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Kinetics and mechanism of the oxidation of vanillic acid using smectite clay

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Abstract

In this study, the oxidation of vanillic acid (VA) into protocatechuic acid (PCA) was investigated using montmorillonite KSF as inexpensive and environmentally benign solid acid, with peroxide hydrogen to afford excellent yields (more than 75%) endowed with high selectivity. To our knowledge, the aforementioned method was used for the first time in green, clean synthesis. The influence of the several operating parameters were performed using an experimental design Box–Behnken methodology. The progress of the concentrations of VA and its oxidation product PCA was accomplished using ultra-high-performance liquid chromatography coupled to quadrupole-time-of-flight mass spectrometry (RP-UHPLC-DAD-QTOF-MS) and mass spectrometry. Accordingly, PCA would be advantageous when used in food as well as cosmetic and pharmaceutical industries. Finally, a mechanistic pathway for the VA oxidation was proposed.

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Abbreviations

VA:

Vanillic acid

PCA:

Protocatechuic acid

LC–MS/MS:

Liquid chromatography coupled to mass spectrometry

BBD:

Box–Behnken design

RSM:

Response surface methodology

References

  1. Masella R, Santangelo C, D’archivio D et al (2012) Protocatechuic acid and human disease prevention: biological activities and molecular mechanisms. Curr Med Chem 19:2901–2917

    Article  CAS  Google Scholar 

  2. Azzini E, Vitaglione P, Intorre F et al (2010) Bioavailability of strawberry antioxidants in human subjects. Br J Nutr 104:1165–1173

    Article  CAS  Google Scholar 

  3. Khan AK, Rashid R, Fatima N et al (2015) Pharmacological activities of protocatechuic acid. Acta Pol Pharm 72:643–650

    CAS  PubMed  Google Scholar 

  4. Yang Y-C, Wei M-C, Lian F-Y, Huang T-C (2014) Simultaneous extraction and quantitation of oleanolic acid and ursolic acid from Scutellaria barbata D. Don by ultrasound-assisted extraction and high-performance liquid chromatography. Chem Eng Commun 201:482–500

    Article  CAS  Google Scholar 

  5. Irwin BY, Pearl A (1946) Reactions of vaillin and its derived compounds. The Caustic fusion of vaillin. J Am Chem Soc 68:2180–2184

    Article  Google Scholar 

  6. Rekik R, Hamza M, Jaziri M, Abdelhedi R (2017) Electrochemical oxidation of vanillic acid by electro-Fenton process: Toward a novel route of protocatechuic acid electrosynthesis. Arab J Chem. https://doi.org/10.1016/j.arabjc.2017.05.001

    Article  Google Scholar 

  7. Vyskočilová E, Gruberová A, Shamzhy M et al (2018) Prins cyclization in 4-methyl-2-phenyl-tetrahydro-2H-pyran-4-ol preparation using smectite clay as catalyst. React Kinet Mech Cat 124:711–725

    Article  Google Scholar 

  8. Neji SB, Azabou S, Contreras S et al (2016) Novel mild synthesis of high-added-value p-hydroxyphenyl acetic acid and 3, 4-dihydroxyphenyl acetic acid using the acidic clay/hydrogen peroxide catalytic system. Comptes Rendus Chim 19:286–292

    Article  Google Scholar 

  9. Frikha N, Bouguerra S, Kit G et al (2019) Smectite clay KSF as effective catalyst for oxidation of m-tyrosol with H2O2 to hydroxytyrosol. React Kinet Mech Cat 127:505–521

    Article  CAS  Google Scholar 

  10. Babuponnusami A, Muthukumar K (2013) A review on Fenton and improvements to the Fenton process for wastewater treatment. J Environ Chem Eng 186:16

    Google Scholar 

  11. Gümüş D, Akbal F (2016) Comparison of Fenton and electro-Fenton processes for oxidation of phenol. Process Saf Environ Prot 103:252–258

    Article  Google Scholar 

  12. Azabou S, Najjar W, Ghorbel A, Sayadi S (2007) Mild photochemical synthesis of the antioxidant hydroxytyrosol via conversion of tyrosol. J Agric Food Chem 55:4877–4882

    Article  CAS  Google Scholar 

  13. Bautista P, Mohedano AF, Casas JA et al (2008) An overview of the application of Fenton oxidation to industrial wastewaters treatment. J Chem Technol Biotechnol Int Res Process Environ Clean Technol 83:1323–1338

    CAS  Google Scholar 

  14. Box GE, Hunter JS, Hunter WG (2005) Statistics for experimenters: design, innovation, and discovery. Wiley-Interscience, New York

    Google Scholar 

  15. Lin Y, Xu W, Huang M et al (2015) Qualitative and quantitative analysis of phenolic acids, flavonoids and iridoid glycosides in Yinhua Kanggan tablet by UPLC-QqQ-MS/MS. Molecules 20:12209–12228

    Article  CAS  Google Scholar 

  16. Wójciak-Kosior M, Matysik G, Soczewiński E (2006) High-performance thin-layer chromatography combined with densitometry for quantitative analysis of phenolic acids in complex mixtures. JPC 19:21–26

    Google Scholar 

  17. Khoddami A, Wilkes MA, Roberts TH (2013) Techniques for analysis of plant phenolic compounds. Molecules 18:2328–2375

    Article  CAS  Google Scholar 

  18. Ammar S, del Mar Contreras M, Belguith-Hadrich O et al (2015) New insights into the qualitative phenolic profile of Ficus carica L. fruits and leaves from Tunisia using ultra-high-performance liquid chromatography coupled to quadrupole-time-of-flight mass spectrometry and their antioxidant activity. RSC Adv 5:20035–20050

    Article  CAS  Google Scholar 

  19. Kakkar S, Bais S (2014) A review on protocatechuic acid and its pharmacological potential. ISRN Pharmacol. https://doi.org/10.1155/2014/952943

    Article  PubMed  PubMed Central  Google Scholar 

  20. Qian Y, Goodell B, Felix CC (2002) The effect of low molecular weight chelators on iron chelation and free radical generation as studied by ESR measurement. Chemosphere 48:21–28

    Article  CAS  Google Scholar 

  21. Yamahara R, Ogo S, Masuda H, Watanabe Y (2002) (Catecholato) iron (III) complexes: structural and functional models for the catechol-bound iron (III) form of catechol dioxygenases. J Inorg Biochem 88:284–294

    Article  CAS  Google Scholar 

  22. Jovanovic SV, Simic MG, Steenken S, Hara Y (1998) Iron complexes of gallocatechins. Antioxidant action or iron regulation? J Chem Soc Perkin Trans 2:2365–2370

    Article  Google Scholar 

  23. Schweigert N, Zehnder AJ, Eggen RI (2001) Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals: minireview. Environ Microbiol 3:81–91

    Article  CAS  Google Scholar 

  24. Binbuga N, Chambers K, Henry WP, Schultz TP (2005) Metal chelation studies relevant to wood preservation. 1. Complexation of propyl gallate with Fe2+. Holzforschung 59:205–209

    Article  CAS  Google Scholar 

  25. Mijangos F, Varona F, Villota N (2006) Changes in solution color during phenol oxidation by Fenton reagent. Environ Sci Technol 40:5538–5543

    Article  CAS  Google Scholar 

  26. Hider RC, Howlin B, Miller JR et al (1983) Model compounds for microbial iron-transport compounds. Part IV. Further solution chemistry and Mössbauer studies on iron (II) and iron (III) catechol complexes. Inorg Chim Acta 80:51–56

    Article  CAS  Google Scholar 

  27. Contreras D, Freer J, Rodríguez J (2006) Veratryl alcohol degradation by a catechol-driven Fenton reaction as lignin oxidation by brown-rot fungi model. Int Biodeterior Biodegrad 57:63–68

    Article  CAS  Google Scholar 

  28. Tofan-Lazar J, Situm A, Al-Abadleh HA (2013) DRIFTS studies on the role of surface water in stabilizing catechol-iron (III) complexes at the gas/solid interface. J Phys Chem A 117:10368–10380

    Article  CAS  Google Scholar 

  29. Abdallah FB, Hmani E, Bouaziz M et al (2017) Recovery of hydroxytyrosol a high added value compound through tyrosol conversion by electro-Fenton process. Sep Purif Technol 188:260–265

    Article  Google Scholar 

  30. Joglekar AM, May AT, Graf E, Saguy I (1987) Product excellence through experimental design. Van Nostrsand Reinhold, New York, pp 211–229

    Google Scholar 

  31. Perincek S, Duran K (2016) Optimization of enzymatic & ultrasonic bio-scouring of linen fabrics by aid of Box–Behnken experimental design. J Clean Prod 135:1179–1188

    Article  CAS  Google Scholar 

  32. Ma L, Zhou M, Ren G et al (2016) A highly energy-efficient flow-through electro-Fenton process for organic pollutants degradation. Electrochim Acta 200:222–230

    Article  CAS  Google Scholar 

  33. Stasinakis AS (2008) Use of selected advanced oxidation processes (AOPs) for wastewater treatment–a mini review. Glob NEST J 10:376–385

    Google Scholar 

  34. Sirés I, Brillas E, Oturan MA et al (2014) Electrochemical advanced oxidation processes: today and tomorrow. A review. Environ Sci Pollut Res 21:8336–8367

    Article  Google Scholar 

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Acknowledgements

This research was supported by the Tunisian Ministry of Higher Education and Scientific Research (LR14ES08). We acknowledge the significant contribution of all the experts who participated in this study: M. Fatma Masmoudi for the experimental design

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Authors and Affiliations

  1. Laboratoire d’Electrochimie et Environnement, Ecole Nationale d’Ingénieurs de Sfax, Université de Sfax, BP1173, 3038, Sfax, Tunisia

    Nourzed Frikha, Soumaya Bouguerra, Sonda Ammar, Ridha Abdelhedi & Mohamed Bouaziz

  2. Departament d’Enginyeria Química, Universitat Rovira i Virgili Campus Sescelades, 43007, Tarragona, Spain

    Francisco Medina

Authors
  1. Nourzed Frikha
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  2. Soumaya Bouguerra
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  3. Sonda Ammar
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  4. Francisco Medina
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  5. Ridha Abdelhedi
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  6. Mohamed Bouaziz
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Correspondence to Mohamed Bouaziz.

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Frikha, N., Bouguerra, S., Ammar, S. et al. Kinetics and mechanism of the oxidation of vanillic acid using smectite clay. Reac Kinet Mech Cat 128, 903–916 (2019). https://doi.org/10.1007/s11144-019-01668-9

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  • DOI: https://doi.org/10.1007/s11144-019-01668-9

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