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2-Chloroethanol

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2-Chloroethanol
Names
IUPAC name 2-Chloroethanol
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.146 Edit this at Wikidata
KEGG
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2Key: SZIFAVKTNFCBPC-UHFFFAOYSA-N
  • InChI=1/C2H5ClO/c3-1-2-4/h4H,1-2H2Key: SZIFAVKTNFCBPC-UHFFFAOYAF
SMILES
  • ClCCO
Properties
Chemical formula C2H5ClO
Molar mass 80.52 g/mol
Density 1.197 g/cm³
Melting point -67 °C
Boiling point 128-130 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

Synthesis and applications

2-Chloroethanol is produced by treating ethylene with hypochlorous acid:

Synthesis of 2-chlorethanol by treating ethylene with hypochlorous acid

2-Chloroethanol was once produced on a large scale as a precursor to ethylene oxide:

Synthesis of ethylene oxide from 2-chloroethanol

This application has been supplanted by the greener direct oxidation of ethylene. Otherwise chloroethanol is used in a number of specialized applications. Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol. 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.

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.

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.

References

  1. 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
  2. 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
  3. 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
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