2,4-Dinitrotoluene

2,4-Dinitrotoluene
IUPAC name

1-methyl-2,4-dinitro benzene
Identifiers
CAS number 121-14-2 Y
PubChem 8461
ChemSpider 8150 Y
UN number raztopljen: 1600
tekoč ali trden: 2038
KEGG C11006 Y
ChEBI CHEBI:920 Y
ChEMBL CHEMBL259865 Y
Jmol-3D images Image 1
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
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

Contents

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.

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. ^ a b c Record of 2,4-Dinitrotoluene in the GESTIS Substance Database from the IFA, accessed on 9. October 2007
  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