Diethylene glycol dinitrate (original) (raw)

From Wikipedia, the free encyclopedia

Diethylene glycol dinitrate
Names
Preferred IUPAC name Oxydi(ethane-2,1-diyl) dinitrate
Other namesDiethyleneglycol dinitrateDiethyl glycol dinitrateOxydiethylene dinitrateDEGDN
Identifiers
CAS Number 693-21-0 checkY
3D model (JSmol) Interactive image
ChemSpider 55142 checkY
ECHA InfoCard 100.010.679 Edit this at Wikidata
PubChem CID 61198
UNII 77W50O99G1 checkY
UN number 0075
CompTox Dashboard (EPA) DTXSID1024047 Edit this at Wikidata
InChI InChI=1S/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2 checkYKey: LYAGTVMJGHTIDH-UHFFFAOYSA-N checkYInChI=1/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2Key: LYAGTVMJGHTIDH-UHFFFAOYAD
SMILES C(CO[N+](=O)[O-])OCCO[N+](=O)[O-]
Properties
Chemical formula C4H8N2O7
Molar mass 196.115 g·mol−1
Appearance Colorless oily liquid
Odor Odorless
Density 1.4092 g/mL (0 °C)1.3846 g/mL (20 °C)
Melting point −11.5 °C (11.3 °F; 261.6 K)
Boiling point 197 °C (387 °F; 470 K) (decomposes)
Solubility in water 4.1 g/L (24 °C)
Solubility Soluble in methanol, acetic acid
Vapor pressure 0.007 mmHg (22.4 °C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). checkY verify (what is checkY☒N ?) Infobox references

Chemical compound

Diethylene glycol dinitrate (DEGDN) is an explosive nitrated alcohol ester with the formula C4H8N2O7. While chemically similar to numerous other high explosives, pure diethylene glycol dinitrate is difficult to ignite or detonate. Ignition typically requires localized heating to the decomposition point unless the DEGDN is first atomized.

Preparation and uses

[edit]

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

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.[1] It has also found use as desensitizing plasticizer because it contributes to the power of the mixture while stabilizing the explosives.

If ingested, like nitroglycerine, it rapidly causes vasodilation through the release of nitric oxide, a physiological signaling molecule that relaxes smooth muscle.[_clarification needed_] Consequently, diethylene glycol dinitrate has occasionally been used medically to relieve angina, which is substernal chest pain associated with impaired cardiac circulation.[_citation needed_] The rationale is that the concurrent headache it induces is somewhat less severe than other nitro compounds.

At present, interest in the chemical seems to be mostly historical retaining only a few specialist uses. The medical application was never widespread, the standard nitroglycerine being faster acting and very inexpensive; oral nitrates in any case being only palliative, not an effective treatment.

Triethylene glycol dinitrate, diethylene glycol dinitrate, and trimethylolethane trinitrate are being considered as replacements for nitroglycerin in propellants.[2]

  1. ^ Tony DiGiulian. "History and Technology - Naval Propellants - A Brief Overview". NavWeaps. Retrieved 2022-08-20.
  2. ^ "Guns and Ordnance: Ammunition and Explosives - Storming Media". Stormingmedia.us. Archived from the original on 2012-09-03. Retrieved 2011-12-23.