Synthesis and Characterization of Fluorodinitrobenzenes with Tunable Melting Point: Potential Low Sensitive Energetic Plasticizer and Melt‐Cast Carrier^†

Abstract

of main observation and conclusion In order to explore the effects of fluoro substituents on the energy and safety of energetic compounds, a series of fluorodinitrobenzenes including 1,3-difluoro-2,4-dinitrobenzene (1), 1,5-difluoro-2,4-dinitrobenzene (2), 1,2,3-trifluoro-4,6-dinitrobenzne (3) and 1,3,5-trifluoro-2,4-dinitrobenzene (4) were prepared. All the compounds were fully characterized. The structures of 2 and 3 were further confirmed by single crystal X-ray diffraction analysis. The results show that these compounds exhibit comparable detonation properties (D = 6703-6978 m•s-1 , and p = 21.3-23.7 GPa) to those of 2,4,6-trinitrotoluene (TNT) due to the significantly increased density of fluorine introduced. Low sensitivity (IS > 40 J, and FS > 360 N) of these compounds along with different melting points make them potential candidates for different allocation. Among them, 1 and 4 with the melting point of 42.5 ℃ and 55.2 ℃, respectively, show promise for application in the field of energetic plasticizer. Compounds 2 and 3 are potential low sensitive melt-cast carrier due to their similar melting point and superior detonation performance to that of TNT.

Synthesis and characterization of potential polycyclic energetic materials using bicyclic triazole and azetidine structures as building blocks

“…18,29 Furthermore, it is generally believed that nitro can improve the molecular density, enthalpy of formation, oxygen balance and nitrogen content, which promotes the application of DNAZ in energetic materials; fluorine atoms can increase density and release a large amount of heat by reacting with metal aluminum or aluminum oxide, which suggests that DFAZ derivatives may be used as fluorine-containing oxidants in propellants 28 and melt cast explosives. 30…”

“…18,29 Furthermore, it is generally believed that nitro can improve the molecular density, enthalpy of formation, oxygen balance and nitrogen content, which promotes the application of DNAZ in energetic materials; uorine atoms can increase density and release a large amount of heat by reacting with metal aluminum or aluminum oxide, which suggests that DFAZ derivatives may be used as uorinecontaining oxidants in propellants 28 and melt cast explosives. 30 The purpose of this work was to explore and verify a design method for developing new polycyclic energetic compounds. Some new triazolyl polycyclic intermediates were prepared successfully by nucleophilic substitution reactions between chlorinated azobis-1,2,4-triazole/chlorinated bi-1,2,4-triazole with DNAZ or DFAZ under alkaline conditions.…”

Towards Investigating the Effect of Ammonium Nitrate on the Characteristics and Thermal Decomposition Behavior of Energetic Double Base NC/DEGDN Composite

“…Such energetic formulations are known for their excellent energetic performance, interesting mechanical characteristics, attractive operational features, and mature processing technology, increasing their demand for several military uses in missiles, rocket motors, and boosters [4]. As an important ingredient in MDBs, energetic plasticizers such as nitroglycerine (NG), diethylene glycol dinitrate (DEGDN) and ethylene glycol dinitrate (EGDN) act as a fuel and improve the overall energy level, plasticity, and physical characteristics of the propellant [5,6]. Broadly, an appropriate plasticizer should display acceptable sensitivity, compatibility with other components, suitable melting point, and good density [6].…”

“…As an important ingredient in MDBs, energetic plasticizers such as nitroglycerine (NG), diethylene glycol dinitrate (DEGDN) and ethylene glycol dinitrate (EGDN) act as a fuel and improve the overall energy level, plasticity, and physical characteristics of the propellant [5,6]. Broadly, an appropriate plasticizer should display acceptable sensitivity, compatibility with other components, suitable melting point, and good density [6]. Nonetheless, nitroglycerine, the most largely employed energetic plasticizer, suffers from various problems, including sensitivity to friction and impact, low oxygen balance (3.5%), reduced thermal stability, and migratory issues [7][8][9].…”

“…As an energetic plasticizer, EGDN was found to be more effective than NG and present high energy, while being less sensitive to impact [11]. In one research paper, Yunlu Li et al [6] mentioned that the introduction of hydrogen bond functional groups such as -NH 2 , -CH 3, or other functions into energetic compounds would enhance their safety. Therefore, the use of DEGDN, which forms homogenous matrices with NC promoted by the electrostatic N-O interactions and the hydrogen bond network, has actually attracted much attention as a prominent alternative plasticizer in energetic formulations [8,9].…”