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Synthesis of Bis(hydroxylmethylfurfuryl)amine Monomers from 5-Hydroxymethylfurfural
Zhanwei Xu1, Peifang Yan1, Kairui Liu1
1Dalian National Lab for Clean Energy, State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, 116023, Dalian, China.
Abstract:
We report the synthesis of bis(hydroxylmethylfurfuryl)amine (BHMFA) from 5-hydroxymethylfurfural (5-HMF) by reacting 5-HMF with primary amines in the presence of homogeneous Ru(II) catalysts having sterically strained ligands. BHMFA is a group of furan-based monomers that offer great potential to form functional biopolymers with tunable properties. A range of primary amines, such as aliphatic and benzyl amines, are readily converted with 5-HMF to form the corresponding BHMFA in good yields. The reaction proceeds through reductive amination of 5-HMF with primary amine to form secondary amine, followed by reductive amination of 5-HMF with in situ generated secondary amine to produce BHMFA.
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