Cyclohexanone

• Formula: C₆H₁₀O
• Molecular weight: 98.1430
• IUPAC Standard InChI: InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2 Copy

  
• IUPAC Standard InChIKey: JHIVVAPYMSGYDF-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-94-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Anon; Anone; Hexanon; Hytrol O; Nadone; Pimelic ketone; Pimelin ketone; Sextone; Ketohexamethylene; Cicloesanone; Cyclohexanon; Cykloheksanon; NCI-C55005; Rcra waste number U057; UN 1915; Cyclohexyl ketone; NSC 5711
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]

Kabo, Yursha, et al., 1988
Kabo, G.J.; Yursha, I.A.; Frenkel, M.L.; Poleshchuk, P.A.; Fedoseenko, V.I.; Ladutko, A.I., Thermodynamic properties of cyclohexanol and cyclohexanone, J. Chem. Thermodyn., 1988, 20, 429-437. [all data]

Wolf, 1972
Wolf, G., Thermochemische Untersuchungen an cyclischen Ketonen, Helv. Chim. Acta, 1972, 55, 1446-1459. [all data]

Sellers and Sunner, 1962
Sellers, P.; Sunner, S., Heats of combustion of cyclic ketones and alcohols, Acta Chem. Scand., 1962, 16, 46-52. [all data]

Kabo G.J., 1988
Kabo G.J., Thermodynamic properties of cyclohexanol and cyclohexanone, J. Chem. Thermodyn., 1988, 20, 429-437. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Andreevskii D.N., 1976
Andreevskii D.N., Thermodynamic properties of C4-C6 cyclic ketones, Zh. Prikl. Khim., 1976, 49, 1819-1823. [all data]

Shvaro O.V., 1987
Shvaro O.V., Thermodynamic properties of cyclopentanone and cyclohexanone, Inzh.-Fiz. Zh., 1987, 52, 807-812. [all data]

Vilcu R., 1975
Vilcu R., Heat capacity of cyclohexanone and 4-methylcyclohexanone in the vapor phase, Rev. Chim. (Bucharest), 1975, 26, 129-131. [all data]

Kabo G.J., 1995
Kabo G.J., Thermodynamic properties, conformation, and phase transitions of cyclopentanol, J. Chem. Thermodyn., 1995, 27, 953-967. [all data]

Rabinovoch, Tel'noy, et al., 1962
Rabinovoch, N.B.; Tel'noy, V.I.; Terman, L.M.; Kirillova, A.S.; Razuvaev, G.A., The heats of decomposition and formation of dicyclohexyl- and dimethylperoxidecarbonate, Dokl. Akad. Nauk SSSR, 1962, 143, 133-136. [all data]

Skuratov, Kozina, et al., 1957
Skuratov, S.M.; Kozina, M.L.; Shteher, S.M.; Varushyenko, R.M., The heats of combustion of several purified compounds, Thermochem. Bull. (Moscow State Univ.), March, 1957, 36-37. [all data]

Nakamura, Suga, et al., 1980
Nakamura, N.; Suga, H.; Seki, S., Calorimetric study on orientationally disordered crystals. Cyclohexene oxide and cyclohexanone, Bull. Chem. Soc. Japan, 1980, 53(10), 2755-2761. [all data]

Phillip, 1939
Phillip, N.M., Adiabatic and isothermal compressibilities of liquids, Proc. Indian Acad. Sci., 1939, A9, 109-120. [all data]

Herz and Bloch, 1924
Herz, W.; Bloch, W., Physikalisch-chemische Untersuchungen an Verbindungen der Cyklohexanreihe, Z. Phys. Chem., 1924, 110, 23-39. [all data]

Nakamura, Suga, et al., 1980, 2
Nakamura, N.; Suga, H.; Seki, S., Calorimetric study on orientationally disordered crystals. Cyclohexene oxide and cyclohexanone., Bull. Chem. Soc. Japan, 1980, 53, 10, 2755, https://doi.org/10.1246/bcsj.53.2755 . [all data]

Wuerflinger and Kreutzenbeck, 1978
Wuerflinger, A.; Kreutzenbeck, J., J. Phys. Chem. Solids, 1978, 39, 193. [all data]

Quadri and Kudchadker, 1991
Quadri, S.K.; Kudchadker, A.P., Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable esters, ketones, and ethers, J. Chem. Thermodyn., 1991, 23, 129-34. [all data]

Ambrose and Ghiassee, 1987
Ambrose, D.; Ghiassee, N.B., Vapor Pressures and Critical Temperatures and Critical Pressures of C5 and C6 Cyclic Alcohols and Ketones, J. Chem. Thermodyn., 1987, 19, 903. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Svoboda, Kubes, et al., 1992
Svoboda, V.; Kubes, V.; Basarova, P., Enthalpies of vaporization and cohesive energies of hexan-2-one, 2-methylpentan-4-one, 2,2-dimethylbutan-3-one, 2,6-dimethylheptan-4-one and cyclohexanone, J. Chem. Thermodynam., 1992, 24, 333-336. [all data]

Teodorescu, Barhala, et al., 2006
Teodorescu, Mariana; Barhala, Alexandru; Dragoescu, Dana, Isothermal (vapour+liquid) equilibria for the binary (cyclopentanone or cyclohexanone with 1,1,2,2-tetrachloroethane) systems at temperatures of (343.15, 353.15, and 363.15)K, The Journal of Chemical Thermodynamics, 2006, 38, 11, 1432-1437, https://doi.org/10.1016/j.jct.2006.01.010 . [all data]

Aucejo, Monton, et al., 1993
Aucejo, Antonio; Monton, Juan B.; Munoz, Rosa; Sanchotello, Margarita, Isobaric vapor-liquid equilibrium data for the cyclohexanone + N-methylacetamide system, J. Chem. Eng. Data, 1993, 38, 1, 160-162, https://doi.org/10.1021/je00009a039 . [all data]

Ambrose and Ghiassee, 1987, 2
Ambrose, D.; Ghiassee, N.B., Vapour pressures and critical temperatures and critical pressures of C5 and C6 cyclic alcohols and ketones, The Journal of Chemical Thermodynamics, 1987, 19, 9, 903-909, https://doi.org/10.1016/0021-9614(87)90036-X . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Meyer and Hotz, 1973
Meyer, Edwin F.; Hotz, Roger D., High-precision vapor-pressure data for eight organic compounds, J. Chem. Eng. Data, 1973, 18, 4, 359-362, https://doi.org/10.1021/je60059a008 . [all data]

Castellari, Francesconi, et al., 1984
Castellari, Carlo; Francesconi, Romolo; Comelli, Fabio, Vapor-liquid equilibriums in binary systems containing 1,3-dioxolane at isobaric conditions. 5. Binary mixtures of 1,3-dioxolane with cyclohexanone and cyclohexanol, J. Chem. Eng. Data, 1984, 29, 1, 90-93, https://doi.org/10.1021/je00035a029 . [all data]

Radulescu and Alexa, 1938
Radulescu, D.; Alexa, M., Bull. Chem. Soc. Romania, 1938, 20A, 89. [all data]

Nitta and Seki, 1948
Nitta, I.; Seki, S., J. Chem. Soc. Jpn. Pure Chem. Sect., 1948, 69, 141. [all data]

Gonthier-Vassal and Szwarc, 1998
Gonthier-Vassal, A.; Szwarc, H., Thermochim. Acta, 1998, 141. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°gas	Entropy of gas at standard conditions
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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