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Maleic anhydride is used in the preparation of unsaturated polyester resins, 4-butanediol, fumairc acid, tetrahydrofuran and gamma-butyrolactone. It is also used as lubricating oil additives, dispersants, artificial sweeteners, flavor enhancements, floor polishes and corrosion inhibitors. It finds application in personal care products like hair sprays. Further, it is used in water treatment chemicals, detergents, pharmaceuticals and copolymers. It is an active substrate for Diels-Alder reactions and dimerizes to form cyclobutane tetracarboxylic dianhydride .
Reactive dienophile. For a review of its Diels-Alder reactions, see: Org. React., 4, 1 (1948). For examples, see: Org. Synth. Coll., 3, 807 (1955); 4, 890 (1963). For reaction with Danishefsky's diene ( 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, L14672 ), see: Org. Synth. Coll., 7, 312 (1990).
Also undergoes photochemical and thermal (2+2)-cycloadditions with alkenes. For reaction with 1-alkynes, see: Chem. Ber., 102, 3974 (1969).
For thermal (2+2)-cycloaddition with allene at high temperature, see: Org. Synth. Coll., 5, 459 (1973).
For use in combination with Urea hydrogen peroxide adduct, L13940 , to generate peroxymaleic acid in epoxidation and Baeyer-Villiger reactions, see: Heterocycles, 36, 1075 (1993). Peroxymaleic acid can also be generated in situ from maleic anhydride and 30% H2O2 in NMP, and has been found to be a very effective oxidant for conversion of sulfides to sulfoxides. For a study of stoichiometric and catalytic oxidations with this system, see: J. Org. Chem., 61, 5693 (1996).
Bao, Z.; Lee, E.; Tao, J.; Sun, X. Effect of halloysite and maleic anhydride grafted polypropylene on the isothermal crystallization kinetics of polypropylene based composites. Polym. Sci. Ser. A Polym. Phys. 2015, 57 (6), 889-897.
Chatzidimitriou, A.; Bond, J. Q. Oxidation of levulinic acid for the production of maleic anhydride: breathing new life into biochemicals. Green Chem. 2015, 17 (8), 4367-4376.
Gefahrenhinweise (EU): H302-H314-H334-H317
Harmful if swallowed. Causes severe skin burns and eye damage. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause an allergic skin reaction.
Wear respiratory protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.