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- Maleic acid or
(Z)-butenedioic acid or cis-butenedioic acid or malenic acid or maleinic
acid or toxilic acid is an organic compound that is a dicarboxylic acid.
- The molecule
consists of an ethylene group flanked by two carboxylic acid groups.
Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid
is the trans isomer.
- The cis isomer is
the less stable one of the two; the difference in heat of combustion is
- The physical
properties of maleic acid are very different from those of fumaric acid.
Maleic acid is soluble in water, whereas fumaric acid is not; and the
melting point of maleic acid (130 - 139 °C) is also much lower than that
of fumaric acid (287 °C).
- Both properties of
maleic acid can be explained on account of the intramolecular hydrogen
bonding that takes place at the expense of intermolecular interactions.
- Maleic acid should
not be confused with malic acid or malonic acid, both of which are
different types of dicarboxylic acids. In biology the compound goes by
the name ionised maleate.
- In industry,
maleic acid is derived from maleic anhydride by hydrolysis. Maleic
anhydride is produced from benzene or butane in an oxidation
process.Maleic acid is a reactant in many Diels-Alder reactions.
- The maleate ion is
the ionised form of maleic acid. It is of importance to biochemistry.
The maleate ion is useful in biochemistry as an inhibitor of
- Maleic acid esters
are also called maleates, for instance dimethyl maleate. Maleic acid is
an industrial raw material for the production of glyoxylic acid by
- Maleic acid is
converted into maleic anhydride by dehydration, to malic acid by
hydration, and to succinic acid by hydrogenation.
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