Pyromellitic dianhydride
- Formula: C10H2O6
- Molecular weight: 218.1193
- IUPAC Standard InChI: InChI=1S/C10H2O6/c11-7-3-1-4-6(10(14)16-8(4)12)2-5(3)9(13)15-7/h1-2H
- IUPAC Standard InChIKey: ANSXAPJVJOKRDJ-UHFFFAOYSA-N
- CAS Registry Number: 89-32-7
- 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: 1,2,4,5-Benzenetetracarboxylic anhydride; 1,2,4,5-Benzenetetracarboxylic dianhydride; 1H,3H-Benzo[1,2-c:4,5-c']difuran-1,3,5,7-tetrone; Benzene-1,2:4,5-tetracarboxylic dianhydride; Pyromellitic acid anhydride; Pyromellitic acid dianhydride; Pyromellitic anhydride; 1,2,4,5-Benzenetetracarboxylic 1,2:4,5-dianhydride; NSC 4798; Pyromellitic 1,2:4,5-dianhydride
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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 |
|---|---|---|---|---|---|
| ΔfH°solid | -953.5 | kJ/mol | Ccb | Karyakin, Bazhan, et al., 1977 | ALS |
| ΔfH°solid | -1047. | kJ/mol | Ccb | Baroody and Carpenter, 1972 | High level of uncertainty in the data; ALS |
| ΔfH°solid | -907.34 | kJ/mol | Ccb | Mullayanov, Mukhutdinov, et al., 1967 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3267. ± 1. | kJ/mol | Ccb | Karyakin, Bazhan, et al., 1977 | Corresponding ΔfHºsolid = -953.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -3312.7 ± 9.1 | kJ/mol | Ccb | Mullayanov, Mukhutdinov, et al., 1967 | Corresponding ΔfHºsolid = -908.22 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 237.1 | J/mol*K | N/A | Dunn, Rahman, et al., 1978 | DH |
| S°solid,1 bar | 236.5 | J/mol*K | N/A | Karyakin, Mochalov, et al., 1973 | DH |
| S°solid,1 bar | 242.1 | J/mol*K | N/A | Karyakin, Bazhan, et al., 1977, 2 | DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 215.7 | 298.15 | Dunn, Rahman, et al., 1978 | T = 5 to 300 K.; DH |
| 231.4 | 298.15 | Marchidan and Ciopec, 1978 | T = 298 to 580 K.; DH |
| 219.9 | 300. | Karyakin, Bazhan, et al., 1977, 2 | T = 60 to 400 K.; DH |
| 219.9 | 300. | Karyakin, Mochalov, et al., 1973 | T = 20 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
2 +
=
By formula: 2H2O + C10H2O6 = C10H6O8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -71.5 ± 0.57 | kJ/mol | Cm | Alekseev, Kizaev, et al., 1989 | solid phase; solvent: Aqueous; Enthapy of anhydridisation |
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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference |
|---|---|---|
| 12.19 ± 0.02 | PI | Gorodyskii, Pozdnyakov, et al., 1974 |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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.
Karyakin, Bazhan, et al., 1977
Karyakin, N.V.; Bazhan, N.G.; Sapozhnikov, V.N.; Shvetsova, K.G.; Berestneva, G.L.; Lomteva, A.N.; Zimin, Yu.B.; Korshak, V.V.,
Thermodynamics of synthesis of poly-(p,p'-diphenyleneoxide)pyromellitimide,
Polym. Sci. USSR, 1977, 19, 1766-1775. [all data]
Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A.,
Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [all data]
Mullayanov, Mukhutdinov, et al., 1967
Mullayanov, F.I.; Mukhutdinov, R.Kh.; Mazitov, M.F.; Buz'ko, M.F.; Borshchenko, V.P.; Krashennikova, V.N.,
Some properties of pyromellitic dianhydride,
Khim. Prom. (Moscow), 1967, 43, 505-506. [all data]
Dunn, Rahman, et al., 1978
Dunn, A.G.; Rahman, A.; Staveley, L.A.K.,
The heat capacity of pyromellitic dianhydride and of its 1-1 charge-transfer complex with pyrene,
J. Chem. Thermodynam., 1978, 10, 787-796. [all data]
Karyakin, Mochalov, et al., 1973
Karyakin, N.V.; Mochalov, A.N.; Kunyevskaya, S.G.; Aron, B.M.; Rabinovich, I.B.,
Low temperature specific heat of tetracarboxylic acid dianhydrides,
Tr. Khim. Khim. Tekhnol, 1973, (1), 60-61. [all data]
Karyakin, Bazhan, et al., 1977, 2
Karyakin, N.V.; Bazhan, N.G.; Sapozhnikov, V.N.; Shvetsova, K.G.; Berestneva, G.L.; Lomteva, A.N.; Zimin, Yu.B.; Korshak, V.V.,
Thermodynamics of synthesis of poly-(p,p'-diphenylene oxide)pyromellitimide,
Vysokomol. Soedin., 1977, A19, 1541-1548. [all data]
Marchidan and Ciopec, 1978
Marchidan, D.I.; Ciopec, M.,
Thermodynamic properties of maleic, trimellitic and pyromellitic anhydrides,
Rev. Roum. Chim., 1978, 23, 19-29. [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]
Gorodyskii, Pozdnyakov, et al., 1974
Gorodyskii, V.A.; Pozdnyakov, V.P.; Siretskii, Yu.G.; Fadeeva, I.I.; Kozlov, L.P.,
The structures and properties of complexes of tetraitromethane and pyromellitic dianhydride with hydrocarbons of the benzene-tetracene series. II. Spectroscopic and thermodynamic characteristics,
Russ. J. Phys. Chem., 1974, 48, 1298, In original 2190. [all data]
Notes
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- 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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