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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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 | -110.03 | kcal/mol | Ccb | Parks, Mosley, et al., 1950 | see Richardson and Parks, 1939; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -779.02 | kcal/mol | Ccb | Parks, Mosley, et al., 1950 | see Richardson and Parks, 1939; Corresponding ΔfHºsolid = -110.02 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 43.02 | cal/mol*K | N/A | Busygina, Maslova, et al., 1987 | DH |
S°solid,1 bar | 42.90 | cal/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 (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.24 | 298.15 | Busygina, Maslova, et al., 1987 | T = 13 to 350 K.; DH |
38.671 | 298.1 | Parks, Todd, et al., 1936 | T = 90 to 300 K.; DH |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 557.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 558.25 | K | N/A | Burriel, 1931 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tboil | 557.83 | K | N/A | Burriel, 1931 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 404. ± 3. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 21.19 ± 0.56 | kcal/mol | V | Crooks and Freetham, 1946 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.5 | 422. | A | Stephenson and Malanowski, 1987 | Based on data from 407. to 558. K.; AC |
15.3 ± 0.60 | 422. | GS | Das, Dharwadkar, et al., 1979 | Based on data from 411. to 450. K.; AC |
12.9 | 521. | N/A | Monroe, 1920 | Based on data from 485. to 557. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
369.7 to 557.7 | 3.10191 | 1249.606 | -159.288 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
21.0 | 348. | A | Stephenson and Malanowski, 1987 | Based on data from 313. to 383. K. See also Amitin, Vakurova, et al., 1972.; AC |
20.2 ± 0.29 | 388. | GS | Das, Dharwadkar, et al., 1979 | Based on data from 333. to 403. K.; AC |
21.1 ± 0.29 | 318. | N/A | Crooks and Feetham, 1946 | Based on data from 303. to 333. K. See also Cox and Pilcher, 1970 and Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
5.519 | 403.3 | DSC | Acree, 1991 | See also Donnelly, Drewes, et al., 1990.; AC |
5.28 | 404.5 | DSC | Das, Dharwadkar, et al., 1979 | AC |
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° | -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
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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:
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
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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)
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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
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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, Condensed phase thermochemistry data, Phase change data, 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.
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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Burriel, 1931
Burriel, F.,
Physico-Chemical Study of Some Solid Organic Compounds at Ordinary Temperatures, and Their COrrelationo with Temperature,
An. R. Soc. Esp. Fis. Quim., 1931, 29, 89. [all data]
Crooks and Freetham, 1946
Crooks, D.A.; Freetham, F.M.,
The vapour pressure of phthalic anhydride,
J. Chem. Soc., 1946, 899-901. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Das, Dharwadkar, et al., 1979
Das, D.; Dharwadkar, S.R.; Chandrasekharaiah, M.S.,
Vapour pressure of phthalic anhydride,
Thermochimica Acta, 1979, 30, 1-2, 371-376, https://doi.org/10.1016/0040-6031(79)85076-5
. [all data]
Monroe, 1920
Monroe, K.P.,
Phthalic Anhydride. IV---The Vapor Pressure of Phthalic Anhydride,
J. Ind. Eng. Chem., 1920, 12, 10, 969-971, https://doi.org/10.1021/ie50130a013
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Amitin, Vakurova, et al., 1972
Amitin, A.V.; Vakurova, E.A.; Katunin, V.Kh.; Afanas'eva, N.S.,
Zh. Fiz. Khim., 1972, 46, 4, 1054. [all data]
Crooks and Feetham, 1946
Crooks, D.A.; Feetham, F.M.,
196. The vapour pressure of phthalic anhydride,
J. Chem. Soc., 1946, 899, https://doi.org/10.1039/jr9460000899
. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Donnelly, Drewes, et al., 1990
Donnelly, J.R.; Drewes, L.A.; Johnson, R.L.; Munslow, W.D.; Knapp, K.K.; Sovocool, G.W.,
Purity and heat of fusion data for environmental standards as determined by differential scanning calorimetry,
Thermochimica Acta, 1990, 167, 2, 155-187, https://doi.org/10.1016/0040-6031(90)80476-F
. [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]
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, Condensed phase thermochemistry data, Phase change data, 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 Cp,solid Constant pressure heat capacity of solid EA Electron affinity S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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