Toluene

• Formula: C₇H₈
• Molecular weight: 92.1384
• IUPAC Standard InChI: InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3 Copy

  
• IUPAC Standard InChIKey: YXFVVABEGXRONW-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-88-3
• 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:
  • Toluene-D3
  • Toluene-D8
• Other names: Benzene, methyl; Methacide; Methylbenzene; Methylbenzol; Phenylmethane; Antisal 1a; Toluol; Methane, phenyl-; NCI-C07272; Tolueen; Toluen; Toluolo; Rcra waste number U220; Tolu-sol; UN 1294; Dracyl; Monomethyl benzene; CP 25; NSC 406333; methylbenzene (toluene)
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • Fluid Properties
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
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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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change data

Go To: Top, Condensed phase 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:
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
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes

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

Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y., Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons, J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]

Prosen, Gilmont, et al., 1945
Prosen, E.J.; Gilmont, R.; Rossini, F.D., Heats of combustion of benzene, toluene, ethyl-benzene, o-xylene, m-xylene, p-xylene, n-propylbenzene, and styrene, J. Res. NBS, 1945, 34, 65-70. [all data]

Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heats of combustion and formation at 25°C of the alkylbenzenes through C₁₀H₁₄, and of the higher normal monoalkylbenzenes, J. Res. NBS, 1946, 36, 455-461. [all data]

Schmidlin, 1906
Schmidlin, M.J., Recherches chimiques et thermochimiques sur la constitution des rosanilines, Ann. Chim. Phys., 1906, 1, 195-256. [all data]

Scott, Guthrie, et al., 1962
Scott, D.W.; Guthrie, G.B.; Messerly, J.F.; Todd, S.S.; Berg, W.T.; Hossenlopp, I.A.; McCullough, J.P., Toluene: thermodynamic properties, molecular vibrations, and internal rotation, J. Phys. Chem., 1962, 66, 911-914. [all data]

Kelley, 1929
Kelley, K.K., The heat capacity of toluene from 14K to 298K. The entropy and the free energy of formation, J. Am. Chem. Soc., 1929, 51, 2738-2741. [all data]

Grolier, Roux-Desgranges, et al., 1993
Grolier, J.-P.E.; Roux-Desgranges, G.; Berkane, M.; Jimenez, E.; Wilhelm, E., Heat capacities and densities of mixtures of very polar substances 2. Mixtures containing N,N-dimethylformamide, J. Chem. Thermodynam., 1993, 25(1), 41-50. [all data]

Shiohama, Ogawa, et al., 1988
Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I., Excess molar isobaric heat capacities and isentropic compressibilities of (cis- or trans-decalin + benzene or toluene or iso-octane or n-heptane) at 298.15 K, J. Chem. Thermodynam., 1988, 20, 1183-1189. [all data]

Reddy, 1986
Reddy, K.S., Isentropic compressibilities of binary liquid mixtures at 303.15 and 313.15 K, J. Chem. Eng. Data, 1986, 31, 238-240. [all data]

Roux-Dexgranges, Grolier, et al., 1986
Roux-Dexgranges, G.; Grolier, J.-P.E.; Villamanan, M.A.; Casanova, C., Role of alcohol in microemulsions. III. Volumes and heat capacities in the continuious phase water-n-butanol-toluene of reverse micelles, Fluid Phase Equilibria, 1986, 25, 209-230. [all data]

Tardajos, Aicart, et al., 1986
Tardajos, G.; Aicart, E.; Costas, M.; Patterson, D., Liquid structure and second-order mixing functions for benzene, toluene, and p-xylene with n-alkanes, J. Chem. Soc., Faraday Trans., 1986, 1 82, 2977-2987. [all data]

Stephens and Olson, 1984
Stephens, M.; Olson, J.D., Measurement of excess heat capacities by differential scanning calorimetry, Thermochim. Acta, 1984, 76, 79-85. [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, Faradjzadeh, et al., 1982
Wilhelm, E.; Faradjzadeh, A.; Grolier, J.-P.E., Excess volumes and excess heat capacities of 2,3-dimethylbutane + butane and + toluene, J. Chem. Thermodynam., 1982, 14, 1199-1200. [all data]

Atalla, El-Sharkawy, et al., 1981
Atalla, S.R.; El-Sharkawy, A.A.; Gasser, F.A., Measurement of thermal properties of liquids with an AC heated-wire technique, Inter. J. Thermophys., 1981, 2(2), 155-162. [all data]

Andolenko and Grigor'ev, 1979
Andolenko, R.A.; Grigor'ev, B.A., Investigation of isobaric heat capacity of aromatic hydrocarbons at atmospheric pressure, Iaz. Vyssh. Ucheb. Zaved., Neft i Gaz (11), 1979, 78, 90. [all data]

Fortier and Benson, 1979
Fortier, J.-L.; Benson, G.C., Heat capacities of some binary aromatic hydrocarbon mixtures containing benzene or toluene, J. Chem. Eng. Data, 1979, 24(1), 34-37. [all data]

Fortier and Benson, 1977
Fortier, J.-L.; Benson, G.C., Excess heat capacities of binary mixtures of tetrachloromethane witlh some aromatic liquids at 298.15 K, J. Chem. Thermodynam., 1977, 9, 1181-1188. [all data]

Wilhelm, Grolier, et al., 1977
Wilhelm, E.; Grolier, J.-P.E.; Karbalai Ghassemi, M.H., Molar heat capacities of binary liquid mixtures: 1,2-dichloroethane + benzene, + toluene, and + p-xylene, Ber. Bunsenges. Phys. Chem., 1977, 81, 925-930. [all data]

Fortier and Benson, 1976
Fortier, J.-L.; Benson, G.C., Excess heat capacities of binary liquid mixtures determined with a Picker flow calorimeter, J. Chem. Thermodynam., 1976, 8, 411-423. [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]

Pedersen, Kay, et al., 1975
Pedersen, M.J.; Kay, W.B.; Hershey, H.C., Excess enthalpies, heat capacities, and excess heat capacities as a function of temperature in liquid mixtures of ethanol + toluene, ethanol + hexamethyldisiloxane, and hexamethyldisiloxane + toluene, J. Chem. Thermodynam., 1975, 7, 1107-1118. [all data]

Rajagopal and Subrahmanyam, 1974
Rajagopal, E.; Subrahmanyam, S.V., Excess function of VE,(dVE/dp)T, and CpE of isooctane + benzene and + toluene, J. Chem. Thermodynam., 1974, 6, 873-876. [all data]

Deshpande and Bhatagadde, 1971
Deshpande, D.D.; Bhatagadde, L.G., Heat capacities at constant volume, free volumes, and rotational freedom in some liquids, Aust. J. Chem., 1971, 24, 1817-1822. [all data]

Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A., Study of the heat capacity of selected solvents, Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [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]

Swietoslawski and Zielenkiewicz, 1958
Swietoslawski, W.; Zielenkiewicz, A., Mean specific heats of binary positive azeotropes, Bull. Acad. Pol. Sci. Ser. Sci. Chim., 1958, 6, 367-369. [all data]

Tschamler, 1948
Tschamler, H., Uber binare flussige Mischungen I. Mischungswarment, Volumseffekte und Zustandsdiagramme von chlorex mit benzol und n-alkylbenzolen, Monatsh. Chem., 1948, 79, 162-177. [all data]

Kurbatov, 1947
Kurbatov, V.Ya., Specific heat of liquids. I. Specific heat of benzenoid hydrocarbons, Zhur. Obshch. Khim., 1947, 17, 1999-2003. [all data]

Zhdanov, 1941
Zhdanov, A.K., Specific heats of some liquids and azeotropic mixtures, Zhur. Obshch. Khim., 1941, 11, 471-482. [all data]

Burlew, 1940
Burlew, J.S., Measurement of the heat capacity of a small volume of liquid by the piezo-thermometric method. III. Heat capacity of benzene and of toluene from 8°C. to the boiling point, J. Am. Chem. Soc., 1940, 62, 696-700. [all data]

Vold, 1937
Vold, R.D., A calorimetric test of the solubility equation for regular solutions, J. Am. Chem. Soc., 1937, 59, 1515-1521. [all data]

Aoyama and Kanda, 1935
Aoyama, S.; Kanda, E., Studies on the heat capacities at low temperature. Report I. Heat capacities of some organic substances at low temperature, Sci. Rept. Tohoku Imp. Univ. [1]24, 1935, 107-115. [all data]

Richards and Wallace, 1932
Richards, W.T.; Wallace, J.H., Jr., The specific heats of five organic liquids from their adiabatic temperature-pressure coefficients, J. Am. Chem. Soc., 1932, 54, 2705-2713. [all data]

Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H., Thermal energy studies. I. Phenyl derivatives of methane, ethane and some related compounds. J. Am. Chem. Soc., 1931, 53, 3644-3660. [all data]

Williams and Daniels, 1925
Williams, J.W.; Daniels, F., The specific heats of binary mixtures, J. Am. Chem. Soc., 1925, 47, 1490-1503. [all data]

Willams and Daniels, 1924
Willams, J.W.; Daniels, F., The specific heats of certain organic liquids at elevated temperatures, J. Am. Chem. Soc., 1924, 46, 903-917. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Scott, Guthrie, et al., 1962, 2
Scott, D.W.; Guthrie, G.B.; Messerly, J.F.; Todd, S.S.; Berg, W.T.; Hossenlopp, I.A.; McCullough, J.P., Toluene: Thermodynamic Propoerties, Molecular Vibrations, and Internal Rotation, J. Phys. Chem., 1962, 66, 911-4. [all data]

Ziegler and Andrews, 1942
Ziegler, W.T.; Andrews, D.H., The heat capacity of benzene-d6, J. Am. Chem. Soc., 1942, 64, 2482. [all data]

Stull, 1937
Stull, D.R., A Semi-micro Calorimeter for Measuring Heat Capacities at Low Temp., J. Am. Chem. Soc., 1937, 59, 2726. [all data]

Kelley, 1929, 2
Kelley, K.K., The heat capacity of toluene from 14 deg K to 298 deg K. the entropy and the free energy of formation., J. Am. Chem. Soc., 1929, 51, 2738. [all data]

Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons, J. Chem. Eng. Data, 1995, 40, 547-558. [all data]

Chirico and Steele, 1994
Chirico, R.D.; Steele, W.V., Reconciliation of Calorimetrically and Spectroscopically Derived Methyl Benzene. The Importance of the Third Virial Coefficient, Ind. Eng. Chem. Res., 1994, 33, 157-67. [all data]

Goodwin, 1989
Goodwin, R.D., Toluene thermophysical properties from 178 to 800 K at pressures to 1000 Bar, J. Phys. Chem. Ref. Data, 1989, 18, 1565-636. [all data]

Steele, Chirico, et al., 1988
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Smith, N.K., , Report, NIPPR-395, 1988. [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]

Lenchitz and Velicky, 1970
Lenchitz, Charles; Velicky, Rodolf W., Vapor pressure and heat of sublimation of three nitrotoluenes, J. Chem. Eng. Data, 1970, 15, 3, 401-403, https://doi.org/10.1021/je60046a022 . [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Lee and Holder, 1993
Lee, Chang Ha; Holder, Gerald D., Vapor-liquid equilibria in the systems toluene/naphthalene and cyclohexane/naphthalene, J. Chem. Eng. Data, 1993, 38, 2, 320-323, https://doi.org/10.1021/je00010a034 . [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]

Forziati, Norris, et al., 1949
Forziati, Alphonse F.; Norris, William R.; Rossini, Frederick D., Vapor pressures and boiling points of sixty API-NBS hydrocarbons, J. RES. NATL. BUR. STAN., 1949, 43, 6, 555-17, https://doi.org/10.6028/jres.043.050 . [all data]

Natarajan and Viswanath, 1985
Natarajan, Govindarajan; Viswanath, Dabir S., Enthalpy of vaporization and vapor pressure of benzene, toluene, p-xylene, and tetralin between 1 and 16 bar, J. Chem. Eng. Data, 1985, 30, 2, 137-140, https://doi.org/10.1021/je00040a001 . [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]

Rivenq, 1975
Rivenq, F., Bull. Soc. Chim. Fr., 1975, 1, 2433. [all data]

Gaw and Swinton, 1968
Gaw, W.J.; Swinton, F.L., Thermodynamic properties of binary systems containing hexafluorobenzene. Part 4.?Excess Gibbs free energies of the three systems hexafluorobenzene + benzene, touene, and p-xylene, Trans. Faraday Soc., 1968, 64, 2023, https://doi.org/10.1039/tf9686402023 . [all data]

Van Ness, Soczek, et al., 1967
Van Ness, Hendrick C.; Soczek, C.A.; Peloquin, G.L.; Machado, R.L., Thermodynamic excess properties of three alcohol-hydrocarbon systems, J. Chem. Eng. Data, 1967, 12, 2, 217-224, https://doi.org/10.1021/je60033a017 . [all data]

Scott, Gutherie, et al., 1962
Scott, D.W.; Gutherie, G.B.; Messerly, J.F.; Todd, S.S.; Berg, W.T.; Hossenlopp, I.A.; McCullough, J.P., Toluene: Thermodynamic properties, molecular vibrations, and internal rotation, J. Phys. Chem., 1962, 66, 911. [all data]

Milazzo, 1956
Milazzo, G., Ann. Chim. (Rome), 1956, 46, 1105. [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]

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]

Pitzer and Scott, 1943
Pitzer, K.S.; Scott, D.W., The thermodynamics and molecular structure of benzene and its methyl derivatives, J. Am. Chem. Soc., 1943, 65, 803-829. [all data]

Besley and Bottomley, 1974
Besley, L.M.; Bottomley, G.A., Vapour Pressure of Toluene from 273.15 to 298.15 K, J. Chem. Thermodyn., 1974, 6, 6, 577-580, https://doi.org/10.1016/0021-9614(74)90045-7 . [all data]

Gaw and Swinton, 1968, 2
Gaw, W.J.; Swinton, F.L., Thermodynamic Properties of Binary Systems Containing Hexafluorobenzene. Part 3. Excess Gibbs Free Energy of the System Hexafluorobenzene + Cyclohexane, Trans. Faraday Soc., 1968, 64, 637-647, https://doi.org/10.1039/tf9686400637 . [all data]

Ambrose, Broderick, et al., 1967
Ambrose, D.; Broderick, B.E.; Townsend, R., The Vapour Pressures Above the Normal Boiling Point and the Critical Pressures of Some Aromatic Hydrocarbons, J. Chem. Soc. A:, 1967, 633-641, https://doi.org/10.1039/j19670000633 . [all data]

Williamham, Taylor, et al., 1945
Williamham, 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. Stand. (U.S.), 1945, 35, 3, 219-244, https://doi.org/10.6028/jres.035.009 . [all data]

Ziegler and Andrews, 1942, 2
Ziegler, W.T.; Andrews, D.H., The heat capacity of benzene-d6, J. Am. Chem. Soc., 1942, 64, 2482-2485. [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]

Southard and Andrews, 1930
Southard, John C.; Andrews, Donald H., The heat capacities of organic compounds at low temperatures. iii. an adiabatic calorimeter for heat capacities at low temperatures, Journal of the Franklin Institute, 1930, 209, 3, 349-360, https://doi.org/10.1016/S0016-0032(30)90040-3 . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  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
  ΔsubH°	Enthalpy of sublimation at standard conditions
  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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