A Bottom-Up Synthetic Approach to Polyethylene Furanoate Model Compounds

TL;DR

Scientists developed a new method to create model compounds of polyethylene furanoate, a biobased plastic, to help with recycling and understanding its properties.

Contribution

A novel bottom-up synthetic strategy for preparing PEF model compounds using selective protection and esterification techniques.

Findings

A sequence involving FDCA protection, Mukaiyama esterification, and deprotection was developed for selective compound preparation.

The method successfully produced various PEF model compounds, including some not previously described.

Conventional esterification methods were found ineffective for certain target compounds.

Abstract

The growing importance of polyethylene furanoate (PEF)
as a potential
biobased substitute for PET is sparking interest in developing strategies
for the chemical recycling of PEF. Access to appropriate model compounds
is desirable for the development of depolymerization methods as well
as for studying molecular properties and reactivity of PEF models.
Herein, we describe a bottom-up strategy for the efficient and selective
preparation of specific chain fragments from 2,5-furandicarboxylic
acid (FDCA) and monoethylene glycol (MEG). Since conventional esterification
methods according to Fischer and Steglich proved to be ineffective
for certain target compounds, a sequence that consists of one-sided
FDCA protection, Mukaiyama esterification, and subsequent deprotection
was developed. The strategy was successfully applied to the preparation
of various model compounds, including examples that have not yet been
described in the literature.

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