Erythritol tetranitrate
Encyclopedia
Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN
. It is however thought to be 1/3 more sensitive to friction and impact. ETN is not well known, but in recent years has been used by amateur experimenters to replace PETN in improvised detonation cord or in boosters to initiate larger, less sensitive explosive charges. Due to the availability of erythritol
as a natural sweetener and its relative ease of production in relation to PETN
, ETN is a favoured home made explosive compound to the amateur experimenter.
Like many nitric esters, ETN acts as a vasodilator, and was the active ingredient in the original "sustained release
" tablets, made under a process patent in the early 50's, called "nitroglyn". Ingesting ETN or prolonged skin contact can lead to absorption and what is known as a "nitro headache".
of 8000-8100 m/s at a density of 1.6 g/cm3. It is white in color and odorless. ETN is commonly cast into mixtures with other high explosives. It is somewhat sensitive to shock and friction, so care should be taken while handling. ETN dissolves readily in acetone
and other ketone
solvents though for the purpose of recrystallization, slow cooling of a saturated solution in ethanol
from 55 °C gives much better results with purer and better formed crystals.
Much like PETN, ETN is known for having a very long shelf life. Studies that directly observed the crystalline structure saw no signs of decomposition after four years of storage at room temperature.
. Having a positive oxygen balance means that ETN possesses more than enough oxygen in its structure to fully oxidize all of its carbon
and hydrogen
upon detonation
. This can be seen in the equation below.
Whereas PETN decomposes to:
The carbon monoxide
(CO) still requires oxygen to complete oxidation to carbon dioxide
(CO2).
Thus for every mole of ETN that decomposes, 1/2 free mole of O2 is released. This could be used to oxidize an added metal dust or an oxygen deficient explosive such as TNT or PETN.
and a nitrate
salt. Ammonium nitrate is commonly used for this type of reaction. The erythritol is added to the mixture to begin its nitration. Much better yields can be obtained by using concentrated nitric acid
in place of the nitrate salt, in which case the sulfuric acid
is used simply to absorb water and act as a catalyst from the resulting esterification, driving the reaction.
PETN
Pentaerythritol tetranitrate , also known as PENT, PENTA, TEN, corpent, penthrite , is the nitrate ester of pentaerythritol. Penta refers to the five carbon atoms of the neopentane skeleton.PETN is most well known as an explosive...
. It is however thought to be 1/3 more sensitive to friction and impact. ETN is not well known, but in recent years has been used by amateur experimenters to replace PETN in improvised detonation cord or in boosters to initiate larger, less sensitive explosive charges. Due to the availability of erythritol
Erythritol
Erythritol is a sugar alcohol that has been approved for use as a food additive in the United States and throughout much of the world. It was discovered in 1848 by British chemist John Stenhouse. It occurs naturally in some fruits and fermented foods...
as a natural sweetener and its relative ease of production in relation to PETN
PETN
Pentaerythritol tetranitrate , also known as PENT, PENTA, TEN, corpent, penthrite , is the nitrate ester of pentaerythritol. Penta refers to the five carbon atoms of the neopentane skeleton.PETN is most well known as an explosive...
, ETN is a favoured home made explosive compound to the amateur experimenter.
Like many nitric esters, ETN acts as a vasodilator, and was the active ingredient in the original "sustained release
Sustained release
Time release technology, also known as sustained-release , sustained-action , extended-release , time-release or timed-release, controlled-release , modified release , or continuous-release , is a mechanism used in pill tablets or capsules to...
" tablets, made under a process patent in the early 50's, called "nitroglyn". Ingesting ETN or prolonged skin contact can lead to absorption and what is known as a "nitro headache".
Properties
ETN has a relatively high velocity of detonationExplosive velocity
Explosive velocity, also known as detonation velocity or velocity of detonation , is the velocity at which the shock wave front travels through a detonated explosive. The data listed for a specific substance is usually a rough prediction based upon gas behavior theory , as in practice it is...
of 8000-8100 m/s at a density of 1.6 g/cm3. It is white in color and odorless. ETN is commonly cast into mixtures with other high explosives. It is somewhat sensitive to shock and friction, so care should be taken while handling. ETN dissolves readily in acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
and other ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
solvents though for the purpose of recrystallization, slow cooling of a saturated solution in ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
from 55 °C gives much better results with purer and better formed crystals.
Much like PETN, ETN is known for having a very long shelf life. Studies that directly observed the crystalline structure saw no signs of decomposition after four years of storage at room temperature.
Oxygen balance
One quality this explosive has, that PETN does not, is a positive oxygen balanceOxygen balance
Oxygen balance is an expression that is used to indicate the degree to which an explosive can be oxidized. If an explosive molecule contains just enough oxygen to form carbon dioxide from carbon, water from hydrogen molecules, all of its sulfur dioxide from sulfur, and all metal oxides from metals...
. Having a positive oxygen balance means that ETN possesses more than enough oxygen in its structure to fully oxidize all of its carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
and hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
upon detonation
Detonation
Detonation involves a supersonic exothermic front accelerating through a medium that eventually drives a shock front propagating directly in front of it. Detonations are observed in both conventional solid and liquid explosives, as well as in reactive gases...
. This can be seen in the equation below.
- C4H6N4O12 → 4 CO2 + 3 H2O + 2 N2 + ½ O2
Whereas PETN decomposes to:
- C5H8N4O12 → 3 CO2 + 2 CO + 4 H2O + 2 N2
The carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...
(CO) still requires oxygen to complete oxidation to carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...
(CO2).
Thus for every mole of ETN that decomposes, 1/2 free mole of O2 is released. This could be used to oxidize an added metal dust or an oxygen deficient explosive such as TNT or PETN.
Manufacture
Like other nitrated polyols, ETN is made by nitrating erythritol through the mixing of concentrated sulfuric acidSulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
and a nitrate
Nitrate
The nitrate ion is a polyatomic ion with the molecular formula NO and a molecular mass of 62.0049 g/mol. It is the conjugate base of nitric acid, consisting of one central nitrogen atom surrounded by three identically-bonded oxygen atoms in a trigonal planar arrangement. The nitrate ion carries a...
salt. Ammonium nitrate is commonly used for this type of reaction. The erythritol is added to the mixture to begin its nitration. Much better yields can be obtained by using concentrated nitric acid
Nitric acid
Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosive and toxic strong acid.Colorless when pure, older samples tend to acquire a yellow cast due to the accumulation of oxides of nitrogen. If the solution contains more than 86% nitric acid, it is referred to as fuming...
in place of the nitrate salt, in which case the sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
is used simply to absorb water and act as a catalyst from the resulting esterification, driving the reaction.
See also
- Mannitol hexanitrate
- Xylitol pentanitrateXylitol pentanitrateXylitol pentanitrate is a rarely used liquid explosive compound with extremely high viscosity formed by completely nitrating xylitol, a sugar alcohol compound with five carbon atoms. In pure form it is a white crystalline explosive, much like other fully nitrated polyols...
- Nitroglycerine, most properly Glycerol trinitrate
- Ethylene glycol dinitrate
- Methyl nitrateMethyl nitrateMethyl nitrate is the methyl ester of nitric acid and has the chemical formula CH3NO3.Methyl nitrate is toxic and a sensitive explosive. It causes headaches when fumes are inhaled...
- sustained releaseSustained releaseTime release technology, also known as sustained-release , sustained-action , extended-release , time-release or timed-release, controlled-release , modified release , or continuous-release , is a mechanism used in pill tablets or capsules to...