Chemical Properties
Nitrotoluene is formed in 3 isomeric forms.
The o-and m-forms are yellow liquids or solids. The p-form
is a pale yellow crystalline solid. All have weak aromatic
odors. The Odor Thresholds are: 0.05 mg/L (o-isomer);
1.74 ppm (m-isomer).
Physical properties
3-Nitrotoluene is a light yellow oily liquid with a nitrobenzene-like odor. The relative density is 1.1571, the melting point is 16°C, and the boiling point is 230-231°C. Almost insoluble in water, soluble in ethanol, ether, chloroform and benzene. Can volatilize with water vapor.
Uses
3-Nitrotoluene is mainly used in organic synthesis as an intermediate for pesticides, dyes, explosives, medicines, color developers, plastics, synthetic fibers and auxiliaries.
Preparation
3-Nitrotoluene is obtained by fractional distillation and purification after nitration of toluene with mixed acid below 50℃. Toluene nitration can get different products with different reaction conditions and catalysts, such as o-nitrotoluene, p-nitrotoluene, m-nitrotoluene, 2,4-dinitrotoluene and 2,4,6-trinitrotoluene Toluene etc.
Definition
ChEBI: 3-nitrotoluene is a mononitrotoluene carrying a nitro group at position 3.
Application
Catalytic hydrogenation or reduction with iron converts 3-nitrotoluene to m-toluidine, which provides important coupling components for azo dyes, usually after N-alkylation.
General Description
Yellow crystals that melt at 59°F to a yellow liquid. Often therefore encountered as a liquid. Flash point 223°F. Boiling point 450°F. Insoluble in water. Toxic by inhalation and ingestion.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
3-Nitrotoluene reacts with sulfuric acid, strong oxidizing agents and reducing agents.
Hazard
Toxic by inhalation, ingestion, skin absorption. Methemoglobinemia. Probable carcinogen.
Health Hazard
INHALATION, INGESTION OR SKIN ABSORPTION: Headache, flushing of face, dizziness, difficult breathing, cyanosis, nausea, vomiting, muscular weakness, increased pulse and respiratory rate, irritability and convulsions. EYES: Slight irrita- tion. SKIN: Slight irritation.
Potential Exposure
The nitrotoluenes are used in the
production of toluidines and other dye intermediates.
All isomers are used in manufacture of agriculture and
rubber chemicals and in various dyes.
Environmental Fate
Biological. Under anaerobic conditions using a sewage inoculum, 3-nitrotoluene and 4-
nitrotoluene both degraded to toluidine (Hallas and Alexander, 1983). Robertson et al. (1992)
reported that toluene dioxygenases from Pseudomonas putida F1 and Pseudomonas sp. Strain JS
150 oxidized the methyl group forming 3-nitrobenzyl alcohol.
Shipping
UN1664 Nitrotoluenes, (o-; m-; p-), Hazard
Class: 6.1; Labels: 6.1-Poisonous materials.
Purification Methods
Dry 3-nitrotoluene over P2O5 for 24hours, then fractionally distil it under reduced pressure. [Clark & Taylor Org. Synth Coll Vol I 415 1941, Beilstein 5 IV 847.]
Incompatibilities
Decomposes on contact with strong oxidizers;
strong acids; reducing agents; strong bases; ammonia,
amines producing toxic fumes, causing fire and explosion
hazard. Heat above 190C may cause explosive decomposition.
Attacks some plastics, rubbers, and coatings.
Waste Disposal
Controlled incineration-care
must be taken to maintain complete combustion at all
times. Incineration of large quantities may require scrubbers
to control the emission of nitrogen oxides.
