Xylitol pentanitrate

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Xylitol pentanitrate
Names
IUPAC name
1,2,3,4,5-Pentakis-nitrooxy-pentane
Other names
Penta-O-nitro-xylitol
XPN
Properties
C5H7N5O15
Molar mass 377.131 g/mol
Appearance White solid
Odor Odorless
Density 1.852 g/cm3
Melting point 45.5 °C (113.9 °F; 318.6 K) [1]
Boiling point 163–185 °C (325–365 °F; 436–458 K) (decomposes)
Almost insoluble
Solubility Soluble in acetone, chloroform, ethanol, toluene
Vapor pressure ~0 mmHg
Hazards
Safety data sheet None
Related compounds
Related compounds
Erythritol tetranitrate
Pentaerythritol tetranitrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Xylitol pentanitrate (XPN) is an organic chemical compound, a nitrated ester primary explosive.

Properties

Chemical

Much like ETN, XPN has a positive oxygen balance, which means the carbon and oxygen in the molecule can be fully oxidized without another oxidizing agent being added:

4 C5H7N5O15 → 20 CO2 + 14 H2O + 10 N2 + 3 O2

Physical

Xylitol pentanitrate is a white crystalline solid, with a relative low melting point. It is almost insoluble in water, but much more soluble in organic solvents, like alcohol, acetone or chloroform.[2]

Explosive

XPN is a powerful explosive. It has moderate sensitivity to shock and friction. Its detonation velocity has been determined to be 7,100 m/s.

Rotter impact analysis of XPN found a figure of insensitiveness of 25 (RDX = 80). XPN displayed a similar sensitivity to electric static discharge to ETN and PETN.[3]

Availability

Xylitol pentanitrate is not sold by chemical suppliers and has to be made in situ.

Preparation

Xylitol pentanitrate can be obtained from the reaction of xylitol pentaacetate with fuming nitric acid and glacial acetic acid.[4]

Direct nitration of xylitol is an easy route, but further purification is required, as the resulting product tends to come across as a viscous liquid.

It's recommended to obtain the final product as powder rather than large crystals, as it's less sensitive.

Projects

  • Make blasting charge
  • Make heart medicine

Handling

Safety

Xylitol pentanitrate is sensitive to strong shock and friction, and may explode. If ingested, it results in severe headaches, due to being a strong vasodilator, property seen in other nitrated organic compounds.

Storage

XPN is best be stored in closed non-metal spark free containers, preferably in special cabinets. For safety and legal reasons avoid storing it. Try to use it as soon as you make it.

Disposal

XPN can be neutralized with an excess solution of sodium hydroxide, at low temperatures.

References

  1. Wright; Hayward; Canadian Journal of Chemistry; vol. 38; (1960); p. 316
  2. Stark, Kelly-Anne S.; Gascooke, Jason R.; Gibson, Christopher T.; Lenehan, Claire E.; Bonnar, Callum; Fitzgerald, Mark; Kirkbride, K. Paul (November 2020). "Xylitol pentanitrate – Its characterization and analysis". Forensic Science International. 316
  3. Stark, Kelly‐Anne S.; Alvino, Jason F.; Kirkbride, K. Paul; Sumby, Christopher J.; Metha, Gregory F.; Lenehan, Claire E.; Fitzgerald, Mark; Wall, Craig; Mitchell, Mark; Prior, Chad (2019). "Crystal Structure, Sensitiveness and Theoretical Explosive Performance of Xylitol Pentanitrate (XPN)". Propellants, Explosives, Pyrotechnics. 44 (5): 541–549
  4. Wright, I. G.; Hayward, L. D. (1960). "THE PENTITOL PENTANITRATES". Canadian Journal of Chemistry. 38 (2): 316–319

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