Catalytic reductive amination of furfural to furfurylamine on robust ultra-small Ni nanoparticles

被引:26
作者
Yang, Yinze [1 ,2 ,3 ]
Zhou, Leilei [1 ,2 ,3 ]
Wang, Xinchao [1 ,2 ,3 ]
Zhang, Liyan [1 ,2 ,3 ]
Cheng, Haiyang [1 ,3 ]
Zhao, Fengyu [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, Changchun Inst Appl Chem, State Key Lab Electroanalyt Chem, Changchun 130022, Peoples R China
[2] Univ Sci & Technol China, Sch Appl Chem & Engn, Hefei 230026, Peoples R China
[3] Chinese Acad Sci, Changchun Inst Appl Chem, Jilin Prov Key Lab Green Chem & Proc, Changchun 130022, Peoples R China
基金
中国国家自然科学基金;
关键词
Ni nanoparticle; reductive amination; furfural; furfurylamine; HIGH-PERFORMANCE CATALYST; PRIMARY AMINES; AQUEOUS AMMONIA; RUTHENIUM NANOPARTICLES; COBALT NANOPARTICLES; SELECTIVE SYNTHESIS; CARBONYL-COMPOUNDS; GENERAL-SYNTHESIS; CO HYDROGENATION; NITRILES;
D O I
10.1007/s12274-022-4923-0
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
The synthesis of primary amines via reductive amination in the presence of NH3 and H-2, as a green and sustainable process, has attracted much attention. In this paper, we prepared series of Ni/SiO2 catalysts with deposition-precipitation and impregnation methods, and their catalytic performances on the reductive amination of a biomass derived compound of furfural to produce furfurylamine were studied. The catalytic activity and the yield were correlated to the structure and the surface properties of catalysts largely. The Ni/SiO2 is of high Lewis acidity and small Ni particle with numerous large Ni flat step surface showed high activity and selectivity, it afforded a reaction rate of 12.8 h(-1) and a high yield to furfurylamine around 98%. These results are superior to the most non-noble metal catalysts reported so far. Moreover, the reaction route was examined with the unit control reactions of the intermediate. To produce furfurylamine selectively, the most suitable catalyst should have the moderate but not the highest activity in activation of hydrogen and hydrogenation in the reductive amination of furfural. This work provides some useful information for the catalytic reductive amination of aldehydes both in the design of catalyst and the reaction route.
引用
收藏
页码:3719 / 3729
页数:11
相关论文
共 75 条
[1]   Reductive Amination in the Synthesis of Pharmaceuticals [J].
Afanasyev, Oleg, I ;
Kuchuk, Ekaterina ;
Usanov, Dmitry L. ;
Chusov, Denis .
CHEMICAL REVIEWS, 2019, 119 (23) :11857-11911
[2]   CO hydrogenation on a nickel catalyst - II. A mechanistic study by transient kinetics and infrared spectroscopy [J].
Agnelli, M ;
Swaan, HM ;
Marquez-Alvarez, C ;
Martin, GA ;
Mirodatos, C .
JOURNAL OF CATALYSIS, 1998, 175 (01) :117-128
[3]   Tuning CO2 Hydrogenation Selectivity by N-Doped Carbon Coating over Nickel Nanoparticles Supported on SiO2 [J].
Arpini, Bruno H. ;
Braga, Adriano H. ;
Borges, Lais R. ;
Vidinha, Pedro ;
Goncalves, Renato, V ;
Szanyi, Janos ;
Rossi, Liane M. .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2022, 10 (07) :2331-2342
[4]   Synergistic Effects of Earth-Abundant Metal-Metal Oxide Enable Reductive Amination of Carbonyls at 50 °C [J].
Bhunia, Manas K. ;
Chandra, Debraj ;
Abe, Hitoshi ;
Niwa, Yasuhiro ;
Hara, Michikazu .
ACS APPLIED MATERIALS & INTERFACES, 2022, 14 (03) :4144-4154
[5]   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
[6]   Reductive Amination, Hydrogenation and Hydrodeoxygenation of 5-Hydroxymethylfurfural using Silica-supported Cobalt- Nanoparticles [J].
Chandrashekhar, Vishwas G. ;
Natte, Kishore ;
Alenad, Asma M. ;
Alshammari, Ahmad S. ;
Kreyenschulte, Carsten ;
Jagadeesh, Rajenahally V. .
CHEMCATCHEM, 2022, 14 (01)
[7]   Photocatalytic Reduction of Aromatic Nitro Compounds with Ag/AgxS Composites under Visible Light Irradiation [J].
Chang, Pingjing ;
Cheng, Haiyang ;
Zhao, Fengyu .
JOURNAL OF PHYSICAL CHEMISTRY C, 2021, 125 (47) :26021-26030
[8]   Preparation of 5-(Aminomethyl)-2-furanmethanol by direct reductive amination of 5-Hydroxymethylfurfural with aqueous ammonia over the Ni/SBA-15 catalyst [J].
Chen, Wei ;
Sun, Yong ;
Du, Juan ;
Si, Zhihao ;
Tang, Xing ;
Zeng, Xianhai ;
Lin, Lu ;
Liu, Shijie ;
Lei, Tingzhou .
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2018, 93 (10) :3028-3034
[9]   Silicon-nickel intermetallic compounds supported on silica as a highly efficient catalyst for CO methanation [J].
Chen, Xiao ;
Jin, Jianhui ;
Sha, Guangyan ;
Li, Chuang ;
Zhang, Bingsen ;
Su, Dangsheng ;
Williams, Christopher T. ;
Liang, Changhai .
CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (01) :53-61
[10]   Platinum-Catalyzed Direct Amination of Allylic Alcohols with Aqueous Ammonia: Selective Synthesis of Primary Allylamines [J].
Das, Kalpataru ;
Shibuya, Ryozo ;
Nakahara, Yasuhito ;
Germain, Nicolas ;
Ohshima, Takashi ;
Mashima, Kazushi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) :150-154