Bis-oxadiazole

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Bis-oxadiazole
Bis(1,2,4-oxadiazole)bis(methylene) dinitrate.svg
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).

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 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[edit]

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[edit]

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[edit]

  1. ^ a b c 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. 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. ^ a b 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.