An undergraduate organic chemistry experiment has been developed that introduces students to structures and fundamental concepts of polymer chemistry, modern advances in sustainable materials, and utilization of greener synthesis methods and materials. The biodegradable and bio-sourced polymer, poly-L-lactic acid (PLLA), and nylon 66 are synthesized, characterized, and compared in this three-part experiment. The PLLA is synthesized by forming an L-lactide intermediate followed by ring-opening polymerization (ROP). The L-lactide intermediate synthesis utilizes a reflux reaction involving L-lactic acid, a zeolite catalyst, isobutyl acetate solvent, and a Dean-Stark trap. Characterization of the L-lactide includes specific rotation, 1H NMR, and IR. The PLLA polymer is formed from the L-lactide via a microwave synthesis and characterized by IR, 1H NMR, 13C NMR, and end-group analysis. Nylon 66 is synthesized from adipoyl chloride and hexamethylenediamine solutions and characterized by IR. DSC and TGA are used to observe and compare the degradation of the synthesized PLLA and nylon 66.

Green poly(L-lactic acid) polymer synthesis developed for use in an organic chemistry experiment

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