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Non-Metallic Ketone Compounds Catalyzed Selective Epoxidation of Styrene with Dry Air

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Abstract

Two non-metallic ketone catalysts resulted from fructose were first applied in the epoxidation of styrene with dry air to achieve considerably encouraging results, in which no any transition metal ion/oxide was involved. Ketone 1 was highly active, with the styrene conversion of 78.1 mol% and the epoxide selectivity of 92.0% at 363 K in 5 h. The poorer activity of ketone 2 was possibly associated with stronger steric hindrance of intermediate coordinative state. The occurrence of styrene epoxidation with dry air over the ketone could involve the coordination among solvent DMF, oxygen and ketone to form the peroxy ketone intermediate.

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References

  1. Xia QH, Ge HQ, Ye CP, Liu ZM, Su KX (2005) Chem Rev 105:1603

    Article  CAS  Google Scholar 

  2. Schcurig V, Betschinger F (1992) Chem Rev 92:873

    Article  Google Scholar 

  3. Punniyamurthy T, Velusamy S, Iqbal J (2005) Chem Rev 105:2329

    Article  CAS  Google Scholar 

  4. Katsuki T (1995) Coord Chem Rev 140:189

    Article  CAS  Google Scholar 

  5. Lu XH, Xia QH, Zhan HJ, Yuan HX, Ye CP, Su KX, Xu G (2006) J Mol Catal A Chem 250:62

    Article  CAS  Google Scholar 

  6. Shelnutt JA, Song XZ, Ma JG, Jia SL, Jentzen W, Medforth CJ (1997) Chem Soc Rev 27:31

    Article  Google Scholar 

  7. Porter MJ, Skidmore J (2000) Chem Commun 1215

  8. Mateos JL, Menchaca HJ (1964) J Org Chem 29:2026

    Article  CAS  Google Scholar 

  9. Lovas FJ, Suenram RD (1997) Chem Phys Lett 51:453

    Article  Google Scholar 

  10. Martinez RI, Huie RE, Herron JT (1997) Chem Phys Lett 51:457

    Article  Google Scholar 

  11. Suenram RD, Lovas RJ (1998) J Am Chem Soc 100:5117

    Article  Google Scholar 

  12. Murugavel R, Roesky HW (1997) Angew Chem Int Ed Engl 36:477

    Article  CAS  Google Scholar 

  13. Ellis PE, Lyons JE (1995) Coord Chem Rev 105:181

    Article  Google Scholar 

  14. Lyons JE, Ellis PE (1991) Catal Lett 8:45

    Article  CAS  Google Scholar 

  15. Punniyamurthy T, Reddy MM, Iqbal J (1996) Pure Appl Chem 68:619

    Article  CAS  Google Scholar 

  16. Puniyamurthy T, Kalra SJS, Iqbal J (1995) Terahedron Lett 36:8497

    Article  Google Scholar 

  17. Mukaiyama T, Yamada T (1995) Bull Chem Soc Jpn 68:17

    Article  CAS  Google Scholar 

  18. Birnbaum ER, Le Lacheur RM, Horton AC, Tumas W (1999) J Mol Catal A Chem 24:13911

    Google Scholar 

  19. Wang ZX, Tu Y, Frohn M, Zhang JR, Shi Y (1997) J Am Chem Soc 119:11224

    Article  CAS  Google Scholar 

  20. Frohn M, Wang ZX, Shi Y (1998) J Org Chem 63:6425

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledge the funding supports provided by National Natural Science Foundation of China (No. 20673035), by the 2007 excellent mid-youth innovative project of Hubei Provincial Education Department of China (No. T200701), by the project-sponsored by SRF for ROCS, SEM of China (No. [2007]24), by the key project of Hubei Provincial Science & Technology Department of China (2008CDA030), and by MOE Key Laboratory of Hubei University, China (No. 2006-KL-001).

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Authors and Affiliations

  1. Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules & School of Chemistry and Chemical Engineering, Hubei University, 430062, Wuhan, China

    X.-H. Lu, G. Xu, Z.-R. Tang, Q.-H. Xia, Q. Zhang & T. Pang

  2. Jingchu University of Technology, 448000, Jingmen, China

    H.-J. Zhan

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  1. X.-H. Lu
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  2. G. Xu
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  3. Z.-R. Tang
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  4. Q.-H. Xia
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  5. H.-J. Zhan
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  6. Q. Zhang
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  7. T. Pang
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Correspondence to Q.-H. Xia.

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Lu, XH., Xu, G., Tang, ZR. et al. Non-Metallic Ketone Compounds Catalyzed Selective Epoxidation of Styrene with Dry Air. Catal Lett 132, 487–491 (2009). https://doi.org/10.1007/s10562-009-0117-6

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  • DOI: https://doi.org/10.1007/s10562-009-0117-6

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