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研究生：	吳俊毅 Wu, Chun-Yi
論文名稱：	以超臨界二氧化碳萃取海豹油之研究 Study on Extraction of Seal Oil with Supercritical Fluid Carbon Dioxide
指導教授：	葉茂榮 Yeh, Mou-Yung
學位類別：	碩士 Master
系所名稱：	理學院 - 化學系 Department of Chemistry
論文出版年：	2003
畢業學年度：	91
語文別：	中文
論文頁數：	110
中文關鍵詞：	海豹油、超臨界二氧化碳
外文關鍵詞：	seal oil, supercritical carbon dioxide
相關次數：	點閱：52 下載：2
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最近二十年來，醫學上開始注意和研究海豹油對人類的生長，健康以及疾病的影響和作用，包括在解決一些疑難病症中的功效。經過研究證明，海豹油中存在著大量的Omega 3脂肪酸，對防止和治療各種心腦血管疾病和高血壓病極有幫助，具營養滋補和醫用價值。一般來說富含多元不飽和脂肪酸的油脂通常對熱敏感，而且氧化安定性不佳，而超臨界二氧化碳的操作條件溫度適中且可避免氧化，為適合對多元不飽和脂肪酸之油脂加工。
本文研究分兩部分，第一部分是利用超臨界二氧化碳萃取技術處理海豹原油，希望能藉此達到精製海豹油之目的，並將超臨界二氧化碳精製之油品進行各項指標分析。結果顯示雖然萃出率很低，但經超臨界二氧化碳萃取所得的殘留油在脫酸及脫臭上卻具有一定的效果，在脫色上則無明顯效果。而在脂肪酸組成方面，經萃取的殘留油的脂肪酸組成與原油比較並無改變，但殘留油中DHA及EPA的含量均會較原油含量略為提高。所以超臨界二氧化碳萃取海豹油的確可以達到一定精製的效果。
第二部分為將海豹原油甲酯化，首先探討不同酯化條件對海豹油轉酯化率的影響，結果發現鹼催化比酸催化的能力佳，在反應時間三十分鐘即可達到最佳萃出率。接著以此方法將海豹油酯化後進行超臨界二氧化碳萃取，發現萃出率提高許多；在反應條件為溫度40℃、壓力4000psi、靜態萃取時間30分鐘及二氧化碳用量為200NL時，平均萃出率可達到32.43％，DHA含量有17.37 mg/g，EPA含量為10.28 mg/g。

During the past two decades people have become interested in the potential biological activity of seal oils in the body growth and health, including as medical drugs to cure diseases. Seal oils are rich in omega-3 type polyunsaturated fatty acid（PUFA）,which plays an important role in the prevention and as a potential drug to heart disease and hypertension .But the refinement of seal oils show some problems due to the potential oxidation of PUFA .The advantages of both operating at low temperature and anaerobic condition have made supercritical carbon dioxide（SC-CO2）tech- nology a very popular separation process.
The first purpose of this study was to refine the crude seal oil using SC-CO2 method .Crude oil was treated with SC-CO2 under various conditions. As the results it is effective in deacidifi- cation and deodorizerization. But it is not obvious in bleaching. The DHA and EPA content of the residual oil after SC-CO2 extraction was slightly higher than crude oil. This study showed that SC-CO2 refinement of seal oils had good oil quality and stability. The SC-CO2 extraction may have the potential as a refining process of the crude seal oil.
The second purpose was to extract the methylated seal oil by SC-CO2 .First we try to find the best transesterification process by changing different factors. Experimental results indicated base catalyst and the 30 min reaction time is the best process. Under the optimal conditions, at 40 ℃, 4000 psi and 30 min, there is the highest fatty acid methyl ester yield, and the DHA content is 17.37 mg/g, EPA content is 10.28 mg/g.

中文摘要--------------------------------------------------------------------- I
英文摘要---------------------------------------------------------------------II
目錄------------------------------------------------------------------------ IV
表目錄-----------------------------------------------------------------------IX
圖目錄------------------------------------------------------------------------X

第一章  緒論----------------------------------------------------------------- 1
第一節	前言---------------------------------------------------------------- 1
第二節	海豹簡介------------------------------------------------------------ 2
第三節  文獻整理------------------------------------------------------------- 4
一、油脂的成分----------------------------------------------------------------4
二、脂質在人體中的代謝------------------------------------------------------- 6
三、ω-3不飽和脂肪酸簡介------------------------------------------------------ 7
四、EPA與DHA之濃縮方法與技術簡介--------------------------------------------- 8
五、油脂精製過程-------------------------------------------------------------11
六、油脂品質之鑑定-----------------------------------------------------------13
第四節  超臨界流體之技術-----------------------------------------------------14
一、超臨界流體的簡介--------------------------------------------------------14 
二、影響超臨界流體萃取之因素-------------------------------------------------21
三、超臨界流體的發展與趨勢---------------------------------------------------24
四、超臨界二氧化碳萃取之溶解度行為------------------------------------------ 25
五、溶質在超臨界中的相平衡量測及溶解度預測-----------------------------------28
六、超臨界二氧化碳萃取在食品工業上的應用-------------------------------------33
七、超臨界二氧化碳萃取在分析化學上的應用------------------------------------38 
八、超臨界二氧化碳萃取在化學合成與製程上的應用-------------------------------38
九、超臨界流體在矽半導體工業之應用------------------------------------------40 
第五節  超臨界二氧化碳萃油行為 ---------------------------------------------40 
一、超臨界二氧化碳萃油行為---------------------------------------------------40
二、脫酸效果---------------------------------------------------------------- 41
三、脫色效果----------------------------------------------------------------42 
四、脫臭效果和氧化安定性----------------------------------------------------42 
五、脂肪酸組成--------------------------------------------------------------42
第二章  實驗裝置-------------------------------------------------------------44
第一節、超臨界流體萃取裝置--------------------------------------------------44 
一、流體來源----------------------------------------------------------------44 
二、高壓幫浦----------------------------------------------------------------44 
三、萃取槽------------------------------------------------------------------45
四、限流器------------------------------------------------------------------45
五、收集裝置----------------------------------------------------------------46
第二節、超臨界流體的萃取及分離方法----------------------------------------- 48
一、等溫法------------------------------------------------------------------48
二、等壓法------------------------------------------------------------------49
三、交錯區間分離法----------------------------------------------------------49
四、溫度梯度----------------------------------------------------------------49
五、壓力梯度----------------------------------------------------------------50
六、添加共溶劑--------------------------------------------------------------52
七、選擇性吸附法------------------------------------------------------------54
第三章  實驗內容------------------------------------------------------------55
第一節  實驗材料與試藥----------------------------------------------------- 55
一、原油--------------------------------------------------------------------55
二、藥品與溶劑--------------------------------------------------------------56
第二節  儀器設備------------------------------------------------------------57
一、超臨界二氧化碳流體萃取裝置----------------------------------------------57
二、減壓濃縮儀--------------------------------------------------------------57
三、氣相層析－質譜儀--------------------------------------------------------57
四、數據處理系統------------------------------------------------------------57
五、高感度色差計------------------------------------------------------------57
第三節  實驗流程設計--------------------------------------------------------57
第四節  實驗方法------------------------------------------------------------57
一、超臨界二氧化碳流體萃取法------------------------------------------------57
第五節  分析與數據統計----------------------------------------------------- 58
一、海豹油成分組成之分析----------------------------------------------------58
二、油脂氧化程度分析--------------------------------------------------------69
三、色澤分析----------------------------------------------------------------70
四、脫臭測試----------------------------------------------------------------70
五、甲酯化海豹油之製備------------------------------------------------------70
第四章  結果與討論----------------------------------------------------------72
  實驗第一部分--------------------------------------------------------------72
第一節  超臨界二氧化碳萃取法------------------------------------------------72
一、萃取溫度之影響----------------------------------------------------------72
二、萃取壓力之影響----------------------------------------------------------72
三、添加輔助溶劑之影響------------------------------------------------------73
四、靜態萃取時間的影響------------------------------------------------------73
五、脂肪酸分析--------------------------------------------------------------77
第二節  油脂品質分析--------------------------------------------------------80
一、酸價--------------------------------------------------------------------80
二、過氧化價----------------------------------------------------------------82
三、脫色分析----------------------------------------------------------------82
四、海豹油脫臭測試結果------------------------------------------------------82
第三節  討論--------------------------------------------------------------- 87
實驗第二部分----------------------------------------------------------------88
第一節  酯化反應的探討----------------------------------------------------- 88
第二節  超臨界二氧化碳萃取法------------------------------------------------90
一、萃取溫度之影響----------------------------------------------------------90
二、萃取壓力之影響----------------------------------------------------------90
三、靜態萃取時間的影響------------------------------------------------------93
四、二氧化碳用量的影響------------------------------------------------------93
五、脂肪酸甲酯分析----------------------------------------------------------96
六、最佳操作水準------------------------------------------------------------96
第五章  結論---------------------------------------------------------------100
參考文獻------------------------------------------------------------------ 101

表目錄
                                                                          頁次
表一  不同魚類其油中EPA及DHA含量之比較-------------------------------------- 9
表二  不同流體狀態下之基本物理性質------------------------------------------18
表三  不同超臨界流體之臨界溫度與壓力--------------------------------------- 22
表四  超臨界流體的工業運用------------------------------------------------- 26
表五  液態二氧化碳之溶劑性質----------------------------------------------- 27
表六  超臨界二氧化碳之優點------------------------------------------------- 32
表七  一次一變因法的因子與水準之設計----------------------------------------62
表八  海豹油脂肪酸組成------------------------------------------------------64
表九  脂肪酸甲酯標準品之檢量線--------------------------------------------- 68
表十  脫臭測試之實驗方法----------------------------------------------------71
表十一  海豹油脂肪酸含量----------------------------------------------------78
表十二  超臨界二氧化碳萃取海豹原油所得殘留油的脂肪酸組成--------------------79
表十三  原油及經不同脫臭測試所得的海豹油之味道品評--------------------------82
表十四  不同酯化條件及其萃取結果--------------------------------------------89
表十五  脂肪酸甲酯在超臨界二氧化碳不同條件下萃出之含量（一）----------------97
表十六  脂肪酸甲酯在超臨界二氧化碳不同條件下萃出之含量（二）----------------98
表十七  超臨界二氧化碳萃取海豹油甲酯之最佳水準----------------------------- 99

圖目錄
                                                                           頁次
圖一  海豹之圖片------------------------------------------------------------ 3
圖二  飽和與不飽和脂肪酸的結構-----------------------------------------------5
圖三  油脂自氧化作用之反應式----------------------------------------------- 15
圖四  測試過氧化價之反應式------------------------------------------------- 15
圖五  純物質之典型壓力-溫度相圖---------------------------------------------17
圖六  還原壓力與還原密度之關係圖------------------------------------------- 19
圖七  應用二氧化碳於不同溶合能力下，最適萃取目的之區域選擇------------------31
圖八  各種固定型限流計----------------------------------------------------- 47
圖九  可調整式限流器------------------------------------------------------- 47
圖十  交錯壓力與交錯區間示意圖--------------------------------------------- 51
圖十一  實驗流程圖--------------------------------------------------------- 59
圖十二  超臨界二氧化碳流體萃取裝置----------------------------------------- 61
圖十三  脂肪酸甲酯標準品層析圖--------------------------------------------- 65
圖十四  海豹油原油甲酯化之層析圖------------------------------------------- 66
圖十五  DHA與EPA之標準檢量線------------------------------------------------67
圖十六  不同溫度下之萃出率------------------------------------------------- 74
圖十七  不同壓力下之萃出率------------------------------------------------- 74
圖十八  改變輔助溶劑添加量對萃出率的影響----------------------------------- 76
圖十九  靜態萃取時間對萃出率的影響----------------------------------------- 76
圖廿    改變萃取溫度所得殘留油及原油的DHA、EPA含量--------------------------81
圖廿一  改變萃取溫度所得殘留油及原油的DHA、EPA含量------------------------- 81
圖廿二  超臨界二氧化碳殘留油與原油酸價之比較------------------------------- 83
圖廿三  超臨界二氧化碳萃出油與原油酸價之比較------------------------------- 83
圖廿四  經SC-CO2萃取之殘留油於4℃儲存六個月間酸價的變化並與原油比較-------- 84
圖廿五  改變壓力對過氧化價的影響並與原油比較------------------------------- 84
圖廿六  超臨界二氧化碳萃取後殘留油和原油在L、a、b值的關係圖-----------------85
圖廿七  不同溫度下之萃出率------------------------------------------------- 91
圖廿八  不同溫度下之DHA含量-------------------------------------------------91
圖廿九  不同溫度下之EPA含量-------------------------------------------------91
圖卅    不同壓力下之萃出率------------------------------------------------- 92
圖卅一  不同壓力下之DHA含量-------------------------------------------------92
圖卅二  不同壓力下之EPA含量-------------------------------------------------92
圖卅三  不同靜態萃取時間的萃出率------------------------------------------- 94
圖卅四  不同靜態萃取時間的DHA含量-------------------------------------------94
圖卅五  不同靜態萃取時間的DHA含量-------------------------------------------94
圖卅六  不同二氧化碳用量的萃出率------------------------------------------- 95
圖卅七  不同二氧化碳用量的DHA含量-------------------------------------------95
圖卅八  不同二氧化碳用量的DHA含量-------------------------------------------95
                                    

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