藥品及個人保健用品（Pharmaceuticals and personal care products）已多次於環境中檢測出，由於一般淨、污水處理設備無法將其有效去除，且可能轉變為致癌氧化消毒副產物而受到關注。氧化石墨烯（Graphene oxide，GO）由於高比表面積及官能基團，具有發展為新型水處理材料之潛力，然而其奈米尺度的特徵不易將其自水中移除，因此本研究以化學共沉降法將GO合成為帶有磁性可自水中移除之氧化石墨烯-四氧化三鐵（GO/Fe3O4），同時為探討藥品結構是否影響其進入GO/Fe3O4微孔，本研究從國內用量前二十大之藥品中，挑選三種不同結構之藥品，分別為雙氯芬酸（Diclofenac）、二甲雙胍（Metformin）與普萘洛爾（Propranolol）。本研究使用之GO材料為將Hummers法製程進行修正改良所製備，得出之GO含有較原方式更豐富之官能基，後續以不同方式製備GO/Fe3O4複合吸附材料，依據不同含鐵比例分類三種GO/Fe3O4複合材料，同時根據是否烘乾進一步再將此材料分為粉末與懸浮液兩種型態，在去離子水背景下對三種藥品進行批次吸附實驗，觀察GO/Fe3O4對三種藥品之吸附效果。從材料特性分析結果顯示，以不同方式製備之GO，後續製備出之GO/Fe3O4之GO含量範圍為15～40 %，比表面積範圍為302～407 m2/g，小於2 nm之微孔體積比例範圍為7～25 %，除了小於2 nm之孔隙體積比例，其餘材料特性皆高於過去研究之結果，顯示GO製備方式與個人手法影響後續GO/Fe3O4複合材料之特性。在等溫批次吸附實驗方面，在水質pH為6的情況下，以GO/Fe3O4複合材料粉末吸附水中三種藥品，以含鐵比例最低之S2.5吸附為普萘洛爾最佳，雙氯芬酸次之，最差者為二甲雙胍；隨著含鐵比例提高，二甲雙胍幾乎已不被吸附，雙氯芬酸之吸附效果則於高含鐵比例S72時優於普萘洛爾。二甲雙胍不具苯環之偏三維結構不易進入GO/Fe3O4微孔，含鐵比例較低時因微孔比例較高，導致普萘洛爾其具有Naphthalene雙苯環之偏二維結構較易進入GO/Fe3O4微孔；S72 GO/Fe3O4微孔比例較低，雙氯芬酸因其苯環結構上氯原子降低電子密度，較易與以碳為主要組成之GO/Fe3O4複合材料親合。以GO/Fe3O4複合材料懸浮液為吸附劑，在較低含鐵比例之S2.5與S18吸附效果為普萘洛爾最佳，二甲雙胍次之，最差者為雙氯芬酸；以高含鐵比例S72吸附效果最佳者為雙氯芬酸，最差者為二甲雙胍。推測原因為，低含鐵比例時懸浮液表面帶負電，與水質中性時帶負電荷之雙氯芬酸靜電相斥不易吸附，其他兩種藥品則因靜電相吸而吸附效果較好，普萘洛爾較偏二維之結構使其吸附效果最佳；因S72懸浮液之表面電荷趨近中性降低靜電作用力相斥之影響，雙氯芬酸因其接有氯原子之苯環降低電子密度，使其易與吸附劑親合反而吸附效果最佳，普萘洛爾則仍由於其較偏二維結構使吸附效果較二甲雙胍優。吸附動力實驗結果顯示假性二階動力反應方程式有較高相關性，實驗於去離子水背景進行，影響吸附反應速率因素除藥品濃度外，另一因素為GO/Fe3O4濃度，但實驗皆使用定量之GO/Fe3O4，故推測GO/Fe3O4表面官能基為影響吸附反應速率之另一原因。結果顯示以粉末吸附藥品約360分鐘後達到平衡，懸浮液則約60分鐘內達到平衡。pH影響方面，因藥品酸解離常數（Acid dissolution constant，pKa）高低影響藥品帶電狀態，進而影響GO/Fe3O4複合材料吸附量。GO/Fe3O4複合材料粉末因製備高溫烘乾使表面在水中帶電比例較低，若藥品處於不帶電狀態，因分子團聚而被中性之GO/Fe3O4粉末吸附捕集，使該藥品在表面呈中性時吸附量較帶電狀態下之吸附量高。GO/Fe3O4複合材料懸浮液表面帶負電荷為主，且表面負電荷隨pH值上升而增加，使得在中性環境下普遍表面帶有正電荷之二甲雙胍與普萘洛爾的吸附量可藉由靜電力吸引而提高吸附效果；但在中性環境下表面帶有負電荷之雙氯芬酸，其吸附量則因靜電相斥力增強而降低；當藥品表面若處於中性狀態，因靜電作用力消失而使懸浮液對二甲雙胍與普萘洛爾之吸附量與帶電狀態時有所降低，雙氯芬酸則有所增高。GO/Fe3O4複合材料雖可吸附藥品污染物，但對各藥品吸附效果有所差異，需考慮吸附目標污染物化學結構以及GO/Fe3O4複合材料型態，水質pH與藥品pKa亦為影響GO/Fe3O4複合材料吸附藥品效能之影響因子。

關鍵字：氧化石墨烯、四氧化三鐵、藥品、化學結構、等溫吸附線、吸附動力實驗

Pharmaceuticals and personal care products (PPCPs) have been detected in the environment repeatedly and are known to be difficultly removed in conventional wastewater treatment technologies. Graphene oxide (GO), due to its large surface area and modifiable functional groups, has the potential to be applied as a novel wastewater treatment technology. Considered the nano-size of GO material, the GO-iron oxide (GO/Fe3O4) composite with high adsorption capacity was synthesized by co-precipitation in this study, assisting in its quickly removal from the water phase with a magnetic force after treatment. The feasibility of this composite to remove pharmaceuticals in waters was investigated, with respect to the effects of the molecular structures of pharmaceuticals and preparation of the composite. The pharmaceuticals of interest included diclofenac, metformin, and propranolol. The Hummers method was employed to prepare the GO, following by synthesis to generate the GO/Fe3O4 suspension and particles with different iron contents. As to the physicochemical characteristics of the composites, the GO/Fe3O4 possessed a GO content from 15 % to 40 %, a surface area from 302 to 407 m2/g, fraction of the micro-pore with a diameter below 2 nm from 7 % to 25 %, showing a different result from those published. For the adsorption isotherms, at pH 6, the adsorption performance followed the order of propranolol > diclofenac > metformin by using the GO/Fe3O4 with low iron content (S2.5). Given its three-dimensional structure, metformin was less possible to be adsorped into the micro pores of the GO/Fe3O4. However, propranolol possesses naphthalene-like two-dimensional functional group, enhancing its adsorption by the micro-pores of the GO/Fe3O4. By increasing the iron content of the composites, the adsorption of diclofenac was better than that of propranolol. The chlorines on the benzene ring of diclofenac reducing the electronic density of diclofenac was one possible explanation for the enhanced adsorption. For the GO/Fe3O4 suspension as the adsorbent, the adsorption performance of propranolol was the best, whereas diclofenac was less adsorbed when the suspension possessed low iron contents. By increasing the iron content of the the adsorbent, the adsorption of diclofenac became the best, with the metformin adsorption was the worst. Both negative charges of diclofenac and GO/Fe3O4 suspension at low iron contents inhibited the diclofenac adsorption at a neutral pH, while the adsorption of the other two pharmaceuticals still occurred via electric attraction. When the iron content of the adsorbent increased (e.g.,S72), the surface charge of the suspension became neutral enhanced the diclofenac adsorption. The adsorptions of pharmaceuticals followed the pseudo-second-order equation, implying the effects of the pharmaceutical concentration and GO/Fe3O4 n the reaction rate. The adsorption onto particles reached equilibrium after 360 minutes when using the powder adsorbents, whereas the adsorption onto suspension reached equilibrium in 60 minutes. By changing the reaction pH, the surface charge of a pharmaceutical varied in accordance with its acid dissolution constant (pKa), varying the adsorption capacity. For both particle or suspension, the optimal adsorption occurred when the surface charges of the adsorbent and pharmaceutical were negative and positive, respectively. The findings of this study provided insights into the feasibility of using GO/Fe3O4 composites as a novel adsorbent to remove pharmaceuticals in waters, with respect to the effects of certain operation factors and preparation of the composite.

Key words : Graphene oxide; Iron oxide; Pharmaceutical; Molecular structure; Adsorption isotherm; Adsorption kinetics

摘要 i
Abstract iv
目錄 vi
圖目錄 ix
表目錄 xii
第一章 前言 1
1.1研究緣起 1
1.2研究目的 3
1.3研究貢獻與重要性 4
1.4研究架構 4
第二章 文獻回顧 6
2.1藥品及個人保健用品 6
2.1.1藥品及個人保健用品之來源與流佈 7
2.1.2藥品及個人保健用品之危害 8
2.1.3藥品及個人保健用品之去除 9
2.1.3.1薄膜去除PPCPs 9
2.1.3.2生物處理去除PPCPs 10
2.1.3.4高級氧化處理PPCPs 10
2.1.3.5吸附去除PPCPs 11
2.2石墨烯類材料 12
2.2.1氧化石墨烯 14
2.2.1.1氧化石墨烯製備 15
2.2.1.2還原態氧化石墨烯 16
2.2.1.3氧化石墨烯複合材料 17
2.2.2石墨烯類材料之其他吸附應用 18
2.2.2.1重金屬吸附 18
2.2.2.2染料吸附 19
2.2.2.3多環芳香烴吸附 21
2.2.2.4環境荷爾蒙吸附 21
2.2.2.5石墨烯類材料之吸附機制 22
2.2.3石墨烯類材料於環境中之行為 23
2.2.3.1氧化石墨烯之分散與聚合特性 23
2.2.3.2石墨烯類材料於環境中之降解現象 24
2.2.3.3石墨烯類材料於環境中之還原現象 25
第三章 實驗設備與方法 26
3.1實驗材料與設備 26
3.1.1材料與設備 26
3.2實驗方法 30
3.2.1 GO/Fe3O4合成方法 30
3.2.2去離子水背景之批次吸附實驗 30
3.3實驗數據分析 32
3.3.1等溫吸附曲線模式 32
3.3.2吸附動力方程式 33
3.4藥品濃度分析 33
3.5材料特性分析 34
3.5.1晶體結構 34
3.5.2 GO含量 35
3.5.3比表面積與孔隙體積 35
3.5.4表面結構 35
3.5.5懸浮液之界達電位 36
第四章 結果與討論 37
4.1材料特性分析 37
4.1.1晶體結構 37
4.1.2 GO含量 38
4.1.3比表面積與孔隙體積 40
4.1.4表面結構 43
4.1.5 GO/Fe3O4懸浮液之界達電位 45
4.2等溫吸附實驗 46
4.2.1 以不同製作方式之GO所合成之GO/Fe3O4吸附氯苯那敏之等溫吸附實驗 46
4.2.2 以GO/Fe3O4粉末吸附藥品之等溫吸附實驗 48
4.2.3以GO/Fe3O4懸浮液吸附藥品之等溫吸附實驗 51
4.3吸附動力實驗 54
4.3.1以GO/Fe3O4粉末吸附藥品之吸附動力實驗 54
4.3.2以GO/Fe3O4懸浮液吸附藥品之吸附動力實驗 59
4.4 pH影響吸附實驗 63
4.4.1 pH影響GO/Fe3O4粉末吸附藥品實驗結果 65
4.4.2 pH影響GO/Fe3O4懸浮液吸附藥品實驗結果 67
第五章 結論與建議 70
5.1結論 70
5.2建議 72
參考文獻 73

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