One-Pot Synthesis of 1-Benzoylpyrene over Heteropoly Acid Catalysts

Abstract:

A novel one-pot catalytic synthesis of 1-benzoylpyrene through acylation of pyrene with benzoyl chloride catalyzed by various Keggin type heteropoly acids (salts) was investigated. Pure 1-benzoylpyrene was obtained and the structure of 1-benzoylpyrene was identified by GC/MS, FT-IR and 1H NMR spectra. H3PW12O40 (PW) was found to be the most active catalyst in the acylation. The yield and the selectivity of 1-benzoylpyrene were up to 97.6 % and 100 %, respectively. The effects of experimental parameters on the catalytic acylation reaction and the recycling performance of PW catalyst were studied. PW catalyst shows well catalytic activity after running for 5 times. The facile product separation and the recycling performance of PW catalyst is expected to contribute to the development of clean and environmentally friendly strategy for the synthesis of 1-benzoylpyrene.

• Periodical: Advanced Materials Research (Volumes 560-561)
• Pages: 294-299
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.560-561.294
• Online since: August 2012
• Authors: Xiao Qing Lu, Min Xing, Ai Xia Pan, Yin Yin Wu, Ji Min Xie, Min Chen
• Keywords: 1-Benzoylpyrene, Catalysis, Friedel-Crafts Acylation, Heteropoly Acids, Pyrene

References

[1] Olah, G.A., Friedel–Crafts and Related Reactions, Wiley–Interscience: New York, (1973).

[2] Clark, J.H., Rhodes, C.N., Clean Synthesis Using Porous Inorganic Solid Catalysts, Acc. Chem. Res., 35 (2002) 791.

[3] Sárkány, A., Acetylene hydrogenation on SiO2 supported gold nanoparticles, React. Kinet. Catal. Lett., 96 (2009) 43−54.

DOI: 10.1007/s11144-009-5438-3

[4] Okuhara, T., Mizuno, N., Misono, M., Catalytic Chemistry of Heteropoly Compounds, Advances in Catalysis, 41 (1996) 113−225.

DOI: 10.1016/s0360-0564(08)60041-3

[5] Yadav, J.S., Subba, Reddy, B.V., Sreedhar, R., Shreenivas, Rao, R., Nagaiah, K., Silver Phosphotungstate: A Novel and Recyclable Heteropoly Acid for Friedländer Quinoline Synthesis, Synthesis, 14 (2004) 2381−2385.

DOI: 10.1055/s-2004-831185

[6] Tagawa, T., Amemiya, J., Goto, S., Chlorine-free Friedel–Crafts acylation of benzene with benzoic anhydride on insoluble heteropoly acid catalyst, Appl. Catal. A: Gen., 257 (2004) 19-23.

DOI: 10.1016/s0926-860x(03)00638-0

[7] Kaur, J., Griffin, K., Harrison, B., Kozhevnikov, I.V., Friedel–Crafts Acylation Catalysed by Heteropoly Acids, J. Catal., 208 (2002) 448–455.

DOI: 10.1006/jcat.2002.3592

[8] Firouzabadi, H., Iranpoor, N., Nowrouzi, F., Aluminum dodecatungstophosphate (AlPW12O40) as a non-hygroscopic Lewis acid catalyst for the efficient Friedel–Crafts acylation of aromatic compounds under solvent-less conditions, Tetrahedron, 60 (2004).

DOI: 10.1016/j.tet.2004.09.049

[9] Chen, M., Huang, L.J., Luo, Y., He, M. Q, Xie, J.M., Yuan, X.H., Preparation of 3, 6-dibenzoylacenapthene in the presence of Lewis acidic ionic liquids, React Kinet Catal Lett, 98 (2009) 355−363.

DOI: 10.1007/s11144-009-0088-z

[10] Gaare, K., Akporiaye, D., Modified zeolites as catalysts in the Friedel-Crafts acylation, J. Mol. Catal. A, 109 (1996) 177–187.

DOI: 10.1016/1381-1169(96)00023-4

[11] Neves, I., Jayat F., Magnoux, P., Pérot, G., Ribeiro, F.R., Gubelmann, M., Guisnet, M., Acylation of phenol with acetic acid over a HZSM5 zeolite, reaction scheme, J. Mol. Catal., 93 (1994)169–179.

DOI: 10.1016/0304-5102(94)00107-3

[12] Rafiee, E., Paknezhad, F., Shahebrahimi, S., Joshaghani, M., Eavani, S., Rashidzadeh, S., Acid catalysis of different supported heteropoly acids for a one-pot synthesis of β-acetamido ketones, J. Mol. Catal. A, 282 (2008) 92–98.

DOI: 10.1016/j.molcata.2007.11.021