PETN

From Wikipedia, the free encyclopedia

PETN
Identifiers
CAS number	[78-11-5]
PubChem	6518
SMILES	C(C(CO[N+](=O)[O-])(CO[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-]
Properties
Molecular formula	C5H8N4O12
Molar mass	316.137 g/mol
Density	1.77 g/cm3 at 20 °C
Melting point	141.3 °C, 414 K, 286 °F
Explosive data
Shock sensitivity	Medium
Friction sensitivity	Medium
Explosive velocity	8400 m/s
RE factor	1.66
Hazards
Autoignition temperature	190 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Pentaerythritol tetranitrate (PETN, also known as pentrite, or rarely and primarily in German as nitropenta) is one of the most powerful high explosives known, with a relative effectiveness factor (R.E. factor) of 1.66.

Contents 1 Uses 2 Production 3 Pollution 4 History 5 See also 6 References 7 External links

[edit] Uses

The most obvious use of PETN is as an explosive. It is more sensitive to shock or friction than TNT or tetryl, and it is never used alone as a booster. It is primarily used in booster and bursting charges of small caliber ammunition, in upper charges of detonators in some land mines and shells, and as the explosive core of detonation cord.^{[citation needed]}

Apart from this, PETN is used as a vasodilator, similar to nitroglycerin. The medicine for heart diseases "Lentonitrat" is pure PETN.^[1]

[edit] Production

PETN's preparation involves the nitration of pentaerythritol with a mixture of concentrated nitric and sulfuric acid. The preferred method of nitration is the ICI method, which utilizes concentrated nitric acid (98%+) alone, as mixed acid can create unstable sulfonated by-products.

C(CH₂OH)₄ + 4HNO₃ → C(CH₂ONO₂)₄ + 4H₂O

[edit] Pollution

PETN does not occur naturally, so the production of this kind of compound without detonation may lead to contamination of the environment^{[citation needed]}. PETN is subject to biodegradation in untreated or unpreserved urine and feces^{[citation needed]}. There also have been some reports of its degradation by bacteria, whose PETN reductase denitrates PETN into trinitrates and then dinitrates (French et al., 1996). The last compound shown in the pathway, pentaerythritol dinitrate, is degraded further to unknown products^{[citation needed]}.

[edit] History

Penthrite was first synthesized in 1891 by Tollens and Wiegand by nitration of pentaerythritol. In 1912, after being patented by the German government, the production of PETN started. PETN was used by the German army in World War I. ^[2] PETN is also one of the ingredients in Semtex plastic explosive.

[edit] See also

• Pentolite
• Semtex
• RDX
• TNT

[edit] References

• Cooper, Paul W., Explosives Engineering, New York: Wiley-VCH, 1996. ISBN 0-471-18636-8

1. ^ Russek H. I. (1966). "The therapeutic role of coronary vasodilators: glyceryl trinitrate, isosorbide dinitrate, and pentaerythritol tetranitrate.". American Journal of Medical Science 252 (1): 9-20. doi:10.1097/00000441-196607000-00002. PMID 4957459. 
2. ^ Stettbacher, Alfred (1933). Die Schiess- und Sprengstoffe. Barth, 459. 

[edit] External links

• Prva Iskra Namenska AD (Serbia)

v • d • e Vasodilators used in cardiac diseases (C01D) Nitrates Glyceryl trinitrate • Isosorbide dinitrate • Isosorbide mononitrate • Molsidomine • Pentaerythritol tetranitrate Quinolone vasodilators Flosequinan Others Itramin tosilate • Prenylamine • Oxyfedrine • Benziodarone • Carbocromen • Hexobendine • Etafenone • Heptaminol • Imolamine • Dilazep • Trapidil • Molsidomine • Efloxate • Cinepazet • Cloridarol • Nicorandil • Linsidomine • Nesiritide • Gapicomine