A new family of bio-based linear polyesters from oleic acid was developed by a bulk polymerization process. First, efficient chemical pathways were selected to synthesize three monomer derivatives from 1,18-(Z)-octadec-9-enedioic acid, allowing the synthesis of four polyesters that differ by the number of double bonds along the polymer backbone. After the analysis of the structure of the polymers, their thermal properties and their biodegradability were investigated. It was shown that the melting temperature of the polyesters increased with the decrease in the unsaturation content in the repeat units of the polymers and they have very low glass-transition temperatures. A biodegradation process was also highlighted for poly­(1,18-(Z)-octadec-9-enylene 1,18-(Z)-octadec-9-enedioate) and poly­(1,18-octadecylene 1,18-octadecanedioate). Based on their thermal features, these biodegradable polyesters can represent an alternative of the synthetic polymers derived from petroleum hydrocarbons, such as low-density polyethylene.

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7This work compares the biodegradability of polyesters produced by an esterification reaction

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N-Arachidonoyl glycine was synthesized in a chemo-enzymatic process where glycine tert -butyl ester was acylated by arachidonic acid and the resulted ester was then de-protected to give the final product. Among various lipases tested and chosen for their ability to cleave fatty amides, that from Candida antarctica B gave the best results resulting in a 39% hydrolysis after 24 h. This enzyme was then used for the reverse N-acylation synthesis and gave a 75% product formation after 24 h using methyl ester of arachadonic acid as acyl donor and acetonitrile as solvent. Direct acylation of glycine gave less than 10% yield.

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