Chlorobenzene

Chlorobenzene is an aromatic organic compound with
the chemical formula C6 H5 Cl. This colorless, flammable
liquid is a common solvent and a widely used intermediate
in the manufacture of other chemicals.

somewhat decreased susceptibility to further chlorination. Industrially the reaction is conducted as a continuous process to minimize the formation of dichlorobenzenes.

1

3 Biodegradation

Uses

Chlorobenzene once was used in the manufacture of Rhodococcus phenolicus is a bacterium species able to decertain pesticides, most notably DDT by reaction with grade chlorobenzene as sole carbon sources.[5]
chloral (trichloroacetaldehyde), but this application has
declined with the diminished use of DDT. At one time,
chlorobenzene was the main precursor for the manufac4 Safety
ture of phenol:[1]
C6 H5 Cl + NaOH → C6 H5 OH + NaCl

Chlorobenzene exhibits “low to moderate” toxicity as indicated by its LD50 of 2.9 g/kg.[2] The Occupational
Safety and Health Administration has set a permissible
exposure limit at 75 ppm (350 mg/m3 ) over an
eight hour time-weighted average for workers handling
chlorobenzene.[6]

The major use of chlorobenzene is as an intermediate in the production of commodities such as herbicides, dyestuffs, and rubber. Chlorobenzene is also
used as a high-boiling solvent in many industrial applications as well as in the laboratory.[2] Chlorobenzene is nitrated on a large scale to give a mixture
of 2- and 4-nitrochlorobenzenes, which can be separated by fractional crystallization followed by distillation. 2-Nitrochlorobenzene (CAS#88-73-3) is converted to related 2-nitrophenol, 2-nitroanisole, bis(2nitrophenyl)disulfide, and 2-nitroaniline by nucleophilic
displacement of the chloride with sodium hydroxide,
sodium methoxide, sodium disulfide and ammonia. The
conversion of the 4-nitrochlorobenzene (CAS#100-00-5)
are similar.[3]

5 Toxicology

Chlorobenzene is not a naturally occurring compound,
but because of its manufacture, can persist in soil for
several months, in air for about 3.5 days, and in water
for less than one day. Humans may be exposed to this
agent via breathing contaminated air (primarily via occupational exposure), eating contaminated food or water, or
by coming into contact with contaminated soil (typically
near hazardous waste sites). However, because it has only
2 Production
been found at 97 out of 1,177 NPL hazardous waste sites,
it is not considered a widespread environmental contamChlorobenzene was first described in 1851. Presently it is inant.
manufactured by chlorination of benzene in the presence Upon entering the body, typically via contaminated air,
of a catalytic amount of Lewis acid such as ferric chloride, chlorobenzene is excreted both via the lungs and the urisulfur dichloride, and anhydrous aluminium chloride:[4]
nary system.

Cl
Cl2

FeCl 3

6 References

+

HCl

The catalyst enhances the electrophilicity of the chlorine.
Because chlorine is electronegative, C6 H5 Cl exhibits
1

[1] Weber,
Manfred;
Weber,
Markus;
KleineBoymann, Michael (2004).
“Phenol”.
“Ullmann’s Encyclopedia of Industrial Chemistry”.
doi:10.1002/14356007.a19_299.pub2.
ISBN
3527306730.

2

[2] Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer,
Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack,
Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August;
Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus
K.; Mann, Trevor (2006). “Chlorinated Hydrocarbons”. “Ullmann’s Encyclopedia of Industrial Chemistry”. doi:10.1002/14356007.a06_233.pub2. ISBN
3527306730.
[3] Booth, Gerald (2000). “Nitro Compounds, Aromatic”.
“Ullmann’s Encyclopedia of Industrial Chemistry”.
doi:10.1002/14356007.a17_411. ISBN 3527306730.
[4] U. Beck, E. Löser “Chlorinated Benzenes and other
Nucleus-Chlorinated Aromatic Hydrocarbons” Ullmann’s
Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH,
Weinheim. doi:10.1002/14356007.o06_o03
[5] Rehfuss, M.; Urban, J. (2005). extquotedblRhodococcus
phenolicus sp. nov., a novel bioprocessor isolated actinomycete with the ability to degrade chlorobenzene,
dichlorobenzene and phenol as sole carbon sources”.
Systematic and Applied Microbiology 28 (8): 695–701.
doi:10.1016/j.syapm.2005.05.011. PMID 16261859.
Erratum: Rehfuss, M. (2006). “Erratum to extquotedblRhodococcus phenolicus sp. nov., a novel bioprocessor isolated actinomycete with the ability to degrade chlorobenzene, dichlorobenzene and phenol as
sole carbon sources” [Systematic and Applied Microbiology 28 (2005) 695–701] extquotedbl.
Systematic and Applied Microbiology 29 (2): 182–110.
doi:10.1016/j.syapm.2005.11.005.
[6] CDC - NIOSH Pocket Guide to Chemical Hazards

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REFERENCES

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Text and image sources, contributors, and licenses

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• Chlorobenzene Source: http://en.wikipedia.org/wiki/Chlorobenzene?oldid=600803014 Contributors: Spiffy sperry, Xezbeth, Benjahbmm27, V8rik, DePiep, Physchim62, Gaius Cornelius, Yyy, Shaddack, David Berardan,
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