Investigations into the Synthetic Modifications of Terpenes for the Synthesis of Renewable Polyesters

This thesis details the synthesis of four novel terpene-derived monomers via the derivatisation of a-pinene and limonene (two of the most abundant terpenes). The monomers have been used in the synthesis of sustainable polyesters, which all contain a unique cyclohexane ring in their backbone. The...

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Main Author: Thomsett, Megan
Format: Thesis (University of Nottingham only)
Language:English
Published: 2019
Subjects:
Online Access:https://eprints.nottingham.ac.uk/56309/
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author Thomsett, Megan
author_facet Thomsett, Megan
author_sort Thomsett, Megan
building Nottingham Research Data Repository
collection Online Access
description This thesis details the synthesis of four novel terpene-derived monomers via the derivatisation of a-pinene and limonene (two of the most abundant terpenes). The monomers have been used in the synthesis of sustainable polyesters, which all contain a unique cyclohexane ring in their backbone. 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 a novel hydroxy-acid are reported and their green credentials scrutinised through comparison of their sustainability-metrics. Stepgrowth homo-polymerisation of the hydroxy-acid is demonstrated to yield a low molecular weight novel polyester with 100% of its carbon content originating from the terpene starting material. The corresponding limonene diol is shown to act as a comonomer with a renewable diacid. The resultant polyesters display impressive Mns of up to 30 kDa with Tgs between -6 and 24 oC. The degradation of these materials were shown to allow recyclability of the diol monomer. a-Pinene was used for the synthesis of two polyols, which served as comonomers with a renewable diacid, enabling the synthesis of two novel polyesters with high Tgs. The corresponding enantiomers of the a-pinene derived polymers were blended to form stereocomplexes, leading to improved thermal properties of the polyester.
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spelling nottingham-563092025-02-28T14:26:52Z https://eprints.nottingham.ac.uk/56309/ Investigations into the Synthetic Modifications of Terpenes for the Synthesis of Renewable Polyesters Thomsett, Megan This thesis details the synthesis of four novel terpene-derived monomers via the derivatisation of a-pinene and limonene (two of the most abundant terpenes). The monomers have been used in the synthesis of sustainable polyesters, which all contain a unique cyclohexane ring in their backbone. 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 a novel hydroxy-acid are reported and their green credentials scrutinised through comparison of their sustainability-metrics. Stepgrowth homo-polymerisation of the hydroxy-acid is demonstrated to yield a low molecular weight novel polyester with 100% of its carbon content originating from the terpene starting material. The corresponding limonene diol is shown to act as a comonomer with a renewable diacid. The resultant polyesters display impressive Mns of up to 30 kDa with Tgs between -6 and 24 oC. The degradation of these materials were shown to allow recyclability of the diol monomer. a-Pinene was used for the synthesis of two polyols, which served as comonomers with a renewable diacid, enabling the synthesis of two novel polyesters with high Tgs. The corresponding enantiomers of the a-pinene derived polymers were blended to form stereocomplexes, leading to improved thermal properties of the polyester. 2019-06-17 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/56309/1/Thesis%20-%20Final%20Corrections.pdf Thomsett, Megan (2019) Investigations into the Synthetic Modifications of Terpenes for the Synthesis of Renewable Polyesters. PhD thesis, University of Nottingham. terpenes monomers a-pinene polyesters
spellingShingle terpenes
monomers
a-pinene
polyesters
Thomsett, Megan
Investigations into the Synthetic Modifications of Terpenes for the Synthesis of Renewable Polyesters
title Investigations into the Synthetic Modifications of Terpenes for the Synthesis of Renewable Polyesters
title_full Investigations into the Synthetic Modifications of Terpenes for the Synthesis of Renewable Polyesters
title_fullStr Investigations into the Synthetic Modifications of Terpenes for the Synthesis of Renewable Polyesters
title_full_unstemmed Investigations into the Synthetic Modifications of Terpenes for the Synthesis of Renewable Polyesters
title_short Investigations into the Synthetic Modifications of Terpenes for the Synthesis of Renewable Polyesters
title_sort investigations into the synthetic modifications of terpenes for the synthesis of renewable polyesters
topic terpenes
monomers
a-pinene
polyesters
url https://eprints.nottingham.ac.uk/56309/