CHEMO-ENZYMATIC SYNTHESIS AND FREE RADICAL POLYMERIZATION OF RENEWABLE ACRYLATE MONOMERS FROM CELLULOSE-BASED LACTONES

Florian Diot-Néant (1, 2) , Enita Rastoder (2) , Stephen A Miller (2) , Florent Allais (1)

1 ABI - Agro-Biotechnologies Industrielles
2 UF - University of Florida [Gainesville]

A chemo-enzymatic pathway involving a Candida antarctica type B lipase was developed to produce (S)-γ-hydroxymethyl-α,β-butenolide methacrylate (HBO-m) and (S)-γ-hydroxymethyl-γ-butyrolactone methacrylate (2H-HBO-m) from (S)-γ-hydroxymethyl-γ-butyrolactone (HBO), a biobased molecule obtained from cellulose-derived levoglucosenone. The acrylated monomer was then copolymerized through a free radical process with methacrylamide and methylene-γ-valerolactone, a green intermediate. Finally, methylene-tetrahydropyranyl (S)-γ-hydroxymethyl-γ-butyrolactone (M-THP-2H-HBO), synthesized via α-methylenation of 2H-HBO, was copolymerized with methyl methacrylate to access copolyacrylates exhibiting high glass transition temperatures.

Mots clés: Levoglucosenone; HBO; Lipase biocatalysis; Functionalized (meth)acrylates; α-Methylenation; Biobased polymers; Polyacrylates

Domaines: Polymères

Florian Diot-Néant, Enita Rastoder, Stephen A Miller, Florent Allais. CHEMO-ENZYMATIC SYNTHESIS AND FREE RADICAL POLYMERIZATION OF RENEWABLE ACRYLATE MONOMERS FROM CELLULOSE-BASED LACTONES. ACS Sustainable Chemistry & Engineering, 2018, 6 (12), pp.17284-17293. ⟨10.1021/acssuschemeng.8b04707⟩. ⟨hal-02777141⟩