Log in

Polyethylene Glycols Catalyzed Reaction of Catechol and Resorcinol with Cerium Ammonium Sulfate in the Aqueous Medium: Kinetic and Mechanistic Study

  • Original Article
  • Published:
Chemistry Africa Aims and scope Submit manuscript

Abstract

The reaction kinetics of catechol or resorcinol with cerium (Ce) ammonium sulfate were spectrophotometrically investigated in polymer media containing polyethylene glycol (PEG 200, 600, 1500, and 4000). Kinetic runs for Ce(IV) were performed under pseudo-first-order reaction conditions. The reaction was found to be first-order for Ce(IV) and fractional orders for catechol, resorcinol, and H+. The presence of PEG caused considerable acceleration of the oxidation of the two substrates. Of note, PEG 4000 presents a distinguished catalytic activity when compared with PEG 200, 600, and 1500 in an acidic medium. The kinetic results were modeled using the Benesi–Hildebrand and Menger–Portnoy equations to explain the nature of the catalytic effects of both PEG forms and substrates. Hence, the efficiency of the reaction was optimal in the presence of resorcinol as a substrate. Based on kinetic features and thermodynamic parameters, probable mechanisms and expected final products are suggested and discussed.

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

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. Baciocchi E, Ruzziconi R (1986) 1,2- and 1,4-addition in the reactions of carbonyl compounds with 1,3-butadiene induced by cerium(IV) ammonium nitrate. J Org Chem 51:1645–1649. https://doi.org/10.1021/jo00360a002

    Article  CAS  Google Scholar 

  2. Paolobelli AB, Ceccherelli P, Pizzo RFRJ (1995) Regio- and stereoselective synthesis of unsaturated carbonyl compounds based on ceric ammonium nitrate-promoted oxidative addition of trimethylsilyl enol ethers to conjugated dienes. J Org Chem 60:4954–4958. https://doi.org/10.1021/jo00120a052

    Article  CAS  Google Scholar 

  3. Nair V, Mathew J (1995) Facile synthesis of dihydrofurans by the cerium(IV) ammonium nitrate mediated oxidative addition of 1,3-dicarbonyl compounds to cyclic and acyclic alkenes. Relative superiority over the manganese(III) acetate. J Chem Soc Perkin Trans 1(3):187–188. https://doi.org/10.1039/P19950000187

    Article  Google Scholar 

  4. Clark AJ, Dell CP, McDonagh JM, Geden J, Mawdsley P (2003) Oxidative 5-endo cyclization of enamides mediated by ceric ammonium nitrate. Org Lett 5:2063–2066. https://doi.org/10.1021/ol030045f

    Article  CAS  PubMed  Google Scholar 

  5. Agarwal A, Sharma G, Khandelwal CL, Sharma PD (2002) Kinetics and mechanism of oxidation of mannitol by sulphato-cerium(IV) species in aqueous acid medium. Inorg React Mech 4:233–239. https://doi.org/10.1080/1028662021000062617

    Article  CAS  Google Scholar 

  6. Kabir-ud-Din AMS, Khan Z (2005) Effect of surfactant micelles on the kinetics of oxidation of d-fructose by cerium(IV) in sulfuric acid medium. Int J Chem Kinet 38:18–25. https://doi.org/10.1002/kin.20132

    Article  CAS  Google Scholar 

  7. Kabir-ud-Din AMS, Khan Z (2005) Effect of anionic and cationic micelles on the oxidation of d-glucose by cerium(IV) in presence of H2SO4. Colloid Polym Sci 284:10–18. https://doi.org/10.1007/s00396-005-1301-x

    Article  CAS  Google Scholar 

  8. Yadav MB, Devra V, Rani A (2009) Kinetics and mechanism of silver(I) catalyzed oxidation of l-leucine by cerium (IV) in acid perchlorate medium. Phys Chem 4:21–26

    CAS  Google Scholar 

  9. Ghosh A, Saha R, Sar P, Saha B (2013) Rate enhancement via micelle encapsulation for room temperature metal catalyzed Ce(IV) oxidation of formaldehyde to formic acid in aqueous medium at atmospheric pressure: A kinetic approach. J Mol Liq 186:122–130. https://doi.org/10.1016/j.molliq.2013.07.003

    Article  CAS  Google Scholar 

  10. Hassan M, AlAhmadi MD, Mosaid M (2015) Micellar effect on the kinetics of oxidation of methyl blue by Ce(IV) in sulfuric acid medium. Arab J Chem 8(1):72–77. https://doi.org/10.1016/j.arabjc.2011.01.008

    Article  CAS  Google Scholar 

  11. Padhy RK, Sahu S (2021) Kinetic investigation of oxidation of alkanolamine by Cerium(IV) in acidic medium: catalytic effect of Mn(II). J Chem Sci 133:66. https://doi.org/10.1007/s12039-021-01921-6

    Article  CAS  Google Scholar 

  12. Shylaja S, Rajanna KC, Ramesh K, Rajendar Reddy K, Giridhar Reddy P (2013) Polyethylene glycols as efficient catalysts for the oxidation of xanthine alkaloids by ceric ammonium nitrate in acetonitrile: a kinetic and mechanistic approach. Adv Phys Chem 2013:1–11. https://doi.org/10.1155/2013/835610

    Article  CAS  Google Scholar 

  13. Rajitha N, Shylaja S, Rajanna KC, Yadagiri B (2018) Polyethylene glycols as efficient catalysts for the oxidation of bicyclic monoterpenes by ceric ammonium nitrate in acetonitrile under acid-free conditions: kinetic and mechanistic approach. Int J Chem Kinet 50:383–396. https://doi.org/10.1002/kin.21168

    Article  CAS  Google Scholar 

  14. Dahadha A, Hassan M, Al-Dhoun M, Batineh Y, Abu-Halawa M (2021) Kinetics of oxidation of aspirin by Ce(IV) in surfactant, polymer, and mixed surfactant-polymer media. Colloid Polym Sci. https://doi.org/10.1007/s00396-021-04849-y

    Article  Google Scholar 

  15. Dahadha AA, Hassan M, Mfarej T, Al-Dhoun M, Abunuwar M, Batineh Y (2021) The effect of mixed sodium dodecyl sulfate–polyethylene glycol systems on kinetic of oxidation of o Cresol by cerium(IV) in H2SO4 medium. Colloid Polym Sci. https://doi.org/10.1007/s00396-02204940-y

    Article  Google Scholar 

  16. Hassan M, Al-Dhoun M, Batineh Y, Najjar AA, Dahadha A, Ibrahim QA (2021) Micellar and polymer catalysis in the kinetics of xidation of l-lysine by permanganate ion in perchloric acid medium. S Afr J Chem 75:73–79. https://doi.org/10.17159/0379-4350/2021/v75a8

    Article  CAS  Google Scholar 

  17. Dahadha AA, Hassan M, Al Dhoun M, Mfarej T, Abunuwar M, Batineh Y (2021) The oxidation of salicylic acid and acetylsalicylic acid by water soluble colloidal manganese oxide in surfactant and polymer media: a kinetic and mechanistic approach. React Kinet Mech Catal 134:37–55. https://doi.org/10.1007/s11144-021-02083-9

    Article  CAS  Google Scholar 

  18. Subramaniam P, Selvi NT (2015) Dynamics of cetyltrimethylammonium bromide-mediated reaction of phenylsulfinylacetic acid with Cr(VI): treatment of pseudo-phase models. J Serb Chem Soc 80:1019–1034. https://doi.org/10.2298/JSC140916001S

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors wish to convey their sincere thanks to Philadelphia University in Jordan for successfully conducting the all kinetic runs in the scientific laboratory.

Funding

This research was carried out without any financial funds.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Adnan A. Dahadha.

Ethics declarations

Conflict of Interest

The authors have no conflicts of interest to declare that are relevant to the content of this article.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 302 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dahadha, A.A., Saadh, M.J., Mfarej, T. et al. Polyethylene Glycols Catalyzed Reaction of Catechol and Resorcinol with Cerium Ammonium Sulfate in the Aqueous Medium: Kinetic and Mechanistic Study. Chemistry Africa 5, 1417–1426 (2022). https://doi.org/10.1007/s42250-022-00436-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s42250-022-00436-y

Keywords

Navigation