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研究生:黃昱源
研究生(外文):Yu-Yuan Huang
論文名稱:同步合成之含鉻金屬有機框架(Cr-MOF-199)及其孔洞衍生氧化銅/亞鉻酸銅複合物應用於提升酚羥化反應
論文名稱(外文):De novo synthesis of Cr-embedded MOF-199 and derived CuCr2O4/CuO porous composites for enhanced phenol hydroxylation
指導教授:吳嘉文吳嘉文引用關係
口試委員:陳俊維米澤徹溫政彥張瑋辰
口試委員(外文):Tetsu Yonezawa
口試日期:2016-05-30
學位類別:碩士
校院名稱:國立臺灣大學
系所名稱:化學工程學研究所
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:2016
畢業學年度:104
語文別:英文
論文頁數:98
中文關鍵詞:原位合成法金屬有機框架氧化銅亞鉻酸銅酚羥化金屬有機框架衍生複合物
外文關鍵詞:de novo synthesismetal organic frameworkscopper oxidecopper chromitephenol hydroxylationMOF-derived composites
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本研究目的是應用原位合成法(De novo synthesis)合成具孔洞之氧化銅/亞鉻酸銅複合物(CuCr2O4/CuO)應用於提升酚羥化 (hydroxylation)反應之選擇性。為了設計雙金屬固體催化劑,含銅之金屬有機框架(MOF-199)被選為裝載活性物質鉻之載體,並經由原位合成法同時組合鉻及載體。此鉻嵌入之金屬有機框架(Cr-MOF-199)被進一步燒成氧化銅/亞鉻酸銅複合物。此樣品並經由X光繞射(XRD)、掃描式電子顯微鏡(SEM)、穿隧式電子顯微鏡(TEM)及氮氣吸脫附進行分析。結果顯示,我們成功將鉻離子均勻嵌入金屬有機框架之中,其構型並隨著鉻含量的增加由八面體轉變為立方體。此具有孔洞之氧化銅/亞鉻酸銅複合物被進一步應用於酚羥化反應,並在最佳條件下有40%之二酚(diphenols)產率(包含鄰苯二酚及對苯二酚)。值得一提的是,由於亞鉻酸銅的存在,鄰苯二酚(catechol)及對苯二酚(hdroquinone)之間的選擇性(catechol/hydroquinone)由1.3增加至1.8。此應用氧化銅/亞鉻酸銅複合物提升酚羥化反應選擇性提供了金屬有機框架衍生觸媒(MOF-derived catalysts)全新的應用。

The purpose of this study is to synthesize porous copper chromite/copper oxide (CuCr2O4/CuO) composites by a de novo synthesis of Cr-doped metal organic framework (MOF) as effective catalysts for phenol hydroxylation with enhanced selectivity. To desgin and synthesize a bimetallic solid catalyst, MOF-199 with copper source was chosen as the support for incorporating active species (i.e. Cr) through a de novo synthesis route, i.e. chromium ions were encapsulated into MOF-199 simultaneously upon the formation of the MOF-199 framework. The obtained Cr-MOF-199 samples were further calcined to convert into CuCr2O4/CuO composites that were characterized with XRD, SEM, TEM, and nitrogen sorption. The results showed that chromium ions were successfully embedded in the structure of MOF-199 uniformly, and the morphology of Cr-MOF-199 was changed from octahedral to cubic when chromium content was increased. The obtained porous CuCr2O4/CuO composites were further applied in phenol hydroxylation, and the results showed a high yield of 40% for diphenols (including hydroquinone and catechol) in optimized reaction conditions. It is worth of noting that the ratio of catechol/hydroquinone was enhanced from 1.3 to 1.8 with the existence of our synthesized CuCr2O4/CuO composites. The enhanced selectivity of catechol in phenol hydroxylation catalyzed by our newly synthesized CuCr2O4/CuO composites would provide a new application of MOF-derived catalysts.

1. Introduction 1
2. Literature review 4
2.1. Support design 4
2.1.1. porous materials 4
2.1.2. metal organic frameworks (MOFs) 5
2.1.3. MOF-derived materials 7
2.2. Catalyst preparation 12
2.2.1. MOF composites31 12
2.2.2. post synthesis 14
2.2.3. in situ synthesis (de novo synthesis) 17
2.3. Catalysts for phenol hydroxylation 21
2.3.1. catalytic wet peroxide oxidation (CWPO) 21
2.3.2. phenol hydroxylation 22
3. Objectives 24
4. Experimental 26
4.1. Chemicals and materials 26
4.2. Equipments 26
4.3. Preparation of catalysts 27
4.3.1. Synthesis of MOF-199 27
4.3.2. De novo synthesis of Cr-MOF-199 28
4.3.3. MOF-derived catalyst by calcination 30
4.4. Hydroxylation reaction of phenol 33
4.4.2. Effectiveness of catalyst 37
4.5. Characterization of products 38
4.5.1. X-ray diffractometer (XRD) 38
4.5.2. Scanning electron microscope (SEM) 38
4.5.3. Energy dispersive spectroscopy (EDS) 38
4.5.4. Focused Ion Beam and Electron Beam System (FIB) 38
4.5.5. Scanning transmission electron microscope (STEM) 39
4.5.6. Energy-Dispersive X-Ray Fluorescence Spectrometer (XRF) 39
4.5.7. Inducyively Coupled Plasma-Mass Spectrometer (ICP/MS) 39
4.5.8. X-ray Photoelectron Spectroscopy (XPS) 39
4.5.9. Fourier Transform Infrared Spectrometer (FTIR) 40
4.5.10. Specific Surface Area & Pore Size Distribution Analyzer 40
4.5.11. Thermogravimetry/differential thermal analysis thermoanalyzer (TG-DTA) 40
4.5.12. High performance liquid chromatography (HPLC) 41
4.6. Analysis of reactions 41
5. Results and Discussions 42
5.1 Materials Characterizations 42
5.1.1 MOF-199 synthesis 42
5.1.2 Effect of embedded chromium 44
5.1.3 Effect of calcination 49
5.1.4 Effect of calcination temperature 62
5.1.5. Effect of synthetic temperature 70
5.2 Phenol Hydroxylation 74
5.2.1 Reaction optimization 74
5.2.2 Catalytic performance 82
6. Conclusion 87
7. Future Prospect 88
8. Reference 89
Appendix 96
A.1 ICP calibration curve of copper and chromium 96
A.2 calibration curve 97

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