Diethylene glycol dinitrate
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Names | |
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Preferred IUPAC name
Oxydi(ethane-2,1-diyl) dinitrate | |
Other names
Diethyleneglycol dinitrate
Diethyl glycol dinitrate Oxydiethylene dinitrate DEGDN | |
Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.010.679 |
PubChem CID
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UNII | |
UN number | 0075
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CompTox Dashboard (EPA)
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Properties | |
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) |
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).
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Diethylene glycol dinitrate (DEGDN) is an explosive
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.
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.
Toxicity
If ingested, like
Uses
At present, interest in the chemical seems to be mostly historical: more potent
Triethylene glycol dinitrate, diethylene glycol dinitrate, and trimethylolethane trinitrate are being considered as replacements for nitroglycerin in propellants.[2]
See also
- TNT equivalent
- RE factor
References
- ^ Tony DiGiulian. "History and Technology - Naval Propellants - A Brief Overview". NavWeaps. Retrieved 2022-08-20.
- ^ "Guns and Ordnance: Ammunition and Explosives - Storming Media". Stormingmedia.us. Archived from the original on 2012-09-03. Retrieved 2011-12-23.
- 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, ISBN 1-58663-762-2