New renewably-sourced polyesters from limonene-derived monomers

Megan Thomsett; Jonathan Christopher Moore; Antoine Buchard; Robert Stockman; Steven M Howdle

doi:10.1039/C8GC02957A

New renewably-sourced polyesters from limonene-derived monomers

Megan Thomsett, Jonathan Christopher Moore, Antoine Buchard, Robert Stockman, Steven M Howdle

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The functionalisation of limonene has enabled the synthesis of two renewably-sourced monomers for the formation of terpene-derived polyesters. Three methods for the synthesis of the novel hydroxy-acid 6 are reported and their green-credentials scrutinised through comparison of their sustainability-metrics. Step-growth homo-polymerisation of 6 is demonstrated to yield a low molecular weight (2.6 kDa) novel polyester with 100% of its carbon content originating from the terpene starting material. The corresponding diol 2 is shown to act as a co-monomer with a renewable diacid. The resultant polyesters display impressive M ns of up to 30 kDa with T gs between -6 and 24 °C. These materials have been shown to depolymerise under basic conditions for reclamation of the diol monomer 2.

Original language	English
Pages (from-to)	149-156
Number of pages	8
Journal	Green Chemistry
Volume	21
Issue number	1
DOIs	https://doi.org/10.1039/C8GC02957A
Publication status	Published - 7 Jan 2019

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10.1039/C8GC02957A

Cite this

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title = "New renewably-sourced polyesters from limonene-derived monomers",

abstract = "The functionalisation of limonene has enabled the synthesis of two renewably-sourced monomers for the formation of terpene-derived polyesters. Three methods for the synthesis of the novel hydroxy-acid 6 are reported and their green-credentials scrutinised through comparison of their sustainability-metrics. Step-growth homo-polymerisation of 6 is demonstrated to yield a low molecular weight (2.6 kDa) novel polyester with 100% of its carbon content originating from the terpene starting material. The corresponding diol 2 is shown to act as a co-monomer with a renewable diacid. The resultant polyesters display impressive M ns of up to 30 kDa with T gs between -6 and 24 °C. These materials have been shown to depolymerise under basic conditions for reclamation of the diol monomer 2.",

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AB - The functionalisation of limonene has enabled the synthesis of two renewably-sourced monomers for the formation of terpene-derived polyesters. Three methods for the synthesis of the novel hydroxy-acid 6 are reported and their green-credentials scrutinised through comparison of their sustainability-metrics. Step-growth homo-polymerisation of 6 is demonstrated to yield a low molecular weight (2.6 kDa) novel polyester with 100% of its carbon content originating from the terpene starting material. The corresponding diol 2 is shown to act as a co-monomer with a renewable diacid. The resultant polyesters display impressive M ns of up to 30 kDa with T gs between -6 and 24 °C. These materials have been shown to depolymerise under basic conditions for reclamation of the diol monomer 2.

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