Nitrobenzene

Nitrobenzene is an organic compound with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents. Nitrobenzene is prepared by nitration of benzene with a mixture of concentrated sulfuric acid, water, and nitric acid. This mixture is sometimes called "mixed acid." The production of nitrobenzene is one of the most dangerous processes conducted in the chemical industry because of the exothermicity of the reaction (ΔH = −117 kJ/mol). World capacity for nitrobenzene in 1985 was about 1,700,000 tonnes. The nitration process involves formation of the nitronium ion (NO2+), followed by an electrophilic aromatic substitution reaction of it with benzene. The nitronium ion is generated by the reaction of nitric acid and an acidic dehydration agent, typically sulfuric acid: HNO3 + H+ NO2+ + H2O Approximately 95% of nitrobenzene industrially produced is hydrogenated to aniline: C6H5NO2 + 3 H2 → C6H5NH2 + 2 H2O Aniline is a precursor to urethane polymers, rubber chemicals, pesticides, dyes (particularly azo dyes), explosives, and pharmaceuticals. Nitrobenzene is also used to mask unpleasant odors in shoe and floor polishes, leather dressings, paint solvents, and other materials. Redistilled, as oil of mirbane, nitrobenzene had been used as an inexpensive perfume for soaps. It has been replaced by less toxic chemicals for this purpose. A significant merchant market for nitrobenzene is its use in the production of the analgesic paracetamol (also known as acetaminophen) (Mannsville 1991). Nitrobenzene is also used in Kerr cells, as it has an unusually large Kerr constant. Evidence suggests its use in agriculture as a plant growth/flowering stimulant. Aside from its conversion to aniline, nitrobenzene can be selectively reduced to azoxybenzene, azobenzene, nitrosobenzene, hydrazobenzene, and phenylhydroxylamine.