Acetone

Not to be confused with Acetoin.
For the musical instrument company, see Ace Tone.
For other uses, see Acetone (disambiguation).
Acetone[1]
Full structural formula of acetone with dimensions
Full structural formula of acetone with dimensions
Skeletal formula of acetone
Skeletal formula of acetone
Ball-and-stick model of acetone
Ball-and-stick model of acetone
Space-filling model of acetone
Space-filling model of acetone
Sample of acetone
Names
IUPAC name
Acetone[7]
Preferred IUPAC name
Propan-2-one[8]
Systematic IUPAC name
2-Propanone
Other names
  • Acetonum (Latin pronunciation: [aˈkeːtonum])
  • Dimethyl ketone[2]
  • Dimethyl carbonyl
  • Ketone propane[3]
  • β-Ketopropane[2]
  • Propanone[4]
  • 2-Propanone[2]
  • Pyroacetic spirit (archaic)[5]
  • Spirit of Saturn (archaic)[6]
Identifiers
3D model (JSmol)
3DMet
635680
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.602 Edit this at Wikidata
EC Number
  • 200-662-2
1466
KEGG
MeSH Acetone
RTECS number
  • AL3150000
UNII
UN number 1090
  • InChI=1S/C3H6O/c1-3(2)4/h1-2H3 checkY
    Key: CSCPPACGZOOCGX-UHFFFAOYSA-N checkY
  • InChI=1/C3H6O/c1-3(2)4/h1-2H3
    Key: CSCPPACGZOOCGX-UHFFFAOYAF
  • CC(=O)C
Properties
C3H6O
Molar mass 58.080 g·mol−1
Appearance Colourless liquid
Odor Pungent, fruity[9]
Density 0.7845 g/cm3 (25 °C)[10]
Melting point −94.9 °C (−138.8 °F; 178.2 K)[10]
Boiling point 56.08 °C (132.94 °F; 329.23 K)[10]
Miscible[10]
Solubility Miscible in benzene, diethyl ether, methanol, chloroform, ethanol[10]
log P −0.24[11]
Vapor pressure
  • 9.39 kPa (0 °C)
  • 30.6 kPa (25 °C)
  • 374 kPa (100 °C)
  • 2.8 MPa (200 °C)[2]
Acidity (pKa)
−33.8·10−6 cm3/mol[14]
Thermal conductivity 0.161 W/(m·K) (25 °C)[15]
1.3588 (20 °C)[10]
Viscosity 0.306 mPa·s (25 °C)[16]
Structure
Trigonal planar at C2
Dihedral at C2
2.88 D[17]
Thermochemistry[18]
126.3 J/(mol·K)
199.8 J/(mol·K)
−248.4 kJ/mol
−1.79 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly flammable
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
Danger
H225, H302, H319, H336, H373
P210, P235, P260, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point −20 °C (−4 °F; 253 K)[19]
465[19] °C (869 °F; 738 K)
Explosive limits 2.5–12.8%[19]
250 ppm[20] (STEL), 500 ppm[20] (C)
Lethal dose or concentration (LD, LC):
  • 5800 mg/kg (rat, oral)
  • 3000 mg/kg (mouse, oral)
  • 5340 mg/kg (rabbit, oral)[21]
20,702 ppm (rat, 8 h)[21]
45,455 ppm (mouse, 1 h)[21]
NIOSH (US health exposure limits):
PEL (Permissible)
 1000 ppm (2400 mg/m3)[3]
REL (Recommended)
 TWA 250 ppm (590 mg/m3)[3]
IDLH (Immediate danger)
 2500 ppm[3]
Related compounds
Related compounds
Supplementary data page
Acetone (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Acetone (2-propanone or dimethyl ketone) is an organic compound with the formula (CH3)2CO.[22] It is the simplest and smallest ketone (>C=O). It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odour, very reminiscent of the smell of pear drops.

Acetone is miscible with water and serves as an important organic solvent in industry, home, and laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and for production of methyl methacrylate and bisphenol A, which are precursors to widely used plastics.[23][24] It is a common building block in organic chemistry. It serves as a solvent in household products such as nail polish remover and paint thinner. It has volatile organic compound (VOC)-exempt status in the United States.[25]

Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with diabetic ketoacidosis produce it in larger amounts. Ketogenic diets that increase ketone bodies (acetone, β-hydroxybutyric acid and acetoacetic acid) in the blood are used to counter epileptic attacks in children who suffer from refractory epilepsy.[26]

  1. ^ The Merck Index, 15th Ed. (2013), p. 13, Acetone Monograph 65, O'Neil: The Royal Society of Chemistry.(subscription required)
  2. ^ a b c d 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)
  3. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0004". National Institute for Occupational Safety and Health (NIOSH).
  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. ^ Myers, Richard L. (2007). The 100 Most Important Chemical Compounds: A Reference Guide. Greenwood. pp. 4–6. ISBN 978-0-313-08057-9.
  6. ^ Cite error: The named reference gorman1962 was invoked but never defined (see the help page).
  7. ^ ChemSpider lists 'acetone' as a valid, expert-verified name for what would systematically be called 'propan-2-one'.
  8. ^ 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.
  9. ^ Cite error: The named reference smell was invoked but never defined (see the help page).
  10. ^ a b c d e f Haynes, p. 3.4
  11. ^ Haynes, p. 5.173
  12. ^ 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.
  13. ^ Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Accounts of Chemical Research. 21 (12): 456–463. doi:10.1021/ar00156a004. S2CID 26624076.
  14. ^ Haynes, p. 3.576
  15. ^ Haynes, p. 6.254
  16. ^ Haynes, p. 6.243
  17. ^ Haynes, p. 9.60
  18. ^ Haynes, pp. 5.3, 5.67
  19. ^ a b c Haynes, p. 15.13
  20. ^ a b Haynes, p. 16.34
  21. ^ a b c "Acetone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  22. ^ Allen, P .W.; Bowen, H. J. M.; Sutton, L. E.; Bastiansen, O. (1952). "The molecular structure of acetone". Transactions of the Faraday Society. 48: 991. doi:10.1039/TF9524800991.
  23. ^ Acetone, World Petrochemicals report, January 2010
  24. ^ Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
  25. ^ "Update: U.S. EPA Exempt Volatile Organic Compounds". American Coatings Association. 2018-01-30. Archived from the original on 2021-02-08. Retrieved 2019-03-20.
  26. ^ Freeman, JM; Kossoff, EH; Hartman, AL (Mar 2007). "The ketogenic diet: one decade later". Pediatrics. 119 (3): 535–43. doi:10.1542/peds.2006-2447. PMID 17332207. S2CID 26629499.