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Maleic anhydride is a classic substrate for Diels-Alder reactions. [9] It was used for work in 1928, on the reaction between maleic anhydride and 1,3-butadiene, for which Otto Paul Hermann Diels and Kurt Alder were awarded the Nobel Prize in 1950. It is through this reaction that maleic anhydride is converted to many pesticides and pharmaceuticals.
Styrene maleic anhydride (SMA or SMAnh) is a synthetic polymer that is built-up of styrene and maleic anhydride monomers. In one copolymer , the monomers can be almost perfectly alternating. [ 1 ] but (random) copolymerisation with less than 50% maleic anhydride content is also possible. [ 2 ]
Maleic acid has a heat of combustion of -1,355 kJ/mol., [6] 22.7 kJ/mol higher than that of fumaric acid. Maleic acid is more soluble in water than fumaric acid. The melting point of maleic acid (135 °C) is also much lower than that of fumaric acid (287 °C). As confirmed by X-ray crystallography, maleic acid is planar.
In another process, maleic anhydride is first opened with water or another alcohol to form maleic acid and is then reacted with DCPD where an alcohol from the maleic acid reacts across one of the double bonds of the DCPD. This product is then used to end-cap the UPR resin which yields a product with unsaturation on the end-groups.
3-Sulfolene reacts with maleic anhydride in boiling xylene to cis-4-cyclohexene-1,2-dicarboxylic anhydride, obtaining yields of up to 90%. [4] 3-Sulfolene reacts also with dienophiles in trans configuration (such as diethyl fumarate) at 110 °C with SO 2 elimination in 66–73% yield to the trans-4-cyclohexene-1,2-dicarboxylic diethyl ester. [17]
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Maleimide is a chemical compound with the formula H 2 C 2 (CO) 2 NH (see diagram). This unsaturated imide is an important building block in organic synthesis.The name is a contraction of maleic acid and imide, the -C(O)NHC(O)- functional group.