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On the Diels-Alder approach to solely biomass-derived polyethylene terephthalate (PET): conversion of 2,5-dimethylfuran and acrolein into p-xylene.

Chemistry (Weinheim an der Bergstrasse, Germany) (2011-09-17)
Mika Shiramizu, F Dean Toste
ABSTRACT

Polyethylene terephthalate (PET) is a polymeric material with high global demand. Conventionally, PET is produced from fossil-fuel-based materials. Herein, we explored the feasibility of a sustainable method for PET production by using solely bio-renewable resources. Specifically, 2,5-dimethylfuran (derived from lignocellulosic biomass through 5-(hydroxymethyl)furfural) and acrolein (produced from glycerol, a side product of biodiesel production) were converted into the key intermediate p-xylene (a precursor of terephthalic acid). This synthesis consists of a sequential Diels-Alder reaction, oxidation, dehydration, and decarboxylation. In particular, the pivotal first step, the Diels-Alder reaction, was studied in detail to provide useful kinetic and thermodynamic data. Although it was found that this reaction requires low temperature to proceed efficiently, which presents a limitation on economic feasibility on an industrial scale, the concept was realized and bio-derived p-xylene was obtained in 34% overall yield over four steps.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2,5-Dimethylfuran, 99%
Supelco
p-Xylene, analytical standard
Sigma-Aldrich
p-Xylene, anhydrous, ≥99%
Supelco
p-Xylene solution, certified reference material, 5000 μg/mL in methanol
Supelco
p-Xylene, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
p-Xylene, suitable for HPLC, ≥99%
Sigma-Aldrich
p-Xylene, puriss. p.a., ≥99.0% (GC)
Sigma-Aldrich
p-Xylene, ReagentPlus®, 99%