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Issue 20, 2020
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Modulating trans-imination and hydrogenation towards the highly selective production of primary diamines from dialdehydes

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Abstract

Bio-based primary diamines are important building blocks for sustainable bio-polymers, but their synthesis remains challenging due to the high susceptibility to polymerization. Herein, we have developed a new strategy to suppress the polymerization by employing a more nucleophilic alkylamine to scavenge the dialdehyde and a Co/ZrO2 catalyst to regulate the trans-imination and hydrogenation activity. With this strategy, 2,5-bis(aminomethyl)furan (BAMF), a promising monomer for the production of new polyamides and polyureas, is successfully synthesized via the reductive amination of biomass-derived 2,5-diformylfuran (DFF) under a H2 and NH3 atmosphere with an unprecedentedly high selectivity up to 95%. This strategy is applicable to the reductive amination of other biomass-derived dialdehydes, thus paving a new way to bio-based diamine monomers.

Graphical abstract: Modulating trans-imination and hydrogenation towards the highly selective production of primary diamines from dialdehydes

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Article information


Submitted
05 Jul 2020
Accepted
04 Sep 2020
First published
04 Sep 2020

Green Chem., 2020,22, 6897-6901
Article type
Paper

Modulating trans-imination and hydrogenation towards the highly selective production of primary diamines from dialdehydes

H. Qi, F. Liu, L. Zhang, L. Li, Y. Su, J. Yang, R. Hao, A. Wang and T. Zhang, Green Chem., 2020, 22, 6897
DOI: 10.1039/D0GC02280B

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