製備具磺酸官能基之中孔洞矽材應用於有機催化反應

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范芳榕(Fang-Rong Fan) 查詢紙本館藏

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化學學系

論文名稱

製備具磺酸官能基之中孔洞矽材應用於有機催化反應
(Sulfonic Acid Functionalized Mesoporous Silica for the Catalytic Organic Reaction)

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至系統瀏覽論文 (2028-6-30以後開放)

摘要(中)

中孔洞矽材具有高比表面積、適當孔洞大小與熱穩定佳等等的優勢，因此本研究主要以中孔洞矽材做為底材，並修飾磺酸官能基，應用於酯化反應與佩希曼縮合反應 (Pechmann Condensation)中。
本研究分成兩個部份。第一部份，本研究利用直接合成法，將磺酸官能基修飾在中孔洞矽材 SBA-15 上。透過調整磺酸官能基與 TEOS 的比例，可合成出一系列 S15SX (X = 5, 10, 20, 25, 30)的樣品。經過 SAXRD, BET, XPS, TGA 等儀器鑑定確認材料結構的正確性與穩定性後，應用於三羥甲基丙烷 (TMP)酯化反應，並分別探討不同結構中孔洞矽材、磺酸官能基比例、不同丙烯酸與三羥甲基丙烷比例、不同溶劑比例、不同催化劑量等變因帶給反應的差異性。最後得知 AA 與 TMP 的莫爾比 2:1、環己烷與甲苯的體積比為 2:1 時，加入 1.8g S15S10 並施以 25 c.c/min 的空氣流速，能達到 50 %TMPDA 產量。而且，回收測試實驗中，當 S15S10 進行五次回收實驗後，仍具有 13%的 TMPDA 產量。
第二部份，本研究以擴孔的 SBA-16，LP-SBA-16 作為底材，並調整磺酸官能基比例合成一系列樣品:LP-S16SX (X= 5, 10, 20)，應用於佩希曼縮合反應中。研究中探討不同反應物比例、不同溫度、不同催化劑量、不同磺酸官能基比例以及不同結構的催化劑所帶來的影響。最後，當 Resorcinol 與 EAA 的莫爾比例為 1:1.5、反應時間 5 分鐘、溫度為 130 °C 時，可達到 TOF 值為 810 (h-1)的效果。在回收測試中，催化劑反應五次後仍具有 7%的產率。

摘要(英)

In this study, we adapted silica mesoporous materials loading with sulfonic acid group as catalyst due to its high specific surface area, proper pore size and high thermal stability properties. During the first part, we synthesized S15SX (X = 5, 10, 20, 25, 30) with TEOS as the silicon source, MPTMS as the sulfonica acid group precursor and P123 as the soft template. Due to the BET results, S15S10 possess 555cm2/g high specific surface area and 1.01nm optimal pore size. Those properties seem to favor the performance in esterification. Therefore, we applied it into Fischer esterification to produce TMPDA and explored the best experimental condition. Finally, we found that adding 1.8g S15S10 and 25 c.c/min air flow in the solution when molar ratio of AA:TMP is 2:1 and volume ratio of cyclohexane:toluene is 2:1 could reach 50% TMPDA GC Percent. Moreover, S15S10 still could produce 13% TMPDA GC Percent after 5 times recycling test.
In the second part, we employed LP-SBA-16 as the supporting materials and loaded with different amount of sulfonic acid group (LP-S16SX, X = 5, 10 ,20). Its high specific surface area, optimal pore size properties may be possibly favor the Pechmann condensation. Eventually, we found that LP-S16S5 exhibited high performance (810 (h-1)) in Pechmann condensation at 130 °C. Last but not least, LP- S16S5 still could get 7 % yield after 5 recycling tests.

關鍵字(中)

★ 中孔洞材料
★ 二氧化矽
★ 異相觸媒
★ 佩希曼縮合反應
★ 酯化反應
★ 光固化反應

關鍵字(英)

★ Silica Mesoporous materials
★ Heterogeneous catalyst
★ Pechmann condensation
★ Esterification
★ Photopolymerization
★ SiO2

論文目次

第一章緒論 ................................................................................................ 1
1-1 中孔洞矽材( Mesoporous Silica Materials, MSMs ) ................................. 1
1-1-1 中孔洞矽材簡介 ............................................................................. 1
1-1-2 中孔洞矽材的種類 ......................................................................... 2
1-1-3 中孔洞矽材合成方式 ..................................................................... 4
1-1-4 界面活性劑的種類 ......................................................................... 6
1-1-5 微胞形成方式與種類 ..................................................................... 9
1-1-6 微胞與矽源的作用力 ................................................................... 11
1-1-7 具官能基之中孔洞矽材 ............................................................... 14
1-2 光固化反應介紹 ...................................................................................... 16
1-2-1 光固化反應簡介 ........................................................................... 16
1-2-2 丙烯酸酯介紹 ............................................................................... 20
1-2-3 催化 1,1,1-三羥甲基丙烷反應催化劑種類介紹 ......................... 22
1-3 佩西曼縮合反應 (Pechmann Condensatoion)介紹 ................................. 24
1-3-1 香豆素介紹 ................................................................................... 24
1-3-2 合成香豆素之發展 ....................................................................... 26
1-3-3 佩希曼縮合反應的催化劑種類與發展 ........................................ 27
1-4 研究目的與動機 ............................................................................... 31
第二章實驗部分 ........................................................................................ 32
2-1 實驗藥品 ............................................................................................. 32
2-1-1 第一部分所使用藥品 ................................................................... 32
2-1-2 第二部分所使用藥品 ................................................................... 33
2-2 具磺酸官能基之中孔洞矽材催化佩希曼縮合反應 ....................... 34
2-2-1 合成具磺酸官能基之 SBA-15 (S15SX) ...................................... 34
2-2-2 合成具磺酸官能基之 SBA-16 (S16SX) ...................................... 35
2-2-3 合成具磺酸官能基之 KIT-6 (K6SX) ........................................... 35
2-2-4 合成具磺酸官能基之 LP-SBA-16 (LP-S61SX) ........................... 36
2-2-5 合成具磺酸官能基之 MCM-41 (M41SX) ................................... 36
2-2-6 合成具磺酸官能基之 FDU-12( F12SX ) ..................................... 37
2-2-7 以硫酸溶液移除中孔洞模板劑 ................................................... 37
2-2-8 催化三羥甲基丙烷為三羥甲基丙烷二丙烯酸酯實驗 ................ 37
2-2-9 催化三羥甲基丙烷反應重複使用實驗 ........................................ 38
2-2-10 以具磺酸官能基之中孔洞矽材催化佩希曼縮合反應 .............. 38
2-2-11 催化佩希曼縮合反應重複使用實驗 .......................................... 38
2-3 實驗儀器 ............................................................................................ 39
2-3-1 實驗合成儀器 ............................................................................... 39
2-3-2 實驗鑑定儀器 ............................................................................... 39
2-4 鑑定儀器原理 ................................................................................... 41
2-4-1 同步輻射中心光束線 (NSRRC) .................................................. 41
2-4-2 氮氣吸附脫附儀 (ASAP) ............................................................ 43
2-4-3 X 光電子能譜儀 (XPS) ................................................................ 48
2-4-4 穿透式電子顯微鏡 (TEM) .......................................................... 50
2-4-5 傅立葉紅外線吸收光譜儀 (FT-IR) ............................................. 51
2-4-6 核磁共振儀 (NMR) ..................................................................... 53
2-4-7 元素分析儀 (EA) ......................................................................... 56
2-4-8 氣相層析儀 (GC) ......................................................................... 57
2-4-9 掃描式電子顯微鏡 (SEM) .......................................................... 61
2-4-10 熱重分析儀 (TGA) .................................................................... 62
第三章結果與討論 ................................................................................ 63
3-1 具磺酸官能基中孔洞矽材鑑定......................................................... 63
3-1-1 小角度 X 光繞射圖 (SAXRD) .................................................... 63
3-1-2 氮氣吸脫附鑑定 (BET) ............................................................... 67
3-1-3 光電子能譜 (XPS) ....................................................................... 73
3-1-4 傅立葉轉換紅外線光譜圖 (FT-IR) ............................................. 76
3-1-5 固態核磁共振圖譜 (Solid State NMR) ....................................... 78
3-1-6 元素分析 (EA) ............................................................................. 84
3-1-7 熱重分析 (TGA) .......................................................................... 85
3-1-8 穿透式電子顯微鏡 (TEM) .......................................................... 88
3-1-9 掃描式電子顯微鏡 (SEM) .......................................................... 93
3-2 催化三羥甲基丙烷 (TMP)為三羥甲基丙烷二丙烯酸酯 (TMPDA)實驗
.................................................................................................................... 97
3-2-1 以不同結構中孔洞矽材催化三羥甲基丙烷反應 ........................ 97
3-2-2 以 S15SX 催化三羥甲基丙烷反應 ............................................ 102
3-2-3 固定磺酸官能基比例並探討孔洞大小對催化三羥甲基丙烷反應
之影響 ................................................................................................... 104
3-2-4 以不同催化劑量催化三羥甲基丙烷反應 .................................. 106
3-2-5 以不同起始物比例催化三羥甲基丙烷反應 .............................. 108
3-2-6 以不同溶劑比例催化三羥甲基丙烷反應 .................................. 110
3-2-7 反應中逐漸增加迴流溫度以催化三羥甲基丙烷反應 .............. 112
3-2-8 催化三羥甲基丙烷反應回收測試 ............................................. 114
3-3 催化三羥甲基丙烷 (TMP)為三羥甲基丙烷二丙烯酸酯 (TMPTA)實驗
................................................................................................................. 126
3-3-1 以不同催化劑量催化三羥甲基丙烷反應 .................................. 126
3-4 中孔洞矽材催化佩西曼縮合反應實驗 ............................................ 128
3-4-1 以不同結構中孔洞矽材催化佩西曼縮合反應實驗 .................. 128
3-4-2 以 LP-S16SX 催化佩西曼縮合反應實驗 .................................. 130
3-4-3 以 LP-S16SCY 催化佩西曼縮合反應實驗 ................................ 132
3-4-4 不同反應物比例對催化佩西曼縮合反應之影響 ...................... 134
3-4-5 不同催化劑量對催化佩西曼縮合反應之影響 .......................... 135
3-4-6 不同反應溫度對催化佩西曼縮合反應之影響 .......................... 137
3-4-7 不同衍生物對催化佩西曼縮合反應之影響 .............................. 138
3-4-8 催化佩西曼縮合反應回收測試 ................................................. 139
3-4-9 催化佩西曼縮合反應回收改善 ................................................. 148
第四章結論 ........................................................................................... 149
第五章參考資料 .................................................................................. 150

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指導教授

高憲明(Hsien-Ming Kao)

審核日期

2023-7-19

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