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2011 | 13 | 2 | 11-17
Tytuł artykułu

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

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
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%.
Wydawca

Rocznik
Tom
13
Numer
2
Strony
11-17
Opis fizyczny
Daty
wydano
2011-01-01
online
2011-06-16
Twórcy
autor
  • Department of Chemistry, Islamic Azad University, Mashhad, IRAN
autor
  • Cluster for Molecular Chemistry, Department of Organic Chemistry, Radboud University Nijmegen, The Netherlands
Bibliografia
  • 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]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_v10026-011-0017-6
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