Synthesis and Enzymatic Degradation of Sustainable Levoglucosenone-Derived Copolyesters with Renewable Citronellol Side Chains

Sami Fadlallah (1) , Quentin Carboué (1) , Louis M M Mouterde (1) , Aihemaiti Kayishaer (1) , Yasmine Werghi (1) , Aurélien a M Peru (1) , Michel Lopez (1) , Florent Allais (1)

1 ABI - Agro-Biotechnologies Industrielles

Recently, a renewable five-membered lactone containing citronellol (HBO-citro) was synthesized from levoglucosenone (LGO). A one-pot two-step pathway was then developed to produce a mixture of 5- and 6-membered Lactol-citro molecules (5ML and 6ML, respectively) from HBO-citro. Proton nuclear magnetic resonance (1H NMR) of a mixture of 5ML and 6ML at varying temperatures showed that the chemical shifts of the hydroxyls, as well as the 5ML:6ML ratio, are temperature-dependent. Indeed, a high temperature, such as 65 ◦C, led to an up-field shielding of the hydroxyl protons as well as a drop in the 5ML:6ML ratio. The monomers 5ML and 6ML were then engaged in polycondensation reactions involving diacyl chlorides. Renewable copolyesters with low glass transition temperatures (as low as −67 ◦C) and cross-linked citronellol chains were prepared. The polymers were then hydrolyzed using a commercial lipase from Thermomyces lanuginosus (Lipopan®50 BG). A higher degradation rate was found for the polymers prepared using Lactol-citro molecules, compared to those obtained by the polycondensation reactions of diacyl chlorides with Triol-citro—a monomer recently obtained by the selective reduction of HBO-citro

Mots clés: levoglucosenone; oxa-Michael addition; cross-linkable polymers; renewable polyesters; biodegradation

Domaines: Chimie; Polymères; Chimie organique

Sami Fadlallah, Quentin Carboué, Louis M M Mouterde, Aihemaiti Kayishaer, Yasmine Werghi, et al.. Synthesis and Enzymatic Degradation of Sustainable Levoglucosenone-Derived Copolyesters with Renewable Citronellol Side Chains. Polymers, 2022, 14 (10), pp.2082. ⟨10.3390/polym14102082⟩. ⟨hal-03722695⟩