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研究生：	何國嘉 Ho, Kao-Chia
論文名稱：	以二階段酯化-轉酯化程序將高脂肪酸含量油品轉化為生質柴油 Conversion of free fatty acids-rich oil into biodiesel using a two-step catalytic esterification-transesterification process
指導教授：	張嘉修 Chang, Jo-Shu
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：	2014
畢業學年度：	102
語文別：	英文
論文頁數：	132
中文關鍵詞：	生質柴油、固態酸性觸媒、固態鹼性觸媒、廢食用油、析因設計法、二階段程序
外文關鍵詞：	biodiesel, solid acidic catalyst, solid alkaline catalyst, waste cooking oil, factorial designs, two-step process
相關次數：	點閱：103 下載：0
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本研究使用低成本、高自由脂肪酸(free fatty acids; FFAs)含量之廢食用油(waste cooking oil)為料源，進行生質柴油(biodiesel)之生產以降低生質柴油生產之成本。由於高FFAs含量會造成傳統轉酯化反應之問題，故本研究開發二階段程序進行生質柴油之製造，即先將油品進行酯化(esterification)步驟，在酸性觸媒的作用下，將脂肪酸與醇類反應並轉化為酯類，以達去除油品中游離脂肪酸之目的；接著，再進行轉酯化步驟，將油品中剩餘的三酸甘油酯(triglyceride)於鹼性觸媒的催化下，轉化為生質柴油。
本研究中所使用之酸性觸媒部份，首先合成以不同元素構成之金屬複合氧化物做為固體酸性觸媒之載體，於其上披覆二氧化矽後嫁接磺酸根以做為酸性官能基，並進行催化能力之測試與比較。其中以本實驗室自行開發之鍶鐵金屬複合氧化物為載體之觸媒(SO42-/Sr7Fe10O22)具有較佳之催化能力，該觸媒在100oC下反應60分鐘可使得油酸轉化率達98%以上。另外，該觸媒在重覆使用9次以後轉化率仍可達到79.5%以上。而鹼性觸媒部份，則以自行開發之固體鹼性觸媒矽酸鍶(Sr2SiO4)做為觸媒催化進行轉酯化反應，研究發現大豆油在30分鐘即可達92%的轉化率，若以氧化鍶(SrO)於相同反應條件及反應時間下進行轉酯化反應，僅能達到78%的轉化率，而氧化鈣(CaO)甚至幾乎沒有轉化率，可見相較於常見的氧化鈣以及氧化鍶，本實驗室自行開發之矽酸鍶有更加優異的催化能力。所合成的觸媒皆分別以氣體吸附比表面積測定儀(BET)、雷射光繞射儀(XRD)、掃描式電子顯微鏡(SEM)、能量散佈分析儀(EDX)、傅立葉轉換紅外線光譜儀(FT-IR)、熱重分析儀(TGA)、程式溫控脫附儀(TPD)及正丁胺滴定法(n-Butyl amine titration)進行分析，以了解其物理化學性質。
在二階段生質柴油生產程序方面，共使用兩種酸性觸媒與兩種鹼性觸媒進行最佳化程序之探討。首先以由大豆油與油酸組成之模擬油分別進行酯化以及轉酯化步驟的反應條件最佳化，並以析因設計法(The factorial designs)與操作成本進行反應條件之篩選，以獲得最佳的二階段程序反應條件。最後，在以模擬油測試完整程序之最佳化條件後，再實際以廢食用油進行驗證。結果顯示，在第一階段酯化反應時，以硫酸為觸媒的最佳化酯化反應條件為100oC反應60分鐘，而對於SO42-/Sr7Fe10O22而言則是100oC反應90分鐘。而在轉酯化步驟方面，氫氧化鈉與矽酸鍶之最佳反應條件均為60oC反應40分鐘。此外，不論使用模擬油或廢食用油來進行兩階段程序時，其生質柴油產率均能達到90%以上。

In this study, the low-grade oil source containing high free fatty acid content (such as waste cooking oil) to lower the cost of biodiesel production. Since the waste cooking oil used has high content of free fatty acids (FFAs) which cause problems on transesterification due to saponification that consumes alkaline catalysts with free fatty acids to form soap. As a consequence, a two-step process was developed to solve the problems resulting from FFAs in the oil used. This two-step process consists of sequential esterification and transesterification steps. As for acidic catalysts used for esterification, we first examined the catalytic performance of several self-developed solid acidic catalysts generated by graft acidic functional group on the different bivalent metal-based magnetic ferrites with silicon oxide shell. Strontium ferrite shows the best performance among all tested ferrites on the acidic catalyst preparation. Therefore, the strontium ferrite-based acidic catalyst (SFA) was selected to perform the esterification experiments. SFA could not only reach a FFA conversion of over 98% in 60 min of esterification, but also can be recovered easily by a magnet. A biodiesel production of 79.5% could be achieved after recycling the catalyst for 10 time. As for the alkaline catalyst used in transesterification, silicate strontium (Sr2SiO4) had an excellently catalytic reactivity, as a 92% triglyceride conversion could be reached in 30 min, suggesting that the Sr2SiO4 catalyst was much better for transesterification than commonly used CaO and SrO catalysts. On the two-step process, esterification and transesterification steps were performed separately to identify the optimum operating conditions by factorial designs with the consideration of the operating cost. After that, the two reactions were performed in series using simulated oil as feedstock to verify the obtained optimal operating conditions. Finally, waste cooking oil taken from a local stallman was used to perform an actual operation. The optimum conditions for esterification by sulfuric acid and SFA were at 100oC for 60 min and at 100oC for 90 min, respectively. In addition, the conversion of triglyceride was over 90% using both sodium hydroxide and Sr2SiO4 catalysts via transesterification reaction with an optimal condition of 60oC for 40 min regardless of oil sources used.

Abstract (摘要)	I
Abstract	III
Acknowledgement	V
Contents	VII
List of Tables	XI
List of Figures	XIII
Chapter 1	Introduction	1
1 Background	1
2 Motivation and purpose	2
3 The research scheme	3
Chapter 2	Literature Review	5
1 Biodiesel	5
2 Transesterification process to produce methyl esters	7
2.1 Background	7
2.2 Characteristics and the sources of raw materials	8
2.3 Waste cooking oil	9
3 Catalysis used for making biodiesel	11
3.1 Homogeneously base-catalyzed transesterification	19
3.2 Homogeneously acid-catalyzed transesterification	20
3.3 Homogeneously acid and base-catalyzed esterification and transesterification: two steps	25
3.4 Heterogeneously base-catalyzed transesterification	25
3.5 Heterogeneously acid-catalyzed transesterification	30
3.5.1 Zirconium oxide (ZrO2)	31
3.5.2 Titanium oxide (TiO2)	31
3.5.3 Tin oxide (SnO2)	32
3.5.4 Zeolites	32
3.5.5 Sulfonic ion-exchange resin	33
3.5.6 Sulfate modified meso-structural silica	33
3.6 Enzyme catalyzed transesterification	34
4 Magnetic supporter: ferrite	35
4.1 Structure of ferrite	35
4.2 Synthesis of ferrite	38
4.2.1 Conventional synthesis of ferrite: calcining	38
4.2.2 Non-conventional synthesis of ferrite	38
Chapter 3	Material and Methods	41
1 Material	41
2 Equipment	42
3 Analysis instrument	42
3.1 Measure surface area by BET	42
3.2 Structure analysis by X-ray diffraction (XRD)	43
3.3 Micrographics by scanning electron microscope (SEM)	44
3.4 Analysis elements of a sample by energy-dispersive X-ray spectroscopy (EDX)	45
3.5 Identify samples by Fourier transform infrared spectroscopy (FT-IR)	45
3.6 Weight loss examine by thermal gravimetric analysis (TGA)	46
3.7 Analysis of biodiesel conversion by gas chromatography (GC)	47
3.8 Strength of alkaline catalysts by temperature programmed desorption (TPD)	48
4 Analytical methods	49
4.1 Biodiesel conversion of esterification and transesterification analysis by GC	49
4.2 Determination of acidic active sites on the catalysts’ surface	50
4.3 The catalytic properties of the catalysts	51
5 Preparation of catalysts	51
5.1 Synthesis and decoration of magnetic supporter: ferrites	51
5.2 Synthesis strontium silicate as alkaline catalyst	52
6 Catalytic properties	54
6.1 Acidic catalysts for esterification	54
6.2 Alkaline catalyst for transesterification	54
6.3 Recovery of strontium ferrite after use	54
6.4 Surface modification of catalyst	55
7 Optimization and operational properties in the two-step reaction	55
7.1 Best individual operational conditions for esterification and transesterification	55
7.2 Examination of the two-step biodiesel production for simulated oil and waste cooking oil	56
Chapter 4	Solid Acidic Catalyst: Strontium Ferrite, Sr7Fe10O22	58
1 Effect of the compositions in the supporter on the catalytic reactivity	58
2 Effect of strontium content in the supporter on the catalytic reactivity	68
3 Effects of the amount of TEOS, the amount of sulfuric acid, and the calcination temperature on the catalytic reactivity	70
4 The catalytic properties of SO42-/Sr7Fe10O22	74
5 Regeneration of SO42-/Sr7Fe10O22	80
Chapter 5	Solid Alkaline Catalyst: Strontium Silicate	86
1 Process of making strontium silicate	86
1.1 The effect of the titration order in the precursor synthesis on catalytic reactivity of strontium silicate	86
1.2 The temperature program of calcination	87
2 Comparison of catalytic performance between strontium silicate (Sr2SiO4), calcium oxide (CaO), strontium oxide (SrO) and sodium hydroxide (NaOH)	90
3 Effect of strontium content in strontium silicate on transesterification	94
4 Repeated test of Sr2SiO4	96
Chapter 6	Optimization and Operating of Two-step Reaction	99
1 Waste oil simulation and catalyst selection	99
2 The factorial design	99
3 Optimization of esterification	101
4 Optimization of transesterification	105
5 Kinetics analysis of operational conditions	108
5.1 Kinetics of oleic acid esterification by using Sr7Fe10O22 as catalyst in a batch reactor	108
5.2 Kinetics of soybean oil transesterification by using Sr2SiO4 as catalyst in a batch reactor	112
6 Two-step biodiesel production in series	117
Chapter 7	Conclusions	124
References	126
                                    

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