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
Names
IUPAC name
2-Chloroethanol[2]
Other names
  • Chloroethanol[1]
  • 2-Chloro-1-ethanol[1]
  • β-Chloroethanol[1]
  • δ-Chloroethanol[1]
  • 2-Chloroethyl alcohol[1]
  • Ethylchlorhydrin[1]
  • Ethylene chlorohydrin[1]
  • Glycol chlorohydrin[1]
  • Glycol monochlorohydrin[1]
  • 2-Hydroxyethyl chloride[1]
  • β-Hydroxyethyl chloride[1]
  • 2-Monochloroethanol[1]
Identifiers
107-07-3 YesY
3DMet B01042
878139
ChEBI CHEBI:28200 YesY
ChEMBL ChEMBL191244 YesY
ChemSpider 21106015 YesY
EC number 203-459-7
25389
Jmol-3D images Image
KEGG C06753 YesY
MeSH Ethylene+Chlorohydrin
PubChem 34
RTECS number KK0875000
UNII 753N66IHAN YesY
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 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
H226, H300, H310, H330
P260, P280, P284, P301+310, P302+350
EU classification Very Toxic T+
R-phrases R26/27/28
S-phrases (S1/2), S45
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
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)[citation needed]
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):
TWA 5 ppm (16 mg/m3) [skin][3]
C 1 ppm (3 mg/m3) [skin][3]
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).
 N verify (what isYesY/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.[6] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.[7] 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.[8]

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.[9]

References[edit]

  1. ^ a b c d e f g h i j k l Depositor-supplied synonyms for CID 34
  2. ^ "2-Chloroethanol". Pubchem. 27 May 2015. Retrieved 27 May 2015. 
  3. ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0268". National Institute for Occupational Safety and Health (NIOSH). 
  4. ^ a b "Ethylene chlorohydrin". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  5. ^ http://www.newenv.com/resources/nfpa_chemicals
  6. ^ 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
  7. ^ 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
  8. ^ 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
  9. ^ CDC - NIOSH Pocket Guide to Chemical Hazards