2-Chloroethanol
| Names | |
|---|---|
| IUPAC name
2-Chloroethan-1-ol
| |
| Other names
2-Chloro-1-ethanol
2-Chloroethyl alcohol 2-Monochloroethanol Chloroethanol Ethylchlorhydrin Ethylene chlorohydrin β-Chloroethanol δ-Chloroethanol | |
| Properties | |
| C2H5ClO HOCH2CH2Cl | |
| Molar mass | 80.51 g/mol |
| Appearance | Colorless liquid |
| Odor | Sweet, ether-like |
| Density | 1.201 g/cm3 (25 °C) |
| Melting point | −62.6 °C (−80.7 °F; 210.6 K) |
| Boiling point | 127–131 °C (261–268 °F; 400–404 K) |
| Miscible | |
| Solubility | Reacts with alkalis Misicble with acetone, benzene, ethanol, toluene |
| Vapor pressure | 700 Pa (at 20 °C) |
| Thermochemistry | |
| Hazards | |
| Safety data sheet | Sigma-Alrich |
| Flash point | 55 °C (131 °F; 328 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
71 mg/kg (rat, oral) 81 mg/kg (mouse, oral) 110 mg/kg (guinea pig, oral) |
| Related compounds | |
| Related compounds
|
Ethanol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
2-Chloroethanol is a chemical compound with the formula HOCH2CH2Cl and the simplest chlorohydrin.
While 2-chloroethanol is also sometimes referred to simply as "chloroethanol", the same term can also be used for the less known and less stable 1-chloroethanol isomer.
Contents
Properties
Chemical
Dehydrohalogenation of 2-chloroethanol with an alkali hydroxide (like KOH) at room temperature will yield ethylene oxide.
Physical
2-Chloroethanol is a colorless liquid, miscible with water and organic solvents.
Availability
2-Chloroethanol is sold by chemical suppliers, though it's not cheap or easy to acquire.
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.
Preparation
2-Chloroethanol can be prepared by refluxing ethylene glycol with concentrated hydrochloric acid or hydrogen chloride, though the yield isn't that great.
A better route involves treating ethylene with hypochlorous acid. This is done by bubbling ethylene through an acidified solution of calcium or sodium hypochlorite.
Projects
- Make ethylene oxide
- Preparation of dyes
- Preparation of glycol ethers (2-methoxyethanol and 2-ethoxyethanol)
Handling
Safety
2-Chloroethanol is very toxic, with an estimated LD50 of 81-89 mg/kg in rats. It can also absorb through skin contact, and thus proper protection like chemically resistant gloves must be worn when handling the compound.
Storage
In closed bottles, with a clear hazardous chemical label, in well ventilated locations.
Disposal
To neutralize this compound, you may use Fenton's reagent. Avoid using KOH to hydrolyze the compound, as the neutralization reaction will produce the highly volatile, extremely flammable and carcinogenic ethylene oxide, which is a severe explosion hazard.
