Study on Deactivation by Sulfur and Regeneration of Pd/C Catalyst in Hydrogenation of N-(3-nitro-4-methoxyphenyl) Acetamide

doi:10.1016/S1004-9541(13)60497-8

Chinese Journal of Chemical Engineering ›› 2013, Vol. 21 ›› Issue (6): 622-626.DOI: 10.1016/S1004-9541(13)60497-8

• 催化、动力学与反应工程 • 上一篇下一篇

Study on Deactivation by Sulfur and Regeneration of Pd/C Catalyst in Hydrogenation of N-(3-nitro-4-methoxyphenyl) Acetamide

张群峰, 吕井辉, 马磊, 卢春山, 刘维, 李小年

Industrial Catalysis Institute, State Key Laboratory Breeding Base of Green Chemistry Synthesis Technology, Zhejiang University of Technology, Hangzhou 310032, China

收稿日期:2012-12-13 修回日期:2013-03-09 出版日期:2013-06-28 发布日期:2013-07-03
通讯作者: LI Xiaonian
基金资助:
Supported by the Natural Science Foundation of Zhejiang Provincial (LY12B03009) and Program for Zhejiang Leading Team of Science and Technology Innovation (2011R09020-03).

Study on Deactivation by Sulfur and Regeneration of Pd/C Catalyst in Hydrogenation of N-(3-nitro-4-methoxyphenyl) Acetamide

ZHANG Qunfeng, LÜ Jinghui, MA Lei, LU Chunshan, LIU Wei, LI Xiaonian

Industrial Catalysis Institute, State Key Laboratory Breeding Base of Green Chemistry Synthesis Technology, Zhejiang University of Technology, Hangzhou 310032, China

Received:2012-12-13 Revised:2013-03-09 Online:2013-06-28 Published:2013-07-03
Contact: LI Xiaonian
Supported by:
Supported by the Natural Science Foundation of Zhejiang Provincial (LY12B03009) and Program for Zhejiang Leading Team of Science and Technology Innovation (2011R09020-03).

摘要/Abstract

摘要： Deactivation of Pd/C catalyst often occurs in liquid hydrogenation using industrial materials. For instance, the Pd/C catalyst is deactivated severely in the hydrogenation of N-(3-nitro-4-methoxyphenyl) acetamide. In this study, the chemisorption of sulfur on the surface of deactivated Pd/C was detected by energy dispersive spectrometer and X-ray photoelectron spectroscopy. Sulfur compounds poison the Pd/C catalyst and increase the formation of azo deposit, reducing the activity of catalyst. We report a mild method to regenerate the Pd/C catalyst: wash the deposit by N,N-dimethylformamide and oxidize the chemisorbed sulfur by hot air. The regenerated Pd/C catalyst can be reused at least ten runs with stable activity.

关键词: Pd/C catalyst, hydrogenation, deactivation, regeneration, sulfur

Abstract: Deactivation of Pd/C catalyst often occurs in liquid hydrogenation using industrial materials. For instance, the Pd/C catalyst is deactivated severely in the hydrogenation of N-(3-nitro-4-methoxyphenyl) acetamide. In this study, the chemisorption of sulfur on the surface of deactivated Pd/C was detected by energy dispersive spectrometer and X-ray photoelectron spectroscopy. Sulfur compounds poison the Pd/C catalyst and increase the formation of azo deposit, reducing the activity of catalyst. We report a mild method to regenerate the Pd/C catalyst: wash the deposit by N,N-dimethylformamide and oxidize the chemisorbed sulfur by hot air. The regenerated Pd/C catalyst can be reused at least ten runs with stable activity.

Key words: Pd/C catalyst, hydrogenation, deactivation, regeneration, sulfur

张群峰, 吕井辉, 马磊, 卢春山, 刘维, 李小年. Study on Deactivation by Sulfur and Regeneration of Pd/C Catalyst in Hydrogenation of N-(3-nitro-4-methoxyphenyl) Acetamide[J]. Chinese Journal of Chemical Engineering, 2013, 21(6): 622-626.

ZHANG Qunfeng, LÜ Jinghui, MA Lei, LU Chunshan, LIU Wei, LI Xiaonian . Study on Deactivation by Sulfur and Regeneration of Pd/C Catalyst in Hydrogenation of N-(3-nitro-4-methoxyphenyl) Acetamide[J]. Chin.J.Chem.Eng., 2013, 21(6): 622-626.

参考文献

1 Huu, T.T., Chizari, K., Janowska, I., Moldovan, M.S., Ersen, O., Nguyen, L.D., Ledoux, M.J., Huu, C.P., Begin, D., “Few-layer graphene supporting palladium nanoparticles with a fully accessible effective surface for liquid-phase hydrogenation reaction”, Catalysis Today, 189, 77-82 (2012).

2 Guo, S.Z., Xu, Z.H., Xia, R.H., Zhou, F., Fang, D.Y., “Kinetics on hydrogenation of cyclopentadiene over Pd/γ-Al₂O₃ catalyst”, Chin. J. Chem. Eng., 13, 623-627 (2005).

3 Albers, P., Pietsch, J., Parker, S.F., “Poisoning and deactivation of palladium catalysts”, Journal of Molecular Catalysis A: Chemical, 173, 275-286 (2001).

4 Trimm, D.L., “The regeneration or disposal of deactivated heterogeneous catalysts”, Applied Catalysis A: General, 212, 153-160 (2001).

5 Lowry, G.V., Reinhard, M., “Pd-Catalyzed TCE dechlorination in groundwater: Solute effects, biological control, and oxidative catalyst regeneration”, Environmental Science & Technology, 34, 3217-3223 (2000).

6 Munakata, N., Reinhard, M., “Palladium-catalyzed aqueous hydrodehalogenation in column reactors: Modeling of deactivation kinetics with sulphide and comparison of regenerants”, Applied Catalysis B: Environmental, 75, 1-10 (2007).

7 Xiao, T.C., An, L.D., “Mechanism of sulfur poisoning on supported noble metal catalyst—the adsorption and transformation of sulfur on palladium catalysts with different supports”, Catalysis Letters, 12, 287-296 (1992).

8 Yurkina, O.V., De Vekki, A.V., Kraev, Y.L., “Mechanism of deactivation of palladium-containing hydrogenation catalysts in the presence of sulfur compounds”, Petroleum Chemistry, 44 (3), 160-165 (2004).

9 Miko?ajczuk, A., Borodzinski, A., Kedzierzawski, P., Stobinski, L., Mierzwa, B., Dziura, R., “Deactivation of carbon supported palladium catalyst in direct formic acid fuel cell”, Applied Surface Science, 257, 8211-8214 (2011).

10 Zhang, X.X., Zong, B.N., Min, E.Z., Lu, L.J., “Method for regenerating a palladium catalyst”, China Pat., 03122844.5 (2003).

11 Li, W.X., Bo, Z.F., Qian, Z.M., “Palladium-carbon catalyst on-line regeneration method for terephthalic acid production apparatus”, China Pat., 00112558.3 (2000).

12 Zhang, X.P., Sui, Z.J., Zhou, X.G., Yuan, W.K., “Modeling and simulation of coke combustion regeneration for coked Cr₂O₃/Al₂O₃ propane dehydrogenation catalyst”, Chin. J. Chem. Eng., 18, 618-625 (2010).

13 Schwartz, W.R., Ciuparu, D., Pfefferle, L.D., “Combustion of methane over palladium-based catalysts: Catalytic deactivation and role of the support”, Journal of Physical Chemistry C, 116 (15), 8587-8593 (2012).

14 Ping, E.W., Pierson, J., Wallace, R., Miller, J.T., Fuller, T.F., Jones, C.W., “On the nature of the deactivation of supported palladium nanoparticle catalysts in the decarboxylation of fatty acids”, Applied Catalysis A: General, 396 (1-2), 85-90 (2011).

15 Gross, M.S., Pisarello, M.L., Pierpauli, K.A., Querini, C.A., “Catalytic deoxygenation of water: Preparation, deactivation, and regeneration of palladium on a resin catalyst”, Industrial & Engineering Chemistry Research, 49 (1), 81-88 (2010).

16 Ordonez, S., Diez, F.V., Sastre, H., “Characterisation of the deactivation of platinum and palladium supported on activated carbon used as hydrodechlorination catalysts”, Applied Catalysis B: Environmental, 31 (2), 113-122 (2001).

17 Salame, I.I., Bandosz, T.J., “Surface chemistry of activated carbons: Combining the results of temperature-programmed desorption, Boehm, and potentiometric titrations”, Journal of Colloid and Interface Science, 240, 252-258 (2001).

18 Bandosz, T.J., Jagiello, J., Schwarz, J.A., “Comparison of methods to assess surface acidic groups on activated carbons”, Analytical Chemistry, 64, 891-895 (1992).

19 Zhang, Q.F., Lü, J.H., Ma, L., Lu, C.S., Xu, X.L., Liang, Q.X., Li, X.N., “Catalytic hydrogenation for the green synthesis of N-(3-Amino-4-methoxyphenyl) acetamide”, Fine Chemical Intermediate, 38, 41-43 (2008).

20 Nishimura, S., Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, John Wiley & Sons Inc., New York, 325 (2001).

21 Takenaka, Y., Kiyosu, T., Choi, J.C., Sakakura, T., Yasuda, H., “Selective synthesis of N-aryl hydroxylamines by the hydrogenation of nitroaromatics using supported platinum catalysts”, Green Chemistry, 11, 1385-1390 (2009).

[1]	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.
[2]	Alexander Nti Kani, Evans Dovi, Aaron Albert Aryee, Runping Han, Zhaohui Li, Lingbo Qu. Mechanisms and reusability potentials of zirconium-polyaziridine-engineered tiger nut residue towards anionic pollutants[J]. 中国化学工程学报, 2023, 60(8): 275-292.
[3]	Lijuan Zhao, Zhe Tan, Xiaoguang Zhang, Qijun Zhang, Wei Wang, Qiang Deng, Jie Ma, De'an Pan. Research on process modeling and simulation of spent lead paste desulfurization enhanced reactor[J]. 中国化学工程学报, 2023, 60(8): 293-303.
[4]	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.
[5]	Yutong Jiang, Yifeng Chen, Fuliu Yang, Jixue Fan, Jun Li, Zhuhong Yang, Xiaoyan Ji. Efficient SO₂ removal using aqueous ionic liquid at low partial pressure[J]. 中国化学工程学报, 2023, 58(6): 355-363.
[6]	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.
[7]	Yunchang Fan, Chunyan Zhu, Sheli Zhang, Lei Zhang, Qiang Wang, Feng Wang. Efficient and selective extraction of sinomenine by deep eutectic solvents[J]. 中国化学工程学报, 2023, 57(5): 109-117.
[8]	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.
[9]	Shiyong Xing, Yan Cui, Tiefeng Wang, Jinwei He, Minghan Han. Elucidating the effect of oxides on the zeolite catalyzed alkylation of benzene with 1-dodecene[J]. 中国化学工程学报, 2023, 56(4): 126-135.
[10]	Zida Ma, Yuxia Li, Mengmeng Jin, Xiaoqin Liu, Linbing Sun. Fabrication of adsorbents with enhanced Cu^I stability: Creating a superhydrophobic microenvironment through grafting octadecylamine[J]. 中国化学工程学报, 2023, 55(3): 41-48.
[11]	Zhenzhou Ma, Xu Hou, Bochong Chen, Liu Zhao, Enxian Yuan, Tingting Cui. Experiment and modeling of coke formation and catalyst deactivation in n-heptane catalytic cracking over HZSM-5 zeolites[J]. 中国化学工程学报, 2023, 55(3): 165-172.
[12]	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.
[13]	Peipei Ai, Li Zhang, Jinchi Niu, Huiqing Jin, Wei Huang. Boron-doped lamellar porous carbon supported copper catalyst for dimethyl oxalate hydrogenation[J]. 中国化学工程学报, 2023, 55(3): 222-229.
[14]	Yu Wang, Qunfeng Zhang, Xinlei Liu, Junqi Weng, Guanghua Ye, Xinggui Zhou. Probing deactivation by coking in catalyst pellets for dry reforming of methane using a pore network model[J]. 中国化学工程学报, 2023, 55(3): 293-303.
[15]	Xianglin Liu, Minjie Xu, Chenxi Cao, Zixu Yang, Jing Xu. Effects of zinc on χ-Fe₅C₂ for carbon dioxide hydrogenation to olefins: Insights from experimental and density function theory calculations[J]. 中国化学工程学报, 2023, 54(2): 206-214.

Study on Deactivation by Sulfur and Regeneration of Pd/C Catalyst in Hydrogenation of N-(3-nitro-4-methoxyphenyl) Acetamide

Study on Deactivation by Sulfur and Regeneration of Pd/C Catalyst in Hydrogenation of N-(3-nitro-4-methoxyphenyl) Acetamide

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