Skip to main content
SpringerLink
Log in

Clean and Selective Oxidation of Alcohols with Oxone and Phase-Transfer Catalysts in Water

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A new, simple, metal-free, and eco-friendly procedure has been proposed for the oxidation of alcohols with Oxone (potassium peroxymonosulfate) in water in the presence of six phase-transfer catalysts (PTC). Phase-transfer catalysts were found to display high catalytic activity in water solution. Furthermore, the oxidation of alcohols was also carried out with relatively good conversion and selectivity in water without any catalyst.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme

Similar content being viewed by others

REFERENCES

  1. Brink, G.T., Arends, I.W.C.E., and Sheldon, R.A., Science, 2000, vol. 287, p. 1636. https://doi.org/10.1126/science.287.5458.1636

    Article  PubMed  Google Scholar 

  2. Tojo, G. and Fernandez, M., Oxidation of Alcohols to Aldehydes and Ketones, Boston: Springer, 2006. https://doi.org/10.1007/b135954

  3. Mohammadi, M., Rezaei, A., Khazaei, A., Shu, X.W., and Zheng, H.J.,ACS Appl. Mater. Interfaces, 2019, vol. 11, p. 33194. https://doi.org/10.1021/acsami.9b07961

    Article  CAS  PubMed  Google Scholar 

  4. Cainelli, G. and Cardillo, G., Chromium Oxidations in Organic Chemistry, Berlin: Springer, 1984. https://doi.org/10.1007/978-3-642-69362-5

  5. Mijs, W.J. and de Jonge, C.R.H., Organic Synthesis by Oxidation with Metal Compounds, New York: Plenum, 1986. https://doi.org/10.1007/978-1-4613-2109-5

  6. Zhan, B.Z., White, M.A., Sham, T.K., Pincock, J.A., Doucet, R.J., Rao, K.V.R., Robertson, K.N., and Cameron, T.S., J. Am. Chem. Soc., 2003, vol. 125, p. 2195. https://doi.org/10.1021/ja0282691

    Article  CAS  PubMed  Google Scholar 

  7. Guan, B.T., Xing, D., Cai, G.X., Wan, X.B., Yu, N., Fang, Z., and Shi, Z.J., J. Am. Chem. Soc., 2005, vol. 127, p. 18004. https://doi.org/10.1021/ja055398j

    Article  CAS  PubMed  Google Scholar 

  8. Enache, D.I., Edwards, J.K., Landon, P., SolsonaEspriu, B., Carley, A.F., Herzing, A.A., Watanabe, M., and Kiely, C.J., Science, 2006, vol. 311, p. 362. https://doi.org/10.1126/science.1120560

    Article  CAS  PubMed  Google Scholar 

  9. Zeng, X.M., Chen, J.M., Middleton, K., and Zhdankin, V.V.,Tetrahedron Lett., 2011, vol. 52, p. 5652. https://doi.org/10.1016/j.tetlet.2011.08.097

    Article  CAS  Google Scholar 

  10. Liu, G., Liu, J.H., Li, W.X., Liu, C., Wang, F., He, J.K., Guild, C., Jin, J., Kriz, D., Miao, R., and Suib, S.L., Appl. Catal. A: Gen., 2017, vol. 535, p. 77. https://doi.org/10.1016/j.apcata.2017.02.006

    Article  CAS  Google Scholar 

  11. Uozumi, Y. and Nakao, R., Angew. Chem., Int. Ed., 2003, vol. 42, p. 194. https://doi.org/10.1002/anie.200390076

    Article  CAS  Google Scholar 

  12. Sloboda-Rozner, D., Alsters, P.L., and Neumann, R., J. Am. Chem. Soc., 2003, vol. 125, p. 5280. https://doi.org/10.1021/ja0344821

    Article  PubMed  Google Scholar 

  13. Buffin, B.P., Clarkson, J.P., Belitz, N.L., and Kundu, A.,J. Mol. Catal. A: Chem., 2005, vol. 225, p. 111. https://doi.org/10.1016/j.molcata.2004.08.035

    Article  CAS  Google Scholar 

  14. Lei, Z.Q., Yang, Y.X., and Bai, X.Z., Adv. Synth. Catal., 2006, vol. 348, p. 877. https://doi.org/10.1002/adsc.200505356

    Article  CAS  Google Scholar 

  15. Sangtrirutnugul, P., Chaiprasert, T., Hunsiri, W., Jitjaroendee, T., Songkhum, P., Laohhasurayotin, K., Osotchan, T., and Ervithayasuporn, V.,ACS Appl. Mater. Interfaces, 2017, vol. 7, p. 12812. https://doi.org/10.1021/acsami.7b03910

    Article  CAS  Google Scholar 

  16. Bolm, C., Magnus, A.S., and Hildebrand, J.P., Org. Lett., 2000, vol. 2, p. 1173. https://doi.org/10.1021/ol005792g

    Article  CAS  PubMed  Google Scholar 

  17. Surendra, K., Krishnaveni, N.S., Reddy, M.A., Nageswar, Y.V.D., and Rao, K.R., J. Org. Chem., 2003, vol. 68, p. 2058. https://doi.org/10.1021/jo026751w

    Article  CAS  PubMed  Google Scholar 

  18. Krishnaveni, N.S., Surendra, K., and Rao, K.R., Adv. Synth. Catal., 2004, vol. 346, p. 346. https://doi.org/10.1002/adsc.200303164

    Article  CAS  Google Scholar 

  19. Thottumkara, A.P., Bowsher, M.S., and Viond, T.K., Org. Lett., 2005, vol. 7, p. 2933. https://doi.org/10.1021/ol050875o

    Article  CAS  PubMed  Google Scholar 

  20. Wu, S., Ma, H.C., and Lei, Z.Q., Tetrahedron, 2010, vol. 66, p. 8641. https://doi.org/10.1016/j.tet.2010.09.035

    Article  CAS  Google Scholar 

  21. Moriyama, K., Takemura, M., and Togo, H., J. Org. Chem., 2014, vol. 79, p. 6094. https://doi.org/10.1021/jo5008064

    Article  CAS  PubMed  Google Scholar 

  22. Uyanik, M., Akakura, M., and Ishihara, K., J. Am. Chem. Soc., 2009, vol. 131, p. 251. https://doi.org/10.1021/ja807110n

    Article  CAS  PubMed  Google Scholar 

  23. Parida, K.N., Jhulki, S., Mandal, S., and Moorthy, J.N., Tetrahedron, 2012, vol. 68, p. 9763. https://doi.org/10.1016/j.tet.2012.09.028

    Article  CAS  Google Scholar 

  24. Hussain, H., Green, I.R., and Ahmed, I., Chem. Rev., 2013, vol. 113, p. 3329. https://doi.org/10.1021/cr3004373

    Article  CAS  PubMed  Google Scholar 

  25. Do, J.S. and Chou, T.C., Ind. Eng. Chem. Res., 1990, vol. 29, p. 1095. https://doi.org/10.1021/ie00103a002

    Article  CAS  Google Scholar 

  26. Selvaraj, V., Abimannan, P., and Rajendran, V., Ultrason. Sonochem., 2014, vol. 21, p. 1805. https://doi.org/10.1016/j.ultsonch.2014.04.010

    Article  CAS  PubMed  Google Scholar 

Download references

Funding

This work was supported by the Nature Science Foundation of China (grant nos. 21563026, 21764012), by the Science and Technology Program of Gansu Province (no. 19JR2RA020), and by the Scientific Research Ability Promotion Program of Young Teachers of Northwest Normal University (no. NWNU-LKQN-18-18).

Author information

Authors and Affiliations

  1. Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, Northwest Normal University, 730070, Lanzhou, Gansu, China

    Y. X. Yang, M. Kang, X. Q. An, W. Zeng, Z. W. Yang & H. C. Ma

  2. Key Laboratory of Eco-environmental Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, 730070, Lanzhou, Gansu, China

    Y. X. Yang, M. Kang, X. Q. An, W. Zeng, Z. W. Yang & H. C. Ma

Authors
  1. Y. X. Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Kang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. X. Q. An
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. W. Zeng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Z. W. Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. H. C. Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Y. X. Yang.

Ethics declarations

The authors declare that they have no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yang, Y.X., Kang, M., An, X.Q. et al. Clean and Selective Oxidation of Alcohols with Oxone and Phase-Transfer Catalysts in Water. Russ J Org Chem 56, 1790–1794 (2020). https://doi.org/10.1134/S1070428020100206

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020100206

Keywords:

Search

Navigation