Synthesis of 2,2-Diferrocenylpropane-based Tetrazole and Its Catalysis Performance for Thermal Decomposition of Ammonium Perchlorate

doi:10.7503/cjcu20120097

Abstract

Abstract:

Ferrocenyl derivatives as burning rate catalysts for hydroxyl-terminated polybutadiene(HTPB) have been used widely. Among them, binuclear ferrocenyl compounds perform much better due to good thermal stability, low volatility and migration so as to gradually be an important kind of burning rate catalyst. Research showed that N-heterocyclic energetic material compared to traditional ones had excellent catalytic effect and can be easily controlled through changing anion or cation. Considering performance superposition principle, a tetrazole and binuclear ferrocenyl should be combined into a molecule for mixing both excellences. In order to reduce volatility, migration and energy losses of such catalysts, groups containg-N can be introduced to enhance molecule polarity and strengthen van der Waals force between them and propellant, which are in favor of formation of hydrogen bond and increase of viscoplastic of HTPB within kept of high iron content of catalyst as a result of high combustion catalytic performance. This paper provides a multistep procedure for the preparation of 5-(2,2-diferrocenylpropane)-1H-tetrazole(4). After stepwise biopolymer and Vilsmeier formylation, 2,2-diferrocenylpropane carbaldehyde(1) was synthesized from ferrocene with moderate yield, and then compound 1 was transformed into 2,2-diferrocenylpropane carbaldehyde oxime(2). Dehydration of the oxime gave 2,2-diferrocenylpropane nitrile(3). Finally, compound 4 was obtained via click reaction([2+3] cycloaddi-tion) between compound 3 and sodium azide. Structures of the target compounds were characterized by ¹H NMR, FTIR and mass spectrum. Electrochemical properties of the target compounds were investigated by cyclic voltammetry and differential pulse voltammetry. Relationship between electrochemical behavior of multi-component redox and structure was discussed. Thermal decomposition characteristics of ammonium perchlorate (AP) with 5%(mass fraction) of compound 3 or 4 were investigated by differential scanning calorimetry (DSC) and thermogravimetry (TG) analysis. The results showed that the final exothermic peak temperature of AP was reduced by about 100℃ and compounds 3 and 4 had good combustion catalytic characteristics on AP.

Key words: Ferrocenyl derivatives, Tetrazole, Ammonium perchlorate, Thermal decomposition

CLC Number:

O626.2

TrendMD:

LIAO Wen-Xiang, DOU Ya-Jie, WANG Jing, XIE Li-Li, LIN Fen, YUAN Yao-Feng. Synthesis of 2,2-Diferrocenylpropane-based Tetrazole and Its Catalysis Performance for Thermal Decomposition of Ammonium Perchlorate[J]. Chem. J. Chinese Universities, 2012, 33(10): 2244.

[1]	TANG Gang, SUN Junjie, ZHANG Dongxin, WU Qiang, ZHANG Hexin, SHEN Haifeng, TAO Yi, LIU Xiuyu. Synthesis of Phosphaphenanthrene-modified Cardanol-based Polyol and Its Performance as Flame Retardant in Rigid Polyurethane Foams [J]. Chem. J. Chinese Universities, 2022, 43(4): 20210847.
[2]	WANG Jicheng,YUAN Yaofeng,ZHUO Jibin,YANG Sihan,LIN Fen. Synthesis of 2-Ferrocenyl-4,5-diphenylimidazolium Ionic Liquids and Their Catalysis Performance for Thermal Decomposition of Ammonium Perchlorate^† [J]. Chem. J. Chinese Universities, 2018, 39(5): 889.
[3]	WANG Cheng, GUO Lihong, LI Xingang, MA Kui, DING Tong, WANG Xinlei, CHENG Qingpeng, TIAN Ye. CuO Catalyst Supported on CeO₂ Prepared by Oxalate Thermal Decomposition Method for Preferential Oxidation of CO^† [J]. Chem. J. Chinese Universities, 2017, 38(12): 2296.
[4]	WANG Huichun, WANG Fachun, LI Baolin. Preparation of Cyclodextrin-based Mesoporous Carbon and Its Catalytic Performance^† [J]. Chem. J. Chinese Universities, 2016, 37(11): 2076.
[5]	XUE Yunna, LI Jiaoyi, HAO Zhijun, WAN Hong, ZHAO Haixia, Li Chunying, DU Yongmei, Lu Juyou, Yu Qinwei, Lü Jian. Synthesis, Thermal Decomposition Mechanism and Kinetic Equation of Polyhedral Boron Hydride Compound [(C₂H₅)₄N]₂B₁₀H₁₀ with High Enthalpy of Combustion^† [J]. Chem. J. Chinese Universities, 2015, 36(2): 375.
[6]	CHEN Youning, GAO Li, HE Maofang, WEI Yinmao. High-capacity Polyvinyltetrazole-grafted Chelating Resin for Adsorption of Heavy Metal Ions^† [J]. Chem. J. Chinese Universities, 2014, 35(7): 1596.
[7]	DU Yongmei, LI Chunying, ZHANG Jianwei, WANG Wei, KANG Jianping, LÜ Jian. Synthesis and Thermal Decomposition of Tetrahydrotricyclopentadiene as a High Density Hydrocarbon Fuel^† [J]. Chem. J. Chinese Universities, 2014, 35(4): 755.
[8]	ZHANG Yi, YANG Xiangui, WANG Qingyin, YAO Jie, HU Jing, WANG Gongying. Synthesis of Nitro-modified MOF-5 and Its Application on Catalyzing the Thermal Decomposition of Carbamates^† [J]. Chem. J. Chinese Universities, 2014, 35(3): 613.
[9]	ZHU Yan-Li, JIAO Qing-Jie, HUANG Hao, REN Hui. Effect of Aluminum Particle Size on Thermal Decomposition of AP [J]. Chem. J. Chinese Universities, 2013, 34(3): 662.
[10]	LU Wen-Guan, LIU Hong-Wen, YIN Xu-Guang, LAN Lu-Mei, LIU Hai-Yao. Diverse Structures of Two Zn(Ⅱ) Coordination Polymers with 5-Amino-tetrazolate and 1,4-Benzenedicarboxylate Tuned by Solvent System [J]. Chem. J. Chinese Universities, 2013, 34(12): 2691.
[11]	JIANG Ze-Quan, SONG Sheng, DOU Hong-Jing, SUN Kang, WANG Yi-Ming, HUANG Chao-Fan, WEI Zhen-Hua, QU Guan-Xiong. Synthesis of Polycarboxylic Ligand Capped Fe₃O₄ Nanoparticles with Excellent Water-dispersibility via a Ligand-exchange Approach [J]. Chem. J. Chinese Universities, 2012, 33(12): 2609.
[12]	DING Xiao-Qin, DING Jun-Jie, LI Da-Yu, SUN Yang, CHEN Ji-Sheng. Theoretic Prediction of Heat Decomposition Stability for General Organic Molecular or Drug [J]. Chem. J. Chinese Universities, 2012, 33(05): 1063.
[13]	SHEN Wen-Ning, FENG La-Jun, FENG Hui. Preparation and Non-isothermal Kinetics of Thermal Decomposition of AgO-loaded Diatomite Composite [J]. Chem. J. Chinese Universities, 2012, 33(02): 353.
[14]	DU Yong-Mei*, WANG Wei, KANG Jian-Ping, LI Chun-Ying, YANG Jian-Ming, ZHANG Wei, Lü Jian. Synthesis and Thermal Decomposition of Tetracyclo[9.2.1.0^2,10.1^3,8]Tetradecane as a High Density Hydrocarbon Fuel [J]. Chem. J. Chinese Universities, 2011, 32(8): 1849.
[15]	TANG Zhan, ZHANG Guo-Tao, ZHANG Tong-Lai*, LI Zhi-Min, YANG Li, ZHANG Jian-Guo, QIAO Xiao-Jing. Crystal Structure, Thermal Properties, Sensitivity Test and Catalytic Activity of Energetic Compound[Cu(tza)₂]_n [J]. Chem. J. Chinese Universities, 2011, 32(8): 1870.

Synthesis of 2,2-Diferrocenylpropane-based Tetrazole and Its Catalysis Performance for Thermal Decomposition of Ammonium Perchlorate

PDF (PC)

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments