Synthesis of 1-benzoylpyrene using silica-supported phosphotungstic heteropoly acid as an efficient and reusable catalyst

Minqiang He; Aixia Pan; Jimin Xie; Huamin Li; Xinhua Yuan; Xiaonong Cheng; Min Chen

Korean Journal of Chemical Engineering, Vol.29, No.10, 1388-1392, October, 2012

DOI10.1007/s11814-012-0039-7 Export Citation

Synthesis of 1-benzoylpyrene using silica-supported phosphotungstic heteropoly acid as an efficient and reusable catalyst

Minqiang He, Aixia Pan, Jimin Xie, Huamin Li, Xinhua Yuan¹, Xiaonong Cheng¹, and Min Chen^†

School of Chemistry and Chemical Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang, Jiangsu 212013, P. R. China
¹School of Material Science and Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang, Jiangsu 212013, P. R. China

E-mail:

A novel one-pot catalytic synthesis of 1-benzoylpyrene through acylation of pyrene with benzoic anhydride catalyzed by several heteropoly acids (HPAs) was investigated. Pure 1-benzoylpyrene was obtained and its structure was identified by GC/MS, FT-IR and 1H NMR spectra. Silica-supported phosphotungstic heteropoly acid (PW/SiO2) was found to be the most active catalyst in the acylation. The yield and the selectivity of 1-benzoylpyrene were up to 62.5% and 100%, respectively. The effects of experimental parameters on the catalytic acylation reaction, and the possibility of reusability of PW/SiO2 catalyst were studied. PW/SiO2 catalyst is easily separable from the reaction mixture and reusable without loss of its activity.

Keywords:1-Benzoylpyrene;Friedel-Crafts Acylation;Pyrene;Heteropoly Acids;Catalysis

[References]

Olah GA, Friedel-crafts and related reactions, Wiley-Interscience, New York (1973)
Metivier P, Fine chemicals through heterogeneous catalysis, Wiley-VCH, Weinheim (2001)
Sarkany A, React. Kinet. Catal. Lett., 43, 96 (2009)
Yang L, Joo JB, Kim ND, Jung KS, Yi J, Korean J. Chem. Eng., 27(6), 1695 (2010)
Park DR, Hong UG, Song SH, Seo JG, Baeck SH, Chung JS, Song IK, Korean J. Chem. Eng., 27(2), 465 (2010)
Kozhevnikov IV, Kloetstra KR, Sinnema A, Zandbergen HW, Bekkum H, J. Mol. Catal. A., 114, 287 (1996)
Moffat JB, Metal-oxygen cluster-the surface and catalytic properties of heteropoly oxometalates, Kluwer, New York (2001)
Dias JA, Caliman E, Dias SCL, Paulo M, Souza ATCP, Catal. Today., 39, 85 (2003)
Tagawa T, Amemiya J, Goto S, Appl. Catal. A., 19, 257 (2004)
Kaur J, Griffin K, Harrison B, Kozhevnikov IV, J. Catal., 208(2), 448 (2002)
Cardoso LAM, Gonzaga ARE, Aguiar LMG, Andrade HMC, J. Mol. Catal. A., 189, 209 (2004)
Firouzabadi H, Iranpoor N, Nowrouzi F, Tetrahedron., 60, 10843 (2004)
Repichet S, Le Roux C, Roques N, Dubac J, Tetrahedron Lett., 44, 2037 (2003)
Chen M, Huang LJ, Luo Y, He MQ, Xie JM, Yuan XH, React. Kinet. Catal. Lett., 98(2), 355 (2009)
Blasco T, Corma A, Martinez A, Martinez-Escolano P, J. Catal., 177(2), 306 (1998)
Kozhevnikov IV, Chem. Rev., 98(1), 171 (1998)
Dias JA, Osegovic JP, Drago RS, J. Catal., 83, 183 (1999)
Rafiee E, Paknezhad F, Shahebrahimi S, Joshaghani M, Eavani S, Rashidzadeh S, J. Mol. Catal. A., 92, 282 (2008)

[1] Olah GA, Friedel-crafts and related reactions, Wiley-Interscience, New York (1973)

[2] Metivier P, Fine chemicals through heterogeneous catalysis, Wiley-VCH, Weinheim (2001)

[3] Sarkany A, React. Kinet. Catal. Lett., 43, 96 (2009)

[4] Yang L, Joo JB, Kim ND, Jung KS, Yi J, Korean J. Chem. Eng., 27(6), 1695 (2010)

[5] Park DR, Hong UG, Song SH, Seo JG, Baeck SH, Chung JS, Song IK, Korean J. Chem. Eng., 27(2), 465 (2010)

[6] Kozhevnikov IV, Kloetstra KR, Sinnema A, Zandbergen HW, Bekkum H, J. Mol. Catal. A., 114, 287 (1996)

[7] Moffat JB, Metal-oxygen cluster-the surface and catalytic properties of heteropoly oxometalates, Kluwer, New York (2001)

[8] Dias JA, Caliman E, Dias SCL, Paulo M, Souza ATCP, Catal. Today., 39, 85 (2003)

[9] Tagawa T, Amemiya J, Goto S, Appl. Catal. A., 19, 257 (2004)

[10] Kaur J, Griffin K, Harrison B, Kozhevnikov IV, J. Catal., 208(2), 448 (2002)

[11] Cardoso LAM, Gonzaga ARE, Aguiar LMG, Andrade HMC, J. Mol. Catal. A., 189, 209 (2004)

[12] Firouzabadi H, Iranpoor N, Nowrouzi F, Tetrahedron., 60, 10843 (2004)

[13] Repichet S, Le Roux C, Roques N, Dubac J, Tetrahedron Lett., 44, 2037 (2003)

[14] Chen M, Huang LJ, Luo Y, He MQ, Xie JM, Yuan XH, React. Kinet. Catal. Lett., 98(2), 355 (2009)

[15] Blasco T, Corma A, Martinez A, Martinez-Escolano P, J. Catal., 177(2), 306 (1998)

[16] Kozhevnikov IV, Chem. Rev., 98(1), 171 (1998)

[17] Dias JA, Osegovic JP, Drago RS, J. Catal., 83, 183 (1999)

[18] Rafiee E, Paknezhad F, Shahebrahimi S, Joshaghani M, Eavani S, Rashidzadeh S, J. Mol. Catal. A., 92, 282 (2008)