title: On the Diels-Alder approach to solely biomass-derived polyethylene terephthalate (PET): conversion of 2,5-dimethylfuran and acrolein into p-xylene.
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.
authors.affiliation: Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, USA.
authors.forename: Mika
authors.initials: M
authors.lastname: Shiramizu
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
mesh_terms: D000171:Acrolein / Q000737:chemistry*; D056804:Biofuels; D018533:Biomass; D002384:Catalysis; D005662:Furaldehyde / Q000031:analogs & derivatives / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D005990:Glycerol / Q000737:chemistry; D015394:Molecular Structure; D011093:Polyethylene Terephthalates / Q000737:chemistry*; D014992:Xylenes / Q000737:chemistry*
chemical_list: D056804:Biofuels; D005663:Furans; D011093:Polyethylene Terephthalates; D014992:Xylenes; C031286:4-xylene; C008046:5-hydroxymethylfurfural; D000171:Acrolein; D005662:Furaldehyde; C037555:2,5-dimethylfuran; D005990:Glycerol