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
- 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
View 3d structure (requires JavaScript / HTML 5) - 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, 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 |
Mass spectrum (electron ionization)
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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: 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
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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: 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, 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]
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, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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