FOX-7: Difference between revisions

FOX-7
Names
	IUPAC name 2,2-Dinitroethene-1,1-diamine
	Other names FOX-7; FOX7
Identifiers
CAS Number	145250-81-3 ;
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/h3-4H2 Key: FUHQFAMVYDIUKL-UHFFFAOYSA-N;
	SMILES N/C(N)=C([N+]([O-])=O)\[N+]([O-])=O;
Properties
Chemical formula	C2H4N4O4
Molar mass	148.08
Density	1.885 g cm−3
Melting point	238 °C (460 °F; 511 K) (decomposes)
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	>350N
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). verify (what is ?) Infobox references

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Revision as of 12:21, 25 January 2021

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

FOX-7 is similar to the insensitive chemical compound TATB, which is a benzene ring compound with three amino and three nitro groups.^[4] 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 sensitivity and chemical decay processes of FOX-7.^[5] FOX-7 is stoichiometrically identical but structurally unrelated to RDX, a benchmark explosive for sensitivity and explosive power. By various measures of sensitivity, such as dropped-weight impact, friction force, temperature of ignition, and response to heating under confinement, it is less sensitive than RDX, while having performance slightly greater than the same.^[1] FOX-7 is produced as of 2018 by EURENCO Bofors AB of Sweden,^[6] having been made in batches up to 7kg in 2001.^[7]

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.^[8] FOX-7 has been calculated to have a detonation velocity of 8,870 m/s.^[9] Charges composed of EVA-coated FOX-7 granules 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.^[1]

For 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.^[1] 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.^[10] The price is therefore predicted to fall as production scale increases. There is no current full scale use of FOX-7, but it is being tested at several military research centers. The need for less sensitive munitions is favorable, and therefore the most important incentive for testing FOX-7.

References

^ ^a ^b ^c ^d 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.{{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.
^ 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.
^ 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.
^ Sleadd, Bradley A.; Boruta, David T.; Clubb, Joseph W. (24 April 2018). Development of a CONUS manufacturing capability for FOX-7 (Technical report). National Defense Industrial Association.{{cite tech report}}: CS1 maint: date and year (link)
^ 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 2018-05-04. {{cite conference}}: Unknown parameter |booktitle= ignored (|book-title= suggested) (help)
^ 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, Karlsson et al., 2002, accessed Aug 25, 2005
^ US Patent 6312538 - Chemical compound suitable for use as an explosive, intermediate and method for preparing the compound

@@ Line 48: / Line 48: @@
 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 sensitivity and chemical decay processes of FOX-7.<ref>{{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 stoichiometrically identical but structurally unrelated to [[RDX]], a benchmark explosive for sensitivity and explosive power. By various measures of sensitivity, such as dropped-weight impact, friction force, temperature of ignition, and response to heating under confinement, it is less sensitive than 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 |via=|date=November 2001 |year=2001|url=https://apps.dtic.mil/dtic/tr/fulltext/u2/a399359.pdf}}</ref> 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. |first= |last= |author2= |title=Development of a CONUS manufacturing capability for FOX-7 |number= |institution=National Defense Industrial Association |date=24 April 2018 |year=2018}}</ref> having been made in batches up to 7kg in 2001.<ref>{{cite conference|last=Ostmark|first=Henric|last2=Bergman|first2=Helena|last3=Bemm|first3=Ulf|last4=Goede|first4=Patrick|date=6 July 2001 |title=Energetic Materials: Ignition, Combustion and Detonation|conference=32nd International Conference of ICT|publisher=Fraunhofer-Institut für Chemische Technologie|pages=26-1 - 26-21|url=https://apps.dtic.mil/sti/citations/ADA396885|archiveurl=https://archive.org/details/DTIC_ADA396885/page/n341/mode/2up|archivedate=2018-05-04|place=Karlsruhe, Germany|booktitle=2, 2-dinitro-ethene-1, 1-diamine(FOX-7)- Properties, analysis and scale-up}}</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|last=Latypov|first=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&nbsp;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], Karlsson et al., 2002, accessed Aug 25, 2005</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|last=Latypov|first=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&nbsp;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], Karlsson et al., 2002, accessed Aug 25, 2005</ref> Charges composed of [[Ethylene-vinyl acetate|EVA]]-coated FOX-7 granules 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" />
-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> The price is therefore predicted to fall as production scale increases.  There is no current full scale use of FOX-7, but it is being tested at several military research centers.  The need for less sensitive munitions is favorable, and therefore the most important incentive for testing FOX-7.
+For 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> The price is therefore predicted to fall as production scale increases.  There is no current full scale use of FOX-7, but it is being tested at several military research centers.  The need for less sensitive munitions is favorable, and therefore the most important incentive for testing FOX-7.
 == References ==

Revision as of 12:21, 25 January 2021

References

Further reading