Phthalic anhydride

• Formula: C₈H₄O₃
• Molecular weight: 148.1156
• IUPAC Standard InChI: InChI=1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H Copy

  
• IUPAC Standard InChIKey: LGRFSURHDFAFJT-UHFFFAOYSA-N Copy
• CAS Registry Number: 85-44-9
• 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: 1,3-Isobenzofurandione; ESEN; Phthalandione; Phthalic acid anhydride; Retarder AK; Retarder ESEN; Retarder PD; TGL 6525; Vulkalent B/C; 1,2-Benzenedicarboxylic anhydride; 1,3-Phthalandione; 1,2-Benzenedicarboxylic acid anhydride; 1,3-Dioxophthalan; o-Phthalic acid anhydride; Anhydride phtalique; Anidride ftalica; Ftaalzuuranhydride; Ftalowy bezwodnik; Isobenzofuran, 1,3-dihydro-1,3-dioxo-; NCI-C03601; Phthalsaeureanhydrid; Anhydrid kyseliny ftalove; Ftalanhydrid; Rcra waste number U190; Araldite HT 901; Phthalanhydride; Sconoc 7; HT 901; Isobenzofuran-1,3-dione; Retarder PX; NSC 10431
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • 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 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 solid

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 (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics 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:
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
B - John E. Bartmess

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

References

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

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

Parks, Mosley, et al., 1950
Parks, G.S.; Mosley, J.R.; Peterson, P.V., Jr., Heats of combustion and formation of some organic compounds containing oxygen, J. Chem. Phys., 1950, 18, 152. [all data]

Richardson and Parks, 1939
Richardson, J.W.; Parks, G.S., Thermal data on organic compounds. XIX. Modern combustion data for some non-volatile compounds containing carbon, hydrogen and oxygen, J. Am. Chem. Soc., 1939, 61, 3543-3546. [all data]

Busygina, Maslova, et al., 1987
Busygina, G.I.; Maslova, V.A.; Shvetsova, K.G.; Babinkov, A.G.; Rabinovich, I.B.; Karyakin, N.V., Specific heat and thermodynamic functions of phthalic anhydride and 2-ethylhexanol at 13-350 K, Zhur. Fiz. Khim., 1987, 61, 2347-2351. [all data]

Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Moore, W.A., Thermal data on organic compounds. XVI. Some heat capacity, entropy and free energy data for typical benzene derivatives and heterocyclic compounds, J. Am. Chem. Soc., 1936, 58, 398-401. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 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]

Crooks and Freetham, 1946
Crooks, D.A.; Freetham, F.M., The vapour pressure of phthalic anhydride, J. Chem. Soc., 1946, 899-901. [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]

Das, Dharwadkar, et al., 1979
Das, D.; Dharwadkar, S.R.; Chandrasekharaiah, M.S., Vapour pressure of phthalic anhydride, Thermochimica Acta, 1979, 30, 1-2, 371-376, https://doi.org/10.1016/0040-6031(79)85076-5 . [all data]

Monroe, 1920
Monroe, K.P., Phthalic Anhydride. IV---The Vapor Pressure of Phthalic Anhydride, J. Ind. Eng. Chem., 1920, 12, 10, 969-971, https://doi.org/10.1021/ie50130a013 . [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]

Amitin, Vakurova, et al., 1972
Amitin, A.V.; Vakurova, E.A.; Katunin, V.Kh.; Afanas'eva, N.S., Zh. Fiz. Khim., 1972, 46, 4, 1054. [all data]

Crooks and Feetham, 1946
Crooks, D.A.; Feetham, F.M., 196. The vapour pressure of phthalic anhydride, J. Chem. Soc., 1946, 899, https://doi.org/10.1039/jr9460000899 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Donnelly, Drewes, et al., 1990
Donnelly, J.R.; Drewes, L.A.; Johnson, R.L.; Munslow, W.D.; Knapp, K.K.; Sovocool, G.W., Purity and heat of fusion data for environmental standards as determined by differential scanning calorimetry, Thermochimica Acta, 1990, 167, 2, 155-187, https://doi.org/10.1016/0040-6031(90)80476-F . [all data]

Paul and Kebarle, 1989
Paul, G.; Kebarle, P., Electron Affinities of Cyclic Unsaturated Dicarbonyls: Maleic Anhydrides, Maleimides, and Cyclopentendione, J. Am. Chem. Soc., 1989, 111, 2, 464, https://doi.org/10.1021/ja00184a009 . [all data]

Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr., Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO₂) from 74CEL/BEN], J. Am. Chem. Soc., 1985, 107, 2291. [all data]

Dewar and Tien, 1985
Dewar, M.J.S.; Tien, T.-P., Photoelectron spectrum of benzyne, J. Chem. Soc., Chem. Commun., 1985, 1243. [all data]

Galasso, Colonna, et al., 1977
Galasso, V.; Colonna, F.P.; Distefano, G., Photoelectron spectra of 1,2-indandione, 1,3-indandione and heterocyclic analogues, J. Electron Spectrosc. Relat. Phenom., 1977, 10, 227. [all data]

Grutzmacher and Lohmann, 1967
Grutzmacher, H.-F.; Lohmann, J., Massenspektrometrie instabiler organischer Molekule. I. Ionisations-potential und Bildungsenthalpie von Dehydrobenzol, Ann. Chem., 1967, 705, 81. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,solid	Constant pressure heat capacity of solid
  EA	Electron affinity
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  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
  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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