Citation: Pengyu Wu, Chun Cai. Supported Pt-Ni bimetallic nanoparticles catalyzed hydrodeoxygenation of dibenzofuran with high selectivity to bicyclohexane[J]. Chinese Chemical Letters, ;2022, 33(1): 234-238. doi: 10.1016/j.cclet.2021.05.059 shu

Supported Pt-Ni bimetallic nanoparticles catalyzed hydrodeoxygenation of dibenzofuran with high selectivity to bicyclohexane

Pengyu Wu ,
Chun Cai ^*,

Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, China

c.cai@njust.edu.cn

Received Date: 25 March 2021
Revised Date: 25 May 2021
Accepted Date: 26 May 2021
Available Online: 31 May 2021

Figures(6)

Catalytic hydrodeoxygenation (HDO) is one of the most effective methods to upgrade the oxygen-containing compounds derived from coal tar to valuable hydrocarbons. Herein, an efficient bimetallic catalyst Pt₁Ni₄/MgO was prepared and applied in the HDO of dibenzofuran (DBF). High yield (95%) of the desired product bicyclohexane (BCH) was achieved at 240 ℃ and 1.2 MPa of H₂. Superior catalytic performance could be ascribed to the "relay catalysis" of Pt sites and Ni sites, and the reaction pathway is proposed as well. Scale-up experiment and recyclability test were also performed, which demonstrated the recyclability and promising potential application of Pt₁Ni₄/MgO.
- Hydrodeoxygenation,
- Dibenzofuran,
- Bicyclohexane,
- Bimetallic catalyst,
- Relay catalysis
1. [1]
  P. Blum, A. Sagner, A. Tiehm, et al., J. Contam. Hydrol. 126(2011) 181-194. doi: 10.1016/j.jconhyd.2011.08.004
2. [2]
  J. Lu, A. Heyden, J. Catal. 321(2015) 39-50. doi: 10.1016/j.jcat.2014.11.003
3. [3]
  H. Wang, J. Male, Y. Wang, ACS Catal. 3(2013) 1047-1070. doi: 10.1021/cs400069z
4. [4]
  S. Kim, E.E. Kwon, Y.T. Kim, et al., Green Chem. 21(2019) 3715-3743. doi: 10.1039/C9GC01210A
5. [5]
  D. Leckel, Energ. Fuel. 20(2006) 1761-1766. doi: 10.1021/ef060034d
6. [6]
  S. Yang, X. Lu, H. Yao, et al., Green Chem. 21(2019) 597-605. doi: 10.1039/C8GC03775B
7. [7]
  C.M. Huelsman, P.E. Savage, Phys. Chem. Chem. Phys. 14(2012) 2900-2910. doi: 10.1039/c2cp23910h
8. [8]
  S. Krishnamurthy, S. Panvelker, Y.T. Shah, AlChE J 27(1981) 994-1001. doi: 10.1002/aic.690270616
9. [9]
  V. LaVopa, C.N. Satterfield, Energ. Fuel. 1(1987) 323-331. doi: 10.1021/ef00004a003
10. [10]
  T. Mochizuki, S.Y. Chen, M. Toba, Y. Yoshimura, Appl. Catal. B: Environ. 146(2014) 237-243. doi: 10.1016/j.apcatb.2013.05.040
11. [11]
  S. Boullosa-Eiras, R. Lødeng, H. Bergem, et al., Catal. Today 223(2014) 44-53. doi: 10.1016/j.cattod.2013.09.044
12. [12]
  S. Liu, H. Wang, C.S. Kim, K.J. Smith, Appl. Catal. A: Gen. 600(2020) 117628. doi: 10.1016/j.apcata.2020.117628
13. [13]
  P.M. de Souza, R.C. Rabelo-Neto, L.E.P. Borges, et al., ACS Catal. 5(2015) 1318-1329. doi: 10.1021/cs501853t
14. [14]
  J. Wildschut, F.H. Mahfud, R.H. Venderbosch, H.J. Heeres, Ind. Eng. Chem. Res. 48(2009) 10324-10334. doi: 10.1021/ie9006003
15. [15]
  D.A. Ruddy, J.A. Schaidle, J.R. Ferrell Iii, et al., Green Chem. 16(2014) 454-490. doi: 10.1039/C3GC41354C
16. [16]
  L. Wang, M. Zhang, M. Zhang, G. Sha, C. Liang, Energ. Fuel. 27(2013) 2209-2217. doi: 10.1021/ef302166q
17. [17]
  L. Wang, C. Li, S. Jin, W. Li, C. Liang, Catal. Lett. 144(2014) 809-816. doi: 10.1007/s10562-014-1236-2
18. [18]
  Y. Wu, S. Cai, D. Wang, W. He, Y. Li, J. Am. Chem. Soc. 134(2012) 8975-8981. doi: 10.1021/ja302606d
19. [19]
  M. Sankar, N. Dimitratos, P.J. Miedziak, et al., Chem. Soc. Rev. 41(2012) 8099-8139. doi: 10.1039/c2cs35296f
20. [20]
  D. Ballesteros-Plata, A. Infantes-Molina, M. Rodríguez-Cuadrado, et al., Appl. Catal. A: Gen. 547(2017) 86-95. doi: 10.1016/j.apcata.2017.08.034
21. [21]
  X.B. Wang, Z.Z. Xie, L. Guo, Z.Y. Du, W.Y. Li, Catal. Today 364(2021) 220-228. doi: 10.1016/j.cattod.2020.04.044
22. [22]
  S. Jin, Z. Xiao, X. Chen, et al., Ind. Eng. Chem. Res. 54(2015) 2302-2310. doi: 10.1021/ie504600f
23. [23]
  V. Molinari, G. Clavel, M. Graglia, M. Antonietti, D. Esposito, ACS Catal. 6(2016) 1663-1670. doi: 10.1021/acscatal.5b01926
24. [24]
  A.G. Sergeev, J.D. Webb, J.F. Hartwig, J. Am. Chem. Soc. 134(2012) 20226-20229. doi: 10.1021/ja3085912
25. [25]
  J.W. Zhang, G.P. Lu, C. Cai, Green Chem. 19(2017) 4538-4543. doi: 10.1039/C7GC02087B
26. [26]
  J.W. Zhang, K.K. Sun, D.D. Li, et al., Appl. Catal. A: Gen. 569(2019) 190-195. doi: 10.1016/j.apcata.2018.10.038
27. [27]
  J.A. Cecilia, A. Infantes-Molina, E. Rodríguez-Castellón, A. Jiménez-López, S.T. Oyama, Appl. Catal. B: Environ. 136-137(2013) 140-149.
28. [28]
  M. Guo, J. Peng, Q. Yang, C. Li, ACS Catal. 8(2018) 11174-11183. doi: 10.1021/acscatal.8b03253
29. [29]
  M. Li, Z. Zhao, T. Cheng, et al., Science 354(2016) 1414-1419. doi: 10.1126/science.aaf9050
30. [30]
  B. Wang, L. Xiong, H. Hao, et al., J. Alloys Compd. 844(2020) 156253. doi: 10.1016/j.jallcom.2020.156253
1. [1]
  Bin Chen , Chaoyang Zheng , Dehuan Shi , Yi Huang , Renxia Deng , Yang Wei , Zheyuan Liu , Yan Yu , Shenghong Zhong . p-d orbital hybridization induced by CuGa2 promotes selective N2 electroreduction. Chinese Journal of Structural Chemistry, 2025, 44(1): 100468-100468. doi: 10.1016/j.cjsc.2024.100468
2. [2]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
3. [3]
  Yaoyin Lou , Xiaoyang Jerry Huang , Kuang-Min Zhao , Mark J. Douthwaite , Tingting Fan , Fa Lu , Ouardia Akdim , Na Tian , Shigang Sun , Graham J. Hutchings . Stable core-shell Janus BiAg bimetallic catalyst for CO₂ electrolysis into formate. Chinese Chemical Letters, 2025, 36(3): 110300-. doi: 10.1016/j.cclet.2024.110300
4. [4]
  Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO₂ catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
5. [5]
  Yuhan Liu , Jingyang Zhang , Gongming Yang , Jian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790
6. [6]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
7. [7]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
8. [8]
  Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
9. [9]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
10. [10]
  Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
11. [11]
  Jun LI , Huipeng LI , Hua ZHAO , Qinlong LIU . Preparation and photocatalytic performance of AgNi bimetallic modified polyhedral bismuth vanadate. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 601-612. doi: 10.11862/CJIC.20230401
12. [12]
  Hong Yin , Zhipeng Yu . Hexavalent iridium catalyst enhances efficiency of hydrogen production. Chinese Journal of Structural Chemistry, 2025, 44(1): 100382-100382. doi: 10.1016/j.cjsc.2024.100382
13. [13]
  Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372
14. [14]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
15. [15]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
16. [16]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
17. [17]
  Wen LUO , Lin JIN , Palanisamy Kannan , Jinle HOU , Peng HUO , Jinzhong YAO , Peng WANG . Preparation of high-performance supercapacitor based on bimetallic high nuclearity titanium-oxo-cluster based electrodes. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 782-790. doi: 10.11862/CJIC.20230418
18. [18]
  Yufei Jia , Fei Li , Ke Fan . Surface reconstruction of Cu-based bimetallic catalysts for electrochemical CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100255-100255. doi: 10.1016/j.cjsc.2024.100255
19. [19]
  Tao Wei , Jiahao Lu , Pan Zhang , Qi Zhang , Guang Yang , Ruizhi Yang , Daifen Chen , Qian Wang , Yongfu Tang . An intermittent lithium deposition model based on bimetallic MOFs derivatives for dendrite-free lithium anode with ultrahigh areal capacity. Chinese Chemical Letters, 2024, 35(8): 109122-. doi: 10.1016/j.cclet.2023.109122
20. [20]
  Ji Chen , Yifan Zhao , Shuwen Zhao , Hua Zhang , Youyu Long , Lingfeng Yang , Min Xi , Zitao Ni , Yao Zhou , Anran Chen . Heterogeneous bimetallic oxides/phosphides nanorod with upshifted d band center for efficient overall water splitting. Chinese Chemical Letters, 2024, 35(9): 109268-. doi: 10.1016/j.cclet.2023.109268

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(584)
HTML views(81)

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