|Molecular formula||C 3 H 6 O|
colorless liquid with a sweet odor
|External identifiers / databases|
|Molar mass||58.08 g mol −1|
0.79 g cm −3 (20 ° C)
−95 ° C
56 ° C
miscible with water and many organic solvents
1.3588 (20 ° C)
DFG / Switzerland: 500 ml m −3 or 1200 mg m −3
|As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C|
Acetone or acetone [ at͡səˈtoːn ] is the common name for the organic-chemical compound propanone or dimethyl ketone . Acetone is a colorless liquid and is used as a polar, aprotic solvent and as a starting material for many syntheses in organic chemistry. With its structural feature of the carbonyl group (> C = O), which carries two methyl groups , it is the simplest ketone .
Extraction and presentation
Acetone was first produced in 1606 by Andreas Libavius by heating lead (II) acetate . In 1661 Robert Boyle was able to win it through the dry distillation of wood. It was first described in 1610 in the Tyrocinium Chymicum by Jean Beguin . Until the middle of the 20th century, the acetone-butanol-ethanol fermentation discovered and patented by Chaim Weizmann was an important process for the production of acetone as well. The anaerobic bacterium Clostridium acetobutylicum was used for industrial production .
Here benzene and propene are first converted into isopropylbenzene ( cumene ) by a Friedel-Crafts alkylation in an acid . This then reacts with oxygen in a radical reaction to form the hydroperoxide , which decomposes to phenol and acetone during acidic processing .
This process goes back to the above-mentioned historical synthesis by Libavius in 1606.
Acetone is a colorless, low-viscosity liquid with a characteristic, slightly sweet odor, highly flammable and forms an explosive mixture with air. The boiling point at normal pressure is 56 ° C. It is miscible with water and most organic solvents in all proportions. The acetone molecule shows keto-enol tautomerism ; its pK s value is 20. acetone may be due to its polar carbonyl group with cations also form complex compounds.
The compound forms azeotropically boiling mixtures with a number of other solvents . The azeotropic compositions and boiling points can be found in the following table. No azeotropes are formed with water , ethanol , 1-propanol , 2-propanol , n-butanol , benzene , toluene , ethylbenzene , diethyl ether , ethyl acetate and acetonitrile .
|Azeotropes with various solvents|
|solvent||n -pentane||n -hexane||n -heptane||Cyclohexane||Methanol||chloroform||Carbon tetrachloride||Diisopropyl ether||Methyl acetate|
|Content of acetone||in%||21st||59||90||67||88||22nd||89||61||50|
|boiling point||in ° C||32||50||56||53||55||64||56||54||55|
According to Antoine, the vapor pressure function results from log 10 (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.42448, B = 1312.253 and C = −32.445 in the temperature range from 259.2 to 507.6 K.
|Standard enthalpy of formation||Δ f H 0 liquid
Δ f H 0 gas
|−249.4 kJ mol −1
−218.5 kJ mol −1
|as a liquid
as a gas
|Enthalpy of combustion||Δ c H 0 gas||−1821.4 kJ mol −1|
|Heat capacity||c p||125.45 J mol −1 K −1 (25 ° C)
2.16 J g −1 K −1 (25 ° C)
75.02 J mol −1 K −1 (25 ° C )
1.29 J g −1 K −1 (25 ° C)
|as a liquid
as a gas
|Critical temperature||T c||508.15K|
|Critical pressure||p c||47.582 bar|
|Critical density||ρ c||4.63 mol·l −1|
|Acentric factor||ω c||0.30653|
|Enthalpy of fusion||Δ f H||5.72 kJ mol −1||at the melting point|
|Enthalpy of evaporation||Δ V H||29.1 kJ mol −1||at normal pressure boiling point|
The temperature dependence of the evaporation enthalpy can be calculated according to the equation Δ V H 0 = A e (−βT r ) (1 − T r ) β (Δ V H 0 in kJ / mol, T r = (T / T c ) reduced temperature ) with A = 46.95 kJ / mol, β = 0.2826 and T c = 508.2 K in the temperature range between 298 K and 363 K. The specific heat capacity can be calculated in the temperature range between 5 ° C and 50 ° C via a linear function with c p = 1.337 + 2.7752 · 10 −3 · T (with c p in kJ · kg −1 · K −1 and T in K) can be estimated.
Vapor pressure function of acetone
Temperature dependence of the heat of vaporization of acetone
Specific heat capacity of acetone
Acetone forms highly flammable vapor-air mixtures. The compound has a flash point below −20 ° C. The explosion range is between 2.5 vol.% (60 g / m³) as the lower explosion limit (LEL) and 14.3 vol.% (345 g / m³) as the upper explosion limit (UEL). A correlation of the explosion limits with the vapor pressure function results in a lower explosion point of −23 ° C and an upper explosion point of 8 ° C. The explosion limits are pressure dependent. A reduction in pressure leads to a reduction in the explosion area. The lower explosion limit changes only slightly up to a pressure of 100 mbar and only increases at pressures below 100 mbar. The upper explosion limit decreases analogously with falling pressure.
|Explosion limits under reduced pressure (measured at 100 ° C)|
|Lower explosion limit (LEL)||in% by volume||2.2||2.2||2.3||2.3||2.4||2.4||2.5||2.6||2.7||3.6||5.0|
|in g m −3||53||53||53||55||57||58||59||61||63||86||119|
|Upper explosion limit (UEL)||in% by volume||14.3||14.0||13.7||13.4||13.2||13.1||13.1||13.1||12.5||10.3||9.0|
|in g m −3||345||338||331||324||319||316||316||316||302||249||217|
|Maximum explosion pressure under reduced pressure|
|Maximum explosion pressure (in bar)||at 20 ° C||9.3||7.5||5.5||3.6||2.7||1.8||0.8|
|at 100 ° C||7.4||4.5|
The maximum explosion pressure is 9.7 bar. As the temperature rises and the outlet pressure falls, the maximum explosion pressure falls. The limit gap width was determined to be 1.04 mm (50 ° C). This results in an assignment to explosion group IIA. With a minimum ignition energy of 1.15 mJ, vapor-air mixtures are extremely ignitable. The ignition temperature is 535 ° C. The substance therefore falls into temperature class T1. A sharp drop in the ignition temperature is observed under increased pressure. The electrical conductivity is rather low at 4.9 · 10 −7 S · m −1 .
|Ignition temperatures under increased pressure|
|Ignition temperature||in ° C||535||345||290||265||250|
Iodination of acetone
A special reaction here is the iodination of acetone as a classic example of pseudo-zero order reaction kinetics . Since only the enol form can be iodinated, but acetone is almost 100% ketone, the 2-propenol concentration during the reaction can be regarded as constant. Its C = C double bond reacts with iodine , splitting off an iodide ion to form a mesomeric cation, which then transfers a proton to an iodide ion.
The establishment of the keto-enol equilibrium is acid (and also base) catalyzed. The iodination is therefore greatly accelerated by the resulting hydrogen iodide ( autocatalysis ).
When adding base, however, the iodoform reaction takes place:
Formation of dibenzalacetone
Also benzalaniline be synthesized - it reacts aniline with the at-in alkaline solution acetone elimination of water to Schiff base ( azomethine ). Both dibenzalacetone and benzalaniline are valuable substances because they have very reactive double bonds that can be attacked by nucleophiles .
Formation of diacetone alcohol
If two acetone molecules are allowed to dimerize in an aldol-like manner under the influence of basic reagents, diacetone alcohol is formed :
Formation of acetone peroxide
Reaction with chloroform
Acetone and chloroform must not be mixed in higher concentrations because a very violent reaction occurs in the presence of traces of alkaline substances, producing 1,1,1-trichloro-2-methyl-2-propanol . For this reason, too, chlorinated and non-chlorinated solvent waste should be collected separately in the laboratory.
Acetone is the starting material for numerous syntheses in the chemical industry. It is mainly used to manufacture polymethyl methacrylate (PMMA), colloquially known as acrylic glass or plexiglass. To do this, the acetone is first converted into acetone cyanohydrin by adding hydrocyanic acid , which easily splits off water in an acidic environment ( mesomeric stabilization of the double bond due to conjugation to the triple bond of the nitrile group). The resulting 2-methylpropenenitrile is converted to methyl methacrylate by adding a mixture of concentrated sulfuric acid and methanol , which is polymerized to acrylic glass in a further step.
Acetone is also used in small quantities as a useful solvent for resins , fats and oils, rosin , cellulose acetate, as well as nail polish remover and plastic glue. It is also used to remove contamination caused by construction foam, for example when cleaning PU foam guns. It dissolves many times its volume in ethyne (acetylene).
Acetone is a ketone body formed in the liver that cannot be metabolized to any significant extent. It is therefore released through the lungs or, in exceptional cases , through the urine ( acetonuria , a symptom of diabetes mellitus ). Other ketone bodies are acetoacetic acid and 3-hydroxybutanoic acid . These can be processed in the metabolism and are involved in providing energy for the muscles.
Acetone causes dryness on the skin as it degreases the skin. Therefore, you should grease the affected areas after contact. Inhalation of larger doses causes bronchial irritation, tiredness and headache. Very high doses have a narcotic effect .
The physical properties are slightly different from the non-deuterated compound:
- Melting point: -93.8 ° C
- Boiling point: 55.5 ° C
- Density: 0.872 g / ml (25 ° C)
- Refractive index: 1.355 (20 ° C)
- Entry for Acetone in the Consumer Product Information Database
- Entry on ACETONE in the CosIng database of the EU Commission, accessed on February 16, 2020.
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- External identifiers of or database links for Deuterated Acetone : CAS number: 666-52-4, EC number: 211-563-9, ECHA InfoCard: 100.010.514 , PubChem : 522220 , ChemSpider : 455535 , Wikidata : Q1032873 .
- Acetone-d6 data sheet from Sigma-Aldrich , accessed on August 31, 2019 ( PDF ).
- Compared to 0.791 g / ml (25 ° C) for the nondeuterated compound. Acetone data sheet from Sigma-Aldrich , accessed on August 31, 2019 ( PDF ).