Chemo-enzymatic preparation of new bio-based bis-and trisphenols: new versatile building blocks for polymer chemistry

Immobilized Candida antartica lipase B (aka CAL-B) was used to perform solvent-free and in solvent transesterifications of a derivative from ferulic acid (1), ethyl dihydroferulate (2), with various bio-based polyols (isosorbide, 1,3-propanediol, 1,4-butanediol and glycerol). The use of 1.5 molar eq...

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Bibliographic Details
Published in:RSC Advances
Main Authors: Pion, Florian, F., Reano, Armando, Félix, A. F., Ducrot, Paul Henri, P. H., Allais, Florent, F.
Other Authors: Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Region Ile-de-France
Format: Article in Journal/Newspaper
Language:English
Published: HAL CCSD 2013
Subjects:
LIPASE-CATALYZED SYNTHESIS
ORGANIC-SOLVENT MEDIA
PHENOLIC-ACIDS
FERULIC ACID
ANTIOXIDANT ACTIVITY
RENEWABLE RESOURCES
ENZYMATIC-SYNTHESIS
CANDIDA-ANTARCTICA
ESTERIFICATION
TRANSESTERIFICATION
[SDV.SA]Life Sciences [q-bio]/Agricultural sciences
Antarc*
Antarctica
antartic*
Online Access:https://hal.science/hal-01004482
https://doi.org/10.1039/c3ra41247d
Description
Summary:Immobilized Candida antartica lipase B (aka CAL-B) was used to perform solvent-free and in solvent transesterifications of a derivative from ferulic acid (1), ethyl dihydroferulate (2), with various bio-based polyols (isosorbide, 1,3-propanediol, 1,4-butanediol and glycerol). The use of 1.5 molar eq of ethyl dihydroferulate (2) per alcohol functionality and CAL-B (10% by weight relative to the total weight of polyol and 2) led to the corresponding poly-ferulates (3-6) in very good yields and high purity. These polyferulates were then efficiently transformed through one-step processes into the corresponding acrylates (7-10) and allyl ethers (11-14) to demonstrate their potential use as biorenewable macromonomers in a wide range of polymerization systems.

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