Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers

Antioxidant norbornene-based monomers bearing biobased sterically hindered phenols (SHP)-NDF (norbornene dihydroferulate) and NDS (norbornene dihydrosinapate)-have been successfully prepared through biocatalysis from naturally occurring ferulic and sinapic acids, respectively, in presence of Candida...

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Bibliographic Details
Published in:Frontiers in Chemistry
Main Authors: Diot-Néant, Florian, Migeot, Loïs, Hollande, Louis, Reano, Felix A., Domenek, Sandra, Allais, Florent
Other Authors: Agro-Biotechnologies Industrielles (ABI), AgroParisTech, University of Florida Gainesville (UF), Ingénierie, Procédés, Aliments (GENIAL), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Université Paris-Saclay, Génie et Microbiologie des Procédés Alimentaires (GMPA), Région Grand Est, Conseil Départemental de la Marne, Grand Reims
Format: Article in Journal/Newspaper
Language:English
Published: HAL CCSD 2017
Subjects:
sinapic acid
DPPH
antioxidants
ROMP
lipase
CAL-B
norbornene
ferulic acid
[CHIM.POLY]Chemical Sciences/Polymers
Antarc*
Antarctica
Online Access:https://hal.science/hal-01727154
https://hal.science/hal-01727154/document
https://hal.science/hal-01727154/file/2017_Diot-N%C3%A9ant_Frontiers%20in%20Chemistry.pdf
https://doi.org/10.3389/fchem.2017.00126
Description
Summary:Antioxidant norbornene-based monomers bearing biobased sterically hindered phenols (SHP)-NDF (norbornene dihydroferulate) and NDS (norbornene dihydrosinapate)-have been successfully prepared through biocatalysis from naturally occurring ferulic and sinapic acids, respectively, in presence of Candida antarctica Lipase B (Cal-B). The ring opening metathesis polymerization (ROMP) of these monomers was investigated according to ruthenium catalyst type (GI) vs. (HGII) and monomer to catalyst molar ratio ([M]/[C]). The co-polymerization of antioxidant functionalized monomer (NDF or NDS) and non-active norbornene (N) has also been performed in order to adjust the number of SHP groups present per weight unit and tune the antioxidant activity of the copolymers. The polydispersity of the resulting copolymers was readily improved by a simple acetone wash to provide antioxidant polymers with well-defined structures. After hydrogenation with p-toluenesulfonylhydrazine (p-TSH), the radical scavenging ability of the resulting saturated polymers was evaluated using α,α-diphenyl-β-picrylhydrazyl (DPPH) analysis. Results demonstrated that polymers bearing sinapic acid SHP exhibited higher antiradical activity than the polymer bearing ferulic acid SHP. In addition it was also shown that only a small SHP content was needed in the copolymers to exhibit a potent antioxidant activity.

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