2,4-Dinitrotoluene

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2,4-Dinitrotoluene
2,4-Dinitrotoluol.svg
2,4-Dinitrotoluene-3D-balls.png
Names
Preferred IUPAC name
1-Methyl-2,4-dinitrobenzene
Other names
Dinitrotoluol, Methyldinitrobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.046 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
UN number Molten: 1600
Solid or liquid: 2038
  • InChI=1S/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3 Yes check.svgY
    Key: RMBFBMJGBANMMK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3
    Key: RMBFBMJGBANMMK-UHFFFAOYAC
  • Cc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-]
Properties
C7H6N2O4
Molar mass 182.134 g/mol
AppearancePale yellow to orange crystalline solid
Density 1.52 g/cm3 [1]
Melting point 70 °C (158 °F; 343 K) [1]
Boiling point Decomposes at 250–300 °C [1]
Vapor pressure 1.47X10-4 mm Hg @ 22 C

[2]

Hazards
Occupational safety and health (OHS/OSH):
Main hazards
carcinogen, combustible (though difficult to ignite) [3]
Flash point 207 °C; 404 °F; 480 K
Lethal dose or concentration (LD, LC):
1,954 mg/kg (oral, mouse) [4]
27 mg/kg (cat, oral) [4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1.5 mg/m3 [skin] [3]
REL (Recommended)
Ca TWA 1.5 mg/m3 [skin] [3]
IDLH (Immediate danger)
Ca [50 mg/m3] [3]
Explosive data
Shock sensitivity Insensitive
Friction sensitivity Very low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. 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 positional 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% 1,3-DN2-T. The nitration of 4-nitrotoluene gives 2,4-DNT. [5]

Applications

Most DNT is used in the production of toluene diisocyanate, which is used to produce flexible polyurethane foams. DNT is hydrogenated to produce 2,4-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. [6] 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 [3] 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. [7] It converts hemoglobin into methemoglobin.

2,4-Dinitrotoluene is also a listed hazardous waste under 40 CFR 261.24. 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.

Related Research Articles

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<span class="mw-page-title-main">Methylene diphenyl diisocyanate</span> Aromatic diisocyanate

Methylene diphenyl diisocyanate (MDI) is an aromatic diisocyanate. Three isomers are common, varying by the positions of the isocyanate groups around the rings: 2,2′-MDI, 2,4′-MDI, and 4,4′-MDI. The 4,4′ isomer is most widely used, and is also known as 4,4′-diphenylmethane diisocyanate. This isomer is also known as Pure MDI. MDI reacts with polyols in the manufacture of polyurethane. It is the most produced diisocyanate, accounting for 61.3% of the global market in the year 2000.

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Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

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Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<i>o</i>-Xylene Chemical compound

o-Xylene (ortho-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2, with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of m-xylene and p-xylene, the mixture being called xylene or xylenes. o-Xylene is a colourless slightly oily flammable liquid.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

<i>m</i>-Xylene Chemical compound

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<span class="mw-page-title-main">Cyclohexylamine</span> Chemical compound

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<i>o</i>-Anisidine Chemical compound

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4-Nitrochlorobenzene is the organic compound with the formula ClC6H4NO2. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including antioxidants commonly found in rubber. Other isomers with the formula ClC6H4NO2 include 2-nitrochlorobenzene and 3-nitrochlorobenzene.

ortho-Cresol (IUPAC name: 2-methylphenol, also known as 2-hydroxytoluene or ortho-Toluenol) is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and m-cresol.

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2,5-Diaminotoluene is an organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. 2,5-Diaminotoluene is a colorless crystalline solid, although commercial samples are often colored owing to air oxidation. It is commonly used in hair coloring.

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

3-Nitrotoluene or meta-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is one of three isomers of nitrotoluene. A yellow liquid, it is used in the manufacture of meta-toluidine, which is an intermediate in the production of various dyes.

2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes.

<span class="mw-page-title-main">2,4-Diaminotoluene</span> Chemical compound

2,4-Diaminotoluene is an aromatic organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. It is a white solid, although commercial samples are often yellow-tan.

References

  1. 1 2 3 Record of 2,4-Dinitrotoluene in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 9. October 2007.
  2. ↑ Pella, PA. J. Chem. Thermodyn. 9: 301-305, 1977
  3. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0235". National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 "Dinitrotoluene (mixed isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). 4 December 2014. Retrieved 17 March 2015.
  5. ↑ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN   978-3527306732.
  6. ↑ Six, C.; Richter, F. "Isocyanates, Organic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a14_611. ISBN   978-3527306732.
  7. ↑ NIOSH Pocket Guide to Chemical Hazards - Dinitroluene
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