Maleic anhydride

• Formula: C₄H₂O₃
• Molecular weight: 98.0569
• IUPAC Standard InChI: InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H Copy

  
• IUPAC Standard InChIKey: FPYJFEHAWHCUMM-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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

 +  =

By formula: C₄H₂O₃ + C₁₄H₁₀ = C₁₈H₁₂O₃

 +  =

By formula: C₄H₂O₃ + C₅H₆O = C₉H₈O₄

 +  =

By formula: C₄H₂O₃ + H₂O = C₄H₄O₄

 +  = C₂₄H₁₆O₃

By formula: C₄H₂O₃ + C₂₀H₁₄ = C₂₄H₁₆O₃

=  + 

By formula: C₈H₈O₃ = C₄H₆ + C₄H₂O₃

 +  =

By formula: C₄H₂O₃ + C₄H₁₀O = C₈H₁₂O₄

 +  =

By formula: C₄H₆ + C₄H₂O₃ = C₈H₈O₃

 +  =

By formula: C₄H₂O₃ + C₃H₈O = propyl hydrogen maleate

 +  =

By formula: C₆H₆BrN + C₄H₂O₃ = C₁₀H₈BrNO₃

 +  =

By formula: C₆H₆ClN + C₄H₂O₃ = C₁₀H₈ClNO₃

=  + 

By formula: C₉H₂Cl₆O₃ = C₄H₂O₃ + C₅Cl₆

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

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (MINERAL OIL MULL); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLID (PELLET); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLID (SPLIT MULL, FLUOROLUBE FOR 3800-1330 AND NUJOL FOR 1330-400 CM ^-1); BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry 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.

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]

Boule and Lemaire, 1977
Boule, P.; Lemaire, J., Compt. rend., 1977, 285, 305. [all data]

Notes

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• 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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