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Phthalic anhydride

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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

Quantity Value Units Method Reference Comment
Deltafsolid-460.37kJ/molCcbParks, Mosley, et al., 1950see Richardson and Parks, 1939; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-3259.4kJ/molCcbParks, Mosley, et al., 1950see Richardson and Parks, 1939; Corresponding «DELTA»fsolid = -460.32 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar180.0J/mol*KN/ABusygina, Maslova, et al., 1987DH
solid,1 bar179.5J/mol*KN/AParks, Todd, et al., 1936Extrapolation below 90 K, 58.12 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
160.0298.15Busygina, Maslova, et al., 1987T = 13 to 350 K.; DH
161.80298.1Parks, Todd, et al., 1936T = 90 to 300 K.; DH

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

Quantity Value Units Method Reference Comment
Tboil557.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil558.25KN/ABurriel, 1931Uncertainty assigned by TRC = 0.3 K; TRC
Tboil557.83KN/ABurriel, 1931Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tfus404. ± 3.KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Deltasub88.7 ± 2.3kJ/molVCrooks and Freetham, 1946ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
52.1422.AStephenson and Malanowski, 1987Based on data from 407. - 558. K.; AC
63.9 ± 2.5422.GSDas, Dharwadkar, et al., 1979Based on data from 411. - 450. K.; AC
54.1521.N/AMonroe, 1920Based on data from 485. - 557. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
369.7 - 557.73.107621249.606-159.288Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
87.9348.AStephenson and Malanowski, 1987Based on data from 313. - 383. K. See also Amitin, Vakurova, et al., 1972.; AC
84.4 ± 1.2388.GSDas, Dharwadkar, et al., 1979Based on data from 333. - 403. K.; AC
88.4 ± 1.2318.N/ACrooks and Feetham, 1946Based on data from 303. - 333. K. See also Cox and Pilcher, 1970 and Jones, 1960.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
23.09403.3DSCAcree, 1991See also Donnelly, Drewes, et al., 1990.; AC
22.1404.5DSCDas, Dharwadkar, et al., 1979AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction 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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

Aniline + Phthalic anhydride = Benzoic acid, 2-[(phenylamino)carbonyl]-

By formula: C6H7N + C8H4O3 = C14H11NO3

Quantity Value Units Method Reference Comment
Deltar-53.5kJ/molKinKalnin'sh, 1988liquid phase; solvent: Acetonitrile
Deltar-54.4kJ/molKinPravednikov, Kardash, et al., 1973solid phase; solvent: Tetrahydrofuran

1,2-Benzenedicarboxylic acid = Water + Phthalic anhydride

By formula: C8H6O4 = H2O + C8H4O3

Quantity Value Units Method Reference Comment
Deltar31.93 ± 0.29kJ/molCmAlekseev, Kizaev, et al., 1989solid phase; solvent: Aqueous; Enthapy of anhydridisation

C20H16N2O4 + Phthalic anhydride = C28H20N2O7

By formula: C20H16N2O4 + C8H4O3 = C28H20N2O7

Quantity Value Units Method Reference Comment
Deltar-62.8 ± 0.4kJ/molEqkKaryakin, Rabinovich, et al., 1978liquid phase; solvent: DMF

C21H16N2O4 + Phthalic anhydride = C29H20N2O7

By formula: C21H16N2O4 + C8H4O3 = C29H20N2O7

Quantity Value Units Method Reference Comment
Deltar-31. ± 0.4kJ/molEqkKaryakin, Rabinovich, et al., 1978liquid phase; solvent: DMF

Aniline, p,p'-(p-phenylenedioxy)di- + Phthalic anhydride = C26H20N2O5

By formula: C18H16N2O2 + C8H4O3 = C26H20N2O5

Quantity Value Units Method Reference Comment
Deltar-68.2 ± 0.4kJ/molEqkKaryakin, Rabinovich, et al., 1978liquid phase; solvent: DMF

Benzenamine, 4,4'-oxybis- + Phthalic anhydride = C20H16N2O4

By formula: C12H12N2O + C8H4O3 = C20H16N2O4

Quantity Value Units Method Reference Comment
Deltar-69.9 ± 0.4kJ/molEqkKaryakin, Rabinovich, et al., 1978liquid phase; solvent: DMF

4,4'-Diaminobenzophenone + Phthalic anhydride = C21H16N2O4

By formula: C13H12N2O + C8H4O3 = C21H16N2O4

Quantity Value Units Method Reference Comment
Deltar-61.9 ± 0.4kJ/molEqkKaryakin, Rabinovich, et al., 1978liquid phase; solvent: DMF

Phthalic anhydride + Benzidine = Benzoic acid, 2-[[(4'-amino[1,1'-biphenyl]-4-yl)amino]carbonyl]-

By formula: C8H4O3 + C12H12N2 = C20H16N2O3

Quantity Value Units Method Reference Comment
Deltar-67.4 ± 0.4kJ/molEqkKaryakin, Rabinovich, et al., 1978liquid phase; solvent: DMF

1-Dodecanol + Phthalic anhydride = dodecyl hydrogen phthalate

By formula: C12H26O + C8H4O3 = dodecyl hydrogen phthalate

Quantity Value Units Method Reference Comment
Deltar-37.1kJ/molKinFomin, Legkova, et al., 1981liquid phase; Monoesterification

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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:
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

EA (eV) Method Reference Comment
1.245 ± 0.087TDEqPaul and Kebarle, 1989«DELTA»Gea(423 K) = -27.4±1 kcal/mol, «DELTA»S = 3±3 eu; B
1.279 ± 0.048IMREFukuda and McIver, 1985«DELTA»Gea(355 K) = -28.4 kcal/mol; «DELTA»Sea =-3.0, est. from data in Paul and Kebarle, 1989; B

Ionization energy determinations

IE (eV) Method Reference Comment
10.1PEDewar and Tien, 1985LBLHLM
10.25 ± 0.05PEGalasso, Colonna, et al., 1977Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H4+13.2 ± 0.2?EIGrutzmacher and Lohmann, 1967RDSH

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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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Mass spectrum
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Additional Data

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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 NIST Mass Spectrometry Data Center, 1994
NIST MS number 133911

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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 by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Bartecki, Szoke, et al., 1975
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 6044
Instrument Carl Zeiss spectrophotometer
Melting point 130.8
Boiling point 295

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

Kalnin'sh, 1988
Kalnin'sh, K.K., Autocatalysis and effects of the solvent in the reaction of phthalic anhydride with aniline derivatives, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 1768-1773. [all data]

Pravednikov, Kardash, et al., 1973
Pravednikov, A.N.; Kardash, I.Ye.; Glukhoyedov, N.P.; Ardashnikov, A.Ya., Some features of the synthesis of heat-resistant heterocyclic polymers, Polym. Sci. USSR, 1973, 15, 399-410. [all data]

Alekseev, Kizaev, et al., 1989
Alekseev, V.G.; Kizaev, V.D.; Fedyainov, N.V.; Bushinskii, V.I., Standard enthalpies of anhydridisation of phthalic and pyromellitic acids, Russ. J. Phys. Chem. (Engl. Transl.), 1989, 63, 1280-1282. [all data]

Karyakin, Rabinovich, et al., 1978
Karyakin, N.V.; Rabinovich, I.B.; Pal'tseva, N.G., Thermodynamics of the reactions of aromatic diamines with dianhydrides of tetracarboxylic acids, Polym. Sci. USSR, 1978, 20, 2274-2279. [all data]

Fomin, Legkova, et al., 1981
Fomin, a.S.; Legkova, T.N.; Morgunov, A.V.; Ignatov, V.A., Study of the kinetics of the reaction between phthalic anhydride and lauryl alcohol, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1981, 24, 1180-1182. [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]

Bartecki, Szoke, et al., 1975
Bartecki, A.; Szoke, J.; Varsanyi, G.; Vizesy, M., Absorption spectra in the ultraviolet and visible region. Volume 20, Academic Press Inc., New York, 1975, 254. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References