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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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, 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 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° | -12.8 | kcal/mol | Kin | Kalnin'sh, 1988 | liquid phase; solvent: Acetonitrile |
| ΔrH° | -13.0 | kcal/mol | Kin | Pravednikov, Kardash, et al., 1973 | solid phase; solvent: Tetrahydrofuran |
=
+
By formula: C8H6O4 = H2O + C8H4O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 7.631 ± 0.069 | kcal/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° | -15.0 ± 0.1 | kcal/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° | -7.5 ± 0.1 | kcal/mol | Eqk | Karyakin, Rabinovich, et al., 1978 | liquid phase; solvent: DMF |
+
= C26H20N2O5
By formula: C18H16N2O2 + C8H4O3 = C26H20N2O5
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -16.3 ± 0.1 | kcal/mol | Eqk | Karyakin, Rabinovich, et al., 1978 | liquid phase; solvent: DMF |
+
= C20H16N2O4
By formula: C12H12N2O + C8H4O3 = C20H16N2O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -16.7 ± 0.1 | kcal/mol | Eqk | Karyakin, Rabinovich, et al., 1978 | liquid phase; solvent: DMF |
+
= C21H16N2O4
By formula: C13H12N2O + C8H4O3 = C21H16N2O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -14.8 ± 0.1 | kcal/mol | Eqk | Karyakin, Rabinovich, et al., 1978 | liquid phase; solvent: DMF |
+
=
By formula: C8H4O3 + C12H12N2 = C20H16N2O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -16.1 ± 0.1 | kcal/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° | -8.87 | kcal/mol | Kin | Fomin, Legkova, et al., 1981 | liquid phase; Monoesterification |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, 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:
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 |
Gas Chromatography
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, 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
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, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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]
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, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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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