Phthalic anhydride
- Formula: C8H4O3
- Molecular weight: 148.1156
- IUPAC Standard InChIKey: LGRFSURHDFAFJT-UHFFFAOYSA-N
- 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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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics 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 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
By formula: C6H7N + C8H4O3 = C14H11NO3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -53.5 | kJ/mol | Kin | Kalnin'sh, 1988 | liquid phase; solvent: Acetonitrile |
ΔrH° | -54.4 | kJ/mol | Kin | Pravednikov, Kardash, et al., 1973 | solid phase; solvent: Tetrahydrofuran |
By formula: C8H6O4 = H2O + C8H4O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 31.93 ± 0.29 | kJ/mol | Cm | Alekseev, Kizaev, et al., 1989 | solid phase; solvent: Aqueous; Enthapy of anhydridisation |
C20H16N2O4 + = C28H20N2O7
By formula: C20H16N2O4 + C8H4O3 = C28H20N2O7
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -62.8 ± 0.4 | kJ/mol | Eqk | Karyakin, Rabinovich, et al., 1978 | liquid phase; solvent: DMF |
C21H16N2O4 + = C29H20N2O7
By formula: C21H16N2O4 + C8H4O3 = C29H20N2O7
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -31. ± 0.4 | kJ/mol | Eqk | Karyakin, Rabinovich, et al., 1978 | liquid phase; solvent: DMF |
+
= C26H20N2O5
By formula: C18H16N2O2 + C8H4O3 = C26H20N2O5
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -68.2 ± 0.4 | kJ/mol | Eqk | Karyakin, Rabinovich, et al., 1978 | liquid phase; solvent: DMF |
+
= C20H16N2O4
By formula: C12H12N2O + C8H4O3 = C20H16N2O4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -69.9 ± 0.4 | kJ/mol | Eqk | Karyakin, Rabinovich, et al., 1978 | liquid phase; solvent: DMF |
+
= C21H16N2O4
By formula: C13H12N2O + C8H4O3 = C21H16N2O4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -61.9 ± 0.4 | kJ/mol | Eqk | Karyakin, Rabinovich, et al., 1978 | liquid phase; solvent: DMF |
By formula: C8H4O3 + C12H12N2 = C20H16N2O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -67.4 ± 0.4 | kJ/mol | Eqk | Karyakin, Rabinovich, et al., 1978 | liquid phase; solvent: DMF |
+
= dodecyl hydrogen phthalate
By formula: C12H26O + C8H4O3 = dodecyl hydrogen phthalate
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -37.1 | kJ/mol | Kin | Fomin, Legkova, et al., 1981 | liquid phase; Monoesterification |
Gas phase ion energetics data
Go To: Top, 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 ± 0.087 | TDEq | Paul and Kebarle, 1989 | ΔGea(423 K) = -27.4±1 kcal/mol, ΔS = 3±3 eu; B |
1.279 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -28.4 kcal/mol; ΔSea =-3.0, est. from data in Paul and Kebarle, 1989; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.1 | PE | Dewar and Tien, 1985 | LBLHLM |
10.25 ± 0.05 | PE | Galasso, Colonna, et al., 1977 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H4+ | 13.2 ± 0.2 | ? | EI | Grutzmacher and Lohmann, 1967 | RDSH |
IR Spectrum
Go To: Top, 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, 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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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
UV/Visible spectrum
Go To: Top, 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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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, 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.
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, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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