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Catalytic Mononitration of Phenol Using iso-Propyl Nitrate Over Zeolite Catalysts

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Abstract

Mononitration of phenol was investigated using iso-propyl nitrate as a nitrating agent over various zeolite catalysts under different reaction conditions. Zeolite Hβ with a low Si/Al ratio (12.5) was found to be an active catalyst for nitration of phenol under reflux conditions in dichloroethane, producing 2- and 4-nitrophenols in a ratio of around 1:1. However, zeolites H-mordenite, HY and Hβ (with high Si/Al ratio—150 or 300) gave 2-nitrophenol as the major product (ortho/para ratio = ca. 2–3).

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References

  1. Schofield K (1980) Aromatic nitration. Cambridge University Press, Cambridge

    Google Scholar 

  2. Olah GA, Malhotra R, Narang SC (1989) Nitration: methods and mechanisms. VCH, New York

    Google Scholar 

  3. Coombes RG, Golding JG, Hadjigeorgiou P (1979) J Chem Soc Perkin Trans 2:1451

    Google Scholar 

  4. Clark JH (2002) Acc Chem Res 35:791

    Article  CAS  Google Scholar 

  5. Clark JH (ed) (1994) Catalysis of organic reactions using supported inorganic reagents. VCH, New York

    Google Scholar 

  6. Delaude L, Laszlo P, Smith K (1993) Acc Chem Res 26:607

    Article  CAS  Google Scholar 

  7. Smith K (1992) In: Yoshida Z, Ohshiro Y (eds) New aspects of organic synthesis II. Kadonsha, Tokyo; VCH, Weinheim, p 43

  8. Butters M (1992) In: Smith K (ed) Solid supports and catalysts in organic synthesis. Ellis Horwood, Chichester, p 130

    Google Scholar 

  9. Smith K (1991) In: Scaros MG, Prunier ML (eds) Catalysis of organic reactions. Marcel Dekker, New York, p 91

    Google Scholar 

  10. Smith K, El-Hiti GA (2004) Curr Org Synth 1:253

    Article  CAS  Google Scholar 

  11. Smith K, El-Hiti GA (2006) Curr Org Chem 10:1603

    Article  CAS  Google Scholar 

  12. Smith K, Roberts SD, El-Hiti GA (2003) Org Biomol Chem 1:1552

    Article  CAS  Google Scholar 

  13. Smith K, El-Hiti GA, Jayne AJ, Butters M (2003) Org Biomol Chem 1:1560

    Article  CAS  Google Scholar 

  14. Smith K, El-Hiti GA, Jayne AJ, Butters M (2003) Org Biomol Chem 1:2321

    Article  CAS  Google Scholar 

  15. Smith K, Ewart GM, El-Hiti GA, Randles KR (2004) Org Biomol Chem 2:3150

    Article  CAS  Google Scholar 

  16. Smith K, El-Hiti GA, Hammond MEW, Bahzad D, Li Z, Siquet C (2000) J Chem Soc Perkin Trans 1:2745

    Article  Google Scholar 

  17. Smith K, Butters M, Paget WE, Goubet D, Fromentin E, Nay B (1999) Green Chem 1:83

    Article  CAS  Google Scholar 

  18. Smith K, Musson A, DeBoos GA (1998) J Org Chem 63:8448

    Article  CAS  Google Scholar 

  19. Smith K, Gibbins T, Millar RW, Claridge RP (2000) J Chem Soc Perkin Trans 1:2753

    Article  Google Scholar 

  20. Smith K, Almeer S, Black SJ (2000) Chem Commun 1571

  21. Smith K, Almeer S, Peters C (2001)Chem Commun 2748

  22. Smith K, Almeer S, Black SJ, Peters C (2002) J Mater Chem 12:3285

    Article  CAS  Google Scholar 

  23. Rodrigues JAR, de Oliveira Filho AP, Moran PJS, Custódio R (1999) Tetrahedron 55:6733

    Article  CAS  Google Scholar 

  24. Yin W-P, Shi M (2005) Tetrahedron 61:10861

    Article  CAS  Google Scholar 

  25. Gigante B, Prazeres AO, Marcelo-Curto MJ, Cornélis A, Laszlo P (1995) J Org Chem 60:3445

    Article  CAS  Google Scholar 

  26. Milczak T, Jacniacki J, Zawadzki J, Malesa M, Skupiński W (2001) Synth Commun 31:173

    Article  CAS  Google Scholar 

  27. Heravi MM, Benmorad T, Bakhtiari K, Bamoharram FF, Oskooie HH (2007) J Mol Catal A Chem 264:318

    Article  CAS  Google Scholar 

  28. Mallick S, Parida KM (2007) Catal Commun 8:1487

    Article  CAS  Google Scholar 

  29. Parida KM, Rath D (2006) J Mol Catal A Chem 258:381

    Article  CAS  Google Scholar 

  30. Riego JM, Sedin Z, Zaldlvar J-M, Marzianot NC, Tortato C (1996) Tetrahedron Lett 37:513

    Article  CAS  Google Scholar 

  31. Zolfigol MA, Ghaemi E, Madrakian E (2001) Molecules 6:614

    Article  CAS  Google Scholar 

  32. Sunajadevi KR, Sugunan S (2005) Catal Commun 6:611

    Article  CAS  Google Scholar 

  33. Sunajadevi KR, Sugunan S (2006) Mater Lett 60:3813

    Article  CAS  Google Scholar 

  34. Khder AS, Ahmed AI (2009) Appl Catal A 354:153

    Article  CAS  Google Scholar 

  35. Dagade SP, Kadam VS, Dongare MK (2002) Catal Commun 3:67

    Article  CAS  Google Scholar 

  36. Esakkidurai T, Pitchumani K (2002) J Mol Catal A Chem 185:305

    Article  CAS  Google Scholar 

  37. Taylor R (1990) Electrophilic aromatic substitution. Wiley, Chichester, p 263

    Google Scholar 

  38. Vione D, Belmondo S, Carnino L (2004) Environ Chem Lett 2:135

    Article  CAS  Google Scholar 

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Acknowledgments

We thank Cardiff University and the Saudi Government for financial support.

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Correspondence to Keith Smith.

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Smith, K., Ajarim, M.D., El-Hiti, G.A. et al. Catalytic Mononitration of Phenol Using iso-Propyl Nitrate Over Zeolite Catalysts. Top Catal 52, 1696–1700 (2009). https://doi.org/10.1007/s11244-009-9304-3

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