2,4-Dinitrotoluene

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2,4-Dinitrotoluene
IUPAC name

1-methyl-2,4-dinitro benzene

Identifiers
CAS number 121-14-2 YesY
PubChem 8461
ChemSpider 8150 YesY
UN number Molten: 1600
Solid or liquid: 2038
KEGG C11006 YesY
ChEBI CHEBI:920 YesY
ChEMBL CHEMBL259865 YesY
Jmol-3D images {{#if:Cc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-]|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
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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.

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[citation needed] and toxic, modern formulations tend to avoid its use. In this application it is often used together with dibutyl phthalate.[citation needed]

Toxicity

Dinitrotoluenes are highly toxic with a threshold limit value (TLV) of 1.5 mg/m3.[4] 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 Record of 2,4-Dinitrotoluene in the GESTIS Substance Database from the IFA, accessed on 9. October 2007
  2. ↑ Booth, G. (2005), "Nitro Compounds, Aromatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a17_411 
  3. ↑ Six, C.; Richter, F. (2005), "Isocyanates, Organic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a14_611 
  4. ↑ NIOSH Pocket Guide to Chemical Hazards - Dinitroluene
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