Cyclohexanone

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Gas phase thermochemistry data

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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

Quantity Value Units Method Reference Comment
Δfgas-231.1 ± 0.88kJ/molCmWiberg, Crocker, et al., 1991ALS
Δfgas-225.7kJ/molEqkKabo, Yursha, et al., 1988ALS
Δfgas-227.7 ± 1.9kJ/molCcbWolf, 1972ALS
Δfgas-226.3kJ/molCcbSellers and Sunner, 1962ALS
Quantity Value Units Method Reference Comment
gas335.53J/mol*KN/AKabo G.J., 1988GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
121.06298.15Kabo G.J., 1988Selected thermodynamic functions are in better agreement with experimental values of S(298.15 K) and Cp(T) than statistical values calculated by [ Thermodynamics Research Center, 1997, Andreevskii D.N., 1976]. Maximum discrepancies with functions given in [ Thermodynamics Research Center, 1997] amount to 2.5 and 5.0 J/mol*K for S(T) and Cp(T), respectively. Discrepancies with data [ Andreevskii D.N., 1976] reach 11 and 8 J/mol*K for S(T) and Cp(T), respectively.; GT
121.89300.
161.88400.
196.39500.
225.24600.
249.27700.
269.47800.
286.51900.
301.061000.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
155.20385.Shvaro O.V., 1987The experimental values of Cp(T) obtained by [ Vilcu R., 1975] seem to be not enough reliable in view of the comparison of experimental heat capacities of some alcohols and ketones measured by these authors (see [ Kabo G.J., 1995]).; GT
161.07400.
168.98420.
175.81440.
183.65460.
190.18480.

Condensed phase thermochemistry data

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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

Quantity Value Units Method Reference Comment
Δfliquid-276.1 ± 0.84kJ/molCmWiberg, Crocker, et al., 1991ALS
Δfliquid-272.6 ± 1.8kJ/molCcbWolf, 1972ALS
Δfliquid-254. ± 2.kJ/molCcbRabinovoch, Tel'noy, et al., 1962ALS
Δfliquid-271.4kJ/molCcbSellers and Sunner, 1962ALS
Quantity Value Units Method Reference Comment
Δcliquid-3517.6 ± 1.7kJ/molCcbWolf, 1972Corresponding Δfliquid = -272.58 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3536. ± 2.kJ/molCcbRabinovoch, Tel'noy, et al., 1962Corresponding Δfliquid = -254. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3518.9 ± 1.0kJ/molCcbSellers and Sunner, 1962Corresponding Δfliquid = -271.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3499. ± 0.8kJ/molCcbSkuratov, Kozina, et al., 1957At 20C; Corresponding Δfliquid = -291. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid229.03J/mol*KN/ANakamura, Suga, et al., 1980DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
177.20300.Nakamura, Suga, et al., 1980T = 13 to 300 K. Unsmoothed experimental datum for Cp at 296.40 K is 175.96 J/mol*K.; DH
200.4304.2Phillip, 1939DH
177.8290.Herz and Bloch, 1924DH

Phase change data

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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

Quantity Value Units Method Reference Comment
Tboil428. ± 2.KAVGN/AAverage of 21 out of 23 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus243. ± 10.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple245.21KN/ANakamura, Suga, et al., 1980, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Ttriple242.4KN/AWuerflinger and Kreutzenbeck, 1978Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tc664.3KN/AQuadri and Kudchadker, 1991Uncertainty assigned by TRC = 3. K; TRC
Tc653.KN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 3. K; TRC
Tc629.15KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Pc46.00barN/AQuadri and Kudchadker, 1991Uncertainty assigned by TRC = 1.00 bar; TRC
Pc40.00barN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 0.50 bar; TRC
Pc38.5035barN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2.0265 bar; TRC
Quantity Value Units Method Reference Comment
Δvap44. ± 4.kJ/molAVGN/AAverage of 7 values; Individual data points

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
320.20.020Weast and Grasselli, 1989BS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
45.130428.8N/ASvoboda, Kubes, et al., 1992Value corrected to 298.15 K.; DH
43.1358.EBTeodorescu, Barhala, et al., 2006Based on data from 343. to 427. K.; AC
44.0333.N/AAucejo, Monton, et al., 1993Based on data from 318. to 428. K.; AC
44.4 ± 0.1308.CSvoboda, Kubes, et al., 1992AC
44.0 ± 0.1313.CSvoboda, Kubes, et al., 1992AC
43.4 ± 0.1323.CSvoboda, Kubes, et al., 1992AC
43.1 ± 0.1328.CSvoboda, Kubes, et al., 1992AC
42.2 ± 0.1338.CSvoboda, Kubes, et al., 1992AC
41.8 ± 0.1343.CSvoboda, Kubes, et al., 1992AC
41.4 ± 0.1348.CSvoboda, Kubes, et al., 1992AC
42.2360.EBAmbrose and Ghiassee, 1987, 2Based on data from 345. to 458. K.; AC
41.5377.A,EBStephenson and Malanowski, 1987Based on data from 362. to 439. K. See also Meyer and Hotz, 1973.; AC
40.4410.N/ACastellari, Francesconi, et al., 1984Based on data from 395. to 426. K.; AC
40.3286.N/ARadulescu and Alexa, 1938Based on data from 273. to 298. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference
362.78 to 438.924.1033 ± 0.000991495.51 ± 0.67-63.598 ± 0.075Meyer and Hotz, 1973

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Reference Comment
49.3254.Nitta and Seki, 1948Based on data from 243. to 265. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
1.33245.2Nakamura, Suga, et al., 1980AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
38.5221.Gonthier-Vassal and Szwarc, 1998CAL
5.2242.6

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
39.22220.8Nakamura, Suga, et al., 1980, 2CAL
5.42245.2

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
8.6596220.83crystaline, IIcrystaline, INakamura, Suga, et al., 1980DH
1.3276245.21crystaline, IliquidNakamura, Suga, et al., 1980DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
39.22220.83crystaline, IIcrystaline, INakamura, Suga, et al., 1980DH
5.414245.21crystaline, IliquidNakamura, Suga, et al., 1980DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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