2-Chloroethanol

Template:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox headerbarTemplate:Chembox headerbarTemplate:Chembox OHS (set)Template:Chembox GHS (set)Template:Chembox Lethal amounts (set)Template:Chembox setHeaderTemplate:Chembox setDatarowTemplate:Chembox setDatarowTemplate:Chembox setDatarowTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Chembox Footer

2-Chloroethanol

Template:Chembox image sbs cell
Template:Longitem	Template:Unbulleted list
Template:Longitem	878139
ChEBI	Template:Unbulleted list
ChemSpider	Template:Unbulleted list
DrugBank	Template:Unbulleted list
EC Number	Template:Unbulleted list
Template:Longitem	25389
KEGG	Template:Unbulleted list
MeSH	Ethylene+Chlorohydrin
Template:Longitem	Template:Unbulleted list
RTECS number	Template:Unbulleted list
UN number	1135
Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Colourless liquid
Odor	ether-like
Density	1.201 g/mL
Melting point	Template:Chembox CalcTemperatures
Boiling point	Template:Chembox CalcTemperatures
log P	−0.107
Vapor pressure	700 Pa (at 20 °C)
Template:Longitem	1.441
Template:Longitem	−1.1914 MJ/mol
NFPA 704 (fire diamond)	Template:NFPA 704 diamond
Flash point	Template:Chembox CalcTemperatures
Template:Longitem	Template:Chembox CalcTemperatures
Explosive limits	5–16%
Template:Longitem	Template:Unbulleted list

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH₂CH₂Cl and the simplest beta-halohydrin (chlorohydrin). 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 group.

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

HOCH₂CH₂Cl + NaOH → C₂H₄O + NaCl + H₂O

This application has been supplanted by the more economic direct oxidation of ethylene. Otherwise chloroethanol is still used in the production of pharmaceuticals, biocides, and plasticizers. Many of these applications entail its use in installing 2-hydroxyethyl groups. Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol. 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 releases hydrochloric acid and phosgene when burned.

In regards to dermal exposure to 2-chloroethanol, the Occupational Safety and Health Administration has set a permissible exposure limit of 5ppm (16mg/m³) over an eight-hour time-weighted average, while the National Institute for Occupational Safety and Health has a more protective recommended exposure limit of a 1ppm (3mg/m³) exposure ceiling.

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.