New plasticizers for energetic materials

Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient

“…Diaminoglyoxime (3) was synthesized according to the literature. 21 1 H and 13 C NMR spectra were recorded using an Anasazi 90 MHz instrument. The chemical shifts quoted in parts per million in the text refer to typical standard tetramethylsilane in CDCl 3 as the solvent.…”

“…The solid was collected by Buchner filtration and oven-dried at 60 °C overnight to afford 24.4 g of bis(1,2,4-oxadiazole) 5 (68% yield) as a white powder. T melt = 107.5 °C; 1 H NMR (90 MHz, DMSO-d 6 ) δ 5.53 (s, 4H), 2.18 (s, 6H); 13 [3,3′-Bis(1,2,4-oxadiazole)]-5,5′-diyldimethanol (4). To a 250 mL round-bottom flask equipped with a stir bar were sequentially added 50 mL of MeOH, 5 (24.0 g, 85.1 mmol, 1.00 equiv), and K 2 CO 3 (1.18 g, 8.51 mmol, 0.100 equiv).…”

Structures and Binding Energies of Nitrate Plasticizers DEGDN, TEGDN, and Nitroglycerine

“…Likewise, all computed angles compare favorably with previously reported data [20,23,32,33], with average deviations of less than 1 degree. NG and other similar molecules have been previously studied utilizing DFT methods, primarily with the B3LYP functional [13,20,22,23,[34][35][36][37][38][39]. However, the M06 family of functionals used in the present study have been shown to outperform B3LYP in predictions of both structures and energetics of small organics [40] as well as systems with significant dispersion interactions and hydrogen bonding [41].…”

Synthesis of Biisoxazoletetrakis(methyl nitrate): A Potential Nitrate Plasticizer and Highly Explosive Material

“…[5][6][7][8][9] One of the biggest challenges in creating energetic plasticizers is retaining reasonable sensitivity, suppressing chemical reactivity, and ensuring a high thermal stability as one approaches oxygenbalanced materials, while creating the densest material possible. In designing an optimal plasticizer material, it is important to gain an understanding of how chemical structures (alkyl substituents) affect physical properties (melting, onset of decomposition, and safety) of candidate materials.…”

“…While recent efforts by a variety of authors have created some potentially useful plasticizer molecules, most of these molecules have been analogues of well-known materials such as nitroxyethyl nitramines (NENAs), azides, or alkyl nitrates. [5][6][7][8][9] One of the biggest challenges in creating energetic plasticizers is retaining reasonable sensitivity, suppressing chemical reactivity, and ensuring a high thermal stability as one approaches oxygenbalanced materials, while creating the densest material possible. If nitroglycerine (NG) were discovered by scientists today, [10][11][12] its very low thermal stability and high reactivity would leave it as a laboratory curiosity.…”