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研究生：	黃振哲 Huang, Zhen-Zhe
論文名稱：	偏矽酸鋰催化甘油轉酯化製備碳酸甘油酯之最佳化研究 Study on Optimization of Catalytic Transesterification of Glycerol to Glycerol Carbonate over Lithium Metasilicate
指導教授：	陳炳宏 Chen, Bing-Hung
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2021
畢業學年度：	109
語文別：	中文
論文頁數：	155
中文關鍵詞：	偏矽酸鋰、甘油、碳酸甘油酯、轉酯化、反應曲面法
外文關鍵詞：	Glycerol, Glycerol carbonate, Lithium metasilicate, Transesterification, Response surface methodology
相關次數：	點閱：103 下載：0
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自第一次工業革命起，化石燃料成為推動人類文明科技進步及經濟成長最重要的能源之一，隨著化石燃料被大量使用，卻也衍生出許多問題。除了造成環境汙染外，化石燃料屬於非再生能源，過度消耗也將造成資源匱乏，尋找低汙染、具永續性的可再生能源已成了各國重要的課題之一。其中，生質柴油具生物可降解性、低碳排放量、物化性質與傳統柴油類似等性質，因此被當作其替代能源大量生產。隨著生質柴油產業的蓬勃發展，卻也造成主要副產物甘油在市場上供需失衡，導致其價格驟跌並衝擊生質柴油產業發展。尋找甘油高值化之應用以鞏固其價格與生質柴油市場也成了當務之急。碳酸甘油酯具有豐富的官能基團，可望被應用在溶劑、化學中間體、鋰離子電池等產業中，近年來成為甘油高值化中富有發展潛力的化學品之一。
本研究利用水熱合成法來製備偏矽酸鋰做為催化甘油與碳酸二甲酯之轉酯化反應之非均相觸媒，使用XRD、SEM、BET、FT-IR、ssNMR、TGA等儀器鑑定觸媒之特性，探討其水熱合成之反應溫度及低溫鍛燒之影響，並測試催化活性。並使用反應曲面法中的面中心中央合成設計法(FCCCD)找出碳酸甘油酯最佳化產率及反應條件，並在最佳條件下進行動力學分析及耐用性測試，並與商用觸媒進行比較。
經由實驗結果選擇以水熱合成法在90°C下反應2小時，並在200°C鍛燒6小時後之偏矽酸鋰作為主要觸媒，在觸媒甘油重量比2 wt%下經由實驗設計法可得最佳反應條件為反應溫度87°C、反應時間2小時7分、碳酸二甲酯和甘油莫耳比為2.77，並可得到碳酸甘油酯之產率為95.40%，驗證實驗結果為95.16±0.22%；使用商用偏矽酸鋰所得產率則為92%。反應動力學則藉由Langmuir-Hinshelwood模型推導可得知甘油轉酯化反應為類一階反應，由實驗結果可得到其反應活化能為110.13 kJ/mol。在耐用性測試上，自行合成及商用偏矽酸鋰觸媒在反應至第6次產率仍可達74%及82%，經儀器鑑定結構並無明顯破壞，具良好之耐用性。

The catalytic transesterification of glycerol (G) with dimethyl carbonate (DMC) producing glycerol carbonate (GC) using lithium metasilicate (Li2SiO3) as heterogeneous base catalyst was studied in this work. Li2SiO3 catalyst was prepared by hydrothermal reaction using fumed silica as a starting material with an addition of 2M LiOH(aq) at 90°C for 2 h, followed by calcined at 200°C for 6 h. The catalysts were characterized by XRD, TGA, FTIR, BET, SEM, and ssNMR. Its basicity was also measured. Typically, the transesterification of glycerol with dimethyl carbonate was performed from 60°C to 100°C in a round-bottomed flask equipped with a condenser. Additionally, the design-of-experiment (DOE) principle, response surface methodology (RSM) coupled with face-centered central composite design (FCCCD), was attempted to optimize the transesterification process of glycerol. The yield of glycerol carbonate is the selected response factor. Under the optimized parameters of 87°C reaction temperature, 127 min reaction time and DMC/G molar ratio of 2.77, the yield of GC reached 95.16% with 2 wt% Li2SiO3 catalyst. After reused of lithium metasilicate for 5 cycles, the yield could still reach 74%. Based on the Langmuir-Hinshelwood mechanism, the Li2SiO3-catalyzed transesterification reaction appeared to follow pseudo-first-order kinetics with an activation energy of 110.13 kJ/mol.

摘要	I
Abstract	II
致謝	XVIII
目錄	XIX
圖目錄	XXVI
表目錄	XXXI
第一章 緒論	1
1 前言	1
2 研究動機與目的	4
第二章 文獻回顧	6
1 甘油介紹	6
1.1 甘油之物理化學性質	6
1.2 甘油之歷史發展	7
1.3 甘油來源	9
1.3.1 皂化反應	9
1.3.2 酸性催化轉酯化反應	10
1.3.3 鹼性催化轉酯化反應	10
1.3.4 酶催化轉酯化反應	11
1.3.5 水解反應	11
1.4 粗甘油純化	12
1.5 甘油之市場與利用	13
1.5.1 甘油之市場趨勢	13
1.5.2 甘油之商業應用	14
2 碳酸甘油酯之介紹	16
2.1 碳酸甘油酯之物理化學性質	16
2.2 碳酸甘油酯之來源	18
2.3 碳酸甘油酯之應用	18
2.3.1 化學溶劑	19
2.3.2 鋰離子電池	19
2.3.3 建築複合材料	20
2.3.4 化妝品及個人護理清潔	20
2.3.5 氣體分離	21
2.3.6 化學中間體	21
2.4 碳酸甘油酯之分析方法	23
2.4.1 氣相層析法	23
2.4.2 高效液相層析法	23
2.4.3 核磁共振法	23
3 以甘油合成碳酸甘油酯之反應路徑	25
3.1 光氣法	25
3.2 尿素轉酯化法	26
3.3 有機碳酸酯轉酯化反應法	27
3.3.1 以直鏈碳酸酯與甘油合成碳酸甘油酯	27
3.3.2 以環狀碳酸酯與甘油合成碳酸甘油酯	29
3.4 羰化法	30
3.4.1 以一氧化碳氧化羰基化反應	30
3.4.2 以二氧化碳直接羰基化反應	32
4 偏矽酸鋰	38
4.1 偏矽酸鋰之合成	38
4.2 偏矽酸鋰之應用	40
4.3 矽酸鹽類簡介	41
5 實驗設計法(Design of Experiment, DOE)	43
5.1 實驗設計之發展史	43
5.2 實驗設計之基本原則	44
5.3 實驗設計之步驟	45
5.4 實驗設計之種類	45
5.4.1 因子設計法(factorial design)	45
5.4.2 反應曲面法(Response surface methodology, RSM)	47
5.4.3 田口設計法(Taguchi method)	51
第三章 實驗儀器與研究方法	52
1 實驗架構	52
2 實驗藥品	53
3 實驗設備	54
4 實驗方法	55
4.1 偏矽酸鋰觸媒合成	55
4.2 甘油轉酯化反應	55
4.3 觸媒回收	55
4.4 矽烷化	56
4.5 碳酸甘油酯產率分析方法	57
4.6 反應曲面實驗設計法	59
4.7 觸媒鑑定與分析	62
4.7.1 X光繞射分析儀 (X-ray Diffraction Analyzer, XRD)	62
4.7.2 比表面積與孔隙分布分析儀 (Specific Surface Area & Pore Size Distribution Analyzer, BET)	63
4.7.3 傅立葉紅外線光譜儀 (Fourier Transform Infrared Spectrometer, FTIR)	64
4.7.4 掃描式電子顯微鏡 (Scanning Electron Microcope, SEM)	65
4.7.5 能量散佈X-射線光譜儀 (Energy-dispersive X-ray spectroscopy, EDS)	66
4.7.6 熱重分析儀 (Thermogravimetric analysis, TGA)	66
4.7.7 感應耦合電漿放射光譜儀 (Inductively coupled plasma optical emission spectrometer, ICP-OES)	67
4.7.8 固態核磁共振儀(Solid-state Nuclear Magnetic Resonance, ssNMR)	67
4.7.9 觸媒鹼度測試	68
4.7.10 觸媒酸性點位鑑定	69
第四章 結果與討論	70
1 碳酸甘油酯產物定量分析	70
2 偏矽酸鋰觸媒之合成與鑑定	73
2.1 不同合成反應溫度對合成偏矽酸鋰之影響	73
2.1.1 XRD晶型分析	74
2.1.2 SEM晶型分析	76
2.1.3 ICP檢測	78
2.1.4 觸媒鹼度測試	78
2.1.5 BET比表面積比較	79
2.2 鍛燒與否對自行合成偏矽酸鋰之影響	81
2.2.1 XRD晶型分析	81
2.2.2 TGA分析	82
2.2.3 比表面積及孔隙分佈分析	83
2.2.4 FT-IR圖譜分析	83
2.2.5 觸媒鹼度測試	85
2.2.6 鍛燒前後觸媒對催化反應之影響	85
2.2.7 觸媒反應前後之晶型結構分析	86
2.2.8 觸媒反應前後之比表面積及孔隙分佈分析	88
2.2.9 觸媒反應前後之FT-IR圖譜分析	88
2.2.10 觸媒反應前後之鹼度測試	90
2.3 自行合成與商用偏矽酸鋰之比較	91
2.3.1 XRD晶型分析	91
2.3.2 TGA分析	92
2.3.3 SEM及EDS分析	93
2.3.4 比表面積及孔隙分佈分析	95
2.3.5 FT-IR圖譜分析	97
2.3.6 ssNMR分析	99
2.3.7 觸媒鹼度分析	101
2.3.8 觸媒酸性測試	101
3 實驗設計	103
3.1 前實驗	103
3.1.1 反應溫度對碳酸甘油酯產率之影響	103
3.1.2 反應時間對甘油轉酯化反應之影響	104
3.1.3 碳酸二甲酯與甘油莫耳比對甘油轉酯化反應之影響	105
3.1.4 觸媒甘油重量比對甘油轉酯化反應之影響	105
3.1.5反應曲面法模型之選擇	106
3.2 迴歸分析	107
3.3 變異數分析	110
3.4 最佳條件預測	112
3.5 驗證實驗	113
4 反應動力學探討	114
4.1 反應動力學之模型	114
4.2 反應活化能之計算	119
5觸媒之回收再利用測試	121
5.1自行合成與商用偏矽酸鋰觸媒耐用性測試	121
5.2 XRD晶型分析	122
5.3 SEM與EDS分析	124
5.4 TGA分析	126
5.5 FT-IR圖譜分析	127
5.6 ssNMR分析	129
5.7 比表面積及孔隙分佈分析	131
5.8 ICP測試及觸媒鹼度分析	133
第五章 結論與未來展望	136
1 結論	136
2 未來展望	137
參考文獻	138
附錄	150
附錄A	150
附錄B	150
附錄C	153
附錄D	153
附錄E	154
                                    

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