FOX-7: Difference between revisions
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'''FOX-7''' or '''1,1-diamino-2,2-dinitroethylene''' '''(DADNE)'''<ref>US Patent 6340780 - Method of preparing salts of dinitromethane</ref> is an [[Insensitive munition#Insensitive high explosives|insensitive high explosive]] compound. It was first synthesized in 1998 by the [[Swedish National Defence Research Institute]] (FOS).<ref name="dsto">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}}.</ref> The name FOX-7 is derived from the acronym of the [[Swedish Defence Research Agency|Swedish Defence Research Agency (FOI)]], with the ''I'' replaced by an ''X'' to indicate an explosive, as in [[RDX]] and [[HMX]].<ref>{{Citation|last1=Viswanath|first1=Dabir S.|title=FOX-7 (1,1-Diamino-2,2-Dinitroethylene)|date=2018|url=https://doi.org/10.1007/978-94-024-1201-7_3|work=Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties|pages=101–139|place=Dordrecht|publisher=Springer Netherlands|doi=10.1007/978-94-024-1201-7_3|isbn=978-94-024-1199-7|access-date=2021-01-25|last2=Ghosh|first2=Tushar K.|last3=Boddu|first3=Veera M.}}</ref> |
'''FOX-7''' or '''1,1-diamino-2,2-dinitroethylene''' '''(DADNE)'''<ref>US Patent 6340780 - Method of preparing salts of dinitromethane</ref> is an [[Insensitive munition#Insensitive high explosives|insensitive high explosive]] compound. It was first synthesized in 1998 by the [[Swedish National Defence Research Institute]] (FOS).<ref name="dsto">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}}.</ref> The name FOX-7 is derived from the acronym of the [[Swedish Defence Research Agency|Swedish Defence Research Agency (FOI)]], with the ''I'' replaced by an ''X'' to indicate an explosive, as in [[RDX]] and [[HMX]].<ref name=":0">{{Citation|last1=Viswanath|first1=Dabir S.|title=FOX-7 (1,1-Diamino-2,2-Dinitroethylene)|date=2018|url=https://doi.org/10.1007/978-94-024-1201-7_3|work=Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties|pages=101–139|place=Dordrecht|publisher=Springer Netherlands|doi=10.1007/978-94-024-1201-7_3|isbn=978-94-024-1199-7|access-date=2021-01-25|last2=Ghosh|first2=Tushar K.|last3=Boddu|first3=Veera M.}}</ref> |
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FOX-7 is similar to the insensitive chemical compound [[TATB]], which is a [[benzene]] ring compound with three [[amino]] and three [[nitro group]]s.<ref>{{cite journal|doi=10.1016/j.tet.2005.05.010|title=The reactivity of 1,1-diamino-2,2-dinitroethene (FOX-7)|year=2005|last1=Hervé|first1=Grégoire|last2=Jacob|first2=Guy|last3=Latypov|first3=Nikolaj|journal=Tetrahedron|volume=61|issue=28|pages=6743}}</ref> FOX-7 has a two-carbon backbone rather than a [[benzene]] ring, but the [[amino]] and [[nitro compound|nitro]] groups have similar effects in both cases according to published reports on the sensitivity and chemical decay processes of FOX-7.<ref name="Anniyappan" /> FOX-7 is stoichiometrically identical (but structurally unrelated)<ref name="Lochert" /> to the explosives and propellants [[RDX]] and [[HMX]], and therefore produces the same quantity of gas per gram, a key determinant of performance.<ref name="Anniyappan">{{cite journal|doi=10.1016/j.jhazmat.2006.03.034|title=Synthesis, characterization and thermolysis of 1,1-diamino-2,2-dinitroethylene (FOX-7) and its salts|year=2006|last1=Anniyappan|first1=M.|last2=Talawar|first2=M.B.|last3=Gore|first3=G.M.|last4=Venugopalan|first4=S.|last5=Gandhe|first5=B.R.|journal=Journal of Hazardous Materials|volume=137|issue=2|pages=812–9|pmid=16701943}}</ref> |
FOX-7 is similar to the insensitive chemical compound [[TATB]], which is a [[benzene]] ring compound with three [[amino]] and three [[nitro group]]s.<ref>{{cite journal|doi=10.1016/j.tet.2005.05.010|title=The reactivity of 1,1-diamino-2,2-dinitroethene (FOX-7)|year=2005|last1=Hervé|first1=Grégoire|last2=Jacob|first2=Guy|last3=Latypov|first3=Nikolaj|journal=Tetrahedron|volume=61|issue=28|pages=6743}}</ref> FOX-7 has a two-carbon backbone rather than a [[benzene]] ring, but the [[amino]] and [[nitro compound|nitro]] groups have similar effects in both cases according to published reports on the sensitivity and chemical decay processes of FOX-7.<ref name="Anniyappan" /> FOX-7 is stoichiometrically identical (but structurally unrelated)<ref name="Lochert" /> to the explosives and propellants [[RDX]] and [[HMX]], and therefore produces the same quantity of gas per gram, a key determinant of performance.<ref name="Anniyappan">{{cite journal|doi=10.1016/j.jhazmat.2006.03.034|title=Synthesis, characterization and thermolysis of 1,1-diamino-2,2-dinitroethylene (FOX-7) and its salts|year=2006|last1=Anniyappan|first1=M.|last2=Talawar|first2=M.B.|last3=Gore|first3=G.M.|last4=Venugopalan|first4=S.|last5=Gandhe|first5=B.R.|journal=Journal of Hazardous Materials|volume=137|issue=2|pages=812–9|pmid=16701943}}</ref> |
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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.<ref name="Lochert">{{cite techreport |first=Lochert |last=Ian J. |title=FOX-7 - A New Insensitive Explosive |number=DSTO-TR-1238 |publisher=Defense Science & Technology Organization |publication-place=Fisherman's Bend, Victoria, Australia |date=November 2001 |year=2001 |url=https://apps.dtic.mil/dtic/tr/fulltext/u2/a399359.pdf |access-date=2021-01-25 |archive-date=2021-01-25 |archive-url=https://web.archive.org/web/20210125141310/https://apps.dtic.mil/dtic/tr/fulltext/u2/a399359.pdf |url-status=live }}</ref> Its explosive properties appear extremely favorable; in addition to its insensitive properties, the detonation velocity of mixtures of 80% FOX-7 plus [[binder (material)|binders]] is as high as [[Composition B]], and nearly pure FOX-7 based [[plastic bonded explosive]]s are slightly superior to [[RDX]].<ref>{{Cite journal|last1=Latypov|first1=Nikolai V.|last2=Bergman|first2=Jan|last3=Langlet|first3=Abraham|last4=Wellmar|first4=Ulf|last5=Bemm|first5=Ulf|year=1998|title=Synthesis and reactions of 1,1-diamino-2,2-dinitroethylene|journal=Tetrahedron|volume=54|issue=38|pages=11525–11536|doi=10.1016/s0040-4020(98)00673-5}}</ref> FOX-7 has been calculated to have a [[detonation velocity]] of 8,870 m/s.<ref>[http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/Karlsson-165.pdf Detonation and Sensitivity Properties of FOX-7 and Formulations Containing FOX-7] {{Webarchive|url=https://web.archive.org/web/20050522150513/http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/Karlsson-165.pdf |date=2005-05-22 }}, Karlsson et al., 2002, accessed Aug 25, 2005</ref> Charges composed of [[Ethylene-vinyl acetate|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.<ref name="Lochert" /> |
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.<ref name="Lochert">{{cite techreport |first=Lochert |last=Ian J. |title=FOX-7 - A New Insensitive Explosive |number=DSTO-TR-1238 |publisher=Defense Science & Technology Organization |publication-place=Fisherman's Bend, Victoria, Australia |date=November 2001 |year=2001 |url=https://apps.dtic.mil/dtic/tr/fulltext/u2/a399359.pdf |access-date=2021-01-25 |archive-date=2021-01-25 |archive-url=https://web.archive.org/web/20210125141310/https://apps.dtic.mil/dtic/tr/fulltext/u2/a399359.pdf |url-status=live }}</ref> Its explosive properties appear extremely favorable; in addition to its insensitive properties, the detonation velocity of mixtures of 80% FOX-7 plus [[binder (material)|binders]] is as high as [[Composition B]], and nearly pure FOX-7 based [[plastic bonded explosive]]s are slightly superior to [[RDX]].<ref>{{Cite journal|last1=Latypov|first1=Nikolai V.|last2=Bergman|first2=Jan|last3=Langlet|first3=Abraham|last4=Wellmar|first4=Ulf|last5=Bemm|first5=Ulf|year=1998|title=Synthesis and reactions of 1,1-diamino-2,2-dinitroethylene|journal=Tetrahedron|volume=54|issue=38|pages=11525–11536|doi=10.1016/s0040-4020(98)00673-5}}</ref> FOX-7 has been calculated to have a [[detonation velocity]] of 8,870 m/s.<ref>[http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/Karlsson-165.pdf Detonation and Sensitivity Properties of FOX-7 and Formulations Containing FOX-7] {{Webarchive|url=https://web.archive.org/web/20050522150513/http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/Karlsson-165.pdf |date=2005-05-22 }}, Karlsson et al., 2002, accessed Aug 25, 2005</ref> Charges composed of [[Ethylene-vinyl acetate|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.<ref name="Lochert" /> |
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FOX-7 is produced as of 2018 by EURENCO [[Bofors]] AB of Sweden,<ref>{{cite techreport|last1=Sleadd|first1=Bradley A.|last2=Boruta|first2=David T.|last3=Clubb|first3=Joseph W.|title=Development of a CONUS manufacturing capability for FOX-7|institution=National Defense Industrial Association|date=24 April 2018|year=2018|url=https://ndiastorage.blob.core.usgovcloudapi.net/ndia/2018/imem/20157_Sleadd_Presentation.pdf|access-date=25 January 2021|archive-date=25 January 2021|archive-url=https://web.archive.org/web/20210125141312/https://ndiastorage.blob.core.usgovcloudapi.net/ndia/2018/imem/20157_Sleadd_Presentation.pdf|url-status=live}}</ref> having been made in batches up to 7kg in 2001.<ref>{{cite conference|last1=Ostmark|first1=Henric|last2=Bergman|first2=Helena|last3=Bemm|first3=Ulf|last4=Goede|first4=Patrick|date=6 July 2001|title=Energetic Materials: Ignition, Combustion and Detonation|url=https://apps.dtic.mil/sti/citations/ADA396885|conference=32nd International Conference of ICT|publisher=Fraunhofer-Institut für Chemische Technologie|pages=26-1 - 26-21|archive-url=https://web.archive.org/web/20210125141313/https://apps.dtic.mil/sti/citations/ADA396885|archive-date=2021-01-25|place=Karlsruhe, Germany|book-title=2, 2-dinitro-ethene-1, 1-diamine(FOX-7)- Properties, analysis and scale-up|access-date=2021-01-25|url-status=live}}</ref> 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.<ref name="Lochert" /> 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.<ref>US Patent 6312538 - Chemical compound suitable for use as an explosive, intermediate and method for preparing the compound</ref> |
FOX-7 is produced as of 2018 by EURENCO [[Bofors]] AB of Sweden,<ref name=":1">{{cite techreport|last1=Sleadd|first1=Bradley A.|last2=Boruta|first2=David T.|last3=Clubb|first3=Joseph W.|title=Development of a CONUS manufacturing capability for FOX-7|institution=National Defense Industrial Association|date=24 April 2018|year=2018|url=https://ndiastorage.blob.core.usgovcloudapi.net/ndia/2018/imem/20157_Sleadd_Presentation.pdf|access-date=25 January 2021|archive-date=25 January 2021|archive-url=https://web.archive.org/web/20210125141312/https://ndiastorage.blob.core.usgovcloudapi.net/ndia/2018/imem/20157_Sleadd_Presentation.pdf|url-status=live}}</ref> having been made in batches up to 7kg in 2001.<ref name=":2">{{cite conference|last1=Ostmark|first1=Henric|last2=Bergman|first2=Helena|last3=Bemm|first3=Ulf|last4=Goede|first4=Patrick|date=6 July 2001|title=Energetic Materials: Ignition, Combustion and Detonation|url=https://apps.dtic.mil/sti/citations/ADA396885|conference=32nd International Conference of ICT|publisher=Fraunhofer-Institut für Chemische Technologie|pages=26-1 - 26-21|archive-url=https://web.archive.org/web/20210125141313/https://apps.dtic.mil/sti/citations/ADA396885|archive-date=2021-01-25|place=Karlsruhe, Germany|book-title=2, 2-dinitro-ethene-1, 1-diamine(FOX-7)- Properties, analysis and scale-up|access-date=2021-01-25|url-status=live}}</ref> 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.<ref name="Lochert" /> 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.<ref>US Patent 6312538 - Chemical compound suitable for use as an explosive, intermediate and method for preparing the compound</ref> |
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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 (explosive)|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,<ref name="Anniyappan" /> including in Australia, India, the USA, and Sweden. |
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 (explosive)|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,<ref name="Anniyappan" /> including in Australia, India, the USA, and Sweden.<ref name=":0" /><ref name="Lochert" /><ref name=":1" /><ref name=":2" /> |
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== References == |
== References == |
Revision as of 17:08, 24 February 2021
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Names | |
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IUPAC name
2,2-dinitroethene-1,1-diamine
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Other names
FOX-7
FOX7 | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.130.630 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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 dipolar aprotic solvents such as dimethyl sulfoxide (DMSO), N,N-Dimethylformamide (DMF), and N-Methyl-2-pyrrolidone (NMP)[1] | |
Hazards | |
GHS labelling: | |
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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).
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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 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
- ^ 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 & Technology Organization. DSTO-TR-1238. Archived (PDF) from the original on 2021-01-25. Retrieved 2021-01-25.
{{cite tech report}}
: CS1 maint: date and year (link) - ^ US Patent 6340780 - Method of preparing salts of dinitromethane
- ^ 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.
- ^ 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
- ^ 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.
- ^ 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.
{{cite tech report}}
: CS1 maint: date and year (link) - ^ 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. Archived from the original on 2021-01-25. Retrieved 2021-01-25.
- ^ US Patent 6312538 - Chemical compound suitable for use as an explosive, intermediate and method for preparing the compound
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.