NITROBENZENE
PRODUCT IDENTIFICATION
98-95-3
123.11
H.S. CODE
CLASSIFICATION
PHYSICAL AND CHEMICAL PROPERTIES
AUTOIGNITION
NFPA RATINGS
REFRACTIVE INDEX
APPLICATIONS
Nitrobenzene (also called nitrobenzol ) is a colourless to pale yellow, oily, highly toxic liquid with the odour of bitter almonds. Nitrobenzene is manufactured commercially by nitration of benzene (also a common air pollutant) using a mixture of nitric and sulfuric acids. Commercially nitrobenzene can be either produced in a batch or by a continuous process. Both batch and continuous processes employing mixed nitric and sulfuric acids are used to make nitrobenzene. The continuous process is favored over the batch process because its production capacity is much larger, it has lower capital costs and it entails more efficient labor usage. Reactors for the continuous process also usually utilized lower nitric acid concentrations, are smaller with more rapid and efficient mixing, and therefore have higher reaction rates. Nitrobenzene undergoes nitration, halogenation, and sulfonation much more slowly than does benzene. It may be reduced to a variety of compounds, depending on the reaction conditions. Most nitrobenzene produced is reduced to aniline; smaller amounts are converted to azobenzene, hydrazobenzene (the intermediate for benzidine), and phenylhydroxylamine. Reduction of both the nitro group and the benzene ring affords cyclohexylamine. Nitrobenzene is used as a mild oxidizing agent in the syntheses of quinoline and fuchsin. Nitrobenzene is used to produce lubricating oils such as those used in motors and machinery. Nitrobenzene and its derivatives are used in the manufacture of dyes, drugs, pesticides, polisher, paint, and synthetic rubber.
The prefix nitro- indicates the presence of NO2- radical, while nitrate refers to any salt or ester of nitric acid or the NO3- anion. Nitroso- is the prefix indicating presence of the group -NO and azo- is for -N=N- group. Some range of organic compounds containing nitrogen include nitro compounds (RNO2 ), nitroso compounds (RNO), amines (R3N ), amino acids, and natural alkaloids or nucleotides. The nitrogen ion in nitro compounds is trigonally planar with 120° angles. There are two resonance bonds so that the two oxygens are equivalent. Nitro compounds are strongly basic due to electron withdrawing both inductively and mesomerically. Historically, they are abundant in dyes and explosives. Nitro compounds, organic hydrocarbons having one or more NO2 groups bonded via nitrogen to the carbon framework, are versatile intermediate in organic synthesis.- Michael addition
- Reduction
- Henry Reaction (Nitro-aldol reaction)
- Nef reaction
- O-Alkylation
- Cycloaddition
- Substitution, Elimination, Conversion reaction
- Alkylation, Acylation, and Halogenation
Nitro compounds are readily reduced into amines when reacted with hydrochloric acid. Aromatic nitro compounds also yield anilines, aromatic amine compounds. Nitro compounds are cleaved into two parts by the addition of a molecule of water to produce carbonyl compounds (aldehydes or ketones). Aromatic nitro compounds undergo nucleophilic substitutions to be replaced by the hydroxide anion, resulting in the creation of phenol compounds and by alkoxy nucleophiles to corresponding ethers.
APPEARANCE
ASSAY (GC)
99.5% min
MOISTURE
0.2% max
DINITROBENZENE
0.3% max
UNNITRATED HYDROCARBONS
0.5% max
TRANSPORTATION