Maleic acid
Maleic Acid
Maleic acid is an organic compound that is a dicarboxylic acid, with the formula C_H_O_. It is the cis-isomer of butenedioic acid, whereas the trans-isomer is known as fumaric acid. Maleic acid is a colorless or white crystalline solid that is soluble in water and is used in various industrial applications.
Structure and Properties
Maleic acid is characterized by the presence of two carboxyl groups (-COOH) attached to a carbon-carbon double bond. The cis configuration of the carboxyl groups in maleic acid leads to its distinct chemical properties compared to its trans counterpart, fumaric acid.
The molecular structure of maleic acid allows for intramolecular hydrogen bonding, which affects its solubility and melting point. Maleic acid has a melting point of approximately 135 °C and is more soluble in water than fumaric acid.
Synthesis
Maleic acid can be synthesized through the catalytic oxidation of benzene or butane. It is also produced as a byproduct in the manufacture of phthalic anhydride.
Applications
Maleic acid is used in the production of polyesters, alkyd resins, and as a precursor to maleic anhydride. It is also employed in the food industry as an acidulant and in the pharmaceutical industry for the synthesis of various compounds.
Chemical Reactions
Maleic acid readily undergoes dehydration to form maleic anhydride. It can also participate in Diels-Alder reactions due to its electron-deficient double bond, making it a useful dienophile in organic synthesis.
Health and Safety
Maleic acid is considered to be an irritant and should be handled with care. It can cause skin and eye irritation upon contact and may be harmful if ingested or inhaled.
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Contributors: Prab R. Tumpati, MD
