製備酸性官能基之中孔洞矽材與奈米釕金屬中孔洞材料催化油酸酯化及硼烷氨水解脫氫之應用

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劉品邑(Pin-Yi Liu) 查詢紙本館藏

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論文名稱

製備酸性官能基之中孔洞矽材與奈米釕金屬中孔洞材料催化油酸酯化及硼烷氨水解脫氫之應用

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至系統瀏覽論文 (2028-6-30以後開放)

摘要(中)

本篇論文研究分為兩部分。第一部分研究中，使用一鍋合成法，合成出具有磺酸官能基修飾的中孔洞矽材 K6SX 系列之酸性催化劑。透過粉末 X 光繞射儀、N2 吸脫附曲線、掃描式電子顯微鏡等儀器對催化劑進行鑑定，此系列催化劑因具有高比表面積、大孔洞體積和附有酸性位點等優點，將其用於催化油酸為油酸甲酯。經過一系列的實驗優化，最後以K6S10作為此實驗的最佳催化劑，產物油酸甲酯 (MO) 在油酸/甲醇=1:20，反應時間 4 小時，其轉換率達 98%，產率為 91%。此研究中，磺酸官能基修飾的中孔洞矽材表現出高催化活性及應用性。
第二部分研究中，主要是利用釕奈米金屬還原在材料 (Fe3O4@SiO2@KIT-6)中，因材料具有磁性可藉由外加磁場的方式將催化劑與反應溶劑分離，使用化學還原法可有效地將 Ru NPs 快速地還原在材料中。本部分實驗將合成出來的催化劑 Ru(X)/Y% Fe3O4@SiO2@KIT-6 經由儀器鑑定後並應用在硼烷氨水解脫氫上，研究中也探討不同濃度(M/AB)、反應溫度及促進劑 NaOH 用量等優化條件，以加速硼烷氨水解脫氫反應進行。經過實驗優化，Ru(2)/10% Fe3O4@SiO2@KIT-6 於鹼性條件下表現出良好的催化活性，其轉換頻率 (TOF) 達 290.7 min-1。

摘要(英)

This thesis consists of two parts. In the first part, sulfonic acid (-SO3H) functionalized mesoporous silica KIT-6 was synthesized and used as heterogeneous catalyst for the esterification of oleic acid. One pot co- condensation approach was used to synthesize the -SO3H functionalized 3D mesoporous silica KIT-6 using tetraethoxysilane (TEOS) and mercaptopropyltrimethoxysilane (MPTMS) as the silicon precursors. Prepared materials were characterized by SAXRD, N2 adsorption- desorption isotherm, SEM etc. –SO3H functionalized KIT-6 showed excellent catalytic activity for the esterification of oleic acid with methanol due to its high surface area, pore volume, and plenty of acidic sites in it. The effects of different parameters, such as, amount of –SO3H loading, initiator ratio, catalyst dosage and reaction temperature on the catalytic activity were also explored. KIT-6 functionalized with 10 mol% sulfonic acid groups (K6S10) was judged as the best catalyst in the optimized experimental conditions with a high conversion rate of 98% at OA/MeOH = 1:20 and a reaction time of 4 hours.
In the second part, the main work is to synthesize ruthenium nanoparticles within the pores of mesoporous silica martial (Fe3O4@SiO2@KIT-6) support, and use them as the catalysts for the hydrolytic dehydrogenation of ammonia borane. The metal nanoparticles were immobilized within the support by the double agent chemical reduction method using NaBH4 and NH3BH3 as the reducing agents. The synthesized Ru (X)/Y%Fe3O4@SiO2@KIT-6 materials were characterized by PXRD, N2 adsorption-desorption isotherm, SEM etc. Catalyst Ru(2)/10% Fe3O4@SiO2@KIT-6 exhibited high catalytic activity and turnover frequency up to 290.7 min-1, activation energy of 33.82 kJ/mol.

關鍵字(中)

★ 中孔洞材料
★ 酯化
★ 奈米金屬粒子
★ 硼烷氨
★ 脫氫

關鍵字(英)

★ mesoporous material
★ esterification
★ nanoparticles
★ ammmonia borane
★ dehydrogenation

論文目次

摘要..................................................................................................... I Abstract.................................................................................................... II 目錄............................................................................................................V 圖目錄...................................................................................................... XI 表目錄..................................................................................................... XX 1 第一章序論 ..........................................................................................1
1-1 中孔洞矽材 (Mesoprous 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 中孔洞矽材合成方式......................................................4 1-1-4 界面微胞型成方式及種類..............................................6 1-1-5 微胞與矽源的作用力......................................................9
1-2 中孔洞矽材/中孔洞矽材表面修飾..............................................11 1-2-1 三維中孔洞矽材 KIT-6.................................................11 1-2-2 中孔洞矽材表面官能基修飾法....................................12 1-2-3 中孔洞矽材表面修飾磺酸官能基................................15
V

1-2-4 中孔洞矽材表面修飾羧酸官能基................................18 第壹部分具磺酸官能基中孔洞矽材催化油酸(OA)為油酸甲酯(MO) ...............................................................................................................22 1-3 油酸酯化反應...............................................................................22
1-3-1 油酸甲酯介紹................................................................22 1-3-2 磺酸化中孔洞矽材催化油酸酯化反應文獻回顧.......23 1-3-3 油酸酯化反應機制........................................................25
第貳部分奈米釕金屬催化硼烷氨產氫............................................27 1-4 釕奈米金屬催化硼烷氨產氫.......................................................27 1-4-1 硼烷氨水解產氫............................................................27 1-4-2 奈米金屬粒子對硼烷氨水解脫氫之文獻 ...................28 1-4-3 金屬催化硼烷氨水解脫氫的反應機制圖 ...................33 1-5 研究動機與目的...........................................................................34 2 第二章實驗部分 ................................................................................35 2-1 實驗藥品.......................................................................................35 2-1-1 第壹部分所使用之藥品................................................35 2-1-2 第貳部分所使用之藥品................................................37 2-2 實驗設備.......................................................................................38
VI

2-2-1 實驗合成設備................................................................38
2-2-2 實驗鑑定儀器................................................................38 2-3 儀器鑑定之原理...........................................................................40 2-3-1 同步輻射中心光束線(NSRRC)....................................40 2-3-2 氮氣吸附脫附儀 (ASAP).............................................43 2-3-3 掃描式電子顯微鏡 (SEM)...........................................46 2-3-4 穿透式電子顯微鏡 (TEM) ..........................................48 2-3-5 粉末 X 光繞射儀 (PXRD) ...........................................49 2-3-6 高解析感應耦合電將質譜分析(ICP-MS)...................50 2-3-7 光電子能譜 (XPS)........................................................51 2-3-8 傅立葉紅外線吸收光譜儀 (FTIR)..............................52 2-3-9 固態核磁共振 (Solid State NMR) ...............................53 2-3-10 元素分析儀 (EA)........................................................57 2-3-11 超導量子干涉磁化儀 (SQUID).................................58 2-3-12 氣相層析儀 (GC) .......................................................59 2-3-13 熱重分析儀 (TGA).....................................................61 2-4 實驗步驟.......................................................................................62 第壹部分具磺酸官中孔洞矽材催化油酸(OA)為油酸甲酯(MO) ..62
VII

2-4-1 合成具酸性官能基之 K6SX.........................................62 2-4-2 以硫酸溶液裂解孔洞中模板........................................63 2-4-3 催化油酸為油酸甲酯實驗............................................64
第貳部分奈米釕金屬催化硼烷氨產氫............................................67 2-4-4 合成具有磁性的孔洞材料 Y wt.%Fe3O4@SiO2@KIT-6 ...................................................................................................67 2-4-5 合成釕奈米金屬於磁性材料中 Ru(X)/20wt.% Fe3O4@SiO2@KIT-6 ................................................................69 2-4-6 材料進行硼烷氨催化水解產氫....................................71
3 第三章結果與討論............................................................................75 第壹部分具磺酸官能基中孔洞矽材催化油酸為油酸甲酯............75 3-1 材料鑑定.....................................................................................75
3-1-1 小角度 X 光繞射圖 (SAXRD) ....................................75 3-1-2 氮氣吸脫附鑑定 (BET)...............................................78 3-1-3 傅立葉轉換紅外線光譜儀 (FTIR)..............................80 3-1-4 Solid NMR ......................................................................81 3-1-5 元素分析 (EA)..............................................................86 3-1-6 掃描式電子顯微鏡 (SEM)...........................................87
VIII

3-1-7 穿透式電子顯微鏡 (TEM) ..........................................89 3-1-8 光電子能譜 (XPS)........................................................92 3-1-9 熱重分析(TGA).............................................................95
3-2 催化油酸為油酸甲酯實驗.........................................................96 3-2-1 K6SX 催化油酸酯化反應..............................................96 3-2-2 K6Y10 催化油酸酯化反應............................................98 3-2-3 不同比例起始物對MO產率之影響.........................100 3-2-4 不同比例催化劑對MO產率之影響.........................102 3-2-5 不同反應溫度對MO產率之影響.............................104 3-2-6 K6S10 催化油酸為油酸甲酯重複使用實驗 ..............107
第貳部分奈米釕金屬催化硼烷氨產氫..........................................115 3-3 材料鑑定...................................................................................115 3-3-1 小角度 X 光繞射圖 (SAXRD) ..................................115 3-3-2 大角度 X 光繞射圖 (WAXRD) .................................117 3-3-3 等溫氮氣吸脫附鑑定 (BET).....................................119 3-3-4 掃描式電子顯微鏡 (SEM).........................................122 3-3-5 穿透式電子顯微鏡 (TEM) ........................................126 3-3-6 光電子能譜 (XPS)......................................................132
IX

3-3-7 感應耦合電漿質譜儀 (ICP-MS)................................134
3-3-8 磁性鑑定 (SQUID).....................................................136 3-4 奈米釕金屬催化硼烷氨產氫實驗...........................................137 3-4-1 Ru(X)/20wt.%Fe3O4@SiO2@KIT-6 催化硼烷氨水解反應.............................................................................................138 3-4-2 Ru(2)/Y wt.%Fe3O4@SiO2@KIT-6 催化硼烷氨水解反應 .................................................................................................140 3-4-3 不同材料對催化硼烷氨水解反應..............................142 3-4-4 不同M/AB比例對硼烷氨水解反應之比較.............144 3-4-5 不同比例 NaOH 促進劑對硼烷氨水解反應之比較.146 3-4-6 不同溫度對硼烷氨水解反應......................................148 3-4-7 Ru(2)/10%Fe3O4@SiO2@KIT-6 對硼烷氨製氫重複利用之反應 ....................................................................................152 第四章結論...........................................................................................157 第五章參考文獻..................................................................................158

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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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