Acylation of aromatic compounds by acid anhydrides using Preyssler's anion [NaP5W30O110]14- and heteropolyacids as green catalysts

• Authors: Ali Gharib , Manouchehr Jahangir , J. Scheeren
• Languages of publication: EN

Abstracts

EN

The Preyssler, Wells-Dowson and Keggin heteropolyacids are efficient and eco-friendly solid acid catalysts for the acylation of electron-rich aromatic compounds with acid anhydrides. The performance of different forms of heteropolyacids was compared. In all the cases, the best results were obtained using the Preyssler heteropolyacid as the catalyst. In the presence of 25 mol% (with respect to H+ equivalency) Preyssler catalyst, highly para-selective acetylation of anisole occurs using two equivalents of acetic anhydride, in 15 min at room temperature. The isolated yield of the p-methoxyacetophenone product is 98%.

Keywords

EN

Acylation; Preyssler; Anhydride; Heteropolyacids; Catalyst; Aromatic compounds

• Publisher: De Gruyter Open
• Journal: Polish Journal of Chemical Technology
• Year: 2011
• Volume: 13
• Issue: 2
• Pages: 11-17

Dates

published

1 - 1 - 2011

online

16 - 6 - 2011

Contributors

author

Ali Gharib

author

Manouchehr Jahangir

• Department of Chemistry, Islamic Azad University, Mashhad, IRAN

author

J. Scheeren

• Cluster for Molecular Chemistry, Department of Organic Chemistry, Radboud University Nijmegen, The Netherlands

References

• Olah, G.A. (1964). Friedel-Crafts and Related reactions, Wiley-Interscience, New York, vol. I&IV, 1963-1964.
• Metivier, P. & Sheldon, R. A. (2001). in Fine Chemicals through Heterogeneous Catalysis, Wiley-VCH, Weinheim, p. 161.
• Olah, G.A. (1964). Friedel-Crafts and Related Reactions. vols. II, and III, Wiley, New York.
• Kozhevnikov, I.V. (2003). Friedel-Crafts acylation and related reactions catalysed by heteropoly acids. Applied Catalysis A: General. 256, 3-18. DOI: 10.1016/S0926-860X(03)00406-X.[Crossref]
• Okuhara, T., Mizuno., N. & Misono, M. (1996). Catalytic Chemistry of Heteropoly compounds, Advances in Catalysis. 41, 113-252.
• Gaare, K. & Akporiaye, D. (1996). Modified zeolites as catalysts in the Friedel-Crafts acylation. J. Mol. Catal A. 109, 177-187. DOI: 10.1016/1381-1169(96)00023-4.[Crossref]
• Neves, I., Jayat, F., Magnoux, P., Pérot, G., Ribeiro, F.R., Gubelmann, M. & Guisnet, M. (1994). Acylation of phenol with acetic acid over a HZSM5 zeolite, reaction scheme. J. Mol. Catal. 93, 169-179. DOI: 10.1016/0304-5102(94)00107-3.[Crossref]
• Gharib, A., Scheeren, J. (Hans) W., Bamoharram, F.F., Roshani, M. & Jahangir. M. (2009). Acetylation of p-Aminophenol by Preyssler's anion [NaP5W30O110]14-, [NaP5W29MoO110]14- with green condition at room temperature. Pol. J. Chem.l Technol. 11 (2), 31-35. DOI: 10.2478/v10026-009-0020-3.[WoS][Crossref]
• Bamoharram, F.F., Heravi, M.M., Roshani, M., Gharib, A. & Jahangir, M. (2007). Catalytic Method for Synthesis of Aspirin by a Green, Efficient and Recyclable Solid Acid Catalyst (Preyssler's Anion) at Room Temperature. J. Chinese Chem. Soc. 54, 1017-1020.
• Gharib, A., Jahangir, M. & Roshani, M. (2009). Novel synthesis using heteropolyacid catalysts. Magazine of the Royal Australian Chemical Institute Inc. 76, 2, 12-15.
• Hekmatshoar, R., Sajadi, S., Heravi, M.M. & Bamoharram, F.F. (2007). H14[NaP5W30O110] as a Heterogeneous Recyclable Catalyst for the Air Oxidation of Thiols Under Solvent Free Conditions. Molecules. 12, 2223-2228. DOI: 10.3390/12092223.[Crossref][WoS]
• Alizadeh, M.H., Harmalker, S.P., Jeannin, Y., Martin-Frere, J. & Pope, M.T. (1985). A Heteropolyanion with Five-fold Molecular Symmetry That Contains a Nonlabile Encapsulated Sodium Ion. The Structure and Chemistry of [NaP5W30O110]14-. J. Am. Chem. Soc. 107, 2662-2669. DOI: 10.1021/ja00295a019.[Crossref]
• Shanshan, Wu., Weihong, Zhang., Jum, Wang. & Xiaoqian, Ren. (2008). Preyssler-Structured Tungsto-phosphoric Acid Catalyst on Functionalized Silica for Esterification of n-Butanol with Acetic Acid. Catal. Lett. 123, 276-281. DOI: 10.1007/s10562-008-9419-3.[Crossref][WoS]
• Ma, Y., Wang, Q.L., Jian, W. & Zuo, B. (1997). Friedal - Crafts acylation of anisole over zeolite catalysts. Appl. Catal. A. 165, 199-206. DOI: 10.1016/S0926-860X(97)00201-9.[Crossref]

Identifiers

DOI

10.2478/v10026-011-0017-6