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118-96-7

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Basic Information
CAS No.: 118-96-7
Name: 2,4,6-Trinitrotoluene
Article Data: 54
Molecular Structure:
Molecular Structure of 118-96-7 (2,4,6-Trinitrotoluene)
Formula: C7H5N3O6
Molecular Weight: 227.133
Synonyms: Toluene,2,4,6-trinitro- (7CI,8CI);1-Methyl-2,4,6-trinitrobenzene;2-Methyl-1,3,5-trinitrobenzene;4-Methyl-1,3,5-trinitrobenzene;Gradetol;NSC 36949;TNT;Trinitrotoluene;Tritol(explosive);Trotyl;Trotyl oil;sym-Trinitrotoluene;sym-Trinitrotoluol;a-TNT;
EINECS: 204-289-6
Density: 1.608 g/cm3
Melting Point: 80.9 °C
Boiling Point: 339.227 °C at 760 mmHg
Flash Point: 167.109 °C
Appearance: yellow crystals
Hazard Symbols: ExplosiveE, ToxicT, DangerousN, HarmfulXn, FlammableF, ExplosiveB
Risk Codes: 2-23/24/25-33-51/53-36-20/21/22-11-1
Safety: 35-45-61-36/37-26
Transport Information: UN 0209
PSA: 137.46000
LogP: 3.28920
Synthetic route
99-99-0

1-methyl-4-nitrobenzene

118-96-7

2,4,6-Trinitrotoluene

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 110℃; for 4h; Temperature;92.2%
With sulfuric acid; nitric acid at 20 - 100℃; Nitration;89%
With sulfuric acid; nitric acid 1.) 0 deg C, 10 min, 2.) 95 deg C, 6 h, then room temp., 12 h;69%
88-72-2

1-methyl-2-nitrobenzene

118-96-7

2,4,6-Trinitrotoluene

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 110℃; for 4h;92.2%
With sulfuric acid; nitric acid
durch Nitrierung;
108-88-3

toluene

118-96-7

2,4,6-Trinitrotoluene

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 20 - 90℃; Nitration;84%
With nitric acid; Petroleum ether azeotropes Abdestillieren des gebildeten Wassers;
With sulfuric acid; nitric acid
121-14-2

2,4-dinitrotoluene

118-96-7

2,4,6-Trinitrotoluene

Conditions
ConditionsYield
With sulfuric acid; nitric acid 1.) 90-100 deg C, 2 h, 2.) 25 deg C, overnight;62%
Nitrierung;
durch Nitrierung;
99-35-4

1,3,5-trinitrobenzene

118-96-7

2,4,6-Trinitrotoluene

Conditions
ConditionsYield
With lead(IV) acetate; acetic acid
99-87-6

4-methylisopropylbenzene

118-96-7

2,4,6-Trinitrotoluene

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 60 - 70℃;
606-20-2

2,6-dinitrotoluene

118-96-7

2,4,6-Trinitrotoluene

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 93 - 103℃;
With ammonium nitrate In sulfuric acid at 0 - 25℃;
77601-83-3

2,4,6-trinitrophenylacetic acid

118-96-7

2,4,6-Trinitrotoluene

Conditions
ConditionsYield
With water
With ethanol
99-65-0

meta-dinitrobenzene

546-67-8

lead(IV) tetraacetate

64-19-7

acetic acid

A

118-96-7

2,4,6-Trinitrotoluene

B

632-92-8

2,4-dimethyl-1,3,5-trinitrobenzene

Conditions
ConditionsYield
Erwaermen des Reaktionsprodukts mit rauchender Salpetersaeure und konz. H2SO4 auf 75-120grad;
99-35-4

1,3,5-trinitrobenzene

546-67-8

lead(IV) tetraacetate

64-19-7

acetic acid

A

118-96-7

2,4,6-Trinitrotoluene

B

632-92-8

2,4-dimethyl-1,3,5-trinitrobenzene

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Chemistry

Molecular formula: C7H5N3O6
Molar mass: 227.13 g/mol
Appearance: Pale yellow. Loose "needles" before melt-casting. A solid block after being poured into a casing.
Density: 1.654 g/cm3
Melting point: 80.35 °C
Boiling point: 295 °C (decomposition)
Solubility in water: 0.13 g/L (20 °C)
Solubility in ether, acetone, benzene, pyridine: soluble
Other names:1,3,5-trinitrotoluene, sym-trinitrotoluene, TNT.
The Structure of 2,4,6-trinitrotoluene(118-96-7):

History

2,4,6-trinitrotoluene(118-96-7) was first prepared in 1863 by German 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 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. The British started replacing lyddite with TNT in 1907. TNT is still widely used by the United States military and 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.

Uses

2,4,6-trinitrotoluene(118-96-7) is one of the most commonly used explosives for military and industrial applications.

Production

Symmetrical trinitrotoluene (118-96-7) is manufactured by multiple-stage nitration of toluene with a mixture of nitric acid and sulfuric acid.
 Three-stage nitration to mono-, di-, and trinitrotoluene was formerly used, but continuous-flow stirred-tank reactors and tubular units using the countercurrent flow of strong acids and toluene permit better yields and reaction control.

Toxicity Data With Reference

1.   

skn-rbt 500 mg/24H MLD

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD-B011-150 .
2.   

mmo-sat 10 µg/plate

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD-A080-146 .
3.   

orl-hmn LDLo:28 g/kg:CNS,PUL,GIT

   34ZIAG    Toxicology of Drugs and Chemicals ,Deichmann, W.B.,New York, NY.: Academic Press, Inc.,1969,610.
4.   

orl-rat LD50:795 mg/kg

   JTEHD6    Journal of Toxicology and Environmental Health. 9 (1982),565.
5.   

orl-mus LD50:660 mg/kg

   JTEHD6    Journal of Toxicology and Environmental Health. 9 (1982),565.
6.   

orl-cat LDLo:1850 mg/kg

   MRCSAB    Medical Research Council, Special Report Series. 58 (1921),32.
7.   

scu-cat LDLo:200 mg/kg

   MRCSAB    Medical Research Council, Special Report Series. 58 (1921),32.
8.   

orl-rbt LDLo:500 mg/kg

   MRCSAB    Medical Research Council, Special Report Series. 58 (1921),32.
9.   

scu-rbt LDLo:500 mg/kg

   MRCSAB    Medical Research Council, Special Report Series. 58 (1921),32.

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Safety Profile

Suspected carcinogen. Poison by subcutaneous route. Moderately toxic by ingestion. Human systemic effects by ingestion: hallucinations or distorted perceptions, cyanosis, and gastrointestinal changes. Experimental reproductive effects. Mutation data reported. A skin irritant. Has been implicated in aplastic anemia. Can cause headache, weakness, anemia, liver injury. May be absorbed through skin.

Flammable or explosive when exposed to heat or flame. Moderate explosion hazard; will detonate under strong shock. It detonates at around 240°C but can be distilled safely under reduced pressure. It is a comparatively insensitive explosive. In small quantities it will burn quietly if not confined. However, sudden heating of any quantity will cause it to detonate; the accumulation of heat when large quantities are burning will cause detonation. In other respects it is one of the most stable of all high explosives, and there are but a few restrictions for its handling. It is for this reason, from the military standpoint, that TNT is quantitatively the most used. It requires a fall of 130 cm for a 2 kg weight to detonate it. It is one of the most powerful high explosives. It can be detonated by the usual detonators and blasting caps (at least a No. 6). For full efficiency, the use of a high-velocity initiator, such as tetryl, is required. TNT is one of those explosives containing an oxygen deficiency. In other words, the addition of products that are oxygen rich can enhance its explosive power. Also mono- and dinitrotoluene may be added for reduction of the temperature of the explosion and to make the explosion flashless. Various materials are added to TNT to make what are known as permissible explosives. TNT may be regarded as the equivalent of 40% dynamite and can be used underwater. It is also used in the manufacture of a detonator fuse known as cordeau detonant. For the military, TNT finds use in all types of bursting charges, including armor-piercing types, although it is somewhat too sensitive to be ideal for this purpose and has since been replaced to a great extent by ammonium picrate. It is a relatively expensive explosive and does not compete seriously with dynamite for general commercial use.

Highly dangerous; explodes with shock or heating to 297°C. Various materials can reduce the explosive temperature: red lead (to 192°C), sodium carbonate (to 218°C), potassium hydroxide (to 192°C). Mixtures with sodium dichromate + sulfuric acid may ignite spontaneously. Reacts with nitric acid + metals (e.g., lead or iron) to form explosive products more sensitive to shock, friction, or contact with nitric or sulfuric acids. Reacts with potassium hydroxide dissolved in methanol to form explosive aci-nitro salts. Bases (e.g., sodium hydroxide, potassium iodide, tetramethyl ammonium octahydrotriborate) induce deflagration in molten TNT. Can react vigorously with reducing materials. When heated to decomposition it emits highly toxic fumes of NOx. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS and EXPLOSIVES, HIGH.

Standards and Recommendations

OSHA PEL: TWA 0.5 mg/m3 (skin)
ACGIH TLV: TWA 0.1 ppm
DFG MAK: 0.011 ppm (0.1 mg/m3); Confirmed Animal Carcinogen with Unknown Relevance to Humans
DOT Classification:  EXPLOSIVE 1.1D; Label: EXPLOSIVE 1.1D (UN 0209); DOT Class: 4.1; Label: Flammable Solid (UN 1356)

Analytical Methods

For occupational chemical analysis use OSHA: #44.