Issue 8, 2012

Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers

Abstract

The chemo-enzymatic epoxidation of allylated gallic and vanillic acids with lipase B from Candida antarctica and aqueous hydrogen peroxide in the presence of caprylic acid was investigated. The use of 1 molar eq of caprylic acid and 1.8–2 molar eq of H2O2 per allylic double bond led to a high degree of conversion to epoxides (89% yield for allylated gallic acid and 87% yield for allylated vanillic acid) comparatively to the hazardous peracid mCPBA (1.5–3.2 molar eq per double bond allowed 75–85% yield). The epoxidized products obtained could be used in the formulation of novel bio-based epoxy resins.

Graphical abstract: Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers

Supplementary files

Article information

Article type
Paper
Submitted
13 Apr 2012
Accepted
07 Jun 2012
First published
13 Jun 2012

Green Chem., 2012,14, 2328-2336

Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers

C. Aouf, J. Lecomte, P. Villeneuve, E. Dubreucq and H. Fulcrand, Green Chem., 2012, 14, 2328 DOI: 10.1039/C2GC35558B

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