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{{chembox |
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| verifiedrevid = 393868865 |
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| verifiedrevid = 441076766 |
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| ImageFile = FOX7.png |
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| ImageFile = FOX7.png |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| IUPACName = 2,2-Dinitroethene-1,1-diamine |
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| PIN = 2,2-Dinitroethene-1,1-diamine |
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| OtherNames = FOX-7<br>FOX7 |
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| OtherNames = FOX-7<br>FOX7 |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 145250-81-3 |
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| CASNo = 145250-81-3 |
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| PubChem = |
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| ChemSpiderID = 467536 |
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| SMILES = N/C(N)=C(()=O)\()=O |
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| PubChem = 536770 |
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| EC_number = 604-466-1 |
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| UNII = 3B2KYV7C3F |
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| StdInChI = 1S/C2H4N4O4/c3-1(4)2(5(7)8)6(9)10/h3-4H2 |
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| StdInChIKey = FUHQFAMVYDIUKL-UHFFFAOYSA-N |
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| SMILES = N/C(N)=C(()=O)\()=O |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>2</sub>H<sub>4</sub>N<sub>4</sub>O<sub>4</sub> |
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| Formula = C<sub>2</sub>H<sub>4</sub>N<sub>4</sub>O<sub>4</sub> |
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| MolarMass = 148.08 |
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| MolarMass = 148.08 |
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| Appearance = Bright yellow crystalline powder<ref name="Anniyappan" /> |
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| Appearance = |
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| Density = 1.885 g cm<sup>-3</sup> |
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| Density = 1.885 g cm<sup>−3</sup> |
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| MeltingPtC = 238 |
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| MeltingPt = 238 °C (]) |
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| MeltingPt_notes = (]) |
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| BoilingPt = |
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| Solubility = |
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| BoilingPt = |
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| Solubility = Soluble in polar aprotic solvents such as ], ], and ]<ref name="Anniyappan" /> |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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| GHSPictograms = {{GHS01}}{{GHS02}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|201|228|302}} |
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| PPhrases = {{P-phrases|210|230|240|241|250|264|270|280|301+312|330|370+378|370+380|372|373|401|501}} |
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| Section6 = {{Chembox Explosive |
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|Section6={{Chembox Explosive |
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| ShockSens = |
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| ShockSens = |
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| FrictionSens = |
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| FrictionSens = >350N<ref name="Lochert" /> |
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| ExplosiveV = 8870 m/s at density 1.885 g cm<sup>-3</sup> (estimated)<br>8335 m/s at density 1.756 g cm<sup>-3</sup> (measured, small scale testing) |
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| DetonationV = 8870 m/s at density 1.885 g cm<sup>−3</sup> (estimated)<br>8335 m/s at density 1.756 g cm<sup>−3</sup> (measured, small-scale testing) |
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| REFactor = |
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'''FOX-7''' or '''1,1-diamino-2,2-dinitroethylene''' '''(DADNE)'''<ref>{{cite patent|country=US|status=patent|number=6340780|title=Method of preparing salts of dinitromethane|invent1=Nikolai Latypov|invent2=Ulf Wellmar|invent3=Abraham Langlet|assign=Swedish Defence Research Agency|gdate=2002-01-22}}</ref> is an ] compound. It was first synthesized in 1998 by the ] (FOA).<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> According to other information it was synthesized in the USSR in 1990. The name FOX-7 is derived from the acronym of the ], with the ''I'' replaced by an ''X'' to indicate an explosive, as in ] and ].<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''' or '''1,1-diamino-2,2-dinitroethene''' '''(DADNE)''' is an ] compound. It was first synthesized in 1998 by the ] (]). |
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<ref name="dsto">, Dorsett, 2000, accessed Aug 25, 2005</ref> |
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FOX-7 is similar to the insensitive chemical compound ], which is a ] ring compound with three ] and three ]s. FOX-7 has a two-carbon backbone rather than a ] ring, but the ] and ] groups have similar effects in both cases according to published reports on sensitivity and chemical decay processes of FOX-7. FOX-7 is today produced by Eureco ] AB in Sweden. |
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FOX-7 is similar to the insensitive chemical compound ], which is a ] ring compound with three ] and three ]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 ] 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 ] identical (but structurally unrelated)<ref name="Lochert" /> to the explosives and propellants ] and ], 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 tech report |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 |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 ] is as high as ], and nearly pure FOX-7 based ]s are slightly superior to ].<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 ] of 8,870 m/s.<ref> {{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 ]-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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Its explosive properties appear extremely favorable; in addition to its insensitive properties, the detonation velocity of mixtures of 80% FOX-7 plus ] are as high as ], and nearly pure FOX-7 based ]s are slightly superior to ]. |
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<ref>, Karlsson et al., 2002, accessed Aug 25, 2005</ref> FOX-7 has been calculated to have a ] of 8,870 m/s.<ref name="dsto"/> |
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FOX-7 is produced as of 2018 by EURENCO ] AB of Sweden,<ref name=":1">{{cite tech report|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|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>{{cite patent|country=US|status=patent|number=6312538|title=Chemical compound suitable for use as an explosive, intermediate and method for preparing the compound|invent1=Nikolai Latypov|invent2=Ulf Wellmar|invent3=Abraham Langlet|assign=Swedish Defence Research Agency|gdate=2001-11-06}}</ref> |
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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. 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 munition is the most important driver for testing FOX-7. |
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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 ], one of the most powerful explosives and propellants in use, unlike other insensitive high explosives under investigation, such as TATB, ], ], 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 == |
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== References == |
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{{reflist}} |
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<references/> |
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== Further reading == |
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*{{cite journal|doi=10.1021/jp010289m|title=Classical and Quantum-Mechanical Studies of Crystalline FOX-7 (1,1-Diamino-2,2-dinitroethylene)|year=2001|last1=Sorescu|first1=Dan C.|last2=Boatz|first2=Jerry A.|last3=Thompson|first3=Donald L.|journal=The Journal of Physical Chemistry A|volume=105|issue=20|pages=5010|bibcode=2001JPCA..105.5010S}} |
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*{{cite journal|doi=10.1021/ic052150m|title=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|year=2006|last1=Evers|first1=Jürgen|last2=Klapötke|first2=Thomas M.|last3=Mayer|first3=Peter|last4=Oehlinger|first4=Gilbert|last5=Welch|first5=Jan|journal=Inorganic Chemistry|volume=45|issue=13|pages=4996–5007|pmid=16780321}} |
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*{{Cite encyclopedia |title=Nitroaliphatic Compounds |encyclopedia=Encyclopedia of Oxidizers |publisher=De Gruyter |last=Schmidt |first=Eckart W. |date=2022 |pages=2304-2326 |doi=10.1515/9783110750294-016 |isbn=978-3-11-075029-4 |chapter=1,1‑Diamino-2,2‑Dinitroethene}} |
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