Depolymerisation of condensed tannins in ethanol as a gateway to biosourced phenolic synthons
2013
Roumeas, Laurent | Aouf, Chahinaz | Dubreucq, Eric | Fulcrand-Hoh, Helene | Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE) ; Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université Montpellier 2 - Sciences et Techniques (UM2)-Centre international d'études supérieures en sciences agronomiques (Montpellier SupAgro)-Université de Montpellier (UM)-Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro) | Sciences Pour l'Oenologie (SPO) ; Université Montpellier 1 (UM1)-Institut National de la Recherche Agronomique (INRA)-Université de Montpellier (UM)-Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro) | Region Languedoc-Roussillon
Plant polyphenols are potential sources of substitutes for phenolic petrochemicals, such as bisphenol A. Among them, condensed tannins are the most abundant after lignins in terrestrial plants. They are especially encountered in agro-industrial residues (i.e. fruit marc) and unprocessed biomass (i.e. barks, needles, and leaves). However, this class of biopolymers requires a depolymerisation step prior to their industrial use as fine chemicals. In this work, phenolic synthons were produced by depolymerisation of an industrial grape seed extract of condensed tannins at the multigram scale. The optimization of the depolymerisation reaction through the selection of the most suitable solvent, nucleophilic agent and temperature allowed the reaction to be carried out at mild temperature (40 degrees C), in two hours, using ethanol as a solvent. The isolation of compounds of interest was performed by precipitation in ethyl acetate followed by a simple adsorption/desorption step on a polyamide cartridge using ethanol as an eluent.
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