Reductive Amination/Cyclization of Methyl Levulinate with Aspartic Acid: Towards Renewable Polyesters with a Pendant Lactam Unit. Issue 14 (11th June 2019)

• Record Type: Journal Article
• Authors: Bernhard, Yann; Pellegrini, Sylvain; Bousquet, Till; Favrelle, Audrey; Pelinski, Lydie; Cazaux, Frédéric; Gaucher, Valérie; Gerbaux, Pascal; Zinck, Philippe
• Is Part Of: ChemSusChem. Volume 12:Issue 14(2019)
• Page Start: 3370
• Page End: 3376
• Publication Date: 2019-06-11
• Subjects: aspartic acid -- biobased polyesters -- levulinic acid -- polymers -- reductive amination; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201900745
• Languages: English
• ISSNs: 1864-5631

Abstract

Abstract: Environmental regulation and depletion of fossil resources are boosting the search for new polymeric materials produced from biomass. Here, the synthesis of a new diester bearing a pendant lactam unit from methyl levulinate and aspartic acid is reported. The palladium‐catalyzed reductive amination/cyclization sequence was carefully optimized to afford the diacid with high yield (>95 %). In a second step, the compound was esterified to give the corresponding diester. The latter monomer was copolymerized with α–ω linear diols, yielding polyesters with molecular weights up to 20.5 kg mol −1 . Abstract : Biobased polyesters : The renewable building blocks aspartic and levulinic acid are combined by a catalytic reductive amination/cyclization process to yield a new diester. The latter is copolymerized with biobased diols to obtain fully biobased polyesters with a pendant rigid lactam unit.