The Modification of Diphenyl Sulfide to Pd/C Catalyst and Its Application in Selective Hydrogenation of p-Chloronitrobenzene

doi:10.1016/j.cjche.2014.08.007

›› 2014, Vol. 22 ›› Issue (10): 1111-1116.DOI: 10.1016/j.cjche.2014.08.007

• 催化、动力学与反应工程 • 上一篇下一篇

The Modification of Diphenyl Sulfide to Pd/C Catalyst and Its Application in Selective Hydrogenation of p-Chloronitrobenzene

Qunfeng Zhang, Chang Su, Jie Cen, Feng Feng, Lei Ma, Chunshan Lu, Xiaonian Li

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

收稿日期:2014-04-14 修回日期:2014-07-06 出版日期:2014-10-28 发布日期:2014-12-01
通讯作者: Xiaonian Li
基金资助:
Supported by National Basic Research Program of China (2011CB710800) and Zhejiang Provincial Natural Science Foundation of China (LY12B03009).

The Modification of Diphenyl Sulfide to Pd/C Catalyst and Its Application in Selective Hydrogenation of p-Chloronitrobenzene

Qunfeng Zhang, Chang Su, Jie Cen, Feng Feng, Lei Ma, Chunshan Lu, Xiaonian Li

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

Received:2014-04-14 Revised:2014-07-06 Online:2014-10-28 Published:2014-12-01
Supported by:
Supported by National Basic Research Program of China (2011CB710800) and Zhejiang Provincial Natural Science Foundation of China (LY12B03009).

摘要/Abstract

摘要： In this study, diphenyl sulfide (Ph₂S) was employed to prepare a series of Ph₂S-modified Pd/C catalysts (Pd-Ph₂S/C). Catalyst characterization carried out by Brunner-Emmet-Teller (BET), energy dispersive spectrometer (EDS), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and CO chemisorption uptakemeasurements suggested a chemical interaction between Ph₂S and Pd. The ligand was preferably absorbed on the active site of Pd metal but after increasing the amount of Ph₂S, the adsorption of Ph₂S on Pd metal tended to be saturated and the excess of Ph₂S partially adsorbed on the activated carbon. A part of Pd atoms without adsorbing any Ph₂S still existed, even for the saturated Pd-Ph₂S/C catalyst. The Pd-Ph₂S/C catalysts exhibited a good selectivity of p-chloroaniline (p-CAN) in the hydrogenation of p-chloronitrobenzene (p-CNB). However, the chemisorption between Ph₂S and Pdwas not so strong that part of Ph₂Swas leached fromPd-Ph₂S/C catalyst during the hydrogenation,which caused the decline of the selectivity of p-CAN over the used Pd-Ph₂S/C catalyst. Resulfidation of the used Pd-Ph₂S/C catalystwas effective to resume its stability, and the regenerated Pd-Ph₂S/C catalyst could be reused for at least ten runs with a stable catalytic performance.

关键词: Diphenyl sulfide, Modification, p-Chloronitrobenzene, Pd/C, Selective hydrogenation, Stability

Abstract: In this study, diphenyl sulfide (Ph₂S) was employed to prepare a series of Ph₂S-modified Pd/C catalysts (Pd-Ph₂S/C). Catalyst characterization carried out by Brunner-Emmet-Teller (BET), energy dispersive spectrometer (EDS), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and CO chemisorption uptakemeasurements suggested a chemical interaction between Ph₂S and Pd. The ligand was preferably absorbed on the active site of Pd metal but after increasing the amount of Ph₂S, the adsorption of Ph₂S on Pd metal tended to be saturated and the excess of Ph₂S partially adsorbed on the activated carbon. A part of Pd atoms without adsorbing any Ph₂S still existed, even for the saturated Pd-Ph₂S/C catalyst. The Pd-Ph₂S/C catalysts exhibited a good selectivity of p-chloroaniline (p-CAN) in the hydrogenation of p-chloronitrobenzene (p-CNB). However, the chemisorption between Ph₂S and Pdwas not so strong that part of Ph₂Swas leached fromPd-Ph₂S/C catalyst during the hydrogenation,which caused the decline of the selectivity of p-CAN over the used Pd-Ph₂S/C catalyst. Resulfidation of the used Pd-Ph₂S/C catalystwas effective to resume its stability, and the regenerated Pd-Ph₂S/C catalyst could be reused for at least ten runs with a stable catalytic performance.

Key words: Diphenyl sulfide, Modification, p-Chloronitrobenzene, Pd/C, Selective hydrogenation, Stability

Qunfeng Zhang, Chang Su, Jie Cen, Feng Feng, Lei Ma, Chunshan Lu, Xiaonian Li. The Modification of Diphenyl Sulfide to Pd/C Catalyst and Its Application in Selective Hydrogenation of p-Chloronitrobenzene[J]. , 2014, 22(10): 1111-1116.

参考文献

[1] L. Ma, S. Chen, C. Lu, Q. Zhang, X. Li, Highly selective hydrogenation of 3,4-dichloronitrobenzene over Pd/C catalysts without inhibitors, Catal. Today 173 (2011) 62-67.
[2] G. Petrucci, W. Oberhauser, M. Bartoli, G. Giachi, M. Frediani, E. Passaglia, L. Capozzoli, L. Rosi, Pd-nanoparticles supported onto functionalized poly(lactic acid)-based stereocomplexes for partial alkyne hydrogenation, Appl. Catal. A Gen. 469 (2014) 132-138.
[3] B. Li, X. Li, H. Wang, P. Wu, Pt nanoparticles entrapped in ordered mesoporous carbon for enantioselective hydrogenation, J. Mol. Catal. A Chem. 345 (2011) 81-89.
[4] P. Chen, L.M. Chew,W. Xia, The influence of the residual growth catalyst in functionalized carbon nanotubes on supported Pt nanoparticles applied in selective olefin hydrogenation, J. Catal. 307 (2013) 84-93.
[5] A. Borodziński, G.C. Bond, Selective hydrogenation of ethyne in ethane rich streams on palladium catalysts, Part 2: Steady state kinetics and effects of palladiumparticle size, carbon monoxide, and promoters, Catal. Rev. Sci. Eng. 50 (2008) 379-469.
[6] S.A. Nikolaev, L.N. Zanaveskin, V.V. Smirnov, V.A. Averyanov, K.L. Zanaveskin, Catalytic hydrogenation of alkyne and alkadiene impurities in alkenes. Practical and theoretical aspects, Russ. Chem. Rev. 78 (2009) 231-247.
[7] F.M. McKenna, J.A. Anderson, Selectivity enhancement in acetylene hydrogenation over diphenyl sulphide-modified Pd/TiO₂ catalysts, J. Catal. 281 (2011) 231-240.
[8] F.M.McKenna, R.P.K.Wells, J.A. Anderson, Enhanced selectivity in acetylene hydrogenation by ligand modified Pd/TiO₂ catalysts, Chem. Commun. 47 (2010) 2351-2353.
[9] C. Su, X. Li, Q. Zhang, L. Ma, C. Lu, F. Feng, Behavior of adsorbed diphenyl-sulfide on the Pd/C catalyst for o-chloronitrobenzene hydrogenation, Chin. Chem. Lett. 24 (2013) 59-62.
[10] H. Greenfield, F.S. Dovell, Metal sulfide catalysts for hydrogenation of halonitrobenzenes to haloanilines, J. Org. Chem. 32 (1967) 3670-3671.
[11] Q. Zhang, J.Wu, C. Su, F. Feng, Q. Ding, Z. Yuan, H.Wang, L. Ma, C. Lu, X. Li, Preparation, structural characterization of a novel egg-shell palladium sulfide catalyst and its application in selective reductive alkylation reaction, Chin. Chem. Lett. 23 (2012) 1111-1114.
[12] C. D. Keith, D. L. Bair, Method of preparing a sulfided platinum on carbon catalyst, U.S. Patent. 3275567 (1966).
[13] Frederick S Dovell, Harold Greenfield, Hydrogenation with platinum metal sulfide catalyst [P], U.S. Patent, 3336386 (1967).
[14] H. Greenfield, F.S. Dovell, Rhodium sulfide catalyzed reductive alkylation of 1,5-naphthalenediamine, J. Org. Chem. 31 (1966) 3053-3053.
[15] A. Mori, Y. Miyakawa, E. Ohashi, T. Haga, T. Maegawa, H. Sajiki, Pd/C-catalyzed chemoselective hydrogenation in the presence of diphenylsulfide, Org. Lett. 8 (2006) 3279-3281.
[16] A. Mori, T. Mizusaki, M. Kawase, T. Maegawa, Y. Monguchi, S. Takao, Y. Takagi, H. Sajiki, Novel palladium-on-carbon/diphenyl sulfide complex for chemoselective hydrogenation: preparation, characterization, and application, Adv. Synth. Catal. 350 (2008) 406-410.
[17] A.Mori, T.Mizusaki,Y.Miyakawa, E.Ohashi,T.Haga,T.Maegawa, Y.Monguchi,H.Sajiki, Chemoselective hydrogenation method catalyzed by Pd/C using diphenylsulfide as a reasonable catalyst poison, Tetrahedron 62 (2006) 11925-11932.
[18] Y. Takenaka, T. Kiyosu, J.C. Choi, T. Sakakura, H. Yasuda, Selective synthesis of N-aryl hydroxylamines by the hydrogenation of nitroaromatics using supported platinum catalysts, Green Chem. 11 (2009) 1385-1390.
[19] M. Bergfeld, H. G. Zengel, Process for the preparation of asymmetrical N-phenyl-N'-substituted para-phenylene diamines, U.S. Patent, 4210601 (1980).
[20] Q. Zhang, J. Lv, L. Ma, C. Lu, W. Liu, X. Li, Study on deactivation by sulfur and regeneration of Pd/C catalyst in hydrogenation of N-(3-nitro-4-methoxyphenyl) acetamide, Chin. J. Chem. Eng. 21 (2013) 622-626.
[21] A. Mikołajczuk, A. Borodzinski, P. Kedzierzawski, L. Stobinski, B. Mierzwa, R. Dziura, Deactivation of carbon supported palladium catalyst in direct formic acid fuel cell, Appl. Surf. Sci. 257 (2011) 8211-8214.
[22] H. Ohtsuka, The oxidation of methane at low temperatures over zirconia-supported Pd, Ir and Pt catalysts and deactivation by sulfur poisoning, Catal. Lett. 141 (2011) 413-419.
[23] S.L. Florica, V. Meille, S. Pallier, E. Chaînet, C.D. Bellefon, Regeneration of deactivated catalysts coated on foamand monolith: Example of Pd/C for nitrobenzene hydrogenation, Appl. Catal. A Gen. 453 (2013) 28-33.
[24] P. Albers, J. Pietsch, Stewart F. Parker, Poisoning and deactivation of palladium catalysts, J. Mol. Catal. A Chem. 173 (2001) 275-286.

The Modification of Diphenyl Sulfide to Pd/C Catalyst and Its Application in Selective Hydrogenation of p-Chloronitrobenzene

The Modification of Diphenyl Sulfide to Pd/C Catalyst and Its Application in Selective Hydrogenation of p-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]	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]	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.
[3]	Xia Xiong, Zuohua Liu, Changyuan Tao, Yundong Wang, Fangqin Cheng, Hong Li. Reduced power consumption in stirred vessel with high solid loading by equipping punched baffles[J]. 中国化学工程学报, 2023, 56(4): 203-214.
[4]	Tinghao Jia, Yunbo Yu, Qing Liu, Yao Yang, Ji-Jun Zou, Xiangwen Zhang, Lun Pan. Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine[J]. 中国化学工程学报, 2023, 56(4): 225-232.
[5]	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.
[6]	Suhang Jiang, Lijuan Tan, Yujia Tong, Lijian Shi, Weixing Li. A heterogeneous double chamber electro-Fenton with high production of H₂O₂ using La–CeO₂ modified graphite felt as cathode[J]. 中国化学工程学报, 2023, 54(2): 98-105.
[7]	Xiaodong Yang, Na Yang, Ziqiang Gong, Feifei Peng, Bin Jiang, Yongli Sun, Luhong Zhang. The superhydrophobic sponge decorated with Ni-Co double layered oxides with thiol modification for continuous oil/water separation[J]. 中国化学工程学报, 2023, 54(2): 296-305.
[8]	Dahai Jiang, Zhidi Min, Jing Leng, Huanqing Niu, Yong Chen, Dong Liu, Chenjie Zhu, Ming Li, Wei Zhuang, Hanjie Ying. Characterization of two halophilic adenylate cyclases from Thermobifida halotolerans and Haloactinopolyspora alba[J]. 中国化学工程学报, 2023, 53(1): 56-62.
[9]	Lu Lv, Min Zhao, Yanan Liu, Yufei He, Dianqing Li. Fabrication of hydrophobic Pd/Al₂O₃-phosphoric acid via P-O-Al bond for liquid hydrogenation reaction[J]. 中国化学工程学报, 2023, 53(1): 232-242.
[10]	Ting He, Songhong Yu, Jinhui He, Dejian Chen, Jie Li, Hongjun Hu, Xingrui Zhong, Yawei Wang, Zhaohui Wang, Zhaoliang Cui. Membranes for extracorporeal membrane oxygenator (ECMO): History, preparation, modification and mass transfer[J]. 中国化学工程学报, 2022, 49(9): 46-75.
[11]	Linyang Wang, Qiang Wang, Yongqi Liu, Qiuxiang Yao, Ming Sun, Xiaoxun Ma. Catalytic conversion of asphaltenes to BTXN using metal-loaded modified HZSM-5[J]. 中国化学工程学报, 2022, 49(9): 253-264.
[12]	Pascal Habimana, Yanjun Jiang, Jing Gao, Jean Bernard Ndayambaje, Osama M. Darwesh, Jean Pierre Mwizerwa, Xiaobing Zheng, Li Ma. Enhancing laccase stability and activity for dyes decolorization using ZIF-8@MWCNT nanocomposite[J]. 中国化学工程学报, 2022, 48(8): 66-75.
[13]	Chunyu Zhang, Yan Sun, Xiaoyan Dong. Conjugation of a zwitterionic polymer with dimethyl chains to lipase significantly increases the enzyme activity and stability[J]. 中国化学工程学报, 2022, 47(7): 48-53.
[14]	Fu Yang, Wenhao Li, Rui Ou, Yutong Lu, Xuexue Dong, Wenlong Tu, Wenjian Zhu, Xuyu Wang, Lulu Li, Aihua Yuan, Jianming Pan. Superb VOCs capture engineering carbon adsorbent derived from shaddock peel owning uncompromising thermal-stability and adsorption property[J]. 中国化学工程学报, 2022, 47(7): 120-133.
[15]	Jinglei Cui, Qian Wang, Jianming Gao, Yanxia Guo, Fangqin Cheng. The selective adsorption of rare earth elements by modified coal fly ash based SBA-15[J]. 中国化学工程学报, 2022, 47(7): 155-164.