Bis-oxadiazole

Bis-oxadiazole, or more formally known as bis(1,2,4-oxadiazole)bis(methylene) dinitrate, is a nitrated heterocyclic compound of the oxadiazole family.[1]

Bis-oxadiazole
Names
Preferred IUPAC name
[3,3′-Bi-1,2,4-oxadiazole]-5,5′-diylbis(methylene) dinitrate
Other names
  • Bis(1,2,4-oxadiazole)bis(methylene) dinitrate
  • Bis-isoxazole-bis-methylene dinitrate
  • BIDN
Identifiers
3D model (JSmol)
  • InChI=1S/C6H4N6O8/c13-11(14)17-1-3-7-5(9-19-3)6-8-4(20-10-6)2-18-12(15)16/h1-2H2
    Key: AVTVAJHPJUFZPZ-UHFFFAOYSA-N
  • [O-][N+](=O)OCC1=NC(=NO1)C1=NOC(CO[N+]([O-])=O)=N1
Properties
C6H4N6O8
Molar mass 288.132 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bis-oxadiazole is related to bis-isoxazole tetranitrate (BITN), which was developed at the United States Army Research Laboratory (ARL). With a high nitrogen content, these compounds are poised to release a large volume of very stable N2.[2] It is a “melt-cast” explosive material that is potentially both more powerful and environmentally friendly alternative to TNT.[3]

Synthesis

Glyoxal condenses with hydroxylamine to yield diaminoglyoxime (DAG). Treating DAG with methyl glycolate in the presence of base at high temperature yields bis(1,2,4-oxadiazole).[4]

Replacement for TNT

TNT is attractive explosive because it is a melt-castable. A low melting point of about 80 °C and high decomposition temperature of 295 °C allows manufacturers to safely pour TNT into molds. The production of TNT generates hazardous waste, e.g. red water and pink water.[1]

Bis-oxadiazole, which is also melt-castable, is about 1.5 times more powerful than TNT and yet produces less hazardous wastes.[1]

Physical Properties of Bis-oxadiazole Compared to TNT[4]
Physical Property bis-oxadiazole TNT
Onset temperature of melting 84.5 °C 80.4 °C
Onset temperature of decomposition 183.4 °C 295.0 °C
Derived density from X-ray data 1.832 g cm−3 1.65 g cm−3
Detonation pressure 29.4 GPa 20.5 GPa
Detonation velocity 8180 m s−1 6950 m s−1
Molar enthalpy of formation -79.4 kJ mol−1 -59.3 kJ mol−1

A major challenge in the production of bis-oxadiazole is its low yield.[5]

References
  1. Bennett, Jay (July 2, 2018). "So Long TNT, There's a New Explosive in Town". Popular Mechanics. Retrieved August 2, 2018.
  2. McNally, David (May 3, 2016). "Army scientists synthesize high-performing energetic material". Medium. Archived from the original on August 2, 2018. Retrieved August 2, 2018.
  3. "TNT could be headed for retirement after 116 years on the job". Phys.org. June 14, 2018. Retrieved August 2, 2018.
  4. Johnson, Eric; Sabatini, Jesse; Chavez, David; Sausa, Rosario; Byrd, Edward; Wingard, Leah; Guzmàn, Pablo (2018). "Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient". Organic Process Research & Development. 22 (6): 736–740. doi:10.1021/acs.oprd.8b00076. OSTI 1484644.
  5. Halford, Bethany (June 5, 2018). "Double oxadiazole could replace TNT". c&en. Retrieved August 2, 2018.
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