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Oxidation of Citronellal to Citronellic Acid by Molecular Oxygen Using Supported Gold Catalysts

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Abstract

The oxidation of citronellal to citronellic acid was studied using molecular oxygen as oxidant and gold-containing supported catalysts under aqueous conditions. The reactions were carried out at 60–90 °C, with 200 Nml min−1O2 and at pH values from 9 to 12. The alumina- or titania-supported catalysts were synthesized according to the deposition–precipitation procedure using urea or NaOH. Mechanistic studies have revealed that radical-initiated reactions lead to undesired by-products especially at pH<9, that is, the C[DOUBLE BOND]C bond is attacked and a diol is primarily formed probably via an epoxide intermediate. This side reaction can be suppressed to a large extent by increasing the pH to 12 and by raising the catalyst/oxygen ratio. Furthermore, detailed studies on the influence of reaction time, pH value, reactant concentration and amount of catalyst show that citronellic acid can be obtained in over 90 % yield with total conversion of citronellal at pH 12 and a temperature of 80 °C.

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