Benzoic acid

• Formula: C₇H₆O₂
• Molecular weight: 122.1213
• IUPAC Standard InChI: InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9) Copy

  
• IUPAC Standard InChIKey: WPYMKLBDIGXBTP-UHFFFAOYSA-N Copy
• CAS Registry Number: 65-85-0
• 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.
• Other names: Benzenecarboxylic acid; Benzeneformic acid; Benzenemethanoic acid; Benzoesaeure GK; Benzoesaeure GV; Carboxybenzene; Dracylic acid; Phenylcarboxylic acid; Phenylformic acid; Retarder BA; Retardex; Salvo, liquid; Solvo, powder; Tenn-Plas; Acide benzoique; Benzoic acid, tech.; Kyselina benzoova; Benzoesaeure; Salvo powder; E 210; HA 1; HA 1 (acid); Phenylcarboxy; Benzenemethonic acid; Diacylic acid; Flowers of benjamin; Flowers of benzoin; Oracylic acid; Retarder BAX; NSC 149
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• 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
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Condensed phase thermochemistry 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 compiled as indicated in comments:
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

Constant pressure heat capacity of solid

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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Reduced pressure boiling point

Enthalpy of vaporization

Entropy of vaporization

Antoine Equation Parameters

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

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Enthalpy of sublimation

Entropy of sublimation

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

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.

Gundry, Harrop, et al., 1969
Gundry, H.A.; Harrop, D.; Head, A.J.; Lewis, G.B., Thermodynamic properties of organic oxygen compounds. 21. Enthalpies of combustion of benzoic acid, pentan-1-ol, octan-1-ol, and hexadecan-1-ol, J. Chem. Thermodyn., 1969, 1, 321-332. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Corral, 1960
Corral, L.B., Investigaciones termoquimicas sobre los acidos toluicos y dimetilbenzoicos, Rev. R. Acad. Cienc., 1960, 54, 365-403. [all data]

Landrieu, Baylocq, et al., 1929
Landrieu, P.; Baylocq, F.; Johnson, J.R., Etude thermochimique dans la serie furanique, Bull. Soc. Chim. France, 1929, 45, 36-49. [all data]

Kaji, Tochigi, et al., 1993
Kaji, K.; Tochigi, K.; Misawa, Y.; Suzuki, T., An adiabatic calorimeter for samples of mass less than 0.1 g and heat capacity measurements on benzoic acid at temperatures from 19 K to 312 K, J. Chem. Thermodynam., 1993, 25(6), 699-709. [all data]

Arvidsson, Falk, et al., 1976
Arvidsson, K.; Falk, B.; Sunner, S., A small sample low temperature adiabatic heat capacity calorimeter with an automatic data acquisition system, Chem. Scr., 1976, 10, 193-200. [all data]

Furukawa, McCoskey, et al., 1951
Furukawa, G.T.; McCoskey, R.E.; King, G.J., Calorimetric properties of benzoic acid from 0 to 410K, J. Res., 1951, NBS 47, 256-261. [all data]

Davies and Staveley, 1957
Davies, T.; Staveley, L.A.K., The behaviour of the ammonium ion in the ammonium salt of tetraphenylboron by comparison of the heat capacities of the ammonium, rubidium, and potassium salts, Trans. Faraday Soc., 1957, 53, 19-30. [all data]

Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [all data]

Pacor, 1967
Pacor, P., Applicability of the DuPont 900 DTA apparatus in quantitative differential thermal analysis, Anal. Chim. Acta, 1967, 37, 200-208. [all data]

Sorai, Kaji, et al., 1992
Sorai, M.; Kaji, K.; Kaneko, Y., An automated adiabatic calorimeter for the temperature range 13 K to 530 K The heat capacities for benzoic acid from 15 K to 305 K and of synthetic sapphire from 60 K to 505 K, J. Chem. Thermodynam., 1992, 24(2), 167-180. [all data]

Moriya, Matsuo, et al., 1982
Moriya, K.; Matsuo, T.; Suga, H., Low temperature adiabatic calorimeter with a built-in cryo-refrigerator, J. Chem. Thermodynam., 1982, 14, 1143-1148. [all data]

Shakirov and Lyubarskii, 1980
Shakirov, R.F.; Lyubarskii, M.V., Low-temperature heat capacity and thermodynamic functions of methyl trichlorothioacrylate, SPSTL Deposited Publication 3 KhP-D80, 1980, 19p. [all data]

Tatsumi, Matsuo, et al., 1975
Tatsumi, M.; Matsuo, T.; Suga, H.; Seki, S., An adiabatic calorimeter for high-resolution heat capacity measurements in the temperature range from 12 to 300 K, Bull. Chem. Soc. Japan, 1975, 48, 3060-3066. [all data]

Mosselman, Mourik, et al., 1974
Mosselman, C.; Mourik, J.; Dekker, H., Enthalpies of phase change and heat capacities of some long-chain alcohols. Adiabatic semi-microcalorimeter for studies of polymorphism, J. Chem. Thermodynam., 1974, 6, 477-487. [all data]

Konicek, Suurkuusk, et al., 1971
Konicek, J.; Suurkuusk, J.; Wadso, I., A precise drop heat capacity calorimeter for small samples, Chemica Scripta, 1971, 1, 217-220. [all data]

Justice, 1969
Justice, B.H., Low temperature thermodynamic properties of aluminum trichloride, J. Chem. Eng. Data, 1969, 14, 4-5. [all data]

Suga and Seki, 1965
Suga, H.; Seki, S., An automatic adiabatic calorimeter for low temperatures. The heat capacity of standard benzoic acid, Bull. Chem. Soc. Japan, 1965, 38, 1000-1006. [all data]

David, 1964
David, D.J., Determination of specific heat and heat of fusion by differential thermal analysis. Study of theory and operating parameters, Anal. Chem., 1964, 36, 2162-2166. [all data]

Kolesov, Seregin, et al., 1962
Kolesov, V.P.; Seregin, E.A.; Skuratov, S.M., Adiabatic calorimeter of small volume for the determination of true heat capacity over the range 12-340K, Zhur. Fiz. Khim., 1962, 36, 647-651. [all data]

Popov and Kolesov, 1956
Popov, M.M.; Kolesov, V.P., Determination of the true specific heat of solid substances at low temperatures, Zhur. Obshch. Khim., 1956, 26, 2385-2393. [all data]

Ginnings and Furukawa, 1953
Ginnings, D.C.; Furukawa, G.T., Heat capacity standards for the range 14 to 1200°K, J. Am. Chem. Soc., 1953, 75, 522-527. [all data]

Satoh and Sogabe, 1939
Satoh, S.; Sogabe, T., The specific heats of some solid aromatic acids and their ammonium salts and the atomic heat of nitrogen, Sci. Pap. Inst. Phys. Chem. Res. (Tokyo), 1939, 36, 449-457. [all data]

Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J., The heat capacities and heat of crystallization of some isomeric aromatic compounds, J. Am. Chem. Soc., 1926, 48, 1274-1287. [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]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Burriel, 1931
Burriel, F., Physico-Chemical Study of Some Solid Organic Compounds at Ordinary Temperatures, and Their COrrelationo with Temperature, An. R. Soc. Esp. Fis. Quim., 1931, 29, 89. [all data]

Marsh, 1987
Marsh, K.N., Recommended Reference Materials for the Realization of Physicochemical Properties, Blackwell Sci. Pub., Oxford, 1987. [all data]

Andon and Connett, 1980
Andon, R.J.L.; Connett, J.E., Calibrants for thermal analysis. measurement of their enthalpies of fusion by adiabatic calorimetry., Thermochim. Acta, 1980, 42, 241. [all data]

Ginnings and Furukawa, 1953, 2
Ginnings, D.C.; Furukawa, G.T., Heat Capacity Standards for the Range 14 to 1200 K, J. Am. Chem. Soc., 1953, 75, 522-7. [all data]

Furukawa, McCoskey, et al., 1951, 2
Furukawa, G.T.; McCoskey, R.E.; King, G.J., Calorimetric properties of benzoic acid from 0 to 410 K, J. Res. Natl. Bur. Stand. (U. S.), 1951, 47, 256. [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Torres-Gomez, Barreiro-Rodriguez, et al., 1988
Torres-Gomez, L.A.; Barreiro-Rodriguez, G.; Galarza-Mondragon, A., A new method for the measurement of enthalpies of sublimation using differential scanning calorimetry, Thermochim. Acta, 1988, 124, 229-233. [all data]

Pena, Ribet, et al., 2003
Pena, R.; Ribet, J.P.; Maurel, J.L.; Valat, L.; Lacoulonche, F.; Chauvet, A., Sublimation and vaporisation processes of S(-) efaroxan hydrochloride, Thermochimica Acta, 2003, 408, 1-2, 85-96, https://doi.org/10.1016/S0040-6031(03)00321-6 . [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]

Matsubara and Kuwamoto, 1985
Matsubara, Norio; Kuwamoto, Tooru, Vapor pressure measurements in carrier gas containing ligand vapor using the transpiration technique, Thermochimica Acta, 1985, 83, 2, 193-202, https://doi.org/10.1016/0040-6031(85)87003-9 . [all data]

Cramer, 1943
Cramer, K.S.N., Chem. Zentr. II, 1943, 2234. [all data]

Klosky, Woo, et al., 1927
Klosky, Simon; Woo, Leo P.L.; Flanigan, Robert J., THE VAPOR-PRESSURE CURVE OF BENZOIC ACID, J. Am. Chem. Soc., 1927, 49, 5, 1280-1284, https://doi.org/10.1021/ja01404a017 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Selvakumar, Raghunathan, et al., 2009
Selvakumar, Jayapragasam; Raghunathan, Vinjamoor Seshadri; Nagaraja, Karachalacheruvu Seetharamaiah, Vapor Pressure Measurements of Sc(tmhd) ₃ and Synthesis of Stabilized Zirconia Thin Films by Hybrid CVD Technique Using Sc(tmhd) ₃ , Zr(tmhd) ₄ , and Al(acac) ₃ [tmhd, 2,2,6,6-tetramethyl-3,5-heptanedione; acac, 2,4-pentanedione] as Precursors, J. Phys. Chem. C, 2009, 113, 44, 19011-19020, https://doi.org/10.1021/jp906204c . [all data]

Ribeiro da Silva, Monte, et al., 2006
Ribeiro da Silva, Manuel A.V.; Monte, Manuel J.S.; Santos, Luís M.N.B.F., The design, construction, and testing of a new Knudsen effusion apparatus, The Journal of Chemical Thermodynamics, 2006, 38, 6, 778-787, https://doi.org/10.1016/j.jct.2005.08.013 . [all data]

Ginkel, Kruif, et al., 2001
Ginkel, C.H.D. van; Kruif, C.G. de; Waal, F.E.B. de, The need for temperature control in effusion experiments (and application to heat of sublimation determination), J. Phys. E: Sci. Instrum., 2001, 8, 6, 490-492, https://doi.org/10.1088/0022-3735/8/6/018 . [all data]

Zielenkiewicz, Perlovich, et al., 1999
Zielenkiewicz, X.; Perlovich, G.L.; Wszelaka-Rylik, M., Journal of Thermal Analysis and Calorimetry, 1999, 57, 1, 225-234, https://doi.org/10.1023/A:1010179814511 . [all data]

Elder, 1997
Elder, J.P., Sublimation measurements of pharmaceutical compounds by isothermal thermogravivletry, Journal of Thermal Analysis, 1997, 49, 2, 897-905, https://doi.org/10.1007/BF01996775 . [all data]

Da Silva and Monte, 1990
Da Silva, Manuel A.V. Ribeiro; Monte, Manuel J.S., The construction, testing and use of a new knudsen effusion apparatus, Thermochimica Acta, 1990, 171, 169-183, https://doi.org/10.1016/0040-6031(90)87017-7 . [all data]

Glukhova, Arkhangelova, et al., 1985
Glukhova, O.T.; Arkhangelova, N.M.; Teplitsky, A.B.; Sukhodub, L.F.; Yanson, I.K.; Kaminski, Miron, The low-temperature quartz resonator method for determination of the enthalpy of sublimation, Thermochimica Acta, 1985, 95, 1, 133-138, https://doi.org/10.1016/0040-6031(85)80041-1 . [all data]

Kaisersberger, Hädrich, et al., 1985
Kaisersberger, E.; Hädrich, W.; Emmerich, W.-D., Measurement of low vapour pressures according to the Knudsen effusion method, Thermochimica Acta, 1985, 95, 2, 331-336, https://doi.org/10.1016/0040-6031(85)85294-1 . [all data]

Colomina, Jimenez, et al., 1982
Colomina, M.; Jimenez, P.; Turrion, C., Vapour pressures and enthalpies of sublimation of naphthalene and benzoic acid, J. Chem. Thermodyn., 1982, 14, 779-784. [all data]

de Kruif and Blok, 1982
de Kruif, C.G.; Blok, J.G., The vapour pressure of benzoic acid, The Journal of Chemical Thermodynamics, 1982, 14, 3, 201-206, https://doi.org/10.1016/0021-9614(82)90011-8 . [all data]

Murata, Sakiyama, et al., 1982
Murata, S.; Sakiyama, M.; Seki, S., Construction and testing of a sublimation calorimetric system using a Calvet microcalorimeter, The Journal of Chemical Thermodynamics, 1982, 14, 8, 707-721, https://doi.org/10.1016/0021-9614(82)90167-7 . [all data]

Sachinidis and Hill, 1980
Sachinidis, J.; Hill, J.O., A re-evaluation of the enthalpy of sublimation of some metal acetylacetonate complexes, Thermochimica Acta, 1980, 35, 1, 59-66, https://doi.org/10.1016/0040-6031(80)85021-0 . [all data]

Nowak, Szczepaniak, et al., 1978
Nowak, M.J.; Szczepaniak, K.; Barski, A.; Shugar, D.Z., Z. Naturforsch. C, 1978, 33C, 876. [all data]

DeKruif, van Ginkel, et al., 1975
DeKruif, C.G.; van Ginkel, C.H.D.; Voogd, J., Torsion-effusion vapour pressure measurements of organic compounds, Conf. Int. Thermodyn. Chim. C. R. 4th, 1975, 8, 11-18. [all data]

Arshadi, 1974
Arshadi, Mohammed R., Determination of heats of sublimation of organic compounds by a mass spectrometric--knudsen effusion method, J. Chem. Soc., Faraday Trans. 1, 1974, 70, 0, 1569, https://doi.org/10.1039/f19747001569 . [all data]

de Kruif and Oonk, 1973
de Kruif, C.G.; Oonk, H.A.J., The determination of enthalpies of sublimation by means of thermal conductivity manometers, Chemie Ing. Techn., 1973, 45, 7, 455-461, https://doi.org/10.1002/cite.330450705 . [all data]

Malaspina, 1973
Malaspina, L., Microcalorimetric determination of the enthalpy of sublimation of benzoic acid and anthracene, J. Chem. Phys., 1973, 59, 1, 387, https://doi.org/10.1063/1.1679817 . [all data]

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Colomina, M.; Monzon, C.; Turrion, C.; Laynez, J., , Fifth Experimental Thermodynamics Conference, Lancaster, 1972. [all data]

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Ashcroft, 1971
Ashcroft, S.J., The measurement of enthalpies of sublimation by thermogravimetry, Thermochimica Acta, 1971, 2, 6, 512-514, https://doi.org/10.1016/0040-6031(71)80021-7 . [all data]

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Melia, T.P.; Merrifield, R., Vapour pressures of the tris(acetylacetonato) complexes of scandium(III), vanadium(III) and chromium(III), Journal of Inorganic and Nuclear Chemistry, 1970, 32, 5, 1489-1493, https://doi.org/10.1016/0022-1902(70)80636-4 . [all data]

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Mertl, I., Chem. Listy, 1968, 62, 5, 584. [all data]

Davies and Kybett, 1965
Davies, M.; Kybett, B., Sublimation and vaporization heats of long-chain alcohols, Trans. Faraday Soc., 1965, 61, 1608. [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.Z., Z. Phys. Chem. Abt. B, 1938, 39, 194. [all data]

Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Hirsbrunner, 1934
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Brittain, 2009
Brittain, Harry G., Vibrational Spectroscopic Studies of Cocrystals and Salts. 2. The Benzylamine-Benzoic Acid System, Crystal Growth & Design, 2009, 9, 8, 3497-3503, https://doi.org/10.1021/cg9001972 . [all data]

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Sharma, B.L.; Kant, Rajesh; Sharma, Ritu; Tandon, Sonika, Deviations of binary organic eutectic melt systems, Materials Chemistry and Physics, 2003, 82, 1, 216-224, https://doi.org/10.1016/S0254-0584(03)00199-8 . [all data]

Sharma, Jamwal, et al., 2004
Sharma, B.L.; Jamwal, R.; Kant, R., Thermodynamic and lamella models relationship for the eutectic system benzoic acid-- cinnamic acid, Cryst. Res. Technol., 2004, 39, 5, 454-464, https://doi.org/10.1002/crat.200310210 . [all data]

Roy, Riga, et al., 2002
Roy, S.; Riga, A.T.; Alexander, K.S., Experimental design aids the development of a differential scanning calorimetry standard test procedure for pharmaceuticals, Thermochimica Acta, 2002, 392-393, 399-404, https://doi.org/10.1016/S0040-6031(02)00317-9 . [all data]

Pitzer, Peiper, et al., 1984
Pitzer, Kenneth S.; Peiper, J. Christopher; Busey, R.H., Thermodynamic Properties of Aqueous Sodium Chloride Solutions, J. Phys. Chem. Ref. Data, 1984, 13, 1, 1, https://doi.org/10.1063/1.555709 . [all data]

Andon and Connett, 1980, 2
Andon, R.J.L.; Connett, J.E., Calibrants for thermal analysis. Measurement of their enthalpies of fusion by adiabatic calorimetry, Thermochim. Acta, 1980, 42, 241-247. [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
  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔsubS	Entropy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization

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