Citation: Zhang Ting-Ting, Jiang Jing-Yang, Wang Yan-Hua. Supported bimetallic catalyst Pt-Pb/SiO₂ for selective conversion of nitrobenzene to p-aminophenol in pressurized CO₂/H₂O system[J]. Chinese Chemical Letters, ;2017, 28(2): 307-311. doi: 10.1016/j.cclet.2016.07.029 shu

Supported bimetallic catalyst Pt-Pb/SiO₂ for selective conversion of nitrobenzene to p-aminophenol in pressurized CO₂/H₂O system

State Key Laboratory of Fine Chemicals, Faculty of Chemical, Environmental and Biological Science and Technology, Dalian University of Technology, Dalian 116024, China

Corresponding author: Jiang Jing-Yang, jyjiang@dlut.edu.cn
Received Date: 12 June 2016
Revised Date: 13 July 2016
Accepted Date: 16 July 2016
Available Online: 29 February 2016

Figures(7)

Various supported Pt-Pb bimetallic catalysts were prepared and applied for the catalytic conversion of nitrobenzene to p-aminophenol in the environmentally benign pressurized CO₂/H₂O system. Among the bimetallic catalysts prepared, Pt-Pb/SiO₂ is the best and nitrobenzene could be converted to paminophenol with a selectivity as high as 82% when the reaction was carried out using this catalyst at 110℃ under 5 MPa CO₂ and 0.2 MPa H₂.
- Nitrobenzene,
- p-Aminophenol,
- Pt-Pb bimetallic catalysts,
- CO₂/H₂O system,
- Environmentally benign
1. [1]
  M.S. Kirk-Othmer, Encyclopedia of Chemical Technology, 4th edn., Wiley, New York, 1992.
2. [2]
  E. Bamberger. Ueber das phenylhydroxylamin[J]. Ber. Dtsch. Chem. Ges., 1894,27:1548-1557. doi: 10.1002/(ISSN)1099-0682
3. [3]
  D.C. Caskey, D.W. Chapman, Process for preparing p-aminophenol and alkyl substituted p-aminophenol, US 4571437.
4. [4]
  S.F. Wang, Y.H. Ma, Y.J. Wang, W. Xue, X.Q. Zhao. Synthesis of p-aminophenol from the hydrogenation of nitrobenzene over metal-solid acid bifunctional catalyst[J]. J. Chem. Tech. Biotechnol., 2008,83:1466-1471. doi: 10.1002/jctb.v83:11
5. [5]
  T. Komatsu, T. Hirose. Gas phase synthesis of para-aminophenol from nitrobenzene on Pt/zeolite catalysts[J]. Appl. Catal. A:Gen., 2004,276:95-102. doi: 10.1016/j.apcata.2004.07.044
6. [6]
  S.F. Wang, B.B. He, Y.J. Wang, X.Q. Zhao. MgAPO-5-supported Pt-Pb-based novel catalyst for the hydrogenation of nitrobenzene to p-aminophenol[J]. Catal. Commun., 2012,24:109-113. doi: 10.1016/j.catcom.2012.03.024
7. [7]
  T.T. Zhang, J.Y. Jiang, Y.H. Wang. Green route for the preparation of p-aminophenol from nitrobenzene by catalytic hydrogenation in pressurized CO₂/H₂O system[J]. Org. Process Res. Dev., 2015,19:2050-2054. doi: 10.1021/acs.oprd.5b00307
8. [8]
  G. Gao, Y. Tao, J.Y. Jiang. Environmentally benign and selective reduction of nitroarenes with Fe in pressurized CO₂-H₂O medium[J]. Green Chem., 2008,10:439-441. doi: 10.1039/b719259b
9. [9]
  S.J. Liu, Y.H. Wang, J.Y. Jiang, Z.L. Jin. The selective reduction of nitroarenes to Narylhydroxylamines using Zn in a CO₂/H₂O system[J]. Green Chem., 2009,11:1397-1400. doi: 10.1039/b906283a
10. [10]
  C.O. Henke, J.V. Vaughen, Reduction of aryl nitro compounds, US 2198249.
11. [11]
  L. Shi, X. Zhou, Industrial synthesis method of p-aminophenol, CN 1087623.
12. [12]
  L.Y. Zou, Y.Y. Cui, W.L. Dai. Highly efficient Au/TiO₂ catalyst for one-pot conversion of nitrobenzene to p-aminophenol in water media[J]. Chin. J. Chem., 2014,32:257-262. doi: 10.1002/cjoc.v32.3
13. [13]
  C.V. Rode, M.J. Vaidya, R.V. Chaudhari, Single step hydrogenation of nitrobenzene to p-aminophenol, US 6403833.
14. [14]
  Z. Dong, T. Wang, J. Zhao. Ni-silicides nanoparticles as substitute for noble metals for hydrogenation of nitrobenzene to p-aminophenol in sulfuric acid[J]. Appl. Catal. A:Gen., 2016,520:151-156. doi: 10.1016/j.apcata.2016.04.013
15. [15]
  C.V. Rode, M.J. Vaidya, R.V. Chaudhari. Synthesis of p-aminophenol by catalytic hydrogenation of nitrobenzene[J]. Org. Process Res. Dev., 1999,3:465-470. doi: 10.1021/op990040r
16. [16]
  S.K. Tanielyan, J.J. Nair, N. Marin. Hydrogenation of nitrobenzene to 4-aminophenol over supported platinum catalysts[J]. Org. Process Res. Dev., 2007,11:681-688. doi: 10.1021/op700049p
17. [17]
  K.I. Min, J.S. Choi, Y.M. Chung. p-Aminophenol synthesis in an organic/aqueous system using Pt supported on mesoporous carbons[J]. Appl. Catal. A:Gen., 2008,337:97-104. doi: 10.1016/j.apcata.2007.12.004
18. [18]
  P.L. Liu, Y.H. Hu, M. Ni, K.Y. You, H.N. Luo. Liquid phase hydrogenation of nitrobenzene to para-aminophenol over Pt/ZrO₂ catalyst and SO₄^2-/ZrO₂-Al₂O₃ solid acid[J]. Catal. Lett., 2010,140:65-68. doi: 10.1007/s10562-010-0427-8
19. [19]
  A. Deshpande, F. Figueras, M.L. Kantam. Environmentally friendly hydrogenation of nitrobenzene to p-aminophenol using heterogeneous catalysts[J]. J. Catal., 2010,275:250-256. doi: 10.1016/j.jcat.2010.08.005
20. [20]
  P.N. Rylander, I.M. Karpenko, G.R. Pond, Process for preparing para-aminophenol, US 3715397.
21. [21]
  E.L. Derrenbacker, Process for the selective preparation of p-aminophenol from nitrobenzene, US 4307249.
22. [22]
  X.B. Shan, Y. Liu, Preparation of p-aminophenol from catalytic hydrogenation of nitrobenzene, CN 85103667.
23. [23]
  H. Lindlar, R. Dubuis, Palladium catalyst for partial reduction of acetylenes, in:Organic Syntheses, John Wiley & Sons, Inc., New York, 2003, p. 89.
24. [24]
  H. Lindlar. Ein neuer katalysator für selektive hydrierungen[J]. Helv. Chim. Acta, 1952,35:446-450. doi: 10.1002/hlca.19520350205
25. [25]
  Y.S. Hwang, Y.S. Kang, B.C. Koo, et al., Method for selective hydrogenation acetylene alcohols, KR 2001082987.
26. [26]
  T.L. Ho, S.H. Liu. Semihydrogenaticn of triple bonds in 1-alkene solutions[J]. Synth. Commun., 1987,17:969-973. doi: 10.1080/00397918708063955
27. [27]
  J.C. Serrano-Ruiz, G.W. Huber, M.A. Sánchez-Castillo. Effect of Sn addition to Pt/CeO₂-Al₂O₃ and Pt/Al₂O₃ catalysts:an XPS, ¹¹⁹Sn Mössbauer and microcalorimetry study[J]. J. Catal., 2006,241:378-388. doi: 10.1016/j.jcat.2006.05.005
28. [28]
  M.Y. Yin, S.B. He, Z.K. Yu. Effect of alumina support on catalytic performance of Pt-Sn/Al₂O₃ catalysts in one-step synthesis of N-phenylbenzylamine from aniline and benzyl alcohol[J]. Chin. J. Catal., 2013,34:1534-1542. doi: 10.1016/S1872-2067(12)60608-1
29. [29]
  G.D. Angel, G. Torres, V. Bertin. The role of lanthanum oxide in the formation of NO₂ over Pt-Pb/Al₂O₃-La₂O₃ catalysts under lean-burn conditions[J]. Catal. Commun., 2006,7:232-235. doi: 10.1016/j.catcom.2005.10.012
30. [30]
  S.A. Bocanegra, O.A. Scelza, S.R. de Miguel. Behavior of PtPb/MgAl₂O₄ catalysts with different Pb contents and trimetallic PtPbIn catalysts in n-butane dehydrogenation[J]. Appl. Catal. A:Gen., 2013,468:135-142. doi: 10.1016/j.apcata.2013.07.051
31. [31]
  Y.Y. Huang, J.D. Cai, M.Y. Liu, Y.L. Guo. Fabrication of a novel PtPbBi/C catalyst for ethanol electro-oxidation in alkaline medium[J]. Electrochim. Acta, 2012,83:1-6. doi: 10.1016/j.electacta.2012.07.089
32. [32]
  G.Q. Sun, Synthesis of p-Aminophenol by Catalytic Hydrogenation, Qingdao University of Science & Technology, Qingdao, 2008.
1. [1]
  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
2. [2]
  Yubang Li , Xixi Hu , Daiqian Xie . The microscopic formation mechanism of O + H2 products from photodissociation of H2O. Chinese Journal of Structural Chemistry, 2024, 43(5): 100274-100274. doi: 10.1016/j.cjsc.2024.100274
3. [3]
  Yu-Hang Li , Shuai Gao , Lu Zhang , Hanchun Chen , Chong-Chen Wang , Haodong Ji . Insights on selective Pb adsorption via O 2p orbit in UiO-66 containing rich-zirconium vacancies. Chinese Chemical Letters, 2024, 35(8): 109894-. doi: 10.1016/j.cclet.2024.109894
4. [4]
  Muhammad Humayun , Mohamed Bououdina , Abbas Khan , Sajjad Ali , Chundong Wang . Designing single atom catalysts for exceptional electrochemical CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(1): 100193-100193. doi: 10.1016/j.cjsc.2023.100193
5. [5]
  Haoyu Luo , Jinsong Chen , Mengfei Luo , Hui Ma , Shengyan Pu . Heterogeneous Fenton catalytic degradation of nitrobenzene by controlled-release nano calcium peroxide. Chinese Chemical Letters, 2025, 36(6): 110367-. doi: 10.1016/j.cclet.2024.110367
6. [6]
  Fanxin Kong , Hongzhi Wang , Huimei Duan . Inhibition effect of sulfation on Pt/TiO2 catalysts in methane combustion. Chinese Journal of Structural Chemistry, 2024, 43(5): 100287-100287. doi: 10.1016/j.cjsc.2024.100287
7. [7]
  Weiping Guo , Ying Zhu , Hong-Hua Cui , Lingyun Li , Yan Yu , Zhong-Zhen Luo , Zhigang Zou . β-Pb₃P₂S₈: A new optical crystal with exceptional birefringence effect. Chinese Chemical Letters, 2025, 36(2): 110256-. doi: 10.1016/j.cclet.2024.110256
8. [8]
  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
9. [9]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
10. [10]
  Xueyang Zhao , Bangwei Deng , Hongtao Xie , Yizhao Li , Qingqing Ye , Fan Dong . Recent process in developing advanced heterogeneous diatomic-site metal catalysts for electrochemical CO₂ reduction. Chinese Chemical Letters, 2024, 35(7): 109139-. doi: 10.1016/j.cclet.2023.109139
11. [11]
  Li Li , Fanpeng Chen , Bohang Zhao , Yifu Yu . Understanding of the structural evolution of catalysts and identification of active species during CO₂ conversion. Chinese Chemical Letters, 2024, 35(4): 109240-. doi: 10.1016/j.cclet.2023.109240
12. [12]
  Jinglin CHENG , Xiaoming GUO , Tao MENG , Xu HU , Liang LI , Yanzhe WANG , Wenzhu HUANG . NiAlNd catalysts for CO₂ methanation derived from the layered double hydroxide precursor. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1592-1602. doi: 10.11862/CJIC.20240152
13. [13]
  Tinghui Yang , Min Kuang , Jianping Yang . Mesoporous CuCe dual-metal catalysts for efficient electrochemical reduction of CO2 to methane. Chinese Journal of Structural Chemistry, 2024, 43(8): 100350-100350. doi: 10.1016/j.cjsc.2024.100350
14. [14]
  Yuxiang Zhang , Jia Zhao , Sen Lin . Nitrogen doping retrofits the coordination environment of copper single-atom catalysts for deep CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100415-100415. doi: 10.1016/j.cjsc.2024.100415
15. [15]
  Xiangyu Chen , Aihao Xu , Dong Wei , Fang Huang , Junjie Ma , Huibing He , Jing Xu . Atomic cerium-doped CuO_x catalysts for efficient electrocatalytic CO₂ reduction to CH₄. Chinese Chemical Letters, 2025, 36(1): 110175-. doi: 10.1016/j.cclet.2024.110175
16. [16]
  Hanhan Chen , Yahao Sun , Mingyang Zhang , Pengtao Ma , Jingping Wang , Jingyang Niu . Self-assembly of cis-trans Ta/W mixed-addendum POMs based on hexalacunary [H₂P₂W₁₂O₄₈]¹²⁻ building blocks. Chinese Chemical Letters, 2025, 36(9): 110329-. doi: 10.1016/j.cclet.2024.110329
17. [17]
  Tianyao He , Gan Li , Xiaoqiang Xie , Dong Han , Yunyue Leng , Qiuli Zhang , Wenming Liu , Guobo Li , Hongxiang Zhang , Shan Huang , Ting Huang , Honggen Peng . Design of highly active meso-zeolite enveloping Pt–Ni bimetallic catalysts for degradation of toluene. Chinese Chemical Letters, 2025, 36(4): 110137-. doi: 10.1016/j.cclet.2024.110137
18. [18]
  Zhijie Zhang , Xun Li , Huiling Tang , Junhao Wu , Chunxia Yao , Kui Li . Cs₂CuBr₄ perovskite quantum dots confined in mesoporous CuO framework as a p-n type S-scheme heterojunction for efficient CO₂ photoconversion. Chinese Chemical Letters, 2024, 35(11): 109700-. doi: 10.1016/j.cclet.2024.109700
19. [19]
  Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H₂O₂ system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
20. [20]
  Xinyu Yin , Haiyang Shi , Yu Wang , Xuefei Wang , Ping Wang , Huogen Yu . Spontaneously Improved Adsorption of H₂O and Its Intermediates on Electron-Deficient Mn^(3+δ)+ for Efficient Photocatalytic H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312007-0. doi: 10.3866/PKU.WHXB202312007

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1285)
HTML views(87)

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

Supported bimetallic catalyst Pt-Pb/SiO2 for selective conversion of nitrobenzene to p-aminophenol in pressurized CO2/H2O system

Metrics

通讯作者: 陈斌, bchen63@163.com

Supported bimetallic catalyst Pt-Pb/SiO₂ for selective conversion of nitrobenzene to p-aminophenol in pressurized CO₂/H₂O system