Diethylene glycol dinitrate

Diethylene glycol dinitrate

Names
Preferred IUPAC name Oxydi(ethane-2,1-diyl) dinitrate
Other names Diethyleneglycol dinitrate Diethyl glycol dinitrate Oxydiethylene dinitrate DEGDN
Identifiers
CAS Number	693-21-0 Y
3D model (JSmol)	Interactive image
ChemSpider	55142 Y
ECHA InfoCard	100.010.679
PubChem CID	61198
UNII	77W50O99G1 Y
UN number	0075
CompTox Dashboard (EPA)	DTXSID1024047
InChI InChI=1S/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2 Y Key: LYAGTVMJGHTIDH-UHFFFAOYSA-N Y InChI=1/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2 Key: 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). Y verify (what is YN ?) Infobox references

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

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 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.

Uses

At present, interest in the chemical seems to be mostly historical: more potent perchlorate–metal mixtures have long since supplanted it as a solid propellant; safer explosives have replaced nitroglycerine, true dynamites (the term is often used generically, even by experienced field technicians, to refer to almost any explosive supplied in small, discrete packages) 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]

See also

• TNT equivalent
• RE factor

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, ISBN 1-58663-762-2