Regulation of the selective hydrogenation performance of sulfur-doped carbon-supported palladium on chloronitrobenzene

doi:10.1016/j.cjche.2022.11.007

中国化学工程学报 ›› 2023, Vol. 58 ›› Issue (6): 69-75.DOI: 10.1016/j.cjche.2022.11.007

• Full Length Article • 上一篇下一篇

Regulation of the selective hydrogenation performance of sulfur-doped carbon-supported palladium on chloronitrobenzene

Qunfeng Zhang, Bingcheng Li, Yuan Zhou, Deshuo Zhang, Chunshan Lu, Feng Feng, Jinghui Lv, Qingtao Wang, Xiaonian Li

Institute of Industrial Catalysis of Zhejiang University of Technology, State Key Laboratory Breeding Base of Green Chemistry Synthesis Technology, Hangzhou 310014, China

收稿日期:2022-07-16 修回日期:2022-11-15 出版日期:2023-06-28 发布日期:2023-08-31
通讯作者: Qunfeng Zhang,E-mail:zhangqf@zjut.edu.cn;Qingtao Wang,E-mail:qtwang@zjut.edu.cn;Xiaonian Li,E-mail:xnli@zjut.edu.cn
基金资助:
This work was financially supported by the National Natural Science Foundation of China (22078292, 22008212, U20A20119, 21776258).

Regulation of the selective hydrogenation performance of sulfur-doped carbon-supported palladium on chloronitrobenzene

Qunfeng Zhang, Bingcheng Li, Yuan Zhou, Deshuo Zhang, Chunshan Lu, Feng Feng, Jinghui Lv, Qingtao Wang, Xiaonian Li

Institute of Industrial Catalysis of Zhejiang University of Technology, State Key Laboratory Breeding Base of Green Chemistry Synthesis Technology, Hangzhou 310014, China

Received:2022-07-16 Revised:2022-11-15 Online:2023-06-28 Published:2023-08-31
Contact: Qunfeng Zhang,E-mail:zhangqf@zjut.edu.cn;Qingtao Wang,E-mail:qtwang@zjut.edu.cn;Xiaonian Li,E-mail:xnli@zjut.edu.cn
Supported by:
This work was financially supported by the National Natural Science Foundation of China (22078292, 22008212, U20A20119, 21776258).

摘要/Abstract

摘要： The overall performance of metal catalysts can be efficiently adjusted by modifying carbon carriers with different valence sulfur precursors. The wet impregnation technique successfully prepared carbon material carriers doped with varying sources of sulfur (Na₂SO₄, NaHSO₃, Na₂S·9H₂O). Palladium carbon catalysts doped with different sulfur precursors had been prepared with the aid of the liquid-phase reduction method of the selective hydrogenation of o-chloronitrobenzene (o-CNB) to o-chloroaniline (o-CAN). The catalyst prepared for Na₂S·9H₂O as a precursor has excellent performance, and the selectivity for o-CAN is more than 99.9% at 100% conversion. In addition, the characterization results show that with the decrease of S valence, the electronic effect between S and Pd increases, and the outer electron shift of Pd increases, which reduces the adsorption and dissociation ability of Pd to hydrogen, resulting in excellent selectivity. The effects provided a good idea for the hydrogenation of o-CNB and a different point of view on sulfur doping in a variety of hydrogenation reactions.

关键词: Catalyst, Hydrogenation, Selectivity, Sulfur doping, Electronic effect

Abstract: The overall performance of metal catalysts can be efficiently adjusted by modifying carbon carriers with different valence sulfur precursors. The wet impregnation technique successfully prepared carbon material carriers doped with varying sources of sulfur (Na₂SO₄, NaHSO₃, Na₂S·9H₂O). Palladium carbon catalysts doped with different sulfur precursors had been prepared with the aid of the liquid-phase reduction method of the selective hydrogenation of o-chloronitrobenzene (o-CNB) to o-chloroaniline (o-CAN). The catalyst prepared for Na₂S·9H₂O as a precursor has excellent performance, and the selectivity for o-CAN is more than 99.9% at 100% conversion. In addition, the characterization results show that with the decrease of S valence, the electronic effect between S and Pd increases, and the outer electron shift of Pd increases, which reduces the adsorption and dissociation ability of Pd to hydrogen, resulting in excellent selectivity. The effects provided a good idea for the hydrogenation of o-CNB and a different point of view on sulfur doping in a variety of hydrogenation reactions.

Key words: Catalyst, Hydrogenation, Selectivity, Sulfur doping, Electronic effect

Qunfeng Zhang, Bingcheng Li, Yuan Zhou, Deshuo Zhang, Chunshan Lu, Feng Feng, Jinghui Lv, Qingtao Wang, Xiaonian Li. Regulation of the selective hydrogenation performance of sulfur-doped carbon-supported palladium on chloronitrobenzene[J]. 中国化学工程学报, 2023, 58(6): 69-75.

参考文献

[1] H.U. Blaser, H. Steiner, M. Studer, Selective catalytic hydrogenation of functionalized nitroarenes: an update, ChemCatChem 1 (2) (2009) 210-221.
[2] R.G. Xie, X.Q. Cao, Y. Pan, H.W. Gu, Synthesis of Pt nanocatalysts for selective hydrogenation of ortho-halogenated nitrobenzene, Sci. China Chem. 58 (6) (2015) 1051-1055.
[3] J.F. Hartwig, Carbon-heteroatom bond formation catalysed by organometallic complexes, Nature 455 (7211) (2008) 314-322.
[4] B.B. Huang, J. Li, X.K. Cao, Y.Y. Zhu, W.Q. Chen, C. Lei, Electrochemical reduction of p-chloronitrobenzene (p-CNB) at silver cathode in dimethylformamide, Electrochimica Acta 296 (2019) 980-988.
[5] C. Ravichandran, D. Vasudevan, S. Thangavelu, P.N. Anantharaman, Synthesis of chloroanilines at a Ti/ceramic TiO₂-cathode, J Appl Electrochem 22 (11) (1992) 1087-1090.
[6] R.V. Jagadeesh, D. Banerjee, P.B. Arockiam, H. Junge, K. Junge, M.M. Pohl, J. Radnik, A. Brückner, M. Beller, Highly selective transfer hydrogenation of functionalised nitroarenes using cobalt-based nanocatalysts, Green Chem. 17 (2) (2015) 898-902.
[7] Y.K. Zhao, R.R. Tang, R. Huang, Palladium supported on graphitic carbon nitride: an efficient and recyclable heterogeneous catalyst for reduction of nitroarenes and suzuki coupling reaction, Catal Lett 145 (11) (2015) 1961-1971.
[8] X.L. Tian, S.H. Chen, P. Zhang, P. Yang, Y.K. Yi, T. Wang, B.R. Fang, P. Liu, L. Qu, M.T. Li, H.P. Ma, Covalent organic frameworks with immobilized anions to liberate lithium ions: Quasi-solid electrolytes with enhanced rate capabilities, Electrochimica Acta 389 (2021) 138585.
[9] M. Noel, C. Ravichandran, P.N. Anantharaman, An electrochemical technique for the reduction of aromatic nitrocompounds in H₂SO₄ medium on thermally coated Ti/TiO₂ electrodes, J Appl Electrochem 25 (7) (1995) 690-698.
[10] X.Y. Zhao, A.L. Li, X. Quan, S. Chen, H.T. Yu, S.S. Zhang, Efficient electrochemical reduction of nitrobenzene by nitrogen doped porous carbon, Chemosphere 238 (2020) 124636.
[11] S.N. Yue, X.G. Wang, S.T. Li, Y. Sheng, X.J. Zou, X.G. Lu, C.L. Zhang, Highly selective hydrogenation of halogenated nitroarenes over Ru/CN nanocomposites by in situ pyrolysis, New J. Chem. 44 (27) (2020) 11861-11869.
[12] C.S. Lu, M.J. Wang, Z.L. Feng, Y.N. Qi, F. Feng, L. Ma, Q.F. Zhang, X.N. Li, A phosphorus-carbon framework over activated carbon supported palladium nanoparticles for the chemoselective hydrogenation of para-chloronitrobenzene, Catal. Sci. Technol. 7 (7) (2017) 1581-1589.
[13] D. Formenti, F. Ferretti, C. Topf, A.E. Surkus, M.M. Pohl, J. Radnik, M. Schneider, K. Junge, M. Beller, F. Ragaini, Co-based heterogeneous catalysts from well-defined α-diimine complexes: discussing the role of nitrogen, J. Catal. 351 (2017) 79-89.
[14] M. Orlandi, D. Brenna, R. Harms, S. Jost, M. Benaglia, Recent developments in the reduction of aromatic and aliphatic nitro compounds to amines, Org. Process. Res. Dev. 22 (4) (2018) 430-445.
[15] S.Y. Nie, S.Z. Yang, P.F. Zhang, Solvent-free synthesis of mesoporous platinum-aluminum oxide via mechanochemistry: toward selective hydrogenation of nitrobenzene to aniline, Chem. Eng. Sci. 220 (2020) 115619.
[16] J.H. Lyu, J.G. Wang, C.S. Lu, L. Ma, Q.F. Zhang, X.B. He, X.N. Li, Size-dependent halogenated nitrobenzene hydrogenation selectivity of Pd nanoparticles, J. Phys. Chem. C 118 (5) (2014) 2594-2601.
[17] Q.F. Zhang, Y. Zhou, Y.Q. Xu, Q.T. Wang, W.M. Huang, J.T. Ying, J. Zhou, L. Ma, C.S. Lu, F. Feng, X.N. Li, Regulation of sulfur doping on carbon-supported Pd particles and abnormal relationship between Pd particle size and catalytic performance in selective hydrogenation of o-chloronitrobenzene, Catal. Commun. 143 (2020) 106059.
[18] Bai X, Wei J, Tian B, et al. Size effect on optical and photocatalytic properties in BiFeO₃ nanoparticles[J]. J. Phys. Chem. C, 2016, 120(7): 3595-3601.
[19] P.V. Markov, I.S. Mashkovsky, G.O. Bragina, J. Wärnå, E.Y. Gerasimov, V.I. Bukhtiyarov, A.Y. Stakheev, D.Y. Murzin, Particle size effect in liquid-phase hydrogenation of phenylacetylene over Pd catalysts: experimental data and theoretical analysis, Chem. Eng. J. 358 (2019) 520-530.
[20] J.Y. Sun, H. Qiu, W.G. Cao, H.Y. Fu, H.Q. Wan, Z.Y. Xu, S.R. Zheng, Ultrafine Pd particles embedded in nitrogen-enriched mesoporous carbon for efficient H₂ production from formic acid decomposition, ACS Sustainable Chem. Eng. 7 (2) (2019) 1963-1972.
[21] D. Tasis, N. Tagmatarchis, A. Bianco, M. Prato, Chemistry of carbon nanotubes, Chem. Rev, 106(3)(2006)1105-1136.
[22] S.R. Stoyanov, A.V. Titov, P. Král, Transition metal and nitrogen doped carbon nanostructures, Coord. Chem. Rev. 253 (23-24) (2009) 2852-2871.
[23] H. Yoon, S. Ko, J. Jang, Nitrogen-doped magnetic carbon nanoparticles as catalyst supports for efficient recovery and recycling, Chem. Commun. (14) (2007) 1468-1470.
[24] J. Yu, M.Y. Guo, F. Muhammad, A.F. Wang, F. Zhang, Q. Li, G.S. Zhu, One-pot synthesis of highly ordered nitrogen-containing mesoporous carbon with resorcinol-urea-formaldehyde resin for CO₂ capture, Carbon 69 (2014) 502-514.
[25] W.Z. Shen, W.B. Fan, Nitrogen-containing porous carbons: synthesis and application, J. Mater. Chem. A 1 (4) (2013) 999-1013.
[26] X.Q. Wang, C.G. Liu, D. Neff, P.F. Fulvio, R.T. Mayes, A. Zhamu, Q. Fang, G.R. Chen, H.M. Meyer, B.Z. Jang, S. Dai, Nitrogen-enriched ordered mesoporous carbons through direct pyrolysis in ammonia with enhanced capacitive performance, J. Mater. Chem. A 1 (27) (2013) 7920-7926.
[27] M. Terauchi, M. Tanaka, K. Suzuki, A. Ogino, K. Kimura, Production of zigzag-type BN nanotubes and BN cones by thermal annealing, Chem. Phys. Lett. 324 (5-6) (2000) 359-364.
[28] H. Sajiki, K.H. And, K. Hirota, The formation of a novel Pd/C-Ethylenediamine complex catalyst: chemoselective hydrogenation without deprotection of the O-benzyl and N-cbz groups, J Org Chem 63 (22) (1998) 7990-7992.
[29] T. Ikawa, H. Sajiki, K. Hirota, Highly chemoselective hydrogenation method using novel finely dispersed palladium catalyst on silk-fibroin: its preparation and activity, Tetrahedron 61 (8) (2005) 2217-2231.
[30] A.W. Burgstahler, L.O. Weigel, C.G. Shaefer, Improved modification of the rosenmund reduction, Synthesis 1976 (11) (1976) 767-768.
[31] Á. Prekob, Á. Szamosvölgyi, G. Muránszky, J. Lakatos, Z. Kónya, B. Fiser, B. Viskolcz, L. Vanyorek, Palladium decorated N-doped carbon foam as a highly active and selective catalyst for nitrobenzene hydrogenation, Int J Mol Sci 23 (12) (2022) 6423.
[32] Y. Motoyama, Y. Lee, K. Tsuji, S.H. Yoon, I. Mochida, H. Nagashima, Platinum nanoparticles supported on nitrogen-doped carbon nanofibers as efficient poisoning catalysts for the hydrogenation of nitroarenes, ChemCatChem 3 (10) (2011) 1578-1581.
[33] Y. Liu, Y. Sheng, Y.C. Yin, J.A. Ren, X.R. Lin, X.J. Zou, X.G. Wang, X.G. Lu, Phosphorus-doped activated coconut shell carbon-anchored highly dispersed Pt for the chemoselective hydrogenation of nitrobenzene to p-aminophenol, ACS Omega 7 (13) (2022) 11217-11225.
[34] V. Ravat, I. Nongwe, R. Meijboom, G. Bepete, N.J. Coville, Pd on boron-doped hollow carbon spheres-PdO particle size and support effects, J. Catal. 305 (2013) 36-45.
[35] R.C. Duncan, B.W. Faughnan, W. Phillips, Inorganic photochromic and cathodochromic recording materials, Hepat. Mon. 9 (10) (1970) 2236-2243.
[36] J.F. Li, S.L. Ding, F.S. Wang, H.C. Zhao, J.F. Kou, M. Akram, M.H. Xu, W. Gao, C. Liu, H. Yang, Z.P. Dong, Platinum clusters anchored on sulfur-doped ordered mesoporous carbon for chemoselective hydrogenation of halogenated nitroarenes, J Colloid Interface Sci 625 (2022) 640-650.
[37] Q.F. Zhang, F. Feng, C. Su, W. Xu, L. Ma, C.S. Lu, X.N. Li, Preparation of supported core-shell structured Pd@PdxSy/C catalysts for use in selective reductive alkylation reaction, RSC Adv. 5 (81) (2015) 66278-66285.
[38] F.S. Dovell, H. Greenfield, Platinum metal sulfides as heterogeneous hydrogenation catalysts, J. Am. Chem. Soc. 87 (12) (1965) 2767-2768.
[39] X.D. Li, M.S. Zhan, K. Wang, Synthesis and mesomorphic properties of bent-shaped molecule with low bent-angle central core and long alkylthio tail, Chin. Chem. Lett. 22 (9) (2011) 1111-1114.
[40] C. Su, X.N. Li, Q.F. Zhang, L. Ma, C.S. Lu, F. Feng, Behavior of adsorbed diphenyl-sulfide on the Pd/C catalyst for o-chloronitrobenzene hydrogenation, Chin. Chem. Lett. 24 (1) (2013) 59-62.
[41] A.J. McCue, J.A. Anderson, Sulfur as a catalyst promoter or selectivity modifier in heterogeneous catalysis, Catal. Sci. Technol. 4 (2) (2014) 272-294.
[42] Q.F. Zhang, K. Li, Y.Z. Xiang, Y. Zhou, Q.T. Wang, L.L. Guo, L. Ma, X.L. Xu, C.S. Lu, F. Feng, J.H. Lv, J. Ni, X.N. Li, Sulfur-doped porous carbon supported palladium catalyst for high selective o-chloro-nitrobenzene hydrogenation, Appl. Catal. A Gen. 581 (2019) 74-81.
[43] L. Ma, J.G. Wang, H.B. Wang, Q.F. Zhang, C.S. Lu, X.B. He, X.N. Li, High halogenated nitrobenzene hydrogenation selectivity over nano Ir particles, Chin. J. Chem. Eng. 25 (3) (2017) 306-312.

Regulation of the selective hydrogenation performance of sulfur-doped carbon-supported palladium on chloronitrobenzene

Regulation of the selective hydrogenation performance of sulfur-doped carbon-supported palladium on chloronitrobenzene

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Jinlong Liu, Chenye Wang, Xingrui Wang, Chen Zhao, Huiquan Li, Ganyu Zhu, Jianbo Zhang. Reconstruction and recovery of anatase TiO₂ from spent selective catalytic reduction catalyst by NaOH hydrothermal method[J]. 中国化学工程学报, 2023, 60(8): 53-60.
[2]	Yifan Jiang, Bingqi Xie, Jisong Zhang. Highly reactive and reusable heterogeneous activated carbons-based palladium catalysts for Suzuki-Miyaura reaction[J]. 中国化学工程学报, 2023, 60(8): 165-172.
[3]	Peipei Ai, Huiqing Jin, Jie Li, Xiaodong Wang, Wei Huang. Ultra-stable Cu-based catalyst for dimethyl oxalate hydrogenation to ethylene glycol[J]. 中国化学工程学报, 2023, 60(8): 186-193.
[4]	Yuehua Liu, Lili Chen, Shoujun Liu, Song Yang, Ju Shangguan. Role of iron-based catalysts in reducing NO_x emissions from coal combustion[J]. 中国化学工程学报, 2023, 59(7): 1-8.
[5]	Fei Li, Xuemei Wang, Pengze Zhang, Qinqin Wang, Mingyuan Zhu, Bin Dai. Nitrogen and phosphorus co-doped activated carbon induces high density Cu⁺ active center for acetylene hydrochlorination[J]. 中国化学工程学报, 2023, 59(7): 193-199.
[6]	Jiajia Chen, Xinyu Lu, Dandan Wang, Pengcheng Xiu, Xiaoli Gu. Effective depolymerization of alkali lignin using an attapulgite-Ce_0.75Zr_0.25O₂(ATP-CZO)-supported cobalt catalyst in ethanol/isopropanol media[J]. 中国化学工程学报, 2023, 57(5): 50-62.
[7]	Bin Gao, Junwen Chen, Qi Zuo, Hongyan Wang, Wenlin Li. The critical role of Zr in controlling the activity of Pd/Beta on the hydrogenation of phenol to cyclohexanone[J]. 中国化学工程学报, 2023, 57(5): 79-87.
[8]	Linlin Su, Meijun Chen, Li Gong, Hua Yang, Chao Chen, Jun Wu, Ling Luo, Gang Yang, Lulu Long. Boost activation of peroxymonosulfate by iron doped K_2-xMn₈O₁₆: Mechanism and properties[J]. 中国化学工程学报, 2023, 57(5): 88-97.
[9]	Qi Yang, Weikang Dai, Maoshuai Li, Jie Wei, Yi Feng, Cheng Yang, Wanxin Yang, Ying Zheng, Jie Ding, Mei-Yan Wang, Xinbin Ma. Enhanced selective hydrogenation of glycolaldehyde to ethylene glycol over Cu⁰-Cu⁺ sites[J]. 中国化学工程学报, 2023, 57(5): 141-150.
[10]	Shanshan Mao, Tao Shen, Qing Zhao, Tong Han, Fan Ding, Xin Jin, Manglai Gao. Selective capture of silver ions from aqueous solution by series of azole derivatives-functionalized silica nanosheets[J]. 中国化学工程学报, 2023, 57(5): 319-328.
[11]	Bingxiao Feng, Lining Hao, Chaoting Deng, Jiaqiang Wang, Hongbing Song, Meng Xiao, Tingting Huang, Quanhong Zhu, Hengjun Gai. A highly hydrothermal stable copper-based catalyst for catalytic wet air oxidation of m-cresol in coal chemical wastewater[J]. 中国化学工程学报, 2023, 57(5): 338-348.
[12]	Shujun Peng, Song Lei, Sisi Wen, Jian Xue, Haihui Wang. A Ruddlesden–Popper oxide as a carbon dioxide tolerant cathode for solid oxide fuel cells that operate at intermediate temperatures[J]. 中国化学工程学报, 2023, 56(4): 25-32.
[13]	Tutuk Djoko Kusworo, Monica Yulfarida, Andri Cahyo Kumoro, Dani Puji Utomo. Purification of bioethanol fermentation broth using hydrophilic PVA crosslinked PVDF-GO/TiO₂ membrane[J]. 中国化学工程学报, 2023, 55(3): 123-136.
[14]	Da Ke, Minjia Wang, Jiancheng Ruan, Xinzhi Chen, Shaodong Zhou. Efficient, continuous oxidation of durene to pyromellitic dianhydride mediated by a V-Ti-P ternary catalyst: The remarkable doping effect[J]. 中国化学工程学报, 2023, 55(3): 156-164.
[15]	Qiongna Xiao, Yuyan Jiang, Weiqiang Yuan, Jingjing Chen, Haohong Li, Huidong Zheng. Styrene epoxidation catalyzed by polyoxometalate/quaternary ammonium phase transfer catalysts: The effect of cation size and catalyst deactivation mechanism[J]. 中国化学工程学报, 2023, 55(3): 192-201.