2-Chloroethanol

2-Chloroethanol
Skeletal formula of 2-chloroethanol
Ball and stick model of 2-chloroethanol
Spacefill model of 2-chloroethanol
Names
Preferred IUPAC name
2-Chloroethan-1-ol
Other names
  • 2-Chloroethanol
  • beta-Chloroethanol
  • 2-Chloro-1-ethanol
  • β-Chloroethanol
  • δ-Chloroethanol
  • 2-Chloroethyl alcohol
  • Ethyl chlorhydrin
  • Ethylene chlorohydrin
  • Glycol chlorohydrin
  • Glycol monochlorohydrin
  • 2-Hydroxyethyl chloride
  • β-Hydroxyethyl chloride
  • 2-Monochloroethanol
Identifiers
3D model (JSmol)
3DMet
878139
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.146 Edit this at Wikidata
EC Number
  • 203-459-7
25389
KEGG
MeSH Ethylene+Chlorohydrin
RTECS number
  • KK0875000
UNII
UN number 1135
  • InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 checkY
    Key: SZIFAVKTNFCBPC-UHFFFAOYSA-N checkY
  • OCCCl
Properties
C2H5ClO
Molar mass 80.51 g·mol−1
Appearance Colourless liquid
Odor ether-like
Density 1.201 g/mL
Melting point −62.60 °C; −80.68 °F; 210.55 K
Boiling point 127–131 °C; 260–268 °F; 400–404 K
Miscible
log P −0.107
Vapor pressure 700 Pa (at 20 °C)
1.441
Thermochemistry
−1.1914 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic and flammable
GHS labelling:
GHS02: Flammable GHS06: Toxic
Danger
H226, H300+H310+H330
P260, P280, P284, P301+P310, P302+P350
NFPA 704 (fire diamond)
4
2
0
Flash point 55 °C (131 °F; 328 K)
425 °C (797 °F; 698 K)
Explosive limits 5–16%
Lethal dose or concentration (LD, LC):
  • 67mg/kg (dermal, rabbit)[citation needed]
  • 72mg/kg (rat, oral)
  • 81mg/kg (mouse, oral)
  • 71mg/kg (rat, oral)
  • 110mg/kg (guinea pig, oral)
  • 7.5ppm (rat, 1h)
  • 32ppm (rat, 4h)
  • 260ppm (guinea pig)
  • 33ppm (rat, 4h)
  • 87ppm (rat)
  • 115ppm (mouse)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 5ppm (16mg/m3) [skin]
REL (Recommended)
C 1ppm (3mg/m3) [skin]
IDLH (Immediate danger)
7ppm
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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.[failed verification]


This page was last updated at 2023-06-02 08:36 UTC. Update now. View original page.

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