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Oxidation of Thymol and Carvacrol to Thymoquinone with KHSO5 Catalyzed by Iron Phthalocyanine Tetrasulfonate in a Methanol–Water Mixture

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Abstract

The oxidation of thymol and carvacrol to thymoquinone with potassium peroxymonosulfate (KHSO5) catalyzed by iron phthalocyanine tetrasulfonate (FePcTS) in a methanol (4.0 mL)–water (0.5 mL) mixture has been carried out. In a typical reaction, the amounts of the substrate, oxidant, and catalyst were 0.300, 0.600, and 1 × 10−3 millimoles, respectively. Ninety-nine percent conversions of thymol in 1 h and of carvacrol in 30 min were achieved at ambient temperature. The major product of both oxidation reactions was thymoquinone (2-isopropyl-5-methylbenzoquinone, TQ) and the reactions also yielded polymeric products poly(2-isopropyl-5-methyl-1,4-phenylene oxide) and poly(5-isopropyl-2-methyl-1,3-phenylene oxide). These polymers are novel and not reported before. When H2O2 or ButOOH was used as the oxidant, the yield of TQ was <1 %.

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References

  1. Cavailero JAS, Nascimento GMS, Neves MGPMS, Silvestre AJD, Vicente MGH (1996) Tetrahedron Lett 37:1893

    Article  Google Scholar 

  2. Silvestre AJD, Cavailero JAS, Silva AMS., Delmond B, Filliatre C (1996) Heterocycl Commun 2:371

    Article  CAS  Google Scholar 

  3. Silvestre AJD, Cavailero JAS, Silva AMS, Delmond B, Filliatre C (1997) J Chem Res., Synop. 228

  4. Dictionary of organic compounds, vol. 4, 6th edn (1996). Chapman & Hall, London

  5. Worthen DR, Ghosheh OA, Crooks PA (1998) Anticancer Res 18:1527

    CAS  Google Scholar 

  6. Daba MH, Abdelrahman MS (1998) Toxicol Lett 95:23

    Article  CAS  Google Scholar 

  7. Houghton PJ, Zarka R, Delasheras B, Hoult JRS (1995) Planta Med 61:33

    Article  CAS  Google Scholar 

  8. Ghosheh OA, Houdi AA, Crooks PA (1999) J Pharm Biomed Anal 19:757

    Article  CAS  Google Scholar 

  9. Nergiz C, Otles S (1993) Food Chem 48:259

    Article  CAS  Google Scholar 

  10. The Merck index of chemicals and drugs, Merck & CO, Rahway, p 1046

  11. Martins RRL, Neves MGPMS, Silvestre AJD, Silva AMS, Cavaleiro JAS, (1999) J Mol Catal A Chem 137:41

    Article  CAS  Google Scholar 

  12. Milos M (2001) Appl Catal A Gen 216:157

    Article  CAS  Google Scholar 

  13. Ay B, Yildiz E, Jones S, Zubieta J (2012) Inorg Chim Acta 387:15

    Article  CAS  Google Scholar 

  14. Skrobot FC, Valente AA, Neves G, Rosa I, Rocha J, Cavaleiro JAS (2003) J Mol Catal A Chem 201:211

    Article  CAS  Google Scholar 

  15. Santos ICMS, Simões MMQ, Pereira MMMS, Martins RRL, Neves MGPMS, Cavaleiro JAS, Cavaleiro AMV (2003) J Mol Catal A Chem 195:253

    Article  CAS  Google Scholar 

  16. Uliana MP, Vieria YW, Donatoni MC, Corrêa AG, Brocksom U, Brocksom TJ (2008) J Braz Chem Soc 19:1484

    Article  CAS  Google Scholar 

  17. Sorokin AB, Kudrik EV (2011) Catal Today 159:37

    Article  CAS  Google Scholar 

  18. Calvete MJF, Silva M, Pereira MM, Burrows HD (2013) RSC Adv 3:22774

    Article  CAS  Google Scholar 

  19. Zagal JH, Griveau S, Francisco Silva J, Nyokong T, Bedioui F (2010) Coord Chem Rev 254:2755

    Article  CAS  Google Scholar 

  20. Huang Z, Yao Y, Lu J, Chen C, Lu W, Huang S, Chen W (2016) J Hazard Mater 301:214

    Article  CAS  Google Scholar 

  21. Saka EC, Çelik G, Sarkı G, Kantekin H (2016) J Incl Phenom Macrocycl Chem 85:161

    Article  CAS  Google Scholar 

  22. Zalomaeva OV, Ivanchikova ID, Kholdeeva OA, Sorokin AB (2009) New J Chem 33:1031

    Article  CAS  Google Scholar 

  23. Maeno S, Mizutani Y, Zhu Q, Miyamoto T, Fukushima M, Kuramitz H (2014) J Environ Sci Health A 49:981

    Article  CAS  Google Scholar 

  24. Weber JH, Busch DH (1965) Inorg Chem 4:469

    Article  CAS  Google Scholar 

  25. Kolesnik IG, Zhizhina EG, Matveev KI (2000) J Mol Catal A Chem 153:147

    Article  CAS  Google Scholar 

  26. Trukhan NN, Romannikov VN, Paukshtis EA, Shmakov AN, Kholdeeva OA (2001) J Catal 202:110

    Article  CAS  Google Scholar 

  27. Palacio M, Villabrille PI, Romanelli GP, Vázquez PG, Cáceres CV (2012) Appl Catal A Gen 417–418:273

    Article  Google Scholar 

  28. Sorokin A, Meunier B (1996) Chem Eur J 2:1308

    Article  CAS  Google Scholar 

  29. Hemmert C, Renz M, Meunier B (1999) J Mol Catal A Chem 137:205

    Article  CAS  Google Scholar 

  30. Sanchez M, Chap N, Cazaux JB, Meunier B (2001) Eur J Inorg Chem 2001:1775

    Article  Google Scholar 

  31. Çimen Y, Türk H, (2008) Appl Catal A Gen 340:52

    Article  Google Scholar 

  32. Afanasiev P, Kudrik EV, Albrieux F, Briois V, Koifman OI, Sorokin AB (2012) Chem Commun 48:6088

    Article  CAS  Google Scholar 

  33. Neu HM, Zhdankin VV, Nemykin VN (2010) Tetrahedron Lett 51:6545

    Article  CAS  Google Scholar 

  34. Sorokin AB (2013) Chem Rev 113:8152

    Article  CAS  Google Scholar 

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Acknowledgments

This research was supported by Anadolu University Scientific Research Commission, Turkey (Grant No. 1505F313). The authors would like to thank Dr. İlhami Çelik for taking the 1H NMR and gHSQCAD NMR spectra.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Anadolu University, 26470, Eskişehir, Turkey

    Tuğçe Günay, Yasemin Çimen, R. Bengü Karabacak & Hayrettin Türk

Authors
  1. Tuğçe Günay
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  2. Yasemin Çimen
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  3. R. Bengü Karabacak
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  4. Hayrettin Türk
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Corresponding author

Correspondence to Yasemin Çimen.

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Günay, T., Çimen, Y., Karabacak, R.B. et al. Oxidation of Thymol and Carvacrol to Thymoquinone with KHSO5 Catalyzed by Iron Phthalocyanine Tetrasulfonate in a Methanol–Water Mixture. Catal Lett 146, 2306–2312 (2016). https://doi.org/10.1007/s10562-016-1850-2

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  • DOI: https://doi.org/10.1007/s10562-016-1850-2

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