Issue 21, 2025

Upgrading biomass-derived glycerol into terminal olefins via molybdenum-catalyzed carbon-chain extension

Abstract

The upgrading of glycerol predominantly focuses on synthesizing low-carbon molecules containing three or fewer carbon atoms through chemical bond cleavage, while research on generating long-chain chemicals through carbon–carbon bond formation is relatively scarce. Herein, a novel molybdenum-catalyzed process for carbon chain extension of glycerol has been developed to produce 1,5-hexadiene, a terminal olefin. The molybdenum catalyst complexed with 8-hydroxyquinoline (Mo-8-HQ) achieved a 52% yield of 1,5-hexadiene when using triphenylphosphine as the reductant. Systematic experiments and theoretical calculations revealed that the reaction pathway comprised two MoVI–MoIV catalytic cycles, wherein glycerol initially underwent deoxydehydration to yield allyl alcohol as a crucial intermediate. Subsequently, the deoxygenation reaction proceeded to generate allyl radicals, which underwent C(sp3)–C(sp3) homo-coupling to form the diene product. This work significantly expands the realm of glycerol utilization and opens up novel avenues for the production of multifunctionalized chemicals with long carbon chains from renewable feedstocks.

Graphical abstract: Upgrading biomass-derived glycerol into terminal olefins via molybdenum-catalyzed carbon-chain extension

Supplementary files

Article information

Article type
Paper
Submitted
17 fev 2025
Accepted
24 apr 2025
First published
30 apr 2025

Green Chem., 2025,27, 6123-6132

Upgrading biomass-derived glycerol into terminal olefins via molybdenum-catalyzed carbon-chain extension

H. Yin, X. Kong, R. Lu, X. Zhang, W. Yu, H. Jiang, X. Zhu and F. Lu, Green Chem., 2025, 27, 6123 DOI: 10.1039/D5GC00843C

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