Unique Base-Initiated Depolymerization of Limonene-Derived Polycarbonates

The depolymerization of poly­(limonene carbonate) (PLC) initiated by 1,5,7-triazabicyclo[4.4.0]­dec-5-ene (TBD) was investigated. The strong organic base TBD was capable of deprotonating the OH-terminated PLC, leading to fast degradation via backbiting reactions at high temperature. An interesting f...

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Bibliographic Details
Published in:ACS macro letters 2017-07, Vol.6 (7), p.684-688
Main Authors: Li, Chunliang, Sablong, Rafaël J, van Benthem, Rolf A. T. M, Koning, Cor E
Format: Article
Language:English
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Summary:The depolymerization of poly­(limonene carbonate) (PLC) initiated by 1,5,7-triazabicyclo[4.4.0]­dec-5-ene (TBD) was investigated. The strong organic base TBD was capable of deprotonating the OH-terminated PLC, leading to fast degradation via backbiting reactions at high temperature. An interesting feature of the base-initiated breakdown of PLC lies in the quantitative depolymerization into the corresponding initial limonene oxide monomer. This result implies the complete back-to-monomer recyclability of the fully biobased PLC, which accordingly can be considered as a really sustainable material. Additionally, the stability of PLC when exposed to TBD was enhanced by an end-capping reaction, which further supported the proposed degradation pathway.
ISSN:2161-1653
2161-1653
DOI:10.1021/acsmacrolett.7b00310