Maleic anhydride
- Formula: C4H2O3
- Molecular weight: 98.0569
- IUPAC Standard InChI: InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H
- IUPAC Standard InChIKey: FPYJFEHAWHCUMM-UHFFFAOYSA-N
- CAS Registry Number: 108-31-6
- 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: 2,5-Furandione; cis-Butenedioic anhydride; Dihydro-2,5-dioxofuran; Maleic acid anhydride; Toxilic anhydride; Maleic anhydride, briquettes; Anhydrid kyseliny maleinove; Maleinanhydrid; Rcra waste number U147; UN 2215; 2,5-Furanedione; M 188; NSC 137651
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Reaction thermochemistry data
Go To: Top, 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: C4H2O3 + C5H6 = C9H8O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -104. ± 2. | kJ/mol | Cm | Breslauer and Kabakoff, 1974 | liquid phase; solvent: Dioxane |
| ΔrH° | -107.9 | kJ/mol | Cm | Rogers and Quan, 1973 | liquid phase; Gas phase Diels-Alder |
+
=
By formula: C4H2O3 + C14H10 = C18H12O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -93. ± 2. | kJ/mol | Cm | Kiselev, Mavrin, et al., 1982 | liquid phase; solvent: Benzene |
| ΔrH° | -93.7 | kJ/mol | Eqk | Lenz, Hegedus, et al., 1982 | liquid phase; solvent: 1,2,4-C6H3Cl3 |
+
=
By formula: C4H2O3 + C5H6O = C9H8O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -58.5 | kJ/mol | Cm | Balbi, 1991 | liquid phase; solvent: Dioxane |
| ΔrH° | -60. | kJ/mol | Cm | Sparks and Poling, 1983 | solid phase; solvent: Dioxane |
+
=
By formula: C4H2O3 + H2O = C4H4O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -34.9 ± 0.8 | kJ/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydroysis at 303 K |
+
= C24H16O3
By formula: C4H2O3 + C20H14 = C24H16O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -427.2 | kJ/mol | Eqk | Lenz, Hegedus, et al., 1982 | liquid phase; solvent: 1,2,4-C6H3Cl3 |
=
+
By formula: C8H8O3 = C4H6 + C4H2O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 283.62 ± 0.96 | kJ/mol | Cm | Ghitau, Ciopec, et al., 1983 | solid phase; At 65 to 90°C |
+
=
By formula: C4H2O3 + C4H10O = C8H12O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -39. | kJ/mol | Kin | Merca, Poraicu, et al., 1978 | solid phase; solvent: n-Butanol; DTA |
+
=
By formula: C4H6 + C4H2O3 = C8H8O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -283.62 | kJ/mol | Cm | Ghitau, Ciopec, et al., 1983 | liquid phase |
+
=
By formula: C4H2O3 + C3H8O = propyl hydrogen maleate
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -35. | kJ/mol | Kin | Tribunescu, Poraicu, et al., 1978 | liquid phase |
+
=
By formula: C6H6BrN + C4H2O3 = C10H8BrNO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 14. | kJ/mol | Cm | Srivastava, 1979 | solid phase |
+
=
By formula: C6H6ClN + C4H2O3 = C10H8ClNO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 13. | kJ/mol | Cm | Srivastava, 1979 | solid phase |
=
+
By formula: C9H2Cl6O3 = C4H2O3 + C5Cl6
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 315. | kJ/mol | Ion | Vijayakumar and Fink, 1983 | solid phase |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Breslauer and Kabakoff, 1974
Breslauer, K.J.; Kabakoff, D.S.,
Enthalpy of the Diels-Alder reaction of cyclopentadiene and maleic anhydride,
J. Org. Chem., 1974, 39, 721-722. [all data]
Rogers and Quan, 1973
Rogers, F.E.; Quan, S.W.,
Thermochemistry of the Diels-Alder reaction. III. Heat of addition of cyclopentadience to maleic anhydride,
J. Phys. Chem., 1973, 77, 828-831. [all data]
Kiselev, Mavrin, et al., 1982
Kiselev, V.D.; Mavrin, G.V.; Konovalov, A.I.,
Thermodynamic principles of the occurrence of a Diels-Alder reaction in the presence of a Lewis acid,
Zh. Org. Khim., 1982, 18, 2505-2510. [all data]
Lenz, Hegedus, et al., 1982
Lenz, T.G.; Hegedus, L.S.; Vaughan, J.D.,
Liquid phase thermochemical energy conversion systems - an application of Diels-Alder chemistry,
Int. J. Energy Res., 1982, 6, 357-365. [all data]
Balbi, 1991
Balbi, N.,
Dynamic calorimetry in the study of Diels-Alder reaction,
Calorim. Anal. Therm., 1991, 22, 299-304. [all data]
Sparks and Poling, 1983
Sparks, B.G.; Poling, B.E.,
Energy storage capacity of reversible liquid-phase Diels Alder reaction between maleic anhydride and 2-methyl furan,
Am. Inst. Chem. Eng. Symp. Ser. (AIChE Symp. Ser.), 1983, 29, 534-537. [all data]
Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A.,
Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides,
J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]
Ghitau, Ciopec, et al., 1983
Ghitau, M.; Ciopec, M.; Pintea, O.,
Study on Diels-Alder reaction for the synthesis of tetrahydrophthalic anhydride,
Rev. Chim. (Bucharest), 1983, 34, 299-305. [all data]
Merca, Poraicu, et al., 1978
Merca, E.; Poraicu, M.; Tribunescu, P.,
Kinetics of maleic monoester formation with n-butanol,
Bull. Stiint. Teh. Inst. Politeh. "Traian Vuia" Timisoara, Ser. Chim., 1978, 23, 160-163. [all data]
Tribunescu, Poraicu, et al., 1978
Tribunescu, P.; Poraicu, M.; Merca, E.; Facsko, O.,
Kinetics of mono-N-propylmaleate synthesis,
Bull. Stiint. Teh. Inst. Politeh. "Traian Vuia" Timisoara, Ser. Chim., 1978, 23, 147-151. [all data]
Srivastava, 1979
Srivastava, A.K.,
Solid-state reactions between maleic anhydride and substituted aromactic amines,
Z. Phys. Chem. (Leipzig), 1979, 260, 630-640. [all data]
Vijayakumar and Fink, 1983
Vijayakumar, C.T.; Fink, J.K.,
Heat of formation of the Diels-Alder adduct of hexachlorocyclopentadiene and maleic anhydride by appearance-energy measurements,
Org. Mass Spectrom., 1983, 18, 134. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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