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A synergistic combination of SDS and TX-100 for the catalytic oxidation of an aromatic alcohol in aqueous media

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Abstract

In this experiment, an unexampled oxidation of an aromatic alcohol (4-chlorobenzyl alcohol) was carried out by Cr(VI) in aqueous mixed micellar medium under pseudo-first-order reaction condition at 30 °C. The spectrophotometric kinetic study exhibited excellent relative catalytic performances of micro-heterogeneous micellar aggregation in single and mixed micellar media (using anionic SDS and nonionic TX-100 surfactants). In the perspective of reaction rate control, the CMC of surfactants (in single or mixed micellar form) was explored to play a significant role. Herein two organic hetero-aromatic promoters, Phen and Bpy, were also used to scrutinize their effect on reaction dynamics in both the micellar media. The fabrication of mixed micelle was confirmed by UV, 1H NMR and 2D NOESY study.

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References

  1. H. Morawetz, Adv. Catal. 20, 341 (1969)

    CAS  Google Scholar 

  2. F. Rosati, J. Oelerich, G. Roelfes, Chem. Commun. 46, 7804 (2010)

    Article  CAS  Google Scholar 

  3. K. Bica, P. Gӓrtner, P.J. Gritsch, A.K. Ressmann, C. Schröder, R. Zirbs, Chem. Commun. 48, 5013 (2012)

    Article  CAS  Google Scholar 

  4. B.H. Lipshutz, B.R. Taft, Org. Lett. 10, 1329 (2008)

    Article  CAS  PubMed  Google Scholar 

  5. J.H.M. Heijnen, V.G. de Bruijn, L.J.P. van den Broeke, J.T.F. Keurentjes, Chem. Eng. Process. 42, 223 (2003)

    Article  CAS  Google Scholar 

  6. A. Acharjee, A. Rakshit, S. Chowdhury, B. Saha, J. Mol. Liq. 321, 114897 (2021)

    Article  CAS  Google Scholar 

  7. D.N. Rubingh, Mixed Micelle Solutions, in Solution Chemistry of Surfactants. ed. by K.L. Mittal (Springer, Boston, 1979)

    Google Scholar 

  8. M.N. Shalaby, J. Dispers. Sci. Technol. 29, 447 (2008)

    Article  CAS  Google Scholar 

  9. M.E. Haque, A.R. Das, A.K. Rakshit, S.P. Moulik, Langmuir 12, 4084 (1996)

    Article  CAS  Google Scholar 

  10. A. Gracia, M. Benghoulam, G. Marion, J. Lachaise, J. Phys. Chem. 93, 4167 (1989)

    Article  Google Scholar 

  11. M. Ishikawa, K. Matsumura, K. Esumi, K. Meguro, J. Colloid Interface Sci. 141, 10 (1991)

    Article  CAS  Google Scholar 

  12. B. Sohrabi, H. Gharibi, B. Tajik, S. Javadian, M. Hashemianzadeh, J. Phys. Chem. B 112, 14869 (2008)

    Article  CAS  PubMed  Google Scholar 

  13. A. Pal, A. Pillania, J. Mol. Liq. 212, 818 (2015)

    Article  CAS  Google Scholar 

  14. K. Sharma, S. Chauhan, Colloids Surf. A 453, 78 (2014)

    Article  CAS  Google Scholar 

  15. A.K. Tiwari, S.K. Saha, Ind. Eng. Chem. Res. 52, 5895 (2013)

    Article  Google Scholar 

  16. S. Kundu, P. Karmakar, S.M. Rahaman, M. Mitra, S. Rajwar, S. Dhibar, M. Layek, P. Sar, B. Saha, New J. Chem. 47, 4364 (2023)

    Article  CAS  Google Scholar 

  17. B. Chowdhury, S.M. Rahaman, A. Ghosh, K. Mahali, P. Sar, B. Saha, J. Mol. Liq. 368, 120817 (2022)

    Article  CAS  Google Scholar 

  18. F. Bukhtawar, M. Usman, N. Akram, A. Haq, Z. Ahmad, S. Raza, S. Younis, M.F. Nazar, Colloid. Polym. Sci. 300, 1205 (2022)

    Article  CAS  Google Scholar 

  19. T. Yaqoob, S. Shaukat, R. Alonaizan, R. Ullah, I. Khan, M.F. Nazar, H.M. Abd Ur Rahman, Molecules 28, 3952 (2023)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. S. Amjad, S. Shaukat, H.M. Abd Ur Rahman, M. Usman, Z.H. Farooqi, M.F. Nazar, J. Mol. Liq. 369, 120958 (2023)

    Article  CAS  Google Scholar 

  21. S. Irshad, H. Sultana, M. Usman, N. Akram, Z.H. Farooqi, A. Yusaf, M.F. Nazar, J. Dispers. Sci. Technol. 44, 1044 (2023)

    Article  CAS  Google Scholar 

  22. H. Zhang, D.L. Paul, J. Colloid Interface Sci. 186, 264 (1997)

    Article  CAS  PubMed  Google Scholar 

  23. T.Z. Wang, S.Z. Mao, X.J. Miao, S. Zhao, J.Y. Yu, Y.R. Du, J. Colloid Interface Sci. 241, 465 (2001)

    Article  CAS  Google Scholar 

  24. A. Rajewska, A.K. Islamov, R.F. Bakeeva, J. Phys. Conf. Ser. 994, 012015 (2018)

    Article  Google Scholar 

  25. A. Mal, S. Bag, S. Ghosh, S.P. Moulik, Colloids Surf. A Physicochem. Eng. Asp. 553, 633 (2018)

    Article  CAS  Google Scholar 

  26. X. Cui, Y. Jiang, C. Yang, X. Lu, H. Chen, S. Mao, M. Liu, H. Yuan, P. Luo, Y. Du, J. Phys. Chem. B 114, 7808 (2010)

    Article  CAS  PubMed  Google Scholar 

  27. P. Sar, A. Ghosh, S. Malik, B. Saha, Res. Chem. Intermed. 41, 10151 (2015)

    Article  CAS  Google Scholar 

  28. P. Sar, B. Saha, Adv. Colloid Interface Sci. 284, 102241 (2020)

    Article  CAS  PubMed  Google Scholar 

  29. S. Malik, D. Saha, M.H. Mondal, P. Sar, A. Ghosh, K. Mahali, B. Saha, J. Mol. Liq. 225, 207 (2017)

    Article  CAS  Google Scholar 

  30. A. Ghosh, R. Saha, K. Mukherjee, S.K. Ghosh, P. Sar, S. Malik, B. Saha, Res. Chem. Intermed. 41, 3057 (2015)

    Article  CAS  Google Scholar 

  31. K. Mukherjee, A. Ghosh, R. Saha, P. Sar, S. Malik, B. Saha, Spectrochim. Acta Part A 122, 204 (2014)

    Article  CAS  Google Scholar 

  32. R. Saha, A. Ghosh, P. Sar, I. Saha, S.K. Ghosh, K. Mukherjee, B. Saha, Spectrochim. Acta Part A 116, 524 (2013)

    Article  CAS  Google Scholar 

  33. W. Carruthers, I. Coldham, Modern methods of organic synthesis, 4th edn. (Cambridge University Press, Cambridge, 2004)

    Book  Google Scholar 

  34. A.K. Das, A. Roy, B. Saha, Transit. Met. Chem. 26, 630 (2001)

    Article  CAS  Google Scholar 

  35. B. Saha, M. Das, A. K. Das, J. Chem. Res. (S) 658 (2003)

  36. A. Rakshit, S. Chowdhury, A. Acharjee, I. Datta, K. Dome, S. Biswas, S.S. Bhattacharyya, B. Saha, Res. Chem. Intermed. 46, 2559 (2020)

    Article  CAS  Google Scholar 

  37. P. Sar, A. Ghosh, S. Malik, B. Saha, J. Carbohydr. Chem. 35, 86 (2016)

    Article  CAS  Google Scholar 

  38. B. Saha, M. Islam, A.K. Das, Inorg. React. Mech. 6, 141 (2006)

    CAS  Google Scholar 

  39. A. Ghosh, R. Saha, B. Saha, J. Ind. Eng. Chem. 20, 345 (2014)

    Article  CAS  Google Scholar 

  40. M. Budny, J. Włodarczyk, T. Muzioł, M.J. Bosiak, A. Wolan, Tetrahedron Lett. 58, 4285 (2017)

    Article  CAS  Google Scholar 

  41. Y. Todoroki, K. Kobayashi, H. Yoneyama, S. Hiramatsu, M. Jin, B. Watanabe, M. Mizutani, N. Hirai, Bioorg. Med. Chem. 16, 3141 (2008)

    Article  CAS  PubMed  Google Scholar 

  42. A. Majhi, S.S. Kim, H.S. Kim, Appl. Organomet. Chem. 22, 466 (2008)

    Article  CAS  Google Scholar 

  43. J. Clayden, N. Greeves, S. Warren, Organic Chemistry, 2nd edn. (Oxford University Press, New York, 2001), pp.138–140

    Google Scholar 

  44. S. Caron, Practical Synthetic Organic Chemistry: Reactions, Principles, and Techniques, 1st edn. (Wiley, New Jersey, 2011), pp.75–76

    Book  Google Scholar 

  45. C.L. Yuan, Z.Z. Xu, M.X. Fan, H.Y. Liu, Y.H. Xie, T. Zhu, J. Chem. Pharm. Res. 6, 2233 (2014)

    Google Scholar 

  46. L. Abu-Ghunmi, M. Badawi, M. Fayyad, J. Surfactant Deterg. 17, 833 (2014)

    Article  CAS  Google Scholar 

  47. P. Sar, A. Ghosh, S. Malik, D. Ray, B. Das, B. Saha, J. Ind. Eng. Chem. 42, 53 (2016)

    Article  CAS  Google Scholar 

  48. F.A. Cotton, G. Wilkinson, C.A. Murillo, M. Bochmann, Advanced Inorganic Chemistry, 6th edn. (Wiley, New York, 1999)

    Google Scholar 

  49. E. Perez-Benito, E. Rodenas, Langmuir 7, 232 (1991)

    Article  CAS  Google Scholar 

  50. A.K. Das, Coord. Chem. Rev. 248, 81 (2004)

    Article  CAS  Google Scholar 

  51. A. Acharjee, A. Rakshit, S. Chowdhury, M.A. Ali, B. Singh, B. Saha, J. Mol. Liq. 303, 112655 (2020)

    Article  Google Scholar 

  52. S. Chowdhury, A. Rakshit, A. Acharjee, B. Saha, ChemistrySelect 4, 6978 (2019)

    Article  CAS  Google Scholar 

  53. R. Saha, A. Ghosh, B. Saha, Chem. Eng. Sci. 99, 23 (2013)

    Article  CAS  Google Scholar 

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Acknowledgements

We are thankful to IIT(ISM) Dhanbad for instrumental support.

Funding

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Authors and Affiliations

  1. Surfactant Chemistry Laboratory, Department of Chemistry, The University of Burdwan, Burdwan, West Bengal, 713104, India

    Atanu Rakshit, Suman Chowdhury, Animesh Acharjee, Pintu Sar & Bidyut Saha

  2. Department of Chemistry, Hooghly Mohsin College, Chinsurah, West Bengal, 712101, India

    Animesh Acharjee

  3. Department of Chemistry, University of Kalyani, Kalyani, West Bengal, 741235, India

    Kalachand Mahali

  4. Department of Chemistry, Charuchandra College, Kolkata, West Bengal, 700029, India

    Rumpa Saha

  5. Polymer Research Centre, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, West Bengal, 741246, India

    Pintu Sar

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  1. Atanu Rakshit
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Contributions

All the authors have accepted responsibility for the entire content of this manuscript and approved submission. AR and BS have designed this work. SC and AA assisted AR to carry out experimental work. KM provided NMR facility. AR and BS wrote the manuscript. RS, BS, and PS modified and revised the whole manuscript.

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Correspondence to Pintu Sar or Bidyut Saha.

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Rakshit, A., Chowdhury, S., Acharjee, A. et al. A synergistic combination of SDS and TX-100 for the catalytic oxidation of an aromatic alcohol in aqueous media. Res Chem Intermed 49, 4025–4040 (2023). https://doi.org/10.1007/s11164-023-05061-z

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