Erythritol tetranitrate
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Erythritol tetranitrate (ETN) is an explosive compound chemically similar to
PETN Pentaerythritol tetranitrate (PETN), also known as PENT, PENTA, (ПЕНТА, primarily in Russian) TEN, corpent, or penthrite (or, rarely and primarily in German, as nitropenta), is an explosive material. It is the nitrate ester of pentaerythri ...
, though it is thought to be slightly more sensitive to friction and impact. Like many
nitrate ester In organic chemistry, a nitrate ester is an organic functional group with the formula , where R stands for any organic residue. They are the esters of nitric acid and alcohols. A well-known example is nitroglycerin, which is not a ''nitro'' co ...
s, ETN acts as a vasodilator, and was the active ingredient in the original " sustained release" tablets, made under a process patent in the early 1950s, 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 detonation Explosive velocity, also known as detonation velocity or velocity of detonation (VoD), is the velocity at which the shock wave front travels through a detonated explosive. Explosive velocities are always faster than the local speed of sound in the ...
of 8206 m/s at a density of 1.7219 (±0.0025) g/cm3. It is white in color and odorless. ETN is commonly cast into mixtures with other
high explosives 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 expl ...
. It is somewhat sensitive to shock and friction, so care needs to be taken while handling. ETN dissolves readily in
acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...
and other
ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
solvents. The impact and friction sensitivity is slightly higher than the sensitivity of
pentaerythritol tetranitrate Pentaerythritol tetranitrate (PETN), also known as PENT, PENTA, (ПЕНТА, primarily in Russian) TEN, corpent, or penthrite (or, rarely and primarily in German, as nitropenta), is an explosive material. It is the nitrate ester of pentaerythr ...
(PETN). The sensitivity of melt cast and pressed ETN is comparable. Lower nitrates of erythritol, such as erythritol trinitrate, are soluble in water, so they do not contaminate most ETN samples. 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. ETN has a melting point of 61 °C, compared to PETN which has a melting point of 141.3 °C. Recent studies of ETN decomposition suggested a unimolecular rate-limiting step in which the O−NO2 bond is cleaved and begins the decomposition sequence. ETN can and should be recrystallized, as to remove the trapped acids from synthesis. Warm
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
or
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...
is a viable solvent (close to 10 g of ETN/100 ml EtOH). ETN will precipitate as big platelets with bulk density of about 0.3 g/cm3 (fluffy material) when the ETN/ethanol solution is quickly poured into several liters of cold water. Smaller, fine crystals are produced by slow addition of water in said ETN/ethanol solution with intense mixing. Very fine crystals can be prepared by shock cooling of warm ETN/ethanol solution in a below −20 °C cooling bath. ETN can be easily hand pressed to about 1.2 g/cm3 (with a slight risk of accidental detonation). Even small samples of ETN on the order of 20 mg can cause relatively powerful explosions verging on detonation when heated without confinement, e.g. when placed on a layer of aluminium foil and heated with flame from below. ETN can be melt-cast in warm (about 65 °C) water. Slight decomposition is possible (often displayed by change in color from white to very light yellow). Nonetheless, no reports of runaway reactions leading to explosion have been confirmed (when melt-casting using only a bucket of warm water and recrystallized ETN). Melt-cast ETN, if cooled down slowly over a period of 10–30 minutes, has density of 1.70 g/cm3, detonation velocity of 8040 m/s, and Pcj detonation pressure of about 300 kbar. Its
brisance In explosives engineering, brisance (; , ) is the shattering capability of a high explosive, determined mainly by its detonation pressure. Practical uses Brisance is of practical importance for determining the effectiveness of an explosion in ...
is far higher than that of Semtex (about 220 kbar, depending on brand) Mixtures of melt-cast ETN with PETN (about 50:50% by weight) are about the most brisant explosives that can be produced by moderately equipped amateurs. These mixtures have Pcj slightly above 300 kbar and detonation velocity above 8 km/s. This is close to the maximum of fielded military explosives like LX-10 or EDC-29 (about 370 kbar and close to 9 km/s). ETN is often plasticized using PIB/synthethic oil binders (very comparable to the binder system in C4) or using liquid nitric esters. The PIB-based plastic explosives are nontoxic and completely comparable to C4 or
Semtex Semtex is a general-purpose plastic explosive containing RDX and PETN. It is used in commercial blasting, demolition, and in certain military applications. Semtex was developed and manufactured in Czechoslovakia, originally under the name B 1 ...
with Pcj of 200–250 kbar, depending on density (influenced by crystal size, binder amount, and amount of final rolling). EGDN/ETN/ NC systems are toxic to touch, quite sensitive to friction and impact, but generally slightly more powerful than C4 (Pcj of about 250 kbar and Edet of 5.3 MJ/kg) and more powerful than
Semtex Semtex is a general-purpose plastic explosive containing RDX and PETN. It is used in commercial blasting, demolition, and in certain military applications. Semtex was developed and manufactured in Czechoslovakia, originally under the name B 1 ...
(Pcj of about 220 kbar and Edet below 5 MJ/kg) with Pcj of about 250–270 kbar and Edet of about 6 MJ/kg. Note that different explosive software and different experimental tests will yield absolute detonation pressures that can vary by 5% or more with the relative proportions being maintained. Melt-cast ETN gives invalid results in the Hess test, i.e. the deformation is greater than 26 mm, with the lead cylinder being completely destroyed. Semtex 1A gives only 21 mm in the same test, i.e. melt-cast ETN is at least 20% more brisant than Semtex 1A. Melt-cast ETN or high density/low inert content ETN plastic explosives are one of the materials on "watch-lists" for terrorism.


Oxygen balance

One quality this explosive has, that PETN does not, is a positive
oxygen balance Oxygen balance (OB, OB%, or Ω) 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 fully oxidize the other atoms in the explosive. For example, fully ...
, which means that ETN possesses more than enough oxygen in its structure to fully oxidize all of its
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
and
hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
upon
detonation Detonation () is a type of combustion involving a supersonic exothermic front accelerating through a medium that eventually drives a shock front propagating directly in front of it. Detonations propagate supersonically through shock waves with ...
. This can be seen in the schematic chemical equation below. :2 C4H6N4O12 → 8 CO2 + 6 H2O + 4 N2 + 1 O2 Whereas PETN decomposes to: :2 C5H8N4O12 → 6 CO2 + 8 H2O + 4 N2 + 4 CO The
carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...
(CO) still requires oxygen to complete oxidation to
carbon dioxide Carbon dioxide (chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is transpar ...
(CO2). A detailed study of the decomposition chemistry of ETN has been recently elucidated. Thus, for every two moles of ETN that decompose, one free mole of O2 is released. This oxygen could be used to oxidize an added metal dust, or an oxygen-deficient explosive, such as
TNT Trinitrotoluene (), more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagen ...
or PETN. A chemical equation of how the oxygen from ETN with oxidizes PETN is shown below. The extra oxygen from the ETN oxidizes the carbon monoxide (CO) to carbon dioxide (CO2). :2 C4H6N4O12 + 1 C5H8N4O12 → 13 CO2 + 10 H2O + 6 N2


Manufacture

Like other nitrated
polyols In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups (). The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, thr ...
, ETN is made by nitrating
erythritol Erythritol is an organic compound, a four-carbon sugar alcohol (or polyol) with no optical activity, used as a food additive and sugar substitute. It is naturally occurring. It can be made from corn using enzymes and fermentation. Its formula i ...
either through the mixing of concentrated
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
and a
nitrate Nitrate is a polyatomic ion A polyatomic ion, also known as a molecular ion, is a covalent bonded set of two or more atoms, or of a metal complex, that can be considered to behave as a single unit and that has a net charge that is not zer ...
salt, or by using a mixture of sulfuric and nitric acid.


See also

*
Mannitol hexanitrate Mannitol hexanitrate is a powerful explosive. Physically, it is a powdery solid at normal temperature ranges, with density of 1.73 g/cm3. The chemical name is hexanitromannitol and it is also known as nitromannite, MHN, and nitromannitol, a ...
*
Xylitol pentanitrate Xylitol pentanitrate (XPN) is a nitrated ester primary explosive first synthesized in 1891 by Gabriel Bertrand. Law enforcement has taken an interest in XPN along with erythritol tetranitrate (ETN) and pentaerythritol tetranitrate (PETN) due to t ...


References

{{DEFAULTSORT:Erythritol Tetranitrate Explosive chemicals Nitrate esters Sugar alcohol explosives