Chloroacetone
| Names | |
|---|---|
| IUPAC name
Chloropropanone
| |
| Other names
1-Chloro-2-ketopropane 1-Chloro-2-oxypropane 1-Chloro-2-propanone Acetonyl chloride Chloropropanone Monochloroacetone UN 1695 | |
| Properties | |
| C3H5ClO CH3COCH2Cl | |
| Molar mass | 92.52 g/mol |
| Appearance | Colorless liquid |
| Odor | Pungent, unpleasant odor |
| Density | 1.15 g/cm3 (20 °C) |
| Melting point | −44.5 °C (−48.1 °F; 228.7 K) |
| Boiling point | 119 °C (246 °F; 392 K) |
| 10 g/100 mL (20 °C) | |
| Solubility | Miscible with acetone, chloroform, diethyl ether, ethanol, methanol |
| Vapor pressure | 12.0 mmHg at 25 °C |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 35 °C (95 °F; 308 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
100 mg/kg (rat, oral) 41 mg/kg (rabbit, dermal) |
| Related compounds | |
| Related compounds
|
Acetone |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Chloroacetone is a chemical compound with the formula CH3COCH2Cl. It was used as a tear gas in World War I, now replaced with safer agents.
Contents
Properties
Chemical
Chloroacetone is used in the Feist-Benary synthesis of furans.
Chloroacetone will polymerize slowly under the influence of light with fire or explosion hazard.
Physical
Chloroacetone is a colorless liquid, that may turn amber under prolonged contact with air. It is only slightly soluble in water and sinks in it, though it is miscible with most organic solvents.
Availability
Chloroacetone is sold by chemical suppliers, but due to its hazards, it cannot be acquired by private individuals.
Transportation of unstabilized chloroacetone has been banned in the United States by the US Department of Transportation. Stabilized chloroacetone is in hazard class 6.1 (Poison Inhalation Hazard). Its UN number is 1695.
Preparation
Chloroacetone may be synthesized from the reaction between chlorine and acetone.[1]
Chloroacetone purchased from commercial suppliers contains 5% impurities including mesityl oxide, which is not removed by distillation. Mesityl oxide can be oxidized using acidified potassium permanganate to form a diol (followed by separation with ether), which is removed on subsequent distillation.
Projects
- Make furans
Handling
Safety
Chloroacetone is extremely toxic and an extremely powerful lacrymator. Many hobby chemists that have worked with the stuff, have mentioned that even traces of the substance are enough to cause strong lacrymation, sometimes even for hours. It will also irritate skin, mouth and nose and may even cause injuries at concentrations high enough.
Storage
Chloroacetone must be kept in closed glass or plastic bottles, in dark, hazardous substances cabinets, with a clear hazard label, at 2-8 °C. A stabilizing agent, like 1% w/w calcium carbonate or 0.1% w/w Drapex 39 (epoxidized soybean oil) must be added to stabilize the compound, since chloroacetone without stabilizer is very dangerous.
Disposal
Chloroacetone can be destroyed with a solution of NaOH or KOH, resulting in a crimson colored solution. Make sure to cool both liquids, to limit evaporation of the chloroacetone.
