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

doi:10.6023/cjoc201701014

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (10): 2736-2744.DOI: 10.6023/cjoc201701014 Previous Articles Next Articles

ARTICLE

含能化合物3,3'-双(氟二硝甲基-ONN-氧化偶氮基)氧化偶氮呋咱合成与表征

张家荣^a,b, 毕福强^a,b, 廉鹏^a,b, 张俊林^a,b, 王伯周^a,b

a 西安近代化学研究所西安 710065;
b 氟氮化工资源高效开发与利用国家重点实验室西安 710065

收稿日期:2017-01-05 修回日期:2017-03-14 发布日期:2017-06-02
通讯作者: 毕福强, 王伯周 E-mail:bifuqiang@gmail.com;wbz600@163.com
基金资助:
国家自然科学基金（No.21243007）资助项目.

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

Received:2017-01-05 Revised:2017-03-14 Published:2017-06-02
Contact: 10.6023/cjoc201701014 E-mail:bifuqiang@gmail.com;wbz600@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (No.21243007).

1. Synthesis and Characterization of an Energetic Compound 3,3'-Bis(fluoronitromethyl-ONN-azoxy) azoxyfurazan.PDF(1697KB)

Abstract

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.

Key words: organic chemistry, fluoronitromethyl-ONN-azoxy group, energetic compound, synthesis

Cite this article

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]. Chin. J. Org. Chem., 2017, 37(10): 2736-2744.

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含能化合物3,3'-双(氟二硝甲基-ONN-氧化偶氮基)氧化偶氮呋咱合成与表征

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

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