臺灣博碩士論文加值系統

多元不飽和脂肪酸中的二十二碳六烯酸（docosahexaenoic acid，DHA）被證實具有多種生理功能，鮪鰹等魚類之眼窩脂肪中則發現含有高量的DHA。鮪魚為我國的大宗漁獲物，魚頭為加工後的廢棄物，本論文以鮪魚魚頭的眼窩脂肪為原料，以超臨界二氧化碳（SC-CO2）萃取其中富含DHA的油脂，並進一步與水煮法所得的魚油比較，以探討兩者之油脂品質與儲藏安定性。
鮪魚眼窩脂肪組織之主要成分為水分（40.99-42.93％）、粗脂肪（46.24-49.24％）、粗蛋白（7.82-8.78％）和灰份（0.72-0.9％）。鮪魚眼窩油中所含的多元不飽和脂肪酸佔總脂肪酸的40.06％；而DHA佔總脂肪酸的30.57％，為鮪魚眼窩油中含量最高的脂肪酸。
以水煮法萃取鮪魚眼窩粗油，其萃油率占原脂肪含量之56.65％。以SC-CO2萃取鮪魚眼窩油，在30℃-60℃的範圍內，定溫下，鮪魚眼窩油之萃出率隨壓力上升而增加，於4000psi 60℃時可達最大收率85.95％。低壓時（2000及2500psi），萃油率隨溫度之升高而下降，例如2000psi下，30、40、50、60℃的萃油率分別為41.66％、23.68％、8.07％、0.7％。高壓時（3000-4000psi），萃油率隨溫度之變化可分為兩個區間，在40℃-50℃的區間，萃油率隨溫度之上升而增加；其他溫度區間則與低壓時相似，萃油率隨溫度之上升而減少。
鮪魚眼窩脂肪組織中的DHA含量為16.52 g/100g oil（以Folch溶劑萃取），經水煮得到的鮪魚眼窩粗油中DHA僅為7.36（g/100g oil），其他脂肪酸也有含量降低的情形，且DHA收率只有25.24％。經去除雜質的精製油，其DHA含量可提高到14.14（g/100g oil），但是DHA的回收率也只能達到40.86％。在2000psi-4000psi，30℃-60℃下，SC-CO2萃取得到的鮪魚眼窩油中DHA含量在13.12-21.18（g/100g oil）之間，甚至高於原料（眼窩脂肪）。不同SC-CO2萃取條件萃得的魚油其DHA含量並沒有顯著的差異。
水煮法粗油（含有1.23 mg/g的磷脂質）可不經脫膠步驟，而直接進行脫酸、脫色及脫臭。水煮粗油的酸價為0.96（mg KOH/g oil），過氧化價為19.93（meq/kg oil），經過精製後酸價為0.08（mg KOH/g oil），過氧化價為11.67（meq/kg oil）。鮪魚眼窩脂肪組織於SC-CO2萃取前磷脂質含量為1.76（mg/g），萃取後磷脂質已檢測不出，且鮪魚眼窩油的過氧化價會從萃取前的8.25（meq/kg oil）降至6.35（meq/kg oil），但是酸價卻會從0.8（mg KOH/g oil）上升到1.12（mg KOH/g oil）。
鮪魚眼窩油的萃取方法會影響所得油脂的儲藏安定性。於37℃避光透氧的儲藏試驗中，以SC-CO2萃取、水煮及水煮精製所得的鮪魚眼窩油其POV與TBA皆在第八天達到最大值，接著便開始下降。從POV與TBA上升的趨勢看來，油脂氧化安定性為水煮粗油的安定性最差，其次是以SC-CO2萃取的油，而水煮精製油最好。

Orbital adipose tissues of tunas (Thunnuss sp.) and bonitos (Auxis sp., Euthynnus sp. and Katsuwonus sp.) contain considerable quantities of docosahexaenoic acid (DHA) which was confirmed to have various beneficial physiological functions. Tuna is a major catch of marine fish in Taiwan and its head is a seafood processing waste. The objectives of this study were to extract the DHA-rich oil from tuna orbital adipose tissue with supercritical carbon dioxide (SC-CO2) and compare its oxidative stability with oil obtained from wet rendering of the tuna orbital adipose tissue.
The proximate composition of tuna orbital adipose tissue was moisture (40.99-42.93 %), crude fat (46.24-49.24 %), crude protein (7.82-8.78 %) and ash (0.72-0.9 %). Polyunsaturated fatty acids of tuna orbital adipose tissue constitute 40.06 % of the total fatty acids, and DHA is the most abundant one which constitutes 30.57 % of the total fatty acids.
The extracting yield of tuna orbital crude oil with wet rendering was 56.65 % of original lipid content. When extracting with SC-CO2 in the temperature range of 30~60oC, the extracting yield of tuna orbital oil increased with pressure at constant temperature, the maximum yield was 85.95 % at 4000 psi and 60 oC. At low pressures (2000 and 2500 psi), the yields of tuna orbital oil decreased with temperature. For example, at 2000 psi and 30、40、50 and 60 oC, the yields were 41.66, 23.68, 8.07 and 0.7 %, respectively. At high pressure (3000~4000 psi), the changes of yields of tuna orbital oil with temperature can be divided into two regions. At the region of 40~50oC, the extracting yields of tuna orbital oil increased with temperature; while at other temperature regions, the yields followed the same trend as low pressure conditions that is yields decreased temperature.
The DHA content of tuna orbital adipose tissue was 16.52 g/100g oil (determined by Folch method). With wet rendering, the DHA content of tuna orbital adipose tissue decreased to 7.36 (g/100g oil) and the yield was only 25.24 %, other fatty acids also decreased. The DHA content of refined wet-rendered oil raised to 14.14 (g/100g oil) due to the removed of impurities, however the recovery of DHA only raised to 40.86 %. In the SC-CO2 extraction of tuna orbital oil, the yields of DHA content were 13.12~21.18 (g/100g oil), even higher than the raw material (tuna orbital adipose tissue). There were no significant difference in DHA content at different conditions of SC-CO2 extraction.
Crude oil from wet rendering (phospholipid content was 1.23 mg/g oil) can be directly refined by alkali refining、bleaching and deordorization without degumming. The acid value (AV) of crude oil from wet-rendering was 0.96 (mg KOH/g oil) and peroxide value (POV) was 19.93 (meq/kg oil); after refining the AV was 0.08 (mg KOH/g oil) and POV was 11.67 (meq/kg oil). Before SC-CO2 extracting, phospholipids content was 1.76 (mg/g) and POV was 8.25 (meq/kg oil). After SC-CO2 extraction, phospholipids content was not detectable and POV decreased to 6.35 (meq/kg oil). But AV increased from 0.8 (mg KOH/g oil) before SC-CO2 extraction to 1.12 (mg KOH/g oil) after SC-CO2 extraction.
The extraction methods of tuna orbital oil could affect the oil storage stability. In the storage stability study at 37 oC under dark and in the pressure of oxygen, the POV and thiobarbituric acid (TBA) values of tuna orbital oil from SC-CO2 extraction, wet rendering without refining and wet rendering with refining all reached maximum value at 8 days, then slowed down. Judging from the increase trend of POV and TBA, the refined wet-rendered oil had the best storage stability, followed by SC-CO2 extracted oil. Crude wet-rendered oil had the least storage stability.

中文摘要Ⅰ
英文摘要Ⅲ
目錄Ⅴ
圖次IX
表次XI
壹、前言1
貳、文獻整理3
一、水產加工廢棄物之再利用3
（一）水產加工廢棄物之現況3
（二）魚油中多元不飽和脂肪酸DHA之簡介3
二、超臨界流體之簡介5
（一）超臨界流體之發展趨勢5
（二）超臨界流體之基本性質6
（三）超臨界二氧化碳之溶解度行為11
（四）溶質在超臨界流體中之相平衡量測及溶解度預測13
1. 狀態方程式17
2. 統計法18
3. 狀態方程式與統計法之比較19
（五）超臨界二氧化碳萃取在食品工業上之應用20
1. 咖啡與茶之咖啡因的去除21
2. 啤酒花苦味及香味成分萃取21
3. 香料及植物精油萃取21
4. 油脂的萃取純化21
（1）黃豆油脫膠與純化的應用22
（2）黃豆油脫酸及脫臭的應用22
5. 其他油脂之應用23
6. 天然色素萃取23
7. 膽固醇去除24
8. 酵素反應應用25
9. 機能性成分萃取25
三、魚油之萃取26
（一）一般方法26
（二）超臨界二氧化碳萃取法27
四、從水產油脂中濃縮三酸甘油酯型態之DHA28
（一）低溫溶劑區分法29
（二）酵素法29
（三）超臨界二氧化碳萃取法29
五、超臨界二氧化碳萃取對油脂氧化安定性之影響30
（一）不同操作條件（壓力溫度）超臨界二氧化碳31
（二）傳統萃取法與超臨界二氧化碳萃取法31
參、材料與方法33
一、實驗材料33
（一）原料（1）33
（二）原料（2）33
二、化學藥品34
三、儀器設備35
（一）超臨界二氧化碳萃取裝置35
（二）氣相層析儀37
（三）薄層層析-火焰離子化檢測器37
（四）示差掃描熱分析儀37
（五）掃描式電子顯微鏡37
四、本論文之實驗流程38
五、實驗方法39
（一）鮪魚眼窩脂肪之一般成分分析39
（二）油脂分析項目39
1.油脂氧化程度分析39
（1）酸價39
（2）TBA值39
（3）A26840
（4）過氧化價40
2.脂肪酸組成41
（1）酯化方法41
（2）脂肪酸定量之GC條件41
3.磷脂質含量分析42
（三）油脂萃取42
1.溶劑萃取法42
2.水煮法42
（1）水煮43
（2）脫酸43
（3）脫色43
（4）脫臭43
3.超臨界二氧化碳萃取法45
（1）以不同壓力及溫度條件萃取鮪魚眼窩脂肪45
（2）鮪魚眼窩脂肪溶解度計算與表示方法46
（四）掃描式電子顯微鏡47
（五）示差掃描熱分析47
六、統計分析47
肆、結果與討論48
一、鮪魚眼窩脂肪組織之一般成分分析48
（一）一般成分組成分析48
（二）脂肪酸組成48
（三）兩批原料之間的差異52
二、鮪魚眼窩油脂之萃取52
（一）水煮萃取52
1.水煮52
2.化學精製53
3.萃油率53
（二）超臨界二氧化碳萃取54
1.超臨界二氧化探萃取範圍之選定54
2.壓力溫度對萃出率之影響57
3.密度對萃出率之影響64
4.Chrastil方程式66
三、萃取方法對鮪魚眼窩油脂肪酸組成之影響66
（一）水煮法所得鮪魚眼窩油之脂肪酸組成66
（二）超臨界二氧化碳萃取法所得鮪魚眼窩油之脂肪酸組成70
（三）超臨界二氧化碳萃取條件對鮪魚眼窩油脂肪酸組成之影
響72
四、萃取方法對鮪魚眼窩油氧化安定性之影響72
（一）剛萃取出油脂之品質72
（二）37℃儲藏試驗下之氧化安定性80
1.過氧化物之測定80
2.紫外光268nm吸光值之變化80
3.TBA值之變化83
伍、結論89
陸、參考文獻90

＊ 小林猛。1989。超臨界流體抽出技術在食品加工的應用。食品之科學。1：101。
＊ 小竺原讓二。1987。利用超臨界流體萃取乾松魚之香味成份。 New Food Industry。 29(10)：13。
＊ 丹昭治。1988。以超臨界流體萃取分離機能性成份。食品之開發。23(3)：29。
＊ 永川真弓。1996。魚油の精製法法。日本公開特許公報。特開平8-311481。
＊ 永田年臣。1996。魚體からのDHA油の採油方法。日本公開特許公報。特開平8-157861。
＊ 矢澤一良。1994。EPAおよぴDHAの生產と利用。バイオサイエンスとイングサトリ一。52 (8) : 633。
＊ 矢澤一良。1997。DHAの機能研究最新動向。食品と開發。32(6) : 7.
＊ 安間哲男。1987。以超臨界氣體萃取分離及精製天然色素。食品工業。30(14)：45.
＊ 若林憲光。1987。超臨界流體萃取技術在食品工業之利用及裝置。New Food Industry。 29(10)：1。
＊ 家村芳次。1988。利用超臨界二氧化碳處理原料米。釀協。83(3)：154。
＊ 宮本浩士。高垣康幸。万倉三正。1997。高度不飽和脂肪酸含有油脂の濃縮方法。日本公開特許公報。特開平9-176678。
＊ 高橋昌一。1992。超臨界二氧化碳萃取技術在食品上的應用。New food industry。34(2) : 33。
＊ 新井邦夫。1987。超臨界流體溶劑在食品方面之應用。 New Food Industry。 29(10)：17。
＊ 德森恆雄。1997。高度不飽和脂肪酸含有油脂の過酸化物低減方法。日本公開特許公報。特開平9-202891。
＊ 德森恆雄。1997。高度不飽和脂肪酸含有油脂の濃縮方法。日本公開特許公報。特開平9-176678。
＊ 澤村正義、栗山敏直、李忠富、楠瀨博三。1989。以超臨界二氧化碳法及其他萃取法所得之柚皮精油成份比較。食品工業。36(1)：34。
＊ 王三郎。1996。水產資源利用學。台北，台灣。
＊ 王伯玲。1991。以超臨界二氧化碳萃取蒜油之研究。國立台灣大學食品科技研究所碩士論文。台北，台灣。
＊ 古國隆。1987。油脂區分與交酯化及米糠脂解脢之分離與純化。國立台灣大學農業化學研究所碩士論文。台北。台灣。
＊ 生物技術產業資訊叢書。1995。多元不飽和脂肪酸(DHA. EPA)市場概況。財團法人生物技術開發中心。
＊ 余哲仁。1996。利用超臨界二氧化碳為溶劑以酵素酯化反應製造高品味米酒及高粱酒之研究。行政院國家科學委員會專題研究計劃成果報告。計劃編號:NSC84-2321-B-021。台北，台灣。
＊ 余哲仁、詹國靖。1997。利用超臨界二氧化碳為溶劑以Candida Cylindracea脂解脢合成己酸乙酯之研究。中國農業化學會誌。35(4)：1。
＊ 吳清熊。1990。台灣水產加工現況。行政院農委會。
＊ 林志城。1992。魷魚內臟油氧化安定性之研究。國立台灣大學食品科技研究所博士論文。台北。台灣。
＊ 林河木。1994。超臨界流體在食品工業的應用。化工技術。41(4)：42。
＊ 林新發、廖俊雄、陳健忠、凌永健。1995b。超臨界流體萃取和潔淨技術（下）。 科儀新知。27(3): 82。
＊ 林新發、廖俊雄、陳健忠、凌永健。1995a。超臨界流體萃取和潔淨技術（上）。 科儀新知。27(2): 50。
＊ 金曉珍。1995。超臨界流體技術在食品工業應用之研究規劃報告。科學發展月刊。23：545。
＊ 姚俊旭、蔡繁男。1992。超臨界流體萃取技術。化工技術。39(6) : 56-66。
＊ 食品資訊。1994。 12:47。
＊ 孫璐西，廖怡禎。1998。超臨界流體技術在食品工業中之應用。化工技術。6(10): 148.
＊ 康素蓉。1989。魷魚內臟油於不同條件下之氧化作用。國立台灣大學食品科技研究所碩士論文。台北。台灣。
＊ 張汐。曹國鋒。1998。EPA和DHA的提取和富集 II.富集方法。中國油脂。23（1）60。
＊ 莊志仁。1992。以超臨界二氧化碳萃取豬油中之膽固醇。 國立台灣大學食品科技研究所碩士論文。台北，台灣。
＊ 陳東輝。1995。吳郭魚死後僵直中嫩化作用對肉品品質的影響。國立海洋大學食品科技研究所碩士論文。基隆。台灣。
＊ 陳重文。1996。以超臨界二氧化碳萃取法降低豬油中之膽固醇。國立台灣大學食品科技研究所博士論文。台北，台灣。
＊ 溫惠美，李敏雄。1995。利用脂解提高精緻魷魚油中EPA及DHA之含量。中國農業化學會誌。33(2):134。
＊ 彭清勇。阿根廷魷魚肝臟脂質安定性及揮發性化合物之變化。國立海洋大學食品科技研究所碩士論文。基隆。台灣。
＊ 萬荷青。1991。魷魚內臟油膠囊製品之安定性。國立台灣大學食品科技研究所碩士論文。台北，台灣。
＊ 葉安義。1998。超臨界萃取於食品之應用。化工技術。6(2)：113。
＊ 廖怡禎。1994。高壓二氧化碳萃取裝置之籌建。研究報告第83-876-4號。食品工業發展研究所。新竹，台灣。
＊ 廖怡禎。1997。參加第四屆超臨界流體技術國際會議報告，食品工業月刊。29(8)：51。
＊ 廖怡禎。1997。超臨界流體技術在台灣食品工業之發展與未來應用之展望。食品工業月刊。29(8) : 38。
＊ 漁業年報。1997。臺灣省政府農林廳漁業局。p.147。 台北，台灣。
＊ 潘日鴻。1997。高壓流體萃取分離紅辣椒辣味及色素。食品工業月刊。2: 17。
＊ 潘日鴻、廖怡禎。1996。高壓流體萃取及分離紅辣椒色素及辣味之研究。研究報告第85-1117號。食品工業發展研究所。新竹，台灣。
＊ Acman, R.G., Ratnayake and Macpherson, E.J. 1989. EPA and DHA contents of encapsulated fish oil products. JAOCS. 66(8): 1162.
＊ Allan, W.A. and Wood, H.L. 1970. J. Sci. Food Agric., 21, 282.
＊ Angus, S., Armstrong, B. and de Reuck, K.M. 1976. Carbon dioxide: international thermodynamics tables of the fluid state-3. Pergamon press, New York.
＊ AOAC. 1983. Official and tentative methods of the American Oil Chemistry Society. American Oil Society, Champaign, Illinois.
＊ Arai, K. 1997. New methods for separating and achieving high purity eicosapentaenoic acid and docosahexaneoic acid. The 27th Annual Meeting of the Chinese Institute of Food Science and Technology. Taipei, Taiwan.
＊ Arul, J., Boudreau A., Makhlouf, J., Tardif, R., and Shasrabudhe, M. R. 1987. Fractionation of Anhydrous Milk Fat by Supercritical Carbon Dioxide. J. Food Sci. 52(5): 1231.
＊ Bhaskar, A.R., Rizvi, S.S.H., and Sherbon, J.W. 1993. Anhydrous milk fat fractionation with continuous countercurrent supercritical carbon dioxide. J. Food Sci. 58(4) : 748
＊ Bimbo, A.P., 1998. Guidelines for charactering food-grade fish oil. INFORM. 9(5): 473.
＊ Bio Industry, 1996. Bio products-DHA. Bio Industry. 13(1): 75.
＊ Birtigh, A., Johannsen, M. and Brunner G., 1995. Supercritical-fluid extraction of oil-palm components. Journal of supercritical fluids. 8: 46.
＊ Bondioli, P., Mariani, C., Lanzani, A., Mossa, A. and Muller, A. 1992. Lampante oliver oil refining with supercritical carbon dioxide , JAOCS, 69(5): 477.
＊ Bondioli, P., Lanzani A., Muller A., Mariani C. and Fedeli E., 1993. Squalene recovery from olive oil deodorizer distillates , JAOCS, 70(8): 763.
＊ Bott, T.R., 1982. Fundamental of carbon dioxide in solvent extraction. Chemistry and Industry. 19: 394.
＊ Bringe, N. A., Clark, D.R., and Howard, D. B. 1996. Emusifying properties of low-fat, low cholesterol egg yolk prepared by supercritical/ sub CO2 extraction, Journal of Food Science, 61(1): 19.
＊ Bringe, N.,A. and Cheng, J., 1995, Low-fat, low-cholesterol egg yolk in food applications. Food Technology, 49(5): 94.
＊ Bringe, N.A., Howard, D.B. and Clard, D.R. 1996. Emulsifying properties of low-fat, low-cholesterol egg yolk prepared by supercritical CO2 extraction. J. Food Sci. 61(1): 19.
＊ Brogle, H., 1982. CO2 as a solvent: its properties and applications. Chemistry and Industry. 19: 385.
＊ Brunetti, L., Dghetta, A., Fedeli, E., Kikic, I. and Zanderighi, L. 1989. Deacidification of olive oil by supercritical carbon dioxide. JAOCS. 66(2): 209.
＊ Brunner, G., and Peter, S. 1982. On the solubility of glycerides and fatty acids in compressed gases in the presence of an entrainer. Separation Science and Technology. 17(1): 199.
＊ Calame, J.P. and Steiner, R. 1982. CO2 extraction in the flavour and perfumery industries. Chemistry and Industry. 19: 399.
＊ Calvo, L. Cocero, M. J. and Diez, J. M. 1994. Oxidative stability of sunflower oil extracted with supercritical carbon dioxide. JAOCS. 71(11): 1251.
＊ Catchpole, O. J., von Kamp J. C. and Grey J. B.. 1997. Extraction of squalene from shark liver oil in a packed column using supercritical CO2. In proceedings of the 4th International Symposium on Supercritical Fluids. B: 175-179. May 11-14, Sendai, Japan.
＊ Chang, S. S. 1988. Purification of fish oil. U.S. patent. 4874629.
＊ Chang, S. S., Vallese, F. M., Hwang, L. S., Hsieh, O. A. L. and Min, B. S. 1977. Apparatus for the isolation of trace volitale constituents from foods. J. Agric. Food Chem.25(3): 450.
＊ Chao, R. R., Huang, H. and Mulvaney S. J. 1993. Effects of extraction and fractionation pressures on supercritical extraction of cholesterol from beef tallow. JAOCS. 70(2): 139.
＊ Chimowitz, E.H., and Pennisi, K.J. 1986. Process synthesis concepts for supercritical gas extraction in the crossover region. AIChE J. 32, 1655.
＊ Chiou, R.Y.Y., Yu, Z.R., Wu, P.Y., Chen, W. and Weng, Y.M. 1996. Partial defatting of roasted peanut meals and kernels by supercritical CO2 using semicontinuous and intermittently depressurized processes. J. Agric. Food Chem. 44: 574.
＊ Cho, S. T., Miyashhita, K., Miyazawa, T., Fujimoto, K., and Kaneda, T. 1987. Autoxidation of ethyl eicosapentanoate and docosahexaneennoate under light irradiation. Nippon Suisan Gakkaishi. 53:813.
＊ Chrastil, J. 1982. Solubility of solids and liquids in supercritical gases. J. Phys. Chem. 86(15): 3016
＊ Christianson, D. D., Friedrich, J. P., List, G. R., Warner, K., Bagley, E. B., Stringfellow, A. C. and Inglett, G. E. 1984. Supercritical fluid extraction on dry-milled corn germ with carbon dioxide. J. Food Sci. 49:229.
＊ Christie, W.W. 1982. Lipid Analysis. 2nd ed. Pergamon Press. Great Britain, p53.
＊ Chun, M. K., Shin, H. S. and Lee, H. 1994.Supercritical fluid extraction of taxol and Baccatin III from needles of Taxus Cuspidata. Biotechnology Techniques. 8(8): 547.
＊ Cocero, M. J., and Calvo, L., 1996, Supercritical fluid extraction of sunflower seed oil with CO2- ethanol mixtures, JAOCS, 73(11): 1573.
＊ Coenen, H. and Kriegel, E. 1984. Applications of supercritical gas extraction processes in the food industry. Ger. Chem. Eng. 7:335.
＊ Cygnarowicz, W. L.1990. Design and control of a process to extract? Carotene with supercritical carbon dioxide. Biotechnol. Prog. 6: 82.
＊ Cygnarowicz-Provost, M. L., O''Brien, D. J., Maxwell, R. J. and Hampson, J. W. 1991. Supercritical fluid extraction of fungal lipids using mixed solvent. In Proceedings of the 2nd International Symposium on Supercritical Fluids. Boston Massachusetts, USA, 5:20.
＊ Daoud, I. S. and Kusinski, S. 1986. Process aspect of the extraction of hops with liquid carbon dioxide, J. Inst. Brew, 92: 559.
＊ Darrell, L.T. and Duane, K.L. 1995. Investigations into effect of supercritical carbon dioxide extraction on the fatty acid and volatile profiles of cooked chicken. J. Agric. Food Chem. 43: 2369.
＊ de Filippi, R. P. 1982. CO2 as a solvent: application to fats, oils and other materials. Chemistry and Industry 19:391.
＊ Dunford, N.T., Temelli, F. 1995. Extraction of phospholipids from canola with supercritical carbon dioxide and ethanol. JAOCS. 72(9): 1009.
＊ Dunford, N.T., Temelli, F. 1997. Extraction conditions and moisture content of canola flakes as related to lipid composition of supercritical CO2 extracts. J. Food Sci. 62(1): 1197.
＊ Dunford, N.T., Temelli, F. and Leblanc, E. 1997. Supercritical CO2 extraction of oil and residual proteins from Atlantic Mackerel(Scomber scombrus) as affected by moisture content . J. Food Sci. 62(2): 289.
＊ Dunford, N.T., Temelli, F., and Leblanc, E. 1997. Supercritical CO2 extraction of oil and residual proteins from Atlantic Mackerel (Scomber scombrus) as affected by moisture content. J. Food Sci. 62(2): 289.
＊ Duxbury, D. D. 1989. High-quality flavor & color extracts derived by supercritical extraction. Food Processing. 10: 50.
＊ Dziezak, J.D. and Editor, A. 1986. Innovative separation process finding its way into the food industry. Food Technol. 7: 66.
＊ Egan, H., Krik, R.S. and Sawyer., R. 1981. Pearson’s Chemical analysis of foods. Longman Sci. & Tech. P535.
＊ Eldridge, A.C., Friedrich, J.P., Warner, K. and Kwolek, W.F. 1986. Preparation and evaluation of supercritical carbon dioxide defatted soybean flakes. J. Food Sci. 51(3): 584.
＊ Erb, W. U. and Einstman, W. J., Decaffination process, US patent 3,989, 850.
＊ Fattori, M., Bulley, N. R. and Meisen, A. 1987. Fatty acid and phosphorus contents of canola seed extracts obtained with supercritical carbon dioxide, J. Agric. Food Chem. 35: 739.
＊ Fattori, M., Bulley, N.R. and Meisen, A. 1988. Carbon dioxide extraction of canola deed: oil solubility and effect of seed treatment. JAOCS. 65(6): 968.
＊ Favati, F., King, J. W., Friedrich, J. P. 1988, Supercritical/ Sub CO2 extraction of carotene and lutein from leaf protein concentrates. J. Food Sci. 53(5): 1532.
＊ Faviti, F., King, J.W. and Mazzanti, M. 1991. Supercritical carbon dioxide extration of evening primrose oil. JAOCS. 68(6): 422.
＊ Fillppi, R.P.D. 1982. CO2 as a solvent: Application to fat oil and other materials. Chemistry and Industry. 19: 390.
＊ Folch, J. Lee, M. and Staley, G. H. 1957. A simple method for the isolation and purification of total lipids from animal tissue. J. Biol. Chem. 226: 496.
＊ Francis, A. W. 1954. Ternary systems of liquid carbon dioxide. J. Phys. Chem. 58:1099.
＊ Friedrich, J. P., List, G. R. and Heakin, A. L. 1982. Petroleum-free extraction of oil from soybeans with supercritical CO2, JAOCS. 59(7): 288.
＊ Friedrich, J.P. 1982. Characterization of soybean oil extracted by supercritical carbon dioxide and hexane. J. Agric. Food Chem. 30: 192.
＊ Friedrich, J.P. and Pryde, E.H. 1984. Supercritical CO2 extraction of lipid-bearing materials and characterization of the products. JAOCS. 61(2): 223.
＊ Gardner, D. S. 1982. Industrial scale hop extraction with liquid CO2. Chemistry and Industry. 6: 402.
＊ Gardner, D.S. 1982. Industrial scale hop extraction with liquid CO2. Chemistry and Industry. 19: 402.
＊ Gersta, H., 1995. The use of n-3 PUFAs (fish oil) in enteral nutrition. Internat. J. Vit Nutr. Res. 65: 3.
＊ Gitterman, M., and Procaccia, I. 1983. Quantitative theory of solubility in supercritical fluids. J. Chem. Phys. 78: 2648.
＊ Goncalves, M., Vasconcelos, A. M., de Azvedo, P., Gomes, E. J. S., das Neves, Chaves, H. J. and da pante, M. N. 1991.On the application of supercritical fluid extraction to hedeacidification of olive oils. JAOCS. 68(7): 474.
＊ Gray, J. I. 1978. Measurement of lipid oxidation: a review. JAOCS. 55:539.
＊ Hamatani, K., Takahashi, M., Ogasahara, J. and Suitomo, S. I. 1991.Recovery of octacosanol with supercritical CO2 by the two stage separation on the commercial scale. In 2nd International Symposium on Supercritical Fluids. Boston Massachusetts. USA, 5:20.
＊ Hardardottir, I. and Kinsella, J. E. 1988. Extraction of lipid and cholesterol from fish muscle with supercritical fluids. J. Food Sci. 53(6): 1656.
＊ Hawthorne, S. B. and Miller, D. J. 1987. Extraction and recovery of polycyclic aromatic hydrocarbons from environmental solids using supercritical fluids. Anal. Chem. 59: 1705.
＊ Hierro, M. T. G., and Santa-Maria, 1992, Supercritical fluid extraction of vegetable and animal fats with CO2/sub. -- Mini Review, Food Chemistry, 45: 189.
＊ Huber, W.H., Molero, A., Pereyra, C., and Martinez de la Ossa E. 1996. Dynamic supercritical CO2 extraction for removal of cholesterol from anhydrous milk fat. International Journal of Food Science and Technology. 32: 143.
＊ Hudson, B. T. F. and Mahgoub, S. E. O. 1980. Naturally-occuring antioxidants in leaf lipid. J. Sci. Food Agric. 31:646.
＊ Hudson, B. T. F. and Mahgoub, S. E. O. 1981. Synergism between phospholipids and naturally-occuring antioxitants in leaf lipids. J. Sci. food Agric. 32:208.
＊ Hui, Y.U. 1996. Edible oil & fat products and application technology. Bailey’ s industrial oil & fat products, fifth edition, volume 3. John Wiley & Sons. Inc. Canada.p.225.
＊ Hung, T. V., and Unger, M. A. 1995. Cholesterol reduced egg yolk by supercritical fluid extraction. Food Australia. 47(5): 227.
＊ Hung, T.V. and Unger, M.A. 1994. Application of supercritical fluid extraction in Japanese food industry. Food Australia 46(5): 235.
＊ Hyatt, J. A. 1984. Liquid and supercritical carbon dioxide as an organic solvents. J. Org. Chem. 49:5097.
＊ Inomata, H., Kondo, T., Hirohama, S., Arai, K., Suzuki, Y. and Konno, M. 1989. Vapor-liquid equilibria for binary mixtures of carbon dioxide and fatty acid metyl esters. Fluid Phase Equilibria 46:41.
＊ Jarzebski, A. B. and J. J. Malinowski. 1995. Potentials and prospects for application of supercritical fluid technology in bioprocessing. Process Biochemistry. 30(4): 343.
＊ Jay, A. J., and Steytler, D. C. 1992. Nearcritical fluid as solvent for -Carotene. Journal of Supercritical Fluids, 5(4): 274.
＊ Jewell, N. E. and Nawar, W. W. 1980. JAOCS. 57(12): 398.
＊ Kamat, S., G. Critchley, E. J. Beckman, and Russell, A. 1995. Biocatalytic synthesis of acrylates in organic solvent and supercritical fluids:III. does carbon dioxide covalently modify enzymes. Biotechnology and Bioengineering. 46:610.
＊ King, J.W., Johnson, J.H., and Friedrich, J.P. 1989. Extraction of fat tissue from meat products with supercritical carbon dioxide. J. Agric. Food Chem. 3337: 951.
＊ Kinsella, J. E. 1988. Food lipids and fatty acids: Importance in food quality, nutrition, and health. Food Techonl. 42: 124.
＊ Kodama, K. and Yoshizawa, K. 1977. Sake. In Alcoholic Beverage. Academic Press, inc. p. 423
＊ Krukonis, V,J.,1984, Presented at the 77th Annual Meeting of the American oil chemists‘ society, Dallas, April 29-May 3.
＊ Krukonis, V., Brunner, G., and Perrut, M. 1994. Industrial operations with supercritical fluids: Current processes and perspectives on the future. In Proceedings of the 3rd International Symposium on Supercritical Fluids-Tome 1: Thermodynamics and Physico-Chemical Properties. France, 17-19 October.
＊ Lack, E. and Seidlitz, H. 1993. Commercial scale decaffeination of coffee and tea using supercritical CO2. In Extraction of Natural Products Using Near-Critical Solvents, Edited by King, M. B. and Bott, T. R., Chapman & Hall, London.
＊ Li, S., and S. Hartland. 1996. A new industrial process for extraction cocoa butter and xanthines with supercritical carbon dioxide. JAOCS. 73(4): 423.
＊ Liang, J. H. and Yeh. A. I. 1991. Process conditions for separating fatty acid esters by supercritical CO2. JAOCS. 68(9): 687.
＊ Lim, S. and Rizvi, S. S. H. 1995. Continuous Supercritical Fluid Processing of Anhydrous Milk Fat in a Packed Column. J. Food Sci. 60(5): 889.
＊ List, G. R., Friedrich, J. P. and Pominski, J. 1984. Characterization and processing of cottonseed oil obtained by extraction with supercritical carbon dioxide. JAOCS. 61(12): 1847.
＊ List, G. R., King, J. Johson, W.J. H, Warner K and Mounts, T. L. 1993. Supercritical CO2 degumming and physical refining of soybean oil. JAOCS. 70(5): 473.
＊ List, G.R. and Friedrich J.P. 1989. Oxidative stability of seed oils extracted with supercritical carbon dioxide. JAOCS. 66(1): 98.
＊ List, G.R. and Friedrich, J.P. 1985. Processing characteristics and oxidative stability of soybean oil extracted with supercritical carbon dioxide at 50 ℃ and 8000 psi. JAOCS. 62(1): 82.
＊ Margolis, G., Rushmore F. and Liu, T. S. Decaffeination of vegetable material, US patent 4,031, 251.
＊ Marsili, R., and Callahan, D. 1993. Comparison of a liquid solvent extraction technique and supercritical fluid extraction for the determination of alpha- and beta- carotene in vegetable, Journal of Chromatographic Science, 31(10): 422.
＊ Masayuki, T., Toshifumi, T., Hiroshi, M., Masahito, S. and Takeshi, K. 1987. Treatment of rice bran with supercritical carbon dioxide. Nippon Shokuhin Kogyo Gakkaishi 34(2): 102.
＊ McCue, N. 1995. Egg yolk without the cholesterol or fat, Prepared Food. 64(6): 137.
＊ McHugh, M. and Krukonis, V. 1986. Supercritical Fluid Extraction - Principles and Practice. Butterworths. Boston. USA.
＊ McHungh, M.A. and Krukonis, V.J. 1986. Supercritical fluid extraction: principle and practice. Butterworth pulishers.
＊ Mendes, R. L.,. Coelho, J. P., Carbral, J. M., Fernandes, H. L., Novais, J. M. and Palavra, A. F. 1995. Supercritical/sub CO2 extraction of carotenoids and other lipids from Chlorella vulgaris. Food Chemistry. 53(1): 99.
＊ Merkle, J.A. and Larick, D.K. 1995. Fatty acid content of supercritical carbon dioxide extraction of beef fat. J. Food Sci. 60(5): 959.
＊ Michihata, T., Sado, Y., Morita, Y. and Enomoto, T. 1997. Extraction of lipid from the residue of “IKA-ISHIRU” (squid fish sauce) using supercritical carbon dioxide. Nippon Shokuhin Kagaku Kogaku Kaishi. 44(11): 795.
＊ Mishra, V. K., Temelllli, F. and Ooraiikul, B. 1993. Extraction and purification of -3 fatty acids with an emphasis on superceitical fluid extraction - A review. Food Res. Int. 26:217.
＊ Moffat, C. F., McGill, A. S., Hardy, R., Anderson, R. S. 1993. The production of fish oils enriched in polyunsaturated fatty acid-containing triglycerides. JAOCS. 70(2): 133.
＊ Montanari, L., King, J.W., List, G.R. and Rennick, K.A. 1996. Selective extraction of phospholipid mixture by supercritical carbon dioxide and cosolvent. J. Food Sci. 61(6): 1230.
＊ Moyler, D. A. 1993. Extraction of flavor and fragrances with compressed CO2. In Extraction of Natural Products Using Near-Critical Solvent, Ed. King, M. B. And Bott, T. R., Champman & Hall. UK.
＊ Nakamura, K. 1994. Biological applications of supercritical fluid. In Proceedings of the 3rd International Symposium on Supercritical Fluids-Tome 3: Reaction. Material Science. Chromatography and Analytical SFE. France. 10:17.
＊ Nilsson, W. S., Gauglitz, E.J., Hudson, J.K., Stout, V. F. and Spinelli, J. 1988. Fraction of menhaden oil ethyl esters using supercritical fluid CO2. JAOCS. 65(1): 109.
＊ Ooi, C., Bhaskar, K.A., Yener, M.S., Tuan, D.Q. and Rizvi, S.S.H. 1996. Continuous supercritical carbon dioxide processing of palm oil. JAOCS. 73(2) : 233.
＊ Palmer, M. V. and Ting, S. S. T. 1995. Application for supercritical fluid technology in food processing, Food Chemistry. 52: 345.
＊ Palmer, M.V. and Ting, S.S.T. 1995. Applications for Supercritical Fluid Technology in Food Processing. Food Chemistry. 52. 345.
＊ Peng, D.-Y. and Robinson, D. B. 1976. A new two-constant equation of state. Ind. Eng. Chem. Fundam. 15(1): 59.
＊ Ramsay, M.E., Hsu, J.T., Novak, R.A. and Reightler, W.J. 1991. Processing rice bran by supercritical fluid extraction. Food Technol. Nov: 98.
＊ Rizvi, S.S.H. and Bhaskar, A.R. 1995. Supercritical fluid processing of milk fat : fractionation, scale-up, and economics. Food Technology. Feb: 90.
＊ Rizvi, S.S.H., Benado, A.L., Zollweg, J.A., and Daniels, J.A. 1986a. Supercritical fluid extraction: fundamental principles and modeling methods. Food Technology. 6: 55.
＊ Rizvi, S.S.H., Benado, J.A. and Daniels, J.A. 1986a. Supercritical fluid extraction: fundamental principles and modeling methods. Food Technol. 7: 55.
＊ Rizvi, S.S.H., Daniels, J.A., Benado, J.A. and Zollweg, J.A. 1986b. Supercritical fluid extraction: operating principles and food application. Food Technol. 7: 57.
＊ Roubal, W. L. 1967. JAOCS. 44(3): 325.
＊ Saito, S. 1995. Research activities on supercritical fluid science and technology in Japan-a review. The Journal of Supercritical Fluid. 8: 177.
＊ Sakaki, K., Yokochi,T., Suzuki,O. and Hakuda, T., 1990. Supercritical fluid extraction of fungal oil using CO2/sub, N2O/sub, CHF2/sub, and SF6/sub. JAOCS. 67(9): 553.
＊ Shishikura, A., Fujimoto, K., Kaneda, T., Arai, K. and Saito, S. Modification of butter oil by extraction with supercritical carbon dioxide. Agric. Biol. Chem. 50(5): 1209.
＊ Snyder, J. M., Friedrich, J.P. and Christianson, D. D.1984. Effect of moisture and particle size on the extractability of oils from seeds with supercritical CO2. JAOCS. 61 (12): 1851.
＊ Sperber, R. M., 1989, New technologies for cholesterol reduction. Food Processing. 11: 154.
＊ Stahl, E., Quirin, K.W. and Gerard, D. 1988. Dense gases for extraction and refining. Springer-Verlag, Berlin Heidelberg, Germany, P. 1.
＊ Stahl, E., Schutz, E. and. Mangold, H. K. 1980. Extraction of seed oils with liquid and supercritical carbon dioxide, J. Agric. Food Chem. 28: 1153.
＊ Taniguchi, M., T., Shibata, M. and Kobayashi,T. 1985. Extraction of oils from wheat germ with supercritical carbon dioxide, Agric. Biol. Chem. 49(8): 2367.
＊ Taylor, D.L. and Larick D.K. 1995. Volatile content and sensory attributes of supercritical carbon dioxide extracts of cooked chicken fat. J. Food Sci. 60(6): 1197.
＊ Temelli, F. 1992. Extraction of triglycerides and phospholipids from canola with supercritical carbon dioxide and ethanol. J. Food Sci. 57(2): 440.
＊ Temelli, F., Chen C. S. and Braddock, R. J. 1988. Food Technology, Jan: 145.
＊ Temelli, F., Leblanc, E., and Fu L. 1995. Supercritical CO2 extraction of oil from Atlantic Mackerel (Scomber scombrus) and protein functionality. J. Food Sci. 60(4): 703.
＊ Toshiaki O., 1998. Recovery and use of nutraceutical products from marine resources. Food Technology. 52(6): 50.
＊ Tsuda, T., Mizuno, K., Ohshima, K., Kawakashi, S., and Osawa, T., 1955. Supercritical carbon dioxide extraction of antioxidative components from tamarind (Tamarindus indica L.) seed coat. J. Agric. Food Chem. 43: 2803.
＊ Vega, P.J., Balaban, M.N., Sims, C.A., O’keefe, S.F. and Cornell, J.A. 1996. Supercritical carbon dioxide extraction efficiency for carotenes from carrots by RSM. J. Food Sci. 61(4): 757.
＊ Vollbrecht, R. 1982. Extration of hops with supercritical. Chemistry and Industry. 19: 397.
＊ Walsh, J.M., Ikonomou, G. D. and Donohou, M.D. 1987. Supercrutical phase behavior: The entrainer effect. Fluid Phase Equilibria. 33: 295.
＊ Wehling, R.L., Froning, G.W., Cuppett, S.L., and Niemann, L. 1992. Extraction of cholesterol and other lipids from dehydrated beef using supercritical carbon dioxide. J. Agric. Food Chem. 40: 1204.
＊ Wright, B.W., Wright, C.W., Gale, R.W. and Smith, R.D. 1986. Analytical supercritical fluid extraction of adsorbent materials. Anal. Chem. 59: 38.
＊ Yamaguchi, K. and Toyomizu, M. 1984. A role of phospholipid in antioxygenic action of lipids from the ordinary muscle of lean fish. Bull. Jpn. Soc. Sci. Fish. 50(11): 1897.
＊ Yamaguchi, K., Murakkami, M., Nakano, H., Konosu, S., Kokura, T., Yamamoto, H., Kosaka, M., and Hata, K. 1986. Supercritical carbon dioxide extraction of oils from Antarctic Krill. J. Agric. Food Chem. 34:904.
＊ Yeh, A.I., Liang, J.H. and Hwang, L.S. 1991. Separation of fatty acid esters from cholesterol in esterified natural and synthetic mixtures by supercritical carbon dioxide. JAOCS. 68(4): 224.
＊ Young, F.V.J., 1985, Fish oil bulletin 17, International Association of fish meal manufacturers, p94.
＊ Yu, Z. R., Rizvi, S. H.,and Zollweg, J. A. 1992. Enzymatic esterification of fatty acids mixtures from milk fat and anhydrous milk fat with canola oil in supercritical carbon dioxide. Biotechnology Progress. 8: 508.
＊ Yu, Z.-R., Singh, B., Rizvi, S. S. H. and Zollweg, J. A. 1994. Solubilities of fatty acids, fatty acid esters, triglycerides, and fats and oils in supercritical carbon dioxide. J. Supercrit. Fluids 7(1): 51.
＊ Zhao, W., Shishikura, A., Fujimoto, K., Arai, K. and Saito, S. 1987. Agric. Chem. 51(7): 1773.
＊ Zosel, K., 1979, Process for deorisation fats and oils, United States patent 4,156, 688 .