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One-pot synthesis of 1-acetylpyrene over supported phosphotungstic heteropoly acid catalysts

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Abstract

Phosphotungstic heteropoly acid (PW) supported on various oxides (SiO2, TiO2, K-10 montmorillonite and γ-Al2O3) were synthesized and used as catalysts for Friedel–Crafts acylation of pyrene with acetic anhydride to 1-acetylpyrene for the first time. The as-prepared catalysts were characterized by specific surface area measurement, X-ray diffraction, infrared spectroscopy, and temperature programmed desorption of ammonia. SiO2-supported phosphotungstic heteropoly acid (PW/SiO2, 40 wt%) was found to be the most active catalyst in the acylation giving 91.8 % yield and 100 % selectivity for 1-acetylpyrene at reaction temperature of 60 °C under ambient pressure. The effect of PW Loading, PW/SiO2 amount, molar ratio of reactants, reaction temperature and reaction time on the catalytic acylation reaction were studied in detail to optimize the process parameters. The reusability of the PW/SiO2 catalyst was appraised, and the possible pathway for the production of the Friedel–Crafts acylation of pyrene with acetic anhydride catalyzed by phosphotungstic heteropoly acid was also discussed briefly.

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References

  1. Metivier P (2001) Fine chemicals through heterogeneous catalysis, Wiley-VCH, Weinheim

  2. Répichet S, Roux CL, Roques N, Dubac J (2003) Tetrahedron Lett, 44: 2037

  3. Zamanifar E, Farzaneh F (2011) Reac Kinet Mech Cat 104:197

    Article  CAS  Google Scholar 

  4. Kim DJ, Kim JW, Choung SJ, Kang M (2008) J Ind Eng Chem 14:308

    Article  CAS  Google Scholar 

  5. Namuangruk S, Pantu P, Limtrakul J (2004) J Catal 225:523

    Article  CAS  Google Scholar 

  6. Kozhevnikov IV (2003) Appl Catal A 256:3

    Article  CAS  Google Scholar 

  7. Kozhevnikov IV (1998) Chem Rev 98:171

    Article  CAS  Google Scholar 

  8. Yang W, Billy J, Taarit YB, Vedrine JC, Essayem N (2002) Catal Today 73:153

    Article  CAS  Google Scholar 

  9. Kozhevnikov IV (2002) Catalysis by polyoxometalates. Wiley, Chichester

    Google Scholar 

  10. Kozhevnikov IV (1995) Catal Rev Sci Eng 37:311

    Article  CAS  Google Scholar 

  11. Kamiya Y, Okuhara T, Misono M, Miyaji A, Tsuji K, Nakajo T (2008) Catal Surv Asia 12:101

    Article  CAS  Google Scholar 

  12. Zhao XQ, Han YT, Sun XL, Wang YJ (2007) Chin J Catal 28:91

    Article  CAS  Google Scholar 

  13. Okuhara T, Mizuno N, Misono M (1996) Adv Catal 41:113

    Article  CAS  Google Scholar 

  14. Tagawa T, Amemiya J, Goto S (2004) Appl Catal A 257:19

    Article  CAS  Google Scholar 

  15. Kaur J, Griffin K, Harrison B, Kozhevnikov IV (2002) J Catal 208:448

    Article  CAS  Google Scholar 

  16. Firouzabadi H, Iranpoor N, Nowrouzi F (2004) Tetrahedron 60:10843

    Article  CAS  Google Scholar 

  17. Chen M, Li D, Luo Y, He MQ, Xie JM, Li HM, Yuan XH (2011) J Ind Eng Chem 17:14

    Article  CAS  Google Scholar 

  18. Chen M, Huang LJ, Luo Y, He MQ, Xie JM, Li HM, Yuan XH (2009) React Kinet Catal Lett 98:355

    Article  CAS  Google Scholar 

  19. Chen M, Wu YY, Luo Y, He MQ, Xie JM, Li HM, Yuan XH (2011) Reac Kinet Mech Cat 102:103

    Article  CAS  Google Scholar 

  20. Kanno M, Yasukawa T, Ninomiya W, Ooyachi K, Kamiya Y (2010) J Catal 273:1

    Article  CAS  Google Scholar 

  21. Sun P, Yu DH, Hu Y, Tang ZC, Xia JJ, Li H, Huang H (2001) Korean J Chem Eng 28:99

    Article  Google Scholar 

  22. Shen LQ, Feng YH, Yin HB, Wang AL, Yu LB, Jiang TS, Shen YT, Wu ZA (2011) J Ind Eng Chem 17:484

    Article  CAS  Google Scholar 

  23. Cardoso LAM, Alves W Jr, Gonzaga ARE, Aguiar LMG, Andrade HMC (2004) J Mol Catal A 209:189

    Article  CAS  Google Scholar 

  24. Pope MT (1983) Heteropoly and isopoly oxometalates. Springer-Verlag, Berlin

    Book  Google Scholar 

  25. Lu H, Yin H, Liu Y, Jiang T, Yu L (2008) Catal Commun 10:313

    Article  CAS  Google Scholar 

  26. Kirumakki SR, Shpeizer BG, Sagar GV, Chary KVR, Clearfield A (2006) J Catal 242:319

    Article  CAS  Google Scholar 

  27. Gaare K, Akporiaye D (1996) J Mol Catal A 109:177

    Article  CAS  Google Scholar 

  28. Dias JA, Osegovic JP, Drago RS (1999) J Catal 183:83

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported in part by the National Natural Science Foundation of China (No. 20207003).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang, 212013, Jiangsu, People’s Republic of China

    Min-Qiang He, Ai-Xia Pan, Ji-Min Xie, De-Li Jiang & Min Chen

  2. School of Material Science and Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang, 212013, Jiangsu, People’s Republic of China

    Xin-Hua Yuan

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  1. Min-Qiang He
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  2. Ai-Xia Pan
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  3. Ji-Min Xie
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  4. De-Li Jiang
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  6. Min Chen
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Correspondence to Min Chen.

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He, MQ., Pan, AX., Xie, JM. et al. One-pot synthesis of 1-acetylpyrene over supported phosphotungstic heteropoly acid catalysts. Reac Kinet Mech Cat 108, 531–544 (2013). https://doi.org/10.1007/s11144-012-0524-3

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