Citation: Zhang Jiarong, Bi Fuqiang, Lian Peng, Zhang Junlin, Wang Bozhou. Synthesis and Characterization of an Energetic Compound 3, 3'-Bis(fluoronitromethyl-ONN-azoxy) azoxyfurazan[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2736-2744. doi: 10.6023/cjoc201701014 shu

Synthesis and Characterization of an Energetic Compound 3, 3'-Bis(fluoronitromethyl-ONN-azoxy) azoxyfurazan

Zhang Jiarong ^a,b ,
Bi Fuqiang ^a,b,, ,
Lian Peng ^a,b ,
Zhang Junlin ^a,b ,
Wang Bozhou ^a,b,,

a.
Xi'an Mordern Chemistry Research Institute, Xi'an 710065
b.
State Key Laboratory of Fluorine & Nitrogen Chemicals, Xi'an 710065

Corresponding author: Bi Fuqiang, bifuqiang@gmail.com Wang Bozhou, wbz600@163.com
Received Date: 5 January 2017
Revised Date: 14 March 2017
Available Online: 2 October 2017
Fund Project: the National Natural Science Foundation of China 21243007Project supported by the National Natural Science Foundation of China (No. 21243007)

Figures(6)

Using 3, 3'-diamino-4, 4'-azoxyfurazan (DAOAF) and 2, 2-dimethyl-5-nitro-5-nitroso-1, 3-dioxane (DMNNDO) as starting materials, energetic compound 3, 3'-bis(fluoronitromethyl-ONN-azoxy)azoxyfurazan (FDNAF) was designed and synthesized via oxidation coupling, hydrolysis, bromization, reduction, nitration, salification and fluorination etc., and the structures of all the intermediates and the title compound were characterized by IR, ¹H NMR, ¹³C NMR, ¹⁵N NMR、¹⁹F NMR and elemental analysis. Using HCl/CH₃CH₂OH as the hydrolysis system instead of AcCl/CH₃OH, the condition of hydrolysis reaction was optimized, the reaction time was shortened from 18 h to 2 h and the purity of raw product was improved to 93%. The bromination reaction conditions were also studied. Under the optimum conditions with the temperature of 20℃ and the reaction time of 30 min, the brominated product was obtained with a yield of 51.5%. Based on B3LYP method of density function theory, ¹³C NMR, ¹⁵N NMR and IR chemical shifts were studied theoretically, which agreed with experimental data. The physicochemical properties, detonation performances and thermal behaviors of 3, 3'-bis(nitromethyl-ONN-azoxy)azoxyfurazan (BNMAF), 3, 3'-bis(dinitromethyl-ONN-azoxy)azoxyfurazan (BDNAF) and FDNAF were studied and analyzed. The results proved that FDNAF is a potential energetic compound with the theoretical density of 2.02 g·cm^-3, the decomposition point of 233.4℃, the oxygen balance of 6.72%, the explosion velocity of 9735 m·s^-1, the detonation pressure of 44.9 GPa, and the characteristic drop height of impact sensitivity of 36 cm.
- organic chemistry,
- fluoronitromethyl-ONN-azoxy group,
- energetic compound,
- synthesis
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