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Catalytic oxidation of 5-hydroxymethylfurfural into 2,5-diformylfuran using V-containing heteropoly acid catalysts
Reaction Kinetics, Mechanisms and Catalysis ( IF 1.7 ) Pub Date : 2020-05-05 , DOI: 10.1007/s11144-020-01782-z
Yulia Rodikova , Elena Zhizhina

2,5-Diformylfuran (DFF) is an attractive and challenging compound that can be synthesized with good selectivity by the oxidation of bio-based 5‐hydroxymethylfurfural (5-HMF) using specific catalysts. Vanadium-containing heteropoly acids (PMoV HPAs) are highly active oxidation catalysts whose activity can be tuned by changing vanadium(V) (VV) content. This study reports the preparation of a number of PMoV HPAs with different VV amount and type of outer-sphere cation and investigating their catalytic performance in 5-HMF-to-DFF conversion. The characterization of synthesized HPAs by simple instrumental methods (pH-measurement, potentiometry, and titration analysis) and NMR revealed retaining Keggin structure and increasing oxidation potential with rising VV amount. The complete optimization of reaction conditions allowed one to reach a DFF yield of 92% using Co2H6P3Mo18V7O84 at 110 °C in water/MIBK for 90 min under atmospheric pressure. The described method of 5-HMF oxidation is based on using effective soft oxidants that can be easily recycled and reused at least five times without significant loss of catalytic activity.



中文翻译:

含钒杂多酸催化剂将5-羟甲基糠醛催化氧化为2,5-二甲酰呋喃

2,5-二甲酰呋喃(DFF)是一种有吸引力且具有挑战性的化合物,可以通过使用特定的催化剂将生物基5-羟甲基糠醛(5-HMF)氧化而以良好的选择性合成。含钒杂多酸(PMoV HPA)是高活性的氧化催化剂,其活性可以通过改变钒(V)的含量来调节。这项研究报告了许多具有不同V V量和外球阳离子类型的PMoV HPA的制备,并研究了它们在5-HMF到DFF转化中的催化性能。通过简单的仪器方法(pH测量,电位测定和滴定分析)和NMR对合成的HPA进行表征,结果表明保留Keggin结构并随着V V的升高而增加了氧化电势量。完全优化了反应条件,使用Co 2 H 6 P 3 Mo 18 V 7 O 84在110°C的水/ MIBK中于大气压下反应90分钟,可使DFF产率达到92%。所描述的5-HMF氧化方法基于使用有效的软氧化剂,该氧化剂可以容易地循环使用至少五次,而不会明显降低催化活性。

更新日期:2020-05-05
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