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 ;
3D model (JSmol)	Interactive image;
ChemSpider	55142 ;
ECHA InfoCard	100.010.679
PubChem CID	61198;
UNII	77W50O99G1 ;
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 Key: LYAGTVMJGHTIDH-UHFFFAOYSA-N ; 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). verify (what is ?) Infobox references

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.^[1] 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.^[2]

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.^[3]

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.^[4] Its median lethal dose (LD50) is 650 mg/kg in guinea pigs.^[5]

Uses

DEGDN can be mixed with nitrocellulose or nitroglycol to form a colloid, which is used in smokeless powder for artillery and rocket propellant.^[1] During World War II, the Kriegsmarine frequently used this mixture in their artillery.^[6]

Triethylene glycol dinitrate, diethylene glycol dinitrate, and trimethylolethane trinitrate can be used as less-sensitive as replacements for nitroglycerin in propellants.^[1]^[7]

References

^ ^a ^b ^c Kubota, Naminosuke (2015). Propellants and explosives: thermochemical aspects of combustion (3 ed.). Weinheim: Wiley-VCH. ISBN 978-3-527-69348-1.
^ Hoque, Ehtasimul; Pant, Chandra Shekhar; Das, Sushanta (2020-03-09). "Study on Friction Sensitivity of Passive and Active Binder based Composite Solid Propellants and Correlation with Burning Rate". Defence Science Journal. 70 (2): 159–165. doi:10.14429/dsj.70.14802. ISSN 0976-464X.
^ Rinkenbach, Wm. H.; Aaronson, H. A. (1931). "Nitration of Diethylene Glycol". Industrial & Engineering Chemistry. 23 (2): 160–163. doi:10.1021/ie50254a014. ISSN 0019-7866.
^ "ICSC 1473 - DIETHYLENE GLYCOL DINITRATE". chemicalsafety.ilo.org. Retrieved 2025-03-08.
^ PubChem. "Diethylene glycol dinitrate". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-03-08.
^ 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

[:0-1] Kubota, Naminosuke (2015). Propellants and explosives: thermochemical aspects of combustion (3 ed.). Weinheim: Wiley-VCH. ISBN 978-3-527-69348-1.

[2] Hoque, Ehtasimul; Pant, Chandra Shekhar; Das, Sushanta (2020-03-09). "Study on Friction Sensitivity of Passive and Active Binder based Composite Solid Propellants and Correlation with Burning Rate". Defence Science Journal. 70 (2): 159–165. doi:10.14429/dsj.70.14802. ISSN 0976-464X.

[3] Rinkenbach, Wm. H.; Aaronson, H. A. (1931). "Nitration of Diethylene Glycol". Industrial & Engineering Chemistry. 23 (2): 160–163. doi:10.1021/ie50254a014. ISSN 0019-7866.

[4] "ICSC 1473 - DIETHYLENE GLYCOL DINITRATE". chemicalsafety.ilo.org. Retrieved 2025-03-08.

[5] PubChem. "Diethylene glycol dinitrate". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-03-08.

[6] Tony DiGiulian. "History and Technology - Naval Propellants - A Brief Overview". NavWeaps. Retrieved 2022-08-20.

[7] "Guns and Ordnance: Ammunition and Explosives - Storming Media". Stormingmedia.us. Archived from the original on 2012-09-03. Retrieved 2011-12-23.

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Diethylene glycol dinitrate

Preparation and uses

Toxicity

Uses

See also

References

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