Nitrobenzene

Chemical structure of nitrobenzene
Chemical structure of nitrobenzene

Nitrobenzene, also known as nitrobenzol or oil of mirbane, is a poisonous organic compound with an almond odor and chemical formula C6H5NO2. It may be found as either bright yellow crystals or an oily insoluble liquid.

It is used as a solvent and as a mild oxidizing agent. It is most frequently used specifically in the manufacture of aniline, but also used in the manufacture of insulating compounds and polishes.

Contents

Characteristics

Nitrobenzene
Characteristic/Property Data Reference
CAS No. 98-95-3
Common Synonyms nitrobenzol; oil of mirbane U.S. EPA 1994
Molecular Formula C6H5NO2
Physical State liquid U.S. EPA 1985
Molecular Weight 123.06 g/mol U.S. EPA 1985
Melting Point 5.85 C @ 1 atm U.S. EPA 1985
Boiling Point 210.9 C @ 1 atm U.S. EPA 1985
Water Solubility 1.9 g/L @ 20 C;
2.1 g/L @ 25 C
U.S. EPA 1985
Density 1.199 kg/L @ 24 C U.S. EPA 1985
Vapor Density (air = 1) 4.1 U.S. EPA 1985
Carbon matter partition coefficient Koc 36-650 (estimated) U.S. EPA 1987
log (octanol-water partition coefficient)
log Kow
1.85 U.S. EPA 1987
Vapor pressure (20 C) 20 Pa (0.15 mmHg) U.S. EPA 1987
Vapor pressure (25 C) 36 Pa (0.27 mmHg) U.S. EPA 1987
Reactivity flammable
Flash point 88 C (closed cup) Budavari 1989
Henry's Law constant (25 C) 2.33 J/mol
2.3×10-5 atmm³/mol
U.S. EPA 1985
Fish bioconcentration factor <10-15 (measured in the golden orfe) U.S. EPA 1985
Odor threshold perception, 18.2 g/m (3.55 nmol/mol) Verschueren 1983
threshold, 9.7 mg/m (1.9 mol/mol) U.S. EPA 1985
Conversion factors (in air)
1 ppm by molecules = 1 mol/mol
1 mol/mol = 5.12 mg/m³
1 mg/m = 0.195 mol/mol
Verschueren 1983

Uses

While nitrobenzene is primarily used in the production of aniline and aniline derivatives, such as methyl diphenyl diisocyanate (MDI), it also finds use in the manufacture of 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. Substitution reactions with nitrobenzene are used to form m-derivatives (Mannsville 1991; Sittig 1991). 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 acetaminophen (Mannsville 1991).

Production

There were four producers of nitrobenzene in the United States in 1991: First Chemicals Corporation, Mobay, DuPont Chemicals, and Rubicon Inc. In 1991, the estimated total production capacity of nitrobenzene in the U.S. was 1,360 million pounds (617 gigagrams) (Mannsville 1991).

External links

it:Nitrobenzene

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