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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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry data, 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: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 83.94 | 273.15 | Caminati W., 1985 | Other statistically calculated values are: S(298.15 K)=300.75 J/mol*K and Cp(298.15 K)=88.87 J/mol*K [ Joshi R.M., 1970]. |
| 90.04 | 298.15 | ||
| 128.54 | 500. | ||
| 159.65 | 800. |
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: 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 |
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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.440 ± 0.087 | TDEq | Paul and Kebarle, 1989 | ΔGea(423 K) = -32.8±1 kcal/mol, ΔS = -1±3 eu.; B |
| 1.440 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -32.7 kcal/mol; ΔSea =-1.3, est. from data in Paul and Kebarle, 1989; B |
| 1.40 ± 0.20 | NBIE | Compton, Reinhardt, et al., 1974 | Lifetime: Cooper and Compton, 1973; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 11.07 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
| 11.11 ± 0.05 | PE | Galasso, Colonna, et al., 1977 | Vertical value; LLK |
| 11.1 | PE | Almemark, Backvall, et al., 1974 | Vertical value; LLK |
| 11.45 | PE | Bain and Frost, 1973 | Vertical value; LLK |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, 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 | 827. | Radulovic, Blagojevic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
| Capillary | MDN-5 | 830. | van Loon, Linssen, et al., 2005 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 4. min, 4. K/min, 270. C @ 5. min |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | 833. | Brandi, Bar, et al., 2011 | Program: not specified | |
| Capillary | DB-1 | 791. | Delort and Jaquier, 2009 | 60. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (5 min) 3 0C/min -> 120 0C 5 0C/min -> 250 0C (3 min) 15 0C/min -> 300 0C (20 min) |
| Capillary | HP-1 | 790. | Teai, Claude-Lafontaine, et al., 2001 | 50. m/0.32 mm/0.52 μm, N2; Program: 40C => 2C/min => 130C => 4C/min => 250C |
References
Go To: Top, Gas phase thermochemistry data, 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.
Caminati W., 1985
Caminati W.,
A study of the ring-bending and ring-twisting motions in maleic anhydride by rotational analysis of the corresponding vibrational satellites,
Spectrochim. Acta, 1985, A41, 937-941. [all data]
Joshi R.M., 1970
Joshi R.M.,
Thermodynamic properties of some monomeric compounds in the standard ideal gas state,
J. Polym. Sci., Part A-2, 1970, 8, 679-687. [all data]
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]
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]
Compton, Reinhardt, et al., 1974
Compton, R.N.; Reinhardt, P.W.; Cooper, C.D.,
Mass spectrometry utilizing collisional ionization of cesium: Maleic anhydride and succinic anhydride,
J. Chem. Phys., 1974, 60, 2953. [all data]
Cooper and Compton, 1973
Cooper, C.D.; Compton, R.N.,
Electron attachment and cesium collisional ionization studies of tetrafluorosuccinic and hexafluoroglutaric anhydrides: Molecular electron affinities,
J. Chem. Phys., 1973, 59, 3550. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [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]
Almemark, Backvall, et al., 1974
Almemark, M.; Backvall, J.E.; Moberg, C.A.; Akermark, B.; Asbrink, L.; Roos, B.,
Ab initio calculations and assignment of photoelectron spectra of maleic and succinic anhydride,
Tetrahedron, 1974, 30, 2503. [all data]
Bain and Frost, 1973
Bain, A.D.; Frost, D.C.,
Studies of the carbonyl group in some five-membered ring compounds by photoelectron spectroscopy,
Can. J. Chem., 1973, 51, 1245. [all data]
Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R.,
Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae),
Molecules, 2010, 15, 9, 6168-6185, https://doi.org/10.3390/molecules15096168
. [all data]
van Loon, Linssen, et al., 2005
van Loon, W.A.M.; Linssen, J.P.H.; Legger, A.; Posthumus, M.A.; Voragen, A.G.J.,
Identification and olfactometry of French fries flavour extracted at mouth conditions,
Food Chem., 2005, 90, 3, 417-425, https://doi.org/10.1016/j.foodchem.2004.05.005
. [all data]
Brandi, Bar, et al., 2011
Brandi, F.; Bar, E.; Mourgues, F.; Horvath, G.; Turcsi, E.; Giuliano, G.; Liverani, A.; Tartarini, S.; Lewinsohn, E.; Rosati, C.,
Study of Redhaven peach and its white-fleshed mutant suggests a key role of CCD4 carotenoid dioxygenase in carotenoid and norisoprenoid volatile metabolism,
BMC Plant Biol., 2011, 11, 24, 1-14. [all data]
Delort and Jaquier, 2009
Delort, E.; Jaquier, A.,
Novel terpenyl esters from Australian finger lime (Citrus australasica) peel extract,
Flav. Fragr. J., 2009, 24, 3, 123-132, https://doi.org/10.1002/ffj.1922
. [all data]
Teai, Claude-Lafontaine, et al., 2001
Teai, T.; Claude-Lafontaine, A.; Schippa, C.; Cozzolino, F.,
Volatile compounds in fresh pulp of pineapple (Ananas comosus [L.] Merr.) from French Polynesia,
J. Essent. Oil Res., 2001, 13, 5, 314-318, https://doi.org/10.1080/10412905.2001.9712222
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas EA Electron affinity ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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