製備酸性官能基中孔洞矽材與鈀鐵奈米雙金屬中孔洞/石墨烯碳複合材應用在有機催化反應

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許宏誠(Hung-Cheng Hsu) 查詢紙本館藏

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化學學系

論文名稱

製備酸性官能基中孔洞矽材與鈀鐵奈米雙金屬中孔洞/石墨烯碳複合材應用在有機催化反應
(Sulfonic/Carboxylic Acid Functionalized Mesoporous Silica and Palladium Nanoparticles Embedded in the Carbon Composite for the Catalytic Organic Reaction)

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至系統瀏覽論文 (2027-6-30以後開放)

摘要(中)

本研究分為兩大部分。在第一部分研究中，利用直接合成法，將具有磺酸官能基與羧酸官能基團修飾在中孔洞矽材表面，合成出O-K6SXCY系列之酸性催化劑。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之官能基，期望能夠應用在催化1, 6-己二醇為丙烯酸酯。本部分將製備好的O-K6SXCY經過一系列的儀器鑑定後，確認催化劑的結構與穩定性後，進行己二醇酯化反應，分別探討了反應時間、酸性雙官能基催化劑比例、不同丙烯酸當量、不同聚合抑制劑量、不同催化劑量以及不同溫度對轉化率與產率之影響。經過一系列的實驗優化，最後以O-K6S20作為本部分的最佳催化劑，其HDDA在20小時的產率為72.8%，HDA在10小時的產率為50.4%。在此部分研究中，O-K6S20展現了其應用性與高催化活性。
第二部分研究中，主要是利用奈米雙金屬還原在中孔洞碳材 (CMK-9) 與還原氧化石墨烯 (rGO) 之碳複合材料上，利用化學還原法可有效地將PdNPs還原在碳複合材中，並藉由CMK-9具有高比表面積及rGO具有快速電子傳輸效率，能夠快速將電子提供給PdNPs，增加PdNPs的電子密度，進而提升催化活性。本部分將合成出來的Pd(x)/Y%Fe3O4@rGOC9系列經過儀器鑑定後，應用在鈴木偶聯反應中，並分別探討了不同比例的碳複合材 (rGOC9)、不同Fe3O4含浸量、不同PdNPs含浸量、不同催化材料、不同溶劑、不同鹼、不同芳基鹵化物、不同芳基硼酸和不同溫度對催化反應之影響。經過一系列的實驗優化，Pd(0.75)/10%Fe3O4@rGOC9展現了優異的催化活性，其轉化率與產率分別達99.0%與94.8%，周轉頻率 (TOF) 高達7920.0 h-1。

摘要(英)

This thesis consists of two parts, In the first part, we successfully synthesized the sulfonic acid and carboxylic acid functionalized mesoporous silicas (O-K6SXCY series) by direct synthesis using TEOS as silicon source, MPTMS or CES as functional group precursor, P123 as a soft template and hydrogen peroxide as an oxidant in an acidic environment. Among all the as-prepared catalysts, O-K6S20 has the best catalytic activity. According to the BET result, The synthesized O-K6S20 was confirmed about 679 m2/g. It has high surface area, good pore volume and high acid sites. It can increase the rate of acrylic acid and hexanediol to produce acrylate with 50.4% HDA yield and 72.8% HDDA yield at 90℃.
In the second part, the aim of this work is to synthesize bimetallic PdFe nanoparticles within the pores of mesoporous carbon (CMK-9) and reduced graphene oxide (rGO) composite support, and use them as the catalysts for the Suzuki-Miyaura cross-coupling reaction between iodobenzene and phenylboronic acid. The metal nanoparticles are immobilized within the support by double agent chemical reduction method which uses NaBH4 and NH3BH3 as the reducing agents. Due to high surface area of CMK-9 and fast electron efficiency of rGO, PdFe nanoparticles are dispersed homogenously within the rGOC9 composite support. The metal (Pd:Fe) contents are varied to explore its effect on the performance of the catalyst which showed that Pd(0.75)/10%Fe3O4@rGO C9 exhibited excellent catalytic activity with 97% conversion and turnover frequency up to 7760 h-1. The utilization of Fe3O4 as one of the components has not only reduced the production cost of the catalyst but also allowed its efficient recovery and reuse.

關鍵字(中)

★ 中孔洞矽材
★ 中孔洞碳材
★ 還原氧化石墨烯
★ 異相催化劑
★ 有機催化反應

關鍵字(英)

★ Mesoporous carbon materials
★ Mesoporous silica materials
★ Reduced graphene oxide
★ Heterogeneous catalysts
★ Organic reaction

論文目次

摘要 i
Abstract iii
謝誌 v
目錄 vii
圖目錄 xv
表目錄 xxvi
第一章緒論 1
第壹部分具酸性官能基中孔洞矽材催化己二醇為丙烯酸酯 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 3
1-1-4微胞形成的方式與種類 5
1-1-5微胞與矽源的作用力 8
1-2具官能基化之中孔洞矽材 10
1-2-1中孔洞矽材表面修飾法 10
1-2-2具羧酸官能基之中孔洞矽材 13
1-2-3具磺酸官能基之中孔洞矽材 16
1-3己二醇酯化反應 20
1-3-1丙烯酸酯介紹 20
1-3-2具磺酸官能基之中孔洞矽材酯化反應文獻回顧 21
第貳部分鈀鐵奈米雙金屬催化鈴木偶聯反應 24
1-4中孔洞碳材 (Mesoporous Carbon Materials, MCMs) 24
1-4-1中孔洞碳材之簡介 24
1-4-2奈米鑄模法合成中孔洞碳材 26
1-4-3奈米鑄模法合成中孔洞碳材之發展 27
1-5二維石墨材料 31
1-5-1石墨材料之簡介 31
1-5-2氧化石墨烯之合成 32
1-5-3還原氧化石墨烯之合成 34
1-6鈀鐵奈米雙金屬催化鈴木偶聯反應 36
1-6-1偶聯反應介紹 36
1-6-2鈀金屬催化鈴木偶聯反應機制介紹 37
1-6-3鈀金屬催化鈴木偶聯反應文獻回顧 38
1-7研究目的與動機 42
第二章實驗部分 43
2-1實驗藥品 43
2-1-1第一部份所使用之藥品 43
2-1-2第二部份所使用之藥品 44
2-2實驗步驟 45
第壹部分具磺酸官能基中孔洞矽材催化己二醇為丙烯酸酯 45
2-2-1合成具酸性官能基之O-K6SXCY 45
2-2-2以硫酸溶液裂解孔洞中模板 46
2-2-3催化己二醇為丙烯酸酯實驗 46
2-2-4催化己二醇為丙烯酸酯重複使用實驗 47
第貳部分鈀鐵奈米雙金屬催化鈴木偶聯反應 48
2-2-5合成還原氧化石墨烯 rGO 48
2-2-6合成中孔洞碳材CMK-9 48
2-2-7合成具有磁性材料之Y%Fe3O4@rGOC9 49
2-2-8合成鈀奈米金屬於磁性材料中Pd(x)/10%Fe3O4@rGOC9 49
2-2-9催化鈴木偶聯反應 51
2-2-10催化鈴木偶聯反應重複使用實驗 51
2-3 實驗儀器 52
2-3-1實驗合成所需之儀器 52
2-3-2實驗鑑定儀器 53
2-4鑑定儀器之原理 55
2-4-1同步輻射中心光束線 (NSRRC) 55
2-4-2氮氣吸附脫附儀 (ASAP) 57
2-4-3穿透式電子顯微鏡 (TEM) 61
2-4-4掃描式電子顯微鏡 (SEM) 62
2-4-5高解析感應耦合電漿質譜分析儀 (ICP-MS) 63
2-4-6光電子能譜 (XPS) 64
2-4-7粉末X光繞射儀（PXRD） 65
2-4-8傅立葉紅外線吸收光譜儀（FTIR） 66
2-4-9固態核磁共振（Solid State NMR） 67
2-4-10超導量子干涉磁化儀 (SQUID) 72
2-4-11元素分析儀 (EA) 73
2-4-12高效能液相層析儀 (HPLC) 74
2-4-13氣相層析儀 (GC) 76
2-4-14熱重分析儀 (TGA) 78
2-4-15拉曼光譜儀 (Raman) 79
第三章結果與討論 80
第壹部分具磺酸官能基中孔洞矽材催化己二醇為丙烯酸酯 80
3-1材料基本性質鑑定 80
3-1-1小角度X光繞射圖 (SAXRD) 80
3-1-2氮氣吸脫附鑑定 (BET) 83
3-1-3傅立葉轉換紅外線光譜圖 (FT-IR) 86
3-1-4 Solid NMR 87
3-1-4.1 13C CP/MAS 87
3-1-4.2 29Si MAS 90
3-1-5元素分析 (EA) 93
3-1-6掃描式電子顯微鏡 (SEM) 95
3-1-7穿透式電子顯微鏡 (TEM) 98
3-1-8光電子能譜 (XPS) 100
3-1-9熱重分析 (TGA) 103
3-2催化己二醇為丙烯酸酯實驗 104
3-2-1 O-K6SXCY催化己二醇為1,6-己二醇二丙烯酸酯 104
3-2-2 O-K6SXCY催化己二醇反應 106
3-2-3不同比例丙烯酸對HDDA產率之影響 107
3-2-4不同比例抑制劑對HDDA產率之影響 108
3-2-5不同比例催化劑對HDDA產率之影響 110
3-2-6不同溶劑對HDDA產率之影響 111
3-2-7不同溫度對HDDA產率之影響 112
3-2-8 O-K6S20催化己二醇為1-己二醇丙烯酸酯 115
3-2-9不同比例丙烯酸對HDA產率之影響 116
3-2-10不同比例抑制劑對HDA產率之影響 117
3-2-11不同比例催化劑對HDA產率之影響 118
3-2-12不同溶劑對HDA產率之影響 119
3-2-13不同溫度對HDA產率之影響 120
3-2-14 O-K6S20催化己二醇為丙烯酸酯重複利用之實驗 123
3-2-14.1 O-K6S20 5th 回收利用 123
3-2-14.2 O-K6S20 5th SEM 圖譜 124
3-2-14.3 O-K6S20 5th TEM 圖譜 124
3-2-14.4 O-K6S20 5th EA 126
3-2-14.5 O-K6S20 5th TGA 圖譜 127
第貳部分鈀鐵奈米雙金屬催化鈴木偶聯反應 128
3-3 材料基本性質鑑定 128
3-3-1小角度X光繞射圖 (SAXRD) 128
3-3-2大角度X光繞射圖 (WAXRD) 131
3-3-3等溫氮氣吸脫附鑑定 (BET) 134
3-3-4掃描式電子顯微鏡 (SEM) 140
3-3-5穿透式電子顯微鏡 (TEM) 144
3-3-6拉曼光譜 (Raman) 149
3-3-7光電子能譜 (XPS) 152
3-3-8熱重分析 (TGA) 155
3-3-9感應耦合電漿質譜儀 (ICP-MS) 156
3-3-10磁性鑑定 (SQUID) 158
3-4鈀鐵奈米雙金屬催化鈴木偶聯反應實驗 159
3-4-1碳複合材的探討與選用 159
3-4-1.1 Pd(1)@CMK-X 催化鈴木偶聯反應 159
3-4-1.2 Pd(1)@G/GO/rGO 催化鈴木偶聯反應 161
3-4-1.3 Pd(1)@rGOC9 催化鈴木偶聯反應 163
3-4-2 Pd(1)/Y%Fe3O4@rGOC9催化鈴木偶聯反應 164
3-4-3 Pd(x)/10%Fe3O4@rGOC9 催化鈴木偶聯反應 166
3-4-4不同材料催化鈴木偶聯反應之比較 168
3-4-5不同溶劑催化鈴木偶聯反應之比較 170
3-4-6不同鹼催化鈴木偶聯反應之比較 171
3-4-7不同芳基鹵化物催化鈴木偶聯反應之比較 173
3-4-8不同溫度催化鈴木偶聯反應之比較 175
3-4-9 Pd(0.75)/10%Fe3O4@rGOC9催化鈴木偶聯反應重複利用之實驗 179
3-4-9.1 Pd(0.75)/10%Fe3O4@rGOC9 10th 回收利用 179
3-4-9.2 Pd(0.75)/10%Fe3O4@rGOC9 10th SEM 圖譜 180
3-4-9.3 Pd(0.75)/10%Fe3O4@rGOC9 10th TEM 圖譜 180
3-4-9.4 Pd(0.75)/10%Fe3O4@rGOC9 10th SQUID 182
第四章結論 183
第五章參考資料 184

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指導教授

高憲明(Hsien-Ming Kao)

審核日期

2022-7-27

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