Oxidation of cyclic ketones to dicarboxylic acids

Abstract

This paper reports the results of studies concerning an alternative method of obtaining dicarboxylic acids, which consist of the oxidation of cyclic ketones with oxygen or air. The raw materials used were cyclopentanone, cycloheptanone, cyclooctanone, cyclododecanone, 1-tetralon, 2-methylhexanone, 3-methylcyclohexanone and 4-methylcyclohexanone. Oxidation reactions were conducted at 70-100°C, under pressure of 0.1 or 0.4 MPa, for 6 h, utilizing the salts of transition metals as catalyst and acetic acid as solvent. For example, when cyclopentanone was oxidized in the presence of Mn(II) salt, a conversion above 98% and selectivity to glutaric acid up to 68% were obtained. Among synthesized dicarboxylic acids, 1,12-dodecanoic acid was obtained with the highest selectivity of 76%.

Keywords

• dicarboxylic acids
• cyclic ketones
• oxidation
• cyclopentanone
• glutaric acid