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

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: 06 May 2020 13:17
URI: http://eprints.nottingham.ac.uk/id/eprint/56309

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