Acetone

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Acetone[1]
Full structural formula of acetone with dimensions
Skeletal formula of acetone
Ball-and-stick model of acetone
Space-filling model of acetone
Names
Preferred IUPAC name
Propan-2-one[7]
Other names
  • Acetone
  • Dimethyl ketone[2]
  • Dimethyl carbonyl
  • β-Ketopropane[2]
  • Propanone[3]
  • 2-Propanone[2]
  • Dimethyl formaldehyde[4]
  • Pyroacetic spirit (archaic)[5]
  • Ketone propane[6]
Identifiers
3D model (JSmol)
3DMet {{{value}}}
Beilstein Reference 635680
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.602
EC Number 200-662-2
Gmelin Reference 1466
KEGG
MeSH {{{value}}}
PubChem {{{value}}}
RTECS number AL3150000
UNII
UN number 1090
SMILES {{{value}}}
Properties
C3H6O
Molar mass 58.08 g·mol−1
Appearance Colorless liquid
Odor Pungent, irritating, floral, cucumber like
Density 0.7845 g/cm3 (25 °C)
Melting point −94.7 °C (−138.5 °F; 178.5 K)[12]
Boiling point 56.05 °C (132.89 °F; 329.20 K)[12]
Miscible
Solubility Miscible in benzene, diethyl ether, methanol, chloroform, ethanol[8]
log P -0.16[9]
Vapor pressure
  • 9.39 kPa (0 °C)
  • 30.6 kPa (25 °C)
  • 374 kPa (100 °C)
  • 2.8 MPa (200 °C)[2]
Acidity (pKa)
−33.78·10−6 cm3/mol
1.3588 (VD = 54.46)
Viscosity 0.295 mPa·s (25 °C)[8]
Structure
Trigonal planar at C2
Dihedral at C2
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

NFPA 704.svg

3
1
0
 
Explosive limits 2.6–12.8%[13]
U.S. Permissible
exposure limit (PEL)
1000 ppm (2400 mg/m3)[6]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☑Y verify (what is ☑Y☒N ?)
Infobox references

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.

Sources[change | change source]

  1. The Merck Index, 15th Ed. (2013), p. 13, Acetone Monograph 65, O'Neil: The Royal Society of Chemistry.Template:Subscription needed
  2. 2.0 2.1 2.2 2.3 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)
  3. 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.
  4. Ash, Michael; Ash, Irene (2004). Handbook of preservatives. Synapse Information Resources, Inc. p. 369. ISBN 1-890595-66-7.
  5. Myers, Richard L. (2007). The 100 Most Important Chemical Compounds: A Reference Guide. Greenwood. pp. 4–6. ISBN 978-0-313-08057-9.
  6. 6.0 6.1 "NIOSH Pocket Guide to Chemical Hazards #0260". National Institute for Occupational Safety and Health (NIOSH).
  7. 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.
  8. 8.0 8.1 Properties of substance: acetone. chemister.ru.
  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. 
  11. Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Accounts of Chemical Research 21 (12): 456–463. doi:10.1021/ar00156a004. 
  12. 12.0 12.1 Lide, David R. (ed) (2003). CRC Handbook of Chemistry and Physics, 84th Edition. CRC Press. Boca Raton, Florida; Section 3, Physical Constants of Organic Compounds.
  13. "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. Cite uses deprecated parameter |dead-url= (help)