Strategies for Selective Synthesis of Biomass-Based 1,13-Tridecanediol from Furfural

A novel strategy for preparing 1,13-tridecanediol by valorization of furfural was proposed, involving aldol condensation to build C-13 intermediates and further hydrodeoxygenation. During this process, Raney Ni exhibited excellent catalytic performance for the initial hydrogenation (C & boxH;C and C & boxH;O) with a yield of 98.30%, while Pd/TiO2-ZrO2 showed promising de-OH and ring opening performance. Results showed that ZrO2 was necessary for de-OH and ring opening, and the catalytic performance could be improved by incorporating with TiO2 to form TiO2-ZrO2 due to the increase in weak acid sites. Also, the introduction of Pd could further promote the reaction oriented toward obtaining 1,13-tridecanediol. After optimization, 1,13-tridecanediol yield could be straightforwardly up to 57.93% in water, and it would improve to 76.51% (69.64% based on furfural) by introducing trace amounts of methanol, and even the reaction parameters (time, pressure, temperature, etc.) contributed to the distribution of products. Additionally, mechanistic investigation revealed that there were multiple simultaneous or sequential reaction steps in the hydrodeoxygenation reaction, and the superior catalytic performance of Pd/TiO2-ZrO2 for oriented upgrading of furfural into 1,13-tridecanediol could be attributed to the synergistic effect of TiO2-ZrO2 and Pd. Overall, this work may provide some insights for the utilization of biomass resources in the future.

Automated summary

A novel strategy for preparing 1,13-tridecanediol by using furfural was proposed. The catalytic performance of Raney Ni and Pd/TiO2-ZrO2 was investigated, and the synergistic effect of TiO2-ZrO2 and Pd was found to play a crucial role in improving the yield.