Transforming polylactide into value‐added materials
Abstract
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 small‐molecules 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. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012
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The functional group tolerance of TBD allows the introduction of different polymerizable groups (e.g. olefin) to the ester products, which provides a number of opportunities in the production of new polymer materials.
“The functional group tolerance of TBD allows the introduction of different polymerizable groups (e.g.olefin) to the ester products (Scheme 21), which provides a number of opportunities in the production of new polymer materials.”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [439]
Leibfarth reported a very efficient way to recycle PLAs and PGA to small esters using TBD as the catalyst; with only 1.5 equivalents of alcohol per ester bond, quantitative alcoholysis to small esters was observed in only 2 min at room temperature with nearly complete retention of stereochemistry.
“Leibfarth reported a very efficient way to recycle PLAs and PGA to small esters using TBD as the catalyst.439 With only 1.5 equivalents of alcohol per ester bond, quantitative alcoholysis to small esters was observed in only 2 min at room temperature with nearly complete retention of stereochemistry.”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [439]
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- Authors
- Leibfarth, F. A., Moreno, N., Hawker, A. P., & Shand, J. D.
- Affiliations
- University of California, Santa Barbara (US)
- Corresponding author
- Leibfarth, Frank A.
- ORCID
- Leibfarth, Frank A.
- Venue
- Journal of Polymer Science Part A: Polymer Chemistry
- Publisher
- Wiley
- Published
- 2012-08-20
- Volume
- 50
- Issue
- 23
- Pages
- 4814-4822
- ISSN
- 0887-624X (ISSN-L)
- 1099-0518
- OpenAlex
- W2101576104
- Cited by
- 139
- References
- 68
- Citations by year
- 2026: 16 · 2025: 19 · 2024: 16 · 2023: 15 · 2022: 18 · 2021: 10 · 2020: 14 · 2019: 8 · 2018: 7 · 2017: 3 · 2016: 3 · 2015: 3 · 2014: 5 · 2013: 2
- FWCI
- 1.30
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Polymer Science Part A Polymer Chemistry (publishedVersion)
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
- Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
- Keywords
- polylactic acid, polyglycolic acid, depolymerization, organocatalysis, transesterification, lactate esters, value-added chemicals, biodegradable plastics, polyester depolymerization, polymer waste valorization
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