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
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• 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:
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

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

Gas Chromatography

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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

Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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]

Boule and Lemaire, 1977
Boule, P.; Lemaire, J., Compt. rend., 1977, 285, 305. [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, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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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