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Hybrid Conversion of 5‐Hydroxymethylfurfural to 5‐Aminomethyl‐2‐furancarboxylic acid: Toward New Bio‐sourced Polymers
ChemCatChem ( IF 4.5 ) Pub Date : 2020-10-30 , DOI: 10.1002/cctc.202001446
Antoine Lancien 1 , Robert Wojcieszak 2 , Eric Cuvelier 2 , Matthieu Duban 1 , Pascal Dhulster 1 , Sébastien Paul 2 , Franck Dumeignil 2 , Renato Froidevaux 1 , Egon Heuson 1
Affiliation  

Hybrid catalysis, which combines chemo‐ and biocatalytic benefits, is an efficient way to address green chemistry principles. 5‐Hydroxymethylfurfural (HMF) is a versatile building block in numerous industrial applications. To date, few studies have described the production of its amine derivatives and their polymers. Finding a good methodology to directly transform HMF to 5‐aminomethyl‐2‐furancarboxylic acid (AMFC) therefore represents an important challenge. After selecting the best oxidation catalyst for HMF conversion to 5‐aldehyde‐2‐furancarboxylic acid and immobilizing a transaminase onto a solid carrier, we implemented the first one‐pot/two‐steps hybrid catalytic process to produce AMFC (77 % yield); this is the most efficient AMFC catalytic production method from HMF reported to date. This process also produced 2,5‐furandicarboxylic acid (21 % yield) as a major secondary product that can be applied to polymer syntheses such as polyethylene furanoate. Herein, we report a novel way to access new biosourced polymers based on HMF oxidized and aminated derivatives.

中文翻译:

5羟甲基糠醛向5氨甲基2呋喃甲酸的杂化转化:寻求新的生物来源聚合物

混合催化结合了化学和生物催化的优点,是解决绿色化学原理的有效方法。5-羟甲基糠醛(HMF)是多种工业应用中的多功能构建基块。迄今为止,很少有研究描述其胺衍生物及其聚合物的生产。因此,寻找一种将HMF直接转化为5-氨基甲基-2-呋喃甲酸(AMFC)的良好方法是一项重要的挑战。在选择最佳的氧化催化剂以将HMF转化为52呋喃甲酸并将转氨酶固定在固体载体上,我们实施了第一个单罐/两步混合催化工艺以生产AMFC(产率为77%);这是迄今为止报道的HMF中最有效的AMFC催化生产方法。这个过程也产生25 -furandicarboxylic酸(21%产率),其可应用于合成聚合物,例如聚乙烯furanoate的主要次要产品。在这里,我们报告了一种新颖的方式来获取基于HMF氧化和胺化衍生物的新型生物来源聚合物。
更新日期:2020-10-30
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