Xylitol pentanitrate

Xylitol pentanitrate
Names
	IUPAC name 1,2,3,4,5-Pentakis-nitrooxy-pentane
Identifiers
CAS Number	147-16-0;
3D model (JSmol)	Interactive image;
ChemSpider	29852477 ;
PubChem CID	91383061;
	InChI InChI=1S/C5H7N5O15/c11-6(12)21-1-3(23-8(15)16)5(25-10(19)20)4(24-9(17)18)2-22-7(13)14/h3-5H,1-2H2/t3-,4+,5+ Key: STNMPEICBMBFAP-SCDXWVJYSA-N ; InChI=1/C5H7N5O15/c11-6(12)21-1-3(23-8(15)16)5(25-10(19)20)4(24-9(17)18)2-22-7(13)14/h3-5H,1-2H2/t3-,4+,5+ Key: STNMPEICBMBFAP-SCDXWVJYBV;
	SMILES C([C@H]([C@@H]([C@H](CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-];
Properties
Chemical formula	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
log P	3.42
Structure
Crystal structure	Monoclinic
Explosive data
Shock sensitivity	4.5 J
Friction sensitivity	18 N
Detonation velocity	7,100 m/s
Hazards
	GHS labelling:
Pictograms
Autoignition; temperature	167 °C (333 °F; 440 K)
	Lethal dose or concentration (LD, LC):
LC50 (median concentration)	148 μM (in splenocytes)
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). (what is ?) Infobox references

Xylitol pentanitrate (XPN) is a nitrated ester primary explosive^[3]^[4] first synthesized in 1891 by Gabriel Bertrand.^[5]^[6] Law enforcement has taken an interest in XPN along with erythritol tetranitrate (ETN) and pentaerythritol tetranitrate (PETN) due to their ease of synthesis, which makes them accessible to amateur chemists and terrorists.^[7]^[8]

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 nitration of xylitol pentaacetate. Nowadays, fuming nitric acid and glacial acetic acid is often used,^[9] but Bertrand originally employed a cheaper nitrating agent, the mixture of nitric and sulfuric acids (he called it mélange nitrosulfurique, the common English name is "mixed acid").^[6]

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. ${\ce {4C5H7N5O15 ->[\Delta] 20CO2 + 14H2O + 10N2 + 3O2}}$

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.

References

^ 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: 110472. doi:10.1016/j.forsciint.2020.110472. PMID 32919164. 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.
^ ^a ^b ^c ^d ^e ^f ^g 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. doi:10.1002/prep.201800337. ISSN 0721-3115. S2CID 109872121.
^ Klapötke, Thomas M. (2021-01-18). "X". O-Z. De Gruyter. pp. 2027–2030. doi:10.1515/9783110672558-019. ISBN 978-3-11-067255-8.
^ Wright, I. G.; Hayward, L. D. (1960). "The Pentitol Pentanitrates". Canadian Journal of Chemistry. 38 (2): 316–319. doi:10.1139/v60-045. ISSN 0008-4042.
^ ^a ^b Bertrand, G. (20 May 1891). "Sur la constitution de la xylite et du xylose". Bulletin de la Société chimique de Paris (in French). V (10). Paris: L. Hachette: 740.
^ Yan, Qi-Long; Künzel, Martin; Zeman, Svatopluk; Svoboda, Roman; Bartošková, Monika (2013). "The effect of molecular structure on thermal stability, decomposition kinetics and reaction models of nitric esters". Thermochimica Acta. 566: 137–148. Bibcode:2013TcAc..566..137Y. doi:10.1016/j.tca.2013.05.032.
^ Dong, Jun; Yan, Qi-Long; Liu, Pei-Jin; He, Wei; Qi, Xiao-Fei; Zeman, Svatopluk (2018). "The correlations among detonation velocity, heat of combustion, thermal stability and decomposition kinetics of nitric esters". Journal of Thermal Analysis and Calorimetry. 131 (2): 1391–1403. doi:10.1007/s10973-017-6706-5. ISSN 1388-6150. S2CID 102678177.
^ Wright, I. G.; Hayward, L. D. (1960). "The Pentitol Pentanitrates". Canadian Journal of Chemistry. 38 (2): 316–319. doi:10.1139/v60-045. ISSN 0008-4042.

External links

Media related to Xylitol pentanitrate at Wikimedia Commons

[Stark_2020-1] 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: 110472. doi:10.1016/j.forsciint.2020.110472. PMID 32919164. S2CID 221643415.

[Sarlauskas-2] 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.

[Stark_2019-3] ^ ^a ^b ^c ^d ^e ^f ^g 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. doi:10.1002/prep.201800337. ISSN 0721-3115. S2CID 109872121.

[Klapotke-4] Klapötke, Thomas M. (2021-01-18). "X". O-Z. De Gruyter. pp. 2027–2030. doi:10.1515/9783110672558-019. ISBN 978-3-11-067255-8.

[Wright-5] Wright, I. G.; Hayward, L. D. (1960). "The Pentitol Pentanitrates". Canadian Journal of Chemistry. 38 (2): 316–319. doi:10.1139/v60-045. ISSN 0008-4042.

[:0-6] Bertrand, G. (20 May 1891). "Sur la constitution de la xylite et du xylose". Bulletin de la Société chimique de Paris (in French). V (10). Paris: L. Hachette: 740.

[Yan-7] Yan, Qi-Long; Künzel, Martin; Zeman, Svatopluk; Svoboda, Roman; Bartošková, Monika (2013). "The effect of molecular structure on thermal stability, decomposition kinetics and reaction models of nitric esters". Thermochimica Acta. 566: 137–148. Bibcode:2013TcAc..566..137Y. doi:10.1016/j.tca.2013.05.032.

[Dong-8] Dong, Jun; Yan, Qi-Long; Liu, Pei-Jin; He, Wei; Qi, Xiao-Fei; Zeman, Svatopluk (2018). "The correlations among detonation velocity, heat of combustion, thermal stability and decomposition kinetics of nitric esters". Journal of Thermal Analysis and Calorimetry. 131 (2): 1391–1403. doi:10.1007/s10973-017-6706-5. ISSN 1388-6150. S2CID 102678177.

[Wright2-9] Wright, I. G.; Hayward, L. D. (1960). "The Pentitol Pentanitrates". Canadian Journal of Chemistry. 38 (2): 316–319. doi:10.1139/v60-045. ISSN 0008-4042.

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