Synthesis, Characterization, and Electrochemical Study of Novel Porphyrin Derivatives as Corrosion Inhibitors for Carbon Steel in HCl Solutions
Mohammed Thamer Jaafar(1), Luma Majeed Ahmed(2*), Rahman Tama Haiwal(3)
(1) Department of Petroleum Engineering, College of Engineering, University of Kerbala, Karbala 56001, Iraq
(2) Department of Chemistry, College of Science, University of Kerbala, Karbala 56001, Iraq
(3) Department of Chemistry, College of Science, University of Kerbala, Karbala 56001, Iraq
(*) Corresponding Author
Abstract
This study involves the synthesis of some porphyrins derivatives, these are termed as 4,4',4'',4'''-(porphyrin-5,10,15,20-tetrayl)tetrakis(N-(6-aminoacridin-3-yl)benzamide) (3a), 4,4',4'',4'''-(porphyrin-5,10,15,20-tetrayl)tetrakis(N-(5-methoxybenzo[d]thiazol-2-yl)benzamide) (3b), 4,4'-(10,20-bis(3-hydroxyphenyl)porphyrin-5,15-diyl)bis(N-(6-aminoacridin-3yl)benzamide) (5a), and 4,4'-(10,20-bis(3-hydroxyphenyl)porphyrin-5,15-diyl)bis(N-(benzo[d]thiazol-2-yl)benzamide) (5b). These derivatives were synthesized using open circuit potential (OCP) and potentiodynamic polarization (PDP) in 0.1 M HCl solution methods. These derivatives were characterized using nuclear magnetic resonance (1H- and 13C-NMR) spectroscopy, mass spectra (ESI), and micro elemental analysis (CHN). The activity of these synthesized materials was investigated as a corrosion inhibitor using carbon steel (CS) as a model for corroded materials. The obtained results showed that the synthesized porphyrins derivatives were effective corrosion inhibitors to 0.1 M HCl solution for CS. In the case of the derivative 3a, a maximum inhibition efficiency (IE%) was recorded and it was around 74%. The derivative 3b showed an IE% of around 68.11%, while the %IE of 5a and 5b were around 18.98% and 45.16%, respectively. The best IE% value that was recorded for the derivative 3a has the potential to be effective anticorrosive coatings for industrial applications and act as mixture inhibitor because their ΔEcorr values are less than 85 mV. On the CS surface following treatment with compound 3a, the inhibitor mechanism for acidic medium (HCl) was investigated.
Keywords
References
[1] Fouda, A.S., Megahed, H.E., Fouad, N., and Elbahrawi, N.M., 2016, Corrosion inhibition of carbon steel in 1 M hydrochloric acid solution by aqueous extract of Thevetia peruviana, J. Bio- Tribo-Corros., 2 (3), 16.
[2] Avdeev, Y.G., Nenasheva, T.A., Luchkin, A.Y., Marshakov, A.I., and Kuznetsov, Y.I., 2023, Thin 1,2,4-triazole films for the inhibition of carbon steel corrosion in sulfuric acid solution, Coatings, 13 (7), 1221.
[3] Dwivedi, D., Lepková, K., and Becker, T., 2017, Carbon steel corrosion: A review of key surface properties and characterization methods, RSC Adv., 7 (8), 4580–4610.
[4] Fukaya, Y., and Watanabe, Y., 2018, Characterization and prediction of carbon steel corrosion in diluted seawater containing pentaborate, J. Nucl. Mater., 498, 159–168.
[5] Zhang, K., Xu, B., Yang, W., Yin, X., Liu, Y., and Chen, Y., 2015, Halogen-substituted imidazoline derivatives as corrosion inhibitors for mild steel in hydrochloric acid solution, Corros. Sci., 90, 284–295.
[6] Popoola, L.T., Grema, A.S., Latinwo, G.K., Gutti, B., and Balogun, A.S., 2013, Corrosion problems during oil and gas production and its mitigation, Int. J. Ind. Chem., 4 (1), 35.
[7] Onyeachu, I.B., Solomon, M.M., Umoren, S.A., Obot, I.B., and Sorour, A.A., 2020, Corrosion inhibition effect of a benzimidazole derivative on heat exchanger tubing materials during acid cleaning of multistage flash desalination plants, Desalination, 479, 114283.
[8] Al-Najjar, S.S., and Al-Baitai, A.Y., 2022, Synthesized of novel imidazole-derived Schiff base as a corrosion inhibitor of carbon steel in acidic medium supported by electrochemical and DFT studies, Phys. Chem. Res., 10 (2), 179–194.
[9] de Araújo Macedo, R.G.M., do Nascimento Marques, N., Tonholo, J., and de Carvalho Balaban, R., 2019, Water-soluble carboxymethyl chitosan used as corrosion inhibitor for carbon steel in saline medium, Carbohydr. Polym., 205, 371–376.
[10] Wei, W., Geng, S., Xie, D., and Wang, F., 2019, High temperature oxidation and corrosion behaviours of Ni–Fe–Cr alloys as inert anode for aluminum electrolysis, Corros. Sci., 157, 382–391.
[11] Ijaola, A.O., Farayibi, P.K., and Asmatulu, E., 2020, Superhydrophobic coatings for steel pipeline protection in oil and gas industries: A comprehensive review, J. Nat. Gas Sci. Eng., 83, 103544.
[12] Fonseca, A.C., Lopes, I.M., Coelho, J.F., and Serra, A.C., 2015, Synthesis of unsaturated polyesters based on renewable monomers: Structure/properties relationship and crosslinking with 2-hydroxyethyl methacrylate, React. Funct. Polym., 97, 1–11.
[13] Ansari, K.R., Chauhan, D.S., Singh, A., Saji, V.S., and Quraishi, M.A., 2020, “Corrosion Inhibitors for Acidizing Process in Oil and Gas Sectors” in Corrosion Inhibitors in the Oil and Gas Industry, Eds. Saji, V.S., and Umoren, S.A., Wiley‐VCH, Weinheim, Germany, 151–176.
[14] Migahed, M.A., El-Rabiei, M.M., Nady, H., Gomaa, H.M., and Zaki, E.G., 2017, Corrosion inhibition behavior of synthesized imidazolium ionic liquids for carbon steel in deep oil wells formation water, J. Bio- Tribo-Corros., 3 (2), 22.
[15] Ahamad, I., Prasad, R., and Quraishi, M.A., 2010, Thermodynamic, electrochemical and quantum chemical investigation of some Schiff bases as corrosion inhibitors for mild steel in hydrochloric acid solutions, Corros. Sci., 52 (3), 933–942.
[16] Mashuga, M.E., Olasunkanmi, L.O., Adekunle, A.S., Yesudass, S., Kabanda, M.M., and Ebenso, E.E., 2015, Adsorption, thermodynamic and quantum chemical studies of 1-hexyl-3-methylimidazolium based ionic liquids as corrosion inhibitors for mild steel in HCl, Materials, 8 (6), 3607–3632.
[17] Longo, F.R., De Luccia, J.J., and Agarwala, V.S., 1984, Porphyrins as Corrosion Inhibitors, Final Report, Naval Air Development Center, Warminster, Pennsylvania, US.
[18] Lokesh, K.S., De Keersmaecker, M., and Adriaens, A., 2012, Self assembled films of porphyrins with amine groups at different positions: Influence of their orientation on the corrosion inhibition and the electrocatalytic activity, Molecules, 17 (7), 7824–7842.
[19] Biesaga, M., Pyrzyńska, K., and Trojanowicz, M., 2000, Porphyrins in analytical chemistry. A review, Talanta, 51 (2), 209–224.
[20] Xiao, J., and Meyerhoff, M.E., 1996, Retention behavior of amino acids and peptides on protoporphyrin-silica stationary phases with varying metal ion centers, Anal. Chem., 68 (17), 2818–2825.
[21] Guan, Z., Li, H., Wei, Z., Shan, N., Fang, Y., Zhao, Y., Fu, L., Huang, Z., Humphrey, M.G., and Zhang, C., 2023, Enhanced nonlinear optical performance of perovskite films passivated by porphyrin derivatives, J. Mater. Chem. C, 11 (4), 1509–1521.
[22] Srivastava, M., 2023, Chemical facets of environment-friendly corrosion impediment of low-carbon steel in aqueous solutions of inorganic mineral acid, Sci. Temper, 14 (2), 284–287.
[23] Furtado, L.B., Leoni, G.B., Nascimento, R.C., Santos, P.H.C., Henrique, F.J., Guimarães, M.J.O.C., and Brasil, S.L.D.C., 2023, Experimental and theoretical studies of tailor-made Schiff bases as corrosion inhibitors for carbon steel in HCl, Mater. Res., 26, e20220398.
[24] Orozco-Agamez, J., Alviz-Meza, A., Kafarov, V., Colpas, F., Jimenez, M., and Pena-Ballesteros, D., 2023, Natural polymers as green corrosion inhibitors in carbon steels for applications in acid environment, Chem. Eng. Trans., 100, 109–114.
[25] Benmahammed, I., Douadi, T., Issaadi, S., Al-Noaimi, M., and Chafaa, S., 2020, Heterocyclic Schiff bases as corrosion inhibitors for carbon steel in 1 M HCl solution: Hydrodynamic and synergetic effect, J. Dispersion Sci. Technol., 41 (7), 1002–1021.
[26] Fratilescu, I., Lascu, A., Taranu, B.O., Epuran, C., Birdeanu, M., Macsim, A.M., Tanasa, E., Vasile, E., and Fagadar-Cosma, E., 2022, One A3B porphyrin structure—Three successful applications, Nanomaterials, 12 (11), 1930.
[27] Jayaprakash, G.K., Kumara Swamy, B.E., Rajendrachari, S., Sharma, S.C., and Flores-Moreno, R., 2021, Dual descriptor analysis of cetylpyridinium modified carbon paste electrodes for ascorbic acid sensing applications, J. Mol. Liq., 334, 116348.
[28] Wolfram, A., Tariq, Q., Fernández, C.C., Muth, M., Gurrath, M., Wechsler, D., Franke, M., Williams, F.J., Steinrück, H.P., Meyer, B., and Lytken, O., 2022, Adsorption energies of porphyrins on MgO(100): An experimental benchmark for dispersion-corrected density-functional theory, Surf. Sci., 717, 121979.
[29] Singh, A., Lin, Y., Quraishi, M.A., Olasunkanmi, L.O., Fayemi, O.E., Sasikumar, Y., Ramaganthan, B., Bahadur, I., Obot, I.B., Adekunle, S.A., Kabanda, M.M., and Ebenso, E.E., 2015, Porphyrins as corrosion inhibitors for N80 steel in 3.5% NaCl solution: Electrochemical, quantum chemical, QSAR and Monte Carlo simulations studies, Molecules, 20 (8), 15122–15146.
[30] Leggio, A., Belsito, E.L., De Luca, G., Di Gioia, M.L., Leotta, V., Romio, E., Siciliano, C., and Liguori, A., 2016, One-pot synthesis of amides from carboxylic acids activated using thionyl chloride, RSC Adv., 6 (41), 34468–34475.
[31] Jaafar, M.T., Ahmed, L.M., and Haiwal, R.T., 2023, Synthesis of novel porphyrin derivatives and investigate their application in sensitized solar cells, Iraqi J. Chem. Pet. Eng., 24 (2), 113–122.
[32] Kotteswaran, S., Mohankumar, V., Pandian, M.S., and Ramasamy, P., 2017, Effect of dimethylaminophenyl and thienyl donor groups on Zn-Porphyrin for dye sensitized solar cell (DSSC) applications, Inorg. Chim. Acta, 467, 256–263.
[33] Hussien, H., Shahen, S., Abdel-karim, A.M., Ghayad, I.M., El-Shamy, O.A.A., Mostfa, N., and Ahmed, N.E.D., 2023, Experimental and theoretical evaluations: Green synthesis of new organic compound bis ethanethioyl oxalamide as corrosion inhibitor for copper in 3.5% NaCl, Egypt. J. Chem., 66 (3), 189–196.
[34] Deyab, M.A., Mele, G., Al-Sabagh, A.M., Bloise, E., Lomonaco, D., Mazzetto, S.E., and Clemente, C.D., 2017, Synthesis and characteristics of alkyd resin/M-Porphyrins nanocomposite for corrosion protection application, Prog. Org. Coat., 105, 286–290.
[35] Khalib, A.A.K., Al-Hazam, H.A.J., and Hassan, A.F., 2022, Inhibition of carbon steel corrosion by some new organic 2-hydroselenoacetamide derivatives in HCl medium, Indones. J. Chem., 22 (5), 1269–1281.
[36] Salleh, N.I.H., and Abdullah, A., 2019, Corrosion inhibition of carbon steel using palm oil leaves extract, Indones. J. Chem., 19 (3), 747–752.
[37] Verma, D.K., Ebenso, E.E., Quraishi, M.A., and Verma, C., 2019, Gravimetric, electrochemical surface and density functional theory study of acetohydroxamic and benzohydroxamic acids as corrosion inhibitors for copper in 1 M HCl, Results Phys., 13, 102194.
[38] Dagdag, O., El Harfi, A., Cherkaoui, O., Safi, Z., Wazzan, N., Guo, L., Verma, C., Ebenso, E.E., and Jalgham, R.T.T., 2019, Rheological, electrochemical, surface, DFT and molecular dynamics simulation studies on the anticorrosive properties of new epoxy monomer compound for steel in 1 M HCl solution, RSC Adv., 9 (8), 4454–4462.
[39] Roberge, P.R., 2019, Handbook of Corrosion Engineering, 3rd Ed., McGraw-Hill Education, New York, US.
[40] Desai, P.D., Pawar, C.B., Avhad, M.S., and More, A.P., 2023, Corrosion inhibitors for carbon steel: A review, Vietnam J. Chem., 61 (1), 15–42.
[41] Lgamri, A., Abou El Makarim, H., Guenbour, A., Ben Bachir, A., Aries, L., and El Hajjaji, S., 2003, Electrochemical study of the corrosion behaviour of iron in presence of new inhibitor in 1 M HCl, Prog. Org. Coat., 48 (1), 63–70.
[42] Vinutha, M.R., and Venkatesha, T.V., 2016, Review on mechanistic action of inhibitors on steel corrosion in acidic media, Port. Electrochim. Acta, 34 (3), 157–184.
[43] Alesary, H.F., Ismail, H.K., Shiltagh, N.M., Alattar, R.A., Ahmed, L.M., Watkins, M.J., and Ryder, K.S., 2020, Effects of additives on the electrodeposition of ZnSn alloys from choline chloride/ethylene glycol-based deep eutectic solvent, J. Electroanal. Chem., 874, 114517.
[44] Elewady, G.Y., 2008, Pyrimidine derivatives as corrosion inhibitors for carbon-steel in 2M hydrochloric acid solution, Int. J. Electrochem. Sci., 3 (10), 1149–1161.
[45] Muralidharan, S., Quraishi, M.A., and Iyer, S.V.K., 1995, The effect of molecular structure on hydrogen permeation and the corrosion inhibition of mild steel in acidic solutions, Corros. Sci., 37 (11), 1739–1750.
[46] Verma, C., Lgaz, H., Verma, D.K., Ebenso, E.E., Bahadur, I., and Quraishi, M.A., 2018, Molecular dynamics and Monte Carlo simulations as powerful tools for study of interfacial adsorption behavior of corrosion inhibitors in aqueous phase: A review, J. Mol. Liq., 260, 99–120.
[47] Chen, L., Lu, D., and Zhang, Y., 2022, Organic compounds as corrosion inhibitors for carbon steel in HCl solution: A comprehensive review, Materials, 15 (6), 2023.
DOI: https://doi.org/10.22146/ijc.87682
Article Metrics
Abstract views : 2187 | views : 1082 | views : 689Copyright (c) 2023 Indonesian Journal of Chemistry
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.
View The Statistics of Indones. J. Chem.