Electrochemically Triggered Chain Reactions for the Conversion of Furan Derivatives

Chen, Rong; Yang, Cangjie; Zhou, Zefeng; Haeffner, Fredrik; Dersjant, Alinda; Dulock, Nicholas; Dong, Qi; He, Da; Jin, Jing; Zhao, Yanyan; Niu, Jia; Wang, Dunwei

doi:10.1002/ange.202016601

Electrochemically Triggered Chain Reactions for the Conversion of Furan Derivatives

Journal Article · Tue Feb 23 23:00:00 EST 2021 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.202016601· OSTI ID:1780267

^[1]; Yang, Cangjie ^[1]; Zhou, Zefeng ^[1]; Haeffner, Fredrik ^[1]; Dersjant, Alinda ^[1]; Dulock, Nicholas ^[1]; Dong, Qi ^[1]; He, Da ^[1]; Jin, Jing ^[1]; Zhao, Yanyan ^[1]; ^[1]; ^[1]

Department of Chemistry Boston College Merkert Chemistry Center 2609 Beacon St. Chestnut Hill MA 02467 USA

Abstract

We report an electrochemical method for coupling biomass‐derived C5/C6 compounds to value‐added fuel precursors. Using only 2 % of equivalent charges, 2‐methylfuran (2‐MF) was oxidized to yield a cation radical, which readily reacted with 3‐hexene‐2,5‐dione, a derivate of 2,5‐dimethylfuran, to produce 3‐(5‐methylfuran‐2‐yl)hexane‐2,5‐dione. The product was converted to 4‐ethylnonane (a component of biodiesel/jet fuel) in a single step in excellent yield. Importantly, the reaction was not sensitive to oxygen, and a trace amount of water was found to promote the reaction. Detailed mechanistic studies confirmed the proposed reaction pathways. Key to the mechanism is the radical generation that is enabled by electrochemistry. The radical is regenerated at the end of a reaction cycle to ensure chain propagation for an average of ca. 47 times, resulting in an apparent Faradaic efficiency of 4700 %.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: EE0008086

OSTI ID:: 1780267

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 14 Vol. 133; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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