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somewhat decreased susceptibility to further chlorination. Industrially the reaction is conducted as a continuous process to minimize the formation of dichlorobenzenes.
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, dyestus, 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)disulde, and 2-nitroaniline by nucleophilic
displacement of the chloride with sodium hydroxide,
sodium methoxide, sodium disulde and ammonia. The
conversion of the 4-nitrochlorobenzene (CAS#100-00-5)
are similar.[3]
5 Toxicology
Cl
Cl2
FeCl 3
6 References
HCl
[1] Weber,
Manfred;
Weber,
Markus;
KleineBoymann, Michael (2004).
Phenol.
Ullmanns Encyclopedia of Industrial Chemistry.
doi:10.1002/14356007.a19_299.pub2.
ISBN
3527306730.
[2] Rossberg, Manfred; Lendle, Wilhelm; Peiderer, Gerhard; Tgel, Adolf; Dreher, Eberhard-Ludwig; Langer,
Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack,
Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August;
Torkelson, Theodore R.; Lser, Eckhard; Beutel, Klaus
K.; Mann, Trevor (2006). Chlorinated Hydrocarbons. Ullmanns Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a06_233.pub2. ISBN
3527306730.
[3] Booth, Gerald (2000). Nitro Compounds, Aromatic.
Ullmanns Encyclopedia of Industrial Chemistry.
doi:10.1002/14356007.a17_411. ISBN 3527306730.
[4] U. Beck, E. Lser Chlorinated Benzenes and other
Nucleus-Chlorinated Aromatic Hydrocarbons Ullmanns
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): 695701.
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) 695701] extquotedbl.
Systematic and Applied Microbiology 29 (2): 182110.
doi:10.1016/j.syapm.2005.11.005.
[6] CDC - NIOSH Pocket Guide to Chemical Hazards
REFERENCES
7.1
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