Diethylene glycol dinitrate (DEGDN) is an explosive nitrated

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

with the formula C₄H₈N₂O₇. It is commonly used as a plasticizer in propellant or explosive formulations. While chemically similar to numerous other

high explosive An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An exp ...

s, 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.

Preparation and uses

Diethylene glycol dinitrate can be made by

nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol ...

diethylene glycol Diethylene glycol (DEG) is an organic compound with the formula (HOCH2CH2)2O. It is a colorless, practically odorless, and hygroscopic liquid with a sweetish taste. It is a four carbon Dimer (chemistry), dimer of ethylene glycol. It is miscible in ...

with

nitric acid Nitric acid is an inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into nitrogen oxide, oxides of nitrogen. Most com ...

in presence of a dehydrating agent like concentrated

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

Toxicity

If ingested, like nitroglycerine, it rapidly causes

vasodilation Vasodilation, also known as vasorelaxation, is the widening of blood vessels. It results from relaxation of smooth muscle cells within the vessel walls, in particular in the large veins, large arteries, and smaller arterioles. Blood vessel wa ...

through the release of

nitric oxide Nitric oxide (nitrogen oxide, nitrogen monooxide, or nitrogen monoxide) is a colorless gas with the formula . It is one of the principal oxides of nitrogen. Nitric oxide is a free radical: it has an unpaired electron, which is sometimes den ...

, 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. Its median lethal dose (LD50) is 650 mg/kg in guinea pigs.

Uses

DEGDN can be mixed with

nitrocellulose Nitrocellulose (also known as cellulose nitrate, flash paper, flash cotton, guncotton, pyroxylin and flash string, depending on form) is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid and ...

or nitroglycol to form a

colloid A colloid is a mixture in which one substance consisting of microscopically dispersed insoluble particles is suspended throughout another substance. Some definitions specify that the particles must be dispersed in a liquid, while others exte ...

, which is used in smokeless powder for

artillery Artillery consists of ranged weapons that launch Ammunition, munitions far beyond the range and power of infantry firearms. Early artillery development focused on the ability to breach defensive walls and fortifications during sieges, and l ...

and

rocket propellant Rocket propellant is used as reaction mass ejected from a rocket engine to produce thrust. The energy required can either come from the propellants themselves, as with a chemical rocket, or from an external source, as with ion engines. Overvi ...

. During

World War II World War II or the Second World War (1 September 1939 – 2 September 1945) was a World war, global conflict between two coalitions: the Allies of World War II, Allies and the Axis powers. World War II by country, Nearly all of the wo ...

, the

Kriegsmarine The (, ) was the navy of Nazi Germany from 1935 to 1945. It superseded the Imperial German Navy of the German Empire (1871–1918) and the inter-war (1919–1935) of the Weimar Republic. The was one of three official military branch, branche ...

frequently used this mixture in their artillery. Triethylene glycol dinitrate, diethylene glycol dinitrate, and trimethylolethane trinitrate can be used as less-sensitive as replacements for nitroglycerin in propellants.

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, {{Nitric oxide signaling Nitrate esters Propellants Monopropellants Explosive chemicals Liquid explosives Plasticizers Antianginals

Preparation and uses

Toxicity

Uses

See also

References