Chemistry:1,3,3-Trinitroazetidine
{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = | ImageFile = 1,3,3-Trinitroazetidin.svg | ImageSize = 150px | ImageFile1 = | ImageSize1 = | ImageAlt1 = | PIN = 1,3,3-Trinitroazetidine | OtherNames = TNAZ | Section1 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers
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- InChI=1S/C3H4N4O6/c8-5(9)3(6(10)11)1-4(2-3)7(12)13/h1-2H2Key: ZCRYIJDAHIGPDQ-UHFFFAOYSA-N
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- C1C(CN1[N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-]
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| C3H4N4O6
|- | Molar mass
| 192.087 g·mol−1
|- | Appearance | Pale yellow crystals |-
| Density | 1.84 g/cm3 |- | Melting point | 101[1] °C (214 °F; 374 K)
|- | Boiling point | 252[1] °C (486 °F; 525 K)
|- | Section3 = | Section4 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Structure
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| Orthorhombic |- | Section6 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Explosive data
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| Detonation velocity
| 9597 m/s[2]
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1,3,3-Trinitroazetidine (TNAZ) is a highly energetic heterocyclic compound that has been considered as a potential replacement for TNT because of its low melting point (101 °C) and good thermal stability (up to 240 °C). TNAZ was first synthesized by Archibald et al. in 1990.[3] Several synthesis routes are known, and bulk production of several hundred kilogram batches has been demonstrated at Los Alamos National Laboratory.[4][1][5]
Properties
The compound crystallizes in an orthorhombic lattice with the space group Pbca. Thermolysis occurs starting around 240 °C - 250 °C with decomposition products that include nitrogen dioxide, nitric oxide, nitrous acid, carbon dioxide, and formaldehyde. It has a heat of decomposition of 6343 kJ/kg, and a detonation pressure of 36.4 GPa.[6]
References
- ↑ 1.0 1.1 1.2 Viswanath, Dabir S.; Ghosh, Tushar K.; Boddu, Veera M. (2018). "1,3,3-Trinitroazetidine (TNAZ)" (in en). Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties. pp. 293–307. doi:10.1007/978-94-024-1201-7_11. ISBN 978-94-024-1199-7.
- ↑ Template:Cite tech report
- ↑ Archibald, T. G; Gilardi, Richard; Baum, K; George, Clifford (1990). "Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine". The Journal of Organic Chemistry 55 (9): 2920–2924. doi:10.1021/jo00296a066.
- ↑ Coburn, Michael D.; Hiskey, Michael A.; Archibald, Thomas G. (January 1998). "Scale-up and waste-minimization of the Los Alamos process for 1,3,3-trinitroazetidine (TNAZ)". Waste Management 17 (2–3): 143–146. doi:10.1016/S0956-053X(97)10013-7. Bibcode: 1998WaMan..17..143C.
- ↑ Jalový, Zdenek; Zeman, Svatopluk; Suceska, Muhamed; Vávra, Pave; Dudek, Kamil; Rajic, Masa (1 June 2001). "1,3,3-trinitroazetidine (TNAZ). Part I. Syntheses and properties" (in en). Journal of Energetic Materials 19 (2): 219–239. doi:10.1080/07370650108216127. ISSN 0737-0652. Bibcode: 2001JEnM...19..219J.
- ↑ Axenrod, Theodore; Watnick, Clara; Yazdekhasti, Hamid; Dave, Paritosh R (1993). "Synthesis of 1,3,3-trinitroazetidine". Tetrahedron Letters 34 (42): 6677–6680. doi:10.1016/S0040-4039(00)61673-8.
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