New polymer building blocks from bio-based methyl vinyl glycolate

Bo Michael Jessen*

*Corresponding author for this work

Research output: Book/ReportPh.D. thesis

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Abstract

This thesis contains six individual chapters and an appendix. The first chapter contains the general background and plan of this project, research and why it was pursued. Chapter two to four describe the work performed during this project.

Chapter 1 Introduction is a general chapter, describing why this project was started, what has been performed previously, and what is prior art. The chapter covers some of the market for bio-chemicals, chemicals including lactic acid that can be considered an analogue to methyl vinyl glycolate (MVG) and is an established polymer building block on the current market. The chemistry of polymerisation and envisioned
applications of the monomers modified from MVG are described.

Chapter 2 Methyl vinyl glycolate modifications covers most of the chemistry performed on MVG and the subsequent modifications. It describes the successes and failures of the project and how we envision some of the monomers can be used in polymerisation. It describes the scale of the monomers we were able to produce in relative amount, which were shipped out for testing.

Chapter 3 Allylic acetate rearrangement describes the work with the rearrangement of allylic moieties derived from MVG. We studied the rearrangement pathway and proposed a mechanism. In this chapter, possible conversion to produce new monomers from the rearrangement of MVG derived compounds is also described.

Chapter 4 Diels Alder reactions contains the Diels Alder reactions that the oxidised MVG (methyl 2-oxobut-3-enoate) is able to undergo. The compound is a good dienophile, which can produce a range of new undiscovered compounds through a pericyclic cycloaddition.

Chapter 5 Final remarks summarises the work performed and the achievements during this project. It shows the multiple compounds currently available from MVG as a platform.

Chapter 6 Experimental describes the procedures for synthesising all the compounds tested and uncovered during this project.

Appendix contains some of the data collected and the work performed at my external stay at Perstorp AB (Appendix C).
Original languageEnglish
Place of PublicationKgs. Lyngby
PublisherTechnical University of Denmark
Number of pages189
Publication statusPublished - 2019

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