2,4-Dinitrotoluene

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2,4-Dinitrotoluene
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IUPAC name 1-methyl-2,4-dinitro benzene
Identifiers
CAS number 121-14-2
PubChem 8461
KEGG C11006
ChEBI 920
SMILES Cc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-]
InChI InChI=1/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3
Properties
Molecular formula C7H6N2O4
Molar mass 182.13 g mol-1
Appearance Pale yellow to orange crystalline solid
Density 1.52 g/cm3[1]
Melting point

70 °C[1]

Boiling point

Decomposes at 250–300 °C[1]

Explosive data
Shock sensitivity Insensitive
Friction sensitivity Very low
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

2,4-Dinitrotoluene (DNT) or Dinitro is an organic compound with the formula CH3C6H3)(NO2)2. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.

Isomers of dinitrotoluene

Six isomers are possible for dinitrotoluene. The most common one is 2,4-dinitrotoluene.

The nitration of toluene gives sequentially mononitrotoluene, DNT, and finally TNT. 2,4-DNT is the principal product from dinitration, the other main product being about 30% 2,6-DNT. The nitration of 4-nitrotoluene gives 2,4-DNT.[2]

Applications

Most DNT is used in the production of toluene diisocyanate, which is used to produce flexible polyurethane foams. DNT is hydrogenated to produce toluenediamine, which in turn is phosgenated to give toluene diisocyanate. In this way, about 1.4 billion kilograms are produced annually, as of the years 1999-2000.[3] Other uses include the explosives industry. It is not used by itself as an explosive, but some of the production is converted to TNT.

Dinitrotoluene is frequently used as a plasticizer, deterrent coating, and burn rate modifier in propellants (e.g., smokeless gunpowders). As it is carcinogenic and toxic, modern formulations tend to avoid its use. In this application it is often used together with dibutyl phthalate.Template:Citation needed

Toxicity

Dinitrotoluenes are highly toxic with a TLV of 1.5 mg/m3. It converts hemoglobin into methemoglobin.

2,4 Dinitrotoluene is also a listed hazardous waste under 40 CFR 261.30. Its United States Environmental Protection Agency (EPA) hazardous waste Number is D030. The maximum concentration that may be contained to not have toxic characteristics is 0.13 mg/L.

References

  1. 1.0 1.1 1.2 Template:GESTIS
  2. Gerald Booth (2007). "Nitro Compounds, Aromatic". In: Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York. doi:10.1002/14356007.a17_411
  3. Christian Six, Frank Richter "Isocyanates, Organic" in Ulmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH, Weinheim doi:10.1002/14356007.a14_611

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