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Cyclohexanol

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-290. ± 8.kJ/molAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
gas353.83J/mol*KN/AKabo G.J., 1988Other entropy value at 298.15 K obtained from calorimetric data is 327.69 J/mol*K [ Stull D.R., 1969].; GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
132.70298.15Kabo G.J., 1988Statistically calculated S(T) and Cp(T) values given in [ Thermodynamics Research Center, 1997] are 1-10 and 5-10 J/mol*K, respectively, lower than those of [ Kabo G.J., 1988].; GT
133.53300.
176.60400.
216.42500.
250.18600.
278.37700.
301.73800.
320.77900.
337.321000.

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
Deltafliquid-352.0 ± 0.67kJ/molCacWiberg, Wasserman, et al., 1985Trifluoroacetolysis; ALS
Deltafliquid-350. ± 2.kJ/molCcbRabinovoch, Tel'noy, et al., 1962ALS
Deltafliquid-347.4 ± 2.2kJ/molCcbSellers and Sunner, 1962Reanalyzed by Cox and Pilcher, 1970, Original value = -348.2 kJ/mol; ALS
Deltafliquid-349.2 ± 0.2kJ/molCcbParks, Mosley, et al., 1950ALS
Deltafliquid-359.2kJ/molCcbKelley, 1929ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3730. ± 20.kJ/molAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
liquid203.87J/mol*KN/AAdachi, Suga, et al., 1968DH
liquid199.6J/mol*KN/AKelley, 1929Average of values derived from measurements on both low and high temperature crystal forms down to 13 K, plus entropy of transition and fusion. Debye extrapolation below 13.5 K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
214.06298.15Mayer, Rachwalska, et al., 1990T = 170 to 320 K. Cp(liq) = -2223.2606 + 22.0059595T - 0.0691686793T2 + 0.0000763592T3 J/mol*K (298 to 320 K). Cp value caluculated from equation.; DH
209.99298.15Caceres-Alonso, Costas, et al., 1988DH
220.1298.Conti, Gianni, et al., 1976DH
212.297.95Petit and TerMinassian, 1974T = 297 to 428 K. Value is unsmoothed experimental datum.; DH
213.59300.Adachi, Suga, et al., 1968T = 14 to 320 K.; DH
202.5305.1Phillip, 1939DH
209.03298.15Kelley, 1929T = 13 to 300 K. Value is unsmoothed experimental datum.; DH
174.9290.Herz and Bloch, 1924DH

Reaction 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

Cyclohexanone + Hydrogen = Cyclohexanol

By formula: C6H10O + H2 = C6H12O

Quantity Value Units Method Reference Comment
Deltar-75.86 ± 0.50kJ/molCmWiberg, Crocker, et al., 1991liquid phase
Deltar-63.51 ± 0.63kJ/molChydConn, Kistiakowsky, et al., 1939gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -64.5 ± 0.3 kJ/mol; At 355 K

Cyclohexanol + Acetic acid, trifluoro-, anhydride = Acetic acid, trifluoro-, cyclohexyl ester + Trifluoroacetic acid

By formula: C6H12O + C4F6O3 = C8H11F3O2 + C2HF3O2

Quantity Value Units Method Reference Comment
Deltar-90.06 ± 0.15kJ/molCacWiberg, Wasserman, et al., 1985liquid phase; Trifluoroacetolysis

Cyclohexanol = Cyclohexanone + Hydrogen

By formula: C6H12O = C6H10O + H2

Quantity Value Units Method Reference Comment
Deltar63.4 ± 2.3kJ/molEqkKabo, Yursha, et al., 1988gas phase; Dehydrogenation

Cyclohexanol + Acetone = Cyclohexanone + Isopropyl Alcohol

By formula: C6H12O + C3H6O = C6H10O + C3H8O

Quantity Value Units Method Reference Comment
Deltar9.9 ± 1.9kJ/molEqkFedoseenko, Yursha, et al., 1983gas phase; At 503 K

Cyclohexanol = Cyclohexane + Hydrogen

By formula: C6H12O = C6H12 + H2

Quantity Value Units Method Reference Comment
Deltar63.4 ± 2.3kJ/molEqkFedoseenko, Yursha, et al., 1983gas phase; At 502 K

Cyclohexanone + Cyclopentanol = Cyclohexanol + Cyclopentanone

By formula: C6H10O + C5H10O = C6H12O + C5H8O

Quantity Value Units Method Reference Comment
Deltar-11.6 ± 1.7kJ/molEqkFedoseenko, Yursha, et al., 1984gas phase

Cyclohexanone + Isopropyl Alcohol = Cyclohexanol + Acetone

By formula: C6H10O + C3H8O = C6H12O + C3H6O

Quantity Value Units Method Reference Comment
Deltar-9.9 ± 1.9kJ/molEqkKabo, Yursha, et al., 1988gas phase

References

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

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

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

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [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]

Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A., Enthalpies of hydration of alkenes. 3. Cycloalkenes, J. Am. Chem. Soc., 1985, 107, 6019-6022. [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]

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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Parks, Mosley, et al., 1950
Parks, G.S.; Mosley, J.R.; Peterson, P.V., Jr., Heats of combustion and formation of some organic compounds containing oxygen, J. Chem. Phys., 1950, 18, 152. [all data]

Kelley, 1929
Kelley, K.K., Cyclohexanol and the third law of thermodynamics, J. Am. Chem. Soc., 1929, 51, 1400-1406. [all data]

Adachi, Suga, et al., 1968
Adachi, K.; Suga, H.; Seki, S., Phase changes in crystalline and glassy-crystalline cyclohexanol, Bull. Chem. Soc. Japan, 1968, 41, 1073-1087. [all data]

Mayer, Rachwalska, et al., 1990
Mayer, J.; Rachwalska, M.; Sciesinska, E.; Sciesinski, J., On the polymorphism of solid cyclohexanol by adiabatic calorimetry and far infrared methods, J. Phys.(Paris), 1990, 51(9), 857-867. [all data]

Caceres-Alonso, Costas, et al., 1988
Caceres-Alonso, M.; Costas, M.; Andreoli-Ball, L.; Patterson, D., Steric effects on the self-association of branched and cyclic alcohols in inert solvents. Apparent heat capacities of secondary and tertiary alcohols in hydrocarbons, Can. J. Chem., 1988, 66, 989-998. [all data]

Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M., Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C, Chim. Ind. (Milan), 1976, 58, 225. [all data]

Petit and TerMinassian, 1974
Petit, J.C.; TerMinassian, L., Measurements of (dV/dT)p, (dV/dP)T, and (dH/dT)p by flux calorimetry, J. Chem. Thermodynam., 1974, 6, 1139-1152. [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]

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]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [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]

Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions, Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [all data]

Fedoseenko, Yursha, et al., 1984
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium of cyclopentanol dehydrogenation and hydrogen disproportionation in the cyclopentanol-cyclohexanone system, Dokl. Akad. Nauk BSSR, 1984, 28, 1109-1112. [all data]


Notes

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