Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, USA.
Chemistry. 2011 Oct 24;17(44):12452-7. doi: 10.1002/chem.201101580. Epub 2011 Sep 16.
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.
聚对苯二甲酸乙二醇酯（PET）是一种全球需求量很大的聚合物材料。传统上，PET 是由基于化石燃料的材料生产的。在此，我们探索了仅使用生物可再生资源生产 PET 的可持续方法的可行性。具体来说，2,5-二甲基呋喃（通过 5-（羟甲基）糠醛从木质纤维素生物质中获得）和丙烯醛（由生物柴油生产的副产品甘油制成）被转化为关键中间体对二甲苯（对苯二甲酸的前体）。该合成由顺序 Diels-Alder 反应、氧化、脱水和脱羧组成。特别是，关键的第一步，Diels-Alder 反应，进行了详细研究，以提供有用的动力学和热力学数据。尽管发现该反应需要低温才能有效地进行，但这在工业规模的经济可行性方面存在限制，但该概念得到了实现，并且通过四步反应以 34%的总收率获得了生物衍生的对二甲苯。
