Ethylene glycol dinitrate
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| IUPAC name
| Other names
Ethylene glycol dinitrate
|Molar mass||152.1 g/mol|
|Appearance||Colorless to yellow liquid|
|Density||1.4918 g/cm3 (20 °C)|
|Melting point||−22.3 °C (−8.1 °F; 250.8 K)|
|Boiling point||197.5 °C (387.5 °F; 470.6 K)|
|0.5 g/100 ml|
|Solubility||Miscibile with glacial acetic acid, acetone, benzene, CCl4, chloroform, diethyl ether, methanol, toluene|
|Vapor pressure||0.05 mmHg (20 °C)|
|Safety data sheet||cpcb|
|Flash point||215 °C (419 °F, 488 K)|
| Methyl nitrate|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Ethylene glycol dinitrate, IUPAC name 1,2-dinitroxyethane, also known as nitroglycol or EGDN, is a pale yellow, syrupy, explosive liquid. In the series of alkyl nitrates it is among those which have a 1:1 ratio of nitroxy groups per carbon atom, and also exhibits a perfect oxygen balance.
Thanks to its perfect oxygen balance, EGDN is one of the strongest explosives known, with a lead block test value of 650 cm3 (10% higher than NG). It is more sensitive to initiation but can also detonate incompletely with low velocity. The reported detonation velocity is around 7800 m/s.
Its properties are very similar to nitroglycerin. It is however less viscous, less dense and more volatile. The freezing point is -22 °C, and it has therefore been used for dynamites in cold climates.
EGDN can be prepared by nitrating ethylene glycol under careful monitoring.
Another route is the reaction between ethylene oxide and dinitrogen pentoxide, in the presence of ozone. Reaction takes place in dichloromethane for 5 min, at temperatures between 10-15 °C. Yield is 96%.
Like nitroglycerin, EGDN is highly explosive, although somewhat less sensitive to impact. One disadvantage EGDN has against NG is that EGDN is more volatile. This makes a person working with it more susceptible to its vasodilation effects, which is where the nitro group in the nitrated alcohol causes the body to widen blood vessels, resulting in phenomenal headaches.
Never store EGDN!
EGDN can be neutralized with a cold sodium hydroxide solution.
- Golding, P.; Millar, R. W.; Paul, N. C.; Richards, D. H.; Tetrahedron Letters; vol. 29; nb. 22; (1988); p. 2731 - 2734
- Golding, Peter; Millar, Ross W.; Paul, Norman C.; Richards, David H.; Tetrahedron; vol. 49; nb. 32; (1993); p. 7037-7050
Chemistry and Technology of Explosives - Volume II, first edition, 1965.