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Journal of Materials Science

, Volume 55, Issue 4, pp 1614–1626 | Cite as

Benzene–toluene–xylene (BTX) from p-cresol by hydrodeoxygenation over nickel phosphide catalysts with different supports

  • Liuyi Pan
  • Yulong He
  • Menglong Niu
  • Yong Dan
  • Wenhong LiEmail author
Energy materials
  • 63 Downloads

Abstract

Ni2P catalysts supported on different supports, such as SiO2 from different sources, Al2O3, TiO2 and ZrO2 were prepared for the hydrodeoxygenation of p-cresol (monocyclic phenol model in coal tar). The reaction was carried out on a fixed-bed reactor at a temperature of 330–390 °C under 2 MPa. The order of conversion of p-cresol was as follows: Ni2P/SiO2-2 > Ni2P/SiO2-3 > Ni2P/SiO2-1 > Ni2P/Al2O3 > Ni2P/ZrO2 > Ni2P/TiO2. Ni2P/SiO2-3 shown higher DDO path selectivity, resulting in the conversion of p-cresol of 93% and a selectivity of 72.6% for BTX products under the reaction temperature of 370 °C with LHSV of 0.5 h−1. This catalyst was also used for the hydrodeoxygenation of the crude phenolic mixture extracted from coal tar, which shown that the phenol deoxidation rate was 87.6% and the BTX product selectivity was 73.7% by GC–MS.

Notes

Acknowledgements

We gratefully acknowledge the financial support of the Key Research and Development Program of Shaanxi (2018ZDXM-GY-161 and 2018GY-087).

References

  1. 1.
    Meng H, Ge C-T, Ren N-N, Ma W-Y, Lu Y-Z, Li C-X (2013) Complex extraction of phenol and cresol from model coal tar with polyols, ethanol amines, and ionic liquids thereof. Ind Eng Chem Res 53:355–362Google Scholar
  2. 2.
    Zhu L, Deng Y, Chen J, Zhang J (2011) Adsorption of phenol from water by N-butylimidazolium functionalized strongly basic anion exchange resin. J Colloid Interface Sci 364:462–468Google Scholar
  3. 3.
    Niu M, Sun X, Gao R, Li D, Cui W, Li W (2016) Effect of dephenolization on low-temperature coal tar hydrogenation to produce fuel oil. Energy Fuels 30:10215–10221Google Scholar
  4. 4.
    Zhao HY, Li D, Bui P, Oyama ST (2011) Hydrodeoxygenation of guaiacol as model compound for pyrolysis oil on transition metal phosphide hydroprocessing catalysts. Appl Catal A Gen 391:305–310Google Scholar
  5. 5.
    Bui VN, Laurenti D, Afanasiev P, Geantet C (2011) Hydrodeoxygenation of guaiacol with CoMo catalysts. Part I: promoting effect of cobalt on HDO selectivity and activity. Appl Catal B Environ 101:239–245Google Scholar
  6. 6.
    Xu X, Jiang E (2017) “BTX” from guaiacol HDO under atmospheric pressure: effect of support and carbon deposition. Energy Fuels 31:2855–2864Google Scholar
  7. 7.
    Wu S-K, Lai P-C, Lin Y-C, Wan H-P, Lee H-T, Chang Y-H (2013) Atmospheric hydrodeoxygenation of guaiacol over alumina-, zirconia-, and silica-supported nickel phosphide catalysts. ACS Sustain Chem Eng 1:349–358Google Scholar
  8. 8.
    Moon J-S, Kim E-G, Lee Y-K (2014) Active sites of Ni2P/SiO2 catalyst for hydrodeoxygenation of guaiacol: a joint XAFS and DFT study. J Catal 311:144–152Google Scholar
  9. 9.
    Zhang X, Long J, Kong W, Zhang Q, Chen L, Wang T, Ma L, Li Y (2014) Catalytic upgrading of bio-oil over Ni-based catalysts supported on mixed oxides. Energy Fuels 28:2562–2570Google Scholar
  10. 10.
    Teles CA, Rabelo-Neto RC, de Lima JR, Mattos LV, Resasco DE, Noronha FB (2016) The effect of metal type on hydrodeoxygenation of phenol over silica supported catalysts. Catal Lett 146:1848–1857Google Scholar
  11. 11.
    Ansaloni S, Russo N, Pirone R (2017) Hydrodeoxygenation of guaiacol over molybdenum-based catalysts: the effect of support and the nature of the active site. Can J Chem Eng 95:1730–1744Google Scholar
  12. 12.
    Anaya F, Zhang L, Tan Q, Resasco DE (2015) Tuning the acid–metal balance in Pd/ and Pt/zeolite catalysts for the hydroalkylation of m-cresol. J Catal 328:173–185Google Scholar
  13. 13.
    de Souza PM, Rabelo-Neto RC, Borges LEP, Jacobs G, Davis BH, Sooknoi T, Resasco DE, Noronha FB (2015) Role of Keto intermediates in the hydrodeoxygenation of phenol over Pd on oxophilic supports. ACS Catal 5:1318–1329Google Scholar
  14. 14.
    Nie L, de Souza PM, Noronha FB, An W, Sooknoi T, Resasco DE (2014) Selective conversion of m-cresol to toluene over bimetallic Ni–Fe catalysts. J Mol Catal A: Chem 388–389:47–55Google Scholar
  15. 15.
    Yang F, Liu D, Wang H, Liu X, Han J, Ge Q, Zhu X (2017) Geometric and electronic effects of bimetallic Ni–Re catalysts for selective deoxygenation of m-cresol to toluene. J Catal 349:84–97Google Scholar
  16. 16.
    Sitthisa S, An W, Resasco DE (2011) Selective conversion of furfural to methylfuran over silica-supported NiFe bimetallic catalysts. J Catal 284:90–101Google Scholar
  17. 17.
    Li K, Wang R, Chen J (2011) Hydrodeoxygenation of anisole over silica-supported Ni2P, MoP, and NiMoP catalysts. Energy Fuels 25:854–863Google Scholar
  18. 18.
    Cecilia JA, Infantes-Molina A, Rodríguez-Castellón E, Jiménez-López A (2009) Dibenzothiophene hydrodesulfurization over cobalt phosphide catalysts prepared through a new synthetic approach: effect of the support. Appl Catal B Environ 92:100–113Google Scholar
  19. 19.
    Laurent E, Delmon B (1994) Influence of water in the deactivation of a sulfided NiMoγ-Al2O3 catalyst during hydrodeoxygenation. J Catal 146:281–291Google Scholar
  20. 20.
    Popov A, Kondratieva E, Goupil JM, Mariey L, Bazin P, Gilson J-P, Travert A, Maugé F (2010) Bio-oils hydrodeoxygenation: adsorption of phenolic molecules on oxidic catalyst supports. J Phys Chem C 114:15661–15670Google Scholar
  21. 21.
    Yang Y, Gilbert A, Xu C (2009) Hydrodeoxygenation of bio-crude in supercritical hexane with sulfided CoMo and CoMoP catalysts supported on MgO: a model compound study using phenol. Appl Catal A Gen 360:242–249Google Scholar
  22. 22.
    Berenguer A, Bennett JA, Hunns J, Moreno I, Coronado JM, Lee AF, Pizarro P, Wilson K, Serrano DP (2018) Catalytic hydrodeoxygenation of m-cresol over Ni2P/hierarchical ZSM-5. Catal Today 304:72–79Google Scholar
  23. 23.
    Tyrone Ghampson I, Sepúlveda C, Garcia R, García Fierro JL, Escalona N, DeSisto WJ (2012) Comparison of alumina- and SBA-15-supported molybdenum nitride catalysts for hydrodeoxygenation of guaiacol. Appl Catal A Gen 435–436:51–60Google Scholar
  24. 24.
    Xu X, Jiang E, Li Z, Sun Z (2018) BTX from anisole by hydrodeoxygenation and transalkylation at ambient pressure with zeolite catalysts. Fuel 221:440–446Google Scholar
  25. 25.
    Sankaranarayanan TM, Berenguer A, Ochoa-Hernández C, Moreno I, Jana P, Coronado JM, Serrano DP, Pizarro P (2015) Hydrodeoxygenation of anisole as bio-oil model compound over supported Ni and Co catalysts: effect of metal and support properties. Catal Today 243:163–172Google Scholar
  26. 26.
    Zhang X, Long J, Kong W, Zhang Q, Chen L, Wang T, Ma L, Li Y (2014) Catalytic upgrading of bio-oil over Ni-Based catalysts supported on mixed oxides. Energy Fuel 28:2562–2570Google Scholar
  27. 27.
    Romero Y, Richard F, Brunet S (2010) Hydrodeoxygenation of 2-ethylphenol as a model compound of bio-crude over sulfided Mo-based catalysts: promoting effect and reaction mechanism. Appl Catal B Environ 98:213–223Google Scholar
  28. 28.
    Mortensen P, Grunwaldt J-D, Jensen P, Jensen A (2013) Screening of catalysts for hydrodeoxygenation of phenol as a model compound for bio-oil. ACS Catal 3:1774–1785Google Scholar
  29. 29.
    Oyama ST, Onkawa T, Takagaki A, Kikuchi R, Hosokai S, Suzuki Y, Bando KK (2015) Production of phenol and cresol from guaiacol on nickel phosphide catalysts supported on acidic supports. Top Catal 58:201–210Google Scholar
  30. 30.
    Watanabe S, Ma X, Song C (2009) Characterization of structural and surface properties of nanocrystalline TiO2–CeO2 mixed oxides by XRD, XPS, TPR, and TPD. J Phys Chem 113:14249–14257Google Scholar
  31. 31.
    Takahashi N, Suda A, Hachisuka I, Sugiura M, Sobukawa H, Shinjoh H (2007) Sulfur durability of NOx storage and reduction catalyst with supports of TiO2, ZrO2 and ZrO2–TiO2 mixed oxides. Appl Catal B Environ 72:187–195Google Scholar
  32. 32.
    Sawhill S (2003) Thiophene hydrodesulfurization over supported nickel phosphide catalysts. J Catal 215:208–219Google Scholar
  33. 33.
    Cui W, Zheng H, Niu M, Zhang S, Li D, Qiao J, Li W (2016) Product compositions from catalytic hydroprocessing of low temperature coal tar distillate over three commercial catalysts. React Kinet Mech Catal 119:491–509Google Scholar
  34. 34.
    Peyrovi MH, Rostamikia T, Parsafard N (2018) Competitive hydrogenation of benzene in reformate gasoline over Ni supported on SiO2, SiO2–Al2O3, and Al2O3 catalysts: influence of support nature. Energy Fuels 32:11432–11439Google Scholar
  35. 35.
    Cecilia JA, Infantes-Molina A, Rodríguez-Castellón E, Jiménez-López A (2009) The influence of the support on the formation of Ni2P based catalysts by a new synthetic approach. Study of the catalytic activity in the hydrodesulfurization of dibenzothiophene. J Phys Chem C 113:17032–17044Google Scholar
  36. 36.
    Yang Y, Chen J, Shi H (2013) Deoxygenation of methyl laurate as a model compound to hydrocarbons on Ni2P/SiO2, Ni2P/MCM-41, and Ni2P/SBA-15 catalysts with different dispersions. Energy Fuel 27:3400–3409Google Scholar
  37. 37.
    Rodriguez JA, Hanson JC, Frenkel AI, Kim JY, Pérez M (2002) Experimental and theoretical studies on the reaction of H(2) with NiO: role of O vacancies and mechanism for oxide reduction. J Am Chem Soc 124:346–354Google Scholar
  38. 38.
    Van Veen JAR, Hendriks PAJM, Andrea RR (1990) Chemistry of phosphomolybdate adsorption on alumina surfaces. 2. The molybdate/phosphated alumina and phosphomolybdate/alumina systems. J Phys Chem 94:5282–5285Google Scholar
  39. 39.
    Abu II, Smith KJ (2007) HDN and HDS of model compounds and light gas oil derived from Athabasca bitumen using supported metal phosphide catalysts. Appl Catal A Gen 328:58–67Google Scholar
  40. 40.
    Kim Y-S, Lee G-N, Yun Y-K (2014) Novel Ni2P/zeolite catalysts for naphthalene hydrocracking to BTX. Catal Commun 45:133–138Google Scholar
  41. 41.
    Zarchin R, Rabaev M, Vidruk-Nehemya R, Landau MV, Herskowitz M (2015) Hydroprocessing of soybean oil on nickel-phosphide supported catalysts. Fuel 139:684–691Google Scholar
  42. 42.
    Sawhill S, Layman K, Vanwyk D, Engelhard M, Wang C, Bussell M (2005) Thiophene hydrodesulfurization over nickel phosphide catalysts: effect of the precursor composition and support. J Catal 231:300–313Google Scholar
  43. 43.
    Decanio EC, Edwards JC, Scalzo TR, Storm DA, Bruno JW (1991) FT-IR and solid-state NMR investigation of phosphorus promoted hydrotreating catalyst precursors. J Catal 132:498–511Google Scholar
  44. 44.
    Song R, Luo B, Geng J, Song D (2018) Photothermocatalytic hydrogen evolution over Ni2P/TiO2 for full-spectrum solar energy conversion. Ind Eng Chem Res 57:7846–7854Google Scholar
  45. 45.
    Gonçalves VOO, Brunet S, Richard F (2016) Hydrodeoxygenation of cresols over Mo/Al2O3 and CoMo/Al2O3 sulfided catalysts. Catal Lett 146:1562–1573Google Scholar
  46. 46.
    Furimsky E (2000) Catalytic hydrodeoxygenation. Appl Catal A Gen 199:147–190Google Scholar
  47. 47.
    Oyama S, Lee Y (2008) The active site of nickel phosphide catalysts for the hydrodesulfurization of 4,6-DMDBT. J Catal 258:393–400Google Scholar
  48. 48.
    Lee Y-K, Seo H-R, Cho K-S, Kim S-H (2010) Effects of phosphorus precursor on structure and activity of Ni2P/SiO2 hydrotreating catalysts: EXAFS studies. J Korean Phys Soc 56:2083–2087Google Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.School of Chemical EngineeringNorthwest UniversityXi’anPeople’s Republic of China
  2. 2.College of Chemistry and Chemical EngineeringBaoji University of Arts and SciencesBaojiPeople’s Republic of China
  3. 3.College of Chemistry and Chemical EngineeringXi’an Shiyou UniversityXi’anPeople’s Republic of China

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