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Cyclohexanol

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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
DRB - Donald R. Burgess, Jr.
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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil433. ± 3.KAVGN/AAverage of 20 out of 21 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus296. ± 5.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple299.09KN/AAdachi, Suga, et al., 1968Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple297.0KN/AKelley, 1929Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc645. ± 20.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Pc40.27atmN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 1.48 atm; derived from fit of obs. vapor pressure; TRC
Pc43.43atmN/AWilson, Wilson, et al., 1996Uncertainty assigned by TRC = 0.25 atm; TRC
Pc42.0 ± 0.5atmN/AGude and Teja, 1995 
Pc42.04atmN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 0.49 atm; TRC
Pc37.0000atmN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 1.5000 atm; TRC
Quantity Value Units Method Reference Comment
rhoc3.00mol/lN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 0.10 mol/l; TRC
Quantity Value Units Method Reference Comment
Deltavap14.8 ± 0.3kcal/molAVGN/AAverage of 10 out of 11 values; Individual data points

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
14.4337.N/ASteyer and Sundmacher, 2004Based on data from 322. - 433. K.; AC
11.9405.N/ASwiatek and Malanowski, 2002Based on data from 390. - 430. K.; AC
14.6 ± 0.1308.GSVerevkin, 1998Based on data from 288. - 328. K.; AC
13.1365.EBAmbrose and Ghiassee, 1987, 2Based on data from 350. - 456. K.; AC
14.3333.AStephenson and Malanowski, 1987Based on data from 318. - 434. K.; AC
15.0315.AStephenson and Malanowski, 1987Based on data from 300. - 434. K.; AC
11.8418.N/ACastellari, Francesconi, et al., 1984Based on data from 404. - 432. K.; AC
14.0318.N/ASipowska and Wieczorek, 1984Based on data from 303. - 373. K.; AC
14.4309.N/ACabani, Conti, et al., 1975Based on data from 299. - 319. K.; AC
12.6382.N/ANovák, Matous, et al., 1960Based on data from 367. - 433. K. See also Novák, Matous, et al., 1960, 2.; AC
13.1322.N/AThomson, 1946Based on data from 307. - 422. K.; AC
10.86431.7VMathews and Fehlandt, 1931ALS

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
366.88 - 433.93.07506777.363-182.037Novak, Matous, et al., 1960Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
14.5285.AStephenson and Malanowski, 1987Based on data from 272. - 298. K. See also Nitta and Seki, 1948.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
0.413298.2DSCSingh and Murthy, 2009AC
0.41297.N/APingel, Poser, et al., 1984See also Adachi, Suga, et al., 1968, 2 and Domalski and Hearing, 1996.; AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
7.443263.5Domalski and Hearing, 1996CAL
1.37297.

Enthalpy of phase transition

DeltaHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.09044220.9crystaline, IIIcrystaline, IIMayer, Rachwalska, et al., 1990DH
2.060244.5crystaline, IIIcrystaline, IMayer, Rachwalska, et al., 1990DH
2.070264.86crystaline, IIcrystaline, IMayer, Rachwalska, et al., 1990DH
0.4316297.92crystaline, IliquidMayer, Rachwalska, et al., 1990DH
2.065244.8crystaline, IIIcrystaline, IAdachi, Suga, et al., 1968, 2DH
2.110265.50crystaline, IIcrystaline, IAdachi, Suga, et al., 1968, 2DH
0.4261299.09crystaline, IliquidAdachi, Suga, et al., 1968, 2DH
1.961263.5crystaline, IIcrystaline, IKelley, 1929, 2Excess enthalpy over extrapolated heat capacity curves.; DH
0.4061297.0crystaline, IliquidKelley, 1929, 2Tm is 23.87°C from 16RIC/SHI.; DH

Entropy of phase transition

DeltaStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.4094220.9crystaline, IIIcrystaline, IIMayer, Rachwalska, et al., 1990DH
8.44244.5crystaline, IIIcrystaline, IMayer, Rachwalska, et al., 1990DH
7.815264.86crystaline, IIcrystaline, IMayer, Rachwalska, et al., 1990DH
1.45297.92crystaline, IliquidMayer, Rachwalska, et al., 1990DH
8.435244.8crystaline, IIIcrystaline, IAdachi, Suga, et al., 1968, 2DH
7.947265.50crystaline, IIcrystaline, IAdachi, Suga, et al., 1968, 2DH
1.42299.09crystaline, IliquidAdachi, Suga, et al., 1968, 2DH
7.443263.5crystaline, IIcrystaline, IKelley, 1929, 2Excess; DH
1.37297.0crystaline, IliquidKelley, 1929, 2Tm; DH

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, Phase change data, Notes

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

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, 5, 1073, https://doi.org/10.1246/bcsj.41.1073 . [all data]

Kelley, 1929
Kelley, K.K., Cyclohexanol and the third law of thermodynamics, J. Am. Chem. Soc., 1929, 51, 1400-6. [all data]

Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturted Line, Measurements for Cyclohexanol, 2-Cyclohexen-1-one, 1,2-Dichloropropane, 1,4-Di-tert-butylbenzene, (±)-2-Ethylhexanoic Acid, 1-(m, J. Chem. Eng. Data, 1997, 42, 1021-36. [all data]

Wilson, Wilson, et al., 1996
Wilson, L.C.; Wilson, H.L.; Wilding, W.V.; Wilson, G.M., Critical Point Measurements for Fourteen Compounds by a Static Method and a Flow Method, J. Chem. Eng. Data, 1996, 41, 1252-4. [all data]

Gude and Teja, 1995
Gude, M.; Teja, A.S., Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols, J. Chem. Eng. Data, 1995, 40, 1025-1036. [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]

Steyer and Sundmacher, 2004
Steyer, Frank; Sundmacher, Kai, VLE and LLE Data for the System Cyclohexane + Cyclohexene + Water + Cyclohexanol, J. Chem. Eng. Data, 2004, 49, 6, 1675-1681, https://doi.org/10.1021/je049902w . [all data]

Swiatek and Malanowski, 2002
Swiatek, Barbara E.; Malanowski, Stanislaw K., Vapor-Liquid Equilibrium in m -Xylene + Cyclohexanol at 19.99 and 94.93 kPa, J. Chem. Eng. Data, 2002, 47, 3, 478-481, https://doi.org/10.1021/je010246z . [all data]

Verevkin, 1998
Verevkin, Sergey P., Thermochemistry of phenols: experimental standard molar enthalpies of formation of 2-phenylphenol, 4-phenylphenol, 2,6-diphenylphenol, and 2,2´- and 4,4´-dihydroxybiphenyl, The Journal of Chemical Thermodynamics, 1998, 30, 3, 389-396, https://doi.org/10.1006/jcht.1997.0316 . [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]

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]

Sipowska and Wieczorek, 1984
Sipowska, Jadwiga T.; Wieczorek, Stefan A., Vapour pressures and excess Gibbs free energies of (cyclohexanol + n-heptane) between 303.147 and 373.278 K, The Journal of Chemical Thermodynamics, 1984, 16, 7, 693-699, https://doi.org/10.1016/0021-9614(84)90051-X . [all data]

Cabani, Conti, et al., 1975
Cabani, Sergio; Conti, G.; Mollica, V.; Lepori, L., Thermodynamic study of dilute aqueous solutions of organic compounds. Part 4.---Cyclic and straight chain secondary alcohols, J. Chem. Soc., Faraday Trans. 1, 1975, 71, 0, 1943, https://doi.org/10.1039/f19757101943 . [all data]

Novák, Matous, et al., 1960
Novák, J.; Matous, J.; Pick, J., Gleichgewicht flüssigkeit-dampf XXIV. Gleichgewicht flüssigkeit-dampf im system cyclohexylamin-cyclohexanol-anilin, Collect. Czech. Chem. Commun., 1960, 25, 9, 2405-2413, https://doi.org/10.1135/cccc19602405 . [all data]

Novák, Matous, et al., 1960, 2
Novák, J.; Matous, J.; Pick, J., Dampfdruck des cyclohexanols und des cyclohexylamins, Collect. Czech. Chem. Commun., 1960, 25, 2, 583-585, https://doi.org/10.1135/cccc19600583 . [all data]

Thomson, 1946
Thomson, George Wm., The Antoine Equation for Vapor-pressure Data., Chem. Rev., 1946, 38, 1, 1-39, https://doi.org/10.1021/cr60119a001 . [all data]

Mathews and Fehlandt, 1931
Mathews, J.H.; Fehlandt, P.R., The heats of vaporization of some organic compounds, J. Am. Chem. Soc., 1931, 53, 3212-32. [all data]

Novak, Matous, et al., 1960
Novak, J.; Matous, J.; Pick, J., Dampfdruck des Cyclohexanols und des Cyclohexylamins, Collect. Czech. Chem. Commun., 1960, 25, 2, 583-584, https://doi.org/10.1135/cccc19600583 . [all data]

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

Singh and Murthy, 2009
Singh, Lokendra P.; Murthy, S.S.N., Dielectric and calorimetric investigation of an unusual two-component plastic crystal: cyclohexanol-neopentylglycol, Phys. Chem. Chem. Phys., 2009, 11, 25, 5110, https://doi.org/10.1039/b817964f . [all data]

Pingel, Poser, et al., 1984
Pingel, Norbert; Poser, Uwe; Würflinger, Albert, Dielectric measurements at high pressures and low temperatures. Part 6.---Dielectric and thermodynamic properties of cyclohexanol, J. Chem. Soc., Faraday Trans. 1, 1984, 80, 11, 3221, https://doi.org/10.1039/f19848003221 . [all data]

Adachi, Suga, et al., 1968, 2
Adachi, K.; Suga, H.; Seki, S., Phase changes in crystalline and glassy-crystalline cyclohexanol, Bull. Chem. Soc. Japan, 1968, 41, 1073-1087. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

Kelley, 1929, 2
Kelley, K.K., Cyclohexanol and the third law of thermodynamics, J. Am. Chem. Soc., 1929, 51, 1400-1406. [all data]


Notes

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