Chloroacetone

Structural formula
General
Surname	Chloroacetone
other names	Chloro-2-propanone 1-chloro-2-propanone
Molecular formula	C 3 H 5 ClO
Brief description	colorless, tear-irritating liquid with a pungent odor
External identifiers / databases
CAS number 78-95-5 EC number 201-161-1 ECHA InfoCard 100.001.056 PubChem 6571 ChemSpider 6323 DrugBank DB02672 Wikidata Q425346
properties
Molar mass	92.52 g mol −1
Physical state	liquid
density	1.15 g cm −3
Melting point	−44 ° C
boiling point	119 ° C
Vapor pressure	28 h Pa (20 ° C) 105 hPa (50 ° C) 185 hPa (65 ° C)
solubility	miscible with water (100 g · l −1 ), ethanol and diethyl ether
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 226-301-310 + 330-315-319-335-410 P: 210-273-280-302 + 352-304 + 340-305 + 351 + 338-308 + 310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chloracetone is a clear liquid that irritates the eyes. They can be produced relatively easily from acetone and chlorine .

history

During the First World War , chloroacetone was used as an eye irritant , first in November 1914 by France under the code name "Tonite". Later it was used by the French under the code name "Martonite", a mixture of bromine and chloroacetone, as an eye-irritating agent.

Extraction and presentation

Industrial production takes place by chlorination of acetone, for example by introducing chlorine gas into a suspension of calcium carbonate in acetone. If the chlorination is too vigorous, other chloroacetone compounds such as di- or trichloroacetone are also formed as by-products . These are considerably more toxic, but less irritating than (mono-) chloroacetone, and would have to be separated off by distillation . However, this is not easy because of the close proximity of the boiling points.

safety instructions

In chemical laboratories, the unintentional release of chloroacetone can occur if acetone is used as a solvent during chlorination or if acetone is used to clean equipment that is contaminated with chlorinating agents or chlorine (in dissolved form). Contact leads to considerable irritation and even severe burns to the eyes, and the skin and airways are also attacked. When producing acetone peroxide with hydrochloric acid as a catalyst, chloroacetone can be formed if the reaction mixture becomes too hot.

Individual evidence

1. ↑ ^{a b} Entry on chloroacetone. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
2. ↑ ^{a b c d e f g h i} Entry on chloroacetone in the GESTIS substance database of the IFA , accessed on January 17, 2020(JavaScript required) .