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
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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Condensed phase thermochemistry data
Go To: Top, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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:
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 |
|---|---|---|---|---|---|
| ΔfH°solid | -460.37 | kJ/mol | Ccb | Parks, Mosley, et al., 1950 | see Richardson and Parks, 1939; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3259.4 | kJ/mol | Ccb | Parks, Mosley, et al., 1950 | see Richardson and Parks, 1939; Corresponding ΔfHºsolid = -460.32 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 180.0 | J/mol*K | N/A | Busygina, Maslova, et al., 1987 | DH |
| S°solid,1 bar | 179.5 | J/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 90 K, 58.12 J/mol*K.; DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 160.0 | 298.15 | Busygina, Maslova, et al., 1987 | T = 13 to 350 K.; DH |
| 161.80 | 298.1 | Parks, Todd, et al., 1936 | T = 90 to 300 K.; DH |
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
+
=
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 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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 |
Gas Chromatography
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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
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 MS | 1313. | Kotowska, Zalikowski, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium, 35. C @ 5. min, 3. K/min, 300. C @ 15. min |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 MS | 1319. | Kotowska, Zalikowski, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 225.33 | Pedersen, Durant, et al., 2005 | 30. m/0.25 mm/0.25 μm, Helium, 50. C @ 1.5 min, 6. K/min, 310. C @ 10. min |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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]
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]
Kotowska, Zalikowski, et al., 2012
Kotowska, U.; Zalikowski, M.; Isidorov, V.A.,
HS-SPME/GC-MS analysis of volatile and semi-volatile organic compounds emitted from municipal sewage sludge,
Environ. Monit. Asses., 2012, 184, 5, 2893-2907, https://doi.org/10.1007/s10661-011-2158-8
. [all data]
Pedersen, Durant, et al., 2005
Pedersen, D.U.; Durant, J.L.; Taghizadeh, K.; Hemond, H.F.; Lafleur, A.L.; Cass, G.R.,
Human cell mutagenes in respirable airborne particles from the Northeastern United States. 2. Quantification of mutagenes and other organic compounds.,
Environ. Sci. Technol., 2005, 39, 24, 9547-9560, https://doi.org/10.1021/es050886c
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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