Advertisement

Chemical, Electrochemical and Computational Studies of Newly Synthesized Novel and Environmental Friendly Heterocyclic Compounds as Corrosion Inhibitors for Mild Steel in Acidic Medium

  • Ankush Mishra
  • Chandrabhan Verma
  • V. Srivastava
  • H. Lgaz
  • M. A. Quraishi
  • Eno E. Ebenso
  • Ill-Min Chung
Article
  • 53 Downloads

Abstract

The present study describes the microwave-induced aqueous phase synthesis, characterization, and corrosion inhibition effect of five heterocyclics containing nitrogen, oxygen, and sulfur (designated by CINH-1 to CINH-5) for mild steel in 1 M HCl. The effectiveness of the newly synthesized heterocyclics has been evaluated using experimental and theoretical methods. Weight loss study revealed an increased effectiveness of the CINH molecules with increase in their concentrations and acquired the highest values of 82.38, 85.79, 88.93, 92.61, and 95.45% for CINH-1, CINH-2, CINH-3, CINH-4, and CINH-5, respectively, at 39.8 × 10−5 M concentration. Polarization study revealed that studied CINH molecules as cathodic-type inhibitors. EIS study showed that CINH molecules behave as interface type of corrosion inhibitors and enhance polarization resistances in their presence. Their adsorption at the interfaces obeyed the Temkin adsorption isotherm. The inhibition effect of the investigated CINH molecules was further supported by surface morphological studies using atomic force microscopy and scanning electron microscopy methods. Several DFT parameters such as ∆E, χ, η, σ, µ, and ∆N based on the values of frontier molecular energies (EHOMO and ELUMO) have been evaluated and employed to describe the inhibition action of the tested CINH molecules. Using MD simulations, orientation of the CINH molecules and adsorption energies for their interactions with metallic surface have been determined. Experimental and theoretical consequences were in good agreement.

Keywords

Green corrosion inhibitors Quinoxaline derivatives Temkin adsorption isotherm Computational simulations Surface investigation 

Notes

Acknowledgements

AM gratefully acknowledges MHRD, New Delhi (India) for providing financial supports and CIFC-IIT (BHU) Varanasi for providing instrumental facilities. CV thankfully acknowledges the North-West University, Mafikeng Campus, South Africa for providing financial supports under the postdoctoral fellowship scheme.

Supplementary material

40735_2018_147_MOESM1_ESM.docx (7.7 mb)
Supplementary material 1 (DOCX 7922 KB)

References

  1. 1.
    Gupta RK, Malviya M, Verma C, Quraishi M (2017) Aminoazobenzene and diaminoazobenzene functionalized graphene oxides as novel class of corrosion inhibitors for mild steel: experimental and DFT studies. Mater Chem Phys 198:360–373CrossRefGoogle Scholar
  2. 2.
    Verma C, Ebenso EE, Quraishi M (2017) Ionic liquids as green and sustainable corrosion inhibitors for metals and alloys: an overview. J Mol Liq 233:403–414CrossRefGoogle Scholar
  3. 3.
    Fu J, Zang H, Wang Y, Li S, Chen T, Liu X (2012) Experimental and theoretical study on the inhibition performances of quinoxaline and its derivatives for the corrosion of mild steel in hydrochloric acid. Ind Eng Chem Res 51:6377–6386CrossRefGoogle Scholar
  4. 4.
    Sappani HK, Karthikeyan S (2014) 4-Chloro-2-((furan-2-ylmethyl) amino)-5-sulfamoylbenzoic Acid (FSM) and N-(isopropylcarbamoyl)-4-(m-tolylamino) pyridine-3-sulfonamide (TSM) as potential Inhibitors for mild steel corrosion in 1 N H2SO4 medium. Part I. Ind Eng Chem Res 53:3415–3425CrossRefGoogle Scholar
  5. 5.
    Verma C, Olasunkanmi L, Ebenso EE, Quraishi M (2017) Corrosion inhibitors for ferrous and non-ferrous metals and alloys in ionic sodium chloride solutions: a review. J Mol Liq 248:927–942CrossRefGoogle Scholar
  6. 6.
    Varma R (1999) Solvent-free organic syntheses. using supported reagents and microwave irradiation. Green Chem, 1:43–55CrossRefGoogle Scholar
  7. 7.
    Kokel A, Török B (2017) Microwave-assisted solid phase diazotation: a method for the environmentally benign synthesis of benzotriazoles. Green Chem 19:2515–2519CrossRefGoogle Scholar
  8. 8.
    Mady AH, Baynosa ML, Tuma D, Shim J-J (2017) Facile microwave-assisted green synthesis of Ag-ZnFe2O4@rGO nanocomposites for efficient removal of organic dyes under UV- and visible-light irradiation. Appl Catal B 203:416–427CrossRefGoogle Scholar
  9. 9.
    He J, Zhou L, Liu J, Yang L, Zou L, Xiang J, Dong S, Yang X (2017) Modulation of surface structure and catalytic properties of cerium oxide nanoparticles by thermal and microwave synthesis techniques. Appl Surf Sci 402:469–477CrossRefGoogle Scholar
  10. 10.
    Dallinger D, Kappe CO (2007) Microwave-assisted synthesis in water as solvent. Chem Rev 107:2563–2591CrossRefGoogle Scholar
  11. 11.
    Gawande MB, Bonifácio VD, Luque R, Branco PS, Varma RS (2013) Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis. Chem Soc Rev 42:5522–5551CrossRefGoogle Scholar
  12. 12.
    Soliman DH (2013) Synthesis, characterization, anti-bacterial and anti-fungal activities of new quinoxaline 1, 4-di-N-oxide derivatives. Int J Org Chem 3:65–72CrossRefGoogle Scholar
  13. 13.
    Gu Z, Li Y, Ma S, Li S, Zhou G, Ding S, Zhang J, Wang S, Zhou C (2017) Synthesis, cytotoxic evaluation and DNA binding study of 9-fluoro-6H-indolo[2,3-b]quinoxaline derivatives. RSC Adv 7:41869–41879CrossRefGoogle Scholar
  14. 14.
    Yang Y-S, Li Q-S, Sun S, Zhang Y-B, Wang X-L, Zhang F, Tang J-F, Zhu H-L (2012) Design, modification and 3D QSAR studies of novel 2,3-dihydrobenzo[b][1,4]dioxin-containing 4,5-dihydro-1H-pyrazole derivatives as inhibitors of B-Raf kinase. Bioorg Med Chem 20:6048–6058CrossRefGoogle Scholar
  15. 15.
    Mohsen UA, Yurttaş L, Acar U, Özkay Y, Kaplacikli Z, Gencer HK, Cantürk Z (2015) Synthesis and biological evaluation of some new amide moiety bearing quinoxaline derivatives as antimicrobial agents. Drug Res 65:266–271Google Scholar
  16. 16.
    Schoenberg A, Singer E, Hoyer GA, Rosenberg D (1978) 1,2,3-Tricarbonyl compounds, XII. Elucidation of the constitution of the reaction products of ninhydrin with 2-aminophenol and 2-aminothiophenol. ChemInform 9:3058–3067Google Scholar
  17. 17.
    Simakov V, Kurbatov S, Borbulevych OY, Antipin MY, Olekhnovich L (2001) Structures of condensation products of ortho-aminophenols with ninhydrin. Russ Chem Bull 50:1064–1067CrossRefGoogle Scholar
  18. 18.
    Etman H, Metwally H, Elkasaby M, Khalil A, Metwally M (2011) Green, two components highly efficient reaction of ninhydrin with aromatic amines, and malononitrile using ball-milling technique. Am J Org Chem 1:10–13CrossRefGoogle Scholar
  19. 19.
    Mishra A, Verma C, Lgaz H, Srivastava V, Quraishi M, Ebenso EE (2018) Synthesis, characterization and corrosion inhibition studies of N-phenyl-benzamides on the acidic corrosion of mild steel: experimental and computational studies. J Mol Liq 251:317–332CrossRefGoogle Scholar
  20. 20.
    Verma C, Quraishi M, Kluza K, Makowska-Janusik M, Olasunkanmi LO, Ebenso EE (2017) Corrosion inhibition of mild steel in 1M HCl by D-glucose derivatives of dihydropyrido [2,3-d:6,5-d′] dipyrimidine-2, 4, 6, 8(1H,3H, 5H,7H)-tetraone. Sci Rep 7:44432CrossRefGoogle Scholar
  21. 21.
    Verma C, Olasunkanmi LO, Ebenso EE, Quraishi MA, Obot IB (2016) Adsorption behavior of glucosamine-based, pyrimidine-fused heterocycles as green corrosion inhibitors for mild steel: experimental and theoretical studies. J Phys Chem C 120:11598–11611CrossRefGoogle Scholar
  22. 22.
    Gao F, He J, Wu E, Liu S, Yu D, Li D, Zhang S, Tian Y (2003) Hardness of covalent crystals. Phys Rev Lett 91:015502CrossRefGoogle Scholar
  23. 23.
    Sun H (1998) COMPASS: an ab initio force-field optimized for condensed-phase applications overview with details on alkane and benzene compounds. J Phys Chem B 102:7338–7364CrossRefGoogle Scholar
  24. 24.
    Lgaz H, Salghi R, Bhat KS, Chaouiki A, Jodeh S (2017) Correlated experimental and theoretical study on inhibition behavior of novel quinoline derivatives for the corrosion of mild steel in hydrochloric acid solution. J Mol Liq 244:154–168CrossRefGoogle Scholar
  25. 25.
    Reichardt C, Welton T (2011) Solvents and solvent effects in organic chemistry. Wiley, New YorkGoogle Scholar
  26. 26.
    Behpour M, Mohammadi N (2012) Investigation of inhibition properties of aromatic thiol self-assembled monolayer for corrosion protection. Corros Sci 65:331–339CrossRefGoogle Scholar
  27. 27.
    Satapathy A, Gunasekaran G, Sahoo S, Amit K, Rodrigues P (2009) Corrosion inhibition by Justicia gendarussa plant extract in hydrochloric acid solution. Corros Sci 51:2848–2856CrossRefGoogle Scholar
  28. 28.
    Solmaz R, Şahin EA, Döner A, Kardaş G (2011) The investigation of synergistic inhibition effect of rhodanine and iodide ion on the corrosion of copper in sulphuric acid solution. Corros Sci 53:3231–3240CrossRefGoogle Scholar
  29. 29.
    Solmaz R, Mert M, Kardaş G, Yazici B, Erbil M (2008) Adsorption and corrosion inhibition effect of 1,1′-thiocarbonyldiimidazole on mild steel in h2so4 solution and synergistic effect of iodide ion. Acta Phys Chim Sin 24:1185–1191CrossRefGoogle Scholar
  30. 30.
    Singh AK, Quraishi M (2010) Effect of Cefazolin on the corrosion of mild steel in HCl solution. Corros Sci 52:152–160CrossRefGoogle Scholar
  31. 31.
    Avci G (2008) Corrosion inhibition of indole-3-acetic acid on mild steel in 0.5 M HCl. Colloids Surf A 317:730–736CrossRefGoogle Scholar
  32. 32.
    Badawi A, Hegazy M, El-Sawy A, Ahmed H, Kamel W (2010) Novel quaternary ammonium hydroxide cationic surfactants as corrosion inhibitors for carbon steel and as biocides for sulfate reducing bacteria (SRB). Mater Chem Phys 124:458–465CrossRefGoogle Scholar
  33. 33.
    Ahamad I, Prasad R, Quraishi M (2010) Adsorption and inhibitive properties of some new Mannich bases of Isatin derivatives on corrosion of mild steel in acidic media. Corros Sci 52:1472–1481CrossRefGoogle Scholar
  34. 34.
    Moussa M, El-Far A, El-Shafei A (2007) The use of water-soluble hydrazones as inhibitors for the corrosion of C-steel in acidic medium. Mater Chem Phys 105:105–113CrossRefGoogle Scholar
  35. 35.
    Rehim SSA, Hazzazi OA, Amin MA, Khaled KF (2008) On the corrosion inhibition of low carbon steel in concentrated sulphuric acid solutions. Part I: chemical and electrochemical (AC and DC) studies. Corros Sci 50:2258–2271CrossRefGoogle Scholar
  36. 36.
    Ashassi-Sorkhabi H, Seifzadeh D, Hosseini M (2008) EN, EIS and polarization studies to evaluate the inhibition effect of 3H-phenothiazin-3-one, 7-dimethylamin on mild steel corrosion in 1 M HCl solution. Corros Sci 50:3363–3370CrossRefGoogle Scholar
  37. 37.
    Hassan HH, Abdelghani E, Amin MA (2007) Inhibition of mild steel corrosion in hydrochloric acid solution by triazole derivatives: part I. Polarization and EIS studies. Electrochim Acta 52:6359–6366CrossRefGoogle Scholar
  38. 38.
    Bentiss F, Traisnel M, Lagrenee M (2000) The substituted 1,3,4-oxadiazoles: a new class of corrosion inhibitors of mild steel in acidic media. Corros Sci 42:127–146CrossRefGoogle Scholar
  39. 39.
    Ajmal M, Mideen A, Quraishi M (1994) 2-Hydrazino-6-methyl-benzothiazole as an effective inhibitor for the corrosion of mild steel in acidic solutions. Corros Sci 36:79–84CrossRefGoogle Scholar
  40. 40.
    Chauhan L, Gunasekaran G (2007) Corrosion inhibition of mild steel by plant extract in dilute HCl medium. Corros Sci 49:1143–1161CrossRefGoogle Scholar
  41. 41.
    Olasunkanmi LO, Obot IB, Kabanda MM, Ebenso EE (2015) Some quinoxalin-6-yl derivatives as corrosion inhibitors for mild steel in hydrochloric acid: experimental and theoretical studies. J Phys Chem C 119:16004–16019CrossRefGoogle Scholar
  42. 42.
    Singh P, Ebenso EE, Olasunkanmi LO, Obot I, Quraishi M (2016) Electrochemical, theoretical, and surface morphological studies of corrosion inhibition effect of green naphthyridine derivatives on mild steel in hydrochloric acid. J Phys Chem C 120:3408–3419CrossRefGoogle Scholar
  43. 43.
    Verma C, Olasunkanmi LO, Obot I, Ebenso EE, Quraishi M (2016) 2,4-Diamino-5-(phenylthio)-5H-chromeno [2,3-b] pyridine-3-carbonitriles as green and effective corrosion inhibitors: gravimetric, electrochemical, surface morphology and theoretical studie. RSC Adv 6:53933–53948CrossRefGoogle Scholar
  44. 44.
    Gupta NK, Verma C, Salghi R, Lgaz H, Mukherjee A, Quraishi M (2017) New phosphonate based corrosion inhibitors for mild steel in hydrochloric acid useful for industrial pickling processes: experimental and theoretical approach. New J Chem 41:13114–13129CrossRefGoogle Scholar
  45. 45.
    Saha SK, Ghosh P, Hens A, Murmu NC, Banerjee P (2015) Density functional theory and molecular dynamics simulation study on corrosion inhibition performance of mild steel by mercapto-quinoline Schiff base corrosion inhibitor. Physica E 66:332–341CrossRefGoogle Scholar
  46. 46.
    Haque J, Srivastava V, Verma C, Lgaz H, Salghi R, Quraishi M (2017) N-Methyl-N, N, N-trioctylammonium chloride as a novel and green corrosion inhibitor for mild steel in an acid chloride medium: electrochemical, DFT and MD studies. New J Chem 41:13647–13662CrossRefGoogle Scholar
  47. 47.
    Ofoegbu SU, Galvão TL, Gomes JR, Tedim J, Nogueira HI, Ferreira M, Zheludkevich M (2017) Corrosion inhibition of copper in aqueous chloride solution by 1H-1,2,3-triazole and 1,2,4-triazole and their combinations: electrochemical, Raman and theoretical studies. Phys Chem Chem Phys 19:6113–6129CrossRefGoogle Scholar
  48. 48.
    Singh AK, Thakur S, Pani B, Singh G (2018) Green synthesis and corrosion inhibition study of 2-amino-N’-(thiophen-2-yl) methylene) benzohydrazide. New J Chem 42:2113CrossRefGoogle Scholar
  49. 49.
    Lgaz H, Bhat KS, Salghi R, Jodeh S, Algarra M, Hammouti B, Ali IH, Essamri A (2017) Insights into corrosion inhibition behavior of three chalcone derivatives for mild steel in hydrochloric acid solution. J Mol Liq 238:71–83CrossRefGoogle Scholar
  50. 50.
    Hu S-Q, Guo A-L, Yan Y-G, Jia X-L, Geng Y-F, Guo W-Y (2011) Computer simulation of diffusion of corrosive particle in corrosion inhibitor membrane. Comput Theor Chem 964:176–181CrossRefGoogle Scholar
  51. 51.
    Yan Y, Wang X, Zhang Y, Wang P, Cao X, Zhang J (2013) Molecular dynamics simulation of corrosive species diffusion in imidazoline inhibitor films with different alkyl chain length. Corros Sci 73:123–129CrossRefGoogle Scholar
  52. 52.
    Obot I, Obi-Egbedi N, Ebenso E, Afolabi A, Oguzie E (2013) Experimental, quantum chemical calculations, and molecular dynamic simulations insight into the corrosion inhibition properties of 2-(6-methylpyridin-2-yl)oxazolo[5,4-f][1,10]phenanthroline on mild steel. Res Chem Intermed 39:1927–1948CrossRefGoogle Scholar
  53. 53.
    Zhou J, Chen S, Zhang L, Feng Y, Zhai H (2008) Studies of protection of self-assembled films by 2-mercapto-5-methyl-1, 3, 4-thiadiazole on iron surface in 0.1 M H2SO4 solutions. J Electroanal Chem 612:257–268CrossRefGoogle Scholar
  54. 54.
    Kokalj A (2013) Comments on the “reply to comments on the paper ’On the nature of inhibition performance of imidazole on iron surface’” by JO Mendes and AB Rocha. Corros Sci 70:294–297CrossRefGoogle Scholar
  55. 55.
    Liu A, Ren X, Zhang J, Wang C, Yang P, Zhang J, An M, Higgins D, Li Q, Wu G (2014) Theoretical and experimental studies of the corrosion inhibition effect of nitrotetrazolium blue chloride on copper in 0.1 M H2SO4. RSC Adv 4:40606–40616CrossRefGoogle Scholar
  56. 56.
    Singh A, Ansari K, Haque J, Dohare P, Lgaz H, Salghi R, Quraishi M (2018) Effect of electron donating functional groups on corrosion inhibition of mild steel in hydrochloric acid: experimental and quantum chemical study. J Taiwan Inst Chem Eng 82:233–251CrossRefGoogle Scholar

Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of ChemistryIndian Institute of Technology (Banaras Hindu University)VaranasiIndia
  2. 2.Department of Chemistry, Faculty of Natural and Agricultural Sciences, School of Chemical and Physical SciencesNorth-West UniversityMmabathoSouth Africa
  3. 3.Material Science Innovation & Modelling (MaSIM) Research Focus Area, Faculty of Natural and Agricultural SciencesNorth-West UniversityMmabathoSouth Africa
  4. 4.Department of Applied Bioscience, College of Life & Environment ScienceKonkuk UniversitySeoulSouth Korea
  5. 5.Center of Research Excellence in Corrosion, Research InstituteKing Fahd University of Petroleum & MineralsDhahranSaudi Arabia

Personalised recommendations