Selective hydrodeoxygenation of biomass-derived furfural-acetone to prepare 1-octyl acetate?

Green Chemistry Pub Date: 2019-07-22 DOI: 10.1039/C9GC01767D

Abstract

A green and efficient catalytic system for the one-pot production of 1-octyl acetate from biomass-derived furfural-acetone (FFA) under mild conditions was developed by selective hydrodeoxygenation over Pd/C and Sc(OTf)3 as a cocatalytic system in acetic acid. The effects of reaction conditions on product distribution have been systematically investigated. The highest 1-octyl acetate yield of 90% can be obtained under mild conditions (150 °C, 2 MPa H2, 2 h). Tetrahydrofuran ring opening and ester bond selective cleavage were found to be the key steps. In these steps, due to its suitable Lewis acidity, Sc(OTf)3 can not only promote ring-opening esterification but also selectively activate the secondary alcohol ester bond to achieve high selectivity for 1-octyl acetate. NMR and MS methods were utilized to investigate the reaction process. In addition, after 8 cycles of the Pd/C catalyst, the 1-octyl acetate yield gradually decreased from 90% to 80%. The decrease, according to XPS determination, in catalytic efficiency of the Pd/C catalyst was mainly due to the partial oxidation of metal Pd through air contact during post-treatment.

Graphical abstract: Selective hydrodeoxygenation of biomass-derived furfural-acetone to prepare 1-octyl acetate
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