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研究生：	王育源 Wang, Yu-Yuan
論文名稱：	製備擔載鈉離子的沸石觸媒應用在三酸甘油酯轉酯化成生質柴油之研究 The study of sodium-loaded zeolite catalysts for transesterification of triglycerides to biodiesel
指導教授：	陳炳宏 Chen, Bing-Hung
學位類別：	博士 Doctor
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2018
畢業學年度：	106
語文別：	英文
論文頁數：	124
中文關鍵詞：	生質柴油、脂肪酸甲酯、轉酯化反應、三酸甘油酯、異相觸媒、沸石
外文關鍵詞：	Biodiesel, Fatty acid methyl ester (FAME), Transesterification, Triglyceride, Heterogeneous catalyst, Zeolite
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本文的研究是利用轉酯化反應可將三酸甘油酯進一步轉化成生質柴油的特性，例如三油酸甘油酯在過量甲醇下的反應可透過沸石觸媒去完成。幾種不同組成的沸石觸媒，包含沸石HY、MCM-22 與Beta，可被我們合成出來並且利用鹼離子交換過程去進行修飾，這種經過修飾過的觸媒可提供轉酯化反應在65C度以下仍保有良好的催化性質。

沸石MCM-22與HY (CBV-780)這兩種觸媒如果沒有事先適度地進行表面修飾處理過的話，都不能有效地將三油酸甘油酯催化成為脂肪酸甲酯（生質柴油）。例如，使用沸石MCM-22去進行轉酯化反應了90小時後，三油酸甘油酯轉化成生質柴油的產率只有16.3%；而使用沸石HY去進行轉酯化反應了90小時後，三油酸甘油酯轉化成生質柴油的產率大約有90%。相比之下，將上述的沸石觸媒透過鈉離子交換法進行表面修飾後卻可以大大的提高其轉化率，例如，經過氫氧化鈉水溶液處理過的沸石MCM-22與HY，在5.5小時之內可分別使三油酸甘油酯轉化成生質柴油的產率為98%與99%，雖然經過氫氧化鈉水溶液處理過的沸石觸媒本身結構有些會變成非晶相物以及其BET表面積的喪失，但是並沒有觀察到有皂化現象的出現。在觸媒進行鈉離子交換的過程中，其參數包含溫度、反應時間、pH值、以及鈉離子來源(氫氧化鈉、氯化鈉與硫酸鈉)的濃度都被拿來探討其對於三油酸甘油酯轉化成生質柴油的轉化率有什麼影響。最後的結果可發現在65C度的三酸甘油酯轉化成生質柴油的轉化率可以高達97.3%。

帶有高矽鋁比特性的沸石Beta可透過氟離子利用水熱法去合成出來，並且可以在三油酸甘油酯轉化成生質柴油的轉酯化反應中被拿來當作異相催化劑，合成後具有高矽鋁比特性的沸石Beta可接著進行氫氧化鈉水溶液的適當處理，此步驟的目的是為了得到具有較佳催化能力的觸媒以利於轉酯化反應的進行。因此，透過此修飾過的沸石Beta可在迴流反應的情況下在一小時內可得到超過90%的轉化率；而且，此經過鈉離子修飾過的沸石觸媒在轉酯化反應過程中依然展現不錯的循環耐久性，因為此觸媒在經過重複八次的轉酯化反應之後，其三油酸甘油酯轉化成生質柴油的轉化率仍然保有不錯的催化能力。

在轉酯化反應的過程之中，這些經過表面修飾過的沸石觸媒所展現的催化作用，透過固態核磁共振光譜分析、孔洞分析法與其他的儀器分析的結果可推測出其主要的反應機制是利用沸石觸媒表面上的鹼性活性點去促進轉酯化反應的進行，在轉酯化反應進行期間，鈉陽離子會儲存在經過氫氧化鈉水溶液修飾過的沸石Beta觸媒之中的大孔洞與表面缺陷點(defect sites)之中，並且適當的補給到觸媒的表面去增強觸媒在轉酯化反應中的催化能力。

A study of biodiesel production via transesterification of triglycerides, such as triolein, in excess methanol in presence of zeolite catalysts was carried out. Various zeolite frameworks, including HY, MCM-22 and Beta, were synthesized and modified, mainly with alkali ion exchange processes, to render satisfactory catalysis in transesterification at a temperature lower than 65°C.

Zeolite MCM-22 and zeolite HY (CBV-780) could not effectively catalyze the transesterification of triolein without prior proper surface modifications. For example, a conversion efficiency of triolein to biodiesel near 16.3% and ca. 90% was obtained with the use of zeolite MCM-22 after a 90-h reaction and with zeolite HY after a 40-h reaction. In contrast, the conversion yields were much improved with Na+ ion-exchange to the surface of the aforementioned zeolite catalysts. For example, the yields of triolein to biodiesel reached 98% and 99% within a 5.5-hour reaction, respectively, using the NaOH-treated HY and MCM-22 catalysts, even though these NaOH-treated catalysts became amorphous and suffered a loss of the Brunauer-Emmett-Teller (BET) surface area. No saponification was observed using these NaOH-treated catalysts. The process parameters of the ion-exchange process to activate Zeolite HY catalysts, including the temperature, the process time, the pH value, as well as the concentrations and sources of the Na+ cations (NaOH, NaCl and Na2SO4), on the conversion yield of triolein to biodiesel were investigated accordingly. As a result, a high conversion yield of triglycerides to biodiesel at 97.3% was obtained at 65°C.

Zeolite Beta with a high Si/Al ratio as a heterogeneous catalyst in the transesterification of triolein for biodiesel production was synthesized hydrothermally in fluoride media. The prepared Zeolite Beta was subsequently treated with dilute NaOH solutions to obtain better catalysis in the transesterification reaction. A conversion efficiency of over 90% could be attained within an hour of the reflux reaction. Moreover, these Na-treated zeolite catalysts still exhibit acceptable durability and good catalysis in the transesterification reaction after nine consecutive cycles.
The main mechanism on the catalysis of these surface-modified zeolites is inferred from the alkali active sites on the surface of zeolites based on the surface characterization of the catalysts mainly through the use ofwith solid-state NMR, Porosimetry, and other instruments. During the transesterification reaction, sodium cations existing in the cages and the defect sites of the NaOH-treated Zeolite Beta can be supplied to the surface of the catalysts and, thus, enhance the catalysis.

中文摘要	I
ABSTRACT	III
ACKNOWLEDGEMENTS	V
CONTENTS	VII
LIST OF TABLES	XI
LIST OF FIGURES	XIII
INTRODUCTION	1
1 Research Background and Motivation	1
2 Research Contributions and Objectives	2
3 Outlines	3
LITERATURE REVIEW	5
1 Introduction	5
2 Overview of Biodiesel	7
2.1 What is biodiesel	7
2.2 The origin of biodiesel	8
2.3 Advantages and disadvantages of biodiesel	9
2.4 The development of biodiesel	11
3 Transesterification reaction	16
3.1 Introduction	16
3.2 Homogeneous catalysts	19
3.3 Heterogeneous catalysts	22
3.4 Lipase catalysts	24
4 Zeolite catalyst	25
4.1 Introduction to zeolite	25
4.2 Zeolite Y	28
4.3 Zeolite MCM-22	31
4.4 Zeolite Beta	32
EXPERIMENTAL METHODS	35
1 Materials and Main Instruments	35
1.1 Materials	35
1.2 Main Instruments	36
2 Characterization Methods	37
2.1 Scanning electron microscope (SEM) and energy dispersive X-ray spectrometer (EDS)	37
2.2 Micromeritics ASAP 2020 porosimeter	38
2.3 X-ray diffractometer (XRD)	39
2.4 Inductively coupled plasma optical emission spectrometer (ICP-OES) and Atomic Absorption Spectroscopy (AA)	40
2.5 Liquid-state Nuclear Magnetic Resonance spectrometer (1H- NMR)	41
2.6 Solid-state Nuclear Magnetic Resonance spectrometer (ss NMR)	41
2.7 Model Start S, Milestone Srl, (Italy)	43
3 Preparation of sodium-loaded Catalysts	44
3.1 Synthesis of MCM-22	44
3.2 Synthesis of high silica Beta	45
3.3 Modification of catalysts	46
3.3.1 Surface Modification of CBV-780, MCM-22 and Si-Al catalysts with NaOH	46
3.3.2 Surface Modification of CBV-780 for different Na+ sources	46
3.3.3 Surface Modification of Zeolite Beta	47
3.4 Recycling catalyst	48
4 Experiment method	48
4.1 Preparation of catalysts	48
4.2 Transesterification reaction at 60°C	48
4.3 Transesterification reaction by reflux	51
4.4 Transesterification reaction by microwave	52
5 Analytical Methods	53
5.1 Introduction	53
5.2 Analysis of biodiesel	54
5.3 Catalysts analysis	55
RESULTS AND DISCUSSION	57
1 Performance of Zeolite MCM-22 and commercial CBV-780.	58
1.1 Characterization of As-Synthesized Zeolite MCM-22 and Other Catalysts	58
1.2 Transesterification of triolein in methanol	62
1.3 Physical property of catalysts after and before transesterification	65
1.4 Catalystic effect of Na+ cation on the surface of catalyst for transesterification	66
2 Optimization of sodium loading on zeolite support for transesterification	69
2.1 Introduction	69
2.2	Effects of the sodium source and the Na+ concentration in the ionexchange process	69
2.3 Effects of the duration of the sodium ion-exchange process	75
2.4 Cyclic durability of the catalyst	77
3 Performance of As-Synthesized Zeolite Beta	79
3.1 Introduction	79
3.2 Characterization of Zeolite Beta	79
3.3 Catalyzed transesterification reaction by reflux and microwave heating process	85
3.4 Surface chemistry of the Na (0.5, 27) before and after transesterification reaction	92
3.5 Discussion of Na-BEA structure	97
CONCLUSIONS AND RECOMMENDATIONS	101
1 Conclusions	101
2 Recommendations	103
REFERENCE	105
CURRICULUM VITAE	123
                                    

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