||DEVELOPMENT OPTIMIZATION OF ULTRASOUND-ASSISTED OXIDATIVE DESULFURIZATION OF PYROLYSIS OIL FROM WASTE TIRE
||Department of Resources Engineering
近年來隨著科技進步，經濟快速成長，伴隨著能源需求增加，以及全球化石類能源日漸耗竭，再生能源發展技術又面臨實用性及經濟成本考量等多項瓶頸在2008年中，原油價格曾經突破每桶 USD 150元。因此，如何將廢棄物資源化、能源化將更顯重要。世界各先進國家皆戮力於研發廢棄物資源再利用及技術產業化，如：以高分子廢棄橡、塑膠裂解再生燃油等。
本研究即以超音波氧化脫硫技術應用於廢輪胎熱裂解油之脫硫，以達成資源再利用及生產乾淨能源為目的，並結合超音波氧化技術、相間轉移技術及金屬觸媒氧化技術等進行熱裂解油脫硫試驗；初次研究結果顯示：裂解油經雙氧水超音波氧化脫硫試驗後，裂解油中含硫濃度從8800 ppm降低至6377 ppm，其脫硫效率僅為27.0%左右。若改變實驗控制參數，分別探討：1. 金屬催化劑對於氧化脫硫效益之影響：實驗結果顯示脫硫效率隨著催化劑添加量增加而提高；2. 超音波震盪時間之影響：裂解油在雙氧水超音波氧化脫硫效率隨時間增加而提高，反應時間為20分鐘時其脫硫效率達到最佳狀態。3. 極性氧化有機硫去除技術之影響：評估使用氧化鋁吸附方式脫硫與極性溶劑萃取方式脫硫，以氧化鋁吸附方式可達最佳脫硫效益。最後，以最佳化之研究參數進行脫硫試驗：裂解油經脫硫實驗後之含硫濃度為2800 ppm，脫硫效率則可達到68.2%；此外，脫硫後之油品，其含硫量皆達到我國針對柴油及燃料油訂定之總硫管制標準。因此，本研究證實超音波氧化脫硫技術加上氧化鋁吸附劑方式可有效達到熱裂解油資源化再利用之目的。
本研究亦發現Thiophene 在氧化脫硫方式中最難去除之有機硫。本研究利用超音波震盪時間差異，及不同TMC、PTA、及H2O2 添加量，並利用ANOVA統計檢定方式評估出嘗試找出對於Thiophene的最佳脫硫參數佳。最後最佳脫硫參數為Thiophene溶液:H2O2:PTA: TMC 為1:1.5:0.005:0.01 並且超音波震盪時間為 20 分鐘。
利用這最佳參數亦運用於Thiophene,Benzthiophener及Dibenzothiophene 混合溶液中，發現將近73.5% Thiophene, 89.9% benzothiophene,以及100% dibenzothiophene 被氧化。比較三種有機硫之物理特性可以發現:Thiophene之沸點及電子雲密度比其他的有機硫為低，低沸點容易造成反應時蒸發，低電子雲密度造成在氧化過程之中不易被氧化，因此造成脫硫效益不佳之原因。
In recent years, the increasing world population and rapid industrial development has increased the consumption of fossil fuel-derived oils. In response to the resulting exhaustion of fossil fuel energy, many countries around the world are investigating methods of waste energy recovery and reuse, including oil recovery from the pyrolysis process of waste tires. There are many different organic sulfur compounds in the recovered oil. Thiophene is considered as the most refractory organic sulfur compound in oxidative desulfurization. This study has executed the ultrasound assisted oxidative desulfurization (UAOD) process to optimize the thiophene oxidation under bench scale. Four control factors, including the duration effects of sonication time, and the amount effects of transition metal catalyst, phase transfer agent and hydrogen peroxide, were carefully examined. The best operation condition evaluated by the analysis of variance (ANOVA) was confirmed at volume ratio of thiophene solution and H2O2, PTA, and TMC at 1:1.5:0.005:0.01 in 20 minutes sonication time, where almost 73.5% of thiophene, 89.9% of benzothiophene, and 100% of dibenzothiophene were oxidized to their corresponding sulfones. Moreover, the electron density on the sulfur atom of various compounds and their oxidation rate constants, including thiophene, benzothiophene, dibenzothiophene, and their methyl-substituted derivatives, were also examined. The oxidative reactivity of sulfur compounds was increased with the increasing number of electron density on sulfur atom. Thiophene that is commonly considered to be more difficult to oxidize is attributed to the combination effect of low electron density of the sulfur atom and low boiling temperature under mild oxidation reaction
This study also investigates the efficiency of an ultrasound-assisted oxidative desulfurization (UAOD) process in sulfur reduction from diesel oil and the pyrolysis oil from waste tires treatment. The results indicate that the oxidation efficiency increases as the doses of transition metal catalyst are increased. Longer sonication time also enhances the oxidation process, apparently through the biphasic transfer of oxidants, which results in a high yield of organic sulfur oxidation products. The best desulfurization efficiency was 99.7% (2.67 ppm sulfur remaining) and 89% (800 ppm sulfur remaining) for diesel and pyrolysis oils, respectively, via a process executed by two UAOD units connected in series and combined with solid adsorption using 30 g of Al2O3 in 6 cm columns. These batch experiment results demonstrate clean waste energy recovery and utilization, while fulfilling the requirements of Taiwan EPA environmental regulations (sulfur concentrations less than 5000 ppm).
The objective of the present study is cost and benefit analysis of ultrasound assisted oxidative desulfurization continuous flow process removal of organic sulfur compounds form pyrolysis oil. Cost-benefit analysis (CBA) is useful for considering UAOD technology by consistently appraising proposals in terms of society’s total environmental and economic cost-benefits. Cost-benefit analysis were done with refer to two separate studies on removal of sulfur compounds which were one UAOD unit and two UAOD units connected in a series. Two methods were compared with regard to their cost and percentage in sulfur removal. According to the result of the comparison, cost per unit in one UAOD unit removal was calculated $0.132/L and the ratio of sulfur removal was 68%, whereas the two UAOD units connected in a series removal was $0.289/L and 90.91%. Therefore, it was seen that cost per unit in two UAOD units connected in a series and sulfur removal ratio were higher than one UAOD method. For the cost-benefits analysis, the optimum desulfurization efficiency was accomplished at 68.2% (2800 ppm sulfur left) for the pyrolysis oil with one UAOD unit in series and combined with solid adsorption under 6-cm columns with 30 g of Al2O3. The monetary value of the social benefits is around $742.328/day for one set of UAOD unit. The best gross income for desulfurized pyrolysis oil is$ 3236.4/day in Taiwan and $11076.3/day in the U.S.A.
The experimental ultrasound assisted oxidative desulfurization continuous flow process proposed in the present study appears to be an excellent solution to future environmental challenges that will soon be imposed by new regulations. Finally, the continuous flow was evaluated. The best economic benefits and the least risk were found with the UAOD continuous flow processes.
TABLE OF CONTENTS VIII
LIST OF FIGURES XII
LIST OF TABLES XIV
1. INTRODUCTION 1
1.1 Introduction 1
1.1.1 Environmental Policy 1
1.1.2 Environmental Concern 3
1.1.3 Environmental Regulation on Fossil Fuel 4
1.2 Desulfurization Techniques 6
1.2.1 Hydro-Desulfurization 6
1.2.2 Oxidative Desulfurization 8
1.2.3 Liquid-Liquid Extraction 11
1.2.4 Biodesulfurization 12
1.2.5 Ion-Ion Exchange 15
1.2.6 Adsorption for Sulfur Capture from Diesel Stream 15
1.3 Improvement Oxidative Desulfurization 18
1.3.1 Ultrasound-Assisted Oxidative Desulfurization 18
1.3.2 UAOD with Solid Absorption 19
1.4 Aims of the Research 21
2. THEORETICAL BACKGROUND 23
2.1 Introduction 23
2.1.1 Concept Model 24
2.1.2 Oxidants 26
2.1.3 Transition Mental Catalyst 27
2.1.4 Phase Transfer Catalysis 29
2.1.5 Ultrasound 30
3. UAOD Optimal Conditions for Model Sulfur Compounds 33
3.1 Introduction 33
3.2 Method and Analysis 36
3.2.1 Method 36
3.2.2 GC-SCD Quantitative Analysis 36
3.2.3 Statistic Analysis for Experimental Optimization 37
3.3 Result and Discussion 39
3.3.1 Duration Effect of Sonication Time 39
3.3.2 Amounts Effect of Transitional Metal Catalyst
3.3.3 Amounts Effect of Hydrogen Peroxide 41
3.3.4 Amounts Effect of Phase Transfer Agency (PTA) 42
3.3.5 Statistic Analysis of Optimized UAOD
Conditions for Thiophene 44
3.3.6 The Optimized UAOD Conditions applied to
Major Sulfur Compounds 45
3.3.7 Relationship between the Reactivity and Electron
Density on Sulfur Atom 46
3.4 Conclusion 51
4. The UAOD Optimal Conditions Appling into Diesel and
Pyrolysis Oil 53
4.1 Introduction 53
4.2 Method and Analysis 55
4.2.1 Materials 55
4.2.2 UAOD Methodology 56
4.2.3 GC-SCD Quantitative and Qualitative Analysis 59
4.3 Result and Disscussion 60
4.3.1 Characterization of Diesel and Pyrolysis Oils 60
4.3.2 Amount Effects of Transitional Metal Catalyst 62
4.3.3 Duration Effects of Sonication Time 66
4.3.4 Sulfone Separation Effects of Solvent Extraction
and SolidAdsorption after the UAOD Process 68
4.3.5 Effect of Continuous UAOD units Connected in
Series and Combined with Solid Adsorption 75
4.3.6 The quality analysis for desulfurized pyrolysis
4.4 Conclusions 81
5. Economic Analysis 82
4.1 Introduction 82
5.2 Method and Analysis 84
5.2.1 Economical Analysis 84
5.2.2 Risk Analysis 85
5.3 Result and Disscussion 86
5.3.1 Cost-Benefits Analysis 86
5.3.2 Risk Analysis for UAOD 93
5.4 Conclusions 99
6. SUMMARY AND RECOMMENDATION 100
6.1 Summary 100
6.2 Recommendation 104
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