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{{chembox new| ImageFile = Trinitrotoluene.svg| ImageSize = 150px| ImageFile1 = TNT-3D-balls.png| ImageSize1 = 150px| IUPACName = 2-Methyl-1,3,5-trinitrobenzene| OtherNames = 2,4,6-Trinitrotoluene
Trotyl
2,4,6-Trinitromethylbenzene| Section1 = {{Chembox Identifiers| Abbreviations = TNT| CASNo = 118-96-7| EINECS =| PubChem = 8376| SMILES = Cc1c(cc(cc1N(=O)=O)N(=O)=O)N(=O)=O| InChI =| RTECS =| MeSHName =| ChEBI =| KEGG =| ATCCode_prefix =| ATCCode_suffix =| ATC_Supplemental =-->| Section2 = {{Chembox Properties| Formula Carbon7Hydrogen5Nitrogen3
Oxygen6| MolarMass = 227.131 g/mol| Appearance = yellow needles| Density = 1.654 g/cm³| MeltingPt = 80.35 °C| Melting_notes =| BoilingPt = 295 °C| Boiling_notes = decomposition| Solubility = 130 mg/L of H2O (20 °C)| SolubleOther =
ether acetone
benzene pyridine
[hexanitrobenzene-->-->
Trinitrotoluene (
TNT) is a chemical compound with the formula C6H2(NO2)3CH3. This yellow-coloured solid is a reagent (reactant) in chemistry but is best known as a useful
explosive material with convenient handling properties. The explosive yield of TNT is considered the TNT equivalent of
bombs and other
explosives. In chemistry, TNT is used to generate Charge transfer complex.
Explosive character
Upon detonation, TNT decomposes as follows:
2 C7H5N3O6 → 3 N2 + 5 H2O + 7 CO + 7 C
The reaction is exothermic but has a high activation energy. Because of the production of carbon, TNT explosions have a sooty appearance.{] || Insensitive|-|
Friction sensitivity ] || ~100|-|
Relative effectiveness factor || 1.00|-| Explosive velocity ] (density: 1,6 g/cm³)|-| Heat of explosion || 3,977 energy density|-| Steam pressure at 20 °C|| 150 to 600 Pa|-|
Trauzl lead block test|| 300 ml/10 g|-| Sensitivity to impact || 15 newton metre|-| Friction sensitivity|| to 353 N (36 kp) no reaction|-|}
TNT used to be the reference point for the Figure of Insensitivity (exactly 100 by definition), but the reference point is now the more sensitive (or less insensitive)
RDX which is deemed to have a FofI of exactly 80. The value for the heat of explosion is taken fromErich Ammedick:
Militärchemie. eine Einführung. 4. Auflage. In:
Bausteine der Chemie. VEB Deutscher Verlag für Grundstoffindustrie, Leipzig 1980, ISBN 978-3342000372 (German).
Toxicity, environmental concerns, and degradation
TNT is poisonous, and
skin contact can cause skin irritation, causing the skin to turn a bright yellow-orange color. During the World War I, munition workers who handled the chemical found that their skin turned bright yellow, which resulted in their acquiring the nickname "canary girls" or simply "canaries." TNT also slowly changes ginger-coloured hair to green. A 1916 British Government inquiry on female workers at the Royal Arsenal,
Woolwich, found that 37% had severe pains from loss of appetite,
nausea, and
constipation; 25% suffered from dermatitis; and 34% experienced changes in menstruation. Before respirators and protective grease applied to the skin were introduced, about 100 workers died from the disease.
People exposed to TNT over a prolonged period tend to experience
anemia and abnormal liver functions. Blood and liver effects,
spleen enlargement and other harmful effects on the
immune system have also been found in animals that ingested or breathed trinitrotoluene. There is evidence that TNT adversely affects male fertility, and TNT is listed as a possible human carcinogen. Consumption of TNT produces red
urine.
Some military testing grounds are contaminated with TNT. Wastewater from munitions programs including contamination of surface and
groundwater may be colored pink because of the presence of TNT. Such contamination, called "pinkwater", may be difficult and expensive to remediation.
Applications
TNT is one of the most commonly used explosives for military and industrial applications. It is valued because of its insensitivity to shock and friction, which reduces the risk of unexpected detonations. TNT melts at 80 °C (180 °F), far below the temperature at which it will spontaneously detonate, allowing it to be poured as well as safely combined with other explosives. TNT neither absorbs nor dissolves in water, which allows it to be used effectively in wet environments. Additionally, it is comparatively stable when compared to other high explosives.
Although blocks of pure TNT are available in various sizes (250, 500, and 1,000 g), it is more commonly encountered in
synergistic explosive blends that comprise a variable percentage of TNT plus other ingredients. Examples of explosive blends containing TNT include
History
TNT was first prepared in 1863 by
Germany chemist
Joseph Wilbrand and originally used as a yellow dye. Its potential as an explosive was not appreciated for several years mainly because it was so difficult to detonate and because it was less powerful than alternatives. TNT can be safely poured when liquid into shell cases, and is so insensitive that in 1910, it was exempted from the UK's Explosives Act 1875 and was not considered an explosive for the purposes of manufacture and storage.
The German armed forces adopted it as a filling for
artillery shell (projectile)s in 1902. TNT-filled armour-piercing shells would explode after they had penetrated the armour of British capital ships, whereas the British
Picric acid-filled shells tended to explode upon striking armour, thus expending much of their energy outside the ship. The British started replacing lyddite with TNT in 1907.
Preparation
TNT is synthesized in a two-step process. First,
toluene is nitrated with a mixture of
sulfuric acid and nitric acid to produce mono- and
dinitrotoluene. Next, the mixture of mono- and dinitrotoluene is further nitrated with a mixture of nitric acid and oleum, a more potent nitration recipe. The waste acid from this second step can be recycled for use in the first.
Difference from dynamite
It is a common misconception that TNT and dynamite are the same, or that dynamite contains TNT. In fact, whereas TNT is a specific chemical compound, dynamite is an absorbent mixture soaked in
nitroglycerin that is compressed into a cylindrical shape and wrapped in paper.
See also
References
External links
- Video showing the shockwave and typical black smoke cloud from a pure TNT detonation
- Video showing detonation of 50 tons of TNT in 1963 during Anglo-Australian "Operation Blowdown"
- Video showing detonation of 453 metric tons of TNT - note shockwave and black smoke residue
- Computational Chemistry Wiki
- Detailed Preparation
{{chembox new| ImageFile = Trinitrotoluene.svg| ImageSize = 150px| ImageFile1 = TNT-3D-balls.png| ImageSize1 = 150px| IUPACName = 2-Methyl-1,3,5-trinitrobenzene| OtherNames = 2,4,6-Trinitrotoluene
Trotyl
2,4,6-Trinitromethylbenzene| Section1 = {{Chembox Identifiers| Abbreviations = TNT| CASNo = 118-96-7| EINECS =| PubChem = 8376| SMILES = Cc1c(cc(cc1N(=O)=O)N(=O)=O)N(=O)=O| InChI =| RTECS =| MeSHName =| ChEBI =| KEGG =| ATCCode_prefix =| ATCCode_suffix =| ATC_Supplemental =-->| Section2 = {{Chembox Properties| Formula Carbon7
Hydrogen5
Nitrogen3
Oxygen6| MolarMass = 227.131 g/mol| Appearance = yellow needles| Density = 1.654 g/cm³| MeltingPt = 80.35 °C| Melting_notes =| BoilingPt = 295 °C| Boiling_notes = decomposition| Solubility = 130 mg/L of H2O (20 °C)| SolubleOther = ether acetone
benzene pyridine
[hexanitrobenzene-->-->
Trinitrotoluene (
TNT) is a chemical compound with the formula C6H2(NO2)3CH3. This yellow-coloured solid is a reagent (reactant) in chemistry but is best known as a useful
explosive material with convenient handling properties. The explosive yield of TNT is considered the TNT equivalent of bombs and other
explosives. In chemistry, TNT is used to generate
Charge transfer complex.
Explosive character
Upon detonation, TNT decomposes as follows:
2 C7H5N3O6 → 3 N2 + 5 H2O + 7 CO + 7 C
The reaction is exothermic but has a high
activation energy. Because of the production of
carbon, TNT explosions have a sooty appearance.{] || Insensitive|-| Friction sensitivity ] || ~100|-|
Relative effectiveness factor || 1.00|-| Explosive velocity ] (density: 1,6 g/cm³)|-| Heat of explosion || 3,977
energy density|-| Steam pressure at 20 °C|| 150 to 600 Pa|-|
Trauzl lead block test|| 300 ml/10 g|-| Sensitivity to impact || 15 newton metre|-| Friction sensitivity|| to 353 N (36 kp) no reaction|-|}
TNT used to be the reference point for the Figure of Insensitivity (exactly 100 by definition), but the reference point is now the more sensitive (or less insensitive)
RDX which is deemed to have a FofI of exactly 80. The value for the heat of explosion is taken fromErich Ammedick:
Militärchemie. eine Einführung. 4. Auflage. In:
Bausteine der Chemie. VEB Deutscher Verlag für Grundstoffindustrie, Leipzig 1980, ISBN 978-3342000372 (German).
Toxicity, environmental concerns, and degradation
TNT is poisonous, and
skin contact can cause skin irritation, causing the skin to turn a bright yellow-orange color. During the World War I, munition workers who handled the chemical found that their skin turned bright yellow, which resulted in their acquiring the nickname "canary girls" or simply "canaries." TNT also slowly changes ginger-coloured hair to green. A 1916 British Government inquiry on female workers at the
Royal Arsenal, Woolwich, found that 37% had severe pains from loss of
appetite, nausea, and constipation; 25% suffered from
dermatitis; and 34% experienced changes in menstruation. Before
respirators and protective grease applied to the skin were introduced, about 100 workers died from the disease.
People exposed to TNT over a prolonged period tend to experience anemia and abnormal liver functions.
Blood and liver effects, spleen enlargement and other harmful effects on the
immune system have also been found in animals that ingested or breathed trinitrotoluene. There is evidence that TNT adversely affects male
fertility, and TNT is listed as a possible human
carcinogen. Consumption of TNT produces red
urine.
Some military testing grounds are contaminated with TNT. Wastewater from munitions programs including contamination of surface and groundwater may be colored pink because of the presence of TNT. Such contamination, called "
pinkwater", may be difficult and expensive to
remediation.
Applications
TNT is one of the most commonly used explosives for military and industrial applications. It is valued because of its insensitivity to shock and friction, which reduces the risk of unexpected detonations. TNT melts at 80 °C (180 °F), far below the temperature at which it will spontaneously detonate, allowing it to be poured as well as safely combined with other explosives. TNT neither absorbs nor dissolves in water, which allows it to be used effectively in wet environments. Additionally, it is comparatively stable when compared to other high explosives.
Although blocks of pure TNT are available in various sizes (250, 500, and 1,000 g), it is more commonly encountered in synergistic explosive blends that comprise a variable percentage of TNT plus other ingredients. Examples of explosive blends containing TNT include
History
TNT was first prepared in 1863 by Germany chemist
Joseph Wilbrand and originally used as a yellow dye. Its potential as an explosive was not appreciated for several years mainly because it was so difficult to detonate and because it was less powerful than alternatives. TNT can be safely poured when liquid into shell cases, and is so insensitive that in 1910, it was exempted from the UK's Explosives Act 1875 and was not considered an explosive for the purposes of manufacture and storage.
The German armed forces adopted it as a filling for artillery shell (projectile)s in 1902. TNT-filled armour-piercing shells would explode after they had penetrated the armour of British
capital ships, whereas the British
Picric acid-filled shells tended to explode upon striking armour, thus expending much of their energy outside the ship. The British started replacing lyddite with TNT in 1907.
Preparation
TNT is synthesized in a two-step process. First, toluene is nitrated with a mixture of
sulfuric acid and nitric acid to produce mono- and dinitrotoluene. Next, the mixture of mono- and dinitrotoluene is further nitrated with a mixture of nitric acid and oleum, a more potent nitration recipe. The waste acid from this second step can be recycled for use in the first.
Difference from dynamite
It is a common
misconception that TNT and
dynamite are the same, or that dynamite contains TNT. In fact, whereas TNT is a specific chemical compound, dynamite is an absorbent mixture soaked in nitroglycerin that is compressed into a cylindrical shape and wrapped in paper.
See also
- Megaton
- Explosives used during WW II
References
External links
- Video showing the shockwave and typical black smoke cloud from a pure TNT detonation
- Video showing detonation of 50 tons of TNT in 1963 during Anglo-Australian "Operation Blowdown"
- Video showing detonation of 453 metric tons of TNT - note shockwave and black smoke residue
- Computational Chemistry Wiki
- Detailed Preparation
Trinitrotoluene - Wikipedia, the free encyclopedia
Trinitrotoluene (TNT) is a chemical compound with the formula C 6 H 2 (NO 2) 3 CH 3. This yellow-coloured solid is a reagent (reactant) in chemistry but is best known as a useful ...
trinitrotoluene definition of trinitrotoluene in the Free Online ...
trinitrotoluene or TNT (trī'nī'trōtŏl`y ēn), CH 3 C 6 H 2 (NO 2) 3, crystalline, aromatic compound that melts at 81°C;. It is prepared by the nitration of toluene.
trinitrotoluene - definition of trinitrotoluene by the Free Online ...
tnt.
trinitrotoluene - definition of trinitrotoluene in the Medical ...
trinitrotoluene /tri·ni·tro·tol·u·ene/ (TNT) (-tol´u-en) a high explosive derived from toluene; it sometimes causes poisoning in those who work with it, marked by dermatitis ...
Impact of transgenic tobacco on trinitrotoluene (TNT) contaminated ...
Environmental contamination with recalcitrant toxic chemicals presents a serious and widespread problem to the functional capacity of soil. Soil bacteria play an essential role in ...
trinitrotoluene - Hutchinson encyclopedia article about ...
TNT. Abbreviation for trinitrotoluene, CH 3 C 6 H 2 (NO 2) 3, a powerful high explosive. It is a yellow solid, prepared in several isomeric forms from toluene by using sulphuric ...
TNT
An Explosive Material. 2,4,6-trinitrotoluene is better known by its initials, TNT. It is an important explosive, since it can very quickly change from a solid into hot expanding ...
It07:Trinitrotoluene - ChemWiki
edit] 2,4,6-Trinitrotoluene (TNT) [edit] 3D structure and crystal unit cell. 1. Interactive 3D representation of TNT. Right click on molecule to explore
trinitrotoluene -- Britannica Online Encyclopedia
Britannica online encyclopedia article on trinitrotoluene:a pale yellow, solid organic nitrogen compound used chiefly as an explosive, prepared by stepwise nitration of toluene.
Strathprints - Polymorphism in 2-4-6 trinitrotoluene
Two crystal structures of 2-4-6 trinitrotoluene (TNT) are given, the monoclinic form (a0 ) 1.49113 (1) nm, b0 ) 0.60340 (1) nm, c0 ) 2.08815(3) nm, C
