News
17-11-2022
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).
Contact
If you want to know more about this research, please contact senior scientist Marc Crockatt at marc.crockatt@tno.nl or +31 (0)6 46 84 74 02.
See also:
Biorizon scientists publish in Angewandte Chemie IE
We are proud that, once again, Biorizon’s senior scientists Marc Crockatt and Jan Kees van der Waal contributed to work recently published in the leading journal Angewandte Chemie IE. The article by Biorizon co-initiator TNO and Dr. Razvan Cioc and Prof. Dr. Pieter Bruijnincx of Utrecht University is entitled “The Interplay between Kinetics and Thermodynamics in Furan Diels-Alder Chemistry for Sustainable Chemicals Production.” It assesses the state of play in this rapidly evolving field.
Biorizon scientists publish novel, efficient routes toward bio-aromatics in Angewandte Chemie & Green Chemistry
We are proud that research by Biorizon’s lead scientist Marc Crockatt was recently published in the leading journals Angewandte Chemie and, together with Biorizon’s senior scientist Dr. Jan Kees van der Waal, Green Chemistry. Biorizon co-initiator TNO and Utrecht University have developed a more efficient way to convert biomass into industrially important bio-aromatics. Furthermore, they have demonstrated, for the first time, that furfural can be directly converted to bio-aromatics.
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