Efficient and selective approach to biomass-based amine by reductive amination of furfural using Ru catalyst

被引：74
作者：
Zou, Hongtao [1 ]
Chen, Jinzhu [1 ]
机构：
[1] Jinan Univ, Coll Chem & Mat Sci, Guangdong Prov Key Lab Funct Supramol Coordinat M, Guangzhou 511443, Peoples R China
来源：
APPLIED CATALYSIS B-ENVIRONMENTAL | 2022年 / 309卷
基金：
中国国家自然科学基金;
关键词：
Amine; Furfural; Hydrazine; Reductive amination; Ru catalyst; HIGH-PERFORMANCE CATALYST; RUTHENIUM NANOPARTICLES; MOLECULAR-HYDROGEN; GENERAL-SYNTHESIS; CARBON; AMMONIA; BORON; HYDRAZINE;
D O I：
10.1016/j.apcatb.2022.121262
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Reductive amination of furfural (1a) to furfurylamine (2a) was developed as a powerful and practical approach to biomass-based amine. Herein, Ru catalyst (Ru/BNC) supported on boron/nitrogen co-doped carbon (BNC) was reported for the reductive amination with hydrous hydrazine (N2H4 center dot H2O) as a nitrogen source and hydrazone as intermediate. Our mechanism investigation suggested rich Frustrated Lewis acid-base pairs (FLPs) on the BNC surface synergistically enhanced the activity of Ru catalyst. Moreover, quick formation rate of hydrazone intermediate and its moderate reactivity significantly improved 2a selectivity. Under optimal conditions, Ru/BNC catalyst can highly efficiently and selectively promote 1a/N2H4-to-2a transformation with 2a yield exceeding 99%. Moreover, the role of nitrogen sources such as N2H4, NH3 and hydroxylamine on the 2a selectivity was systematically investigated. Additionally, the developed Ru/BNC-N2H4 system was applicable to a wide range of aldehydes to give the desired primary amines in excellent to good yields (85-99%) in the reductive amination reaction.
引用
收藏
页数：14
相关论文
共 60 条
[1]   The platinum catalyzed hydrazine decomposition in non-nitrate acidic media [J].
Ananiev, AV ;
Broudic, JC ;
Brossard, P .
APPLIED CATALYSIS A-GENERAL, 2003, 242 (01) :1-10
[2]   Influence of Bronsted acid sites on chemoselective synthesis of pyrrolidones over H-ZSM-5 supported copper catalyst [J].
Boosa, Venu ;
Varimalla, Shirisha ;
Dumpalapally, Mahesh ;
Gutta, Naresh ;
Velisoju, Vijay Kumar ;
Nama, Narender ;
Akula, Venugopal .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2021, 292
[3]   A high performance catalyst of shape-specific ruthenium nanoparticles for production of primary amines by reductive amination of carbonyl compounds [J].
Chandra, Debraj ;
Inoue, Yasunori ;
Sasase, Masato ;
Kitano, Masaaki ;
Bhaumik, Asim ;
Kamata, Keigo ;
Hosono, Hideo ;
Hara, Michikazu .
CHEMICAL SCIENCE, 2018, 9 (27) :5949-5956
[4]   Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: an environmentally friendly approach [J].
Chatterjee, Maya ;
Ishizaka, Takayuki ;
Kawanami, Hajime .
GREEN CHEMISTRY, 2016, 18 (02) :487-496
[5]   Boron and nitrogen co-doped porous carbon with a high concentration of boron and its superior capacitive behavior [J].
Chen, Hao ;
Xiong, Yachao ;
Yu, Tao ;
Zhu, Pengfei ;
Yan, Xinzhu ;
Wang, Zhao ;
Guan, Shiyou .
CARBON, 2017, 113 :266-273
[6]   Metal-Free H2 Activation for Highly Selective Hydrogenation of Nitroaromatics Using Phosphorus-Doped Carbon Nanotubes [J].
Chen, Xuehua ;
Shen, Qiujuan ;
Li, Zhijing ;
Wan, Weihao ;
Chen, Jinzhu ;
Zhang, Jiayan .
ACS APPLIED MATERIALS & INTERFACES, 2020, 12 (01) :654-666
[7]   Synergistic effect of metal-organic framework-derived boron and nitrogen heteroatom-doped three-dimensional porous carbons for precious-metal-free catalytic reduction of nitroarenes [J].
Chi Van Nguyen ;
Lee, Seulchan ;
Chung, Yongchul G. ;
Chiang, Wei-Hung ;
Wu, Kevin C-W .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2019, 257
[8]   Ab Initio Molecular Dynamics Simulations of the Cooperative Adsorption of Hydrazine and Water on Copper Surfaces: Implications for Shape Control of Nanoparticles [J].
Daff, Thomas D. ;
de Leeuw, Nora H. .
CHEMISTRY OF MATERIALS, 2011, 23 (11) :2718-2728
[9]   Low-Temperature Reductive Amination of Carbonyl Compounds over Ru Deposited on Nb2O5.•nH2O [J].
Deng, Dian ;
Kita, Yusuke ;
Kamata, Keigo ;
Hara, Michikazu .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (05) :4692-4698
[10]   A Heterogeneous Metal-Free Catalyst for Hydrogenation: Lewis Acid-Base Pairs Integrated into a Carbon Lattice [J].
Ding, Yuxiao ;
Huang, Xing ;
Yi, Xianfeng ;
Qiao, Yunxiang ;
Sun, Xiaoyan ;
Zheng, Anmin ;
Su, Dang Sheng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (42) :13800-13804
123456