本論文研究藉由相間轉移觸媒（phase-transfer catalyst）之催化液-液相烷化反應，可在溫和條件下，將乙二醇（ethylene glycol）與溴化苄（benzyl bromide）合成為乙二醇二苄醚（1,2-bis(benzyloxy)ethane）。

　　本實驗使用三頸圓底玻璃瓶為反應器，加入適量之反應物、去離子水、有機溶劑、氫氧化鉀和觸媒以進行反應，藉由改變各種反應參數，如攪拌速率、水量、有機溶劑量、觸媒量、有機溶劑之種類、相間轉移觸媒之種類、鹼濃度、鹼種類、反應物比例、反應溫度及超音波功率，進行反應動力學之探討，藉由高效能液相層析儀（HPLC）、氣相層析質譜分析儀（GC/MS）、核磁共振儀（NMR）和元素分析儀（EA）分析其結果，以找出最適反應條件。

　　本實驗結果顯示（a）此反應為SN2取代反應（b）利用擬穩定狀態理論（pseudo steady-state hypothesis）與雙膜理論（two-film theory）可成功地推導出反應機制之擬一次數理模式（c）相間轉移觸媒技術可溫和且有效地加速反應，能夠避免在高溫時導致副反應之發生（d）活性觸媒之兩相質量傳送皆具有臨界值，顯示此反應系統為萃取反應機制，當攪拌速率高於臨界值時，為有機相化學反應控制（e）增加攪拌速率、反應溫度、觸媒用量與觸媒陽離子之親油性均可促進反應進行（f）使用部份因素實驗法可以找出在此合成反應中之交互作用項，包含攪拌速率-鹼量、攪拌速率-溫度與觸媒量-鹼量等三項，其原因與活性中間體在兩相間的分配、黏度、表面張力與水合數目有關。

　　In this study, 1,2-bis(benzyloxy)ethane was synthesized by reacting benzyl bromide with ethylene glycol under phase transfer catalysis. In the experiment, the reactor was a 100 mL three-necked flask, added an appropriate amount of reactant, deionized water, organic solvents, potassium hydroxide and the catalyst for reaction. Detailed investigation was made for: effect of agitation speed, amount of water, organic solvents, catalysts, organic solvent types, phase transfer catalyst types, alkali concentration, alkali salt type, mole ratio of reactant, temperature and ultrasonic wave. The reaction kinetics by high performance liquid layer chromatography (HPLC), gas chromatography mass spectrometer (GC / MS), nuclear magnetic resonance (NMR) and elemental analysis (EA) to analyze this results to find the optimal reaction conditions.

　　The results show that (a) The reaction type as an SN2 reaction. (b) The pseudo steady-state hypothesis and two-film theory are successfully applied to describe the reaction behaviors. (c) The reaction was effectively enhanced in the mild conditions via phase-transfer catalysis. The reaction via phase-transfer catalyst could avoid by-product was produce at higher temperature. (d) A threshold value of two-phase mass-transfer rate would exist in the phase transfer catalytic reactions. All reaction systems were identified as the extraction mechanism. The reaction was organic reaction controlled when the agitation speed was higher than the threshold value. (e) The reaction rate is increase with the increase in agitation speed, temperature, amount of catalyst and organophilicity of the active catalyst. (f) The significant binary interactions in affecting the reaction rate, agitation speed-amount of KOH , agitation speed-reaction temperature, and amount of PTC-amount of KOH, are found with using fractional factorial design method. The reasons for these interactions are : distribution and concentration of active catalyst, viscosity and surface tension of liquid, and hydration number of active catalyst.

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