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Hydrogenation of nitrobenzene over a composite catalyst based on zeolite supported N-doped carbon nanotubes decorated with palladium

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Abstract

A catalyst nanocomposite was synthesized based on zeolite supported nitrogen-doped carbon nanotubes (N-CNT) decorated with palladium nanoparticles. Zeolite beads impregnated with nickel nitrate solution were used as CCVD catalyst support during the synthesis of N-CNT. Then the zeolite supported N-CNT was decorated with palladium nanoparticles and the final nanocomposite was tested in nitrobenzene hydrogenation. The structure of the nanocomposite was characterized by SEM. The surface of the zeolite beads is extensively covered by N-CNT. The particle size distribution of the palladium nanoparticles on the surface of N-CNT is relatively homogenous (< 7 nm). The catalytic activity of the nanocomposite was the highest at 10 bar and 323 K while the achieved nitrobenzene/aniline conversion was 99.9% after 4 h of hydrogenation.

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References

  1. TDI/MDI (1999, San Francisco) Process Evaluation/Research Planning Program, Chem Systems Report 98/99 S8

  2. Salzinger M, Lercher JA (2011) Reaction network and mechanism of the synthesis of methylenedianiline over dealuminated Y-type zeolites. Green Chem 13:149

    Article  CAS  Google Scholar 

  3. Hatziantoniou V, Andersson B, Schöön NH (1986) Mass transfer and selectivity in liquid-phase hydrogenation of nitro compounds in monolithic catalyst reactor with segmented gas–liquid flow. Ind Eng Chem Proc Des Dev 25:964–970

    Article  CAS  Google Scholar 

  4. Holler V, Wegricht D, Yuranov I, Kiwi-Minsker L, Renken A (2000) Three-phase nitrobenzene hydrogenation over supported glass fiber catalysts: reaction kinetics study. Chem Eng Technol 23:251–255

    Article  CAS  Google Scholar 

  5. Burge HD, Collins DJ, Davis BH (1980) Intermediates in the Raney nickel catalyzed hydrogenation of nitrobenzene to aniline. Ind Eng Chem Prod Res Dev 19:389–391

    Article  CAS  Google Scholar 

  6. Collins DJ, Smith AD, Davis BH (1982) Hydrogenation of nitrobenzene over a nickel boride catalyst. Ind Eng Chem Prod Res Dev 21:279–281

    Article  CAS  Google Scholar 

  7. Wisniak J, Klein M (1984) Reduction of nitrobenzene to aniline. Ind Eng Chem Prod Res De 23:44–50

    Article  CAS  Google Scholar 

  8. Zhu J, Holmen A, Chen D (2013) Carbon nanomaterials in catalysis: proton affinity, chemical and electronic properties, and their catalytic consequences. ChemCatChem 5:378–401

    Article  CAS  Google Scholar 

  9. Liao HG, Xiao YJ, Zhang HK, Liu PL, You KY, Hean C, Luo W (2012) Hydrogenation of nitrocyclohexane to cyclohexanone oxime over Pd/CNT catalyst under mild conditions. Catal Comm 19:80–84

    Article  CAS  Google Scholar 

  10. Fernando M, Pereira JR, Figueiredo L, Serp P, Kalck P, Kihn Y (2004) Catalytic activity of carbon nanotubes in the oxidative dehydrogenation of ethylbenzene. Carbon 42:2807–2813

    Article  Google Scholar 

  11. Xianlong D, Yongmei L, Jianqiang W, Yong CJ (2013) Catalytic conversion of biomass-derived levulinic acid into γ-valerolactone using iridium nanoparticles supported on carbon nanotubes. Catal 34:993–1001

    Google Scholar 

  12. Li L, Wu G, Xu BQ (2006) Electro-catalytic oxidation of CO on Pt catalyst supported on carbon nanotubes pretreated with oxidative acids. Carbon 44:2973–2983

    Article  CAS  Google Scholar 

  13. Liang D, Gao J, Sun H, Chen P, Hou Z, Zheng X (2011) Selective oxidation of glycerol with oxygen in a base-free aqueous solution over MWNTs supported Pt catalysts. Appl Catal B 106:423–432

    Article  CAS  Google Scholar 

  14. Li CH, Yu ZX, Yao KF, Ji SF, Liang J (2005) Nitrobenzene hydrogenation with carbon nanotube-supported platinum catalyst under mild conditions. J Mol Catal A Chem 226:101–105

    Article  CAS  Google Scholar 

  15. Liu S, Hao F, Liu P, Luo H (2015) The influences of preparation methods on the structure and catalytic performance of single-wall carbon nanotubes supported palladium catalysts innitrocyclohexane hydrogenation. RSC Adv 5:22863–22868

    Article  CAS  Google Scholar 

  16. Guoa X, Donga H, Li B, Donga L, Mua X, Chen X (2017) Influence of the functional groups of multiwalled carbon nanotubes on performance of Ru catalysts in sorbitol hydrogenolysis to glycols. J Mol Catal A Chem 426:79–87

    Article  Google Scholar 

  17. Ratso S, Kruusenberg I, Joost U, Saar R, Tammeveski K (2016) Enhanced oxygen reduction reaction activity of nitrogen-doped graphene/multi-walled carbon nanotube catalysts in alkaline media international journal of hydrogen energy. Int J Hydrogen Energy 41:22510–22519

    Article  CAS  Google Scholar 

  18. Ibrahim EMM, Khavrus VO, Leonhardt A, Hampel S, Oswald S, Rümmeli MH, Büchner B (2010) Synthesis, characterization, and electrical properties of nitrogendoped single-walled carbon nanotubes with different nitrogen content. Diamond Relat Mater 19:1199–1206

    Article  CAS  Google Scholar 

  19. García-García FR, Àlvarez-Rodríguez J, Rodríguez-Ramos I, Guerrero-Ruiz A (2010) The use of carbon nanotubes with and without nitrogen doping as support for ruthenium catalysts in the ammonia decomposition reaction. Carbon 48:267–276

    Article  Google Scholar 

  20. An W, Turner CHJ (2009) Chemisorption of transition-metal atoms on boron- and nitrogen-doped carbon nanotubes: energetics and geometric and electronic structures. J Phys Chem C 113:7069–7078

    Article  CAS  Google Scholar 

  21. Vanyorek L, HalasiGy Pekker P, Kristály F, Kónya Z (2016) Characterization and catalytic activity of different carbon supported Pd nanocomposites. Catal Lett 146:2268–2277

    Article  CAS  Google Scholar 

  22. Al-Johani H, A-Salam M (2011) Kinetics and thermodynamic study of aniline adsorption by multi-walled carbon nanotubes from aqueous solution. J Coll Int Sci 360:760–767

    Article  CAS  Google Scholar 

  23. Turáková M, Salmi T, Eranen K, Warná J, Y-Murzin D (2015) Liquid phase hydrogenation of nitrobenzene. Appl Catal A Gen 499:66–76

    Article  Google Scholar 

  24. Dong B, Li Y, Ning X, Wang H, Yu H, Peng F (2017) Trace iron impurities deactivate palladium supported on nitrogen-doped carbon nanotubes for nitrobenzene hydrogenation. Appl Catal A Gen 545:54–63

    Article  CAS  Google Scholar 

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Acknowledgements

This research was supported by the European Union and the Hungarian State, co-financed by the European Regional Development Fund in the framework of the GINOP-2.3.4-15-2016-00004 Project, aimed to promote the cooperation between the higher education and the industry.

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Authors and Affiliations

  1. Institute of Chemistry, University of Miskolc, Miskolc-Egyetemváros, 3515, Hungary

    Ádám Prekob, Gábor Muránszky, Zsuzsa G. Hutkai, Béla Fiser, Béla Viskolcz & László Vanyorek

  2. Research Institute of Biomolecular and Chemical Engineering, University of Pannonia, Veszprém , Egyetem str. 10, 8200, Hungary

    Péter Pekker

  3. Institute of Mineralogy and Geology, University of Miskolc, Miskolc-Egyetemváros, 3515, Hungary

    Ferenc Kristály

  4. Ferenc Rákóczi II. Transcarpathian Hungarian Institute, Beregszász, Transcarpathia, 90200, Ukraine

    Béla Fiser

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  1. Ádám Prekob
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  2. Gábor Muránszky
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  3. Zsuzsa G. Hutkai
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  5. Ferenc Kristály
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  7. Béla Viskolcz
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  8. László Vanyorek
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Correspondence to László Vanyorek.

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Prekob, Á., Muránszky, G., Hutkai, Z.G. et al. Hydrogenation of nitrobenzene over a composite catalyst based on zeolite supported N-doped carbon nanotubes decorated with palladium. Reac Kinet Mech Cat 125, 583–593 (2018). https://doi.org/10.1007/s11144-018-1481-2

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