2-Chloroethanol

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2-Chloroethanol
Skeletal formula of 2-chloroethanol
Ball and stick model of 2-chloroethanol Spacefill model of 2-chloroethanol
Identifiers
CAS number 107-07-3 YesY
PubChem 34
ChemSpider 21106015 YesY
UNII 753N66IHAN YesY
EC number 203-459-7
UN number 1135
KEGG C06753 YesY
MeSH Ethylene+Chlorohydrin
ChEBI CHEBI:28200 YesY
ChEMBL CHEMBL191244 YesY
RTECS number KK0875000
Beilstein Reference 878139
Gmelin Reference 25389
3DMet B01042
Jmol-3D images Image 1
Properties
Molecular formula C2H5ClO
Molar mass 80.51 g mol−1
Appearance Colourless liquid
Density 1.201 g mL−1
Melting point −62.60 °C; −80.68 °F; 210.55 K
Boiling point 127 to 131 °C; 260 to 268 °F; 400 to 404 K
log P −0.107
Vapor pressure 700 Pa (at 20 °C)
Refractive index (nD) 1.441
Thermochemistry
Std enthalpy of
combustion
ΔcHo298
−1.1914 MJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H226, H300, H310, H330
GHS precautionary statements P260, P280, P284, P301+310, P302+350
EU Index 603-028-00-7
EU classification Very Toxic T+
R-phrases R26/27/28
S-phrases (S1/2), S45
Flash point 55 °C (131 °F; 328 K)
Explosive limits 5–16%
LD50 67 mg kg−1 (dermal, rabbit)
Related compounds
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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.

Synthesis and applications[edit]

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.[2] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.[3] 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[edit]

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.[4]

Safety[edit]

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.

In regards to dermal exposure to 2-chloroethanol, the Occupational Safety and Health Administration has set a permissible exposure limit of 5 ppm (16 mg/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 1 ppm (3 mg/m3) exposure ceiling.[5]

References[edit]

  1. ^ a b c d e f g h i j k l Depositor-supplied synonyms for CID 34
  2. ^ 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
  3. ^ 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
  4. ^ 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
  5. ^ CDC - NIOSH Pocket Guide to Chemical Hazards