Nitropenta

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Structural formula
Structural formula of nitropenta
General
Surname Nitropenta
other names
  • Pentaerythrityl tetranitrate ( INN )
  • 1,3-bis (nitryloxy) -2,2-bis (nitryloxy-methyl) propane ( IUPAC )
  • Pentaerythritol granitrate
  • Pentaerythritol tetranitrate
  • Bis [(nitrooxy) methyl] propanediol dinitrate
  • PETN
  • Pentastite
Molecular formula C 5 H 8 N 4 O 12
Brief description

explosive solid

External identifiers / databases
CAS number 78-11-5
EC number 201-084-3
ECHA InfoCard 100,000,987
PubChem 6518
ChemSpider 6271
DrugBank DB06154
Wikidata Q189334
Drug information
ATC code

C01 DA05

Drug class

Vasodilator

properties
Molar mass 316.15 g mol −1
Physical state

firmly

density

1.778 g cm −3 (22 ° C, PETN-I)

Melting point

141-142.9 ° C

boiling point

Decomposition 163-170 ° C

Vapor pressure

1.36 10 −7 mmHg (25 ° C)

solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
01 - Explosive

danger

H and P phrases H: 200
P: 201-202-281-372-373-380-401-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nitropenta ( PETN , pentrit , pentaerythrityl tetranitrate ) is an explosive and medicinal substance . Analogous to nitroglycerin , the substance is not a nitro compound in the chemical sense , but a nitrate , i.e. an ester of nitric acid .

history

Bernhard Tollens and P. Wigand succeeded in synthesizing pentaerythritol in 1891 by the alkaline condensation of acetaldehyde and formaldehyde . Nitropenta was produced by subsequent esterification with nitric acid ( nitration ) in 1894 by Rheinisch-Westfälische Sprengstoff AG ( Cologne ) and was first recommended by Thieme as an additive to low-smoke powders. Claessen applied for a patent for the use of nitropenta in ignition amplifiers as early as 1912, but it was not until after the First World War that it was increasingly used in the civil and military sectors.

presentation

The technical representation is carried out by adding pentaerythritol in concentrated nitric acid .

Nitropenta synthesis.svg

properties

Physico-chemical properties

Nitropenta occurs in two polymorphic forms as colorless crystals, the common tetragonal PETN-I (α-PETN) and the orthorhombic PETN-II (β-PETN), into which PETN-I changes at 130 ° C. The density is 1.778 (22 ° C, PETN-I) or 1.716 (136 ° C, PETN-II). Nitropenta is insoluble in water , slightly soluble in ethanol , diethyl ether and benzene , but readily soluble in acetone and methyl acetate .

Explosion parameters

Nitropenta is one of the powerful, highly explosive and also relatively insensitive and chemically very stable explosives. Important explosion indicators are:

use

Explosive

From around 1926 onwards, technical application through large-scale production of the starting material pentaerythritol was possible. It began to be used as a component of detonators , cords and as highly explosive projectile fillings in combination with TNT as pentolite in smaller calibers. Today nitropenta detonating cords are used in the commercial sector. In connection with plasticizers, nitropenta is used as a plastic explosive , for example under the name Semtex , or processed with phlegmatizers such as wax to make charges for hand grenades . For example, it appears in the hand grenade of the German Bundeswehr , the DM51 .

From 2009/2010, terrorists (presumably close to Al-Qaeda) are using Nitropenta to build explosives.

Medicinal active ingredient

In medicine, nitropenta is used under the name "Pentalong" as a vasodilator drug for angina pectoris , analogous to glycerol trinitrate . Depending on the production, a mixture of pentaerythrimono-, di-, tri- and tetranitrate is obtained during manufacture. Studies in rats had indicated that PETN did not develop tolerances in the body. However, there are no randomized, controlled studies that show that pentaerythrityl tetranitrate has an advantage in terms of tolerance development in humans.

As of 2016: “As a result, the BfArM has now granted the long-term nitrate subsequent approval - with effect from July 29, 2016. Thus, Pentalong ® 50 mg is no longer fictitious, but regular approved. As a result, the tablets are now subject to statutory health insurance once again. ”(Quote from the German Pharmacist newspaper online).

According to the Deutsches Ärzteblatt, the Clinic for Gynecology and Obstetrics at the Jena University Hospital will be testing the active ingredient PETN in a clinical, randomized and placebo- controlled study in 14 study centers from 2016 to determine whether it is suitable for preventing an insufficient supply of babies in high-risk pregnancies ; In laboratory experiments, the scientists have already been able to demonstrate that it is safe to take the active ingredient during pregnancy: the drug cannot pass from the placenta to the child.

Legal Notice

Handling, traffic and import of PETN are subject to the Explosives Act in Germany . The substance is divided into substance group A in Appendix II.

Related explosives

Explosives with a similar chemical structure and consisting of a polyhydric alcohol esterified with nitric acid are, for example:

Trade names

Monopreparations : Pentalong (D)

Individual evidence

  1. ↑ a b c Entry on pentaerythritol granitrate in the GESTIS substance database of the IFA , accessed on February 22, 2017(JavaScript required) .
  2. ↑ a b c d e f Entry on pentaerythritol tetranitrate. In: Römpp Online . Georg Thieme Verlag, accessed on May 25, 2014.
  3. ↑ Entry on Pentaerythritol tetranitrate in the Hazardous Substances Data Bank , accessed on June 15, 2017.
  4. ↑ a b c d e f g h i j k l m n o J. Köhler, R. Meyer, A. Homburg: Explosivstoffe , tenth, completely revised edition, Wiley-VCH, Weinheim 2008, ISBN 978-3-527- 32009-7
  5. ↑ Entry on Pentaerithrityl tetranitrate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  6. ↑ B. Tollens, P. Wigand (1891): About penta-erythritol, a tetravalent alcohol synthetically produced from formaldehyde and acetaldehyde . In: Justus Liebigs Annalen der Chemie, 265 (3), pp. 316-340; doi: 10.1002 / jlac.18912650303 .
  7. ↑ Jonas A. Zukas, William P. Walters: Explosive effects and applications. Springer New York, 1998 ( limited preview in Google book search), p. 41.
  8. ^ G. Bugge, Guns and explosives and the men who created them, Franckh'sche Verlagshandlung, Stuttgart, 1942, p. 57.
  9. ^ C. Claessen, Process for the production of detonators for detonators, primers and projectile detonations, DE265025A, December 8, 1912; online .
  10. ^ A. Stettbacher, Spreng- und Schiesstoffe, Rascher Verlag, Zurich, 1948, p. 67.
  11. ↑ Lexicon of German Explosive Mixtures. Archived from the original on March 17, 2015 ; Retrieved December 30, 2009 .
  12. ↑ Spiegel Online: Investigators find 24 suspicious air freight packages , October 30, 2010.
  13. ↑ Doctors newspaper online: Why the nitrate does not tolerate PETN April 2007, PDF accessed on April 24, 2011.
  14. ↑ Kirsten Sucker-Sket (ks): Pentalong is now regularly approved. August 9, 2016. Retrieved August 23, 2016 .
  15. ↑ Jena University Clinic tests PETN to prevent insufficient supply of babies in high-risk pregnancies - DFG funds clinical study (head of study: Tanja Groten). September 8, 2016, accessed September 12, 2016 .
  16. ^ Sprengstoffgesetz - SprengG , accessed on November 6, 2018.
  17. ↑ Red List online, as of April 2012.

literature

  • T. Urbanski: Chemistry and technology of explosives . 1961
  • R. Haas, J. Thieme: Synonym index of explosives
  • J. Gartz: cultural history of explosives , ES Mittler & Sohn. Hamburg 2006.
  • G. Hommel: Handbook of dangerous goods

Web links

Wiktionary: Nitropenta  - explanations of meanings, word origins, synonyms, translations