Mixed Oxides as Catalysts for the Condensation of Cyclohexanol and Benzaldehyde to Obtain a Claisen–Schmidt Condensation Product

Abstract

Acid–base M2+MgAlO and M2+AlO mixed oxides (where M2+ = Mg, Cu, Co, Zn, and Ni) were obtained by thermal decomposition of the corresponding layered double hydroxide (LDH) precursors and used as catalysts for cyclohexanol and benzaldehyde condensation under solvent-free conditions. The catalysts were characterized by X-ray diffraction (XRD), X-ray fluorescence (XRF), scanning electron microscopy (SEM), and temperature-programmed desorption of CO2 (TPD-CO2). Gas chromatography–mass spectroscopy (GC/MS) was used for the identification and quantification of the product mixtures. In the reaction of cyclohexanol and benzaldehyde on M2+MgAlO and MgAlO catalysts, a 2,6-dibenzylidene-cyclohexanone was obtained as the main product as a result of consecutive one-pot dehydrogenation of cyclohexanol to cyclohexanone and subsequent Claisen–Schmidt condensation. In the reaction mixture obtained in the presence of NiAlO, CoAlO, and ZnAlO catalysts, a cyclohexyl ester of 6-hydroxyhexanoic acid was detected together with the main product. This is most likely a by-product obtained after the oxidation, ring opening, and subsequent esterification of the cyclohexanol.