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Synthesis of Biobased Diethyl Terephthalate via Diels–Alder Addition of Ethylene to 2,5-Furandicarboxylic Acid Diethyl Ester: An Alternative Route to 100% Biobased Poly(ethylene terephthalate)
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2019-04-16 00:00:00 , DOI: 10.1021/acssuschemeng.8b06196
Joseph K. Ogunjobi 1, 2 , Thomas J. Farmer 1 , C. Robert McElroy 1 , Simon W. Breeden 1 , Duncan J. Macquarrie 1 , David Thornthwaite 3 , James H. Clark 1
Affiliation  

Poly(ethylene terephthalate) (PET) is a ubiquitous thermoplastic currently produced from nonrenewable fossil resources; as such, sustainable biobased routes to the key terephthalate monomer are being widely pursued. Herein is demonstrated a greener solventless route to biobased diethyl terephthalate via a one-pot heterogeneous Lewis acid catalyzed Diels–Alder addition and dehydration of 2,5-furandicarboxylic acid diethyl ester with ethylene, giving yields of terephthalate up to 59% for the key Diels–Alder addition step. A metrics-based comparison against alternative published biobased routes (available from sugars, cellulose and hemicellulose) shows that the clean synthetic pathway developed herein gives a practical atom economy, overall yield and selectivity, making it a viable alternative to routes currently under development.

中文翻译:

通过Diels–Alder加成乙烯到2,5-呋喃二甲酸二乙酯中合成生物基对苯二甲酸二乙酯:替代100%生物基聚对苯二甲酸乙二酯的替代方法

聚对苯二甲酸乙二醇酯(PET)是目前由不可再生的化石资源生产的一种普遍存在的热塑性塑料。因此,正在广泛地寻求通往关键对苯二甲酸酯单体的可持续的生物基途径。本文证明了通过一锅多相路易斯酸催化的Diels-Alder加成和将2,5-呋喃二甲酸二乙酯与乙烯脱水,可以更绿色,无溶剂的方式生产生物基对苯二甲酸二乙酯,从而使关键Diels的对苯二甲酸酯收率高达59% –附加步骤。与其他已发表的基于生物的路线(可从糖,纤维素和半纤维素获得)的基于度量的比较表明,本文开发的清洁合成路线可提供实用的原子经济性,总体收率和选择性,使其成为当前正在开发中的路线的可行替代方案。
更新日期:2019-04-16
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