本研究旨在開發複合式固體觸媒，可作為永續性環化反應製程之應用，來製備有機環化合物。在第一部份中，我們選擇從3-單氯丙二醇(3-MCH)到縮水甘油(GLD)的脫酸環化(Cyclodehydrohalogenation)反應作為研究的代表反應。透過建立合適的合成、鑑定和活性測試平台，研究氧化鈣與氧化鎂的複合式固體鹼觸媒的活性、選擇性和操作穩定性與其材料性能的關係。我們使用X光繞射儀(XRD)、掃描式電子顯微鏡(SEM)、比表面積與孔徑分析儀(BET)、化學吸附儀(TPD)與感應耦合電漿發射光譜儀(ICP-OES)來進行觸媒材料性質之相輔式鑑定。結果表示，我們可以成功合成具有可調控式表面鹼度的複合式固體鹼觸媒。液-固反應系統有助於理解固體鹼觸媒催化的3-MCH脫酸環化的反應機理，尤其是副產物的產生途徑和表面中毒引起的觸媒失活。結果表明，3-MCH脫酸環化轉化為GLD的轉化速率與催化劑上中鹼性位點的數量成正比，對GLD的選擇率與催化劑的中等鹼性強度成正比。
在第二部份中，我們運用氧化鈰奈米粉體作為固體觸媒，以催化丙二醇(PG)與二氧化碳(CO2)反應合成出環狀碳酸丙烯酯(PC)。而我們利用高壓反應器(Auto-clave)與通以流動CO2的常壓半批次(Semi-batch)反應器，來研究二氧化鈰觸媒與反應中水分的存在對活性的影響。結果顯示，我們可以在不使用任何脫水劑的情況下使用雙溶劑系統獲得高選擇率(>99.9 %)的碳酸丙烯酯(PC)。藉由勒沙特列原理，透過將水分的移除可提高產物的收率。同時，在沒有溶劑存在下過量觸媒(> 5%)將會促進醚類的催化。
本研究中獲得的實驗結果基礎對於由脫酸環化反應與碳酸酯化反應來生產有機環化合物的複合式固體觸媒提供了有價值的設計原理，並藉由開發複合式固體觸媒之研究作為永續性環化反應製程發展之應用。

In this work, we aim to develop a synthesis, characterization, and performance testing platform for sustainable synthesis of cyclic organic compounds by facile synthesis composite solid catalysts. In the first part, the cyclodehydrohalogenation of 3-monochlorohydrin (3-MCH) to glycidol (GLD) was chosen as the representative of the study. The activity, selectivity, and operation stability of the developed composite catalysts versus their material properties were studied through the establishment of a suitable synthesis, characterization, and performance testing platform. X-ray diffractometer, scanning electron microscope, Brunauer-Emmett-Teller N2 adsorption analyzer, chemisorption analyzer, and inductively coupled plasma optical emission spectrometer are used complementarily for the characterization of catalyst materials. The results show that we can successfully synthesize composite solid base catalysts with adjustable chemical and physical properties, including surface basicity. The liquid-solid reaction system is useful for the mechanistic understanding of the cyclodehydrohalogenation of 3-MCH catalyzed by the solid base catalysts, especially the by-product generation paths and the catalyst deactivation by surface poisoning. The results show that the conversion rate of cyclodehydrohalogenation of 3-MCH to GLD was proportional to the amount of total basic sites on the catalyst, and the selectivity to GLD was proportional to the medium basicity strength of the catalyst.
In the second part, we chose to study the reaction of synthesis cyclic propylene carbonate (PC) from carbon dioxide (CO2) and propylene glycol (PG) catalyzed by CeO2 nanocatalyst as the model study. The activity results were studied through high-pressure auto-clave reactor and CO2 flow semi-batch reactor. The results show we achieved direct synthesis of PC in high selectivity (>99.9%) by dual-solvent system without using dehydrating agents. The product yield increased via the removal of water following the Le Chatelier's principle, by which the hydrolysis of product can be effectively reduced. The formation of ether was promoted due to the excess amount of catalysts without solvent. The fundamental understanding obtained in this study provides valuable design principles for composite solid catalyst for a wide variety of dehydrohalogenation and carbonate-esterification reactions to manufacture organic cyclic compounds.

摘要 I
Abstract II
致謝 IV
目錄 VI
圖目錄 VIII
表目錄 X
第一章 緒論 1
1.1 前言 1
1.2 複合式固體觸媒之製備與應用 3
1.3 由3-單氯丙二醇經由脫酸環化反應生成縮水甘油 5
1.4 由二氧化碳和丙二醇進行反應形成環狀碳酸酯 7
1.5 開發實現環境永續的化工製程 9
第二章 實驗方法及儀器 11
2.1 實驗藥品 11
2.2 固體鹼觸媒製備-共沉澱法與觸媒造粒技術 13
2.3 分析儀器介紹 15
2.3.1 掃描式電子顯微鏡(Scanning Electron Microscope, SEM) 15
2.3.2 X光繞射儀(X-ray diffraction, XRD) 16
2.3.3 比表面積與孔隙度分析儀(Brunauer-Emmett-Teller, BET) 17
2.3.4 感應耦合電漿發射光譜儀（Inductively Coupled Plasma Optical Emission Spectrometry, ICP-OES） 18
2.3.5 熱重分析儀 (Thermogravimetric Analyzer, TGA) 19
2.3.6 化學吸附分析儀 20
2.3.7 氣相層析質譜儀 (Gas Chromatography-Mass Spectrometry, GC-MS) 21
2.3.8 高解析電子能譜儀(High resolution X-ray Photoelectron Spectrometer, HR-XPS) 22
2.4 複合式固體觸媒活性與穩定性測試 23
2.4.1 脫酸環化反應測試系統 23
2.4.2 碳酸酯化反應測試系統 25
2.4.3 產物分析技術 28
第三章 結果與討論 32
3.1 以共沉澱法製備Ca-Mg-Al複合式固體鹼觸媒進行脫酸環化反應 33
3.1.1 材料分析 33
3.1.2 鹼度分析 41
3.1.3 催化活性測試-連續式固定床反應器 44
3.1.4 反應機制探討 46
3.2 運用CeO2粒子作為固體觸媒進行催化丙二醇與CO2反應生成環狀碳酸酯 55
3.2.1 材料分析 55
3.2.2 鹼度分析 59
3.2.3 由丙二醇與CO2生成環狀碳酸丙烯酯之活性測試 61
第四章 結論 72
第五章 未來展望 74
第六章 參考文獻 77

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