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2,4,6-Trinitrophenylmethylnitramine commonly referred to as tetryl ( C7 H5 N5 O8) is an
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 expl ...
compound used to make
detonator A detonator, frequently a blasting cap, is a device used to trigger an explosive device. Detonators can be chemically, mechanically, or electrically initiated, the last two being the most common. The commercial use of explosives uses electri ...
s and
explosive booster {{unreferenced, date=August 2011 An explosive booster is a sensitive explosive charge that acts as a bridge between a (relatively weak) conventional detonator and a low-sensitivity (but typically high-energy) explosive such as TNT. By itself, the ...
charges. Tetryl is a
nitramine Nitramide is a chemical compound with the molecular formula H2NNO2. Organyl derivatives of nitramide, RNHNO2 are termed nitroamines, and are widely used as explosives: examples include RDX and HMX. It is an isomer of hyponitrous acid. Struct ...
booster explosive, though its use has been largely superseded by
RDX RDX (abbreviation of "Research Department eXplosive") or hexogen, among other names, is an organic compound with the formula (O2N2CH2)3. It is a white solid without smell or taste, widely used as an explosive. Chemically, it is classified as a ...
. Tetryl is a sensitive secondary high explosive used as a booster, a small charge placed next to the detonator in order to propagate detonation into the main explosive charge.


Chemical properties

Tetryl is a yellow crystalline solid powder material, practically insoluble in water but soluble 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 ...
,
benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
and other solvents. When tetryl is heated, it first melts, then decomposes and explodes. It burns readily and is more easily detonated than
ammonium picrate Dunnite, also known as Explosive D or systematically as ammonium picrate, is an explosive developed in 1906 by US Army Major Beverly W. Dunn, who later served as the chief inspector of the Bureau of Transportation Explosives. Ammonium picrate is ...
or
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 ...
, being about as sensitive as
picric acid Picric acid is an organic compound with the formula (O2N)3C6H2OH. Its IUPAC name is 2,4,6-trinitrophenol (TNP). The name "picric" comes from el, πικρός (''pikros''), meaning "bitter", due to its bitter taste. It is one of the most acidic ...
. It is detonated by friction, shock, or spark. It remains stable at all temperatures which may be encountered in storage. It is generally used in the form of pressed pellets, and has been approved as the standard bursting charge for small-caliber projectiles, since it gives much better fragmentation than TNT. It has an
explosive velocity 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 23,600–23,900 feet per second (7200–7300 m/s). Tetryl is the basis for the service tetryl blasting caps necessary for positive detonation of TNT. A mixture of
mercury fulminate Mercury(II) fulminate, or Hg(CNO)2, is a primary explosive. It is highly sensitive to friction, heat and shock and is mainly used as a trigger for other explosives in percussion caps and detonators. Mercury(II) cyanate, though its chemical formu ...
and
potassium chlorate Potassium chlorate is a compound containing potassium, chlorine and oxygen, with the molecular formula KClO3. In its pure form, it is a white crystalline substance. After sodium chlorate, it is the second most common chlorate in industrial use. It ...
is included in the cap to ensure detonation of tetryl.


Environmental fate

The most toxic ordnance compounds, tetryl and 1,3,5-TNB, are also the most degradable. Therefore, these chemicals are expected to be short-lived in nature, and environmental impacts would not be expected in areas that are not currently subject to chronic inputs of these chemicals. Tetryl decomposes rapidly in
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 ...
/water solutions, as well as with heat. All aqueous samples expected to contain tetryl should be diluted with
acetonitrile Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not clas ...
prior to
filtration Filtration is a physical separation process that separates solid matter and fluid from a mixture using a ''filter medium'' that has a complex structure through which only the fluid can pass. Solid particles that cannot pass through the filter ...
and acidified to pH < 3. All samples expected to contain tetryl should not be exposed to temperatures above room temperature. In addition, degradation products of tetryl appear as a shoulder on the 2,4,6-TNT peak. Peak heights rather than peak areas should be used when tetryl is present in concentrations that are significant relative to the concentration of 2,4,6-TNT.


History

Tetryl was used mainly during World Wars I and II and later conflicts. Tetryl is usually used on its own, though can sometimes be found in compositions such as
tetrytol Tetrytol is a high explosive, comprising a mixture of tetryl and TNT. Typically, the proportion of ingredients (by weight) is 65%, 70%, 75% or 80% tetryl to 35%, 30%, 25% or 20% TNT. Tetryl and TNT do form a eutectic with a setting point of 67.5 ...
. Tetryl is no longer manufactured or used in the United States, but can still be found in legacy munitions such as the M14 anti-personnel
landmine A land mine is an explosive device concealed under or on the ground and designed to destroy or disable enemy targets, ranging from combatants to vehicles and tanks, as they pass over or near it. Such a device is typically detonated automati ...
.


Production

Tetryl is produced by slowly mixing
dimethylaniline ''N'',''N''-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It consists of a tertiary amine, featuring dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but comm ...
with concentrated
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 the presence of
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 ...
.


Health concerns

Although tetryl is among the most toxic explosive compounds, it is very short-lived. This combined with the fact that the health impacts of this compound are largely unstudied, not much is known about any health problems that this compound may cause. Epidemiological data shows that tetryl has most effect on the skin, acting as a strong irritant. Symptoms of skin sensitization such as dermatitis, itch, erythema, etc. may occur.CDC - NIOSH Pocket Guide to Chemical Hazards
/ref> Tetryl can also affect mucous membranes, the upper respiratory tract, and possibly the liver.


See also

*
Hexanitrobenzene Hexanitrobenzene, also known as HNB, is a high-density explosive compound with chemical formula , obtained by oxidizing the amine group of pentanitroaniline with hydrogen peroxide in sulfuric acid. Properties HNB has the undesirable property ...
*
Trinitrotoluene 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 reage ...
*
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

* Cooper, Paul W., ''Explosives Engineering'', New York: Wiley-VCH, 1996.


External links


Tetryl
Agency for Toxic Substances and Disease Registry The Agency for Toxic Substances and Disease Registry (ATSDR) is a federal public health agency within the United States Department of Health and Human Services. The agency focuses on minimizing human health risks associated with exposure to haza ...

Occupational Safety and Health Guideline for Tetryl
{{Webarchive, url=https://web.archive.org/web/20090227041309/http://www.osha.gov/SLTC/healthguidelines/tetryl/recognition.html , date=2009-02-27 , Occupational Safety & Health Administration Explosive chemicals Nitroamines