臺灣博碩士論文加值系統

工業、農業及養殖漁業等排放含有氨氮(NH4-N)的廢水會污染環境。共價有機框架(COF)因其高孔隙率和規則的通道結構而被做為廢水處理的新興候選材料。在這項研究中，通過席夫鹼縮合聚合反應成功合成了一種結構中含有羧基的新型COF化合物(COF-Daba)與無羧酸根結構之COF化合物(COF-Bda)用於比較其汙染物吸附之能力。FT-IR和固態 NMR 結果表明兩種COF已成功合成。XRD 圖表明 COF-Daba與COF-Bda結晶性較差，且與COF-Bda相比，COF-Daba因羧酸基結構而產生些微偏移。從 SEM 觀察到COF表面具有顆粒大小不一的粗糙結構證實其為無定形結構，而於TEM上並未發現有序的排列通道。BET分析顯示出兩種COF為Type II型吸附，表示為單一多層可逆吸附。TGA和DSC顯示出COF具有高強度之共價結構，使其展現出良好的熱穩定性。除此之外，經過吸附實驗後得知，具有羧酸根結構的COF-Daba吸附氨氮汙染物能力比無羧酸根之COF-Bda稍佳，並且COF-Daba還可以透過氫氧化鈉水溶液進行鹼化改質得到COF-Daba-Na，改質後的樣品具有最佳的氨氮吸附能力，COF-Daba-Na樣品之相關的吸附動力學與熱力學將進行深入之探討，另外本研究額外針對COF-Daba-Na樣品與含磷酸根離子水溶液進行吸附實驗做為比較。

Ammonium nitrogen (NH4-N) is a wastewater pollutant that often generated from
industry, agriculture and fisheries. Currently, covalent organic frameworks (COFs) are considered as an emerging candidate for wastewater treatment due to their high porosity and regular channel structure. In this study, a new type of COF compound (COF-Daba) with a carboxyl group in its structure (COF-Daba) and a comparing COF compound without a carboxylate structure (COF-Bda) were successfully synthesized by Schiff base condensation polymerization. Fourier transform infrared spectroscopy (FT-IR) and solid-state nuclear magnetic resonance (NMR) results indicated that two COFs were successfully synthesized. XRD patterns show that COF-Daba and COF-Bda are poor crystallinity, and the former one exhibits slightly shifted due to the presence of carboxylic acid group. From SEM image, it is observed that the surface of COF has a rough structure with different particle sizes. TEM results also shown similar size characteristic together with no orderly arrangement channel. BET analysis revealed that the two COFs were Type II adsorption, which represented a single multilayer reversible adsorption. Finally, the synthesized COFs were tested as adsorbents for ammonium chloride (NH4Cl) solution. The COF-Daba exhibited slightly higher ammonia nitrogen adsorption capacity compared to COF-Bda analogous. For achieving better adsorption capacity, COF-Daba was treated in NaOH to form the COONa containing COF, namely COF-Daba-Na. As a result , COF-Daba-Na compound exhibited the best adsorption capacity (19.26±1.79 mg g-1) under the concentration of ammonium chloride at 25 mg L-1. Furthermore, the adsorption kinetics and thermodynamics of COF-Daba-Na sample were investigated in detail. In addition, COF-Daba-Na sample carried out adsorption experiments on aqueous solutions containing phosphate ions for comparison.

摘要 i
Abstract iii
誌謝 v
目錄 vii
表目錄 x
圖目錄 xi
一、 緒論 1
二、 文獻回顧 3
2.1 氨氮特性及處理技術 3
2.1.1 氨氮汙染物之來源及特性 3
2.1.2 氨氮廢水處理技術 4
2.2 吸附 (Adsorption) 8
2.2.1 吸附定義 8
2.2.2 物理吸附 8
2.2.3 化學吸附 8
2.3 吸附劑(Adsorbent) 10
2.3.1吸附劑之種類 10
2.3.2無機吸附劑 10
2.3.3有機吸附劑 11
2.3.4有機/無機吸附劑 13
2.4 共價有機框架(Covalent organic framework, COF) 15
2.4.1 共價有機框架的定義 15
2.4.2 共價有機框架的發展 15
2.4.3 共價有機框架的製備 18
2.4.4 共價有機框架的應用 28
2.5 COF於吸附方面之應用 32
2.6 研究動機 38
三、 實驗方法 40
3.1 實驗架構 40
3.2 藥品與溶劑 42
3.3 儀器設備 43
3.4 實驗合成 44
3.4.1 觸媒Tetrakis(triphenylphosphine)palladium (Pd(PPh3)4)之合成[150] 44
3.4.2 1,2,4,5-Tetrakis-(4-formylphenyl)benzene (TPB-H)之合成 (Scheme 1)[81] 44
3.4.3 COF-Bda之合成 (Scheme 2) 45
3.4.4 COF-Daba之合成(Scheme 2) 45
3.5 檢測方法 47
3.5.1 表面官能基分析 47
3.5.2 表面型態分析 47
3.5.3 TGA之熱性質分析 47
3.5.4 DSC之熱性質分析 48
3.5.5 氮氣物理吸脫附分析 48
3.5.6 氨氮吸附試驗 48
3.5.7 磷酸鹽吸附試驗[153] 50
四、 結果與討論 52
4.1 COF-Bda與COF-Daba之結果與討論 52
4.1.1 TPB-H合成 52
4.1.2 COF合成 53
4.1.2 FT-IR鑑定分析 54
4.1.3 固態NMR鑑定分析 55
4.1.4 TGA熱性質分析 57
4.1.5 DSC熱性質分析 58
4.1.6 X光繞射分析儀(X-Ray Diffractometer, XRD) 59
4.1.7 表面形貌分析(SEM、TEM) 60
4.1.8 比表面積分析儀(BET) 61
4.1.9 吸附能力測試 64
4.1.10重複使用性測試 73
4.1.11 溶劑穩定性測試 74
4.1.12 吸附機制 75
4.1.13 磷酸鹽類之吸附 76
五、 結論 78
六、 參考文獻 79

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