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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 戴子安(Chi-An Dai) | |
| dc.contributor.author | Li-Heng Chen | en |
| dc.contributor.author | 陳立恒 | zh_TW |
| dc.date.accessioned | 2021-06-16T17:54:18Z | - |
| dc.date.available | 2017-08-15 | |
| dc.date.copyright | 2012-08-15 | |
| dc.date.issued | 2012 | |
| dc.date.submitted | 2012-08-13 | |
| dc.identifier.citation | [1] Du Tingfa. Thermochimica Acta 1989, Pages 189–197.
[2] Baldwin, M. G. Reed, S. F. U.S. Pat. 3,881,969 (1975). [3] Combs, C. S.; Ashmore, C. I. U.S. Pat. 3,886,007 (1975). [4] Unver, Dilsiz, A. J. Appl. Polym. Sci., 96: 1654–1661 (2005). [5] Nielsen, A. T. U.S. Pat. 3,878,233 (1975). [6] Subramanian, K. J. Polym. Sci. A. 37. 4090–4099 (1999). [7] Grevels, F. W. Journal of Organometallic Chemistry 587 (1999) 122–126. [8] T.T. Nguyen. DSTO Aeronautical and Maritime Research Laboratory (1995) [9] Jean-Claude C. U.S. Pat. 4,668,313 (1987). [10] JOURNAL OF PROPULSION AND POWER Vol. 11, No. 4, July-August 1995. [11] Friedel, C.; Crafts, J. M. Compt. Rend. 1877, 84, 1392. [12] Takehiko Yamato, J Chieko Hideshima. J. Org. Chem. 1991, 56, 3955-3957. [13] G.A. Olah. Friedel–Crafts and Related Reactions. Wiley, New York, 1963–1964. [14] Bernard Chevrier. Angew. Chem. Internal. Edit. 1974. [15] Tadaaki Nakabayashi. J. Am. Chem. Soc. 1960, 82 (15), pp 3909–3913. [16] H. I. Schlesinger, Herbert C. Brown, A. E. Finholt, James R. Gilbreath, Henry R. Hoekstra, Earl K. Hyde. J. Am. Chem. Soc., 1953, 75 (1), pp 215–219. [17] Marshall, J. A.; Johnson, W. S. J. Org. Chem. 1963, 28, 421. [18] Hiyami, T. Comprehensive Organic Synthesis.; Pergamon: Oxford, England, 1991; Vol. 8, pp 763-792. [19] Wagner, G. H. U. S. Patent. No. 2,632,013, 1953. [20] Speier, J. L.; Webster, J. Journal of the American Chemical Society 1957, 79, 974. [21] H. Mimoun, J.Y. de Saint Laumer, L. Giannini, R. Scopelliti, C. Floriani, J. Am. Chem. Soc., 1999, 121, 6158–6166. [22] Harrod, J. F.; Chalk, A. J. Journal of the American Chemical Society 1964, 86, 1776. [23]. Tsipis, C. A. Journal of Organometallic Chemistry 1980, 187, 427 [24] Gustavo F.Organometallics, 2012, 31 (8), pp 3355–3360 [25] Ian Manners. Macromol. Chem. Phys. 2003, 204, 1259–1268. [26] Paloma Go´mez-Elipe. J. Am. Chem. Soc. 1998, 120, 8348-8356. [27] Alejandro Presa Soto. Ian Manners. Macromolecules 2009, 42, 40-42. [28] Martin Vogel, Marvin Rausch. J. Org. Chem., 1957, 1016. [29] M. A. Bazhenova, Ryabov, Russ. Chem.Bull., Vol. 45, No. I0, October, 1996. [30] J.C. Gautier and J.C. Mondet SNPE, Cenrre a’e Recherches du Bouchet, B.P. 2, 91710 Veti le Perir (France). [31] Sukanta Bhattacharyya, J. Chem. SOC.P, 1996, 1381. [32] Gordon W. Gribble, Department of Chemistry, New Hampshire 03755, USA Chemical Society Reviews, 1998,395. [33] PRADHAN, Braja Sundar WIPO Patent Application WO/2011/048615. [34] Polymer with ethylenic unsaturations incorporating silylmetallocene groups, patent number: 4,647,628, Mar. 3, 1987. [35] JOHN. L. SPEIERJ, A' MES A. WEBSTERA ND GARRETHT. BARNES, RECEIVEDA UGUST20, 1056, 974. [36] Bong-Sang Cho, Journal of Applied Polymer Science, 3560(2011). [37] 何明展,中原大學碩士論文 [38] D. Troegel, J. Stohrer / Coordination Chemistry Reviews 255 (2011) 1440. [39] J. C. Gautier and J. C. Mondet. Journal of Organometallic Chemistry, 452 (1993) 111-113. [40] John F. Garst. Inorganica Chimica Acta, 222 (1994) 365-375. [41] Min-Shiun Chao and Shih-Liang Huang Chemical Engineering Department, National Chin-Yi Institute of Technology, Taichung 41111, Taiwan, R.O.C. Journal of the Chinese Chemical Society, 2005, 52, 287. [42] 黃育群,中原大學碩士論文 [43] R MURALI SANKAR, SUBHADEEP SAHA, K SEENI MEERA and TUSHAR JANA, Bull. Mater. Sci, 2009, 507. [44] D. Saravanakumar. Journal of Applied Polymer Science, Vol. 119, 2517–2524 (2011) | |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/64555 | - |
| dc.description.abstract | Butacene是經由一連串反應製備而成的燃速調節劑，可以應用在固態複合推進器當作催化劑。本研究目的，我們利用 Friedel-Crafts反應乙醯化 ferrocene得到4-chlorobutyrylferrocene (4CByF)，由上述步驟產生的4CByF進行還原反應除去其中之C=O得到產物4-chlorobutyl ferrocene (4CBF)，將4-chlorobutyl ferrocene與鎂反應得到其Grignard reagent，此Grignard reagent與chlorodimethylsilane反應生成4-(ferrocenylbutyl) dimethylsilane，接著以 Pt為催化劑，將此ferrocene的矽烷衍生物接枝在HTPB側鏈雙鍵上，最終生成的產物即是我們想要的Butacene。將所得到的Butacene利用FTIR和NMR分析其結構及性質，其鐵含量則由thermogravimetric analysis (TGA) 量測，並與市售Butacene比較其差異性。 | zh_TW |
| dc.description.abstract | Butacene, which can be prepared in a series of reactions, has been used in solid propellant composite as a catalyst to control the burning-rate of a rocket. At first, we synthesized 4-chlorobutylferrocene by using Friedel-Crafts acylation of ferrocene followed by deoxigenation of the acylated ferrocene. The resulting 4-chlorobutylferrocene was to react with magnesium metal by using Grignard reaction to form a corresponding Grignard intermediate compound which can react with chlorodimethylsilane to produce 4-(ferrocenylbutyl) dimethylsilane. Ferrocenehydrosilane were added to the side chain double bonds of hydroxyl-terminated polybutadiene (HTPB) using hydrosilylation reaction with Pt as a catalyst to form 4-(ferrocenylbutyl) dimethylsilane-grafted HTPB, which is thus called Butacene. The structure of Butacene will be characterized by using FTIR and NMR. The iron content in the Butacene was verified by using thermogravimetric analysis (TGA) and found to be comparable to that of the commercial Butacene (SNPE) | en |
| dc.description.provenance | Made available in DSpace on 2021-06-16T17:54:18Z (GMT). No. of bitstreams: 1 ntu-101-R99524086-1.pdf: 2254624 bytes, checksum: d1ef716ec7e6c565e5c05011c92d7e2a (MD5) Previous issue date: 2012 | en |
| dc.description.tableofcontents | Content
致謝 I 摘要 III Abstract IV Content V Figure Caption VIII Table Caption XII Chapter 1 Introduction 1 1.1 Composite solid propellants 1 1.2 Butacene 2 2.1 Friedel-Crafts acylation 6 2.2 Deoxygenation 10 2.3 Hydrosilylation 13 Chapter 3 Experimental Parts 16 3.1 Experiment materials 16 3.2. Experiment Instruments 18 3.3 Synthesis procedures 21 3.3.1 Synthesis of 4-chlorobutyryl ferrocene 21 3.3.2 Analysis of 4-chlorobutyryl ferrocene 26 3.3.3 Yield of product: 26 3.3.4 Reaction mechanism: 26 3.4.1 Synthesis of 4-chlorobutyl ferrocene 33 3.4.2 Analysis of 4-chlorobutyl ferrocene 36 3.4.3 Yield of product: 36 3.4.4 Reaction mechanism: 36 3.5.1 Synthesis of 4-(dimethylsilyl)butylferrocene 41 3.5.2 Analysis of 4-(dimethylsilyl)butylferrocene 44 3.5.3 Yield of product: 45 3.5.4 Reaction mechanism: 45 3.6.2 Analysis of 4-(ferrocenylbutyl) dimethylsilane-grafted HTPB 54 3.6.3 Yield of product: 79 3.6.4 Reaction mechanism: 79 Chapter 4 Results and Discussion 80 4.1 Synthesis of 4-chlorobutyryl ferrocene 80 4.2 Synthesis of 4-chlorobutyl ferrocene 81 4.3 Simplify of the reaction process 82 4.3.1 One pot reaction 82 4.3.2 Synthesis process of one pot reaction 82 4.3.3 Analysis of 4-chlorobutyl ferrocene 83 4.4 Synthesis of 4-(dimethylsilyl)butylferrocene 86 4.5 Analysis of 4-(ferrocenyl butyl)dimethylsilane-grafted HTPB 87 4.5.3 FTIR analysis of 4-(ferrocenyl butyl)dimethylsilane-grafted HTPB 91 4.5.4 TGA analysis of 4-(ferrocenyl butyl)dimethylsilane-grafted HTPB 92 4.5.5 DSC analysis of 4-(ferrocenyl butyl)dimethylsilane-grafted HTPB 95 Chapter 5 Reference 102 Figure Caption Figure 1.1 Glass temperature for HTPB grafted with various hydrosilanes (a) (4' ferrocenyl methyl) phenyl dimethyl silane, (b) (3' ferrocenyl methyl) phenyl dimethyl silane, and (c) 4-ferrocenyl butyl dimethyl silane 4 Figure 1.2 Iron content vs percentage of modified double bonds of HTPB 5 Figure 3.1 1H NMR spectrum of 4-chlorobutyrylferrocene before recrystallization 28 Figure 3. 2 1H NMR spectrum of 4-chlorobutyrylferrocene after recrystallization 29 Figure 3.3 1H NMR spectrum of 4-chlorobutyryl ferrocene (in Ar) after recryllization 30 Figure 3.4 13C and DEPT 135 NMR spectrum of 4-chlorobutyryl ferrocene 31 Figure 3.5 FTIR spectrum of 4-chlorobutyryl ferrocene 32 Figure 3.6 1H NMR spectrum of 4-chlorobutyl ferrocene 38 Figure 3.7 13C and DEPT 135 NMR spectrum of 4-chlorobutyl ferrocene 39 Figure 3.8 FTIR spectrum of 4-chlorobutyl ferrocene 40 Figure 3.9 Before column chromatography of 4-(dimethylsilyl)butyl ferrocene 46 Figure 3.10 After column chromatography of 4-(dimethylsilyl)butyl ferrocene 47 Figure 3.11 13C and DEPT 135 NMR spectrum of 4-(dimethylsilyl)butyl ferrocene 48 Figure 3.12 FTIR spectrum of 4-(dimethylsilyl)butyl ferrocene 49 Figure 3.13 NMR spectrum of HTPB 56 Figure 3.14 NMR spectrum of French Butacene | |
| dc.language.iso | en | |
| dc.subject | 還原反應 | zh_TW |
| dc.subject | 佛瑞德－克來福特醯化反應 | zh_TW |
| dc.subject | 端羥基聚丁二烯 | zh_TW |
| dc.subject | 膠合劑 | zh_TW |
| dc.subject | 矽氫加成反應 | zh_TW |
| dc.subject | 矽烷化 | zh_TW |
| dc.subject | 格林鈉反應 | zh_TW |
| dc.subject | hydrosilylation | en |
| dc.subject | Friedel-Crafts reaction | en |
| dc.subject | deoxygenation reaction | en |
| dc.subject | Grignard reaction | en |
| dc.subject | silanation reaction | en |
| dc.subject | HTPB | en |
| dc.subject | Butacene | en |
| dc.title | 二茂鐵衍生物接枝於尾端具有羥基之聚丁二烯之合成與性質探討 | zh_TW |
| dc.title | Synthesis and Characterization of Hydroxyl Terminated Polybutadiene Grafted with Ferrocene Derivative | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 100-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 邱文英,梁文傑,芮祥鵬,程耀毅 | |
| dc.subject.keyword | 膠合劑,佛瑞德－克來福特醯化反應,還原反應,格林鈉反應,矽烷化,端羥基聚丁二烯,矽氫加成反應, | zh_TW |
| dc.subject.keyword | Butacene,Friedel-Crafts reaction,deoxygenation reaction,Grignard reaction,silanation reaction,HTPB,hydrosilylation, | en |
| dc.relation.page | 105 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2012-08-13 | |
| dc.contributor.author-college | 工學院 | zh_TW |
| dc.contributor.author-dept | 化學工程學研究所 | zh_TW |
| 顯示於系所單位： | 化學工程學系 | |
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