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FOX-7

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FOX-7
Names
Preferred IUPAC name 2,2-Dinitroethene-1,1-diamine
Other names FOX-7
FOX7
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.130.630 Edit this at Wikidata
EC Number
  • 604-466-1
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H4N4O4/c3-1(4)2(5(7)8)6(9)10/h3-4H2Key: FUHQFAMVYDIUKL-UHFFFAOYSA-N
SMILES
  • N/C(N)=C(()=O)\()=O
Properties
Chemical formula C2H4N4O4
Molar mass 148.08
Appearance Bright yellow crystalline powder
Density 1.885 g cm
Melting point 238 °C (460 °F; 511 K) (decomposes)
Solubility in water Soluble in polar aprotic solvents such as dimethyl sulfoxide (DMSO), N,N-Dimethylformamide (DMF), and N-Methyl-2-pyrrolidone (NMP)
Hazards
GHS labelling:
Pictograms GHS01: ExplosiveGHS02: FlammableGHS07: Exclamation mark
Signal word Danger
Hazard statements H201, H228, H302
Precautionary statements P210, P230, P240, P241, P250, P264, P270, P280, P301+P312, P330, P370+P378, P370+P380, P372, P373, P401, P501
Explosive data
Friction sensitivity >350N
Detonation velocity 8870 m/s at density 1.885 g cm (estimated)
8335 m/s at density 1.756 g cm (measured, small-scale testing)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

FOX-7 or 1,1-diamino-2,2-dinitroethylene (DADNE) is an insensitive high explosive compound. It was first synthesized in 1998 by the Swedish National Defence Research Institute (FOA). According to other information it was synthesized in the USSR in 1990. The name FOX-7 is derived from the acronym of the Swedish Defence Research Agency (FOI), with the I replaced by an X to indicate an explosive, as in RDX and HMX.

FOX-7 is similar to the insensitive chemical compound TATB, which is a benzene ring compound with three amino and three nitro groups. FOX-7 has a two-carbon backbone rather than a benzene ring, but the amino and nitro groups have similar effects in both cases according to published reports on the sensitivity and chemical decay processes of FOX-7. FOX-7 is stoichiometrically identical (but structurally unrelated) to the explosives and propellants RDX and HMX, and therefore produces the same quantity of gas per gram, a key determinant of performance.

By various measures, such as dropped-weight impact, friction force, temperature of ignition, and response to heating under confinement, it is less sensitive than the benchmark explosive RDX, while having performance slightly greater than the same. Its explosive properties appear extremely favorable; in addition to its insensitive properties, the detonation velocity of mixtures of 80% FOX-7 plus binders is as high as Composition B, and nearly pure FOX-7 based plastic bonded explosives are slightly superior to RDX. FOX-7 has been calculated to have a detonation velocity of 8,870 m/s. Charges composed of EVA-coated FOX-7 granules pressed into pellets of 92% theoretical maximum density were found to have a detonation velocity of 7730 m/s, compared to 7630 m/s for a similar RDX/EVA composition, and 5% greater detonation pressure.

FOX-7 is produced as of 2018 by EURENCO Bofors AB of Sweden, having been made in batches up to 7kg in 2001. In laboratory-scale synthesis, material costs were calculated at ~AU$3000/kg (prices in 2002 AUD) using prices from research chemical suppliers. At that time, FOX-7 could be purchased from NEXPLO Bofors AB at SEK3200/kg. Due to its small-scale production, the cost of FOX-7 is relatively high. However, the production is based on commercial starting material and the synthesis is uncomplicated.

FOX-7 is an attractive subject for research and development due to its combination of insensitivity and power. FOX-7 performs similarly to RDX, one of the most powerful explosives and propellants in use, unlike other insensitive high explosives under investigation, such as TATB, nitrotriazolone, TEX, and 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105). Due to the need for less sensitive munitions, FOX-7 is being investigated at many military research centers, including in Australia, India, the USA, and Sweden.

References

  1. ^ Anniyappan, M.; Talawar, M.B.; Gore, G.M.; Venugopalan, S.; Gandhe, B.R. (2006). "Synthesis, characterization and thermolysis of 1,1-diamino-2,2-dinitroethylene (FOX-7) and its salts". Journal of Hazardous Materials. 137 (2): 812–9. doi:10.1016/j.jhazmat.2006.03.034. PMID 16701943.
  2. ^ Ian J., Lochert (November 2001). FOX-7 - A New Insensitive Explosive (PDF) (Technical report). Fisherman's Bend, Victoria, Australia: Defense Science & Technology Organization. DSTO-TR-1238. Archived (PDF) from the original on 2021-01-25. Retrieved 2021-01-25.
  3. US patent 6340780, Nikolai Latypov; Ulf Wellmar & Abraham Langlet, "Method of preparing salts of dinitromethane", issued 2002-01-22, assigned to Swedish Defence Research Agency 
  4. Bemm, U.; Östmark, H. (1998) "1,1-Diamino-2,2-dinitroethylene: a Novel Energetic Material with Infinite Layers in Two Dimensions". Acta Cryst C54: 1997-1999. doi:10.1107/S0108270198007987.
  5. ^ Viswanath, Dabir S.; Ghosh, Tushar K.; Boddu, Veera M. (2018), "FOX-7 (1,1-Diamino-2,2-Dinitroethylene)", Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties, Dordrecht: Springer Netherlands, pp. 101–139, doi:10.1007/978-94-024-1201-7_3, ISBN 978-94-024-1199-7, retrieved 2021-01-25
  6. Hervé, Grégoire; Jacob, Guy; Latypov, Nikolaj (2005). "The reactivity of 1,1-diamino-2,2-dinitroethene (FOX-7)". Tetrahedron. 61 (28): 6743. doi:10.1016/j.tet.2005.05.010.
  7. Latypov, Nikolai V.; Bergman, Jan; Langlet, Abraham; Wellmar, Ulf; Bemm, Ulf (1998). "Synthesis and reactions of 1,1-diamino-2,2-dinitroethylene". Tetrahedron. 54 (38): 11525–11536. doi:10.1016/s0040-4020(98)00673-5.
  8. Detonation and Sensitivity Properties of FOX-7 and Formulations Containing FOX-7 Archived 2005-05-22 at the Wayback Machine, Karlsson et al., 2002, accessed Aug 25, 2005
  9. ^ Sleadd, Bradley A.; Boruta, David T.; Clubb, Joseph W. (24 April 2018). Development of a CONUS manufacturing capability for FOX-7 (PDF) (Technical report). National Defense Industrial Association. Archived (PDF) from the original on 25 January 2021. Retrieved 25 January 2021.
  10. ^ Ostmark, Henric; Bergman, Helena; Bemm, Ulf; Goede, Patrick (6 July 2001). "Energetic Materials: Ignition, Combustion and Detonation". 2, 2-dinitro-ethene-1, 1-diamine(FOX-7)- Properties, analysis and scale-up. 32nd International Conference of ICT. Karlsruhe, Germany: Fraunhofer-Institut für Chemische Technologie. pp. 26-1 – 26-21. Archived from the original on 2021-01-25. Retrieved 2021-01-25.
  11. US patent 6312538, Nikolai Latypov; Ulf Wellmar & Abraham Langlet, "Chemical compound suitable for use as an explosive, intermediate and method for preparing the compound", issued 2001-11-06, assigned to Swedish Defence Research Agency 

Further reading

  • Sorescu, Dan C.; Boatz, Jerry A.; Thompson, Donald L. (2001). "Classical and Quantum-Mechanical Studies of Crystalline FOX-7 (1,1-Diamino-2,2-dinitroethylene)". The Journal of Physical Chemistry A. 105 (20): 5010. Bibcode:2001JPCA..105.5010S. doi:10.1021/jp010289m.
  • Evers, Jürgen; Klapötke, Thomas M.; Mayer, Peter; Oehlinger, Gilbert; Welch, Jan (2006). "Α- and β-FOX-7, Polymorphs of a High Energy Density Material, Studied by X-ray Single Crystal and Powder Investigations in the Temperature Range from 200 to 423 K". Inorganic Chemistry. 45 (13): 4996–5007. doi:10.1021/ic052150m. PMID 16780321.
  • Schmidt, Eckart W. (2022). "1,1‑Diamino-2,2‑Dinitroethene". Nitroaliphatic Compounds. Encyclopedia of Oxidizers. De Gruyter. pp. 2304–2326. doi:10.1515/9783110750294-016. ISBN 978-3-11-075029-4.
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