2-Chloroethanol

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
CAS Number	107-07-3 ;
3D model (JSmol)	Interactive image;
3DMet	B01042;
Beilstein Reference	878139
ChEBI	CHEBI:28200 ;
ChEMBL	ChEMBL191244 ;
ChemSpider	21106015 ;
ECHA InfoCard	100.003.146
EC Number	203-459-7;
Gmelin Reference	25389
KEGG	C06753 ;
MeSH	Ethylene+Chlorohydrin
PubChem CID	34;
RTECS number	KK0875000;
UNII	753N66IHAN ;
UN number	1135
CompTox Dashboard (EPA)	DTXSID1021877 ;
	InChI InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 Key: SZIFAVKTNFCBPC-UHFFFAOYSA-N ;
	SMILES OCCCl;
Properties
Chemical formula	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
Solubility in water	Miscible[3]
log P	−0.107
Vapor pressure	700 Pa (at 20 °C)
Refractive index (nD)	1.441
Thermochemistry
Std enthalpy of; combustion (ΔcH⦵298)	−1.1914 MJ/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic and flammable
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H300+H310+H330
Precautionary statements	P260, P280, P284, P301+P310, P302+P350
NFPA 704 (fire diamond)	4 2 0
Flash point	55 °C (131 °F; 328 K)
Autoignition; temperature	425 °C (797 °F; 698 K)
Explosive limits	5–16%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	67 mg/kg (dermal, rabbit); 72 mg/kg (rat, oral); 81 mg/kg (mouse, oral); 71 mg/kg (rat, oral); 110 mg/kg (guinea pig, oral)[4];
LC50 (median concentration)	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	Chloromethane; Chloroiodomethane; Bromochloromethane; Dibromochloromethane; Isobutyl chloride; 2-Bromo-1-chloropropane;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

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

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]

References

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.
Depositor-supplied synonyms for CID 34.
NIOSH Pocket Guide to Chemical Hazards. "#0268". National Institute for Occupational Safety and Health (NIOSH).
"Ethylene chlorohydrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
"NFPA Chemicals". New Environment Inc.
Ethylene chlorohydrin: properties
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.
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.
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.
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.
CDC - NIOSH Pocket Guide to Chemical Hazards
"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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[iupac2013-1] 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.

[pubchem-2] Depositor-supplied synonyms for CID 34.

[PGCH-3] NIOSH Pocket Guide to Chemical Hazards. "#0268". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-4] "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

[Ullmann-7] 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.

[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.

[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.