Sustainable oxidative cleavage of catechols for the synthesis of muconic acid and muconolactones including lignin upgrading
| Autor: | Christophe Darcel, Frédéric Caijo, Florentin Coupé, Paul T. Anastas, Vincent Escande, Laurène Petitjean |
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| Přispěvatelé: | Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), DEMETA SAS, Yale University [New Haven], ANRT French National Research Agency (ANR), Rennes Metropole council, ANR labcom program French National Research Agency (ANR) [17-LCV2-0009-01], ANR-17-LCV2-0009,GREENCARE,Green CAtalysis REnnes(2017), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA) |
| Rok vydání: | 2020 |
| Předmět: |
Green chemistry
Catechol Muconic acid Performic acid 010405 organic chemistry Depolymerization 010402 general chemistry 01 natural sciences Pollution 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Cascade reaction [CHIM]Chemical Sciences Environmental Chemistry Lignin Organic chemistry |
| Zdroj: | Green Chemistry Green Chemistry, 2020, 22 (18), pp.6204-6211. ⟨10.1039/d0gc02157a⟩ Green Chemistry, Royal Society of Chemistry, 2020, 22 (18), pp.6204-6211. ⟨10.1039/d0gc02157a⟩ |
| ISSN: | 1463-9270 1463-9262 |
| DOI: | 10.1039/d0gc02157a |
| Popis: | International audience; Muconic acid and muconolactones are attracting high interest as platform molecules for the synthesis of a variety of compounds, especially in the domain of materials. Although several technologies have been described for their synthesis, there is still a lack of performance, especially regarding green chemistry principles. In this study, we describe the development of an optimized catechol oxidative cleavage to muconic acid using performic acid in an intriguingly safe fashion. Common iron salts were used as catalysts to a level as low as 0.005 mol%, for a maximum turnover number of 13 200. Maximum muconic acid yield reached 84% after isolation by simple filtration. This procedure optimized on catechol was also efficient over a wide range of substituted catechols, providing access to muconolactones in a domino reaction. Noticeably, biobased catechols produced by a proven technology of lignin depolymerization were cleaved into muconolactones of high functional value. Applying this supplementary cleavage step to catechols obtained by lignin depolymerization was thus an ultimate way to maximize the economical value created from lignin. In contrast to other studies, lignin was not only depolymerized, but also depolymerization products were further transformed to take as much value from biomass as possible. |
| Databáze: | OpenAIRE |
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