Skip to main content
SpringerLink
Log in

Selective Alkylation of Benzene with Methanol to Toluene and Xylene Over Sheet-Like ZSM-5 with Controllable b-Oriented Length

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Sheet-like ZSM-5 zeolites with varied b-axis thicknesses (92, 160, 264 and 407 nm, respectively) and equivalent Si/Al molar ratios (ca. 150) were prepared using urea as additive in the aluminosilicate gels, and studied with respect to their performance in benzene alkylation with methanol. The ZSM-5 samples have similar textural properties and acidic properties. Catalytic tests show that these catalysts exhibit comparable benzene conversions of ca. 64% at 400 °C and WHSV of 2 h−1. The correlation between the selectivity of toluene and xylene and the ZSM-5 crystal size in the b-axis can be established. As the b axis length is decreased from 407 to 92 nm, the selectivity to toluene and xylene increases obviously from 80.3 to 87.4%, which is attributed to enhanced diffusion property of ZSM-5 zeolite. This finding provides an alternative strategy to improve the selectivity of toluene and xylene in the alkylation of benzene with methanol over ZSM-5-based catalysts.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Gao K, Li S, Wang L, Wang W (2015) RSC Adv 5:45098–45105

    Article  ADS  CAS  Google Scholar 

  2. Liu C, Su J, Liu S, Zhou H, Yuan X, Ye Y, Wang Y, Jiao W, Zhang L, Lu Y, Wang Y, He H, Xie Z (2020) ACS Catal 10:15227–15237

    Article  CAS  Google Scholar 

  3. Hu H, Zhang Q, Cen J, Li X (2014) Catal Commun 57:129–133

    Article  ADS  CAS  Google Scholar 

  4. Hu H, Zhang Q, Cen J, Li X (2015) Catal Lett 145:715–722

    Article  CAS  Google Scholar 

  5. Hu H, Lyu J, Rui J, Cen J, Zhang Q, Wang Q, Han W, Li X (2016) Catal Sci Technol 6:2647–2652

    Article  CAS  Google Scholar 

  6. Qian J, Xiong G, Liu J, Liu C, Guo H (2019) Ind Eng Chem Res 58:9006–9016

    Article  CAS  Google Scholar 

  7. Odedairo T, Al-Khattaf S (2013) Catal Today 204:73–84

    Article  CAS  Google Scholar 

  8. Van der Mynsbrugge J, Visur M, Olsbye U, Beato P, Bjørgen M, Van Speybroeck V, Svelle S (2012) J Catal 292:201–212

    Article  Google Scholar 

  9. Lyu J, Hu H, Rui J, Zhang Q, Cen J, Han W, Wang Q, Chen X, Pan Z, Li X (2017) Chin Chem Lett 2:482–486

    Article  Google Scholar 

  10. Kokotailo GT, Lawton SL, Olson DH, Meier WM (1978) Nature 272:437–438

    Article  ADS  CAS  Google Scholar 

  11. Olson DH, Kokotailo GT, Lawton SL, Meier WM (1981) Crystal structure and structure-related properties of ZSM-5. J Phys Chem 85:2238–2243

    Article  CAS  Google Scholar 

  12. Liu C, Liu S, Zhou H, Su J, Jiao W, Zhang L, Wang Y, He H, Xie Z (2019) Appl Catal A 585:117206

    Article  Google Scholar 

  13. Wang C, Zhang L, Huang X, Zhu Y, Li G, Gu Q, Chen J, Ma L, Li X, He Q, Xu J, Sun Q, Song C, Peng M, Sun J, Ma D (2019) Nat Commun 10:4348

    Article  ADS  PubMed  PubMed Central  Google Scholar 

  14. Zhou J, Wang Y, Zou W, Wang C, Li L, Liu Z, Zheng A, Kong D, Yang W, Xie Z (2017) Ind Eng Chem Res 56:9310–9321

    Article  CAS  Google Scholar 

  15. Wang N, Sun W, Hou Y, Ge B, Hu L, Nie J, Qian W, Wei F (2018) J Catal 360:89–96

    Article  CAS  Google Scholar 

  16. Gu Z, Jiang D, Wang H, Cui X, Yan X (2010) J Phys Chem C 114:311–316

    Article  CAS  Google Scholar 

  17. Inagaki S, Shinoda S, Kaneko Y, Takechi K, Komatsu R, Tsuboi Y, Yamazaki H, Kondo JN, Kubota Y (2013) ACS Catal 3:74–78

    Article  CAS  Google Scholar 

  18. Kaeding WW (1988) J Catal 114:271–276

    Article  CAS  Google Scholar 

  19. Christensen CH, Johannsen K, Törnqvist E, Schmidt I, Topsøe H, Christensen CH (2007) Catal Today 128:117–122

    Article  CAS  Google Scholar 

  20. Milina M, Mitchell S, Trinidad ZD, Verboekend D, Pérez-Ramírez J (2012) Catal Sci Technol 2:759–766

    Article  CAS  Google Scholar 

  21. Abelló S, Bonilla A, Pérez-Ramírez J (2009) Appl Catal A 364:191–198

    Article  Google Scholar 

  22. Shan Z, Wang H, Meng X, Liu S, Wang L, Wang C, Li F, Lewis JP, Xiao F (2010) Chem Commun 47:1048–1050

    Article  Google Scholar 

  23. Chen X, Yan W, Shen W, Yu J, Cao X, Xu R (2007) Micropor Mesopor Mater 104:296–304

    Article  CAS  Google Scholar 

  24. Liu Y, Zhou X, Pang X, Jin Y, Meng X, Zheng X, Gao X, Xiao F (2013) ChemCatChem 5:1517–1523

    Article  CAS  Google Scholar 

  25. Liu Y, Li Y, Yang W (2010) J Am Chem Soc 132:1768–1769

    Article  CAS  PubMed  Google Scholar 

  26. Liu Y, Qiang W, Ji T, Zhang M, Li M, Lu J, Liu Y (2020) Sci Adv 6:eaay5993

    Article  ADS  CAS  PubMed  PubMed Central  Google Scholar 

  27. Dai W, Kouvatas C, Tai W, Wu G, Guan N, Li L, Valtchev V (2021) J Am Chem Soc 143:1993–2004

    Article  CAS  PubMed  Google Scholar 

  28. Zhang J, Ren L, Zhou A, Li W, Shang S, Liu Y, Jia Z, Liu W, Zhang A, Guo X, Song C (2022) Chem Mater 34:3217–3226

    Article  CAS  Google Scholar 

  29. Qureshi BA, Lan X, Arslan MT, Wang T (2019) Ind Eng Chem Res 58:12611–12622

    Article  CAS  Google Scholar 

  30. Ali B, Lan X, Arslan MT, Gilani SZA, Wang H, Wang T (2020) J Ind Eng Chem 88:127–136

    Article  CAS  Google Scholar 

  31. Yan Z, Chen D, Huang L, Liu J, Fu H, Xiao Y, Li S (2022) Micropor Mesopor Mater 337:111926

    Article  CAS  Google Scholar 

  32. Zhang J, Zhou A, Gawande K, Li G, Shang S, Dai C, Fan W, Han Y, Song C, Ren L, Zhang A, Guo X (2023) ACS Catal 13:3794–3805

    Article  CAS  Google Scholar 

  33. Yang J, Gong K, Miao D, Jiao F, Pan X, Meng X, Xiao F, Bao X (2019) J Energy Chem 35:44–48

    Article  CAS  Google Scholar 

  34. Emeis CA (1993) J Catal 141:347–354

    Article  CAS  Google Scholar 

  35. Yang F, Zhong J, Liu X, Zhu X (2018) Appl Energy 226:22–30

    Article  ADS  CAS  Google Scholar 

  36. Shishido T, Hattori H (1996) J Catal 161:194–197

    Article  CAS  Google Scholar 

  37. Yue Y, Gu L, Zhou Y, Liu H, Yuan P, Zhu H, Bai Z, Bao X (2017) Ind Eng Chem Res 56:10069–10077

    Article  CAS  Google Scholar 

  38. Corma A (2003) J Catal 216:298–312

    Article  CAS  Google Scholar 

  39. Nagy JB, Gabelica Z, Debras G, Derouane EG, Gilson JP, Jacobs PA (1984) Zeolites 4:133–139

    Article  CAS  Google Scholar 

  40. Deng F, Du Y, Ye C, Wang J, Ding T, Li H (1995) J Phys Chem 99:15208–15214

    Article  CAS  Google Scholar 

  41. Blasco T, Corma A, Martínez-Triguero J (2006) J Catal 237:267–277

    Article  CAS  Google Scholar 

  42. Fyfe CA, Gobbi GC, Kennedy GJ (1984) J Phys Chem 88:3248–3253

    Article  CAS  Google Scholar 

  43. Wu Q, Liu X, Zhu L, Ding L, Gao P, Wang X, Pan S, Bian C, Meng X, Xu J, Deng F, Maurer S, Müller U, Xiao F (2015) J Am Chem Soc 137:1052–1055

    Article  CAS  PubMed  Google Scholar 

  44. Zhu X, Wu L, Magusin P, Mezari B, Hensen E (2015) J Catal 327:10–21

    Article  CAS  Google Scholar 

  45. Wu D, Yu X, Chen X, Yu G, Zhang K, Qiu M, Xue W, Yang C, Liu Z, Sun Y (2019) Chemsuschem 12:3871–3877

    Article  CAS  PubMed  Google Scholar 

  46. Soghrati E, Ong TKC, Poh CK, Kawi S, Borgna A (2018) Appl Catal B 235:130–142

    Article  CAS  Google Scholar 

  47. Nie Y, Shang S, Xu X, Hua W, Yue Y, Gao Z (2012) Appl Catal A 433–434:69–74

    Article  Google Scholar 

  48. van Donk S, Bitter JH, Verberckmoes A, Versluijs-Helder M, Broersma A, de Jong KP (2004) Angew Chem Int Ed 44:1360–1363

    Article  Google Scholar 

  49. Groen JC, Zhu W, Brouwer S, Huynink SJ, Kapteijn F, Moulijn JA, Pérez-Ramírez J (2007) J Am Chem Soc 129:355–360

    Article  CAS  PubMed  Google Scholar 

  50. Zhang H, Zhang H, Zhao Y, Shi Z, Zhang Y, Tang Y (2017) Chem Mater 29:9247–9255

    Article  CAS  Google Scholar 

  51. Zhao Y, Wang L, Ye Z, Zhang H, Xie S, Zhang Y, Tang Y (2019) Cryst Growth Des 19:6192–6198

    Article  CAS  Google Scholar 

  52. Kim MY, Lee K, Choi M (2014) J Catal 319:232–238

    Article  CAS  Google Scholar 

  53. Anderson JR, Mole T, Christov V (1980) J Catal 61:477–484

    Article  CAS  Google Scholar 

  54. Svelle S, Visur M, Olsbye U, Saepurahman S, Bjørgen M (2011) Top Catal 54:897–906

    Article  CAS  Google Scholar 

  55. Adebajo MO, Long MA (2003) Catal Commun 4:71–76

    Article  CAS  Google Scholar 

  56. Zhao Y, Tan W, Wu H, Zhang A, Liu M, Li G, Wang X, Song C, Guo X (2011) Catal Today 160:179–183

    Article  CAS  Google Scholar 

  57. Zhu Z, Chen Q, Xie Z, Yang W, Li C (2006) Micropor Mesopor Mater 88:16–21

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (Grant Nos. 22072027 and 91645201), the Science and Technology Commission of Shanghai Municipality (Grant No. 13DZ2275200), and the Shanghai Research Institute of Petrochemical Technology SINOPEC.

Author information

Authors and Affiliations

  1. Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Department of Chemistry, Fudan University, Shanghai, 200438, People’s Republic of China

    Shu Ren, Chao Tian, Yinghong Yue, Weiming Hua & Zi Gao

  2. State Key Laboratory of Green Chemical Engineering and Industrial Catalysis, SINOPEC Shanghai Research Institute of Petrochemical Technology Co., Ltd., Shanghai, 201208, People’s Republic of China

    Shu Ren & Wei Zou

Authors
  1. Shu Ren
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chao Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yinghong Yue
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wei Zou
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Weiming Hua
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Zi Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

SR: investigation, data curation, writing—original draft. CT: investigation, data curation. YY: methodology, formal analysis. WZ: methodology, formal analysis. WH: conceptualization, supervision, writing—review & editing, project administration. ZG: validation, formal analysis.

Corresponding author

Correspondence to Weiming Hua.

Ethics declarations

Competing Interests

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ren, S., Tian, C., Yue, Y. et al. Selective Alkylation of Benzene with Methanol to Toluene and Xylene Over Sheet-Like ZSM-5 with Controllable b-Oriented Length. Catal Lett 154, 858–867 (2024). https://doi.org/10.1007/s10562-023-04352-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-023-04352-9

Keywords

Search

Navigation