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FOX-7

FOX-7 or 1,1-diamino-2,2-dinitroethylene (DADNE)[3] is an insensitive high explosive compound. It was first synthesized in 1998 by the Swedish National Defence Research Institute (FOS).[4] 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.[5]

FOX-7
Names
Preferred IUPAC name
2,2-Dinitroethene-1,1-diamine
Other names
FOX-7
FOX7
Identifiers
  • 145250-81-3 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 467536
ECHA InfoCard 100.130.630
EC Number
  • 604-466-1
  • 536770
UNII
  • 3B2KYV7C3F
  • DTXSID70894014
  • InChI=1S/C2H4N4O4/c3-1(4)2(5(7)8)6(9)10/h3-4H2
    Key: FUHQFAMVYDIUKL-UHFFFAOYSA-N
  • N/C(N)=C([N+]([O-])=O)\[N+]([O-])=O
Properties
C2H4N4O4
Molar mass 148.08
Appearance Bright yellow crystalline powder[1]
Density 1.885 g cm−3
Melting point 238 °C (460 °F; 511 K) (decomposes)
Soluble in polar aprotic solvents such as dimethyl sulfoxide (DMSO), N,N-Dimethylformamide (DMF), and N-Methyl-2-pyrrolidone (NMP)[1]
Hazards
GHS labelling:
Danger
H201, H228, H302
P210, P230, P240, P241, P250, P264, P270, P280, P301+P312, P330, P370+P378, P370+P380, P372, P373, P401, P501
Explosive data
Friction sensitivity >350N[2]
Detonation velocity 8870 m/s at density 1.885 g cm−3 (estimated)
8335 m/s at density 1.756 g cm−3 (measured, small-scale testing)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

FOX-7 is similar to the insensitive chemical compound TATB, which is a benzene ring compound with three amino and three nitro groups.[6] 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.[1] FOX-7 is stoichiometrically identical (but structurally unrelated)[2] to the explosives and propellants RDX and HMX, and therefore produces the same quantity of gas per gram, a key determinant of performance.[1]

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.[2] 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.[7] FOX-7 has been calculated to have a detonation velocity of 8,870 m/s.[8] 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.[2]

FOX-7 is produced as of 2018 by EURENCO Bofors AB of Sweden,[9] having been made in batches up to 7kg in 2001.[10] 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.[2] 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.[11]

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,[1] including in Australia, India, the USA, and Sweden.[5][2][9][10]

References edit

  1. ^ a b c d e 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. ^ a b c d e f 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. (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. ^ a b 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 2005-05-22 at the Wayback Machine, Karlsson et al., 2002, accessed Aug 25, 2005
  9. ^ a b 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. (PDF) from the original on 25 January 2021. Retrieved 25 January 2021.
  10. ^ a b 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. 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 edit

  • 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.

diamino, dinitroethylene, dadne, insensitive, high, explosive, compound, first, synthesized, 1998, swedish, national, defence, research, institute, name, derived, from, acronym, swedish, defence, research, agency, with, replaced, indicate, explosive, names, pr. FOX 7 or 1 1 diamino 2 2 dinitroethylene DADNE 3 is an insensitive high explosive compound It was first synthesized in 1998 by the Swedish National Defence Research Institute FOS 4 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 5 FOX 7 Names Preferred IUPAC name 2 2 Dinitroethene 1 1 diamine Other names FOX 7FOX7 Identifiers CAS Number 145250 81 3 Y 3D model JSmol Interactive image ChemSpider 467536 ECHA InfoCard 100 130 630 EC Number 604 466 1 PubChem CID 536770 UNII 3B2KYV7C3F CompTox Dashboard EPA DTXSID70894014 InChI InChI 1S C2H4N4O4 c3 1 4 2 5 7 8 6 9 10 h3 4H2Key FUHQFAMVYDIUKL UHFFFAOYSA N SMILES N C N C N O O N O O Properties Chemical formula C2H4N4O4 Molar mass 148 08 Appearance Bright yellow crystalline powder 1 Density 1 885 g cm 3 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 1 Hazards GHS labelling Pictograms 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 gt 350N 2 Detonation velocity 8870 m s at density 1 885 g cm 3 estimated 8335 m s at density 1 756 g cm 3 measured small scale testing Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references FOX 7 is similar to the insensitive chemical compound TATB which is a benzene ring compound with three amino and three nitro groups 6 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 1 FOX 7 is stoichiometrically identical but structurally unrelated 2 to the explosives and propellants RDX and HMX and therefore produces the same quantity of gas per gram a key determinant of performance 1 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 2 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 7 FOX 7 has been calculated to have a detonation velocity of 8 870 m s 8 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 2 FOX 7 is produced as of 2018 by EURENCO Bofors AB of Sweden 9 having been made in batches up to 7kg in 2001 10 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 2 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 11 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 1 including in Australia India the USA and Sweden 5 2 9 10 References edit a b c d e 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 a b c d e f Ian J Lochert November 2001 FOX 7 A New Insensitive Explosive PDF Technical report Fisherman s Bend Victoria Australia Defense Science amp Technology Organization DSTO TR 1238 Archived PDF from the original on 2021 01 25 Retrieved 2021 01 25 US patent 6340780 Nikolai Latypov Ulf Wellmar amp Abraham Langlet Method of preparing salts of dinitromethane issued 2002 01 22 assigned to Swedish Defence Research Agency Bemm U Ostmark 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 a b 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 Herve Gregoire 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 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 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 a b 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 a b 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 fur Chemische Technologie pp 26 1 26 21 Archived from the original on 2021 01 25 Retrieved 2021 01 25 US patent 6312538 Nikolai Latypov Ulf Wellmar amp 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 editSorescu 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 Jurgen Klapotke Thomas M Mayer Peter Oehlinger Gilbert Welch Jan 2006 A and b 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 Retrieved from https en wikipedia org w index php title FOX 7 amp oldid 1166991518, wikipedia, wiki, book, books, library,

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