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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.
In industry, maleic acid is derived by hydrolysis of maleic anhydride, the latter being produced by oxidation of benzene or butane. [4] Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. [8] Maleic acid may be used to form acid addition salts with drugs to make them more stable, such as indacaterol ...
It can be described as the double ester of maleic acid with the alcohol 2-ethylhexanol. It is commonly called dioctyl maleate (DOM), reflecting the older usage of "octane" to refer to any 8-carbon alkane, straight-chained or branched. The compound is manufactured by treating 2-ethylhexanol with maleic anhydride and an
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 ]
Succinic anhydride hydrolyzes readily to give succinic acid: (CH 2 CO) 2 O + H 2 O → (CH 2 CO 2 H) 2. With alcohols (ROH), a similar reaction occurs, delivering the monoester: (CH 2 CO) 2 O + ROH → RO 2 CCH 2 CH 2 CO 2 H. Succinic anhydride is used in acylations under Friedel-Crafts conditions, as illustrated by the industrial route to the ...
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]
Maleimide-mediated methodologies are among the most used in bioconjugation. [5] [6] Due to fast reactions and high selectivity towards cysteine residues in proteins, a large variety of maleimide heterobifunctional reagents are used for the preparation of targeted therapeutics, assemblies for studying proteins in their biological context, protein-based microarrays, or proteins immobilisation. [7]
Dibutyl maleate can be prepared by the reaction of maleic acid anhydride and 1-butanol in presence of p-toluenesulfonic acid. [3] [4] Uses