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
Go To: Top, Phase change 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 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 |
Phase change data
Go To: Top, Condensed phase thermochemistry 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 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° | 88.7 ± 2.3 | kJ/mol | V | Crooks and Freetham, 1946 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
52.1 | 422. | A | Stephenson and Malanowski, 1987 | Based on data from 407. to 558. K.; AC |
63.9 ± 2.5 | 422. | GS | Das, Dharwadkar, et al., 1979 | Based on data from 411. to 450. K.; AC |
54.1 | 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 (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
369.7 to 557.7 | 3.10762 | 1249.606 | -159.288 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
87.9 | 348. | A | Stephenson and Malanowski, 1987 | Based on data from 313. to 383. K. See also Amitin, Vakurova, et al., 1972.; AC |
84.4 ± 1.2 | 388. | GS | Das, Dharwadkar, et al., 1979 | Based on data from 333. to 403. K.; AC |
88.4 ± 1.2 | 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 (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
23.09 | 403.3 | DSC | Acree, 1991 | See also Donnelly, Drewes, et al., 1990.; AC |
22.1 | 404.5 | DSC | Das, Dharwadkar, et al., 1979 | AC |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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) 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 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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