Everything about Nitrobenzene totally explained
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Nitrobenzene, also known as
nitrobenzol or
oil of mirbane, is an
organic compound with the
chemical formula C6H5NO2. This oily water-insoluble liquid, which is quite toxic, is mainly produced as a precursor to
aniline. In the laboratory it finds occasional use as a
solvent, especially for electrophilic
reagents.
Uses
Approximately 95% of nitrobenzene is consumed in the production of
aniline.
Specialized applications
More specialized applications include the use of nitrobenzene as a precursor to
rubber chemicals,
pesticides,
dyes, and
pharmaceuticals. Nitrobenzene is also used in shoe and floor polishes, leather dressings, paint
solvents, and other materials to mask unpleasant odors. Redistilled, as oil of mirbane, nitrobenzene has been used as an inexpensive perfume for
soaps. 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.
Organic reactions
Aside from its conversion to aniline, nitrobenzene is readily converted to related derivatives such as
azobenzene,
nitrosobenzene, and
phenylhydroxylamine. Substitution reactions with nitrobenzene characteristically form meta-derivatives (Mannsville 1991; Sittig 1991).
Production
Nitrobenzene is prepared by
nitration of benzene with a mixture of concentrated
sulfuric acid,
water, and
nitric acid, called "mixed acid." Its production is one of the more dangerous processes conducted in the chemical industry due to the exothermicity of the reaction (ΔH = −117 kJ/mol).
[
There were four producers of nitrobenzene in the United States in 1991: First Chemicals Corporation, Mobay, DuPont Chemicals, and Rubicon Inc. World capacity for nitrobenzene in 1985 was ca. 1.7×106 tonnes.][
]Mechanism of nitration
The reaction pathway entails formation of an adduct between the Lewis acidic nitronium ion, NO2+, and benzene. The nitronium ion is generated in situ via the reaction of nitric acid and an acidic dehydration agent, typically sulfuric acid: » HNO3 + H+ ⇌ NO2+ + H2O
Safety
Nitrobenzene is highly toxic (TLV 5 mg/m3) and readily absorbed through the skin.[
]Further Information
Get more info on 'Nitrobenzene'.
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