Premium
A Comprehensive Study on the Reductive Amination of 5‐Hydroxymethylfurfural into 2,5‐Bisaminomethylfuran over Raney Ni Through DFT Calculations
Author(s) -
Zhou Kuo,
Liu Haiyan,
Shu Huimin,
Xiao Shuwen,
Guo Dechao,
Liu Yingxin,
Wei Zuojun,
Li Xiaonian
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900304
Subject(s) - furfuryl alcohol , furfural , reductive amination , chemistry , catalysis , dehydrogenation , amination , yield (engineering) , dihydroxyacetone , hydroxymethylfurfural , organic chemistry , raney nickel , adsorption , metal , inorganic chemistry , materials science , glycerol , metallurgy
Reductive amination of furfuryl alcohol, furfural and 5‐hydroxymethylfurfural (5‐HMF) were carried out on various metal catalysts. Over Raney Ni catalyst, we obtained the highest furfurylamine yields of 81.8 % and 94.0 % from furfuryl alcohol in absence and presence of H 2 , respectively. While furfural was used as the substrate, 100 % yield of furfurylamine could be achieved over Raney Ni under rather moderate conditions. Although 5‐HMF was completely converted over all catalysts used, the highest yield of 2,5‐bisaminomethylfuran (60.7 %) was obtained over Raney Ni at 160 °C in 12 h. The DFT calculations on the adsorption behavior of NH 3 and H 2 on different metal surfaces showed that the difference of the adsorption energy between NH 3 and H 2 on Ni is lower than those of other metals, indicating that less metal active sites on Ni surface is occupied by NH 3 , which leaves more active sites for dehydrogenation/hydrogenation reactions and in the end promotes the reductive amination reactions.