PETN

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PETN chemical structure
PETN

1,3-Dinitrato-2,2-bis
(nitratomethyl)propane
IUPAC name
Chemical formula C5H8N4O12
Molar mass 316.14 g/mol
Shock sensitivity Medium
Friction sensitivity Medium
Density 1.773 g/cm³ at 20 °C
Explosive velocity 8,400 m/s
RE factor 1.66
Melting point 141.3 °C
Autoignition temperature Decomposes at 190 °C
Appearance Odourless white
crystalline solid.
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-]

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


Overview

PETN (pentaerythritol tetranitrate, 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. 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.

PETN is also used as a vasodilator, similar to Glyceryl trinitrate (pharmacology). The medicine for heart diseases, "Lentonitrat", is pure PETN.[1]

Properties

The velocity of detonation of PETN at a density of 1.7 g/cm³ is 8,400 meters per second. The heat of explosion is 5,862 kilojoules per kilogram[2], or 1.5 times that of TNT.

PETN's formula is C(CH2ONO2)4. Its theoretical maximum crystal density is 1.773 g/cm³. It melts at 141 °C.

As a pollutant in the environment

PETN does not occur naturally, so the production of this kind of compound without detonation may lead to contamination of the environment. PETN is subject to biodegradation in untreated or unpreserved urine and feces. 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.

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

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. [3] PETN is also one of the ingredients in Semtex plastic explosive.

See also

References

  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. PMID 4957459.
  2. Erich Ammedick: Militärchemie. eine Einführung. 4. Auflage. In: Bausteine der Chemie. VEB Deutscher Verlag für Grundstoffindustrie, Leipzig 1980, ISBN 978-3342000372 (German)
  3. Stettbacher, Alfred (1933). Die Schiess- und Sprengstoffe. Barth, 459. 

Additional Resources

External links

cs:Pentrit

de:Nitropentaeo:PETNit:Tetranitrato di pentaeritrite he:PETN lv:Tetranitropentaeritrīts lt:PETN hu:Pentaeritrit-tetranitrátsk:Pentrit sl:Pentrit fi:PETN sv:Pentyl (sprängämne)


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