Advertisement

Catalysis Letters

, Volume 126, Issue 3–4, pp 333–340 | Cite as

Alkylation of Phenol with tert-Butanol Catalyzed by Mesoporous Material with Enhanced Acidity Synthesized from Zeolite MCM-22

  • Ke Song
  • Jingqi Guan
  • Shujie Wu
  • Ying Yang
  • Bo Liu
  • Qiubin Kan
Article

Abstract

Using zeolite MCM-22 as source and cetyltrimethylammonium bromide (CTAB) as template, mesoporous material denoted as M-MCM-22 with enhanced acidity has been synthesized and characterized by XPD, FT-IR, N2 adsorption–desorption, 27Al-MAS NMR, IR spectra of pyridine adsorption, and NH3-TPD techniques, etc. The catalytic performance of M-MCM-22 was tested in alkylation of phenol with tert-butanol, indicating that M-MCM-22 showed highly and steadily catalytic properties. The highest conversion of phenol could be achieved at 418 K, while the highest selectivity to 2, 4-di-TBP was obtained at 398 K. It is found that high temperature is advantageous to form 4-TBP, whereas low weight hourly space velocity (WHSV/h−1) is helpful for both conversion of phenol and selectivity to 2,4-DTBP. It is also shown that high ratio of tert-butanol/phenol is beneficial for obtaining high conversion of phenol and selectivity to 2,4-di-TBP.

Keywords

Mesoporous MCM-22 Enhanced acidity Butylation Phenol 

Notes

Acknowledgments

We thank the National Basic Research Program of China (2004CB217804) and the National Natural Science Foundation of China (20673046) for financial support of this work.

References

  1. 1.
    Sartori G, Bigi F, Casiraghi G, Carnati G, Chiesi L, Arduini A (1985) Chem Ind 22:762–763Google Scholar
  2. 2.
    Carlton AA (1948) J Org Chem 13:120CrossRefGoogle Scholar
  3. 3.
    Chandra KG, Sharma MM (1993) Catal Lett 19:309–317CrossRefGoogle Scholar
  4. 4.
    Sartori G, Bigi F, Casiraghi G, Casnati G, Chiesi L, Arduini A (1985) Chem Ind (London) 22:762–763Google Scholar
  5. 5.
    Krishnan AV, Ojha K, Pradhan NC (2002) Org Process Res Dev 6:132–137CrossRefGoogle Scholar
  6. 6.
    Zhang K, Zhang H, Xua G, Xiang S, Xu D, Liu S, Li H (2001) Appl Catal A: Gen 207:183–190CrossRefGoogle Scholar
  7. 7.
    Zhang K, Huang C, Zhang H, Xiang S, Liu S, Xu D, Li H (1998) Appl Catal A: Gen 166:89–95CrossRefGoogle Scholar
  8. 8.
    Anand R, Maheswari R, Gore KU, Tope BB (2003) J Mol Catal A 193:251–257CrossRefGoogle Scholar
  9. 9.
    Dumitriu E, Hulea V (2003) J Catal 218:249–257CrossRefGoogle Scholar
  10. 10.
    Vinu A, Devassy BM, Halligudi SB, Bohlmann W, Hartmann M (2005) Appl Catal A: Gen 281:207–213CrossRefGoogle Scholar
  11. 11.
    Dapurkar SE, Selvam P (2003) Appl Catal A: Gen 254:239–249CrossRefGoogle Scholar
  12. 12.
    Yadav GD, Pathre GS (2006) Appl Catal A: Gen 297:237–246CrossRefGoogle Scholar
  13. 13.
    Sakthivel A, Badamali SK, Selvam P (2000) Micropor Mesopor Mater 39:457–463CrossRefGoogle Scholar
  14. 14.
    Anand R, Maheswari R, Hanefeld U (2006) J Catal 242:82–91CrossRefGoogle Scholar
  15. 15.
    Huang J, Li G, Wu S, Wang H, Xing L, Song K, Wu T, Kan Q (2005) J Mater Chem 15:1055–1060CrossRefGoogle Scholar
  16. 16.
    Huang J, Li G, Wu S, Wang H, Xing L, Song K, Wu T, Kan Q (2006) Micropor Mesopor Mater 96:21–28CrossRefGoogle Scholar
  17. 17.
    Huang J, Li G, Wu S, Wang H, Xing L, Song K, Wu T, Kan Q (2006) J Catal 242:82–91CrossRefGoogle Scholar
  18. 18.
    Knop A, Pilato LA (1985) Phenolic resin chemistry Springer, BerlinGoogle Scholar
  19. 19.
    Kolka AJ, Napolitano JP, Elike GG (1956) J Org Chem 21:712–713CrossRefGoogle Scholar
  20. 20.
    Corma A (1997) Chem Rev 97:2373–2419CrossRefGoogle Scholar
  21. 21.
    Kloetstra KR, van Bekkum H, Jansen JC (1997) Chem Commun 2281–2282Google Scholar
  22. 22.
    Karlsson A, Stocker M, Schmidt R (1999) Micropor Mesopor Mater 27:181–192CrossRefGoogle Scholar
  23. 23.
    Huang L, Guo W, Deng P, Xue Z, Li Q (2000) J. Phys Chem B 104:2817–2823CrossRefGoogle Scholar
  24. 24.
    Xia Y, Mokaya R (2004) J Mater Chem 14:863–870CrossRefGoogle Scholar
  25. 25.
    Guo W, Xiong C, Huang L, Li Q (2001) J Mater Chem 11:1886–1890CrossRefGoogle Scholar
  26. 26.
    Guo W, Huang L, Deng P, Xue Z, Li Q (2001) Micropor Mesopor Mater 44:427–434CrossRefGoogle Scholar
  27. 27.
    Liu Y, Zhang W, Pinnavaia TJ (2000) J Am Chem Soc 122:8791CrossRefGoogle Scholar
  28. 28.
    Liu Y, Zhang W, Pinnavaia TJ (2001) Angew Chem In Ed 40:1255–1258CrossRefGoogle Scholar
  29. 29.
    Liu Y, Pinnavaia J (2002) Chem Mater 14:3–5CrossRefGoogle Scholar
  30. 30.
    Zhang ZT, Han Y, Zhu L, Wang R, Yu Y, Qiu S, Zhao D, Xiao F (2001) Angew Chem Int Ed 40:1258–1262CrossRefGoogle Scholar
  31. 31.
    Zhang ZT, Han Y, Xiao F, Qiu S, Zhu L, Wang R, Yu Y, Zhang Z, Zou B, Wang Y, Sun H, Zhao D, Wei Y (2001) J Am Chem Soc 123:5014–5021CrossRefGoogle Scholar
  32. 32.
    Wu P, Kan Q, Wang D, Xing H, Jia M, Wu T (2005) Catal Commun 6:449–453CrossRefGoogle Scholar
  33. 33.
    Ordomsky VV, Murzin VY, Monakhova YV, Zubavichus YV, Knyazeva EE, Nesterenko NS, Ivanova II (2007) Micropor Mesopor Mater 105:101–110CrossRefGoogle Scholar
  34. 34.
    Lippens BC, De Boer JH (1965) J Catal 4:319–323CrossRefGoogle Scholar
  35. 35.
    Liu Y, Zhang W, Pinnavaia TJ (2001) Angew Chem Int Ed 40:1255–1258CrossRefGoogle Scholar
  36. 36.
    Jacobs PA, Derouane EG, Weitkamp J (1981) J Chem Soc Chem Commun 591–593Google Scholar
  37. 37.
    Jansen JC, Gaag FJV, Bekkum HV (1984) Zeolites 4:369CrossRefGoogle Scholar
  38. 38.
    Schoeman BJ (1997) Stud Surf Sci Catal 105:647–654CrossRefGoogle Scholar
  39. 39.
    Kirschhock CEA, Ravishankar R, Verspeurt F, Grobet PJ, Jacobs PA, Martens JA (1999) J Phys Chem B 103:4965–4971CrossRefGoogle Scholar
  40. 40.
    Lawton SL, Fung AS, Kennedy GJ, Alemany LB, Chang CD, Hatzikos GH, Lissy DN, Rubin MK, Timken H-KC, Steuernagel S, Woessner DE (1996) J Phys Chem 100:3788–3798CrossRefGoogle Scholar
  41. 41.
    Parry EP (1963) J Catal 2:371CrossRefGoogle Scholar
  42. 42.
    Yamamoto T, Tanaka T, Funabiki T, Yoshida S (1998) J Phys Chem B 102:5830–5839CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2008

Authors and Affiliations

  • Ke Song
    • 1
  • Jingqi Guan
    • 1
  • Shujie Wu
    • 1
  • Ying Yang
    • 1
  • Bo Liu
    • 1
  • Qiubin Kan
    • 1
  1. 1.College of ChemistryJilin UniversityChangchunPeople’s Republic of China

Personalised recommendations