Skip to main content
Log in

Synthesis and evaluation of bipyrazolic derivatives as inhibitors of corrosion of C38 steel in molar hydrochloric acid

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Methyl 2-(bis((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amino) acetate, BT36, and methyl 2-(bis((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amino)-3-(1H-indol-3-yl)propanoate, BT 43, have been synthesized. Investigation by weight-loss measurement and use of electrochemical techniques revealed the compounds are very effective inhibitors of corrosion of C38 steel in 1 M HCl solutions—percentage protection exceeded 95 % for BT43 at concentrations as low as 10−2 M. An impedance study in the absence and presence of these compounds revealed the mechanism of protection was cathodic inhibition by polarization and charge-transfer. The Langmuir adsorption isotherm was obeyed. Quantum chemical data calculated by use of DFT at the B3LYP/6-31G* level of theory revealed a good correlation between inhibition efficiency and the molecular structure of BT36 and BT43. The highest occupied molecular orbital, the lowest unoccupied molecular orbital, the separation energy (ΔE), and the dipole moment (μ) from the inhibitor to the metal surface explain the experimental data well.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Scheme 1
Fig. 9

Similar content being viewed by others

References

  1. N.O. Eddy, F.E. Awe, C.E. Gimba, N.O. Ibisi, E.E. Ebenso, Int. J. Electrochem. Sci. 6, 931 (2011)

    CAS  Google Scholar 

  2. L. Afia, R. Salghi, L. Bammou, L. Bazzi, B. Hammouti, Acta Metall. Sinica Engl. Lett. 25, 10 (2012)

    CAS  Google Scholar 

  3. K. Tebbji, A. Aouniti, A. Attayibat, B. Hammouti, H. Oudda, M. Benkaddour, S. Radi, A. Nahle, Indian J. Chem. Technol. 18, 244 (2011)

    CAS  Google Scholar 

  4. K. Tebbji, H. Oudda, B. Hammouti, M. Benkaddour, S.S. Al-Deyab, A. Aouniti, S. Radi, A. Ramdani, Res. Chem. Intermed. 37, 985 (2011)

    Article  CAS  Google Scholar 

  5. A. Zarrouk, B. Hammouti, R. Touzani, S.S. Al-Deyab, M. Zertoubi, A. Dafali, S. Elkadiri, Int. J. Electrochem. Sci. 6, 4939 (2011)

    CAS  Google Scholar 

  6. A. Chetouani, M. Daoudi, B. Hammouti, T. Ben Hadda, M. Benkaddour, Corros. Sci. 48, 2987 (2006)

    Article  CAS  Google Scholar 

  7. M. Benabdellah, A. Tounsi, K.F. Khaled, B. Hammouti, Arab. J. Chem. 4, 17 (2011)

    Article  CAS  Google Scholar 

  8. A. Chetouani, B. Hammouti, A. Aouniti, N. Benchat, T. Benhadda, Prog. Org. Coat. 45, 373 (2002)

    Article  CAS  Google Scholar 

  9. A. Chetouani, K. Medjahed, K.E. Benabadji, B. Hammouti, S. Kertit, A. Mansri, Prog. Org. Coat. 46, 312 (2003)

    Article  CAS  Google Scholar 

  10. B. Zerga, A. Attayibat, M. Sfaira, M. Taleb, B. Hammouti, M.E. Touhami, S. Radi, Z. Rais, J. Appl. Electrochem. 40, 1575 (2010)

    Article  CAS  Google Scholar 

  11. A.Y. Musa, A.A.H. Kadhum, M.S. Takriff, A. Mohamad, Int. J. Surf. Sci. Eng. 5, 226 (2011)

    Article  CAS  Google Scholar 

  12. S.P. Harrington, F. Wang, T.M. Devine, Electrochim. Acta 55, 4092 (2010)

    Article  CAS  Google Scholar 

  13. O.K. Abiola, M.O. John, P.O. Asekunowo, P.C. Okafor, O.O. James, Green Chem. Lett. Rev. 4, 273 (2011)

    Article  CAS  Google Scholar 

  14. P.D.R. Kumari, J. Nayak, A.N. Shetty, J. Coat. Technol. Res. 8, 685 (2011)

    Article  CAS  Google Scholar 

  15. A. Chetouani, B. Hammouti, T. Benhadda, M. Daoudi, Appl. Surf. Sci. 249, 375 (2005)

    Article  CAS  Google Scholar 

  16. A. Chetouani, K. Medjahed, K.E. Sid-Lakhdar, B. Hammouti, M. Benkaddour, A. Mansri, Corros. Sci. 46, 2421 (2004)

    Google Scholar 

  17. O. Senhaji, R. Taouil, M.K. Skalli, M. Bouachrine, B. Hammouti, M. Hamidi, S.S. Al-Deyab, Int. J. Electrochem. Sci. 6, 6290 (2011)

    CAS  Google Scholar 

  18. G. Thomas, N. Hammouti, A. Seitz, J. Shellfish Res. 30, 123 (2011)

    Article  Google Scholar 

  19. I. Warad, M. Azam, U. Karama, S. Al-Resayes, A. Aouissi, B. Hammouti, J. Mol. Struct. 1002, 107 (2011)

    Article  CAS  Google Scholar 

  20. A. Zarrouk, I. Warad, B. Hammouti, A. Dafali, S.S. Al-Deyab, N. Benchat, Int. J. Electrochem. Sci. 5, 1516 (2010)

    CAS  Google Scholar 

  21. F. Bentiss, C. Jama, B. Mernari, H. El Attari, L. El Kadi, M. Lebrini, M. Traisnel, M. Lagrenee, Corros. Sci. 51, 1628 (2009)

    Article  CAS  Google Scholar 

  22. A. Chetouani, B. Hammouti, Bull. Electrochem. 20, 343 (2004)

    CAS  Google Scholar 

  23. A. Chetouani, B. Hammouti, Bull. Electrochem. 19, 23 (2003)

    CAS  Google Scholar 

  24. M. Znini, M. Bouklah, L. Majidi, S. Kharchouf, A. Aouniti, A. Bouyanzer, B. Hammouti, J. Costa, S.S. Al-Dyab, Int. J. Electrochem. Sci. 6, 691 (2011)

    CAS  Google Scholar 

  25. A. Zarrouk, A. Dafali, B. Hammouti, H. Zarrok, S. Boukhris, M. Zertoubi, Int. J. Electrochem. Sci. 5, 46 (2010)

    CAS  Google Scholar 

  26. M. Bouklah, A. Attayibat, S. Kertit, A. Ramdani, B. Hammouti, Appl. Surf. Sci. 242, 399 (2005)

    Article  CAS  Google Scholar 

  27. L. Afia, R. Salghi, E. Bazzi, L. Bazzi, M. Errami, O. Jbara, S.S. Al-Deyab, B. Hammouti, Int. J. Electrochem. Sci. 6, 5918 (2011)

    CAS  Google Scholar 

  28. L. Bammou, M. Mihit, R. Salghi, A. Bouyanzer, S.S. Al-Deyab, L. Bazzi, B. Hammouti, Int. J. Electrochem. Sci. 6, 1454 (2011)

    CAS  Google Scholar 

  29. M. Benabdellah, A. Yahyi, A. Dafali, A. Aouniti, B. Hammouti, A. Ettouhami, Arab. J. Chem. 4, 243 (2011)

    Article  CAS  Google Scholar 

  30. F.Z. Bouanis, C. Jama, M. Traisnel, F. Bentiss, Corros. Sci. 52, 3180 (2010)

    Article  CAS  Google Scholar 

  31. L. Herrag, B. Hammouti, S. Elkadiri, A. Aouniti, C. Jama, H. Vezin, F. Bentiss, Corros. Sci. 52, 3042 (2010)

    Article  CAS  Google Scholar 

  32. A. Chetouani, A. Aouniti, B. Hammouti, N. Benchat, T. Benhadda, S. Kertit, Corros. Sci. 45, 1675 (2003)

    Article  CAS  Google Scholar 

  33. T. Mizuno, M. Kitaichi, Denki Kagaku 61, 589 (1993)

    CAS  Google Scholar 

  34. Y. Xu, H.W. Pickering, J. Electrochem. Soc. 140, 658 (1993)

    Article  CAS  Google Scholar 

  35. C. Deslouis, M.C. Lafont, N. Pebere, D. You, Corros. Sci. 34, 1567 (1993)

    Article  CAS  Google Scholar 

  36. N. Boussalah, R. Touzani, F. Souna, I. Himri, A. Hakkou, S. Ghalem, S. El Kadiri, J. Saoudi Chem. Soc. 10, 1016 (2011)

    Google Scholar 

  37. N. Boussalah, R. Touzani, I. Bouabdallah, S. El Kadiri, S. Ghalem, Int. J. Acad. Res. 2(1), 137 (2009)

    Google Scholar 

  38. T.K. Dong, A. Kirchev, F. Mattera, J. Kowal, Y. Bultel, J. Electrochem. Soc. 158, A326 (2011)

    Article  CAS  Google Scholar 

  39. K. Laarej, M. Bouachrine, S. Radi, S. Kertit, B. Hammouti, J. Chem. 7, 419 (2010)

    CAS  Google Scholar 

  40. K. Barouni, L. Bazzi, R. Salghi, M. Mihit, B. Hammouti, A. Albourine, S. El Issami, Mater. Lett. 62, 3325 (2008)

    Article  CAS  Google Scholar 

  41. A. Ouchrif, M. Zegmout, B. Hammouti, A. Dafali, M. Benkaddour, A. Ramdani, S. Elkadiri, Prog. Org. Coat. 53, 292 (2005)

    Article  CAS  Google Scholar 

  42. F. Bentiss, M. Lagrenee, M. Traisnel, B. Mernari, H. Elattari, J. Appl. Electrochem. 29, 1073 (1999)

    Article  CAS  Google Scholar 

  43. S. Kertit, B. Hammouti, Appl. Surf. Sci. 93, 59 (1996)

    Article  CAS  Google Scholar 

  44. M. Zerfaoui, B. Hammouti, H. Oudda, M. Benkaddour, S. Kertit, Bull. Electrochem. 20, 433 (2004)

    CAS  Google Scholar 

  45. M. Zerfaoui, H. Oudda, B. Hammouti, S. Kertit, M. Benkaddour, Prog. Org. Coat. 51, 134 (2004)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Chetouani.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Missoum, N., Guendouz, A., Boussalah, N. et al. Synthesis and evaluation of bipyrazolic derivatives as inhibitors of corrosion of C38 steel in molar hydrochloric acid. Res Chem Intermed 39, 3441–3461 (2013). https://doi.org/10.1007/s11164-012-0856-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0856-7

Keywords

Navigation