Biorizon scientists publish in ChemSusChem on Hydrazine-mediated Diels-Alder Aromatization of Biobased Furfurals

We are proud that Biorizon’s senior scientists Marc Crockatt and Jan Kees van der Waal recently published their work in the leading journal ChemSusChem. The article by Biorizon co-initiator TNO and Dr. Razvan Cioc and Prof. Dr. Pieter Bruijnincx of Utrecht University is entitled “Targeting Valuable Chemical Commodities: Hydrazine-mediated Diels-Alder Aromatization of Biobased Furfurals”. It addresses an alternative, redox-neutral method in which bio-derived furfural is activated as hydrazones prior to DA cycloaddition.

The hydrazine-mediated approach towards renewable aromatics production via Diels-Alder aromatization of readily available, biobased furfurals was explored as alternative to the more classical approaches that rely on reactive but also expensive reduced dienes (e. g., 2,5-dimethylfuran). To enable cycloaddition chemistry with these otherwise unreactive formyl furans, activation of the substrate by N,N-dimethyl hydrazone formation was investigated. The choice of the dienophile was key to the success of the transformation, and in this respect acrylic acid showed the most promising results in the synthesis of aromatics. This strategy allowed for combined selectivity up to 60 % for a complex transformation consisting of Diels-Alder cycloaddition, oxo-bridge opening, decarboxylation, and dehydration. Exploration of the furfural scope yielded generic structure-reactivity-stability relationships. The proposed methodology enabled the redox-efficient, operationally simple, and mild synthesis of renewable (p-disubstituted) aromatics of commercial importance under remarkably mild conditions.

The improved atom utilization, operational simplicity, and energy efficiency recommend this approach as alternative to the classical “redox-detour” synthesis of terephthalic acid from 2,5-dimethylfuran.

Please read the entire publication in the leading scientific journal ChemSusChem (impact factor 9.140).


If you want to know more about this research, please contact senior scientist Marc Crockatt at or +31 (0)6 46 84 74 02.

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