Chemistry:2-Chloroethanol

From HandWiki
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[1]
Other names
  • 2-Chloroethanol[1]
  • beta-Chloroethanol[2]
  • 2-Chloro-1-ethanol[2]
  • β-Chloroethanol[2]
  • δ-Chloroethanol[2]
  • 2-Chloroethyl alcohol[2]
  • Ethyl chlorhydrin[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
878139
ChEBI
ChEMBL
ChemSpider
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 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[3]
log P −0.107
Vapor pressure 700 Pa (at 20 °C)
1.441
Thermochemistry
−1.1914 MJ/mol
Hazards
Main hazards Highly toxic and flammable
GHS pictograms GHS02: Flammable GHS06: Toxic
GHS Signal word DANGER
H226, H300+310+330Script error: No such module "Preview warning".Category:GHS errors
P260, P280, P284, P301+310, P302+350
NFPA 704 (fire diamond)
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 fuelHealth code 4: Very short exposure could cause death or major residual injury. E.g. VX gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial 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):
  • 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 h)
  • 32 ppm (rat, 4 h)
  • 260 ppm (guinea pig)
  • 33 ppm (rat, 4 h)
  • 87 ppm (rat)
  • 115 ppm (mouse)[4]
NIOSH (US health exposure limits):
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).
☒N verify (what is ☑Y☒N ?)
Infobox references
Tracking categories (test):

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).[6] 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.[7]

Synthesis and applications

2-Chloroethanol is produced by treating ethylene with hypochlorous acid:[7]

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.[7] Many of these applications entail its use in installing 2-hydroxyethyl groups.[8] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.[9] 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.[10]

Safety

2-Chloroethanol is toxic with an -1">50 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 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.[11]

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.[12][failed verification]

References

  1. ↑ 1.0 1.1 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. p. 29. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. "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. ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 2.10 2.11 Depositor-supplied synonyms for CID 34.
  3. ↑ 3.0 3.1 3.2 3.3 NIOSH Pocket Guide to Chemical Hazards. "#0268". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0268.html. 
  4. ↑ 4.0 4.1 "Ethylene chlorohydrin". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/idlh/107073.html. 
  5. ↑ "NFPA Chemicals". http://www.newenv.com/resources/nfpa_chemicals. 
  6. ↑ Ethylene chlorohydrin: properties
  7. ↑ 7.0 7.1 7.2 Liu, Gordon Y. T.; Richey, W. Frank; Betso, Joanne E.; Hughes, Brian; Klapacz, Joanna; Lindner, Joerg (2014). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_565.pub2. 
  8. ↑ Butler J; Kellogg R (1987). "Synthesis of Macrocyclic Sulfides Using Cesium Thiolates: 1,4,8,11-Tetrathiacyclotetradecane". Organic Syntheses 65 (150): 150. doi:10.15227/orgsyn.065.0150. 
  9. ↑ Raue, Roderich; Corbett, John F. (2002). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_383. 
  10. ↑ Janssen, D. B.; van der Ploeg, J. R.; Pries, F. (1994). "Genetics and Biochemistry of 1,2-Dichloroethane Degradation". Biodegradation 5 (3–4): 249–57. doi:10.1007/BF00696463. PMID 7765836. https://pure.rug.nl/ws/files/14528144/1994BiodegradJanssen.pdf. 
  11. ↑ CDC - NIOSH Pocket Guide to Chemical Hazards
  12. ↑ Code of Federal Regulations (July 1, 2008 ed.). Government Printing Office. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:2-Chloroethanol&oldid=3324577"