Diethylene glycol dinitrate (DEGDN) is an explosive
nitrated alcohol ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...
with the formula C
4H
8N
2O
7. 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 ...
s, 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
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 alcohols an ...
of
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 of ethylene glycol. It is miscible in water, alcohol, ...
with
nitric acid
Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitri ...
in presence of a
dehydrating agent like concentrated
sulfuric acid.
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, which is used in smokeless powder for
artillery
Artillery is a class of heavy military ranged weapons that launch munitions far beyond the range and power of infantry firearms. Early artillery development focused on the ability to breach defensive walls and fortifications during siege ...
and
rocket propellant. During
World War II
World War II or the Second World War, often abbreviated as WWII or WW2, was a world war that lasted from 1939 to 1945. It involved the vast majority of the world's countries—including all of the great powers—forming two opposing ...
, the
Kriegsmarine frequently used this mixture in their artillery. It has also found use as desensitizing
plasticizer
A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture.
Plasticiz ...
because it contributes to the power of the mixture while stabilizing the explosives.
Toxicity
If ingested, like
nitroglycerine
Nitroglycerin (NG), (alternative spelling of nitroglycerine) also known as trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless, oily, explosive liquid most commonly produced by nitrating ...
, it rapidly causes
vasodilation
Vasodilation 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. The process is the opposite of vasoconstrictio ...
through the release of
nitric oxide, a physiological signaling molecule that relaxes smooth muscle. Consequently, diethylene glycol dinitrate has occasionally been used medically to relieve
angina, which is substernal
chest pain associated with impaired
cardiac
The heart is a muscular organ in most animals. This organ pumps blood through the blood vessels of the circulatory system. The pumped blood carries oxygen and nutrients to the body, while carrying metabolic waste such as carbon dioxide to t ...
circulation. The rationale is that the concurrent headache it induces is somewhat less severe than other
nitro compound
In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitr ...
s.
Uses
At present, interest in the chemical seems to be mostly historical: more potent
perchlorate
A perchlorate is a chemical compound containing the perchlorate ion, . The majority of perchlorates are commercially produced salts. They are mainly used as oxidizers for pyrotechnic devices and to control static electricity in food packaging. Per ...
–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
Triethylene glycol dinitrate (TEGDN) is a nitrated alcohol ester of triethylene glycol. It is used as an energetic plasticizer in explosives and propellants. Its chemical formula is O2N-O-CH2CH2-O-CH2CH2-O-CH2CH2-O-NO2. It is a pale yellow oily ...
, diethylene glycol dinitrate, and
trimethylolethane trinitrate
Trimethylolethane trinitrate (TMETN), also known as metriol trinitrate (METN, MTN, METRTN) or nitropentaglycerin, is a nitrate ester. It is a high explosive similar to nitroglycerin. It is a transparent oily liquid, colorless to light brown. It i ...
are being considered as replacements for nitroglycerin in propellants.
See also
*
TNT equivalent
TNT equivalent is a convention for expressing energy, typically used to describe the energy released in an explosion. The is a unit of energy defined by that convention to be , which is the approximate energy released in the detonation of a ...
*
RE factor
TNT equivalent is a convention for expressing energy, typically used to describe the energy released in an explosion. The is a unit of energy defined by that convention to be , which is the approximate energy released in the detonation of a m ...
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