1,3,5-triazido-2,4,6-trinitrobenzene

Structural formula
General
Surname	1,3,5-triazido-2,4,6-trinitrobenzene
other names	Triazidotrinitrobenzene TATNB TNTAB TNTAZB
Molecular formula	C 6 N 12 O 6
Brief description	pale yellow crystals
External identifiers / databases
CAS number 29306-57-8 PubChem 62844 ChemSpider 56578 Wikidata Q4545665
properties
Molar mass	336.14 g mol −1
Physical state	firmly
density	1.805 g cm −3
Melting point	131 ° C
solubility	almost insoluble in water, slightly soluble in alcohols, readily soluble in acetone and benzene
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,3,5-Triazido-2,4,6-trinitrobenzene is an aromatic, highly explosive compound that belongs to the group of organic nitro compounds and azides .

history

The compound was first synthesized in 1924 by Oldrich Turek.

Extraction and presentation

The synthesis succeeds by reacting 1,3,5-trichloro-2,4,6-trinitrobenzene with sodium azide . The starting compound can be prepared by the nitration of 1,3,5-trichlorobenzene using a mixture of nitric acid and fuming sulfuric acid are manufactured as a strong nitrating reagent at high temperatures. In a second synthetic route, the target compound is obtained by nitration of 1,3,5-triazido-2,4-dinitrobenzene.

properties

Physical Properties

1,3,5-Triazido-2,4,6-trinitrobenzene is a crystalline solid that melts at 131 ° C. It crystallizes in a monoclinic crystal lattice P 2 ₁ / c. It is a strongly endothermic compound. The heat of formation is 765.8 kJ mol ⁻¹ , the heat of combustion 3200 kJ mol ⁻¹ .

Chemical properties

The compound slowly decomposes, even at low temperatures, with the elimination of nitrogen to form benzotrifuroxane . The reaction proceeds quantitatively within 14 hours at 100 ° C. At 50 ° C. a conversion of 50% is achieved after 190 days, at 35 ° C. after 600 days a conversion of 16% and at 20 ° C. after 1200 days a conversion of about 2.8%. The decomposition is not autocatalytic . In solution in m-xylene , decomposition according to a first-order time law was observed. The half-lives are 340 min at 70 ° C, 89 min at 85 ° C and 900 s at 100 ° C.

The compound can decompose explosively. It is highly sensitive to impact and only weakly sensitive to friction .

Table with important explosion-relevant properties:

Oxygen balance	−28.6%
Nitrogen content	50.0%
Normal gas volume	800 l kg −1
Explosion heat	5693 kJ kg −1 (H 2 O (l))
Specific energy	1666 kJ kg −1 (68.1 mt / kg)
Lead block bulge	47.0 cm 3 g −1
Sensitivity to impact	5 Nm

use

1,3,5-Triazido-2,4,6-trinitrobenzene was seen as a possible replacement of the initial explosive mercury fulminate in detonators , detonators and the like. Because of the low thermal stability and thus storage stability, no commercial application could gain acceptance.

literature

• Robert Matyas, Jiri Pachman: Primary Explosives. Springer, 2013, ISBN 978-3-642-28435-9 , pp. 118–121.

Individual evidence

1. ↑ ^{a b c d e f g h} O. Turek: Le 2,4,6-trinitro-1,3,5-triazido-benzene, new explosif d'amorcage . In: Chimie et industrie . tape 26 , 1931, p. 781-794 .
2. ↑ ^{a b c d e f g h} O. Turek: 1,3,5-Triazido-2,4,6-trinitrobenzene, nova inicialna vybusina . In: Chemicky obzor . No. 7 , 1932, pp. 76-79; 97-104 .
3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
4. ↑ ^{a b} Patent GB298981 : A method of producing 2,4,6-trinitro-1,3,5-triazidobenzene. Published on 1928 , inventor: O. Turek. ‌
5. ↑ ^{a b} Patent DE498050 : Process for the production of 1,3,5-trinitro-2,4,6-triazidobenzene. Published on 1930 , inventor: O. Turek. ‌
6. ↑ AS Bailey, JR Case: 4: 6-dinitrobenzofuroxan, nitrobenzodifuroxan and benzotrifuroxan: A new series of complex-forming reagents for aromatic hydrocarbons in Tetrahedron 3 (1958) 113-131, doi: 10.1016 / 0040-4020 (58) 80003- 4 .
7. ↑ ^{a b c d} David Adam, Konstantin Karaghiosoff, Thomas M. Klapötke , Gerhard Holl, Manfred Kaiser: Triazidotrinitro Benzene: 1,3,5- (N3) 3-2,4,6- (NO2) 3C6 . In: Propellants, Explosives, Pyrotechnics . tape 27 , no. 1 , 2002, p. 7-11 , doi : 10.1002 / 1521-4087 (200203) 27: 1 <7 :: AID-PREP7> 3.0.CO; 2-J .
8. ↑ Yu M. Burov, GM Nazin, GB Manelis: Retardation of monomolecular reactions in the solid phase . In: Russian Chemical Bulletin . tape 48 , no. 7 , July 1999, p. 1250-1254 , doi : 10.1007 / BF02495284 .
9. ↑ BL Korsunskii, TA Apina: Kinetics of the thermal decomposition of 1,3,5-triazido-2,4,6-trinitrobenzene in solution . In: Bulletin of the Academy of Sciences of the USSR, Division of chemical science . tape 20 , no. 9 September 1971, p. 1971–1973 , doi : 10.1007 / BF00854439 .
10. ↑ ^{a b c d e f g h} J. Köhler, R. Meyer, A. Homburg: Explosivstoffe . 10th, completely revised edition, Wiley-VCH, Weinheim 2008, p. 324, ISBN 978-3-527-32009-7 .
11. ↑ ^{a b} B. T. Fedoroff, OE Sheffield, SM Kaye: Encyclopedia of Explosives and Related Items. Picatinny Arsenal, New Jersey (1960-1983).
12. ↑ patent GB298629 : Improvements in and connected with explosive charges for detonators, percussion caps, boosters, detonating fuses, projectiles and the like. Published on 1927 , inventor: O. Turek. ‌
13. ↑ Patent DE494289 : Process for the production of explosive charges for detonators, detonators, detonation fuses and the like. Like. Published on 1928 , inventor: O. Turek. ‌
14. ↑ Patent US2111719 : Ignition mixture for percussion caps of all kind, small munitions, and primers. Published on 1938 , inventor: B. Zielinski. ‌
15. ^ T. Urbanski: Chemistry and Technology of Explosives. PWN — Polish Scientific Publisher, Warsaw 1967.