（1）離子液體應用於微藻油之萃取（2）高效能離子液體應用於纖維素溶解之研究（3）天然物吳茱萸次鹼之一鍋式合成研究

（1）Switchable Ionic Liquids for Microalgae Oil Extraction（2）Using Ionic Liquids for Dissolution of Cellulose（3）One-pot Synthesis of Rutaecarpine in Ionic Liquids

李欣怡(Hsin-Yi Li)

指導教授 ： 朱延和

國立中正大學/理學院/化學暨生物化學系/碩士(2013年)

摘要

第一章，離子液體應用於微藻油之萃取，主要於低耗能的實驗條件下，篩選出疏水性離子液體來有效以萃取方式從事微藻中之藻油提成。離子液體溶解油脂後再以二氧化碳進行化學反應改變其極性，達到油脂分離純化與離子液體的重複再使用，最後以氮氣下加熱去除二氧化碳（decarboxylation）或以酸水處理達回收離子液體之目的，以達到降低微藻產油過程中油脂萃取的成本。

第二章，高效能離子液體應用於纖維素溶解之研究，主要設計、合成與篩選出具有特定功能性的離子液體來有效以溶解方式從事纖維素之提成。藉由改變室溫型離子液體之陰陽離子組成與結構，以提升對纖維素的溶解度，最終以台灣鳳梨葉纖維及市售纖維素進行測試。

第三章，天然物吳茱萸次鹼之一鍋式合成研究，利用離子液體[b-3C-im][NTf2]經微波的條件下進行一鍋化反應，以市售的化學品為起始物，進行建構醯胺鍵與兩次合環反應，並大幅縮短反應時間，最終達到天然物吳茱萸次鹼及其衍生物之快速與有效合成。

關鍵字

天然物 ； 一鍋化 ； 溶解度 ； CO2反應 ； 離子液體

並列摘要

The first project—“switchable ionic liquids for microalgae oil extraction”—aimed at screening and identifying candidate water-immiscible, hydrophobic ionic liquids for effective extraction of microalgae oils. In our approach, ionic liquids were first employed to dissolve oils and subsequently carried out a carboxylation reaction with gaseous carbon dioxide to amend the overall polarity of ionic liquids to ultimately afford isolation and purification of oils. The recovery of ionic liquids was high and could be reused. These carboxylated ionic liquids could be conveniently decarboxylated upon bubbling with nitrogen gas under heated conditions and accordingly switched back to their original forms.

The second project—“cellulose dissolution in ionic liquids”—focused on the design, synthesis and screening of water-miscible functionalized ionic liquids with a specific aim for effective dissolution of cellulose. Based on reported literature, our research on cellulose dissolution was on imidazolium-based room-temperature ionic liquids such as [bmim][OAc] and [mEG1-mim][OAc]. Commercially available cellulose powder and fibrous cellulose from local pineapple leaf were used for all solubility tests.

The third project—“one-pot synthesis of rutaecarpine and its analogs in [b-3C-im][NTf2] ionic liquid”—specifically targeted the synthesis of rutaecarpine natural product in one-pot fashion. Our synthesis used commercially available and inexpensive reagents as starting materials, and was performed in ionic liquid by microwaves through sequential amide bond formation and concomitant construction of CD rings in one pot.

參考文獻

1. Wilkes, J. S. Green Chemistry 2002, 4, 73.

6. Hurley, F. H.; Wier, T. P. J. Electrochem. Soc. 1951, 98, 230.

8. Wilkes, J. S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1992, 965.

9. Davis, J. H.; Fox., P. A. Chem. Commun., 2003, 1209.

11. Yoshizawa, M.; Narita, A.; Ohno, H. Aust. J. Chem. 2004, 57, 139.