Difference between revisions of "Trinitrotoluene" - New World Encyclopedia

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! {{chembox header}} | Trinitrotoluene
 
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| Name || Trinitrotoluene
 
| Name || Trinitrotoluene
 
|-
 
|-
| Other Names || 2-Methyl-1,3,5-trinitrobenzene<br>2,4,6-Trinitrotoluene<br>TNT<br>Trotyl  
+
| Other Names || 2-Methyl-1,3,5-trinitrobenzene<br/>2,4,6-Trinitrotoluene<br/>TNT<br/>Trotyl  
 
|-
 
|-
 
| [[Empirical formula]] || [[Carbon|C]]<sub>7</sub>[[Hydrogen|H]]<sub>5</sub>[[Nitrogen|N]]<sub>3</sub>[[Oxygen|O]]<sub>6</sub>
 
| [[Empirical formula]] || [[Carbon|C]]<sub>7</sub>[[Hydrogen|H]]<sub>5</sub>[[Nitrogen|N]]<sub>3</sub>[[Oxygen|O]]<sub>6</sub>
Line 37: Line 37:
 
| [[Melting Point]] || 80.35 [[Degrees Celsius|°C]]
 
| [[Melting Point]] || 80.35 [[Degrees Celsius|°C]]
 
|-
 
|-
| [[Boiling Point]] || 295 °C (Decomposition)
+
| [[Boiling Point]] || 295 °C (Decomposition)
 
|-
 
|-
 
| [[Vapor pressure]] || 5.7 [[Pascal (unit)|Pa]] (81 °C)
 
| [[Vapor pressure]] || 5.7 [[Pascal (unit)|Pa]] (81 °C)
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|
 
|
 
*Well in ether, acetone, benzene
 
*Well in ether, acetone, benzene
*Badly in water  
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*Badly in water
 
|-
 
|-
 
! {{chembox header}} | Safety References
 
! {{chembox header}} | Safety References
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| [[Threshold Limit Value|TLV]] || 0.1 mg/m³
 
| [[Threshold Limit Value|TLV]] || 0.1 mg/m³
 
|-
 
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
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| {{chembox header}} | <small>Except where noted otherwise, data are given for<br/> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]</small>
 
|}
 
|}
  
'''Trinitrotoluene''' ('''TNT''') is an [[explosive]]. Its empirical formula is C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.
+
'''Trinitrotoluene''' or '''TNT''' (chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>) is a chemical [[explosive]] that has often been used in warfare. The purified material is a yellow, crystalline substance and is very toxic. Its formal name is ''2-methyl-1,3,5-trinitrobenzene'', in accordance with the nomenclature of the International Union of Pure and Applied Chemistry (IUPAC). First synthesized by [[Joseph Wilbrand]] in 1863, its large-scale production began in [[Germany]] in 1891. The explosive yield of TNT is considered the standard measure for the strength of [[bomb]]s and other explosives (see [[#TNT equivalent|TNT equivalent]] below).
 +
{{toc}}
 +
==History==
  
The name for TNT is, in accordance with the nomenclature of the [[IUPAC]]*, ''2-methyl-1,3,5-trinitrobenzene''. In this article the more common designation ''trinitrotoluene'' is used.
+
TNT was first made in 1863 by [[Germany|German]] [[chemist]] [[Joseph Wilbrand]], but its potential as an explosive was not recognized for several years, mainly because it was so hard to detonate and less powerful than other explosives. For example, in 1910, it was exempted from the UK's [[Explosives Act 1875]], that is, not actually being considered an explosive for manufacturing and storage purposes. Among its advantages, however, is its ability to be safely melted using [[steam]] or hot water, allowing it to be poured molten into shell cases. (This is how Vietnamese fighters made their mines out of American shells during the [[Vietnam War]].)
  
TNT was first synthesised by [[Joseph Wilbrand]]* in 1863, and the first large-scale production began in [[Germany]] in 1891.
+
[[Germany|German]] armed forces adopted it as an [[artillery]] [[shell (projectile)|shell]] filling in 1902. During the [[World War I|First World War]], the [[German Navy]] had the particular advantage of being able to detonate their TNT-filled armor-piercing shells after they had penetrated the armor of [[Great Britain|British]] [[capital ships]]. By contrast, the British [[Picric acid|lyddite]]-filled shells tended to explode as soon as they struck the German armor, thus expending much of their energy outside the ship. The British gradually started using it as replacement for [[lyddite]] in 1907.
  
The explosive yield of TNT is considered the standard measure of strength of [[bombs]]* and other [[explosives]]* (see [[#TNT equivalent|TNT equivalent]] below).
+
Because of the insatiable demand for explosives during the [[World War II|Second World War]], TNT was frequently mixed with 40 to 80 percent [[ammonium nitrate]], producing an explosive called ''[[amatol]]''. Although nearly as powerful as TNT (and much less expensive), amatol had the slight disadvantage of being [[hygroscopic]] (prone to absorbing moisture from the air). Another variation called ''minol'', consisting of amatol mixed with about 20 percent [[aluminum]] powder, was used by the British in mines and depth charges. Although blocks of pure TNT are available in various sizes (such as 250 g, 500 g, and 1 kg) it is more commonly encountered in explosive blends that comprise a variable percentage of TNT plus other ingredients, such as [[torpex]], [[tritonal]], [[pentolite]], and [[Composition B]].
 +
 
 +
==Synthesis==
 +
 +
Trinitrotoluene is synthesized in a stepwise procedure. First, [[toluene]] is nitrated with a mixture of [[sulfuric acid|sulfuric]] and [[nitric acid]]s. Even relatively low-concentration acid mixtures are capable of adding one or two nitro (NO<sub>2</sub>) groups to the toluene ring, producing mono- and dinitrotoluene. The nitro groups decrease the reactivity of the toluene drastically (because they are "electron-withdrawing" groups).
 +
 
 +
During the next stage, the mono- and dinitrotoluene are fully nitrated with a mixture of nitric acid and [[oleum]] (sulfuric acid with up to 60 percent dissolved [[sulfur trioxide]] (SO<sub>3</sub>)). This mixture is far more reactive and is capable of introducing the last (third) nitro group on the ring. The waste acid from this process is used for the first step of the reaction in industrial synthesis.
  
 
==Characteristics==
 
==Characteristics==
  
'''Trinitrotoluene''' takes the form of pale yellow, needle-shaped crystals and can be distilled in a vacuum. It is difficult to dissolve TNT in water; it is more soluble in [[ether]]*, [[acetone]]*, [[benzene]]*, and [[pyridine]]*. With its low melting point of 80.35 °C, TNT can be melted in water vapour and poured into forms. TNT is poisonous and skin contact can cause allergic reactions, causing the skin to turn a bright yellow-orange color.
+
Trinitrotoluene takes the form of pale yellow, needle-shaped crystals and can be distilled in a vacuum. It is difficult to dissolve TNT in water; it is more soluble in [[ether]], [[acetone]], [[benzene]], and [[pyridine]]. With its low [[melting point]] of 80.35 °C, TNT can be melted in steam and poured into containers. TNT is poisonous and skin contact can cause allergic reactions, causing the skin to turn a bright yellow-orange color.
  
 
* Water solubility: 130 mg/L at 20 °C
 
* Water solubility: 130 mg/L at 20 °C
 
* Steam pressure at 20 °C: 150 to 600 Pa
 
* Steam pressure at 20 °C: 150 to 600 Pa
  
* [[Detonation speed]]*: 6700-7000 m/s 6900 m/s (density: 1,6 g/cm³)
+
* [[Detonation speed]]: 6700-7000 m/s 6900 m/s (density: 1,6 g/cm³)
* [[Lead block test]]*: 300 ml/10 g
+
* [[Lead block test]]: 300 ml/10 g
* [[Sensitivity to impact]]*: 15 [[newton metre|N·m]] (1.5 [[kilopond|kp]]·[[metre|m]])
+
* [[Sensitivity to impact]]: 15 newton meter (N•m) (1.5 kilopound (kp)•meter (m))
 
* Friction sensitivity: to 353 N (36 kp) no reaction
 
* Friction sensitivity: to 353 N (36 kp) no reaction
  
 
===Toxicity===
 
===Toxicity===
  
Some military testing grounds are contaminated with TNT. Wastewater from munitions programs including contamination of surface and [[groundwater|subsurface waters]] may be colored pink as the result of TNT and [[RDX]]* contamination. Such contamination, called [[pinkwater]], may be difficult and expensive to [[remediation|remedy]]*.
+
Some military testing grounds are contaminated with TNT. Wastewater from munitions programs (including contaminated surface water and [[groundwater]] may be colored pink as a result of TNT and [[RDX]] contamination. Such contamination, called [[pinkwater]], may be difficult and expensive to [[remediation|remedy]].
  
TNT is quite [[toxic]]*. It can also be absorbed through the skin, and will cause irritation and bright yellow staining. During the [[World War I|First World War]], munition workers who handled the chemical found that their [[skin]]* turned bright yellow, which led to the nickname "canary girls" or simply "canaries" to describe such workers. TNT would also eventually make ginger hair turn green. A 1916 British Government inquiry on female workers at the [[Royal Arsenal]]*, [[Woolwich]]*, found that 37% had severe pains due to 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.
+
TNT is quite [[toxic]]. It can also be absorbed through the skin, and will cause irritation and bright yellow staining. During the [[World War I|First World War]], munition workers who handled the chemical found that their [[skin]] turned bright yellow. That led to the nickname "canary girls" or simply "canaries" to describe those workers. TNT would also eventually make ginger hair turn green. A 1916 British Government inquiry on female workers at the [[Royal Arsenal]], [[Woolwich]], found that 37 percent had severe pains due to loss of [[appetite]], [[nausea]], and [[constipation]]; 25 percent suffered from [[dermatitis]]; and 34 percent 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 trinitrotoluene 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 black [[urine]].
+
People exposed to trinitrotoluene 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 black [[urine]].
 
 
==History==
 
TNT was first made in 1863 by a [[Germany|German]] [[chemist]] [[Joseph Wilbrand]], but its potential was not seen for several years, mainly because it was so hard to detonate and because it was less powerful than other explosives.  Among its advantages, however, is its ability to be safely melted using [[steam]] or hot water, allowing it to be poured molten into shell cases. (This is how Vietnamese fighters made their mines out of American shells during the [[Vietnam War]].) It is also so insensitive that, for example, in 1910 it was exempted from the UK's [[Explosives Act 1875]], i.e. not actually being considered an explosive for the purposes of manufacture and storage.
 
 
 
The [[Germany|German]] armed forces adopted it as an [[artillery]] [[shell (projectile)|shell]] filling in 1902. A particular advantage that it gave the [[German Navy]] in the [[World War I|First World War]] was being able to detonate their TNT-filled armour-piercing shells after they had penetrated the armour of British [[capital ships]], whereas the British [[Picric acid|lyddite]]-filled shells tended to explode as soon as they struck the German armour, and thus expended much of their energy outside the ship.  The British gradually started using it as replacement for lyddite in 1907.
 
 
 
Because of the insatiable demand for explosives during the Second World War, TNT was frequently mixed with 40%-80% [[ammonium nitrate]], producing an explosive called [[amatol]]. Although nearly as powerful as TNT (and much less expensive) amatol suffered from the slight disadvantage of being [[hygroscopic]] (prone to absorbing water). Another variation called ''minol'', consisting of amatol mixed with about 20% [[aluminium|aluminum]] powder, was used by the British in mines and depth charges. Although blocks of pure TNT are available in various sizes (e.g. 250 g, 500 g and 1 kg) it is more commonly encountered in explosive blends which comprise a variable percentage of TNT plus other ingredients, e.g. [[torpex]], [[tritonal]], [[pentolite]] and [[Composition B]].
 
 
 
==Preparation== 
 
The synthesis is done in a stepwise procedure. First, [[toluene]] is nitrated with a mixture of [[sulfuric acid|sulfuric]] and [[nitric acid]]. Even lower-concentration acid mixtures are capable of doing the first and second introduction of a nitrogroup. The nitrogroups decrease the reactivity of the toluene drastically because they are electron-withdrawing groups. After separation, the mono- and dinitrotoluene is fully nitrated with a mixture of nitric acid and [[oleum]] (sulfuric acid with up to 60% dissolved [[sulfur trioxide|SO<sub>3</sub>]]). This mixture is far more reactive and is capable of introducing the last nitrogroup. The waste acid from this process is used for the first step of the reaction in industrial synthesis.
 
  
 
== TNT equivalent ==
 
== TNT equivalent ==
  
'''TNT equivalent''' is a unit of energy commonly used to quantify large amounts of energy. One ton of TNT releases 4.184×10<sup>9</sup> joules upon explosion, therefore 1 kiloton of TNT is 4.184×10<sup>12</sup> [[joules]], and 1 megaton of TNT is 4.184×10<sup>15</sup> joules.
+
''TNT equivalent'' is a unit of energy commonly used to quantify large amounts of energy. One ton of TNT releases 4.184×10<sup>9</sup> joules upon explosion, therefore one kiloton of TNT is 4.184×10<sup>12</sup> [[joules]], and one megaton of TNT is 4.184×10<sup>15</sup> joules.
  
A megaton is a large amount of energy. The first [[atomic bomb]] dropped on [[Hiroshima]] on [[August 6]], [[1945]] exploded with the energy of about 20 kilotons of TNT (~8.4×10<sup>13</sup> joules).  
+
A megaton is a large amount of energy. The first [[atomic bomb]] dropped on [[Hiroshima]] on August 6, 1945, exploded with the energy of about 20 kilotons of TNT (~8.4×10<sup>13</sup> joules).
  
Current [[nuclear warhead]]s in [[Russia]] and the [[USA]] stockpiles range in [[nuclear weapon yield|yield]] from 100 kt to 20 Mt TNT equivalent. The largest bomb ever dropped, the [[Tsar Bomba]], had a yield of about 50 Mt.
+
Current [[nuclear warhead]]s in [[Russia]]n and [[USA|U.S.]] stockpiles range in [[nuclear weapon yield|yield]] from 100 kt to 20 Mt TNT equivalent. The largest bomb ever dropped, the [[Tsar Bomba]], had a yield of about 50 Mt.
  
About 1 Mt equivalent exploded on the ground or slightly above ground creates a crater about 0.3 miles (0.5 km) in diameter and levels practically everything in a few mile or kilometer radius.
+
About one Mt equivalent exploded on the ground or slightly above ground creates a crater about 0.3 miles (0.5 km) in diameter and levels practically everything in a radius of a few miles or kilometers.
  
 
==See also==
 
==See also==
  
*[[dynamite]]
+
* [[dynamite]]
*[[hexanitrobenzene]]
+
* [[explosive]]
*[[megaton]]
+
 
*[[tetryl]]
+
== References ==
  
==External links==
+
* Akhavan, J. 2004. ''The Chemistry of Explosives'', 2nd edition. Cambridge, UK: The Royal Society of Chemistry. ISBN 0854046402
*[http://www.compchemwiki.org/index.php?title=Trinitrotoluene Computational Chemistry Wiki]
+
* Cooper, Paul W., and Stanley R. Kurowski. 1996. ''Introduction to the Technology of Explosives''. New York, NY: Wiley-VCH. ISBN 047118635X
*[http://www.roguesci.org/megalomania/explo/trinitrotoluene.html] Detailed Preparation
+
* Cooper, Paul W. 1996. ''Explosives Engineering''. New York, NY: Wiley-VCH. ISBN 0471186368
 +
* Meyer, Rudolf, Joseph Kohler, and Axel Homburg. 2002. ''Explosives'', 5th revised edition. New York, NY: Wiley-VCH. ISBN 3527302670
  
{{ChemicalSources}}
 
  
 
[[Category:Physical sciences]]
 
[[Category:Physical sciences]]

Latest revision as of 16:14, 17 December 2015

Trinitrotoluene
Trinitrotoluene.png
General
Name Trinitrotoluene
Other Names 2-Methyl-1,3,5-trinitrobenzene
2,4,6-Trinitrotoluene
TNT
Trotyl
Empirical formula C7H5N3O6
CAS Number 118-96-7
PubChem 8376
Short description Pale, yellow, needle-shaped crystals
Characteristics
Molar mass 227.131 g/mol
Phase Solid
Shock sensitivity Insensitive
Friction sensitivity Insensitive
Density 1.654 g/cm³
Explosive velocity 6,900 m/s
RE factor 1.00
Melting Point 80.35 °C
Boiling Point 295 °C (Decomposition)
Vapor pressure 5.7 Pa (81 °C)
Solubility
  • Well in ether, acetone, benzene
  • Badly in water
Safety References
NFPA 704

NFPA 704.svg

4
3
4
 
R/S Statements

R: 2-23/24/25-33-51/53
S: 35-45-61

TLV 0.1 mg/m³
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)

Trinitrotoluene or TNT (chemical formula C7H5N3O6) is a chemical explosive that has often been used in warfare. The purified material is a yellow, crystalline substance and is very toxic. Its formal name is 2-methyl-1,3,5-trinitrobenzene, in accordance with the nomenclature of the International Union of Pure and Applied Chemistry (IUPAC). First synthesized by Joseph Wilbrand in 1863, its large-scale production began in Germany in 1891. The explosive yield of TNT is considered the standard measure for the strength of bombs and other explosives (see TNT equivalent below).

History

TNT was first made in 1863 by German chemist Joseph Wilbrand, but its potential as an explosive was not recognized for several years, mainly because it was so hard to detonate and less powerful than other explosives. For example, in 1910, it was exempted from the UK's Explosives Act 1875, that is, not actually being considered an explosive for manufacturing and storage purposes. Among its advantages, however, is its ability to be safely melted using steam or hot water, allowing it to be poured molten into shell cases. (This is how Vietnamese fighters made their mines out of American shells during the Vietnam War.)

German armed forces adopted it as an artillery shell filling in 1902. During the First World War, the German Navy had the particular advantage of being able to detonate their TNT-filled armor-piercing shells after they had penetrated the armor of British capital ships. By contrast, the British lyddite-filled shells tended to explode as soon as they struck the German armor, thus expending much of their energy outside the ship. The British gradually started using it as replacement for lyddite in 1907.

Because of the insatiable demand for explosives during the Second World War, TNT was frequently mixed with 40 to 80 percent ammonium nitrate, producing an explosive called amatol. Although nearly as powerful as TNT (and much less expensive), amatol had the slight disadvantage of being hygroscopic (prone to absorbing moisture from the air). Another variation called minol, consisting of amatol mixed with about 20 percent aluminum powder, was used by the British in mines and depth charges. Although blocks of pure TNT are available in various sizes (such as 250 g, 500 g, and 1 kg) it is more commonly encountered in explosive blends that comprise a variable percentage of TNT plus other ingredients, such as torpex, tritonal, pentolite, and Composition B.

Synthesis

Trinitrotoluene is synthesized in a stepwise procedure. First, toluene is nitrated with a mixture of sulfuric and nitric acids. Even relatively low-concentration acid mixtures are capable of adding one or two nitro (NO2) groups to the toluene ring, producing mono- and dinitrotoluene. The nitro groups decrease the reactivity of the toluene drastically (because they are "electron-withdrawing" groups).

During the next stage, the mono- and dinitrotoluene are fully nitrated with a mixture of nitric acid and oleum (sulfuric acid with up to 60 percent dissolved sulfur trioxide (SO3)). This mixture is far more reactive and is capable of introducing the last (third) nitro group on the ring. The waste acid from this process is used for the first step of the reaction in industrial synthesis.

Characteristics

Trinitrotoluene takes the form of pale yellow, needle-shaped crystals and can be distilled in a vacuum. It is difficult to dissolve TNT in water; it is more soluble in ether, acetone, benzene, and pyridine. With its low melting point of 80.35 °C, TNT can be melted in steam and poured into containers. TNT is poisonous and skin contact can cause allergic reactions, causing the skin to turn a bright yellow-orange color.

  • Water solubility: 130 mg/L at 20 °C
  • Steam pressure at 20 °C: 150 to 600 Pa
  • Detonation speed: 6700-7000 m/s 6900 m/s (density: 1,6 g/cm³)
  • Lead block test: 300 ml/10 g
  • Sensitivity to impact: 15 newton meter (N•m) (1.5 kilopound (kp)•meter (m))
  • Friction sensitivity: to 353 N (36 kp) no reaction

Toxicity

Some military testing grounds are contaminated with TNT. Wastewater from munitions programs (including contaminated surface water and groundwater may be colored pink as a result of TNT and RDX contamination. Such contamination, called pinkwater, may be difficult and expensive to remedy.

TNT is quite toxic. It can also be absorbed through the skin, and will cause irritation and bright yellow staining. During the First World War, munition workers who handled the chemical found that their skin turned bright yellow. That led to the nickname "canary girls" or simply "canaries" to describe those workers. TNT would also eventually make ginger hair turn green. A 1916 British Government inquiry on female workers at the Royal Arsenal, Woolwich, found that 37 percent had severe pains due to loss of appetite, nausea, and constipation; 25 percent suffered from dermatitis; and 34 percent 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 trinitrotoluene 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 black urine.

TNT equivalent

TNT equivalent is a unit of energy commonly used to quantify large amounts of energy. One ton of TNT releases 4.184×109 joules upon explosion, therefore one kiloton of TNT is 4.184×1012 joules, and one megaton of TNT is 4.184×1015 joules.

A megaton is a large amount of energy. The first atomic bomb dropped on Hiroshima on August 6, 1945, exploded with the energy of about 20 kilotons of TNT (~8.4×1013 joules).

Current nuclear warheads in Russian and U.S. stockpiles range in yield from 100 kt to 20 Mt TNT equivalent. The largest bomb ever dropped, the Tsar Bomba, had a yield of about 50 Mt.

About one Mt equivalent exploded on the ground or slightly above ground creates a crater about 0.3 miles (0.5 km) in diameter and levels practically everything in a radius of a few miles or kilometers.

See also

References
ISBN links support NWE through referral fees

  • Akhavan, J. 2004. The Chemistry of Explosives, 2nd edition. Cambridge, UK: The Royal Society of Chemistry. ISBN 0854046402
  • Cooper, Paul W., and Stanley R. Kurowski. 1996. Introduction to the Technology of Explosives. New York, NY: Wiley-VCH. ISBN 047118635X
  • Cooper, Paul W. 1996. Explosives Engineering. New York, NY: Wiley-VCH. ISBN 0471186368
  • Meyer, Rudolf, Joseph Kohler, and Axel Homburg. 2002. Explosives, 5th revised edition. New York, NY: Wiley-VCH. ISBN 3527302670

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