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-]

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

Overview

Pentaerythritol tetranitrate (PETN), also known as PENT, PENTA, TEN, corpent, penthrite (or—rarely and primarily in German—as nitropenta), is the nitrate ester of pentaerythritol, and is structurally very similar to nitroglycerin. Penta refers to the five carbon atoms of the neopentane skeleton.

PETN is best known as an explosive. It is one of the most powerful high explosives known, with a relative effectiveness factor of 1.66.

PETN mixed with a plasticizer forms a plastic explosive. As a mixture with RDX and other minor additives, it forms another plastic explosive called Semtex as well. The compound was discovered in the bombs used by the 2001 Shoe Bomber, in the 2009 Christmas Day bomb plot, and in the 2010 cargo plane bomb plot. On 7 September 2011, a bomb suspected to have used PETN exploded near the High Court of Delhi in India claiming 13 lives and injuring more than 70.

It is also used as a vasodilator drug to treat certain heart conditions, such as for management of angina.[1][2]

History

Penthrite was first synthesized in 1891 by Bernhard Tollens and P. Wigand by nitration of pentaerythritol.[3] The production of PETN started in 1912, when it was patented by the German government. PETN was used by the German Army in World War I.[4]

Properties

PETN is practically insoluble in water (0.01 g/100 ml at 50 °C), weakly soluble in common nonpolar solvents such as aliphatic hydrocarbons (like gasoline) or tetrachloromethane, but soluble in some other organic solvents, particularly in acetone (about 15 g/100 g of the solution at 20 °C, 55 g/100 g at 60 °C) and dimethylformamide (40 g/100 g of the solution at 40 °C, 70 g/100 g at 70 °C). PETN forms eutectic mixtures with some liquid or molten aromatic nitro compounds, e.g. trinitrotoluene (TNT) or tetryl. Due to its highly symmetrical structure, PETN is resistant to attack by many chemical reagents; it does not hydrolyze in water at room temperature or in weaker alkaline aqueous solutions. Water at 100 °C or above causes hydrolysis to dinitrate; presence of 0.1% nitric acid accelerates the reaction. Addition of TNT and other aromatic nitro derivatives lowers thermal stability of PETN.

The chemical stability of PETN is of interest, because of the use of PETN in aging stockpiles of weapons. A review has been published. Neutron radiation degrades PETN, producing carbon dioxide and some pentaerythritol dinitrate and trinitrate. Gamma radiation increases the thermal decomposition sensitivity of PETN, lowers melting point by few degrees Celsius, and causes swelling of the samples. Like other nitrate esters, the primary degradation mechanism is the loss of nitrogen dioxide; this reaction is autocatalytic. Studies were performed on thermal decomposition of PETN.

In the environment, PETN undergoes biodegradation. Some bacteria denitrate PETN to trinitrate and then dinitrate, which is then further degraded. PETN has low volatility and low solubility in water, and therefore has low bioavailability for most organisms. Its toxicity is relatively low, and its transdermal absorption also seems to be low. It poses a threat for aquatic organisms. It can be degraded to pentaerythritol by iron metal.[5]

Production

Production is by the reaction of pentaerythritol with concentrated nitric acid to form a precipitate which can be recrystallized from acetone to give processable crystals.

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

Variations of a method first published in a US Patent 2,370,437 by Acken and Vyverberg (1945 to Du Pont) forms the basis of all current commercial production.

PETN is manufactured by numerous manufacturers as a powder about the consistency of fine popcorn salt, or together with nitrocellulose and plasticizer as thin plasticized sheets (e.g. Primasheet 1000 or Detasheet). PETN residues are easily detectable in hair of people handling it.[6] The highest residue retention is on black hair; some residues remain present even after washing.[7][8]

Medical Use

Like nitroglycerin (glyceryl trinitrate) and other nitrates, PETN is also used medically as a vasodilator in the treatment of heart conditions.[1][2] These drugs work by releasing the signaling gas nitric oxide in the body. The heart medicine Lentonitrat is nearly pure PETN.[9]

Monitoring of oral usage of the drug by patients has been performed by determination of plasma levels of several of its hydrolysis products, pentaerythritol dinitrate, pentaerythritol mononitrate and pentaerythritol, in plasma using gas chromatography-mass spectrometry.[10]

See Also

References

  1. 1.0 1.1 (1959) "New Drugs". Can Med Assoc J 80: 997–998. PMID 20325960.
  2. 2.0 2.1 Manuchair S. Ebadi (1998). CRC desk reference of clinical pharmacology (Google Books excerpt), 383. ISBN 978-0-8493-9683-0. 
  3. (1891) "Über den Penta-Erythrit, einen aus Formaldehyd und Acetaldehyd synthetisch hergestellten vierwerthigen Alkohol (On penta-erythritol, a tetravalent alcohol synthetically produced from formaldehyde and acetaldehyde)". Justus Liebig's Annalen der Chemie 265: 316–340. doi:10.1002/jlac.18912650303.
  4. Stettbacher, Alfred (1933). Die Schiess- und Sprengstoffe, 2. völlig umgearb. Aufl., Barth, 459. 
  5. Li Zhuang, Lai Gui and Robert W. Gillham (2008). "Degradation of Pentaerythritol Tetranitrate (PETN) by Granular Iron". Environ. Sci. Technol. 42. doi:10.1021/es7029703. PMID 18605582.
  6. Winslow, Ron. (2009-12-29) A Primer in PETN – WSJ.com. Online.wsj.com. Retrieved on 2010-02-08.
  7. (2005) "Accumulation of Explosives in Hair". Journal of Forensic Sciences 50. doi:10.1520/JFS2004545.
  8. Template error: argument title is required.  Template:Dead link
  9. 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.
  10. R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1201–1203.

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