Synthesis of acetone (2-propanone; dimethyl ketone)

Preparation of acetone

Alternative Names: Acetone; 2-propanone; Propanone; Dimethyl ketone; Methyl ketone; Dimethylformaldehyde;

Preparation of acetone by dry distillation of calcium acetate:

Preparation of acetone by dry distillation of calcium acetate

Preparation of acetone by dry distillation of calcium acetate

100 g of anhydrous calcium or barium acetate are distilled from a metal retort attached to a long condenser, some dry iron turnings being previously mixed with the salt to distribute the heat. When no more liquid distils, the distillate is shaken for 5 hours with three volumes of saturated sodium bisulfite solution. The crystalline compound is filtered off, dissolved in the minimum quantity of water. Anhydrous sodium carbonate is added until the solution is alkaline, and the acetone then distilled from a water bath. The distillate is dried over calcium chloride and redistilled, the fraction 55-59° C being retained. Yield 20% theoretical (12 g) from calcium acetate; 25% theoretical (10 g) from barium acetate. Colourless mobile liquid; b.p. 56.3° C; d=0.742 g/ml; soluble in water. The distillate may also be purified by adding an equal volume of water to dissolve the acetone, dehydrating for several hours over calcium oxide under a reflux, distilling, and dehydrating further over calcium chloride.

Systematic organic chemistry, by W. M. Cumming, 92, 1937.

Preparation of acetone from acetic acid

Preparation of acetone from acetic acid

Preparation of acetone from acetic acid

About 20 g of manganese(II) carbonate are made into a thick paste with water in a basin. This is stirred with an equal bulk of pumice in small pieces, and then placed in an air oven at 110-120 ° until quite dry. When dry it is loosely packed into a combustion tube, sufficient being taken to fill rather more than half (40 cm) the length of the tube; two asbestos plugs are used to keep the layer in position. The combustion tube is then placed in a long cylindrical air bath.

A glass apparatus for the preparation of acetone

A glass apparatus for the preparation of acetone

The side tube of a distilling flask containing acetic acid is inserted through an ordinary cork in one end of the combustion tube. The other end of the combustion tube may be bent and drawn out after the fashion of an adapter, or it may be fitted with a cork and delivery tube; in either case it is connected to an apparatus for condensing the mixture of acetone and acetic acid which passes over. The air bath is heated to 120-130° C and maintained at this while the combustion tube is filled with the vapour of acetic acid by boiling the acetic acid in the distilling flask for a few minutes. The air bath is then raised to 400-450° C, i.e., until the bottom of the air bath is at a good red heat. Shields of thick asbestos paper should be placed over the air bath to conserve heat. The distillate which collects in the receivers (the second receiver should be cooled in ice) consists of acetic acid, acetone and water. If this distillate is passed a second or third time over the catalyst, the yield of acetone is increased. In this way excellent yields may be obtained. The final distillate is distilled from an apparatus on a water bath, using a thermometer and efficient condenser, collecting what distils up to 80° C; this is dried in contact with solid potassium carbonate and fractionally distilled.

Systematic organic chemistry, by W. M. Cumming, 94, 1937.

IUPAC Name

propan-2-one

InChI

InChI=1S/C3H6O/c1-3(2)4/h1-2H3

InChI Key

CSCPPACGZOOCGX-UHFFFAOYSA-N

Canonical SMILES

CC(=O)C

MeSH Synonyms

Acetone

Depositor-Supplied Synonyms

acetone, 2-propanone, propanone, Dimethyl ketone, Methyl ketone, Dimethylformaldehyde, Pyroacetic ether, Dimethylketal, propan-2-one, Chevron acetone, beta-Ketopropane, 67-64-1, Ketone propane, Aceton, Pyroacetic acid, dimethylketone, Ketone, dimethyl, Dimethyl formaldehyde, RCRA waste number U002, Acetone (natural), Ketone, dimethyl-, .beta.-Ketopropane, Caswell No. 004, Aceton [German, Dutch, Polish], RCRA waste no. U002, NSC 135802, HSDB 41, d-acetone, UNII-1364PS73AF, FEMA No. 3326, CCRIS 5953, CHEBI:15347, CSCPPACGZOOCGX-UHFFFAOYSA-N, EINECS 200-662-2, UN1090, EPA Pesticide Chemical Code 004101, NCGC00091179-01, AI3-01238, DSSTox_CID_1482, DSSTox_RID_76176, DSSTox_GSID_21482, CAS-67-64-1, dimethylcetone, isopropanal, methylketone, Dimethylketon, Propanon, Sasetone, Azeton, methyl-ketone, 2propanone, b-Ketopropane, 2-propanal, Acetone (NF), Acetone (TN), 4468-52-4, ACETONE, HPLC, ACETONE, ACS, Acetone, 99.5%, Acetone oil (Salt/Mix), ACMC-1AI6Y, AC1L18NO, Pyroacetic spirit (archaic), KSC353M9B, UN 1091 (Salt/Mix), 40289_ALDRICH, 40308_ALDRICH, Aceton (GERMAN, POLISH), CHEMBL14253, W332607_ALDRICH, W332615_ALDRICH, (CH3)2CO, 179973_ALDRICH, 24201_RIEDEL, 270725_ALDRICH, 32201_RIEDEL, 323772_ALDRICH, 34480_RIEDEL, 40289_RIEDEL, 40308_RIEDEL, 439126_ALDRICH, 534064_ALDRICH, 650501_ALDRICH, 673781_ALDRICH, WLN: 1V1, 00561_FLUKA, 34480_FLUKA, 90872_FLUKA, CTK2F3690, HMDB01659, 1364PS73AF, 24201_SIAL, 32201_SIAL, 34850_SIAL, 154598_SIAL, 179124_SIAL, 179973_SIAL, 270725_SIAL, 320110_SIAL, 323772_SIAL, 439126_SIAL, 534064_SIAL, 650501_SIAL, 673781_SIAL, Tox21_111096, Tox21_202480, c0556, LMFA12000057, NSC135802, ZINC00895111, AKOS000120890, LS-1566, NSC-135802, RL04583, RTR-022713, UN 1090, Acetone [UN1090] [Flammable liquid], Acetone [UN1090] [Flammable liquid], NCGC00260029-01, AN-41894, KB-47075, TR-022713, A0054, FT-0621799, FT-0671108, InChI=1/C3H6O/c1-3(2)4/h1-2H, 2941-EP1441224A2, 2941-EP2269975A2, 2941-EP2269977A2, 2941-EP2269986A1, 2941-EP2269988A2, 2941-EP2269989A1, 2941-EP2269990A1, 2941-EP2269992A1, 2941-EP2269993A1, 2941-EP2269994A1, 2941-EP2269995A1, 2941-EP2269997A2, 2941-EP2269999A1, 2941-EP2270000A1, 2941-EP2270004A1, 2941-EP2270006A1, 2941-EP2270009A1, 2941-EP2270010A1, 2941-EP2270011A1, 2941-EP2270012A1, 2941-EP2270013A1, 2941-EP2270014A1, 2941-EP2270015A1, 2941-EP2270016A1, 2941-EP2270113A1, 2941-EP2270114A1, 2941-EP2272517A1, 2941-EP2272537A2, 2941-EP2272813A2, 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