Chapter 1 Trinitrotoluene

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"TNT" redirects here. For other uses, see TNT (disambiguation).

Trinitrotoluene

Names

IUPAC name

2-Methyl-1,3,5-trinitrobenzene

Other names

2,4,6-Trinitrotoluene,

TNT, Trilite, Tolite, Trinol, Trotyl, Tritolo, Tritolol,

Triton, Tritone, Trotol, Trinitrotoluol,

2,4,6-Trinitromethylbenzene

Identifiers

Abbreviations TNT

CAS Registry

Number 118-96-7

ChEMBL ChEMBL1236345

ChemSpider 8073

DrugBank DB01676

EC number 204-289-6

InChI[show]

Jmol-3D images Image

KEGG C16391

PubChem 11763

RTECS number XU0175000

SMILES[show]

UNII H43RF5TRM5

UN number

0209 Dry or wetted with <

30% water

0388, 0389 Mixtures with

trinitrobenzene,

hexanitrostilbene

Properties

Molecular formula C7H5N3O6

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Molar mass 227.13 gmol1

Appearance

Pale yellow solid. Loose

"needles", flakes or prills before

melt-casting. A solid block after

being poured into a casing.

Density 1.654 g/cm3

Melting point 80.35 C (176.63 F; 353.50 K)

Boiling point 240.0 C (464.0 F; 513.1 K)

(decomposes)[1]

Solubility in water 0.13 g/L (20 C)

Solubility in ether,

acetone, benzene,

pyridine

soluble

Explosive data

Shock sensitivity Insensitive

Friction sensitivity Insensitive to 353 N

Detonation velocity 6900 m/s

RE factor 1.00

Hazards

MSDS ICSC 0967

EU Index 609-008-00-4

EU classification

Explosive (E)

Toxic (T)

Dangerous for the environment

(N)

R-phrases R2, R23/24/25, R33, R51/53

S-phrases (S1/2), S35, S45, S61

NFPA 704

4

2

4 Flash point 167 C (333 F; 440 K)

Related compounds

Related compounds

picric acid

hexanitrobenzene

2,4-Dinitrotoluene

Except where noted otherwise, data is given for

materials in their standard state (at 25 C (77 F),

100 kPa)

verify (what is: / ?)

Infobox references

Trinitrotoluene /tranatrtlj.in/ (TNT), or more specifically 2,4,6-trinitrotoluene, is a chemical

compound with the formula C6H2(NO2)3CH3. This yellow-colored solid is sometimes used as a reagent in

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chemical synthesis, but it is best known as a useful explosive material with convenient handling properties.

The explosive yield of TNT is considered to be the standard measure of strength of bombs and other

explosives. In chemistry, TNT is used to generate charge transfer salts.

Contents

1 History

2 Preparation

3 Applications

4 Explosive character

5 Energy content

6 Detection

7 Safety and toxicity

8 Ecological impact

o 8.1 Aqueous solubility

o 8.2 Soil adsorption

o 8.3 Chemical breakdown

o 8.4 Biodegradation

9 See also

10 References

11 External links

History

Trinitrotoluene melting at 81 C

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M107 artillery shells. All are labelled to indicate a filling of "Comp B" (mixture of TNT and RDX) and have

fuzes fitted

Breakdown of production by branch of TNT in the German army between 1941 and the first quarter of 1944

by thousands of tons per month

Detonation of the 500-ton TNT explosive charge as part of Operation Sailor Hat in 1965. The white blast-

wave is visible on the water surface and a shock condensation cloud is visible overhead.

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World War I-era HE artillery shell for a 9.2 inch howitzer. The red band indicates it is filled and the green

band (marked "Trotyl") indicates that the filling is TNT

TNT was first prepared in 1863 by German chemist Julius Wilbrand[2] 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.[3]

The German armed forces adopted it as a filling for artillery shells in 1902. TNT-filled armour-piercing

shells would explode after they had penetrated the armour of British capital ships, whereas the British

lyddite-filled shells tended to explode upon striking armour, thus expending much of their energy outside the

ship.[3] The British started replacing lyddite with TNT in 1907.

The United States Navy continued filling armor piercing shells with explosive D after some other nations

had switched to TNT; but began filling naval mines, bombs, depth charges, and torpedo warheads with

burster charges of crude grade B TNT with the color of brown sugar and requiring an explosive booster

charge of granular crystallized grade A TNT for detonation. High explosive shells were filled with grade A

TNT, which became preferred for this other use as industrial chemical capacity became available for

removing xylene and similar hydrocarbons from the toluene feedstock and other nitrotoluene isomer

byproducts from the nitrating reactions.[4]

TNT is still widely used by the United States military, as well as construction companies around the world.

The majority of TNT currently used by the US military is manufactured by Radford Army Ammunition

Plant near Radford, Virginia.[citation needed]

Preparation

In industry, TNT is produced in a three-step process. First, toluene is nitrated with a mixture of sulfuric and

nitric acid to produce mononitrotoluene (MNT). The MNT is separated and then renitrated to dinitrotoluene

or DNT. In the final step, the DNT is nitrated to trinitrotoluene or TNT using an anhydrous mixture of nitric

acid and oleum. Nitric acid is consumed by the manufacturing process, but the diluted sulfuric acid can be

reconcentrated and reused. Subsequent to nitration, TNT is stabilized by a process called sulfitation, where

the crude TNT is treated with aqueous sodium sulfite solution in order to remove less stable isomers of TNT

and other undesired reaction products. The rinse water from sulphitation is known as red water and is a

significant pollutant and waste product of TNT manufacture.[5]

Control of nitrogen oxides in feed nitric acid is very important because free nitrogen dioxide can result in

oxidation of the methyl group of toluene. This reaction is highly exothermic and carries with it the risk of a

runaway reaction leading to an explosion.

In the laboratory, 2,4,6-trinitrotoluene is produced by a two step process. A nitrating mixture of concentrated

nitric and sulfuric acids is used to nitrate toluene to a mixture of mono- and di-nitrotoluene isomers, with

cooling to maintain careful temperature control. The nitrated toluenes are then separated, washed with dilute

sodium bicarbonate to remove oxides of nitrogen, and then carefully nitrated with a mixture of fuming nitric

acid and sulfuric acid. Towards the end of the nitration, the mixture is heated on a steam bath. The

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trinitrotoluene is separated, washed with a dilute solution of sodium sulfite and then recrystallized from

alcohol.

Applications

TNT is one of the most commonly used explosives for military and industrial applications. It is valued partly

because of its insensitivity to shock and friction, which reduces the risk of accidental detonation, compared

to other more sensitive high explosives such as nitroglycerin. TNT melts at 80 C (176 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 stable compared to other high explosives.

In order to initiate an explosion, TNT must first be detonated using a pressure wave from a more sensitive

explosive called an explosive booster.

Although blocks of TNT are available in various sizes (e.g. 250 g, 500 g, 1,000 g), it is more commonly

encountered in synergistic explosive blends comprising a variable percentage of TNT plus other ingredients.

Examples of explosive blends containing TNT include:

Amatex: (ammonium nitrate and RDX) [6]

Amatol:(ammonium nitrate [7])

Ammonal: (ammonium nitrate and aluminium powder plus sometimes charcoal).

Baratol: ( barium nitrate and wax [8])

Composition B ( RDX and paraffin wax [9] )

Composition H6

Cyclotol (RDX) [10]

Ednatol

Hexanite [11](hexanitrodiphenylamine[12][13]).

Minol

Octol

Pentolite

Picratol

Tetrytol

Torpex

Tritonal

Explosive character

Upon detonation, TNT decomposes as follows:

2 C7H5N3O6 3 N2 + 5 H2O + 7 CO + 7 C

2 C7H5N3O6 3 N2 + 5 H2 + 12 CO + 2 C

The reaction is exothermic but has a high activation energy in the gas phase (~62 kcal/mol). The condensed

phases (solid or liquid) show markedly lower activation energies of roughly 35 kcal/mol due to unique

bimolecular decomposition routes at elevated densities.[14] Because of the production of carbon, TNT

explosions have a sooty appearance. Because TNT has an excess of carbon, explosive mixtures with

oxygen-rich compounds can yield more energy per kilogram than TNT alone. During the 20th century,

amatol, a mixture of TNT with ammonium nitrate was a widely used military explosive.

Detonation of TNT can be done using a high velocity initiator or by efficient concussion.[15]

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For many years, TNT used to be the reference point for the Figure of Insensitivity. TNT had a rating of

exactly 100 on the F of I scale. The reference has since been changed to a more sensitive explosive called

RDX, which has an F of I of 80.

Energy content

See also: TNT equivalent

Cross-sectional view of Oerlikon 20 mm cannon shells (dating from circa 1945) showing color codes for

TNT and pentolite fillings

Pentolite is a high explosive used for military and civilian purposes e.g. warheads and booster charges. TNT

is reported to contain 2.8 mega joules per kilogram explosive energy.[16] The actual heat of combustion is

14.5 megajoules per kilogram, which requires that some of the carbon in TNT react with atmospheric

oxygen, which does not occur in the initial event.[16] The explosive energy utilized by NIST is 4184 J/g

(4.184 MJ/kg).[17] The energy density of TNT is used as a reference-point for many other types of

explosives, including nuclear weapons, the energy content of which is measured in kilotons (~4.184

terajoules) or megatons (~4.184 peta joules) of TNT equivalent.

For comparison, gunpowder contains 3 megajoules per kilogram, dynamite contains 7.5 megajoules per

kilogram, and gasoline contains 47.2 megajoules per kilogram (though gasoline requires an oxidant, so an

optimized gasoline and O2 mixture contains 10.4 megajoules per kilogram).

Detection

Various methods can be used to detect TNT including optical and electrochemical sensors and explosive-

sniffing dogs.

In 2013, researchers from the Indian Institutes of Technology using noble-metal quantum clusters could

detect TNT at the sub-zeptomolar (1018 mol/m3) level.[18]

Safety and toxicity

TNT is poisonous, and skin contact can cause skin irritation, causing the skin to turn a bright yellow-orange

color. During the First World War, 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."

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.[19] TNT is listed as a possible human carcinogen, with carcinogenic effects demonstrated in animal

experiments (rat), although effects upon humans so far amount to none [according to IRIS of March 15,

2000]. [20] Consumption of TNT produces red urine through the presence of breakdown products and not

blood as sometimes believed.[21]

Some military testing grounds are contaminated with TNT. Wastewater from munitions programs including

contamination of surface and subsurface waters may be colored pink because of the presence of TNT. Such

contamination, called "pink water", may be difficult and expensive to remedy.

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TNT is prone to exudation of dinitrotoluenes and other isomers of trinitrotoluene. Even small quantities of

such impurities can cause such effect. The effect shows especially in projectiles containing TNT and stored

at higher temperatures, e.g. during summer. Exudation of impurities leads to formation of pores and cracks

(which in turn cause increased shock sensitivity). Migration of the exudated liquid into the fuze screw thread

can form fire channels, increasing the risk of accidental detonations; fuze malfunction can result from the

liquids migrating into its mechanism.[22] Calcium silicate is mixed with TNT to mitigate the tendency

towards exudation.[23]

Ecological impact

Because of its use in construction and demolition, TNT has become the most widely used explosive, and

thus its toxicity is the most characterized and reported. Residual TNT post explosion can partition between

multiple environmental including water, soil, atmosphere, biosphere.

The concentration of TNT in contaminated soil can reach 50 g/kg of soil, where the highest concentrations

can be found on or near the surface. In the last decade, the United States Environmental Protection Agency

(USEPA) has declared TNT a pollutant whose removal is priority.[24] The USEPA maintains that TNT levels

in soil should not exceed 17.2 gram per kilogram of soil and 0.01 milligrams per liter of water.[25]

Aqueous solubility

Dissolution involves how rapidly solid TNT in contact with water is solubilized. The relatively low aqueous

solubility of TNT causes the dissolution of solid particles to be continuously released to the environment

over extended periods of time.[26] Studies have shown that the TNT dissolved slower in saline water than in

freshwater. However, when salinity was altered, TNT dissolved at the same speed.[27] (Figure 2) Because

TNT is moderately soluble in water, it can migrate through subsurface soil, and cause groundwater

contamination.[28]

Soil adsorption

Adsorption measures the distribution between soluble and sediment sorbed contaminants following

attainment of equilibrium. Explosives such as TNT and its transformation products are known to adsorb to

surface soils and sediments, where they undergo reactive transformation or remained stored.[29] The

movement or organic contaminants through soils is a function of their ability to associate with the mobile

phase (water) and a stationary phase (soil). Materials that associate strongly with soils move slowly through

soil. Materials that associate strongly with water move through water with rates approaching that of ground

water movement.

The association constant for TNT with a soil is: 2.7-11 liters per kilogram of soil.[30] This means that TNT

has 1-10-fold tendency to adhere to a soil particulates than not when introduced into the soil.[26] Hydrogen

bonding and ion exchange are two suggested mechanisms of sorption between the nitro functional groups

and soil colloids.

The number of functional groups on TNT influences the ability to adsorb into soil. Adsorption coefficient

values have been shown to increase with an increase in the number of amino groups. Thus, sorption of the

TNT decomposition product 2,4-diamino-6-nitrotoluene (2,4-DANT) was greater than that for 4-amino-2,6-

dinitrotoluene (4-ADNT), which was greater than that for TNT.[26] Lower adsorption coefficients for 2,6-

DNT compared to 2,4-DNT can be attributed to the steric hindrance of the NO3 group in the ortho position.

Research has shown that in freshwater environments, with a high abundances of Ca2+, the sorption of TNT

and its transformation products to soils and sediments may be lower than observed in a saline environment,

dominated by K+ and Na+. Therefore, when considering the adsorption of TNT, the type of soil or sediment

and the ionic composition and strength of the ground water are important factors.[31]

http://en.wikipedia.org/wiki/Exudationhttp://en.wikipedia.org/wiki/Dinitrotoluenehttp://en.wikipedia.org/wiki/Shell_%28projectile%29http://en.wikipedia.org/wiki/Fuzehttp://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-22http://en.wikipedia.org/wiki/Calcium_silicatehttp://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-23http://en.wikipedia.org/wiki/Atmospherehttp://en.wikipedia.org/wiki/Biospherehttp://en.wikipedia.org/wiki/United_States_Environmental_Protection_Agencyhttp://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Esteve-Nunez_2001-24http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Ayoub_2010-25http://en.wikipedia.org/wiki/Dissolution_%28chemistry%29http://en.wikipedia.org/wiki/Solubilityhttp://en.wikipedia.org/wiki/Solubilityhttp://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pichtel_2012-26http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-pmid15757688-27http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-pmid12187997-28http://en.wikipedia.org/wiki/Adsorptionhttp://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-pmid19329139-29http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Haderlein_1996-30http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pichtel_2012-26http://en.wikipedia.org/wiki/Hydrogen_bondinghttp://en.wikipedia.org/wiki/Hydrogen_bondinghttp://en.wikipedia.org/wiki/Ion_exchangehttp://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pichtel_2012-26http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pennington_2002-31

The association constants for TNT and its degradation products with clays have been determined. Clay

minerals have a significant effect on the sorption of energetic compounds. and can be ranked, as seen in

Table 2. It should be noted that soil properties, such as organic carbon content and cation exchange capacity

had significant impacts of the adsorption coefficients reported in the table below.

Additional studies have shown that the mobility of TNT degradation products is likely to be lower than

TNT in subsurface environments where specific adsorption to clay minerals dominates the sorption

process.[31] Thus, the mobility of TNT and its transformation products are dependent on the characteristics

of the sorbent.[31] The mobility of TNT in groundwater and soil has been extrapolated from sorption and

desorption isotherm models determined with humic acids, in aquifer sediments, and soils.[31] From these

models, it is predicted that TNT has a low retention and transports readily in the environment.[24]

Compared to other explosives, TNT has a higher association constant with soil, meaning it adheres more

with soil than with water. Conversely, other explosives, such as RDX and HMX with low association

constants (ranging from 0.06-7.3 L/kg and 0-1.6 L/kg respectively) can move more rapidly in water.[26]

Chemical breakdown

TNT is a reactive molecule and is particularly prone to react with reduced components of sediments or

photodegradation in the presence of sunlight. TNT is thermodynamically and kinetically capable of reacting

with a wide number of components of many environmental systems. This includes wholly abiotic reactants,

like photons, hydrogen sulfide, Fe2+, or microbial communities, both oxic and anoxic.

Soils with high clay contents or small particle sizes and high total organic carbon content have been shown

to promote TNT transformation. Possible TNT transformations include reduction of one, two, or three nitro-

moieties to amines and coupling of amino transformation products to form dimers. Formation of the two

monoamino transformation products, 2-ADNT and 4-ADNT are energetically favored, and therefore are

observed in contaminated soils and ground water. The diamino products are energetically less favorable, and

even less likely are the triamino products.

The transformation of TNT is significantly enhanced under anaerobic conditions as well as under highly

reducing conditions. TNT transformations in soils can occur both biologically and abiotically.[31]

Photolysis is a major process that impacts the transformation of energetic compounds. The alteration of a

molecule in photolysis occurs in the presence of direct absorption of light energy by the transfer of energy

from a photosensitized compound. Phototransformation of TNT results in the formation of nitrobenzenes,

benzaldehydes, azodicarboxylic acids, and nitrophenols, as a result of the oxidation of methyl groups,

reduction of nitro groups, and dimer formation.[26]

Evidence of the photolysis of TNT has been seen due to the color change to pink of the wastewaters when

exposed to sunlight. Photolysis was more rapid in river water than in distilled water. Ultimately, photolysis

affects the fate of TNT primarily in the aquatic environment but could also affect the reaction when exposed

to sunlight on the soil surface.[31]

Biodegradation

The ligninolytic physiological phase and manganese peroxidase system of fungi can cause a very limited

amount of mineralization of TNT in a liquid culture; though not in soil. An organism capable of the

remediation of large amounts of TNT in soil has yet to be discovered.[32] Both wild and transgenic plants can

phytoremediate explosives from soil and water.[33]

http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pennington_2002-31http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pennington_2002-31http://en.wikipedia.org/wiki/Isothermal_processhttp://en.wikipedia.org/wiki/Humic_acidshttp://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pennington_2002-31http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Esteve-Nunez_2001-24http://en.wikipedia.org/wiki/RDXhttp://en.wikipedia.org/wiki/HMXhttp://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pichtel_2012-26http://en.wikipedia.org/wiki/Photodegradationhttp://en.wikipedia.org/wiki/Photonshttp://en.wikipedia.org/wiki/Hydrogen_sulfidehttp://en.wikipedia.org/wiki/Ferroushttp://en.wikipedia.org/wiki/Total_organic_carbonhttp://en.wikipedia.org/wiki/Reduction_reactionhttp://en.wikipedia.org/wiki/Dimer_%28chemistry%29http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pennington_2002-31http://en.wikipedia.org/wiki/Photolysishttp://en.wikipedia.org/wiki/Nitrobenzenehttp://en.wikipedia.org/wiki/Benzaldehydehttp://en.wikipedia.org/wiki/Nitrophenolhttp://en.wikipedia.org/wiki/Oxidationhttp://en.wikipedia.org/wiki/Methyl_grouphttp://en.wikipedia.org/wiki/Nitro_compoundhttp://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pichtel_2012-26http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-Pennington_2002-31http://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-pmid11131384-32http://en.wikipedia.org/wiki/Phytoremediationhttp://en.wikipedia.org/wiki/Trinitrotoluene#cite_note-pmid22996005-33