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

Chahinaz Aouf (1) , Jerome Lecomte (2) , Pierre Villeneuve (2) , Eric Dubreucq (2) , Helene Fulcrand-Hoh (1)

1 SPO - Sciences Pour l'Oenologie
2 UMR IATE - Ingénierie des Agro-polymères et Technologies Émergentes

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.

Mots clés: ANTARCTICA LIPASE-B; BISPHENOL-A; PEROXYCARBOXYLIC ACIDS; ENGINEERING PLASTICS; CATALYZED SYNTHESIS; EPOXIDATION; OIL; EXPOSURE; LIGNIN; FEMALE

Domaines: Sciences du Vivant [q-bio]

Chahinaz Aouf, Jerome Lecomte, Pierre Villeneuve, Eric Dubreucq, Helene Fulcrand-Hoh. Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers. Green Chemistry, 2012, 14 (8), pp.2328 - 2336. ⟨10.1039/c2gc35558b⟩. ⟨hal-01506271⟩