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研究生：	陳冠霖 Chen, Guan-Lin
論文名稱：	蓖麻油脂化學品的製造與觸媒熱裂解蓖麻粕之研究 A Study on Oleochemicals Production from Castor Oil and Catalytic Pyrolysis of Castor Meal
指導教授：	吳文騰 Wu, Wen-Teng
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2013
畢業學年度：	101
語文別：	中文
論文頁數：	116
中文關鍵詞：	蓖麻、觸媒熱裂解、田口式實驗設計法、鹼裂解
外文關鍵詞：	Castor, Catalytic pyrolysis, Taguchi method, Alkali pyrolysis
相關次數：	點閱：96 下載：1
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蓖麻為世界十大油料作物之一，富含豐富的油脂稱為蓖麻油，蓖麻經過兩段式壓榨程序(冷壓榨、熱壓榨)之後約可得到50%蓖麻油與50%蓖麻粕，由於機械極限，蓖麻粕內仍殘留有相當的油脂，因此本研究主要分為兩個部分，第一部分則是利用鹼裂解法精煉壓榨蓖麻油為高單價之蓖麻油脂化學品(包含主產物癸二酸與副產物2-辛醇)，第二部分主要是利用觸媒熱裂解提取蓖麻粕內的剩餘油脂及提升熱裂解產物之品質。
在癸二酸的部分，本研究採用目前在工業上最廣泛被利用的鹼裂解蓖麻油製備法。主要探討鹼裂解溫度、反應時間與氫氧化鈉濃度對於蓖麻油脂化學品(癸二酸與2-辛醇)產量的影響。本研究在鹼裂解溫度300 oC、反應時間5小時、氫氧化鈉的濃度0.6 M下，可得74.3%理論產量的癸二酸與73.9%理論產量的2-辛醇。本研究並進一步對蓖麻油進行前處理(將蓖麻油預先與氫氧化鈉混合，設定在約80 oC下均勻攪拌)，發現經由24小時的前處理蓖麻油再進行鹼裂解反應，可將癸二酸的理論產量提升至79.1%，而副產物2-辛醇也隨之些微提升至75.2%。
在熱裂解的部分，本研究利用田口式實驗規劃法得知四種主要變數對於蓖麻裂解油生產量的影響程度，依序為氮氣流速、熱裂解溫度、滯留時間與升溫速率，並且獲得之最適操作條件為:熱裂解溫度400 oC、滯留時間120分鐘、升溫速率20 oC/min與氮氣流速200 mL/min下可得19.61% (g/g-castor meal)的蓖麻裂解油。本研究進一步利用氧化鋁與沸石ZSM-5為觸媒以提升熱裂解效率。實驗結果顯示，此兩種觸媒的添加，均會微幅降低蓖麻裂解油的產量。由熱分析、元素分析、GC/MS與黏度分析蓖麻裂解油，發現此兩種觸媒的添加均有助於促進蓖麻裂解油的加氫與除氧反應，使O元素以CO、CO2與H2O的形式被脫除。添加觸媒可降低熱裂解反應所需的活化能與蓖麻裂解油的黏度，提升熱裂解的反應速率、蓖麻裂解油的黏度指數與熱值，另外可催化蓖麻裂解油由較高碳數的化合物斷鍵為較低碳數化合物之組成，因此觸媒熱裂解有助提升蓖麻裂解油的品質。此外氧化鋁更有助於降低蓖麻粕熱裂解反應所需溫度，由339 oC降至284 oC。

Castor is one of the world’s top ten oil crops. Castor bean contains rich castor oil. After two stage pressing process (cold pressed and hot pressed), we can get 50% castor oil and 50% castor meal. However, castor meal still has residual oil due to the mechanical limitation. There are two parts in the study. The first part is to refine the pressed castor oil to high valuable products. The second part is to extract the residual oil from castor meal by thermal pyrolysis.
In the refinery of castor oil part, we use alkali pyrolysis to produce sebacic acid and accompanied byproduct 2-octanol. Effects of alkali pyrolytic temperature, reaction time and the concentration of sodium hydroxide on alkali pyrolysis are investigated. 74.3% of theoretical yield for sebacic acid and 73.9% of theoretical yield for 2-octanol are obtained by alkali pyrolysis under the conditions of 300oC temperature, 5 hours reaction time and the concentration of 0.6 M sodium hydroxide. Improving the pretreatment of alkali pyrolysis process(castor oil via 24 hours pretreatment then carry on alkali pyrolysis), it can increase the yield of olechemicals to 79.1% of theoretical yield for sebacic acid and 75.2% of theoretical yield for 2-octanol.
In thermal pyrolysis part, the Taghchi method is used to find the effects of different parameters on castor meal pyrolysis. The effective order of pyrolytic parameter is nitrogen flow rate> pyrolytic temperature> residence time> heating rate. The optimal conditions for the production of pyrolytic oil are: the pyrolytic temperature of 400 oC, the residence time of 120 minutes, the heating rate of 20 oC/min and the nitrogen flow rate of 200 mL/min. Therefore we can get the yield of 19.61% pyrolytic oil from the castor meal. Furthermore aluminum oxide, and zeolite ZSM-5 are also used as catalysts to study their effects on the thermal pyrolysis process. Aluminum oxide and zeolite ZSM-5 will slightly decrease the yield of pyrolytic oil. However from the experimental results of thermogravimetric analysis, GC/MS, elemental analysis and viscosity analysis, they are shown that catalysts can enhance the hydrogenation/deoxygenation reaction and make oxygen remove in the forms of CO、CO2 and H2O. The catalyst can decrease the activation energy and viscosity of pyrolytic oil. It can enhance pyrolysis reaction rate and increase viscosity index and calorific value of pyrolytic oil. The pyrolytic oil will be composed of lighter compounds. Therefore, catalytic pyrolysis can increase the quality of pyrolytic oil. In addition, aluminum oxide will decrease the pyrolysis temperature from 339 oC to 284 oC.

摘要.............................................................................................................................I
Abstract.....................................................................................................................III
誌謝............................................................................................................................V
目錄…………………………………………………………..…………................VI
圖目錄........................................................................................................................X
表目錄…………………………………………………........................................XIII
第一章 緒論..............................................................................................................1
1.1 前言..............................................................................................................1
1.2 研究動機與目的..........................................................................................3
1.3論文章節簡介 .............................................................................................5
第二章 文獻回顧 ....................................................................................................6
2.1 生物質與生質燃料......................................................................................6
2.1.1 木質纖維素........................................................................................8
2.1.2 纖維素................................................................................................9
2.1.3 半纖維素............................................................................................9
2.1.4 木質素..............................................................................................10
2.2 蓖麻與蓖麻相關衍生物............................................................................11
2.2.1 蓖麻..................................................................................................11
2.2.2 蓖麻油..............................................................................................16
2.2.3 蓖麻粕..............................................................................................18
2.2.4 蓖麻油脂化學品..............................................................................20
2.3 熱裂解........................................................................................................25
2.3.1 熱裂解原理......................................................................................25
2.3.2 熱裂解反應動力學..........................................................................32
2.3.3 觸媒反應機制..................................................................................35
2.3.4 觸媒熱裂解相關文獻回顧..............................................................38
2.4 田口式實驗設計法....................................................................................40
2.4.1 田口法簡介......................................................................................40
2.4.2 直交表..............................................................................................41
第三章 實驗材料與方法.........................................................................................43
3.1 實驗物料與藥品........................................................................................43
3.1.1 實驗物料..........................................................................................43
3.1.2 藥品..................................................................................................44
3.2 實驗儀器....................................................................................................45
3.3 實驗方法....................................................................................................48
3.3.1 蓖麻油脂化學品製造......................................................................48
3.3.2 觸媒熱裂解蓖麻粕..........................................................................49
3.4 分析方法....................................................................................................50
3.4.1 掃描式電子顯微鏡..........................................................................50
3.4.2 元素分析..........................................................................................50
3.4.3 熱重分析..........................................................................................51
3.4.4 傅立葉轉換紅外光光譜儀..............................................................52
3.4.5 氣相分析(質譜)儀..........................................................................52
3.4.6 動態流變儀......................................................................................52
3.4.7 電流勾錶訊號擷取..........................................................................53
第四章 結果與討論.................................................................................................55
4.1 蓖麻油脂化學品之製造..........................................................................55
4.1.1 癸二酸鑑定...................................................................................55
4.1.2 鹼裂解溫度對於蓖麻油脂化學品產量之影響...........................57
4.1.3 反應時間對於蓖麻油脂化學品產量之影響...............................59
4.1.4 NaOH濃度對於蓖麻油脂化學品產量之影響.............................60
4.1.5 蓖麻油前處理時間對於蓖麻油脂化學品產量之影響...............61
4.2 蓖麻相關衍生物之熱分析......................................................................63
4.2.1 蓖麻粕之熱分析...........................................................................63
4.2.2 蓖麻粕焦炭之熱分析...................................................................66
4.2.3 蓖麻裂解油之熱分析...................................................................67
4.3 蓖麻粕熱裂解參數討論與製程最佳化..................................................68
4.3.1 氮氣流速對於系統中蓖麻裂解油收集率之影響.......................68
4.3.2 蓖麻粕熱裂解操作參數之最佳化...............................................69
4.3.3 熱裂解溫度對於熱裂解蓖麻粕之影響.......................................74
4.3.4 熱裂解滯留時間對於熱裂解液體產量之影響...........................75
4.3.5 熱裂解電力成本估算...................................................................77
4.4 觸媒催化蓖麻粕熱裂解..........................................................................79
4.4.1 觸媒熱裂解蓖麻粕之熱分析.......................................................79
4.4.2 觸媒添加量對於蓖麻粕熱裂解產物的產量之影響...................82
4.4.3 觸媒熱裂解蓖麻粕對於反應活化能之影響...............................85
4.5 熱裂解產物分析......................................................................................88
4.5.1 蓖麻粕焦炭之表面結構分析.......................................................88
4.5.2 蓖麻裂解油之FTIR分析..............................................................89
4.5.3 蓖麻裂解油之成分分析...............................................................91
4.5.4 蓖麻油之黏度分析.......................................................................92
4.5.5 蓖麻粕焦炭與蓖麻裂解油之元素分析與熱值估計...................94
第五章 結論.............................................................................................................97
第六章 未來展望與建議.........................................................................................99
參考文獻.................................................................................................................100
附錄.........................................................................................................................106
附錄A 蓖麻粕熱裂解液體之GC/MS分析……………….......……………106
自述.........................................................................................................................116












圖目錄
圖1.1近十年原油價格之月比較趨勢圖(美金/桶) ................................................1
圖2.1主要熱化學轉換程序圖(包含中間產物與最終產物) ..................................7
圖2.2纖維素構造圖...................................................................................................9
圖2.3半纖維素構造圖...............................................................................................9
圖2.4構成木質素之苯基丙烷之化合物及其衍生物構造圖.................................10
圖2.5亞洲綠能公司高雄路竹 (Luchu, Kaohsiung)栽種基地所種植之蓖麻......12
圖2.6蓖麻籽.............................................................................................................13
圖2.7東、西印度蓖麻的栽種時程圖...........................................................................14
圖2.8蓖麻產業概況圖.............................................................................................15
圖2.9蓖麻油.............................................................................................................16
圖2.10蓖麻粕...........................................................................................................18
圖2.11蓖麻油鹼裂解成主產物癸二酸與副產物2-辛醇之反應示意圖...............22
圖2.12利用微波催化蓖麻油鹼裂解反應流程示意圖...........................................24
圖2.13有機物熱裂解反應三步驟...........................................................................26
圖2.14不規則斷鍵反應示意圖 (Random chain scission) ....................................27
圖2.15去聚合反應示意圖 (Depolymerization) ....................................................27
圖2.16脫取代基反應示意圖 (Elimination) ..........................................................27
圖2.17 環化反應示意圖 (Cyclization) .................................................................27
圖2.18交聯反應示意圖 (Crosslinking) .................................................................27
圖2.19熱裂解產物的應用示意圖...........................................................................31
圖2.20觸媒與非觸媒反應活化能階變化之比較圖...............................................35
圖2.21觸媒與非觸媒反應之轉化率比較圖...........................................................36
圖3.1冷壓榨蓖麻油.................................................................................................43
圖3.2亞洲綠能公司提供之蓖麻粕.........................................................................43
圖3.3蓖麻油脂化學品製備系統裝置圖.................................................................45
圖3.4熱裂解系統裝置圖.........................................................................................45
圖3.5 PID控制器.....................................................................................................46
圖3.6高溫烘箱.........................................................................................................46
圖3.7電流勾錶.........................................................................................................47
圖3.8微電腦精密酸鹼度測量計.............................................................................47
圖3.9氣相層析儀.....................................................................................................47
圖3.10皂化物中和與酸化示意圖...........................................................................48
圖3.11蓖麻熱裂解實驗流程圖...............................................................................49
圖3.12 TGA串聯FTIR裝置圖................................................................................51
圖3.13動態流變儀 (a)儀器裝置 (b)椎板流變儀示意圖 (c)震盪原理示意圖...53
圖3.14高溫裂解爐之電流訊號圖...........................................................................54
圖4.1癸二酸樣品與標準品之FTIR光譜分析.......................................................55
圖4.2癸二酸樣品與標準品之GC分析 (a)癸二酸標準品 (b)實驗樣品.............56
圖4.3鹼裂解溫度對於蓖麻油脂化學品產量之影響 (固定反應時間為5小時、  
      NaOH濃度為0.5 M) ...............................................................................57
圖4.4鹼裂解反應時間對於蓖麻油脂化學品產量之影響 (固定鹼裂解溫度為
      300 oC、NaOH濃度為0.5 M) ..................................................................59
圖4.5氫氧化鈉濃度對於蓖麻油脂化學品產量之影響 (固定鹼裂解溫度為300 
      oC、反應時間5小時) ...................................................................................60
圖4.6蓖麻粕之熱分析(升溫速率：10 oC) .............................................................63
圖4.7蓖麻粕TGA-FTIR分析.................................................................................64
圖4.8蓖麻粕焦炭之熱分析(升溫速率：10 oC) .....................................................66
圖4.9蓖麻裂解油之熱分析(升溫速率：10 oC) .....................................................67
圖4.10氮氣流速對於系統中蓖麻裂解油收集率之影響 (固定在熱裂解溫度300 
       oC、升溫速率20 oC/min與滯留時間30min) ............................................68
圖4.11蓖麻粕熱裂解操作參數之S/N反應圖........................................................72
圖4.12熱裂解溫度對於蓖麻粕熱裂解產物的產量之影響...................................74
圖4.13熱裂解滯留時間對於熱裂解液體獲取率之影響.......................................76
圖4.14三種不同熱裂解溫度下熱裂解之累積電力消耗.......................................77
圖4.15觸媒催化蓖麻粕的熱裂解之熱分析 (觸媒添加量：25 wt.%) ..................79
圖4.16比較熱裂解蓖麻粕添加氧化鋁觸媒之TGA-FTIR分析 (a)未添加觸媒之
       蓖麻粕 (b)添加氧化鋁為觸媒之蓖麻粕..................................................80
圖4.17比較熱裂解蓖麻粕添加沸石ZSM-5觸媒之TGA-FTIR分析 (c)未添加
       觸媒之蓖麻粕 (d)添加沸石ZSM-5為觸媒之蓖麻粕.............................81
圖4.18觸媒沸石ZSM-5的添加量對於熱裂解產物的產量之影響......................82
圖4.19觸媒氧化鋁的添加量對於熱裂解產物的產量之影響...............................83
圖4.20 ln(*dx/dT)與1/T線性廻歸關係圖............................................................86
圖4.21蓖麻粕焦碳之SEM表面結構分析 (x1000) (a)未經熱處理 (b)熱裂解溫
       度350 oC (c)熱裂解溫度550 oC (d)熱裂解溫度750 oC...........................88
圖4.22蓖麻裂解油之FTIR光譜分析.....................................................................89
圖A.1 水相蓖麻熱裂解液體之GC/MS分析.......................................................106
圖A.2蓖麻裂解油之GC/MS分析........................................................................107
圖A.3 蓖麻裂解油(w./5wt.% Al2O3)之GC/MS分析...........................................110
圖A.4蓖麻裂解油(w./5wt.% Zeolite ZSM-5)之GC/MS分析..............................113




表目錄
表1.1蓖麻與痲瘋樹之比較表...................................................................................3
表2.1不同生物質之木質纖維素含量比較表...........................................................8
表2.2蓖麻毒蛋白與其他三種毒性物之毒性比較表.............................................12
表2.3蓖麻粕的成分組成表.....................................................................................19
表2.4印度蓖麻粕產量表.........................................................................................19
表2.5癸二酸的物化性質表.....................................................................................21
表2.6熱裂解模式分類表.........................................................................................25
表2.7熱裂解反應過程.............................................................................................28
表2.8裂解油之有機化合物的組成表.....................................................................29
表2.9蓖麻籽裂解油主要成分表.............................................................................32
表2.10異相催化反應之相組合表...........................................................................37
表2.11 L8(27) 直交表...............................................................................................42
表4.1蓖麻油前處理時間對於蓖麻油脂化學品產量之影響(固定在最適操作條
      件：鹼裂解溫度為300 oC、反應時間5 小時、NaOH的濃度為0.6  
      M) .............................................................................................................62
表4.2熱裂解氣體特殊官能基位置與其對應化合物.............................................65
表4.3蓖麻粕熱裂解控制因子與其水準.................................................................69
表4.4 L9(34)直交表與其實驗配置..........................................................................70
表4.5蓖麻粕熱裂解之蓖麻裂解油獲取量之實驗數據及S/N比紀錄表.............71
表4.6蓖麻粕熱裂解操作因子之各水準對S/N比之反應表.................................71
表4.7田口最佳化之預測理論值與實驗值比較表.................................................73
表4.8三種不同熱裂解溫度下熱裂解單位蓖麻粕的能量消耗量.........................78
表4.9觸媒熱裂解對於反應活化能之影響表.........................................................86
表4.10蓖麻裂解油FTIR分析與其對應官能基.....................................................90
表4.11蓖麻裂解油之碳數分析表...........................................................................91
表4.12蓖麻壓榨油與蓖麻裂解油黏度分析...........................................................93
表4.13蓖麻粕焦炭之元素分析與熱值估算...........................................................94
表4.14蓖麻裂解油之元素分析與熱值估算...........................................................95
表A.1 水相蓖麻熱裂解液體之組成....................................................................106
表A.2 蓖麻裂解油之組成....................................................................................107
圖A.3 蓖麻裂解油(w./5wt.% Al2O3)之組成........................................................110
表A.4 蓖麻裂解油(w./5wt.% Zeolite ZSM-5)之組成..........................................113

                                    

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