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Synthesis of 2,5-furandicarboxylic acid by catalytic carbonylation of renewable furfural derived 5-bromofuroic acid
Molecular Catalysis ( IF 3.9 ) Pub Date : 2018-06-23 , DOI: 10.1016/j.mcat.2018.06.015
Guanfei Shen , Sicheng Zhang , Yu Lei , Zhuqi Chen , Guochuan Yin

2,5-Furandicarboxylic acid (FDCA) is regarded as a biomass based alternative to p-phthalic acid in polymer industry. Although it can be produced through catalytic oxidation of hydroxylmethyl furfural (HMF), HMF itself is currently produced in limited volume from mono- and polysaccharides like glucose and fructose, thus blocking the utilization of FDCA to replace p-phthalic acid as monomer in industrial applications. This work presents an alternative route for FDCA synthesis originally from renewable furfural through carbonylation of 5-bromofuroic acid with common palladium catalysts, which achieves >99% yield of FDCA based on HPLC analysis, or above 90% isolated yield in gram scale. The influences of the palladium sources, phosphine ligands and bases were investigated in details, and a simplified mechanism was also presented.



中文翻译:

可再生糠醛衍生的5-溴糠酸的催化羰基化反应合成2,5-呋喃二甲酸

2,5-呋喃二甲酸(FDCA)被认为是聚合物工业中基于生物质的对苯二甲酸替代品。尽管它可以通过羟甲基糠醛(HMF)的催化氧化来生产,但目前HMF本身是由单糖和多糖(如葡萄糖和果糖)以有限的体积生产的,因此阻碍了FDCA在工业应用中取代对苯二甲酸作为单体的用途。 。这项工作为最初由可再生糠醛通过将5-溴糠酸与普通钯催化剂进行羰基化合成FDCA的方法提供了另一种途径,根据HPLC分析,FDCA的收率> 99%,或以克为单位的分离收率超过90%。详细研究了钯源,膦配体和碱的影响,并给出了简化的机理。

更新日期:2018-06-23
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