Maleic Anhydride
Title: Maleic Anhydride
CAS Registry Number: 108-31-6
CAS Name: 2,5-Furandione
Additional Names: cis-butenedioic anhydride; toxilic anhydride
Molecular Formula: C4H2O3
Molecular Weight: 98.06
Percent Composition: C 48.99%, H 2.06%, O 48.95%
Literature References: May be prepd by sublimation of maleic acid and P2O5 under reduced pressure: Kempf, J. Prakt. Chem. [2] 78, 239 (1908). Commercial production by catalytic vapor-phase oxidation of benzene or other suitable hydrocarbons: Weiss, Downs, Ind. Eng. Chem. 12, 228 (1920); US 1318633 (1920 to Barrett Co.). Many other syntheses. Review of commercial methods of manufacture: Ashcroft, Clifford, Chem. Prod. 24, 11 (1961), C.A. 55, 9724d (1961); Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 514-518. Review: W. D. Robinson, R. A. Mount in Kirk-Othmer Encyclopedia of Chemical Technology vol. 14 (Wiley-Interscience, New York, 3rd ed., 1981) pp 770-793. Book: B. C. Trivedi, B. M. Culbertson, Maleic Anhydride (Plenum, New York, 1982) 872 pp.
Properties: Orthorhombic needles from chloroform; also readily by sublimation. Commercial grades are furnished in fused form, as briquettes. d 1.48. mp 52.8°. bp760 202.0°; bp400 179.5°; bp200 155.9°; bp100 135.8°; bp60 122.0°; bp40 111.8°; bp20 95.0°; bp10 78.7°; bp5 63.4°. Specific heat: 0.285 (solid); 0.396 (liq). Sol in water, forming maleic acid. Soly at 25° (g/100 g): acetone 227; ethyl acetate 112; chloroform 52.5; benzene 50; toluene 23.4; o-xylene 19.4; carbon tetrachloride 0.60; ligroin 0.25. Sol in dioxane. Sol in alc with ester formation.
Melting point: mp 52.8°
Boiling point: bp760 202.0°; bp400 179.5°; bp200 155.9°; bp100 135.8°; bp60 122.0°; bp40 111.8°; bp20 95.0°; bp10 78.7°; bp5 63.4°
Density: d 1.48
CAUTION: Potential symptoms of overexposure are conjunctivitis; photophobia, double vision; nasal and upper respiratory irritation; bronchial asthma; dermatitis. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 188.
Use: In Diels-Alder syntheses (as a dienophile), manuf alkyd-type of resins, dye intermediates, pharmaceuticals, agricultural chemicals (maleic hydrazide, malathion), in copolymerization reactions.

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