Cyclohexane, methyl-

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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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas-154.8 ± 1.0kJ/molCcbProsen, Johnson, et al., 1946ALS
Δfgas-159.9kJ/molN/AMoore, Renquist, et al., 1940Value computed using ΔfHliquid° value of -195.3±1.9 kj/mol from Moore, Renquist, et al., 1940 and ΔvapH° value of 35.4 kj/mol from Prosen, Johnson, et al., 1946.; DRB
Quantity Value Units Method Reference Comment
gas343.30J/mol*KN/ABeckett C.W., 1947GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
36.5050.Thermodynamics Research Center, 1997p=1 bar. Recommended S(T) and Cp(T) values differ significantly from earlier statistically calculated values [ Beckett C.W., 1947] at high temperatures (6 and 7 J/mol*K, respectively, at 1500 K).; GT
52.01100.
70.55150.
90.31200.
123.5273.15
135.8298.15
136.7300.
186.0400.
229.9500.
266.8600.
297.6700.
323.5800.
345.4900.
364.11000.
380.11100.
393.81200.
405.61300.
415.81400.
424.51500.
441.81750.
454.22000.
463.32250.
470.12500.
475.42750.
479.53000.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
180.75390.Spitzer R., 1946Please also see Montgomery J.B., 1942.; GT
184.6 ± 1.7398.
189.12410.
203.4 ± 2.1439.
222.8 ± 2.1480.
241.9 ± 2.5527.

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-190.2 ± 1.0kJ/molCcbProsen, Johnson, et al., 1946ALS
Δfliquid-195.3 ± 1.9kJ/molCcbMoore, Renquist, et al., 1940Reanalyzed by Cox and Pilcher, 1970, Original value = -192.5 kJ/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-4565.29 ± 0.96kJ/molCcbProsen, Johnson, et al., 1946Corresponding Δfliquid = -190.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-4564.3 ± 1.9kJ/molCcbMoore, Renquist, et al., 1940Reanalyzed by Cox and Pilcher, 1970, Original value = -4562.3 ± 1.9 kJ/mol; Corresponding Δfliquid = -191.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-4604.9kJ/molCcbZubova, 1901Corresponding Δfliquid = -151. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid247.90J/mol*KN/ADouslin and Huffman, 1946DH
liquid248.1J/mol*KN/AParks and Huffman, 1930Extrapolation below 90 K, 54.73 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
184.38298.15Shiohama, Ogawa, et al., 1988DH
184.96298.15Tanaka, 1985DH
185.29298.15Grolier, Inglese, et al., 1982T = 298.15 K.; DH
184.8298.15Wilhelm, Grolier, et al., 1979DH
184.84298.15Holzhauer and Ziegler, 1975T = 144 to 312 K. Cp = 129.88277 - 0.0054107773T + 7.9975642x10-4T2 J/mol*K.; DH
185.27298.055Hwa and Ziegler, 1966T = 175 to 308 K. Unsmoothed experimental datum.; DH
184.51298.15Douslin and Huffman, 1946T = 12 to 300 K.; DH
182.0294.2Parks and Huffman, 1930T = 93 to 294 K. Value is unsmoothed experimental datum.; DH

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, 1946, 2Uncertainty assigned by TRC = 0.05 K; To = 273.16 K; TRC
Ttriple146.57KN/ADouslin and Huffman, 1946, 2Uncertainty 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, 1946DH
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, 1946DH
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:


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

Cyclohexane, methylene- + Hydrogen = Cyclohexane, methyl-

By formula: C7H12 + H2 = C7H14

Quantity Value Units Method Reference Comment
Δr-119.5 ± 0.65kJ/molChydRogers, Crooks, et al., 1987liquid phase
Δr-116.1 ± 0.54kJ/molChydTurner and Garner, 1958liquid phase; solvent: Acetic acid
Δr-116.1 ± 0.54kJ/molEqkTurner and Garner, 1957liquid phase; solvent: Acetic acid
Δr-120.1 ± 0.3kJ/molChydTurner and Garner, 1957, 2liquid phase; solvent: Acetic acid

Hydrogen + Cyclohexene, 1-methyl- = Cyclohexane, methyl-

By formula: H2 + C7H12 = C7H14

Quantity Value Units Method Reference Comment
Δr-111.4 ± 0.37kJ/molChydRogers, Crooks, et al., 1987liquid phase
Δr-106.3 ± 0.46kJ/molChydTurner and Garner, 1958liquid phase; solvent: Acetic acid
Δr-106.3 ± 0.46kJ/molChydTurner and Garner, 1957liquid phase; solvent: Acetic acid

2Hydrogen + trans-Bicyclo[4.1.0]hept-3-ene = Cyclohexane, methyl-

By formula: 2H2 + C7H10 = C7H14

Quantity Value Units Method Reference Comment
Δr-387. ± 0.4kJ/molChydRoth, Adamczak, et al., 1991liquid phase

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.00979400.MN/A 
0.00939100.XN/A 
0.0023 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.0025 LN/A 
0.0023 VN/A 

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-3722
NIST MS number 227871

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), Notes

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

Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heats of formation and combustion of the normal alkylcyclopentanes and cyclohexanes and the increment per CH2 group for several homologous series of hydrocarbons, J. Res. NBS, 1946, 37, 51-56. [all data]

Moore, Renquist, et al., 1940
Moore, G.E.; Renquist, M.L.; Parks, G.S., Thermal data on organic compounds. XX. Modern combustion data for two methylnonanes, methyl ethyl ketone, thiophene and six cycloparaffins, J. Am. Chem. Soc., 1940, 62, 1505-1507. [all data]

Beckett C.W., 1947
Beckett C.W., The thermodynamic properties and molecular structure of cyclohexane, methylcyclohexane, ethylcyclohexane, and seven dimethylcyclohexanes, J. Am. Chem. Soc., 1947, 69, 2488-2495. [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]

Spitzer R., 1946
Spitzer R., The heat capacity of gaseous cyclopentane, cyclohexane and methylcyclohexane, J. Am. Chem. Soc., 1946, 68, 2537-2538. [all data]

Montgomery J.B., 1942
Montgomery J.B., The heat capacity of organic vapors. IV. Benzene, fluorobenzene, toluene, cyclohexane, methylcyclohexane and cyclohexene, J. Am. Chem. Soc., 1942, 64, 2375-2377. [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]

Zubova, 1901
Zubova, P., Data about heat of combustion of compound cycle structure, Zh. Fiz. Khim., 1901, 33, 708-722. [all data]

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 methylcylohexane, J. Am. Chem. Soc., 1946, 68, 173-176. [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]

Shiohama, Ogawa, et al., 1988
Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I., Excess thermodynamic properties of (cis-decalin or trans-decalin + cyclohexane or methylcyclohexane or cyclooctane) at 298.15 K, J. Chem. Thermodynam., 1988, 20, 1307-1314. [all data]

Tanaka, 1985
Tanaka, R., Excess heat capacities for mixtures of benzene with cyclopentane, methylcyclohexane, and cyclooctane at 298.15 K, J. Chem. Eng. Data, 1985, 30, 267-269. [all data]

Grolier, Inglese, et al., 1982
Grolier, J.-P.E.; Inglese, A.; Wilhelm, E., Excess volumes and excess heat capacities of tetrachloroethene + cyclohexane, + methylcyclohexane, + benzene, and + toluene at 298.15 K, J. Chem. Thermodynam., 1982, 14, 523-529. [all data]

Wilhelm, Grolier, et al., 1979
Wilhelm, E.; Grolier, G.-P.E.; Karbalai Ghassemi, M.H., Molar heat capacity of binary liquid mixtures: 1,2-dichloroethane + cyclohexane and 1,2-dichloroethane + methylcyclohexane, Thermochim. Acta, 1979, 28, 59-69. [all data]

Holzhauer and Ziegler, 1975
Holzhauer, J.K.; Ziegler, W.T., Temperature dependence of excess thermodynamic properties of n-heptane-toluene, methylcyclohexane-toluene, and n-heptane-methylcyclohexane systems, J. Phys. Chem., 1975, 79(6), 590-604. [all data]

Hwa and Ziegler, 1966
Hwa, S.C.P.; Ziegler, W.T., Temperature dependence of excess thermodynamic properties of ethanol-methylcyclohexane and ethanol-toluene systems, J. Phys. Chem., 1966, 70(8), 2572-2593. [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 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]

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]

Rogers, Crooks, et al., 1987
Rogers, D.W.; Crooks, E.; Dejroongruang, K., Enthalpies of hydrogenation of the hexenes, J. Chem. Thermodyn., 1987, 19, 1209-1215. [all data]

Turner and Garner, 1958
Turner, R.B.; Garner, R.H., Heats of hydrogenation. V. Relative stabilities in certain exocyclic-endocyclic olefin pairs, J. Am. Chem. Soc., 1958, 80, 1424-1430. [all data]

Turner and Garner, 1957
Turner, R.B.; Garner, R.H., Heats of hydrogenation. V. Relative stabilities in certain exocyclic-endocyclic olefin pairs, J. Am. Chem. Soc., 1957, 80, 1424-1430. [all data]

Turner and Garner, 1957, 2
Turner, R.B.; Garner, R.H., The stability relationship of 1-methyl-cyclopentene and methylenecyclopentane, J. Am. Chem. Soc., 1957, 79, 253. [all data]

Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R., Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld, Chem. Ber., 1991, 124, 2499-2521. [all data]


Notes

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