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| chlorobenzene | |
|---|---|
| Name | Chlorobenzene |
| IUPAC name | Chlorobenzene |
| Other names | Phenyl chloride |
| CAS number | 108-90-7 |
| Formula | C6H5Cl |
| Molar mass | 112.56 g/mol |
| Density | 1.106 g/cm3 (20 °C) |
| Melting point | -45 °C |
| Boiling point | 131 °C |
| Solubility | 0.35 g/L (20 °C) |
chlorobenzene
Chlorobenzene is an aromatic halocarbon consisting of a benzene ring substituted with a single chlorine atom. It is a colorless, volatile liquid widely used as a solvent and intermediate in chemical manufacture, notable for its role in the production of agrochemicals, dyes, and intermediates for pharmaceuticals. Industrial relevance and environmental persistence have made it a subject of study across chemical engineering and environmental science communities.
Chlorobenzene is an organochlorine with a monosubstituted Benzene core; its electronic structure reflects resonance stabilization akin to Clar's sextet descriptions applied in Linus Pauling–era aromaticity discussions. The C–Cl bond exhibits partial ionic character influenced by inductive effects emphasized in Friedrich August Kekulé derivations of aromatic systems and in modern valence bond accounts associated with Gilbert N. Lewis frameworks. Physical constants such as refractive index, vapor pressure, and heat capacity are cataloged similarly to data for Toluene, Benzene, Chlorobenzene-related solvents, and other industrial aromatics studied at institutions like Massachusetts Institute of Technology and Imperial College London. Spectroscopic signatures include characteristic peaks in Infrared spectroscopy and Nuclear magnetic resonance spectra comparable to substituted benzenes analyzed in laboratories at University of Cambridge and California Institute of Technology.
Commercial production traditionally employs electrophilic aromatic substitution: chlorination of Benzene using catalysts such as Iron(III) chloride or heterogeneous catalysts modeled after developments from researchers at BASF and DuPont. Historic process optimization parallels investigations by industrial chemistry groups at Dow Chemical Company and engineering research at Siemens and General Electric. Alternative routes include dehydrochlorination of 1,2-dichloroethane derivatives and selective catalytic dehalogenation techniques advanced in projects affiliated with Shell and Chevron. Process safety, distillation, and waste-treatment strategies reflect engineering practices developed at National Institute of Standards and Technology and industrial safety programs at Occupational Safety and Health Administration–aligned facilities.
Chlorobenzene serves as an intermediate in the synthesis of herbicides and pesticides pioneered by companies like Bayer and Ciba-Geigy, and in dye manufacture with historical links to firms such as DuPont and AkzoNobel. It is a solvent in processes associated with 3M and used in rubber and resin formulations developed by Goodyear and BASF. Chlorobenzene is a precursor to aniline derivatives and nitrochlorobenzenes used in pharmaceutical syntheses practiced at Pfizer, Merck & Co., GlaxoSmithKline, and Novartis. Its role in organic chemistry overlaps with reagent development at academic centers including Harvard University, Stanford University, University of Oxford, and ETH Zurich.
In the environment, chlorobenzene undergoes volatilization, photolysis, and microbial degradation; studies by researchers at United States Environmental Protection Agency and European Chemicals Agency have examined its persistence in soil and groundwater akin to concerns around other organochlorines like DDT and PCBs. Aerobic and anaerobic biodegradation pathways involve dechlorination and ring cleavage, processes explored in microbial ecology programs at Woods Hole Oceanographic Institution and Lawrence Berkeley National Laboratory. Remediation techniques such as pump-and-treat, air sparging, and bioremediation have been piloted by consultants from EPA Superfund projects and environmental engineering groups at Jacobs Engineering and AECOM.
Acute exposure to chlorobenzene can cause central nervous system depression and irritation; clinical toxicology literature from centers like Mayo Clinic, Johns Hopkins Hospital, and Cleveland Clinic document symptoms similar to solvent exposure cases reported in occupational health studies by World Health Organization and National Institute for Occupational Safety and Health. Chronic exposure considerations reference carcinogenicity assessments by panels at International Agency for Research on Cancer and toxicological reviews compiled by Agency for Toxic Substances and Disease Registry. Treatment protocols for solvent ingestion, inhalation, or dermal exposure draw on emergency medicine guidance disseminated through American College of Emergency Physicians and occupational health guidance published by International Labour Organization.
Regulatory limits and classification have been set by agencies such as United States Environmental Protection Agency, European Chemicals Agency, Health Canada, and national authorities including Food and Drug Administration for specific uses. Workplace exposure limits are recommended by Occupational Safety and Health Administration and NIOSH, and safety data sheet practices reflect standards from International Organization for Standardization and American National Standards Institute. Transportation and hazardous-waste handling follow protocols shaped by Department of Transportation (United States), International Maritime Organization, and United Nations model regulations, with incident response frameworks informed by agencies like Federal Emergency Management Agency and Royal Society for the Prevention of Accidents.
Category:Chlorinated benzenes