Although chlorobenzene is not formed in any significant quantity naturally, the United States chemical industry synthesized 231 million pounds of chlorobenzene in 1992 alone. Chlorobenzene is commonly used in the manufacture of nitrochlorobenzenes, phenol, aniline, and other industrial chemicals. It also functions as a paint solvent, heat-transfer medium, and an intermediate compound in the manufacture of some pesticides. Most chlorobenzene that is discharged into the environment quickly evaporates and is subsequently degraded atmospherically via reactions with photochemically-generated hydroxyl radicals. Enzymes involved in the microbial degradation of chlorobenzene are believed to have evolved from simliar enzymes catalyzing the degradation of benzene and toluene (Werlen et al., 1996).
The Japanese Database for Environmental Fate of Chemicals has information on the rates and pathways of Biodegradation of Chlorophenols and Chlorobenzenes in Sediments.
The following is a text-format chlorobenzene pathway map. Organisms which can initiate the pathway are given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in Graphic (7k) format.
from the
Chlorobenzene <------------- Beta-HCH Pathway
Pseudomonas sp.
P51, JS150, RHO1, JS6
|
|
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| chlorobenzene dioxygenase
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v
3-Chloro-cis-1,2-dihydroxycyclohexa-3,5-diene
|
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| cis-1,2-dihydrobenzene-1,2-diol
| dehydrogenase
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v
3-Chlorocatechol---------------------+
| |
| |
| |
| catechol 1,2- | 2,3-dihydroxybiphenyl
| dioxygenase | 1,2-dioxygenase
| |
| |
v v
2-Chloro-cis,cis-muconate 3-chloro-2-hydroxymuconic
| semialdehyde
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| chloromuconate cycloisomerase
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v
trans-4-Carboxymethylenebut-2-en-4-olide
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| dienelactone hydrolase
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v from the
Maleylacetate <--- 4-Carboxy-4'-sulfoazobenzene
| Pathway
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| maleylacetate reductase
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v
3-Oxoadipate
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|
|
v
Intermediary Metabolism (KEGG)
Page Author(s): Ryan McLeish
March 29, 2008 Contact Us
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