Journal
CHEMISTRYSELECT
Volume 1, Issue 17, Pages 5538-5541Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201600055
Keywords
Acrolein; isoprene; p-xylene; terephthalic acid; bio-based
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Funding
- Biomass Research and Development Initiative Competitive Grant from the USDA National Institute of Food and Agriculture [2001-10006-3058]
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There exist significant challenges in the synthesis of solely biomass-derived p-xylene and terephthalic acid (TPA), the monomer precursors of polyethylene terephthalate (PET). Herein, we describe a flexible synthetic route to prepare either p-xylene or TPA from biomass-derived isoprene and acrolein, which avoids harsh reaction conditions such as high pressure or extreme low temperature. The route starts from 4-methylcyclohex- 3-enecarbaldehyde, the product of Diels-Alder reaction of isoprene and acrolein. Then p-xylene was successfully obtained by subsequent reduction and aromatization reactions using either environment-friendly solvents or in neat. In addition, this route was further modified for a process to prepare both p-xylene and TPA. By using the same intermediate after Diels-Alder reaction, an aromatization reaction was followed by a reduction to p-xylene or an oxidation to directly TPA in an overall yield of 32% over three steps.
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