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).
Similar content being viewed by others
References
Schofield K (1980) Aromatic nitration. Cambridge University Press, Cambridge
Olah GA, Malhotra R, Narang SC (1989) Nitration: methods and mechanisms. VCH, New York
Coombes RG, Golding JG, Hadjigeorgiou P (1979) J Chem Soc Perkin Trans 2:1451
Clark JH (2002) Acc Chem Res 35:791
Clark JH (ed) (1994) Catalysis of organic reactions using supported inorganic reagents. VCH, New York
Delaude L, Laszlo P, Smith K (1993) Acc Chem Res 26:607
Smith K (1992) In: Yoshida Z, Ohshiro Y (eds) New aspects of organic synthesis II. Kadonsha, Tokyo; VCH, Weinheim, p 43
Butters M (1992) In: Smith K (ed) Solid supports and catalysts in organic synthesis. Ellis Horwood, Chichester, p 130
Smith K (1991) In: Scaros MG, Prunier ML (eds) Catalysis of organic reactions. Marcel Dekker, New York, p 91
Smith K, El-Hiti GA (2004) Curr Org Synth 1:253
Smith K, El-Hiti GA (2006) Curr Org Chem 10:1603
Smith K, Roberts SD, El-Hiti GA (2003) Org Biomol Chem 1:1552
Smith K, El-Hiti GA, Jayne AJ, Butters M (2003) Org Biomol Chem 1:1560
Smith K, El-Hiti GA, Jayne AJ, Butters M (2003) Org Biomol Chem 1:2321
Smith K, Ewart GM, El-Hiti GA, Randles KR (2004) Org Biomol Chem 2:3150
Smith K, El-Hiti GA, Hammond MEW, Bahzad D, Li Z, Siquet C (2000) J Chem Soc Perkin Trans 1:2745
Smith K, Butters M, Paget WE, Goubet D, Fromentin E, Nay B (1999) Green Chem 1:83
Smith K, Musson A, DeBoos GA (1998) J Org Chem 63:8448
Smith K, Gibbins T, Millar RW, Claridge RP (2000) J Chem Soc Perkin Trans 1:2753
Smith K, Almeer S, Black SJ (2000) Chem Commun 1571
Smith K, Almeer S, Peters C (2001)Chem Commun 2748
Smith K, Almeer S, Black SJ, Peters C (2002) J Mater Chem 12:3285
Rodrigues JAR, de Oliveira Filho AP, Moran PJS, Custódio R (1999) Tetrahedron 55:6733
Yin W-P, Shi M (2005) Tetrahedron 61:10861
Gigante B, Prazeres AO, Marcelo-Curto MJ, Cornélis A, Laszlo P (1995) J Org Chem 60:3445
Milczak T, Jacniacki J, Zawadzki J, Malesa M, Skupiński W (2001) Synth Commun 31:173
Heravi MM, Benmorad T, Bakhtiari K, Bamoharram FF, Oskooie HH (2007) J Mol Catal A Chem 264:318
Mallick S, Parida KM (2007) Catal Commun 8:1487
Parida KM, Rath D (2006) J Mol Catal A Chem 258:381
Riego JM, Sedin Z, Zaldlvar J-M, Marzianot NC, Tortato C (1996) Tetrahedron Lett 37:513
Zolfigol MA, Ghaemi E, Madrakian E (2001) Molecules 6:614
Sunajadevi KR, Sugunan S (2005) Catal Commun 6:611
Sunajadevi KR, Sugunan S (2006) Mater Lett 60:3813
Khder AS, Ahmed AI (2009) Appl Catal A 354:153
Dagade SP, Kadam VS, Dongare MK (2002) Catal Commun 3:67
Esakkidurai T, Pitchumani K (2002) J Mol Catal A Chem 185:305
Taylor R (1990) Electrophilic aromatic substitution. Wiley, Chichester, p 263
Vione D, Belmondo S, Carnino L (2004) Environ Chem Lett 2:135
Acknowledgments
We thank Cardiff University and the Saudi Government for financial support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
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
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11244-009-9304-3