Next Generation of Zinc Bisguanidine Polymerization Catalysts towards Highly Crystalline, Biodegradable Polyesters
Open accessAbstract
Polylactide and polycaprolactone are both biodegradable polymers produced through metal‐catalyzed ring‐opening polymerization. For a truly sustainable lifecycle of these polymers it is essential to replace the industrially used cytotoxic catalyst tin(II) bis(2‐ethylhexanoate) [Sn(Oct) 2 ] with non‐toxic alternatives. Here, we report the fastest known robust catalyst in the polymerization of lactide and ϵ‐caprolactone. This zinc guanidine catalyst can polymerize non‐purified technical rac ‐lactide and ϵ‐caprolactone in the melt at different [M]/[I] ratios with fast rate constants, high molar masses, and high yields in a short time, leading to colorless, transparent polymer. Moreover, we report that polylactide and polycaprolactone produced by zinc‐guanidine complexes have favorably high crystallinities. In fact, the obtained polylactide shows a more robust degradation profile than its Sn(Oct) 2 ‐catalysed equivalent due to a higher degree of crystallinity.
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Tin(ii) octanoate remains the only commercially applied catalyst for the production of polylactide.
“tin(ii)octanoate remains the only commercially applied catalyst for the production of polylactide”
From Iron( <scp>ii</scp> ) carboxylates and simple carboxamides: an inexpensive and modular catalyst system for the synthesis of PLLA and PLLA-PCL block copolymers (2023) · cites this paper as [31]
The Introduction says tin(II) bis(2-ethylhexanoate), also called tin(II) octanoate, is used industrially to produce polylactide. It does not establish that it is the only commercially applied catalyst. (LLM, conf=0.87)
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- Authors
- Hermann, A., Hill, S., Metz, A., Heck, J., Hoffmann, A., Hartmann, L., & Herres‐Pawlis, S.
- Affiliations
- RWTH Aachen University (DE)
- Heinrich Heine University Düsseldorf (DE)
- Corresponding author
- Hartmann, Laura
- Herres‐Pawlis, Sonja
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2020-10-22
- Volume
- 59
- Issue
- 48
- Pages
- 21778-21784
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- PMC
- PMC7814670
- OpenAlex
- W3087380040
- Cited by
- 109
- References
- 65
- Citations by year
- 2026: 15 · 2025: 18 · 2024: 15 · 2023: 20 · 2022: 23 · 2021: 18
- FWCI
- 3.97
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Angewandte Chemie International Edition (publishedVersion, cc-by-nc-nd)
- Europe PMC (PubMed Central) (publishedVersion, other-oa)
- PubMed Central (publishedVersion, cc-by-nc-nd)
- PubMed (publishedVersion)
- RWTH Publications (RWTH Aachen) (submittedVersion, other-oa)
- Funders
- Universität zu Köln
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
- Keywords
- polylactic acid, polycaprolactone, ring-opening polymerization, biodegradable polyesters, catalyst toxicity, lactide, ε-caprolactone, polymer crystallinity, polymer degradation, melt polymerization
- MeSH terms
- Polyesters, Zinc, Molecular Structure, Guanidine, Coordination Complexes, Polymerization
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