2-Chloroethanol
From Wikipedia, the free encyclopedia
| 2-Chloroethanol | |
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| IUPAC name |
2-Chloroethanol
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| Other names | 2-chloroethyl alcohol, ethylene chlorohydrin, glycol chlorohydrin, 2-chloro-1-ethanol, 2-monochloroethanol, 2-hydroxyethyl chloride, β-chloroethanol, β-hydroxyethyl chloride, chloroethanol, δ-chloroethanol, ethylchlorhydrin, ethylene chlorohydrin, glycol monochlorohydrin |
| Identifiers | |
| CAS number | 107-07-3  |
| SMILES |
ClCCO
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| InChI |
1/C2H5ClO/c3-1-2-4/h4H,1-2H2
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| InChI key | SZIFAVKTNFCBPC-UHFFFAOYAF |
| ChemSpider ID | 21106015 |
| Properties | |
| Molecular formula | C2H5ClO |
| Molar mass | 80.52 g/mol |
| Density | 1.197 g/cm³ |
| Melting point |
-67 °C |
| Boiling point |
128-130 °C |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
2-Chloroethanol is an organochlorine compound with the formula HOCH2CH2Cl. This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional groups.
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[edit] Synthesis and applications
2-Chloroethanol is produced by treating ethylene with hypochlorous acid:
- CH2=CH2 + HOCl → HOCH2CH2Cl
2-Chloroethanol was once produced on a large scale as a precursor to ethylene oxide:
- HOCH2CH2Cl + NaOH → C2H4O + NaCl + H2O
This application has been supplanted by the greener direct oxidation of ethylene. Otherwise chloroethanol is used in a number of specialized applications.[1] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.[2] It is a building block in the production of pharmaceuticals, biocides and plasticizers. It is also used for manufacture of thiodiglycol. It is a solvent for cellulose acetate and ethyl cellulose, textile printing dyes, in dewaxing, refining of rosin, extraction of pine lignin, and the cleaning of machines.
[edit] Environmental aspects
Chloroethanol is a metabolite in the degradation of 1,2-dichloroethane. The alcohol is then further oxidized via chloroacetaldehyde to chloroacetate. This metabolic pathway is topical since billions of kilograms of 1,2-dichloroethane are processed annually as a precursor to vinyl chloride.[3]
[edit] Safety
2-Chloroethanol is toxic with an LD50 of 89 mg/kg in rats. Like most organochlorine compounds, chloroethanol combusts to yield hydrogen chloride and phosgene.
[edit] References
- ^ Gordon Y. T. Liu, W. Frank Richey, Joanne E. Betso “Chlorohydrins“ in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_565
- ^ Roderich Raue and John F. Corbett “Nitro and Nitroso Dyes“ in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_383
- ^ 1. Janssen, D. B.; van der Ploeg, J. R. and Pries, F., "Genetics and Biochemistry of 1,2-Dichloroethane Degradation", Biodegradation, 1994, volume 5, pp. 249-57.doi:10.1007/BF00696463
