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Diethylene glycol dinitrate

Diethyl glycol dinitrate Oxydiethylene dinitrate DEGDN 1.3846 g/mL (20 °C)

Diethylene glycol dinitrate (DEGDN) is an explosive nitrated alcohol ester with the formula C4H8N2O7. It is commonly used as a plasticizer in propellant or explosive formulations. While chemically similar to numerous other high explosives, pure diethylene glycol dinitrate is difficult to ignite. Ignition typically requires localized heating to the decomposition point unless the DEGDN is first atomized. It is sensitive to detonation by impact but not due to friction.

Preparation and uses

Diethylene glycol dinitrate can be made by nitration of diethylene glycol with nitric acid in presence of a dehydrating agent like concentrated sulfuric acid.

Toxicity

If ingested, like nitroglycerine, it rapidly causes vasodilation through the release of nitric oxide, a physiological signaling molecule that relaxes vascular smooth muscle which leads to a rapid loss in blood pressure. Other acute effects include convulsions and loss of consciousness. Its median lethal dose (LD50) is 650 mg/kg in guinea pigs.

Uses

DEGDN can be mixed with nitrocellulose or nitroglycol to form a colloid, which is used in smokeless powder for artillery and rocket propellant. During World War II, the Kriegsmarine frequently used this mixture in their artillery.

Triethylene glycol dinitrate, diethylene glycol dinitrate, and trimethylolethane trinitrate can be used as less-sensitive as replacements for nitroglycerin in propellants.

References

  • W. H. Rinkenbach, Industrial Engineering Chemistry v19 p925 (1927) Note: the present author has transliterated some terminology and notation in line with modern practice.
  • Military applications referenced in Encyclopedia of Weapons of World War 2; Gen. Ed. Chris Bishop, c.2003 Friedman/Fairfax NYNY,

References

  1. Kubota, Naminosuke. (2015). "Propellants and explosives: thermochemical aspects of combustion". Wiley-VCH.
  2. Hoque, Ehtasimul. (2020-03-09). "Study on Friction Sensitivity of Passive and Active Binder based Composite Solid Propellants and Correlation with Burning Rate". Defence Science Journal.
  3. Rinkenbach, Wm. H.. (1931). "Nitration of Diethylene Glycol". Industrial & Engineering Chemistry.
  4. "ICSC 1473 - DIETHYLENE GLYCOL DINITRATE".
  5. PubChem. "Diethylene glycol dinitrate".
  6. Tony DiGiulian. "History and Technology - Naval Propellants - A Brief Overview". NavWeaps.
  7. "Guns and Ordnance: Ammunition and Explosives - Storming Media". Stormingmedia.us.
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

nitrate-esters propellants monopropellants explosive-chemicals liquid-explosives plasticizers antianginals
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