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Iron(III) Arylhydrazone Complexes Immobilized on Amine‐Functionalized Mesoporous Silica: Catalysts for the Valorization of Biomass‐Derived Furfuryl Alcohol

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Highly efficient conversion of biomass-derived furfuryl alcohol into value-added products by iron(III) arylhydrazone complexes immobilized on amine-functionalized mesoporous silica is reported in this work. A highly favorable effect of microwave irradiation resulted in complete conversion after 0.25 h in the absence of any solvent, with a strong furfuryl alcohol polymerization and furfural as a by-product.


Abstract

The aquasoluble FeIII complexes [Fe(H2O)3(L1)] ⋅ 4H2O (Fe1) and [Fe(H2O)3(L2)] ⋅ 3H2O (Fe2), bearing the basic forms of 5-chloro-3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-2-hydroxy-benzenesulfonic acid (H3L1) and 3-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)-2-hydroxy-5-nitrobenzenesulfonic acid (H3L2), were incorporated for the first time into amine-functionalized SBA-15 support via an impregnation method. The successful preparation of the composites was confirmed by Fourier-Transform Infrared spectroscopy (FT-IR), powder X-ray diffraction (XRD), scanning electron microscope (SEM/EDS), transmission electron microscopy (TEM), elemental analysis, and nitrogen adsorption-desorption isotherms. The resulting Fe1@aptesSBA-15 and Fe2@aptesSBA-15 composites were tested as the first SBA-15-based heterogeneous catalysts for the conversion of furfuryl alcohol under mild reaction conditions (80 to 100 °C) and with an environmentally friendly oxidant (TBHP, 70 % aq. sol. with 1 : 1 oxidant/substrate molar ratio). The influence of various factors, such as reaction time, amounts of oxidant and catalyst, was investigated. The reaction time can be fairly reduced by adopting a microwave-assisted method allowing it to reach complete conversion after 0.25 h, in the absence of any added solvent or additive. Under these conditions, a vigorous furfuryl alcohol polymerization process occurred, with furfural as a by-product. Recycling studies were carried out for Fe2@aptesSBA-15 and after four consecutive runs, the overall conversion of furfuryl alcohol remained high (≥99 %), without an appreciable change in the obtained yield.

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