2-Chloroethanol

2-Chloroethanol
Names
Preferred IUPAC name
2-Chloroethan-1-ol[1]
Other names
  • 2-Chloroethanol[1]
  • Chloroethanol[2]
  • 2-Chloro-1-ethanol[2]
  • β-Chloroethanol[2]
  • δ-Chloroethanol[2]
  • 2-Chloroethyl alcohol[2]
  • Ethylchlorhydrin[2]
  • Ethylene chlorohydrin[2]
  • Glycol chlorohydrin[2]
  • Glycol monochlorohydrin[2]
  • 2-Hydroxyethyl chloride[2]
  • β-Hydroxyethyl chloride[2]
  • 2-Monochloroethanol[2]
Identifiers
3D model (JSmol)
3DMet B01042
878139
ChEBI
ChemSpider
ECHA InfoCard 100.003.146
EC Number 203-459-7
25389
KEGG
MeSH Ethylene+Chlorohydrin
RTECS number KK0875000
UNII
UN number 1135
Properties
C2H5ClO
Molar mass 80.51 g·mol−1
Appearance Colourless liquid
Odor faint, ether-like
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
miscible[3]
log P −0.107
Vapor pressure 700 Pa (at 20 °C)
1.441
Thermochemistry
−1.1914 MJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
H226, H300, H310, H330
P260, P280, P284, P301+310, P302+350
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
2
4
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):
67 mg kg−1 (dermal, rabbit)
72 mg/kg (rat, oral)
81 mg/kg (mouse, oral)
71 mg/kg (rat, oral)
110 mg/kg (guinea pig, oral)[4]
7.5 ppm (rat, 1 hr)
32 ppm (rat, 4 hr)
260 ppm (guinea pig)
33 ppm (rat, 4 hr)
87 ppm (rat)
115 ppm (mouse)[4]
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 5 ppm (16 mg/m3) [skin][3]
REL (Recommended)
 C 1 ppm (3 mg/m3) [skin][3]
IDLH (Immediate danger)
 7 ppm[3]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2-Chloroethanol is an chemical compound with the formula HOCH2CH2Cl and the simplest 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 groups.

Synthesis and applications

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

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

This application has been supplanted by the greener direct oxidation of ethylene. Otherwise chloroethanol is used in a number of specialized applications.[5] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.[6] 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.[7]

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.

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.[8]

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.[9]

References

  1. 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 29. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001. For example, the omission of the locant ‘1’ in 2-chloroethanol, while permissible in general usage, is not allowed in preferred IUPAC names, thus the name 2-chloroethan-1-ol is the PIN.
  2. 1 2 3 4 5 6 7 8 9 10 11 12 Depositor-supplied synonyms for CID 34
  3. 1 2 3 4 "NIOSH Pocket Guide to Chemical Hazards #0268". National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 "Ethylene chlorohydrin". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  5. ↑ 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
  6. ↑ 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
  7. ↑ 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
  8. ↑ CDC - NIOSH Pocket Guide to Chemical Hazards
  9. ↑ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011.
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