Synthesis of chloroacetone

Preparation of chloroacetone (1-chloropropan-2-one, chloropropanone, monochloroacetone, acetonyl chloride)

Chloroacetone is prepared by the action of chlorine on acetone.

Preparation of chloroacetone

Preparation of chloroacetone

To a round bottom flask, which is fitted with a reflux condenser, a dropping funnel, a gas inlet tube (for the chlorine) and a stirrer (or magnetic stirrer) 101 ml (80 g) of acetone and 20 g of calcium carbonate in lumps are placed. Calcium carbonate is added in order to neutralize the hydrogen chloride, which forms during the reaction. A current of chlorine is passed in the reaction flask through the acetone and 30-40 ml water are gradually added from the dropping-funnel. The reaction mixture is gently heated to the temperature 60° C. When all calcium carbonate in the reaction flask is almost consumed, the current of chlorine is stopped. For the completion of the reaction, the mixture is allowed to stand overnight. Chloroacetone forms in the upper layer which is separated and fractionally distilled. The fraction boiling at 117-121° C is collected yielding pure chloroacetone (b.p. 119° C). It is slightly soluble in water, but easily in organics solvents (alcohol, ether, chloroform and other).

The war gases chemistry and analysis, by M. Sartory, 148, 1939

IUPAC Name

1-chloropropan-2-one

InChI

InChI=1S/C3H5ClO/c1-3(5)2-4/h2H2,1H3

InChI Key

BULLHNJGPPOUOX-UHFFFAOYSA-N

Canonical SMILES

CC(=O)CCl

MeSH Synonyms

1-chloropropanone, chloracetone, chloroacetone

Depositor-Supplied Synonyms

Chloroacetone, 1-Chloropropan-2-one, Chloropropanone, Monochloroacetone, Acetonyl chloride, 2-Propanone, 1-chloro-, Chloro-2-propanone, 1-Chloroacetone, 78-95-5, Tonite, Monochloracetone, 1-CHLORO-2-PROPANONE, Chloromethyl methyl ketone, 3-Chloro-2-propanone, 1-Chloropropanone, Acetone, chloro-, Chloracetone, A-Stoff, .alpha.-Chloroacetone, 1-Chloro-2-ketopropane, Monochloropropanone, Chloracetone [French], 1-Chloro-2-oxopropane, 1-chloro-propan-2-one, Chloroacetone, stabilized, NSC 30673, CCRIS 1943, CHEBI:47220, HSDB 1070, BULLHNJGPPOUOX-UHFFFAOYSA-N, EINECS 201-161-1, UN1695, UN 1695, BRN 0605369, Chloroacetone (unstabilized) [Forbidden], Monochloroacetone (unstabilized) [Forbidden], cloroacetone, chloro acetone, chloro-acetone, alpha-Chloroacetone, 1-Chloroacetone #, CH3COCH2Cl, 2-Propanone,1-chloro-, AC1L1MTS, 1-Chloro-propane-2-one, DSSTox_CID_1547, Chloroacetone (unstabilized), DSSTox_RID_76205, DSSTox_GSID_21547, WLN: G1V1, 10905_ALDRICH, 167479_ALDRICH, AC1Q1K61, Monochloroacetone (unstabilized), CHEMBL1231084, UNII-60ZTR74268, 10905_FLUKA, CTK5E6262, MolPort-000-871-814, LTBB002506, ACT09266, EBD36702, NSC30673, Tox21_200027, ANW-56380, NSC-30673, ZINC01661230, AKOS000119650, 60ZTR74268, DB02672, MCULE-2501365933, RP18558, CAS-78-95-5, NCGC00166003-01, NCGC00166003-02, NCGC00257581-01, AN-23970, KB-76049, LS-122799, TR-025189, FT-0623630, FT-0694897, A23330, Chloroacetone, stabilized [UN1695] [Poison], 20876-EP2275404A1, 20876-EP2275417A2, 20876-EP2280012A2, 20876-EP2281815A1, 20876-EP2284162A2, 20876-EP2284163A2, 20876-EP2287152A2, 20876-EP2298776A1, 20876-EP2308851A1, 20876-EP2314585A1, Chloroacetone, stabilized [UN1695] [Poison], 4-01-00-03215 (Beilstein Handbook Reference), InChI=1/C3H5ClO/c1-3(5)2-4/h2H2,1H, I14-6135, Acetonyl chloride, chloropropanone, 1-chloro-2-propanone, monochloroacetone, 1-chloro-2-ketopropane, 1-chloro-2-oxypropane

Removed Synonyms

chloromethylketone, CID6571, c0271, c0949, ATO, 42492-95-5, MCA

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