Benzoic acid, anhydride

• Formula: C₁₄H₁₀O₃
• Molecular weight: 226.2274
• IUPAC Standard InChI: InChI=1S/C14H10O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h1-10H Copy

  
• IUPAC Standard InChIKey: CHIHQLCVLOXUJW-UHFFFAOYSA-N Copy
• CAS Registry Number: 93-97-0
• 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: Benzoic anhydride; Benzoyl anhydride; Benzoyl benzoate
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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:
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy 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.

Carson, Fine, et al., 1971
Carson, A.S.; Fine, D.H.; Gray, P.; Laye, P.G., Standard enthalpies of formation of diphenyl oxalate and benzoic anhydride and some related bond dissociation energies, J. Chem. Soc. B, 1971, 1611-1615. [all data]

Breitenbach and Derkosch, 1951
Breitenbach, J.W.; Derkosch, J., Verbrennungswarmen von peroxyden und verwandten verbindungen sowie von polystrolen, Monatsh. Chem., 1951, 82, 177-179. [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]

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]

Lumsden, 1905
Lumsden, J.S., The physical properties of heptoic, hexahydrobenzoic, and benzoic acids and their derivatives, J. Chem. Soc., 1905, 87, 90-98. [all data]

Paetzold and Aurich, 1962
Paetzold, R.; Aurich, K., Polymorphism ob Benzoic Anhydride, Chem. Ber., 1962, 95, 2645-51. [all data]

Adams, Wirth, et al., 1918
Adams, R.; Wirth, W.N.; French, H.E., Oxalyl Chloride As A Reagent in Organic Chemistry II. Preparation of Aromatic Acid Anhydrides; Reaction with Alcohols, J. Am. Chem. Soc., 1918, 40, 424-31. [all data]

Carson, Fine, et al., 1971, 2
Carson, A.S.; Fine, D.H.; Gray, P.; Laye, P.G., Standard enthalpies of formation of diphenyl oxalate and benzoic anhydride and some related bond dissociation energies, J. Chem. Soc., B:, 1971, 1611, https://doi.org/10.1039/j29710001611 . [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., , Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [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]

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]

Notes

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

• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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