Acetone

Acetone
	Preferred IUPAC name Propan-2-one
Other names	Acetone; Dimethyl ketone; Dimethyl carbonyl; β-Ketopropane; Propanone; 2-Propanone; Dimethyl formaldehyde; Pyroacetic spirit (archaic); Ketone propane;
Identifiers
CAS number	67-64-1
PubChem	180
EC number	200-662-2
KEGG	D02311
MeSH	Acetone
ChEBI	CHEBI:15347
RTECS number	AL3150000
SMILES	CC(=O)C
	InChI
Beilstein Reference	635680
Gmelin Reference	1466
3DMet	B00058
Properties
Molecular formula	C3H6O
Molar mass	58.07 g mol-1
Appearance	Colorless liquid
Odor	Pungent, irritating, floral, cucumber like
Density	0.7845 g/cm3 (25 °C)
Melting point	−94.7 °C, 178 K, -138 °F
Boiling point
Solubility in water	Miscible
Solubility	Miscible in benzene, diethyl ether, methanol, chloroform, ethanol
log P	-0.16
Vapor pressure	9.39 kPa (0 °C); 30.6 kPa (25 °C); 374 kPa (100 °C); 2.8 MPa (200 °C);
Acidity (pKa)	19.16 (H2O); 26.5 (DMSO);
Magnetic susceptibility (χ)	−33.78·10−6 cm3/mol
Refractive index (nD)	1.3588 (VD = 54.46)
Viscosity	0.295 mPa·s (25 °C)
Structure
Coordination; geometry	Trigonal planar at C2
Molecular shape	Dihedral at C2
Dipole moment	2.91 D
Thermochemistry
Std enthalpy of; formation ΔfHo298	(−250.03) – (−248.77) kJ/mol
Std enthalpy of; combustion ΔcHo298	−1.772 MJ/mol
Standard molar; entropy So298	200.4 J/(mol·K)
Specific heat capacity, C	125.45 J/(mol·K)
Hazards
NFPA 704	3 1 0
Explosive limits	2.6–12.8%
U.S. Permissible; exposure limit (PEL)	1000 ppm (2400 mg/m3)
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Acetone, or propanone, is an organic compound with the chemical formula (CH3)2CO. This clear, mobile, easy-to-burn liquid is the simplest example of the ketones. Acetone can be mixed with water. It is an important solvent, often to clean things in the laboratory. Common uses of acetone in the home are as the active ingredient in nail polish remover and as paint thinner. It is a common building block in organic chemistry.

Acetone Media

Overview of the cumene process
Keto-Enol-Tautomerie von Aceton
Structure of possible acetone polymer

Sources

↑ The Merck Index, 15th Ed. (2013), p. 13, Acetone Monograph 65, O'Neil: The Royal Society of Chemistry.(subscription needed)
↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 723. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
↑ ^3.0 ^3.1 ^3.2 ^3.3 Acetone in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-11)
↑ Klamt, Andreas (2005). COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design. Elsevier. pp. 92–94. ISBN 978-0-444-51994-8.
↑ Ash, Michael; Ash, Irene (2004). Handbook of preservatives. Synapse Information Resources, Inc. p. 369. ISBN 1-890595-66-7.
↑ Myers, Richard L. (2007). The 100 Most Important Chemical Compounds: A Reference Guide. Greenwood. pp. 4–6. ISBN 978-0-313-08057-9.
↑ ^7.0 ^7.1 NIOSH Pocket Guide to Chemical Hazards. "#0260". National Institute for Occupational Safety and Health (NIOSH).
↑ ^8.0 ^8.1 Properties of substance: acetone. chemister.ru.
↑ "acetone". ChemSrc. Retrieved 2018-04-13.
↑ Chiang, Yvonne; Kresge, A. Jerry; Tang, Yui S.; Wirz, Jakob (1984). "The pKa and keto-enol equilibrium constant of acetone in aqueous solution". Journal of the American Chemical Society. 106 (2): 460–462. doi:10.1021/ja00314a055.
↑ Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Accounts of Chemical Research. 21 (12): 456–463. doi:10.1021/ar00156a004. S2CID 26624076.
↑ "Working with modern hydrocarbon and oxygenated solvents: a guide to flammability". American Chemistry Council Solvents Industry Group. January 2008. p. 7. Archived from the original on 2009-06-01.

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[1] The Merck Index, 15th Ed. (2013), p. 13, Acetone Monograph 65, O'Neil: The Royal Society of Chemistry.(subscription needed)

[iupac2013-2] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 723. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[nist-3] 3.0 ^3.1 ^3.2 ^3.3 Acetone in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-11)

[4] Klamt, Andreas (2005). COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design. Elsevier. pp. 92–94. ISBN 978-0-444-51994-8.

[5] Ash, Michael; Ash, Irene (2004). Handbook of preservatives. Synapse Information Resources, Inc. p. 369. ISBN 1-890595-66-7.

[6] Myers, Richard L. (2007). The 100 Most Important Chemical Compounds: A Reference Guide. Greenwood. pp. 4–6. ISBN 978-0-313-08057-9.

[NIOSH-7] 7.0 ^7.1 NIOSH Pocket Guide to Chemical Hazards. "#0260". National Institute for Occupational Safety and Health (NIOSH).

[chemister-8] 8.0 ^8.1 Properties of substance: acetone. chemister.ru.

[chemsrc-9] "acetone". ChemSrc. Retrieved 2018-04-13.

[10] Chiang, Yvonne; Kresge, A. Jerry; Tang, Yui S.; Wirz, Jakob (1984). "The pKa and keto-enol equilibrium constant of acetone in aqueous solution". Journal of the American Chemical Society. 106 (2): 460–462. doi:10.1021/ja00314a055.

[Bordwell-11] Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Accounts of Chemical Research. 21 (12): 456–463. doi:10.1021/ar00156a004. S2CID 26624076.

[12] "Working with modern hydrocarbon and oxygenated solvents: a guide to flammability". American Chemistry Council Solvents Industry Group. January 2008. p. 7. Archived from the original on 2009-06-01.

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