Chinese Journal of Organic Chemistry >
Synthesis and Characterization of an Energetic Compound 3,3'-Bis(fluoronitromethyl-ONN-azoxy) azoxyfurazan
Received date: 2017-01-05
Revised date: 2017-03-14
Online published: 2017-06-02
Supported by
Project supported by the National Natural Science Foundation of China (No.21243007).
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.
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
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