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研究生:簡建仲
研究生(外文):CHIEN,CHIEN-CHUNG
論文名稱:中鏈結構脂質綠色合成程序:微波輔助程序之應用
論文名稱(外文):Green synthesis of medium-chain structural lipids using microwave-assisted non-catalytic process
指導教授:蘇家弘蘇家弘引用關係
指導教授(外文):SU,CHIA-HUNG
口試委員:傅俊中吳紹榮
口試委員(外文):FU,CHUN-CHONGWU, SHAO-JUNG
口試日期:2020-07-31
學位類別:碩士
校院名稱:明志科技大學
系所名稱:化學工程系碩士班
學門:工程學門
學類:化學工程學類
論文種類:學術論文
論文出版年:2020
畢業學年度:108
語文別:中文
論文頁數:86
中文關鍵詞:酯化反應自催化法微波輔助中鏈三酸甘油酯(中鏈結構脂質)綠色合成
外文關鍵詞:esterification reactionautocatalysis methodmicrowave-assistedmedium chain triglycerides(medium-chain structure lipids)Green synthesis
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綠色合成為有機化學合成面對新世代的學術前沿。
中鏈三酸甘油酯為碳鏈介於六至十二之間,存在於植物中的天然成分,在上世紀五十年代被引入到臨床領域,用來代替長鏈三酸甘油脂作為脂肪吸收障礙者的營養治療,半世紀以來,對於中鏈三酸甘油酯的理化性質、功能性質、代謝特性、營養藥理學以及營養生理學等特性研究深入,使得中鏈三酸甘油酯在食品、醫藥等諸多方面得到廣泛應用與發展。
當醇類與酸類進行化學反應時產生酯類與水,此反應稱為酯化反應,而反應過程中所添加觸媒種類,可分為化學催化法及酵素催化法,運用化學催化法時,所需時間較長在高溫度下反應,容易生成副產物且催化劑易溶於產物中,而酵素催化法的反應溫度較為溫和,但須克服缺點為酵素的高成本、低產率和反應時間長的問題。
本研究目的在運用微波加熱法,輔助月桂酸與丙三醇(甘油)進行酯化反應,在於無催化劑汙染產物、對環境友善度高,是符合綠色製程,其在恆壓狀態下以月桂酸及丙三醇莫耳比3:1探討影響反應因素為:反應溫度(140~220℃)、微波輻射功率(200~280W)、反應時間(60~140分鐘),最終以上列因子找到最適條件:反應溫度220℃、微波輻射功率280W、反應時間140分鐘,可達轉化率98%。
最後經由純化將產物過濾常溫乾燥,利用FTIR分析中鏈結構脂質,在3200~3500cm-1區間有強而寬的吸收峰為O-H鍵,經過酯化反應後此處的特徵峰逐漸消失不見,而在1050~1250cm-1的特徵峰為酯類上的C-O鍵,且在1735~1800cm-1的特徵峰為酯類上的C=O鍵,證明產物中存在著酯類生成。
使用熱重分析儀對中鏈結構脂質進行熱重及裂解溫度分析判斷,因中鏈結構脂質於324℃時開始裂解,而產物於317℃時開始裂解,接近中鏈結構脂質裂解溫度,因此證明產物中存有酯類的生成。
使用示差掃描熱量分析儀對中鏈結構脂質進行熔點溫度分析判定,而中鏈結構脂質熔點溫度在於48℃,且與產物相同,使其證明產物中具備酯類的生成。
Green synthesis is the academic frontier of organic chemical synthesis facing the new generation.
Medium-chain triglycerides are natural components with carbon chains between six and twelve, which exist in plants. They were introduced into the clinical field in the 1950s to replace long-chain triglycerides as fat absorption Nutritional treatment for people with disabilities. For half century, research on the physical and chemical properties, functional properties, metabolic properties, nutritional pharmacology and nutritional physiology of medium chain triglycerides has made medium chain triglycerides used in food and medicine. Many aspects have been widely used and developed.
When alcohols and acids undergo a chemical reaction, esters and water are produced. This reaction is called esterification. The types of catalysts added during the reaction can be divided into chemical catalysis and enzyme catalysis. When chemical catalysis is used, It takes a long time to react at high temperature, easy to produce by-products and the catalyst is easily soluble in the product, while the reaction temperature of the enzyme catalysis method is relatively mild, but the disadvantages problem of the high cost of enzymes, low yield and long reaction time must be overcome.
The purpose of this research is to use the microwave heating method to assist the esterification reaction of lauric acid and glycerol (glycerin). It is in line with the green process with no catalyst pollution products and also highly environmentally friendly. It uses lauric acid under constant pressure. And glycerol molar ratio 3:1 to explore the influencing factors: reaction temperature (140~220℃), microwave radiation power (200~280W), reaction time (60~140 minutes), and finally find the optimal conditions with the above factors :Reaction temperature 220℃, microwave radiation power 280W, reaction time 140 minutes, up to 98 % conversion.
Finally, the product was filtered and dried at room temperature through purification, and the medium-chain structure lipids was analyzed by FTIR. There is a strong and broad absorption peak in the range of 3200~3500cm-1, which is the O-H bond. After the esterification reaction, the characteristic peak here gradually disappears. The characteristic peak at 1050~1250cm-1 is the C-O bond on esters, and the characteristic peak at 1735~1800cm-1 is the C=O bond on esters, which proves that there is ester formation in the product.
Use a thermogravimetric analyzer to analyze the medium-chain structure lipids by thermogravimetry and cleavage temperature. Because the medium-chain structure lipids start to cleave at 270℃, and the product also starts to cleave at 270℃, it proves that there are esters in the product.
Differential scanning calorimetry was used to analyze the melting point temperature of the medium-chain structure lipids, and the melting point temperature of the medium-chain structure lipids was 48°C, which was the same as the product, which proved that the product had the formation of esters.
明志科技大學碩士學位論文指導教授推薦書 i
明志科技大學碩士學位論文口試委員審定書 ii
誌謝 iii
摘要 iv
Abstract vi
目錄 viii
圖目錄 xi
表目錄 xiii
符號表 xiv
第一章 緒論 1
1.1.前言 1
1.2.研究動機與目的 4
第二章 文獻回顧 5
2.1.綠色合成 5
2.1.1.原子經濟 6
2.1.2.有機電化學合成 8
2.1.3.溶劑 9
2.1.4.高效率合成方法 12
2.1.5.反應選擇性:定向合成 13
2.1.6.合成子與分子結構 13
2.1.8.安全化學品 14
2.2.中鏈脂肪酸定義 15
2.3.中鏈三酸甘油酯定義 17
2.4.中鏈脂肪酸/中鏈三酸甘油脂特質與製備相關資訊 18
2.4.1.理化特質 18
2.4.2.製備方法 18
2.4.3.分離純化 20
2.4.4.結構特性 24
2.5.酯化反應 28
2.6.酯類定義 30
2.7.酯化反應催化劑 31
2.8.合成方法 35
2.9.微波加熱介紹 40
2.9.1.微波特性 40
2.9.2.微波加熱技術發展概況 42
2.9.3.微波加熱原理 43
2.9.4.微波加熱優點 44
2.9.5.微波對化學領域及發展 46
第三章 實驗材料與方法 49
3.1.實驗材料 49
3.1.1.實驗儀器設備 49
3.1.2.實驗玻璃儀器 49
3.1.3.實驗藥品 51
3.2.實驗方法 52
3.2.1.月桂酸與丙三醇酯化反應 52
3.2.2.酯化反應流程 53
3.2.3.CEM聚焦式微波合成儀實際溫度校正 54
3.2.4.油脂之酸價測定與計算 54
3.2.5.脂肪酸轉化率計算 55
3.2.6.氣相層析儀(GC) 57
3.2.6.1.反應物與甘油酯鑑定 58
3.2.6.2.各成分之檢量線製作與分析 59
3.2.7.產品純化流程 62
3.2.8.傅立葉轉換紅外線光譜儀(FTIR) 63
3.2.9.熱重分析儀(TGA) 64
3.2.9.示差掃描熱量分析儀(DSC) 65
第四章 結果與討論 66
4.1.原子利用率證明 66
4.2.微波加熱與傳統加熱之差異 67
4.3.傳統加熱於不同溫度之影響 68
4.4.微波加熱於不同溫度之影響 69
4.5.微波加熱於不同功率之影響 70
4.6.GC分析產率 71
4.7.FTIR圖譜分析 73
4.8.TGA圖譜分析 76
4.9.DSC圖譜分析 78
第五章 結論 79
參考文獻 80

圖目錄
圖2-1 在人體中代謝過程 17
圖2-2 直接酯化法反應過程 19
圖2-3 酯交換法反應過程 19
圖2-4 酸解法反應過程 20
圖2-5 醇解法反應過程 20
圖2-6 分子蒸餾分離原理[47] 21
圖2-7 MCFA和LCFA的能量轉變模式 26
圖2-8 微波加熱示意圖 41
圖2-9 (a)傳統加熱與(b)微波加熱的差異[115] 47
圖3-1 各成分之分析圖譜 58
圖3-2 丙三醇之檢量線 59
圖3-3 月桂酸之檢量線 60
圖3-4 單月桂酸甘油酯之檢量線 60
圖3-5 雙月桂酸甘油酯之檢量線 61
圖3-6 中鏈結構脂質之檢量線 61
圖4-1 在不同加熱方式下轉化率與反應時間的關係曲線 67
圖4-2 不同溫度下轉化率與反應時間的關係曲線 68
圖4-3 不同溫度下轉化率與反應時間的關係曲線 69
圖4-4 不同功率下轉化率與反應時間的關係曲線 70
圖4-5 傳統加熱不同溫度下產率與反應時間的關係曲線 71
圖4-6 微波加熱不同溫度下產率與反應時間的關係曲線 72
圖4-7微波加熱不同功率下產率與反應時間的關係曲線 72
圖4-8 單甘油酯FTIR圖譜 74
圖4-9 雙甘油酯FTIR圖譜 74
圖4-10 中鏈結構脂質FTIR圖譜 75
圖4-11 純化後產物FTIR圖譜 75
圖4-12 純化後產物與標準品熱重分析 77
圖4-13 純化後產物與標準品外推裂解溫度分析 77
圖4-14 純化後產物與標準品熔點分析 78

表目錄
表2-1 MCT和LCT性質比較 27
表2-2 輻射類型和鍵能比較[112] 41
表2-3 微波應用 42
表2-4 傳統加熱與微波加熱的效果與區別 48
表3-1 本實驗使用之儀器設備 49
表3-2 本實驗使用之玻璃儀器 49
表3-3本實驗使用之藥品 51
表3-4 酸價分析之藥品配製與使用表 54
表4-1 FTIR官能基相關資訊 73
表4-2 TGA各裂解溫度 76
表4-3 各成分之熔點溫度 78
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