1 等溫吸附實驗（去離子水背景） 75
4.2.2 含鐵比例影響吸附實驗 78
4.2.3 pH影響吸附實驗 80
4.2.4 吸附動力實驗 83
4.3 吸附材料與廢水廠放流水之特性分析 86
4.3.1 GO含量分析 86
4.3.2 BET比表面積及孔隙體積（包含孔徑分佈）分析 87
4.3.3 界達電位測量及吸附材料於水中之分散特性 90
4.3.4 表面晶體結構分析（X射線繞射分析） 91
4.3.5 掃描式電子顯微鏡分析 92
4.3.6 廢水廠放流水之特性分析 94
4.4 廢水廠放流水背景之氯苯那敏批次吸附實驗 95
4.4.1 空白吸附實驗 95
4.4.2 等溫吸附實驗（廢水廠放流水背景） 96
4.4.3 不同水質背景之等溫吸附線比較 98
4.5 廢水廠放流水之亞硝胺生成潛勢吸附去除實驗 102
4.5.1 廢水廠放流水之水質特性及亞硝胺類化合物生成潛勢分析 102
4.5.2 廢水廠放流水之亞硝胺生成潛勢去除效果 104
4.5.3 去離子水背景添加氯苯那敏之亞硝胺生成潛勢去除效果 106
4.5.4 廢水廠放流水背景添加氯苯那敏之亞硝胺生成潛勢去除效果 108
第五章 結論與建議 111
5.1 結論 111
5.2 建議 116
參考文獻 117

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