Chloroacetone

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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):
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.

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 and it's strongly irritant.

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.

References

  1. https://www.prepchem.com/synthesis-of-chloroacetone

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