Flow synthesis of secondary amines over Ag/Al2O3 catalyst by one-pot reductive amination of aldehydes with nitroarenes

被引:14
作者
Artiukha, Ekaterina A. [1 ]
Nuzhdin, Alexey L. [1 ]
Bukhtiyarova, Galina A. [1 ]
Bukhtiyarov, Valerii I. [1 ,2 ]
机构
[1] Boreskov Inst Catalysis SB RAS, Novosibirsk 630090, Russia
[2] Novosibirsk State Univ, Novosibirsk 630090, Russia
关键词
LIQUID-PHASE HYDROGENATION; CARBONYL-COMPOUNDS; NITRO-COMPOUNDS; AU/AL2O3; CATALYST; RECOVERABLE CATALYST; HIGHLY EFFICIENT; COBALT CATALYST; MILD CONDITIONS; NANOPARTICLES; MONOALKYLATION;
D O I
10.1039/c7ra08986d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An alumina-supported silver catalyst was investigated in the one-pot reductive amination of aldehydes with nitroarenes in a continuous flow reactor using molecular hydrogen as a reducing agent. A series of secondary amines containing alkyl, OH, OCH3, Cl, Br and C=C groups was synthesized in good to excellent yields. The yield of the secondary amine depends on the rate of formation of an intermediate imine. It was shown that the accumulation of carbonaceous deposits on the catalyst is the main reason of catalyst deactivation. The spent catalyst can be easily regenerated and reused without losing catalytic activity.
引用
收藏
页码:45856 / 45861
页数:6
相关论文
共 38 条
[1]   Using Continuous Processes to Increase Production [J].
Anderson, Neal G. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (05) :852-869
[2]   Organically Doped Silver Nanoparticles Deposited on Titania Nanofibers: Enhanced Catalytic Methanol Oxidation [J].
Aouat, Y. ;
Marom, G. ;
Avnir, D. ;
Gelman, V. ;
Shter, G. E. ;
Grader, G. S. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2013, 117 (43) :22325-22330
[3]   One-pot reductive amination of aldehydes with nitroarenes over an Au/Al2O3 catalyst in a continuous flow reactor [J].
Artiukha, E. A. ;
Nuzhdin, A. L. ;
Bukhtiyarova, G. A. ;
Zaytsev, S. Yu. ;
Plyusnin, P. E. ;
Shubin, Yu. V. ;
Bukhtiyarov, V. I. .
CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (10) :4741-4745
[4]   Flow chemistry approaches directed at improving chemical synthesis [J].
Baxendale, Ian R. ;
Brocken, Laurens ;
Mallia, Carl J. .
GREEN PROCESSING AND SYNTHESIS, 2013, 2 (03) :211-230
[5]   MOFs as Multifunctional Catalysts: Synthesis of Secondary Arylamines, Quinolines, Pyrroles, and Arylpyrrolidines over Bifunctional MIL-101 [J].
Cirujano, Francisco G. ;
Leyva-Perez, Antonio ;
Corma, Avelino ;
Llabres i Xamena, Francesc X. .
CHEMCATCHEM, 2013, 5 (02) :538-549
[6]   Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals [J].
Climent, Maria J. ;
Corma, Avelino ;
Iborra, Sara .
CHEMICAL REVIEWS, 2011, 111 (02) :1072-1133
[7]   Cobalt nanoparticles supported on N-doped mesoporous carbon as a highly efficient catalyst for the synthesis of aromatic amines [J].
Cui, Xueliang ;
Liang, Kun ;
Tian, Meng ;
Zhu, Yangyang ;
Ma, Jiantai ;
Dong, Zhengping .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2017, 501 :231-240
[8]   One-pot synthesis of aniline derivatives from nitroarenes under mild conditions promoted by a recyclable polymer-supported palladium catalyst [J].
Dell'Anna, Maria Michela ;
Mastrorilli, Piero ;
Rizzuti, Antonino ;
Leonelli, Cristina .
APPLIED CATALYSIS A-GENERAL, 2011, 401 (1-2) :134-140
[9]   Ultrathin Platinum Nanowire Catalysts for Direct C-N Coupling of Carbonyls with Aromatic Nitro Compounds under 1 Bar of Hydrogen [J].
Hu, Lei ;
Cao, Xueqin ;
Ge, Danhua ;
Hong, Haiyan ;
Guo, Zhiqiang ;
Chen, Liang ;
Sun, Xuhui ;
Tang, Jianxin ;
Zheng, Junwei ;
Lu, Jianmei ;
Gu, Hongwei .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (50) :14283-14287
[10]   Heterogeneous Catalytic Hydrogenation Reactions in Continuous-Flow Reactors [J].
Irfan, Muhammad ;
Glasnov, Toma N. ;
Kappe, C. Oliver .
CHEMSUSCHEM, 2011, 4 (03) :300-316