| | 2,4-Dinitrotoluene Basic information |
| | 2,4-Dinitrotoluene Chemical Properties |
| Melting point | 67-70 °C(lit.) | | Boiling point | 300 °C | | density | 1,521 g/cm3 | | vapor pressure | 1 mm Hg ( 102.7 °C) | | refractive index | 1.4420 | | Fp | 155 °C | | storage temp. | 2-8°C | | solubility | Soluble in acetone, ethanol, benzene, ether, and pyrimidine (Weast, 1986) | | pka | 13.53 (Perrin, 1972) | | form | neat | | Water Solubility | 0.3 g/L (20 ºC) | | BRN | 1912834 | | Henry's Law Constant | 5.39(x 10-8 atm?m3/mol) at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) | | Stability: | Stable. Incompatible with oxidizing agents, reducing agents, strong bases. | | InChIKey | RMBFBMJGBANMMK-UHFFFAOYSA-N | | CAS DataBase Reference | 121-14-2(CAS DataBase Reference) | | IARC | 2B (Vol. 65) 1996 | | NIST Chemistry Reference | Benzene, 1-methyl-2,4-dinitro-(121-14-2) | | EPA Substance Registry System | 2,4-Dinitrotoluene (121-14-2) |
| | 2,4-Dinitrotoluene Usage And Synthesis |
| Description | 2,4-Dinitrotoluene is the most common of the six dinitrotoluene isomers. Dinitrotoluene (DNT) or Dinitro is an explosive with the formula C6H3(CH3)(NO2)2. At room temperature it is a pale yellow to orange crystalline solid. It is a high explosive and one of the precursors for trinitrotoluene (TNT), which is synthesized through three separate nitrations of toluene. The first product is mononitrotoluene, DNT is the second, and TNT is the third and final product. Dinitrotoluene induced sensitization in an employee of a manufacturers of explosives, also sensitized to nitroglycerin. | | Chemical Properties | 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. | | Physical properties | Both 2,4-Dinitrotoulene (2,4-DNT) and 2,6-Dinitrotoluene (2,6-DNT) are man-made solids that are pale yellow and have a slight odor. They are two of the six forms of a chemical called Dinitrotoluene (DNT). DNT is made by mixing toluene with nitric acid. | | Uses | 2,4-Dinitrotoluene is used largely, along with the 2,6-isomer,
to make toluene diisocyanate. The DNT mixture is hydrogenated
to yield the diamine that is reacted with phosgene to
form the diisocyanate that is reacted with polyols to make
polyurethane foams. DNT is also employed to some
extent in manufacturing explosives. | | Uses | A metabolite of TNT (2,4,6-trinitrotoluene). The metabolites of TNT | | Definition | ChEBI: 2,4-dinitrotoluene is a dinitrotoluene in which the methyl group is ortho to one of the nitro groups and para to the other. It is the most common isomer of dinitrotoluene. | | General Description | Heated yellow liquid. Solidifies if allowed to cool. Insoluble in water and more dense than water. Toxic by skin absorption, inhalation and ingestion. Easily absorbed through the skin. Produces toxic oxides of nitrogen during combustion. Used to make dyes and other chemicals. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | DINITROTOLUENE is incompatible with strong oxidizing agents, caustics, active metals, tin and zinc . Decomposition occurs at 250°C. Prolonged heating below 250°C causes some decomposition, and the presence of impurities may decrease the decomposition temperatures. Decomposition is self-sustaining at 280°C. Containers may explode in a fire [USCG, 1999]. May react violently in the presence of a base or when heated to the boiling point. Attacks some forms of plastics, rubbers and coatings . | | Health Hazard | Ingestion or overexposure to vapors from hot liquid can cause loss of color, nausea, headache, dizziness, drowsiness, collapse. Hot liquid can burn eyes and skin. Prolonged skin contact with solid can give same symptoms as after inhalation or ingestion. | | Safety Profile | 2,4-Dintirotoluene is used as an intermediate in the manufacture of polyurethanes. No information is available on the acute (short-term) effects of 2,4-dinitrotoluene in humans. Chronic (long-term) inhalation exposure to 2,4-dinitrotoluene affects the central nervous system (CNS) and blood in humans. A significant reduction in sperm count and normal sperm morphology was observed in one study of chronically exposed workers, while other studies have not reported this effect. No significant increase in cancer mortality was observed in a study of workers occupationally exposed to 2,4-dinitrotoluene by inhalation. Kidney, liver, and mammary gland tumors were observed in animals orally exposed to 2,4- dinitrotoluene. EPA has not classified 2,4-dinitrotoluene for potential carcinogenicity. | | Environmental fate | Biological. When 2,4-dinitrotoluene was statically incubated in the dark at 25 °C with yeast
extract and settled domestic wastewater inoculum, significant biodegradation with gradual
acclimation was followed by deadaptive process in subsequent subcultures. At a concentration of 5
mg/L, 77, 61, 50, and 27% losses were observed after 7, 14, 21, and 28-d incubation periods,
respectively. At a concentration of 10 mg/L, only 50, 49, 44, and 23% were observed after 7, 14,
21, and 28-d incubation periods, respectively (Tabak et al., 1981).
Photolytic. Low et al. (1991) reported that nitro-containing compounds (e.g., 2,4-dinitrophenol)
degrade via UV light in the presence of titanium dioxide yielding ammonium, carbonate, and
nitrate ions. By analogy, 2,4-dinitrotoluene should degrade forming identical ions.
Chemical/Physical. Wet oxidation of 2,4-dinitrotoluene at 320 °C yielded formic and acetic
acids (Randall and Knopp, 1980). | | Metabolic pathway | The major biliary metabolite of 2,4-dinitrotoluene (2,4-
DNT) in the rat is the glucuronide conjugate of 2,4-
dinitrobenzyl alcohol and the minor metabolites are
2,4-dinitrobenzyl alcohol, 2,4-dinitrobenzaldehyde, 2-
acetylamino-4-nitrotoluene, 4-amino-2-nitro or 2-
amino-4-nitrobenzyl alcohol sulfate, 2,4-dinitrobenzoic
acid, 2,4-diacetylaminobenzoic acid, and 2-amino-4-
nitrobenzoic acid. | | Purification Methods | Crystallise it from Me2CO, isopropanol or MeOH. Dry it in a vacuum over H2SO4. It has also been purified by zone melting. It could be EXPLOSIVE when dry.[Beilstein 5 H339, 5 IV 865, 5 III 759.] |
| | 2,4-Dinitrotoluene Preparation Products And Raw materials |
| Raw materials | Toluene-->Nitric acid-->Water-->4-Nitrotoluene-->2-Nitrotoluene-->3-Nitrotoluene-->1-BROMO-2,4-DINITROBENZENE-->2,4-DINITROBENZYL BROMIDE-->2,4-Dinitrofluorobenzene-->2,4-Dinitrochlorobenzene-->3,5-dinitrotoluene-->2,5-DINITROTOLUENE-->2,3-DINITROTOLUENE-->3,4-DINITROTOLUENE | | Preparation Products | 2,4-Diaminotoluene-->2,4-Dinitrobenzaldehyde-->2,6-Dinitrotoluene-->2,4-DINITROBENZOIC ACID-->2-Methyl-5-nitrophenol-->toluene-3,5-diamine-->C.I. Sulphur Brown 62 (8CI)-->Benzene, 1-methyl-2,4-dinitro-, sulfurized-->[1,1'-Biphenyl]-4,4'-diamine, reaction products with 1-methyl-2,4-dinitrobenzene and sodium sulfide (Na2(Sx))-->Leuco Sulphur Brown 46 |
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