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    ADIPIC ACID

    March 14, 2018, Categories  Chemistry/Nanotechnology

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    ADIPIC ACID

    ~ also known as Hexanedioic acid; 1,4-Butanedicarboxylic acid; 124-04-9; Adipinic acid; Adilactetten; etc. is the most important dicarboxylic acid. About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for nylon production.
    Chemical structure: C6H10O4 or HOOC(CH2)4COOH. Adipic acid is a dicarboxylic acid.
    Properties: Adipic acid is a white crystalline solid. It is insoluble in water.
    Production: 
    1. Adipic acid is produced from a mixture of cyclohexanol and cyclohexanone called “KA oil”, i.e. ketone-alcohol oil. The KA oil is oxidized with nitric acid to give adipic acid, via a multistep pathway. Early in the reaction, the cyclohexanol is converted to the ketone, releasing nitrous acid. Among its many reactions, the cyclohexanone is nitrosated. Side products of the method include glutaric and succinic acids. Nitrous oxide is produced as well, via the intermediacy of a nitrolic acid.
    Related processes start from cyclohexanol, obtained from phenol hydrogenation.
    1. Several methods have been developed by carbonylation of butadiene. E.g. hydrocarboxylation.
    2. Another method is oxidative cleavage of cyclohexene using hydrogen peroxide. The waste product is water.
    3. Historically, adipic acid was prepared by oxidation of various fats, thus the name (from Latin adeps, adipis – “animal fat”; cf. adipose tissue).
    Chemical reactions and Uses: Adipic acid is a dibasic acid (it has two acidic groups). The pKa values for their successive deprotonations are 4.41 and 5.41.
    Adipic acid is suited for intramolecular condensation reactions. Upon treatment with barium hydroxide at elevated temperatures, it undergoes ketonization to give cyclopentanone. About 60% of the 2.5 billion kg of adipic acid produced annually is used as a monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming nylon 66. Another major application is that it is a monomer for the production of polyurethane and its esters are plasticizers, especially in PVC. In medicine, Adipic acid has been incorporated into controlled-release formulation matrix tablets to obtain a pH-independent release for both weakly basic and weakly acidic drugs. It has also been incorporated into the polymeric coating of hydrophilic monolithic systems to modulate the intragel pH, resulting in zero-order release of a hydrophilic drug. In foods, adipic acid is used as a food ingredient, flavorant, and gelling aid. It is used in some calcium carbonate antacids to make them tart.
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