Efficient Synthesis of Pharmaceutical Intermediates from Biomass-Derived Aldehydes and Ketones over Robust NixAl Nanocatalysts

被引:16
|
作者
Zhang, Jia [1 ,2 ]
Yang, Jian [1 ,2 ]
Li, Xuemei [1 ]
Liu, Hailong [1 ]
Wang, Aiqin [3 ]
Xia, Chungu [1 ]
Chen, Jing [1 ]
Huang, Zhiwei [1 ]
机构
[1] Chinese Acad Sci, Suzhou Res Inst LICP, Lanzhou Inst Chem Phys LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Chinese Acad Sci, Lanzhou Inst Chem Phys, Key Lab Clay Mineral Appl Res Gansu Prov, Lanzhou 730000, Peoples R China
来源
基金
中国国家自然科学基金;
关键词
NixAl nanocatalysts; reductive amination; pharmaceutical intermediates; N-1,N-1-diethyl-1,4-pentanediamine; structure-activity relationship; REDUCTIVE AMINATION; SELECTIVE SYNTHESIS; ALCOHOL AMINATION; GENERAL-SYNTHESIS; PRIMARY AMINES; CATALYSTS; METHANE; CHEMICALS; CONVERSION; OXIDATION;
D O I
10.1021/acssuschemeng.2c00115
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Heterogeneous catalytic reductive amination of biomass-based carbonyl compounds is a highly attractive strategy to realize green and sustainable amine synthesis under mild conditions. Herein, N-1,N-1-diethyl-1,4-pentanediamine, a key side chain of chloroquine pharmaceuticals, was highly selectively synthesized through the reductive amination of 5-diethylamino-2-pentanone on active NixAl nanocatalysts with different Ni/Al molar ratios prepared by the simple co-precipitation method. The Ni1Al catalyst presented the highest target diamine product yield (up to 99%) among the NixAl catalysts. This catalyst also exhibited remarkable stability in a fixed-bed reactor without deactivation after 200 h of continuous operation, thanks to its good anti-sintering and anti-oxidation properties. Systematic structure characterizations and catalytic activity tests showed that their catalytic activity depended sensitively on the Ni/Al molar ratio, which governed the dispersion, reducibility, and surface acidity of the catalysts. The synergic catalysis of highly dispersed active Ni-0 nanoparticles with abundant adjacent surface Lewis acidic sites accounted for the outstanding catalytic performance of the Ni1Al catalyst. Moreover, such novel catalysts also presented high activity in the reductive amination of several other biomass-derived aldehydes and ketones to produce the corresponding amines, achieving 91-99% yields under mild conditions of 80-100 degrees C and 1-2 MPa.
引用
收藏
页码:5526 / 5537
页数:12
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