Trinitroazetidine
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| General | ||||||||||
| Surname | 1,3,3-trinitroazetidine | |||||||||
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| Molecular formula | C 3 H 4 N 4 O 6 | |||||||||
| Brief description |
pale yellow, orthorhombic crystals |
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| properties | ||||||||||
| Molar mass | 192.09 g mol −1 | |||||||||
| Physical state |
firmly |
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| density |
1.84 g cm −3 |
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| Melting point |
101 ° C |
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| boiling point |
252 ° C (decomposition) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
1,3,3-Trinitroazetidine (TNAZ) is an energetic heterocyclic compound that is considered a possible replacement for TNT because of its low melting point (101 ° C) and its good temperature resistance (up to 240 ° C) .
Extraction and presentation
In a first stage, 1-tert-butyl-3-azetidinol is obtained by reacting epichlorohydrin with tert-butylamine , which is converted to 1,3,3-trinitroazetidine by stepwise nitration . The yield in this implementation is rather low. An alternative synthesis starts from 3-amino-1,2-propanediol, which, after introducing p-toluenesolphonyl and tert-butyldimethylsilyl protective groups, is cyclized to the corresponding azetidine derivative by means of lithium hydride . After oxidation with chromium trioxide and reaction with hydroxylamine , the intermediate compound is converted to an oxime intermediate, which is then oxidatively nitrated with nitric acid to give the trinitro target compound .
properties
1,3,3-Trinitroazetidine forms pale yellow crystals with a melting point of 101 ° C. The compound crystallizes in an orthorhombic lattice with the space group Pbca. From 240 ° C thermolysis produces the decomposition products nitrogen dioxide , nitrogen monoxide , nitrous acid , carbon dioxide and formaldehyde . The explosion characteristics are known as the heat of the explosion with 6343 kJ kg −1 , the specific energy with 1378 kJ kg −1 , the detonation velocity with 9000 m s −1 and the detonation pressure with 36.4 G Pa .
use
Experimental energetic connection for the production of highly explosive castable explosives. With its performance data it is between hexogen and octogen . But the material is much less sensitive than this.
Individual evidence
- ↑ a b c d e f Entry on TNAZ. In: Römpp Online . Georg Thieme Verlag, accessed on September 29, 2014.
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ a b c T. Axenrod, C. Watnick, H. Yazdekhasti: Synthesis of 1,3,3-trinitroazetidine in Tetrahedron Letters 34 (1993) 6677-6680. doi : 10.1016 / S0040-4039 (00) 61673-8
- ↑ a b c d Koehler, J .; Meyer, R .; Homburg, A .: Explosivstoffe , tenth, completely revised edition. Wiley-VCH, Weinheim 2008, ISBN 978-3-527-32009-7 .
- ↑ a b T. G. Archibald, R. Gilardi, K. Baum, C. George: Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine , in: J. Org. Chem. 55 (1990) 2920-2924, doi : 10.1021 / jo00296a066 .
- ↑ Y. Oyumi, TB Brill: Thermal decomposition of energetic materials 4. High-rate, in situ, thermolysis of the four, six, and eight membered, oxygen-rich, gem-dinitroalkyl cyclic nitrate mines, TNAZ, DNNC, and HNDZ in Comb. Flame 62 (1985) 225-231, doi : 10.1016 / 0010-2180 (85) 90148-8 .