Unique base-initiated depolymerization of limonene-derived polycarbonates

C. Li; R.J. Sablong; R.A.T.M. van Benthem; C.E. Koning

doi:10.1021/acsmacrolett.7b00310

Unique base-initiated depolymerization of limonene-derived polycarbonates

C. Li, R.J. Sablong, R.A.T.M. van Benthem, C.E. Koning

Physical Chemistry

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Abstract

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.

Original language	English
Pages (from-to)	684-688
Number of pages	5
Journal	ACS Macro Letters
Volume	6
Issue number	7
DOIs	https://doi.org/10.1021/acsmacrolett.7b00310
Publication status	Published - 18 Jul 2017

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title = "Unique base-initiated depolymerization of limonene-derived polycarbonates",

abstract = "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.",

author = "C. Li and R.J. Sablong and {van Benthem}, R.A.T.M. and C.E. Koning",

year = "2017",

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journal = "ACS Macro Letters",

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T1 - Unique base-initiated depolymerization of limonene-derived polycarbonates

AU - Li, C.

AU - Sablong, R.J.

AU - van Benthem, R.A.T.M.

AU - Koning, C.E.

PY - 2017/7/18

Y1 - 2017/7/18

N2 - 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.

AB - 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.

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Unique base-initiated depolymerization of limonene-derived polycarbonates

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