Maleic anhydride

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Maleic anhydride[1]
Maleic anhydride
Maleic anhydride-3d.png
IUPAC name Furan-2,5-dione
Identifiers
InChI InChI=1/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H
InChIKey FPYJFEHAWHCUMM-UHFFFAOYAP
Standard InChI InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H
Standard InChIKey FPYJFEHAWHCUMM-UHFFFAOYSA-N
CAS number [108-31-6]
EC number 203-571-6
RTECS UE5950000
ChemSpider 7635
SMILES
Properties[2][3][4][5]
Chemical formula C4H2O3
Molar mass 98.057 g/mol
Appearance White crystals
Density 1.48 g/cm3
Melting point

53 °C, 326.0 K, 127 °F

Boiling point

200 °C, 473.2 K, 392 °F

Triple point 52.57 ºC (325.72 K)
Solubility in water reacts
Thermochemistry[6]
Std enthalpy of formation ΔfHo298 470.0 kJ/mol
Std enthalpy of combustion ΔcHo298 1389.9 kJ/mol
Std enthalpy of fusion ΔfusHo298 13.6 kJ/mol
Std enthalpy of vaporization ΔvapHo298 54.8 kJ/mol
Hazards[2][4][7]
Material safety data sheet (MSDS) ICSC 0799
EU index number 607-096-00-9
GHS pictograms The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H302, H314, H334, H317
Flash point 102 °C (216 ºF)
Autoignition temp. 477 ºC (891 ºF)
Explosive limits 1.4–7.1%
PEL (U.S.) 1 mg/m3 TWA
IDLH level 10 mg/m3 TWA
Related compounds
Other acid anhydrides Succinic anhydride
Other compounds Maleic acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Maleic anhydride (cis-butenedioic anhydride, toxilic anhydride, dihydro-2,5-dioxofuran) is an organic compound with the formula C4H2O3. In its pure state it is a colourless or white solid with an acrid odour.

Maleic anhydride was traditionally manufactured by the oxidation of benzene or other aromatic compounds. As of 2006, only a few smaller plants continue to use benzene; due to rising benzene prices, most maleic anhydride plants now use n-butane as a feedstock:

2 CH3CH2CH2CH3 + 7 O2 → 2 C2H2(CO)2O + 8 H2O

Characteristic reactions

The chemistry of maleic anhydride is very rich, reflecting its ready availability and bifunctional reactivity.

  • It hydrolyzes, producing maleic acid, cis-HO2CCH=CHCO2H. With alcohols, the half-ester is generated, e.g., cis-HO2CCH=CHCO2CH3.
  • Maleic anhydride is a potent dienophile in Diels-Alder reactions.
  • Maleic anhydride (MA) is an excellent ligand for low-valent metal complexes, examples being Pt(PPh3)2(MA) and Fe(CO)4(MA).

References

  1. ↑ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 11th ed.; Merck, 1989. ISBN 091191028X, 5586
  2. ↑ 2.0 2.1 Maleic anhydride; International Chemical Safety Card 0799; International Labour Organization: Geneva, October 2005, <http://www.inchem.org/documents/icsc/icsc/eics0799.htm>.
  3. ↑ 2,5-Furandione. In NIST Chemistry WebBook; National Institute for Standards and Technology, <http://webbook.nist.gov/cgi/inchi/InChI%3D1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H>. (accessed 21 August 2009).
  4. ↑ 4.0 4.1 Maleic anhydride. In Pocket Guide to Chemical Hazards; U.S. Department of Health and Human Services (NIOSH) Publication No. 2005-149; Government Printing Office: Washington, DC, 2005. ISBN 9780160727511, <http://www.cdc.gov/niosh/npg/npgd0376.html>.
  5. ↑ DeWit, H. G. M.; DeKruif, C. G.; Van Miltenburg, J. C. Thermodynamic properties of molecular organic crystals containing organic crystals containing nitrogen, oxygen, and sulfur. II. Molar heat capacities of eight compounds by adiabatic calorimetry. J. Chem. Thermodynam. 1983, 15 (9), 891–902. DOI: 10.1016/0021-9614(83)90095-2.
  6. ↑ Winstrom, Leon O.; Kulp, Laurence Vapor pressure of maleic anhydride. Ind. Eng. Chem. 1949, 41 (11), 1584-86. DOI: 10.1021/ie50479a044. Parks, George S.; Mosley, John R.; Peterson, Peter V., Jr. Heats of combustion and formation of some organic compounds containing oxygen. J. Chem. Phys. 1950, 18 (1), 152–53. DOI: 10.1063/1.1747444. Mastrangelo, S. V. R. Adiabatic calorimeter for determination of cryoscopic data. Anal. Chem. 1957, 29 (5), 841–45. DOI: 10.1021/ac60125a032. Wilhoit, R. C.; Shiao, Daniel Thermochemistry of biologically important compounds. Heats of combustion of solid organic acids. J. Chem. Eng. Data 1964, 9 (4), 595–99. DOI: 10.1021/je60023a038. DeWit, H. G. M.; Offringa, J. C. A.; De Kruif, C. G.; Van Miltenburg, J. C. Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen and sulfur. III. Molar heat capacities measured by differential scanning calorimetry. Thermochim. Acta 1983, 65 (1), 43–51. DOI: 10.1016/0040-6031(83)80006-9.
  7. ↑ Index no. 607-096-00-9 of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006. OJEU L353, 31.12.2008, pp 1–1355 at p 542.

External links

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