Xylitol pentanitrate
Names | |
---|---|
IUPAC name
1,2,3,4,5-Pentakis-nitrooxy-pentane
| |
Identifiers | |
3D model (
JSmol ) |
|
ChemSpider | |
PubChem CID
|
|
| |
| |
Properties | |
C5H7N5O15 | |
Molar mass | 377.131 g·mol−1 |
Density | 1.852 g/cm3 |
Melting point | 45.5 °C (114 °F; 318 K) |
Boiling point | 163-185 °C (346 - 358 °F; 436 - 458 K) (Decomposes) |
Solubility | Soluble in ethanol, toluene, chloroform, acetone[1] |
log P | 3.42[2] |
Structure | |
Monoclinic [3] | |
Explosive data | |
Shock sensitivity | 4.5 J[3] |
Friction sensitivity | 18 N [3] |
Detonation velocity | 7,100 m/s |
Hazards | |
GHS labelling: | |
167 °C (333 °F; 440 K) [3] | |
Lethal dose or concentration (LD, LC): | |
LC50 (median concentration)
|
148 μM (in splenocytes)[2] |
Related compounds | |
Related compounds
|
Xylitol Erythritol tetranitrate Pentaerythritol tetranitrate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Xylitol pentanitrate (XPN) is a
Properties
At room temperature XPN exists as a white crystalline solid. When heated to 163 °C, liquid xylitol pentanitrate begins to crackle and produce a dark vapour. When decomposed, a gram of XPN produces 200 mL of gas, which makes it a high performance explosive.[3]
Rotter impact analysis of XPN found a figure of insensitiveness of 25 (RDX = 80). XPN displayed a similar sensitivity to static discharge to ETN and PETN.[3]
Synthesis
Xylitol pentanitrate is formed by reaction of xylitol pentaacetate with fuming nitric acid and glacial acetic acid.[5]
Complete oxidation
Much like ETN, XPN has a positive oxygen balance, which means the carbon and hydrogen in the molecule can be fully oxidized without another oxidizing agent being added.
The decomposition of four molecules of XPN releases three O2. The free oxygen molecules can be used to oxidize an added metal dust or negative oxygen balanced explosive like TNT.
See also
- Nitroglycerine
- Xylitan trinitrate – used as plasticizer in propellants similarly to nitroglycerine
- Mannitol hexanitrate
References
- S2CID 221643415.
- ^ a b Šarlauskas, Jonas; KrikŠtopaitis, Kastis; MiliukienĖ, Valė; ČĖnas, Narimantas; AnuseviČius, Žilvinas; ŠaikŪnas, Algirdas (2011). "Investigation on the Electrochemistry and Cytotoxicity of Organic Nitrates and Nitroamines". Central European Journal of Energetic Materials. 8: 15–24.
- ^ S2CID 109872121.
- ISBN 978-3-11-067255-8.
- ^ ISSN 0008-4042.
- .
- S2CID 102678177.
External links
- Media related to Xylitol pentanitrate at Wikimedia Commons