FOX-7

Last updated
FOX-7
FOX7.png
Names
Preferred IUPAC name
2,2-Dinitroethene-1,1-diamine
Other names
FOX-7
FOX7
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.130.630 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 604-466-1
PubChem CID
UNII
  • 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
AppearanceBright 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:
GHS-pictogram-explos.svg GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Related Research Articles

<span class="mw-page-title-main">RDX</span> Explosive chemical compound

RDX (abbreviation of "Research Department eXplosive") or hexogen, among other names, is an organic compound with the formula (O2N2CH2)3. It is white, odorless and tasteless, widely used as an explosive. Chemically, it is classified as a nitroamine alongside HMX, which is a more energetic explosive than TNT. It was used widely in World War II and remains common in military applications.

<span class="mw-page-title-main">Explosive</span> Substance that can explode

An explosive is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An explosive charge is a measured quantity of explosive material, which may either be composed solely of one ingredient or be a mixture containing at least two substances.

<span class="mw-page-title-main">Plastic explosive</span> Type of explosive material

Plastic explosive is a soft and hand-moldable solid form of explosive material. Within the field of explosives engineering, plastic explosives are also known as putty explosives or blastics.

<span class="mw-page-title-main">TNT</span> Impact-resistant high explosive

Trinitrotoluene, more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagent in chemical synthesis, but it is best known as an explosive material with convenient handling properties. The explosive yield of TNT is considered to be the standard comparative convention of bombs and asteroid impacts. In chemistry, TNT is used to generate charge transfer salts.

<span class="mw-page-title-main">HMX</span> Chemical compound

HMX, also called octogen, is a powerful and relatively insensitive nitroamine high explosive, chemically related to RDX. The compound's name is the subject of much speculation, having been variously listed as High Melting Explosive, High-velocity Military Explosive, or High-Molecular-weight RDX.

<span class="mw-page-title-main">C-4 (explosive)</span> Variety of plastic explosive

C-4 or Composition C-4 is a common variety of the plastic explosive family known as Composition C, which uses RDX as its explosive agent. C-4 is composed of explosives, plastic binder, plasticizer to make it malleable, and usually a marker or odorizing taggant chemical. C-4 has a texture similar to modelling clay and can be molded into any desired shape. C-4 is relatively insensitive and can be detonated only by the shock wave from a detonator or blasting cap.

Polymer-bonded explosives, also called PBX or plastic-bonded explosives, are explosive materials in which explosive powder is bound together in a matrix using small quantities of a synthetic polymer. PBXs are normally used for explosive materials that are not easily melted into a casting, or are otherwise difficult to form.

A triggering sequence, also called an explosive train or a firing train, is a sequence of events that culminates in the detonation of explosives. For safety reasons, most widely used high explosives are difficult to detonate. A primary explosive of higher sensitivity is used to trigger a uniform and predictable detonation of the main body of the explosive. Although the primary explosive itself is generally a more sensitive and expensive compound, it is only used in small quantities and in relatively safely packaged forms. By design there are low explosives and high explosives made such that the low explosives are highly sensitive and high explosives are comparatively insensitive. This not only affords inherent safety to the usage of explosives during handling and transport, but also necessitates an explosive triggering sequence or explosive train. The explosive triggering sequence or the explosive train essentially consists of an 'initiator', an 'intermediary' and the 'high explosive'.

Octanitrocubane (molecular formula: C8(NO2)8) is a high explosive that, like TNT, is shock-insensitive (not readily detonated by shock). The octanitrocubane molecule has the same chemical structure as cubane (C8H8) except that each of the eight hydrogen atoms is replaced by a nitro group (NO2).

Insensitive munitions are munitions that are designed to withstand stimuli representative of severe but credible accidents. The current range of stimuli are shock, heat and adjacent detonating munitions. A munition can have its vulnerability reduced by a number of means used on their own or in combination such as a reduced vulnerability energetic material, design features, additions or changes to packaging etc. The munition must still retain its terminal effect and performance within acceptable parameters.

The Composition C family is a family of related US-specified plastic explosives consisting primarily of RDX. All can be moulded by hand for use in demolition work and packed by hand into shaped charge devices. Variants have different proportions and plasticisers and include composition C-2, composition C-3, and composition C-4.

<span class="mw-page-title-main">TATB</span> Chemical compound

TATB, triaminotrinitrobenzene or 2,4,6-triamino-1,3,5-trinitrobenzene is an aromatic explosive, based on the basic six-carbon benzene ring structure with three nitro functional groups (NO2) and three amine (NH2) groups attached, alternating around the ring.

This is a compilation of published detonation velocities for various high explosive compounds. Detonation velocity is the speed with which the detonation shock wave travels through the explosive. It is a key, directly measurable indicator of explosive performance, but depends on density which must always be specified, and may be too low if the test charge diameter is not large enough. Especially for little studied explosives there may be divergent published values due to charge diameter issues. In liquid explosives, like nitroglycerin, there may be two detonation velocities, one much higher than the other. The detonation velocity values presented here are typically for the highest practical density which maximizes achievable detonation velocity.

High Energy Materials Research Laboratory (HEMRL) is one of the premier laboratories of the Defence Research and Development Organisation (DRDO) located in Pune Maharashtra. Main area of works of the lab include research and development of high energy materials and related technologies. HEMRL is organised under the Armaments Directorate of DRDO. The current director of the lab is Dr A P Dash.

<span class="mw-page-title-main">Ammonium dinitramide</span> Chemical compound

Ammonium dinitramide (ADN) is the ammonium salt of dinitraminic acid. ADN decomposes under heat to leave only nitrogen, oxygen, and water. The ions are the ammonium ion NH4+ and the dinitramide N(NO2)2−.

Explosive materials are produced in numerous physical forms for their use in mining, engineering, or military applications. The different physical forms and fabrication methods are grouped together in several use forms of explosives.

<span class="mw-page-title-main">TEX (explosive)</span> Chemical compound

TEX is a dense nitramine high explosive, that derives from the very powerful and sensitive high explosive CL-20. Though related to CL-20 in that is shares the same cage structure, TEX is more easily synthesized in good yield from inexpensive starting materials. Unlike CL-20, TEX is friction insensitive, bears a low impact sensitivity, and possesses a very low shock sensitivity and large critical diameter, making it an interesting explosive filler for insensitive munitions. Its systematic name, 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,9.03,11]-dodecane derives from its tetracyclic structure.

<span class="mw-page-title-main">Nickel hydrazine nitrate</span> Chemical compound

Nickel hydrazine nitrate (NHN), (chemical formula: [Ni(N2H4)3](NO3)2 is an energetic material having explosive properties in between that of primary explosive and a secondary explosive. It is a salt of a coordination compound of nickel with a reaction equation of 3N2H4·H2O + Ni(NO3)2 →〔Ni(N2H4)3〕(NO3)2 ＋ 3H2O

Guanylurea dinitramide is a novel insensitive high explosive.

References

  1. 1 2 3 4 5 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. 1 2 3 4 5 6 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. ↑ USpatent 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 CrystC54: 1997-1999. doi : 10.1107/S0108270198007987.
  5. 1 2 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. 1 2 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. 1 2 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. ↑ USpatent 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

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