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

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Thomsett, Megan (2019) Investigations into the Synthetic Modifications of Terpenes for the Synthesis of Renewable Polyesters. PhD thesis, University of Nottingham.

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Abstract

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.

Item Type: Thesis (University of Nottingham only) (PhD)
Supervisors: Stockman, Robert
Howdle, Steven
Keywords: terpenes, monomers, a-pinene, polyesters
Subjects: Q Science > QD Chemistry > QD241 Organic chemistry > QD415 Biochemistry
T Technology > TP Chemical technology > TP1080 Polymers and polymer manufacture
Faculties/Schools: UK Campuses > Faculty of Science > School of Chemistry
Item ID: 56309
Depositing User: Thomsett, Megan
Date Deposited: 05 Nov 2019 14:19
Last Modified: 23 Nov 2023 08:13
URI: https://eprints.nottingham.ac.uk/id/eprint/56309

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