Cyclohexane, methyl-
- Formula: C7H14
- Molecular weight: 98.1861
- IUPAC Standard InChIKey: UAEPNZWRGJTJPN-UHFFFAOYSA-N
- CAS Registry Number: 108-87-2
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Isotopologues:
- Other names: Cyclohexylmethane; Hexahydrotoluene; Methylcyclohexane; Sextone B; Toluene hexahydride; Hexahydroxytoluene; Metylocykloheksan; Toluene, hexahydro-; UN 2296; NSC 9391
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -45.45 ± 0.25 | kcal/mol | Ccb | Prosen, Johnson, et al., 1946 | ALS |
ΔfH°liquid | -46.67 ± 0.46 | kcal/mol | Ccb | Moore, Renquist, et al., 1940 | Reanalyzed by Cox and Pilcher, 1970, Original value = -46.02 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1091.13 ± 0.23 | kcal/mol | Ccb | Prosen, Johnson, et al., 1946 | Corresponding ΔfHºliquid = -45.43 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1090.89 ± 0.45 | kcal/mol | Ccb | Moore, Renquist, et al., 1940 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1090.42 ± 0.45 kcal/mol; Corresponding ΔfHºliquid = -45.67 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1100.6 | kcal/mol | Ccb | Zubova, 1901 | Corresponding ΔfHºliquid = -36.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 59.250 | cal/mol*K | N/A | Douslin and Huffman, 1946 | DH |
S°liquid | 59.30 | cal/mol*K | N/A | Parks and Huffman, 1930 | Extrapolation below 90 K, 54.73 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
44.068 | 298.15 | Shiohama, Ogawa, et al., 1988 | DH |
44.207 | 298.15 | Tanaka, 1985 | DH |
44.285 | 298.15 | Grolier, Inglese, et al., 1982 | T = 298.15 K.; DH |
44.17 | 298.15 | Wilhelm, Grolier, et al., 1979 | DH |
44.178 | 298.15 | Holzhauer and Ziegler, 1975 | T = 144 to 312 K. Cp = 129.88277 - 0.0054107773T + 7.9975642x10-4T2 J/mol*K.; DH |
44.281 | 298.055 | Hwa and Ziegler, 1966 | T = 175 to 308 K. Unsmoothed experimental datum.; DH |
44.099 | 298.15 | Douslin and Huffman, 1946 | T = 12 to 300 K.; DH |
43.50 | 294.2 | Parks and Huffman, 1930 | T = 93 to 294 K. Value is unsmoothed experimental datum.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
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 |
---|---|---|---|---|---|
Tboil | 374.0 ± 0.8 | K | AVG | N/A | Average of 101 out of 106 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 146.6 ± 0.4 | K | AVG | N/A | Average of 15 out of 16 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 146.58 | K | N/A | Douslin and Huffman, 1946, 2 | Uncertainty assigned by TRC = 0.05 K; To = 273.16 K; TRC |
Ttriple | 146.57 | K | N/A | Douslin and Huffman, 1946, 2 | Uncertainty assigned by TRC = 0.08 K; To = 273.16 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 573. ± 2. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 34.3 ± 0.2 | atm | N/A | Daubert, 1996 | |
Pc | 34.26 | atm | N/A | Kudchadker, Alani, et al., 1968 | Uncertainty assigned by TRC = 0.300 atm; TRC |
Pc | 34.3220 | atm | N/A | Kay, 1947 | Uncertainty assigned by TRC = 0.0499 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.369 | l/mol | N/A | Daubert, 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.71 ± 0.02 | mol/l | N/A | Daubert, 1996 | |
ρc | 2.719 | mol/l | N/A | Kudchadker, Alani, et al., 1968 | Uncertainty assigned by TRC = 0.03 mol/l; TRC |
ρc | 2.715 | mol/l | N/A | Simon, 1957 | Uncertainty assigned by TRC = 0.03 mol/l; TRC |
ρc | 2.71 | mol/l | N/A | Kay, 1947 | Uncertainty assigned by TRC = 0.02 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.44 ± 0.05 | kcal/mol | AVG | N/A | Average of 10 out of 11 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.474 | 374.1 | N/A | Majer and Svoboda, 1985 | |
8.08 | 340. | N/A | Sapei, Uusi-Kyyny, et al., 2010 | Based on data from 325. to 374. K.; AC |
8.65 | 310. | N/A | Wu, Pividal, et al., 1991 | Based on data from 295. to 333. K.; AC |
7.72 | 388. | A | Stephenson and Malanowski, 1987 | Based on data from 373. to 511. K.; AC |
7.46 | 516. | A | Stephenson and Malanowski, 1987 | Based on data from 501. to 573. K.; AC |
8.27 | 323. | A | Stephenson and Malanowski, 1987 | Based on data from 308. to 368. K. See also Valerga, 1970 and Boublik, Fried, et al., 1984.; AC |
7.70 | 353. | N/A | Eubank, Cediel, et al., 1984 | AC |
7.15 | 393. | N/A | Eubank, Cediel, et al., 1984 | AC |
6.43 | 433. | N/A | Eubank, Cediel, et al., 1984 | AC |
5.59 | 473. | N/A | Eubank, Cediel, et al., 1984 | AC |
8.27 ± 0.02 | 313. | C | Majer, Svoboda, et al., 1979 | AC |
8.01 ± 0.02 | 333. | C | Majer, Svoboda, et al., 1979 | AC |
7.77 ± 0.02 | 353. | C | Majer, Svoboda, et al., 1979 | AC |
7.60 | 374. | N/A | Spitzer and Pitzer, 1946 | AC |
8.34 | 314. | MM | Willingham, Taylor, et al., 1945 | Based on data from 299. to 375. K.; AC |
8.63 | 288. | N/A | Stuckey and Saylor, 1940 | Based 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)
(kcal/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 374. | 11.85 | 0.2685 | 572.1 | Majer and Svoboda, 1985 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.6134 | 146.58 | Douslin and Huffman, 1946 | DH |
1.60 | 146.6 | Domalski and Hearing, 1996 | AC |
1.595 | 146.2 | Parks and Huffman, 1930 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.01 | 146.58 | Douslin and Huffman, 1946 | DH |
10.79 | 146.2 | Parks and Huffman, 1930 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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 ± 0.10 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.62 ± 0.05 | EI | Holmes and Lossing, 1991 | LL |
9.64 | EQ | Sieck and Mautner(Meot-Ner), 1982 | LBLHLM |
9.64 ± 0.10 | EVAL | Lias, 1982 | LBLHLM |
9.69 ± 0.15 | EQ | Mautner(Meot-Ner), Sieck, et al., 1981 | LLK |
9.76 ± 0.03 | PE | Rang, Paldoia, et al., 1974 | LLK |
9.85 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H11+ | 10.95 | CH3 | EI | Pottie, Harrison, et al., 1961 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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]
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]
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
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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