Tetrazene
- Not to be confused with tetrazine or tetracene or tetrazene explosive
 | |
| Names | |
|---|---|
| IUPAC name
1-Tetrazene | |
| Identifiers | |
54410-57-0 (2-tetrazene)  | |
| ChemSpider | 20129521  |
| PubChem | 5463295 (2-tetrazene) |
| |
| Properties | |
| H4N4 | |
| Molar mass | 60.06 g·mol−1 |
| Related compounds | |
| Related Binary azanes |
ammonia diazane triazane |
| Related compounds |
Diazene Triazene |
| verify (what is ?) | |
| Infobox references | |
Tetrazene is a chemical compound with the molecular formula N4H4. In IUPAC nomenclature, derivatives of this compound are known collectively as tetrazenes. The most common of such derivatives is tetrazene explosive (commonly known simply as tetrazene), which is used for sensitization of priming compositions. Tetrazenes are suitable as propellants or gas-generating agents thanks to their high thermal stability and low temperature of explosion.
Properties
Tetrazene has been reported to have eleven isomers.[1] The most stable of these is the straight-chain 2-tetrazine (NH2-N=N-NH2), having a standard heat of formation at 301.3 kJ/mol. The eleven isomers can be arranged into three groups: straight-chain tetrazenes, four-membered cyclotetrazane, and three-membered cyclotriazanes. Each straight-chain tetrazene isomer possesses one N=N double bond and two N-N single bonds.[1] Tautomerizations do occur between the isomers. The ionic compound ammonium azide is also a constitutional isomer of tetrazene.
Reactions
Synthesis
Functionalized tetrazolyl-tetrazenes as energetic compounds have been synthesized by the oxidation of hydrazines.[2] In all cases the product obtained was a colorless solid. The tetrazenes synthesized via this method show no melting points, but extremely sharp decomposition points. This pattern proves that tetrazolyl-tetrazenes do not change state but will readily break down to form other nitrogen-containing compounds. The sharp decomposition point of tetrazenes is due to the lack of intermolecular interactions.
Decomposition
The decomposition of tetrazene is quite rapid around 90°C. A sample of tetrazene was heated in an oven at 90°C and its rate of thermal decomposition was monitored by infrared and ultraviolet spectroscopy.[3] The thermal decomposition reaction is autocatalytic and it is likely that the same reaction can occur at even lower temperatures, however at much slower rates.
Sensitivity to Friction
Many explosives are considered to be highly sensitive to mechanical stimuli such as impact, friction, stab, heat, static electricity, flame, etc. Since explosive compounds are subject to friction practically every time they are handled, it is of particular interest to be aware of the sensitivity to friction. The sensitivity of tetrazene was determined using a FSKM-PEx friction sensitivity tester.[4] The probability of ignition of tetrazene is 100 percent likely at 27N of frictional force.[4]
Uses
Tetrazene is often used as an explosive or detonator due to its high reactivity and sensitivity.
Instances of occupational rhinitis, dermatitis, and asthma have been reported due to prolonged exposure to tetrazene.[5] As with all chemicals it is important to handle with caution, especially knowing there is some risk associated with frictional force and tetrazene.
References
- 1 2 Li, L.-C.; Shang, J.; Liu, J.-L.; Wang, X.; Wong, N.-B. (2007). "A G3B3 study of N4H4 isomers". Journal of Molecular Structure 807 (1–3): 207–10. doi:10.1016/j.theochem.2006.12.009.
- ↑ Heppekausen, J.; Klapötke, T.; Sproll, S. (2009). "Synthesis of functionalized tetrazenes as energetic compounds". J. Org. Chem. 74 (6): 2460–6. doi:10.1021/jo802738c. PMID 19222166.
- ↑ Bird, R.; Power, A. (1978). "Thermal Decomposition of Tetrazene at 90°C" (pdf). Melbourne, Victoria: Department of Defence. MRL-R-710 AR-000-886.
- 1 2 Matyáš, R.; Šelešovský, J.; Musil, T. (2012). "Sensitivity to friction for Primary Explosives". Journal of Hazardous Materials. 213–214: 236–41. doi:10.1016/j.jhazmat.2012.01.085. PMID 22349715.
- ↑ Burge, P. S.; Hendy, M.; Hodgson, E. S. (1984). "Occupational asthma, rhinitis, and dermatitis due to tetrazene in a detonator manufacturer". Thorax 39 (6): 470–1. doi:10.1136/thx.39.6.470. PMC 459834. PMID 6235620.