The production of chemical building blocks and polymer precursors from biorenewable and sustainable resources is an attractive method to bypass traditional fossil fuel derived materials. Accordingly, we report the organocatalytic recycling of postconsumer polylactide (PLA) into value-added small molecules. This strategy, using the highly active transesterification catalyst triazabicyclodecene, is shown to completely depolymerize PLA in the presence of various alcohols into valuable lactate esters. Using previously used PLA packaging material, the depolymerization is complete in minutes at room temperature and fully retains the stereochemistry of the lactate species. Further, the modularity and utility of this methodology with respect to polyester substrate is detailed by using a variety of functional alcohols to depolymerize both PLA and polyglycolide, with the corresponding ester smallmolecules being used to make new polymeric materials. The opportunities to transform waste streams into value-added chemicals and new materials through simple and versatile chemistry hold significant potential to extend the lifecycle of renewable chemical feedstocks. KEYWORDS: biodegradable; depolymerization; glycolate ester; lactate ester; organic catalysis; polyesters; polyglycolide; polylactide; recycling; transesterification INTRODUCTION As society increasingly deals with inherently limited natural resources, the utilization of 7% of fossil fuels for the production of plastics is a significant drain on petrochemical feedstocks.1 With the demand for polymeric materials increasing, it is imperative to develop building blocks based on renewable and sustainable resources.2 The conversion of biomass to value-added small molecules and polymer precursors is an attractive method to bypass traditional fossil fuel-based chemical production.3-5 For example, polylactide (PLA) has emerged as one of the most promising biorenewable and biodegradable polymers due to its utility in packaging, textile, and biomedical applications. [6][7][8][9] The recent addition of Natureworks TM LLC facility in the US has put annual production capacity of PLA at over 150,000 tons, making it a high-volume commodity material. [10][11][12] This largescale production and the predicted annual growth rate of 19% for bioplastics 13 assures that many new PLA derived products will enter the marketplace in the coming decades.