製備具有酸性官能基之中孔洞矽材與生物質衍生碳材應用於有機催化反應

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吳聲維(Sheng-Wei Wu) 查詢紙本館藏

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化學學系

論文名稱

製備具有酸性官能基之中孔洞矽材與生物質衍生碳材應用於有機催化反應

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至系統瀏覽論文 (2029-6-30以後開放)

摘要(中)

本研究分為兩個部分。在第一部分研究中，利用中孔洞矽材具高比表面積、可調控的孔洞大小及孔洞體積等優點，透過直接合成法，將磺酸官能基修飾在一系列的三維中孔洞矽材表面。經過多種鑑定後，確認合成出S16SX(X = 10, 15, 20, 25, 30 )系列催化劑的結構與穩定性。此系列催化劑具有高比表面積、孔洞一致性和富有酸性位點，期望能應用於催化雙(三羥甲基)丙烷(Di-TMP)酯化反應。透過探討不同結構之中孔洞矽材、修飾上磺酸官能基的比例、不同催化劑量及不同丙烯酸與雙(三羥甲基)丙烷比例對於選擇性產生雙(三羥甲基)丙烷二丙烯酸酯(Di-TMPDA)的影響，得知最佳反應條件為以1.8 g S16S20當作催化劑，在起始物AA與Di-TMP莫耳比為2:1時進行反應。在溫度維持95℃，並持續除水的條件下，反應24小時後產生Di-TMPDA的比例約佔總產物的65%，並能減少雙(三羥甲基)丙烷三丙烯酸酯(Di-TMPTriA)與雙(三羥甲基)丙烷四丙烯酸酯(Di-TMPTetraA)的產生，因此，使用此催化劑S16S20是具有高催化活性並能選擇性產生特定產物
Di-TMPDA。
第二部分研究中，透過水熱及KOH化學活化的方式，在高溫鍛燒下將咖啡渣製備成具孔洞性質的生質碳材。活化後的生質碳材透過4-benzene-diazoniumsulfonate與次磷酸反應，修飾上磺酸官能基，並透過元素分析、XPS、TEM等鑑定，證明成功製備出酸性生質碳材（S-WCG）。將此催化劑用於間苯二酚與乙醯乙酸乙酯的佩希曼縮合反應（Pechmann condensation），合成7-羥基-4-甲基香豆素。研究中探討鍛燒溫度、KOH比例、催化劑用量和反應溫度對催化劑催化活性的影響。最後在鍛燒溫度800°C，KOH與碳源比例為2:1條件下，所製備出的酸性咖啡渣碳材（S-WCG-800-21）在溫度130°C反應20分鐘時，得到最高的香豆素產率88%。

摘要(英)

This study is divided into two parts. In the first part, taking advantage of mesoporous silica materials with high specific surface area, tunable pore size, and pore volume, sulfonic acid functional groups were directly synthesized on the surface of a series of three-dimensional mesoporous silica materials. Through SAXRD, BET, TEM, and XPS characterization, the structure and stability of the S16SX (X = 10, 15, 20, 25, 30) series catalysts were confirmed. This series of catalysts possesses high specific surface area, pore uniformity, and abundant acidic sites, and is expected to be applied in the catalytic Fischer esterification reaction of di(trimethylolpropane) (Di-TMP). By exploring the effects of different mesoporous silica structures, the ratio of sulfonic acid functional groups, different catalyst loading, and different ratios of acrylic acid to Di-TMP on the selective production of Di-TMPDA, it was found that the optimal reaction conditions were using 1.8 g of S16S20 as the catalyst with a starting material molar ratio of AA to Di-TMP of 2:1. Under the conditions of maintaining the temperature at 95°C and continuous water removal, after 24 hours of reaction, the proportion of Di-TMPDA in the total product was about 65%, and the production of Di-TMPTriA and Di-TMPTetraA was reduced. Therefore, the catalyst S16S20 exhibits high catalytic activity and can selectively produce the product Di-TMPDA.
In the second part, wasted coffee grounds were transformed into porous biochar materials through hydrothermal acidic hydrolysis and KOH chemical activation methods under high-temperature calcination. The activated biochar was functionalized with sulfonic acid groups by reacting with 4-benzene-diazoniumsulfonate and hypophosphorous acid. Elemental analysis, XPS, TEM, and other characterizations confirmed the successful preparation of acidic biochar (S-WCG). This catalyst was applied in the Pechmann condensation reaction of resorcinol with ethyl acetoacetate to synthesize 7-hydroxy-4-methylcoumarin. The study explored the effects of calcination temperature, KOH ratio, catalyst loading, and reaction temperature on the catalytic activity. Finally, under the conditions of a calcination temperature of 800°C and a KOH-to-carbon source ratio of 2:1, the acidic wasted coffee ground-derived biochar (S-WCG-800-21) achieved the highest coumarin yield of 88% at 130°C in 20 minutes.

關鍵字(中)

★ 異相催化劑
★ 中孔洞矽材
★ 酯化反應
★ 香豆素
★ 生物質衍生碳材

關鍵字(英)

論文目次

摘要 i
Abstract iii
謝誌 v
目錄 vii
圖目錄 xiv
表目錄 xx
第一章緒論 1
第壹部分具酸性官能基之中孔洞矽材催化雙(三羥甲基)丙烷酯化反應 1
1-1中孔洞矽材 (Mesoporous Silica Materials, MSMs) 1
1-1-1中孔洞矽材之簡介 1
1-1-2中孔洞矽材的定義 2
1-1-3中孔洞矽材的合成方式 4
1-1-4界面活性劑的種類 5
1-1-5微胞形成的方式與種類 8
1-1-6微胞與矽源的作用力 9
1-2具官能基化之中孔洞矽材 12
1-2-1中孔洞矽材表面修飾法 12
1-2-2具磺酸官能基之中孔洞矽材 15
1-3雙(三羥甲基)丙烷反應 19
1-3-1丙烯酸酯介紹 19
1-3-2雙(三羥甲基)丙烷酯化反應與文獻回顧 21
第貳部分具酸性官能基之生質碳材催化佩希曼縮合反應 24
1-4生物質碳材 24
1-4-1生物質碳材之簡介 24
1-4-2生質碳材活化方法 25
1-4-2.1 化學活化法(Chemical activation) 26
1-4-2.2 物理活化法(Physical activation) 27
1-4-2.3 自活化法(Self-activation) 28
1-4-2.4 模板法(Template method) 28
1-4-2.4 水熱法(Hydrothermal method) 29
1-4-3咖啡渣衍生生質碳材發展與應用 30
1-5佩西曼縮和反應（Pechmann condensation） 34
1-5-1香豆素介紹 34
1-5-2合成香豆素之發展 35
1-5-3佩西曼縮和反應文獻回顧 37
1-6研究目的與動機 40
第二章實驗部分 41
2-1實驗藥品 41
2-1-1第一部份使用之藥品 41
2-1-2第二部份所使用之藥品 43
2-2實驗步驟 44
第壹部分具酸性官能基之中孔洞矽材催化雙(三羥甲基)丙烷酯化反應 44
2-2-1合成具酸性官能基之S16SX 44
2-2-2合成具酸性官能基之LP-S16SX 45
2-2-3合成具酸性官能基之F12SX 45
2-2-4以硫酸溶液移除催化劑中模板劑 46
2-2-5催化雙(三羥甲基)丙烷為雙(三羥甲基)丙烷二丙烯酸酯實驗 46
2-2-6 S16S20催化雙(三羥甲基)丙烷重複使用實驗 47
第貳部分具酸性官能基之生質碳材催化佩希曼縮合反應 48
2-2-7 咖啡渣衍生碳材 48
2-2-8活化咖啡渣衍生碳材 48
2-2-9合成磺酸化前驅物4-benzenediazoniumsulfonate 49
2-2-10合成具磺酸官能基之咖啡渣生質碳材(S-WCG) 49
2-2-11以具磺酸官能基之咖啡渣生質碳材催化佩希曼縮和反應 50
2-2-12催化佩希曼縮和反應重複使用實驗 50
2-3 實驗儀器 51
2-3-1實驗合成所需之儀器 51
2-3-2實驗鑑定儀器 52
2-4鑑定儀器之原理 53
2-4-1同步輻射中心光束線 (NSRRC) 53
2-4-2氮氣吸附脫附儀 (ASAP) 55
2-4-3穿透式電子顯微鏡 (TEM) 59
2-4-4掃描式電子顯微鏡 (SEM) 61
2-4-6 X光電子能譜 (XPS) 62
2-4-7粉末X光繞射儀（PXRD） 63
2-4-8傅立葉紅外線吸收光譜儀（FTIR） 64
2-4-9核磁共振（NMR） 66
2-4-11元素分析儀 (EA) 69
2-4-12高效能液相層析儀 (HPLC) 70
2-4-14熱重分析儀 (TGA) 72
2-4-15拉曼光譜儀 (Raman) 73
第三章結果與討論 74
第壹部分具酸性官能基之中孔洞矽材催化雙(三羥甲基)丙烷酯化反應 74
3-1材料基本性質鑑定 74
3-1-1小角度X光繞射圖 (SAXRD) 74
3-1-2氮氣吸脫附鑑定 (BET) 77
3-1-3傅立葉轉換紅外線光譜圖 (FT-IR) 82
3-1-4元素分析 (EA) 83
3-1-5掃描式電子顯微鏡 (SEM) 85
3-1-6穿透式電子顯微鏡 (TEM) 88
3-1-7 X光電子能譜 (XPS) 91
3-1-8熱重分析 (TGA) 93
3-2催化雙(三羥甲基)丙烷為丙烯酸酯實驗 96
3-2-1 以不同孔洞性質之中孔洞矽材催化雙(三羥甲基)丙烷實驗 96
3-2-2固定S16SX系列催化劑磺酸官能基比例並探討孔洞性質對催化雙(三羥甲基)丙烷反應之影響 100
3-2-3不同催化劑量催化雙(三羥甲基)丙烷反應 103
3-2-4不同起始物比例催化雙(三羥甲基)丙烷反應 106
3-2-5 催化雙(三羥甲基)丙烷反應催化劑回收實驗 109
3-2-5.1 S16S20回收利用 109
3-2-5.2 S16S20 5th SAXRD 圖譜 112
3-2-5.3 S16S20 5th SEM 圖譜 113
3-2-5.4 S16S20 5th TEM 圖譜 114
3-2-5.5 S16S20 5th EA 115
3-2-5.6 S16S20 5th TGA 圖譜 116
第貳部分具酸性官能基之生質碳材催化佩希曼縮合反應 118
3-3 材料基本性質鑑定 118
3-3-1等溫氮氣吸脫附鑑定 (BET) 118
3-3-2掃描式電子顯微鏡 (SEM) 124
3-3-3穿透式電子顯微鏡 (TEM) 127
3-3-4大角度X光繞射圖 (WAXRD) 131
3-3-5拉曼光譜 (Raman) 132
3-3-6光電子能譜 (XPS) 134
3-3-7元素分析 (EA) 137
3-3-8熱重分析 (TGA) 138
3-4具酸性官能基之生質碳材催化佩希曼縮合反應實驗 140
3-4-1以不同孔洞性質之生質碳材催化佩希曼縮合反應實驗 140
3-4-1.1 不同活化劑製備之生質碳材催化佩希曼縮合反應 141
3-4-1.2 不同活化溫度及活化劑比例製備之生質碳材催化佩希曼縮合反應 142
3-4-2 不同反應物比例對生質碳材催化佩希曼縮合反應之影響 144
3-4-3 不同劑量之生質碳材對催化佩希曼縮合反應之影響 146
3-4-4不同反應溫度對生質碳材催化佩希曼縮合反應之影響 148
3-4-5中孔洞碳材與生質碳材對催化佩希曼縮合反應之比較 150
3-4-6 中孔洞碳材與生質碳材催化佩希曼縮合反應之回收測試 152
3-4-6.1 S-CMK9與S-WCG-800-21回收測試 152
3-4-6.2 S-CMK9與S-WCG-800-21 進行五次反應後元素分析 154
3-4-6.3 S-CMK9與S-WCG-800-21 進行五次反應後等溫氮氣吸脫附鑑定 155
3-4-9.4 S-WCG-800-21 進行五次反應後熱重分析鑑定 157
3-4-9.5 S-WCG-800-21 進行五次反應後TEM圖譜 158
3-4-9.6 S-WCG-800-21 進行五次反應後SEM圖譜 160
第四章結論 162
第五章參考資料 163

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指導教授

高憲明(Hsien-Ming Kao)

審核日期

2024-7-11

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