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Bottle-grade polyethylene furanoate from ring-opening polymerisation of cyclic oligomers.

ABSTRACT: Polyethylene furanoate (PEF) represents a promising renewable resource-based bioplastic as replacement for fossil-based polyethylene terephthalate (PET) with improved material properties. However, the synthesis of PEF through conventional polycondensation remains challenging, since the time-intensive reaction leads to degradation and undesired discolouration of the product. Here we show the successful rapid synthesis of bottle-grade PEF via ring-opening polymerisation (ROP) from cyclic PEF oligomers within minutes, thereby avoiding degradation and discolouration. The melting point of such mixture of cyclic oligomers lies around 370?°C, well above the degradation temperature of PEF (~329?°C). This challenge can be overcome, exploiting the self-plasticising effect of the forming polymer itself (which melts around 220?°C) by initiation in the presence of a high boiling, yet removable, and inert liquid plasticiser. This concept yields polymer grades required for bottle applications (Mn?>?30?kg?mol-1, conversion > 95%, colour-free products), and can be extended to other diffusion-limited polymer systems.

SUBMITTER: Rosenboom JG

PROVIDER: S-EPMC6057881 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Bottle-grade polyethylene furanoate from ring-opening polymerisation of cyclic oligomers.

Rosenboom Jan-Georg JG Hohl Diana Kay DK Fleckenstein Peter P Storti Giuseppe G Morbidelli Massimo M

Nature communications 20180724 1

Polyethylene furanoate (PEF) represents a promising renewable resource-based bioplastic as replacement for fossil-based polyethylene terephthalate (PET) with improved material properties. However, the synthesis of PEF through conventional polycondensation remains challenging, since the time-intensive reaction leads to degradation and undesired discolouration of the product. Here we show the successful rapid synthesis of bottle-grade PEF via ring-opening polymerisation (ROP) from cyclic PEF oligo ...[more]

PMID: 30042388

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Project description:BACKGROUND:Development of circular economy requires significant advances in the technologies for valorisation of waste, as waste becomes new feedstock. Food waste is a particularly important feedstock, containing large variation of complex chemical functionality. Although most food waste sources are complex mixtures, waste from food processing, no longer suitable for the human food chain, may also represent relatively clean materials. One such material requiring valorisation is cocoa butter. RESULTS:Epoxidation of a triglyceride from a food waste source, processing waste cocoa butter, into the corresponding triglyceride epoxide was carried out using a modified Ishii-Venturello catalyst in batch and continuous flow reactors. The batch reactor achieved higher yields due to the significant decomposition of hydrogen peroxide in the laminar flow tubular reactor. Integral and differential models describing the reaction and the phase transfer kinetics were developed for the epoxidation of cocoa butter and the model parameters were estimated. Ring-opening of the epoxidised cocoa butter was undertaken to provide polyols of varying molecular weight (Mw = 2000-84 000 Da), hydroxyl value (27-60 mg KOH g-1) and acid value (1-173 mg KOH g-1), using either aqueous ortho-phosphoric acid (H 3 PO 4) or boron trifluoride diethyl etherate (BF 3·OEt2)-mediated oligomerisation in bulk, using hexane or tetrahydrofuran (THF) as solvents. The thermal and tensile properties of the polyurethanes obtained from the reaction of these polyols with 4,4'-methylene diphenyl diisocyanate (MDI) are described. CONCLUSION:The paper presents a complete valorisation scheme for a food manufacturing industry waste stream, starting from the initial chemical transformation, developing a process model for the design of a scaled-up process, and leading to synthesis of the final product, in this case a polymer. This work describes aspects of optimisation of the conversion route, focusing on clean synthesis and also demonstrates the interdisciplinary nature of the development projects, requiring input from different areas of chemistry, process modelling and process design. © 2017 The Authors. Journal of Chemical Technology & Biotechnology published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

Dataset Information

Bottle-grade polyethylene furanoate from ring-opening polymerisation of cyclic oligomers.

Publications

Bottle-grade polyethylene furanoate from ring-opening polymerisation of cyclic oligomers.

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