Cyclohexane, methyl-

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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
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Tboil374.0 ± 0.8KAVGN/AAverage of 101 out of 106 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus146.6 ± 0.4KAVGN/AAverage of 15 out of 16 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple146.58KN/ADouslin and Huffman, 1946Uncertainty assigned by TRC = 0.05 K; To = 273.16 K; TRC
Ttriple146.57KN/ADouslin and Huffman, 1946Uncertainty assigned by TRC = 0.08 K; To = 273.16 K; TRC
Quantity Value Units Method Reference Comment
Tc573. ± 2.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Pc34.8 ± 0.2barN/ADaubert, 1996 
Pc34.71barN/AKudchadker, Alani, et al., 1968Uncertainty assigned by TRC = 0.304 bar; TRC
Pc34.7768barN/AKay, 1947Uncertainty assigned by TRC = 0.0506 bar; TRC
Quantity Value Units Method Reference Comment
Vc0.369l/molN/ADaubert, 1996 
Quantity Value Units Method Reference Comment
ρc2.71 ± 0.02mol/lN/ADaubert, 1996 
ρc2.719mol/lN/AKudchadker, Alani, et al., 1968Uncertainty assigned by TRC = 0.03 mol/l; TRC
ρc2.715mol/lN/ASimon, 1957Uncertainty assigned by TRC = 0.03 mol/l; TRC
ρc2.71mol/lN/AKay, 1947Uncertainty assigned by TRC = 0.02 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap35.3 ± 0.2kJ/molAVGN/AAverage of 10 out of 11 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
31.27374.1N/AMajer and Svoboda, 1985 
33.8340.N/ASapei, Uusi-Kyyny, et al., 2010Based on data from 325. to 374. K.; AC
36.2310.N/AWu, Pividal, et al., 1991Based on data from 295. to 333. K.; AC
32.3388.AStephenson and Malanowski, 1987Based on data from 373. to 511. K.; AC
31.2516.AStephenson and Malanowski, 1987Based on data from 501. to 573. K.; AC
34.6323.AStephenson and Malanowski, 1987Based on data from 308. to 368. K. See also Valerga, 1970 and Boublik, Fried, et al., 1984.; AC
32.2353.N/AEubank, Cediel, et al., 1984AC
29.9393.N/AEubank, Cediel, et al., 1984AC
26.9433.N/AEubank, Cediel, et al., 1984AC
23.4473.N/AEubank, Cediel, et al., 1984AC
34.6 ± 0.1313.CMajer, Svoboda, et al., 1979AC
33.5 ± 0.1333.CMajer, Svoboda, et al., 1979AC
32.5 ± 0.1353.CMajer, Svoboda, et al., 1979AC
31.8374.N/ASpitzer and Pitzer, 1946AC
34.9314.MMWillingham, Taylor, et al., 1945Based on data from 299. to 375. K.; AC
36.1288.N/AStuckey and Saylor, 1940Based on data from 273. to 348. K.; AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kJ/mol) β Tc (K) Reference Comment
298. to 374.49.560.2685572.1Majer and Svoboda, 1985 

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
6.7505146.58Douslin and Huffman, 1946, 2DH
6.69146.6Domalski and Hearing, 1996AC
6.673146.2Parks and Huffman, 1930DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
46.05146.58Douslin and Huffman, 1946, 2DH
45.14146.2Parks and Huffman, 1930DH

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:


Gas phase ion energetics data

Go To: Top, 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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
IE (evaluated)9.64 ± 0.10eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
9.62 ± 0.05EIHolmes and Lossing, 1991LL
9.64EQSieck and Mautner(Meot-Ner), 1982LBLHLM
9.64 ± 0.10EVALLias, 1982LBLHLM
9.69 ± 0.15EQMautner(Meot-Ner), Sieck, et al., 1981LLK
9.76 ± 0.03PERang, Paldoia, et al., 1974LLK
9.85 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H11+10.95CH3EIPottie, Harrison, et al., 1961RDSH

References

Go To: Top, Phase change data, Gas phase ion energetics data, Notes

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

Douslin and Huffman, 1946
Douslin, D.R.; Huffman, H.M., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentane, methylcyclopentane and methylcyclohexane., J. Am. Chem. Soc., 1946, 68, 173. [all data]

Daubert, 1996
Daubert, T.E., Vapor-Liquid Critical Properties of Elements and Compounds. 5. Branched Alkanes and Cycloalkanes, J. Chem. Eng. Data, 1996, 41, 365-372. [all data]

Kudchadker, Alani, et al., 1968
Kudchadker, A.P.; Alani, G.H.; Zwolinski, B.J., The Critical Constants of Organic Substances, Chem. Rev., 1968, 68, 659. [all data]

Kay, 1947
Kay, W.B., Vapor Pressures and Saturated Liquid and Vapor DEensities of Cyclopentane, Methylcyclopentane, Ethylcyclopentane, and Methylcyclohexane, J. Am. Chem. Soc., 1947, 69, 1273-7. [all data]

Simon, 1957
Simon, M., Methods and Apparatus Used at the Bureau of Physicochemical Standards XV. Critical Constants and Straight-Line Diameters of Ten Hydrocarbons, Bull. Soc. Chim. Belg., 1957, 66, 375-81. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Sapei, Uusi-Kyyny, et al., 2010
Sapei, Erlin; Uusi-Kyyny, Petri; Keskinen, Kari I.; Alopaeus, Ville, Phase equilibria of binary systems of 3-methylthiophene with four different hydrocarbons, Fluid Phase Equilibria, 2010, 288, 1-2, 155-160, https://doi.org/10.1016/j.fluid.2009.11.004 . [all data]

Wu, Pividal, et al., 1991
Wu, Huey S.; Pividal, Katherine A.; Sandler, Stanley I., Vapor-liquid equilibria of hydrocarbons and fuel oxygenates, J. Chem. Eng. Data, 1991, 36, 4, 418-421, https://doi.org/10.1021/je00004a021 . [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]

Valerga, 1970
Valerga, Antone J., Entropy and Related Thermodynamic Properties of Tetramethylgermane, J. Chem. Phys., 1970, 52, 9, 4545, https://doi.org/10.1063/1.1673681 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Eubank, Cediel, et al., 1984
Eubank, P.T.; Cediel, L.E.; Holste, J.C.; Hall, K.R., Enthalpies for toluene and methylcyclohexane in the fluid state, J. Chem. Eng. Data, 1984, 29, 389-393. [all data]

Majer, Svoboda, et al., 1979
Majer, Vladimír; Svoboda, Václav; Hála, Slavoj; Pick, Jirí, Temperature dependence of heats of vaporization of saturated hydrocarbons C5-C8; Experimental data and an estimation method, Collect. Czech. Chem. Commun., 1979, 44, 3, 637-651, https://doi.org/10.1135/cccc19790637 . [all data]

Spitzer and Pitzer, 1946
Spitzer, Ralph; Pitzer, Kenneth S., The Heat Capacity of Gaseous Cyclopentane, Cyclohexane and Methylcyclohexane, J. Am. Chem. Soc., 1946, 68, 12, 2537-2538, https://doi.org/10.1021/ja01216a032 . [all data]

Willingham, Taylor, et al., 1945
Willingham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor pressures and boiling points of some paraffin, alkylcyclopentane, alkylcyclohexane, and alkylbenzene hydrocarbons, J. RES. NATL. BUR. STAN., 1945, 35, 3, 219-17, https://doi.org/10.6028/jres.035.009 . [all data]

Stuckey and Saylor, 1940
Stuckey, James M.; Saylor, John H., The Vapor Pressures of Some Organic Compounds. I. 1, J. Am. Chem. Soc., 1940, 62, 11, 2922-2925, https://doi.org/10.1021/ja01868a011 . [all data]

Douslin and Huffman, 1946, 2
Douslin, D.R.; Huffman, H.M., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentane, methylcyclopentane and methylcylohexane, J. Am. Chem. Soc., 1946, 68, 173-176. [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]

Parks and Huffman, 1930
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IX. A study of the effect of unsaturation on the heat capacities, entropies and free energies of some hydrocarbons and other compounds, J. Am. Chem. Soc., 1930, 52, 4381-4391. [all data]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [all data]

Sieck and Mautner(Meot-Ner), 1982
Sieck, L.W.; Mautner(Meot-Ner), M., Ionization energies and entropies of cycloalkanes. Kinetics of free energy controlled charge-transfer reactions, J. Phys. Chem., 1982, 86, 3646. [all data]

Lias, 1982
Lias, S.G., Thermochemical information from ion-molecule rate constants, Ion Cyclotron Reson. Spectrom. 1982, 1982, 409. [all data]

Mautner(Meot-Ner), Sieck, et al., 1981
Mautner(Meot-Ner), M.; Sieck, L.W.; Ausloos, P., Ionization of normal alkanes: Enthalpy, entropy, structural, and isotope effects, J. Am. Chem. Soc., 1981, 103, 5342. [all data]

Rang, Paldoia, et al., 1974
Rang, S.; Paldoia, P.; Talvari, A., Ionization potentials of unsaturated hydrocarbons. 2. Mono-substituted cyclopentenes and cyclohexenes, Eesti. NSV Tead. Akad. Toim., 1974, 354. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Pottie, Harrison, et al., 1961
Pottie, R.F.; Harrison, A.G.; Lossing, F.P., Free radicals by mass spectrometry. XXIV. Ionization potentials of cycloalkyl free radicals and cycloalkanes, J. Am. Chem. Soc., 1961, 83, 3204. [all data]


Notes

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