Ring‐closing depolymerization of poly(ε‐caprolactone)

Nelißen, Marion; Keul, Helmut; Höcker, Hartwig

doi:10.1002/macp.1995.021960521

Cited by 39biodegradable polymer synthesis and propertiesPolymer crystallization and propertiesPolymer composites and self-healing

Ring‐closing depolymerization of poly(ε‐caprolactone)

Nelißen, Marion, Keul, Helmut, Höcker, Hartwig·1995·Macromolecular Chemistry and Physics

DOI 10.1002/macp.1995.021960521

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Abstract

Ring‐closing depolymerization of poly(ε‐caprolactone) in toluene solution with catalytic amounts of Bu 2 Sn(OMe)2 results in a mixture of cyclic oligomers, the equilibrium concentration of which corresponds to the concentration predicted according to the Jacobson‐Stockmayer theory. ε‐Caprolactone, however, is absent from this reaction mixture. When poly(ε‐caprolactone) is depolymerized in the melt at 260°C in the presence of a catalyst, beside ε‐caprolactone its cyclic dimer and trimer are distilled off. The composition is dependent on the catalyst used, e.g., Bu 2 Sn(OMe)2 produces 95,4 wt.‐% of ε‐caprolactone and 3,7 wt.‐% of its dimer while with Ti(OiPr)4 (iPr: isopropyl) 51,4 wt.‐% ε‐caprolactone and 49,6 wt.‐% of its dimer are obtained. Block copolymers containing poly(ε‐caprolactone) result in a similar product distribution, however, the second block may influence the rate of decomposition. The activation energy of the catalysed (0,5 mol‐% Bu 2 Sn(OMe)2) and uncatalysed ring‐closing depolymerization were determined to be 63 kJ/mol, and 87 kJ/mol, respectively.

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When the depolymerization of PCL was performed in toluene with Bu2Sn(OMe)2 at 110 °C, the products were a mixture of cyclic oligomers with little formation of CL.
“When the depolymerization of PCL was performed in toluene with Bu2Sn(OMe)2 at 110 °C, the products were, however, a mixture of cyclic oligomers with little formation of CL. 455”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [455]

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Authors: Nelißen, M., Keul, H., & Höcker, H.
Affiliations: RWTH Aachen University (DE)
Corresponding author: Höcker, Hartwig
ORCID: Keul, Helmut
Venue: Macromolecular Chemistry and Physics
Publisher: Wiley
Published: 1995-05
Volume: 196
Issue: 5
Pages: 1645-1661
ISSN: 1022-1352 (ISSN-L)
1521-3935
DOI: 10.1002/macp.1995.021960521
OpenAlex: W2169774210
Cited by: 39
References: 20
Citations by year: 2026: 4 · 2025: 7 · 2024: 2 · 2023: 2 · 2022: 3 · 2021: 1 · 2020: 2 · 2017: 1 · 2016: 1 · 2015: 2 · 2014: 1
FWCI: 0.00
Type: journal article
Language: en
Open access: closed
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor, 2872 d)
Locations: Macromolecular Chemistry and Physics (publishedVersion)
RWTH Publications (RWTH Aachen) (submittedVersion)
Topics: Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
Keywords: polycaprolactone, cyclic oligomers, titanium isopropoxide, cyclic dimers, cyclic trimer, block copolymers, activation energy, toluene solution

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Ring‐closing depolymerization of poly(ε‐caprolactone)

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