5-hydroxymethylfurfural (HMF) has been successfully valorised into 3-hydroxymethyl cyclopentylamine through a one-pot cascade process in aqueous phase by coupling the hydrogenative ring-rearrangement of HMF into 3-hydroxymethylcyclopentanone (HCPN) followed by the… Click to show full abstract
5-hydroxymethylfurfural (HMF) has been successfully valorised into 3-hydroxymethyl cyclopentylamine through a one-pot cascade process in aqueous phase by coupling the hydrogenative ring-rearrangement of HMF into 3-hydroxymethylcyclopentanone (HCPN) followed by the reductive amination with ammonia. Mono (Ni@C, Co@C) and bimetallic (NiCo@C) nanoparticles with different Ni/Co ratios partially covered by a thin carbon layer were prepared and characterized. Results showed that a NiCo catalyst, (molar ratio Ni/Co=1, ( Ni 0.5 Co 0.5 @C ), displays excellent activity and selectivity for performing the hydrogenative ring-rearrangement of HMF into HCPN (>90% yield). The high selectivity of the catalyst can be attributed to the formation of NiCo alloy structures as hydrogenating sites that limits competitive reactions such the hydrogenation of furan ring and the over-reduction of the formed HPCN. The subsequent reductive amination of HPCN with aqueous ammonia was successfully performed giving the target cyclopentylaminoalcohol in 97 % yield. Moreover, the catalyst exhibits high stability maintaining its activity and selectivity for repeated reaction cycles.
               
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