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Synthesis, stability and activity of palladium supported over various inorganic matrices in the selective hydrogenation of nitroaniline

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Abstract

This work aimed to study the influence of catalyst supports on their catalytic activity and physico-chemical properties of resulting material. Such supports as SiO2, γ-Al2O3 and carbon containing 3, 4 or 5% palladium are used for the experiments. The hydrogenation of p-nitroaniline is chosen as a model reaction for testing the synthesized catalysts. Catalysts were studied by different physico-chemical methods in order to reveal the structure and its changes in reaction. XPS data shows the catalyst surface changed its chemical structure. The palladium oxidation state strongly depends on the nature of the matrix. For γ-Al2O3- and SiO2-supported catalysts, the formation of palladium(II) oxide was found to take place, at the same time, the carbon support is characterized by the presence of both palladium(II) oxide and palladium(IV) oxide. Such a difference shows that the nature of the support influences the oxidation state of active metal. The application of carbon matrix provides a lower oxidation state of the active metal due to electron density shift to the support. Temperature programmed desorption of NH3 demonstrates γ-Al2O3 to contain weak, medium and strong acid sites, while activated carbon has only medium and weak ones. Silica has only weak acid sites. A correlation between catalyst activity and acid–base properties was shown.

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References

  1. Cerveny L (1989) Palladium catalysts in hydrogenation reactions. Chem Eng Commun 83(1):31–63

    Article  CAS  Google Scholar 

  2. Jackson SD, Kelly GJ, Watson SR, Gulickx R (1999) Cycloalkene hydrogenation over palladium catalysts. Appl Catal A Gen 187:161–168. https://doi.org/10.1016/S0926-860X(99)00204-5

    Article  CAS  Google Scholar 

  3. Zang W, Li G, Wang L, Zhang X (2015) Catalytic hydrogenation by noble-metal nanocrystals with well-defined facets: a review. Catal Sci Technol 5:2532–2553. https://doi.org/10.1039/C4CY01619J

    Article  CAS  Google Scholar 

  4. Bond GC (1968) Catalysis by metals. 18:

  5. Tseng KH, Lin PY (2015) Application oftaguchi experiment method in parameter optimization of alternating current spot welding of stainless steel. J Technol 30:15–24. https://doi.org/10.1016/j.jcat.2006.01.004

    Article  CAS  Google Scholar 

  6. Delmon B, Froment GF (1999) Hydrotreatment and hydrocracking of oil fractions. In: B. Delmon, G.F. Froment, P. Grange (Ed) Elsevier, Amsterdam, pp 421–425

  7. Pasteur UL, Pascal RB, Strasbourg F, et al (1999) Catalyst deactivation. In: B. Delmon, G.F. Froment (Eds) Elsevier, Amsterdam, pp 179–186

  8. Forzatti P, Lietti L (1999) Catalyst deactivation. Catal Today 52:165–181. https://doi.org/10.1016/S0920-5861(99)00074-7

    Article  CAS  Google Scholar 

  9. Fröhlich G, Kestel U, Łojewska J et al (1996) Activation and deactivation of cobalt catalysts in the hydrogenation of carbon dioxide. Appl Catal A Gen 134:1–19. https://doi.org/10.1016/0926-860X(95)00207-3

    Article  Google Scholar 

  10. Di Serioa M, Velottib R, Leonea U (1994) 5,6,7,8-tetrahydroanthraquinone 88:0–5

    Google Scholar 

  11. Xu C, Lin HJ, Edalati K et al (2018) Superior hydrogenation properties in a Mg65Ce10Ni20Cu5nanoglass processed by melt-spinning followed by high-pressure torsion. Scr Mater 152:137–140. https://doi.org/10.1016/j.scriptamat.2018.04.036

    Article  CAS  Google Scholar 

  12. Kataoka Y, Kawamoto Y, Ono T et al (2015) Hydrogenation of Nd-Fe-B magnet powder under a high pressure of hydrogen. Results Phys 5:99–100. https://doi.org/10.1016/j.rinp.2015.04.001

    Article  Google Scholar 

  13. Mun BS, Liu Z, Motin MA et al (2018) In situ observation of H2 dissociation on the ZnO (0001) surface under high pressure of hydrogen using ambient-pressure XPS. Int J Hydrog Energy 43:8655–8661. https://doi.org/10.1016/j.ijhydene.2018.03.155

    Article  CAS  Google Scholar 

  14. Gaikwad R, Bansode A, Urakawa A (2016) High-pressure advantages in stoichiometric hydrogenation of carbon dioxide to methanol. J Catal 343:127–132. https://doi.org/10.1016/j.jcat.2016.02.005

    Article  CAS  Google Scholar 

  15. Szummer A, Janik-Czachor M, Molnár Á et al (2001) Effect of hydrogenation under high pressure on the structure and catalytic properties of Cu-Zr amorphous alloys. J Mol Catal A Chem 176:205–212. https://doi.org/10.1016/S1381-1169(01)00259-X

    Article  CAS  Google Scholar 

  16. Sudhakar M, Naresh G, Rambabu G et al (2016) Crude bio-glycerol as a hydrogen source for the selective hydrogenation of aromatic nitro compounds over Ru/MgLaO catalyst. Catal Commun 74:91–94

    Article  CAS  Google Scholar 

  17. Huang M (2006) Polymer flooding experiment in transitional zone in Daqing oilfield. J Daqing Pet Inst 30:39–42

    Google Scholar 

  18. Syroezhko AM, Begak OY, Makurina GS (2004) Effect of various high-octane additives on antiknock quality of gasolines. Russ J Appl Chem 77:1002–1006. https://doi.org/10.1023/B:RJAC.0000044132.76469.b3

    Article  CAS  Google Scholar 

  19. Oudijk G (2010) The rise and fall of organometallic additives in automotive gasoline. Environ Foren 11:17–49

    Article  CAS  Google Scholar 

  20. Hoekman SK, Broch A (2016) MMT effects on gasoline vehicles: a literature review. SAE Int J Fuels Lubr. https://doi.org/10.4271/2016-01-9073

    Article  Google Scholar 

  21. Turáková M, Salmi T, Eränen K et al (2015) Liquid phase hydrogenation of nitrobenzene. Appl Catal A Gen 499:66–76. https://doi.org/10.1016/j.apcata.2015.04.002

    Article  CAS  Google Scholar 

  22. Wang J, Yuan Z, Nie R et al (2010) Hydrogenation of nitrobenzene to aniline over silica gel supported nickel catalysts. Ind Eng Chem Res 49:4664–4669. https://doi.org/10.1021/ie1002069

    Article  CAS  Google Scholar 

  23. Hong SY, Park SM (2005) Electrochemistry of conductive polymers 36. pH dependence of polyaniline conductivities studied by current-sensing atomic force microscopy. J Phys Chem B 109:9305–9310. https://doi.org/10.1021/jp050173g

    Article  CAS  PubMed  Google Scholar 

  24. Amer I, Brandt S (2018) Synthesis and characterization of Poly(p-phenylenediamine) and its derivatives using aluminium triflate as a co-catalyst. Cogent Eng 5:1–17. https://doi.org/10.1080/23311916.2018.1499701

    Article  Google Scholar 

  25. Kulagina MA, Simonov PA, Gerasimov EY et al (2017) To the nature of the support effect in palladium-catalyzed aqueous-phase hydrogenation of maleic acid. Colloids Surf A 526:29–39. https://doi.org/10.1016/j.colsurfa.2016.11.037

    Article  CAS  Google Scholar 

  26. Simonov PA, Romanenko AV, Likholobov VA (2014) Hydrogenation of ethyl p-nitrobenzoate on Pd/Sibunit catalysts. Solid Fuel Chem 48:364–370. https://doi.org/10.3103/S0361521914060068

    Article  CAS  Google Scholar 

  27. Jafar Tafreshi M, Masoomi Khanghah Z (2015) Infrared spectroscopy studies on sol-gel prepared alumina powders. Medziagotyra 21:28–31. https://doi.org/10.5755/j01.ms.21.1.4872

    Article  Google Scholar 

  28. Saikia BJ, Parthasarathy G (2010) Fourier transform infrared spectroscopic characterization of Kaolinite from Assam and Meghalaya, Northeastern India. J Mod Phys 1:206–210. https://doi.org/10.4236/jmp.2010.14031

    Article  CAS  Google Scholar 

  29. Parfenyuk EV, Antsiferova Y, Sotnikova N, Parfenyuk E (2015) Different effects of the immunomodulatory drug GMDP immobilized onto aminopropyl modified and unmodified mesoporous. Different effects of the immunomodulatory drug GMDP immobilized onto aminopropyl modified and unmodified mesoporous silica nanoparticle. BioMed Res Corp 2013:1–10. https://doi.org/10.1155/2013/924362

    Article  CAS  Google Scholar 

  30. Meyer B, Stroyer-Hansen T (1972) Infrared spectra of S4. J Phys Chem 76:3968–3969. https://doi.org/10.1021/j100670a013

    Article  CAS  Google Scholar 

  31. Hashemi M, Khodaei MM, Teymouri M et al (2016) Preparation of NiO nanocatalyst supported on MWCNTs and its application in reduction of nitrobenzene to aniline in liquid phase. Synth React Inorganic Met Nano-Metal Chem 46:959–967. https://doi.org/10.1080/15533174.2013.862646

    Article  CAS  Google Scholar 

  32. Al-Oweini R, El-Rassy H (2009) Synthesis and characterization by FTIR spectroscopy of silica aerogels prepared using several Si(OR)4 and R′′Si(OR′)3 precursors. J Mol Struct 919:140–145. https://doi.org/10.1016/j.molstruc.2008.08.025

    Article  CAS  Google Scholar 

  33. Kakizaki H, Aonuma C, Nakatani K (2007) Mass transfer of weak acid in nanometer-sized pores of octadecylsilyl-silica gel. J Colloid Interface Sci 307:166–171. https://doi.org/10.1016/j.jcis.2006.11.007

    Article  CAS  PubMed  Google Scholar 

  34. You C, Yu C, Yang X et al (2018) Double-shelled hollow mesoporous silica nanospheres as an acid–base bifunctional catalyst for cascade reactions. New J Chem 42:4095–4101. https://doi.org/10.1039/C7NJ04670G

    Article  CAS  Google Scholar 

  35. Cao J, **ao G, Xu X et al (2013) Study on carbonization of lignin by TG-FTIR and high-temperature carbonization reactor. Fuel Process Technol 106:41–47. https://doi.org/10.1111/j.1475-1305.1969.tb01607.x

    Article  CAS  Google Scholar 

  36. He X, Liu X, Nie B, Song D (2017) FTIR and Raman spectroscopy characterization of functional groups in various rank coals. Fuel 206:555–563. https://doi.org/10.1016/j.fuel.2017.05.101

    Article  CAS  Google Scholar 

  37. Desorption T, Equation DT (1995) Temperature-programmed desorption, pp 8812–8816

  38. Parapat RY, Saputra OHI, Ang AP et al (2014) Support effect in the preparation of supported metal catalysts via microemulsion. RSC Adv 4:50955–50963. https://doi.org/10.1039/c4ra10736e

    Article  CAS  Google Scholar 

  39. Radnik J (2017) X-ray photoelectron spectroscopy for investigation of heterogeneous catalytic process. Elsevier, Amsterdam

    Google Scholar 

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Acknowledgements

The work was funded by the Russian Science Foundation Grant No. 18-79-10157.

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Correspondence to Adele R. Latypova.

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Latypova, A.R., Tarasyuk, I.A., Filippov, D.V. et al. Synthesis, stability and activity of palladium supported over various inorganic matrices in the selective hydrogenation of nitroaniline. Reac Kinet Mech Cat 127, 741–755 (2019). https://doi.org/10.1007/s11144-019-01590-0

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