A New Synthetic Route for 3,3′-Bis(fluorodinitromethyl)difurazanyl Ether (FOF-13) and Its Energetic Properties

Abstract

A new protocol for preparation of 3,3-bis(fluorodinitromethyl)difurazanyl ether (FOF-13) was developed. It involves (i) nitration of 3,3’-bis(chlorohydroxyminomethyl)difurazanyl ether with N2O5/MeCN to give 3,3-bis(chlorodinitromethyl)difurazanyl ether (4), (ii) reduction of 4 with KI/MeOH to obtain potassium salt of 3,3’-bis(dinitromethyl)difurazanyl ether (6) and (iii) fluorination of 6 with XeF2 in anhydrous acetonitrile to form the desired FOF-13. FOF-13 was fully characterized by IR, 13C NMR, 19F NMR, and elemental analysis. FOF-13 exhibits excellent physicochemical and detonation properties, such as high density (1.91 g cm‒3), good thermal stability, reasonable impact sensitivity (14 J) and friction sensitivity (64%), high measured detonation velocity (8497 m s‒1 at 1.69 g cm‒3). Furthermore, the precursors 4 and 6 were developed for the first time.