We disclose in this study a Ni
6
AlO
x
catalyst prepared by coprecipitation
for the reductive amination
of biomass-derived aldehydes and ketones in aqueous ammonia under
mild reaction conditions. The catalyst exhibited 99% yield toward
5-aminomethyl-2-furylmethanol in the reaction of 5-hydroxymethyl furfural
with ammonia at 100 °C for 6 h under 1 bar H
2
. The
catalyst was further extended to the reductive amination of a library
of aromatic and aliphatic aldehydes and ketones with a yield in the
range 81–90% at optimized reaction conditions. Besides, 5-hydroxymethylfurfural
could react with a library of primary and secondary amines with yields
in the range 76–88%. The catalyst could be easily recycled
and reused without apparent loss of activity in four consecutive runs.
The
reductive N-formylation of amines using CO2 and hydrogen is a promising means of incorporating CO2 into value-added chemicals. To date, there has been a lack
of heterogeneous catalyst systems that are sufficiently active and
selective for N-formylation of primary amines with
CO2 and H2. For the first time, we report that
a highly active palladium nanoparticle supported on an hydroxyl group-functionalized
carbon material has been designed for the N-formylation
of aliphatic primary amines with CO2 and H2.
XPS, XRD, FT-Raman, and TEM characterizations revealed the adsorbing
of Pd(NH3)
x
Cl
y
onto the carbon support during catalyst preparation, followed
by in situ reduction to generate active nano-Pd particles. The catalytic
activity of the Pd/C catalysts can be tuned efficiently by the hydroxyl
group, which can modulate the hydrophilic/hydrophobic properties of
the carbon surface, and promote the adsorption of CO2 and
the amines near the Pd sites. The results described here may promote
the design of an active catalyst for CO2 recycling and N-formyl amine synthesis.
A simple and highly efficient method was developed for one pot transformation of 5-(hydroxymethyl)furfural (5-HMF) into 2,5-bis(aminomethyl)furan (BAF) over bifunctional Cu4Ni1Al4Ox catalyst using two-stage reaction process, affording the BAF in 85.9% yield.
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