Citation: Yanwei Cao, Huan Zheng, Gangli Zhu, Haihong Wu, Lin He. Ceria supported Ru⁰-Ru^δ+ clusters as efficient catalyst for arenes hydrogenation[J]. Chinese Chemical Letters, ;2021, 32(2): 770-774. doi: 10.1016/j.cclet.2020.05.045 shu

Ceria supported Ru⁰-Ru^δ+ clusters as efficient catalyst for arenes hydrogenation

Yanwei Cao ^{a, b} ,
Huan Zheng ^{a, b} ,
Gangli Zhu ^{a, *,} ,
Haihong Wu ^{c, *,} ,
Lin He ^{a, *,}

a.
State Key Laboratory for Oxo Synthesis and Selective Oxidation (OSSO), Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences (CAS), Lanzhou 730000, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
Henan Province Key Laboratory of New Opto-Electronic Functional Materials, College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455000, China

zhugl@licp.cas.cn

sailor99600@126.com

helin@licp.cas.cn

Received Date: 27 April 2020
Revised Date: 15 May 2020
Accepted Date: 30 May 2020
Available Online: 1 June 2020

Figures(3)

Selective hydrogenation of aromatic amines, especially chemicals such as aniline and bis(4-aminocyclohexyl)methane for non-yellowing polyurethane, is of particular interests due to the extensive applications. To conquer the existing difficulties in selective hydrogenation, the Ru⁰-Ru^δ+/CeO₂ catalyst with solid frustrated Lewis pairs was developed for aromatic amines hydrogenation with excellent activity and selectivity under relative milder conditions. The morphology, electronic and chemical properties, especially the Ru⁰-Ru^δ+ clusters and reducible ceria were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), X-ray photoelectron spectroscopy (XPS), CO₂ temperature programmed desorption (CO₂-TPD), H₂ temperature programmed reduction (H₂-TPR), H₂ diffuse reflectance Fourier transform infrared spectroscopy (H₂-DRIFT), Raman, etc. The 2% Ru/CeO₂ catalyst exhibited good conversion of 95% and selectivity greater than 99% toward cyclohexylamine. The volcano curve describing the activity and Ru state was found. Owning to the "acidic site isolation" by surrounding alkaline sites, condensation between the neighboring amine molecules could be effectively suppressed. The catalyst also showed good stability and applicability for other aromatic amines and heteroarenes containing different functional groups.
- Ceria,
- Ruthenium,
- Clusters,
- Amines,
- Hydrogenation
1. [1]
  Z. Wei, Y. Li, J. Wang, et al., Chin. Chem. Lett. 29 (2018) 815-818. doi: 10.1016/j.cclet.2018.01.020
2. [2]
  Z.Q. Liu, X.Y. Wei, F.J. Liu, et al., Fuel 223 (2018) 222-229. doi: 10.1016/j.fuel.2018.03.014
3. [3]
  W. Hayazaki, H. Omori, K. Ozaki, JP2002348267A, 2002.
4. [4]
  G.Y. Fan, W.J. Huang, Chin. Chem. Lett. 25 (2014) 359-363. doi: 10.1016/j.cclet.2013.11.044
5. [5]
  H.Z. Bi, R.F. Dou, H. Wang, et al., Acta Phys.-Chim. Sin. 32 (2016) 1765-1774. doi: 10.3866/PKU.WHXB201604085
6. [6]
  T. Montini, M. Melchionna, M. Monai, et al., Chem. Rev. 116 (2016) 5987-6041. doi: 10.1021/acs.chemrev.5b00603
7. [7]
  S. Zhang, Z.Q. Huang, Y. Ma, et al., Nat. Commun. 8 (2017) 15266. doi: 10.1038/ncomms15266
8. [8]
  M. Garcia-Melchor, N.R. Lo'pez, J. Phys. Chem. C 118 (2014) 10921-10926. doi: 10.1021/jp502309r
9. [9]
  B. Ouyang, W. Tan, B. Liu, Catal. Commun. 95 (2017) 36-39. doi: 10.1016/j.catcom.2017.03.005
10. [10]
  J. An, Y. Wang, J. Lu, et al., J. Am. Chem. Soc. 140 (2018) 4172-4181. doi: 10.1021/jacs.8b01742
11. [11]
  N. Ta, J. Liu, S. Chenna, et al., J. Am. Chem. Soc. 134 (2012) 20585-20588. doi: 10.1021/ja310341j
12. [12]
  A. Figueroba, G. Kovacs, A. Bruix, et al., Catal. Sci. Technol. 6 (2016) 6806-6813. doi: 10.1039/C6CY00294C
13. [13]
  Y. Guo, S. Mei, K. Yuan, et al., ACS Catal. 8 (2018) 6203-6215. doi: 10.1021/acscatal.7b04469
14. [14]
  F. Wang, C.M. Li, X.Y. Zhang, et al., J. Catal. 329 (2015) 177-186. doi: 10.1016/j.jcat.2015.05.014
15. [15]
  Z.A. Qiao, Z. Wu, S. Dai, ChemSusChem 6 (2013) 1821-1833. doi: 10.1002/cssc.201300428
16. [16]
  P.G.J. Koopman, A.P.G. Kieboom, H. Van Bekkum, J. Catal. 69 (1981) 172-179. doi: 10.1016/0021-9517(81)90139-1
17. [17]
  G. Vilé, B. Bridier, J. Wichert, et al., Angew. Chem., Int. Ed. 51 (2012) 8620-8623. doi: 10.1002/anie.201203675
18. [18]
  Z. Mo, Y. Sun, H. Chen, et al., Polymer 46 (2005) 12670-12676. doi: 10.1016/j.polymer.2005.10.117
19. [19]
  F.R. Negreiros, M.F. Camellone, S. Fabris, J. Phys. Chem. C 119 (2015) 21567-21573. doi: 10.1021/acs.jpcc.5b07030
20. [20]
  A. Arico, P. Creti, H. Kim, et al., J. Electrochem. Soc. 143 (1996) 3950-3959. doi: 10.1149/1.1837321
21. [21]
  Z.Q. Huang, L.P. Liu, S. Qi, et al., ACS Catal. 8 (2018) 546-554. doi: 10.1021/acscatal.7b02732
22. [22]
  A.M. Rasero-Almansa, A. Corma, M. Iglesias, et al., Green Chem. 16 (2014) 3522-3527. doi: 10.1039/C4GC00581C
23. [23]
  S. Zhang, M. Zhang, Y. Qu, Acta Phys.-Chim. Sin. 36 (2020) 1911050.
24. [24]
  K. Werner, X. Weng, F. Calaza, et al., J. Am. Chem. Soc. 139 (2017) 17608-17616. doi: 10.1021/jacs.7b10021
25. [25]
  W. Liang, M. Cui, J. Tang, et al., J. Nanjing Tech Univ. (Nat. Sci. Ed. ) 02 (2014) 89-94.
26. [26]
  F. Chen, C. Topf, J. Radnik, et al., J. Am. Chem. Soc. 138 (2016) 8781-8788. doi: 10.1021/jacs.6b03439
1. [1]
  Jun Zhang , Zhiyao Zheng , Can Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160
2. [2]
  Xinyu Hou , Xuelian Yu , Meng Liu , Hengxing Peng , Lijuan Wu , Libing Liao , Guocheng Lv . Ultrafast synthesis of Mo₂N with highly dispersed Ru for efficient alkaline hydrogen evolution. Chinese Chemical Letters, 2025, 36(4): 109845-. doi: 10.1016/j.cclet.2024.109845
3. [3]
  Xinghao Cai , Chen Ma , Ying Kang , Yuqiang Ren , Xue Meng , Wei Lu , Shiming Fan , Shouxin Liu . Nickel-catalyzed C(sp²)–H alkynylation of free α-substituted benzylamines using a transient directing group. Chinese Chemical Letters, 2025, 36(10): 110901-. doi: 10.1016/j.cclet.2025.110901
4. [4]
  Lingyun Shen , Shenxiang Yin , Qingshu Zheng , Zheming Sun , Wei Wang , Tao Tu . A rechargeable and portable hydrogen storage system grounded on soda water. Chinese Chemical Letters, 2025, 36(3): 110580-. doi: 10.1016/j.cclet.2024.110580
5. [5]
  Zunjie Zhang , Mengran Liu , Bingcheng Ge , Tianfang Yang , Shuaitong Wang , Yang Liu , Shuyan Gao . In-situ reconstructed Cu/NiO nanosheets synergistically boosting nitrate electroreduction to ammonia. Chinese Chemical Letters, 2025, 36(8): 110657-. doi: 10.1016/j.cclet.2024.110657
6. [6]
  Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Liu Fei . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-0. doi: 10.3866/PKU.WHXB202408004
7. [7]
  Xin Li , Jia-Min Lu , Bo Li , Chen Zhao , Bei-Bei Yang , Li Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310
8. [8]
  Qi Huang , Jun Liao , Jingjing Li , Zhengyan Gu , Xinkang Zhang , Mingxue Sun , Wenqi Meng , Guanchao Mao , Zhipeng Pei , Shanshan Zhang , Songling Li , Chuan Zhang , Yunqin Wang , Jihao Liu , Tingbin Shu , Min Tao , Ying Lu , Kai Xiao , Qingqiang Xu , Jincai Lu . Curcumin-loaded ceria nanoenzymes for dual-action suppression of inflammation and alleviation of oxidative damage in the treatment of acute lung injury. Chinese Chemical Letters, 2025, 36(4): 109914-. doi: 10.1016/j.cclet.2024.109914
9. [9]
  Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
10. [10]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
11. [11]
  Qiyan Wu , Ruixin Zhou , Zhangyi Yao , Tanyuan Wang , Qing Li . Effective approaches for enhancing the stability of ruthenium-based electrocatalysts towards acidic oxygen evolution reaction. Chinese Chemical Letters, 2024, 35(10): 109416-. doi: 10.1016/j.cclet.2023.109416
12. [12]
  Hao WANG , Kun TANG , Jiangyang SHAO , Kezhi WANG , Yuwu ZHONG . Electro-copolymerized film of ruthenium catalyst and redox mediator for electrocatalytic water oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2193-2202. doi: 10.11862/CJIC.20240176
13. [13]
  Chun-Yun Ding , Ru-Yuan Zhang , Yu-Wu Zhong , Jiannian Yao . Binary and heterostructured microplates of iridium and ruthenium complexes: Preparation, characterization, and thermo-responsive emission. Chinese Journal of Structural Chemistry, 2024, 43(10): 100393-100393. doi: 10.1016/j.cjsc.2024.100393
14. [14]
  Qing Li , Bing Wang , Qi Xu , Ruiyou Liu , Chen Li , Fang Luo , Yifei Li , Yingjie Yu , Zehui Yang . Pt dopants in ruthenium/iridium oxides promote catalytic activity in overall acidic water splitting. Chinese Chemical Letters, 2025, 36(12): 111658-. doi: 10.1016/j.cclet.2025.111658
15. [15]
  Jianhong Jiang , Xianming Xia , Hongbo He . Novel vinylene-linked COF ruthenium catalyst design achieves record performance in proton exchange membrane water electrolyzers. Chinese Journal of Structural Chemistry, 2025, 44(9): 100656-100656. doi: 10.1016/j.cjsc.2025.100656
16. [16]
  Rui HUANG , Shengjie LIU , Qingyuan WU , Nanfeng ZHENG . Enhanced selectivity of catalytic hydrogenation of halogenated nitroaromatics by interfacial effects. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 201-212. doi: 10.11862/CJIC.20240356
17. [17]
  Minghui Zhang , Na Zhang , Qian Zhao , Chao Wang , Alexander Steiner , Jianliang Xiao , Weijun Tang . Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines. Chinese Chemical Letters, 2025, 36(4): 110081-. doi: 10.1016/j.cclet.2024.110081
18. [18]
  Hai-Ling Wang , Zhong-Hong Zhu , Hua-Hong Zou . Structure and assembly mechanism of high-nuclear lanthanide-oxo clusters. Chinese Journal of Structural Chemistry, 2024, 43(9): 100372-100372. doi: 10.1016/j.cjsc.2024.100372
19. [19]
  Xiuhua Wang , Jianrong Steve Zhou . A dicationic nickel complex-catalyzed asymmetric synthesis of chiral benzylic amines: Evolution from reductive amination to borrowing hydrogen reaction. Chinese Chemical Letters, 2026, 37(2): 111148-. doi: 10.1016/j.cclet.2025.111148
20. [20]
  Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(2464)
HTML views(309)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Ceria supported Ru0-Ruδ+ clusters as efficient catalyst for arenes hydrogenation

Metrics

通讯作者: 陈斌, bchen63@163.com

Ceria supported Ru⁰-Ru^δ+ clusters as efficient catalyst for arenes hydrogenation