2-Chloroethanol

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2-Chloroethanol
Skeletal formula of 2-chloroethanol 2-Chloroethanol-2D-by-AHRLS-2012.png
Skeletal formula of 2-chloroethanol
Ball and stick model of 2-chloroethanol 2-chloroethanol-3D-balls.png
Ball and stick model of 2-chloroethanol
Spacefill model of 2-chloroethanol 2-chloroethanol-3D-vdW.png
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)
878139
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.146 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-459-7
25389
KEGG
MeSH Ethylene+Chlorohydrin
PubChem CID
RTECS number
  • KK0875000
UNII
UN number 1135
  • InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 Yes check.svgY
    Key: SZIFAVKTNFCBPC-UHFFFAOYSA-N Yes check.svgY
  • OCCCl
Properties
C2H5ClO
Molar mass 80.51 g·mol−1
AppearanceColourless 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
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic and flammable
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg
Danger
H226, H300+H310+H330
P260, P280, P284, P301+P310, P302+P350
NFPA 704 (fire diamond)
NFPA 704.svgHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 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 fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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):
  • 67 mg/kg (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  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).
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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]

Contents

Synthesis and applications

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

Synthesis Chloroethanol B.svg

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

Synthesis Ethylene oxide.svg
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 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 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 2 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. 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 or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. "NFPA Chemicals". New Environment Inc.
  6. ↑ Ethylene chlorohydrin: properties
  7. 1 2 3 Liu, Gordon Y. T.; Richey, W. Frank; Betso, Joanne E.; et al. (2014). "Chlorohydrins". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_565.pub2. ISBN   978-3-527-30673-2.
  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). "Nitro and Nitroso Dyes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_383. ISBN   978-3-527-30673-2.
  10. ↑ Janssen, D. B.; van der Ploeg, J. R.; Pries, F. (1994). "Genetics and Biochemistry of 1,2-Dichloroethane Degradation" (PDF). Biodegradation. 5 (3–4): 249–57. doi:10.1007/BF00696463. PMID   7765836. S2CID   475768.
  11. ↑ CDC - NIOSH Pocket Guide to Chemical Hazards
  12. ↑ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF). Code of Federal Regulations (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.
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