References

cpomaem

Коррозия: защита материалов и методы исследований

Title in english

ИФХЭ РАН

cpomaem-19

Research Article

Статьи

Ингибирование коррозии металла триазолами. Обзор

Metal Corrosion Inhibition by Triazoles: A Review

Meрими

И.

Merimi

LCAE, Fac Sci

B.P. 724, 60000 Oujda

LCAE, Fac Sci

B.P. 724, 60000 Oujda

Битари

А.

Bitari

Laboratory of Bioresources, Biotechnologies, Ethnopharmacology and Health, Department of Biology, Faculty of Sciences

Oujda

Laboratory of Bioresources, Biotechnologies, Ethnopharmacology and Health, Department of Biology, Faculty of Sciences

Oujda

Kaддоури

И.

Kaddouri

Laboratory of Inorganic Chemistry, Department of Chemistry

P.O. Box 55, FI-00014 Helsinki

Laboratory of Inorganic Chemistry, Department of Chemistry

P.O. Box 55, FI-00014 Helsinki

Резки

Н.

Rezki

Chemistry Department

P.O.Box 30002

Chemistry Department

P.O.Box 30002

Moхамед

М.

Mounir

LCAE, Fac Sci

B.P. 724, 60000 Oujda

LCAE, Fac Sci

B.P. 724, 60000 Oujda

Tоузани

Р.

Touzani

LCAE, Fac Sci

B.P. 724, 60000 Oujda

LCAE, Fac Sci

B.P. 724, 60000 Oujda

Хaммоути

Б.

Hammouti

LCAE, Fac Sci

Centre de Recherche (CREHEIO),

B.P. 724, 60000 Oujda

EHEI, 60000 Oujda

LCAE, Fac Sci

Centre de Recherche (CREHEIO),

B.P. 724, 60000 Oujda

EHEI, 60000 Oujda

b1.hammouti@ump.ac.ma

University Mohammed PremierМароккоUniversity Mohammed PremierMorocco

University of HelsinkiФинляндияUniversity of HelsinkiFinland

Taibah University Al Madinah MunawarahСаудовская АравияTaibah University Al Madinah MunawarahSaudi Arabia

University Mohammed Premier; Ecoles des Hautes Etudes d’IngénierieМароккоUniversity Mohammed Premier; Ecoles des Hautes Etudes d’IngénierieMorocco

2023

31102023

031736

2023

Meрими И., Битари А., Kaддоури И., Резки Н., Moхамед М., Tоузани Р., Хaммоути Б.

Merimi I., Bitari A., Kaddouri Y., Rezki N., Mounir M., Touzani R., Hammouti B.

Данная работа распространяется под лицензией Creative Commons Attribution 4.0.

This work is licensed under a Creative Commons Attribution 4.0 License.

https://www.cpmrm.ru/jour/article/view/19

Коррозия металлов и перспективы ингибирования этого процесса вызывают большой интерес со стороны общества и научных исследователей. Ежегодный глобальный ущерб от коррозии составляет 2,5 триллиона долларов США, что эквивалентно примерно 3,4% мирового валового внутреннего продукта. Внедрение передовых методов предотвращения коррозии может привести к глобальной экономии от 15 до 35% этих затрат. Многочисленные исследования, посвященные соединениям на основе триазолов, были проведены и показали, что они являются эффективными ингибиторами коррозии (ИК) различных металлов в агрессивных средах. Их уникальная электронная структура, обладающая сопряженными π-связями и не поделенными парами электронов на атомах азота, облегчает адсорбцию на металлических поверхностях. Таким образом, происходят физические и химические взаимодействия между активными центрами триазолов и d- орбиталями металлических материалов с образованием пленки на их поверхности. Природа ингибиторной активности раскрывается посредством поляризационных исследований (ИК катодного, анодного или смешанного типа). Набор различных заместителей в триазольном кольце обеспечивает широкий диапазон ингибирующих эффектов. Влияние температуры и концентрации ИК также необходимо учитывать при оценке параметров активации коррозии и адсорбции, что дополнительно подтверждается квантово-химическими расчетами, такими как DFT и моделированием молекулярной динамики (МД). В настоящем обзоре рассмотрены несколько примеров использования различных соединений, на основе замещенных триазолов в качестве эффективных ИК различных металлов в разных агрессивных средах.

Metal corrosion and the prospect of inhibiting this process have received much interest to society and scientific research. The annual global cost of corrosion is $2.5 trillion, equivalent to roughly 3.4% of the world's gross domestic product. Implementing corrosion prevention best practices could result in global savings of 15–35% of that cost. Great numbers of research were documented and dedicated on the triazole nucleus as fascinating corrosion inhibitors of various metals in hostile media, owing to their unique electronic structure possessing conjugated π and unshared pairs of electrons on the nitrogen atoms facilitates their adsorption on the metal surface. Thus, the physical and chemical interactions occurring between the active centers of triazoles and d-orbitals of metallic materials occurred to form a film on the surface. The nature of inhibitor activity is disclosed through polarization studies (cathodic, anodic or mixed-type). The range of various substituents on the triazole ring offers a vast array of inhibitory effects. Temperature and inhibitor concentration effects must also be regarded when evaluating the corrosion activation and adsorption parameters supported further by the quantum chemical parameters such as DFT and molecular dynamics simulations. In this review, we looked through several instances of the use of distinct substituted triazole nucleus as significant corrosion inhibitors for different metals in various aggressive media.

коррозияингибированиеметаллытриазолымоделирование

corrosioninhibitionmetalstriazolesDFTsimulation

References1

M. Lagrenée, B. Mernari, M. Bouanis, M. Traisnel and F. Bentiss, Study of the mechanism and inhibiting efficiency of 3,5-bis(4-methylthiophenyl)-4H-1,2,4-triazole on mild steel corrosion in acidic media, Corros. Sci., 2002, 44, no. 3, 573–588. doi: 10.1016/S0010-938X(01)00075-0

Y.G. Avdeev, Protection of metals in phosphoric acid solutions by corrosion inhibitors. Review, Int. J. Corros. Scale Inhib., 2019, 8, no. 4, 760–798. doi: 10.17675/2305-6894-2019-8-4-1

H.H. Hassan, E. Abdelghani and M.A. Amin, Inhibition of mild steel corrosion in hydrochloric acid solution by triazole derivatives. Part I. Polarization and EIS studies, Electrochim. Acta, 2007, 52, no. 22, 6359–6366. doi: 10.1016/j.electacta.2007.04.046

E. Abdullayev, R. Price, D. Shchukin and Y. Lvov, Halloysite tubes as nanocontainers for anticorrosion coating with benzotriazole, ACS Appl. Mater. Interfaces, 2009, 1, no. 7, 1437–1443.

K.R. Ansari, M.A. Quraishi and A. Singh, Schiff’s base of pyridyl substituted triazoles as new and effective corrosion inhibitors for mild steel in hydrochloric acid solution, Corros. Sci., 2014, 79, 5–15. doi: 10.1016/J.CORSCI.2013.10.009

K.F. Khaled, Molecular simulation, quantum chemical calculations and electrochemical studies for inhibition of mild steel by triazoles, Electrochim. Acta, 2008, 53, no. 9, 3484– 3492. doi: 10.1016/j.electacta.2007.12.030

O.A. Goncharova, A.Y. Luchkin, N.N. Andreev, N.P. Andreeva and S.S. Vesely, Triazole derivatives as chamber inhibitors of copper corrosion, Int. J. Corros. Scale Inhib., 2018, 7, no. 4, 657–672. doi: 10.17675/2305-6894-2018-7-4-12

S. Maddila, R. Pagadala and S. Jonnalagadda, 1,2,4-Triazoles: A Review of Synthetic Approaches and the Biological Activity, Lett. Org. Chem., 2013, 10, no. 10, 693–714.

L.P. Guan, Q.H. Jin, G.R. Tian, K.Y. Chai and Z.S. Quan, Synthesis of some quinoline2(1H)-one and 1,2,4-triazolo[4,3-a] quinoline derivatives as potent anticonvulsants, J. Pharm. Pharm. Sci., 2007, 10, no. 3, 254–262.

R. Gujjar, A. Marwaha, F.El Mazouni, J.K. White, K.L. White, S. Creason, D.M. Shackleford, J. Baldwin, W.N. Charman, F.S. Buckner, S. Charman, P.K. Rathod and M.A. Phillips, Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice, J. Med. Chem., 2009, 52, no. 7, 1864–1872. doi: 10.1021/jm801343r

M. Chen, S. Lu, G. Yuan, S. Yang and X. Du, Synthesis and Antibacterial Activity of some Heterocyclic β-Enamino Ester Derivatives with 1,2,3-triazole, Heterocycl. Commun., 2000, 6, no. 5, 421–426. doi: 10.1515/HC.2000.6.5.421

Y.A. Al-Soud, M.N. Al-Dweri and N.A. Al-Masoudi, Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives, Il Farmaco, 2004, 59, no. 10, 775–783.

M. Ur-Rahman, Y. Mohammad, K.M. Fazili, K.A. Bhat and T. Ara, Synthesis and biological evaluation of novel 3-O-tethered triazoles of diosgenin as potent antiproliferative agents, Steroids, 2017, 118, 1–8. doi: 10.1016/j.steroids

M. Huang, Z. Deng, J. Tian and T. Liu, Synthesis and biological evaluation of salinomycin triazole analogues as anticancer agents, Eur. J. Med. Chem., 2017, 127, 900–908. doi: 10.1016/j.ejmech.2016.10.067

K. Karrouchi, L. Chemlal, J. Taoufik, Y. Cherrah, S. Radi, M.El Abbes Faouzi and M. Ansar, Synthesis, antioxidant and analgesic activities of Schiff bases of 4- amino1,2,4-triazole derivatives containing a pyrazole moiety, Ann. Pharm. Fr., 2016, 74, no. 6, 431–438. doi: 10.1016/j.pharma.2016.03.005

C. Lass-Flörl, Triazole antifungal agents in invasive fungal infections: a comparative review, Drugs, 2011, 71, no. 18, 2405–2419.

S. Balabadra, M. Kotni, V. Manga, A.D. Allanki, R. Prasad and P.S. Sijwali, Synthesis and evaluation of naphthyl bearing 1,2,3-triazole analogs as antiplasmodial agents, cytotoxicity and docking studies, Bioorg. Med. Chem., 2017, 25, no. 1, 221–232. doi: 10.1016/j.bmc.2016.10.029

P. Khaligh, P. Salehi, M. Bararjanian, A. Aliahmadi, H.R. Khavasi and S.N. Ebrahimi, Synthesis and in Vitro Antibacterial Evaluation of Novel 4-Substituted 1-Menthyl-1,2,3- triazoles, Himalayan Chem. Pharm. Bull., 2016, 64, no. 11, 1589–1596.

T. Lee, M. Cho, S.Y. Ko, H.J. Youn, D.J. Baek, W.J. Cho, C.Y. Kang and S. Kim, Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant α-GalCer, J. Med. Chem., 2007, 50, no. 3, 585–589. doi: 10.1021/jm061243q

G. Wang, Z. Peng, J. Wang, X. Li and J. Li, Synthesis, in vitro evaluation and molecular docking studies of novel triazine-triazole derivatives as potential α-glucosidase inhibitors, Eur. J. Med. Chem., 2017, 125, 423–429. doi: 10.1016/j.ejmech.2016.09.067

P. Martins, J. Jesus, S.A. Santos, L.R. Raposo, C.R. Rodrigues, P.V. Baptista and A.R. Fernandes, Heterocyclic Anticancer Compounds: Recent Advances and the Paradigm Shift towards the Use of Nanomedicine’s Tool Box, Molecules, 2015, 20, no. 9, 16852–16891. doi: 10.3390/molecules200916852

I. Pibri and S. Buscemi, A Recent Portrait of Bioactive Triazoles, Curr. Bioact. Compd., 2010, 6, no. 4, 208–242. doi: 10.2174/157340710793237281

D.J. Harding, An Overview of Spin Crossover Nanoparticles, Novel Magn. Nanostruct., 2018, 401–426. doi: 10.1016/B978-0-12-813594-5.00012-6

A.R. Katritzky, P. Lue and K. Yannakopoulou, Side-chain elaboration with methyl iodide under lithiation conditions of α-benzotriazolylmethyl 1,2,4-triazole derivatives containing activated methylene groups have also been reported, Tetrahedron, 1990, 46, no. 2, 641–648.

I. Merimi, R. Benkaddour, H. Lgaz, N. Rezki, M. Messali, F. Jeffali, H. Oudda and B. Hammouti, Insights into corrosion inhibition behavior of a triazole derivative for mild steel in hydrochloric acid solution, Mater. Today: Proc., 2019, 13, 1008–1022. doi: 10.1016/J.MATPR.2019.04.066

I. Merimi, Y.El Ouadi, K.R. Ansari, H. Oudda, B. Hammouti, M.A. Quraishi, F. Faleh Al-blewi, N. Rezki, M.R. Aouad and M. Messali, Adsorption and Corrosion Inhibition of Mild Steel by ((Z)-4-((2,4-dihydroxybenzylidene)amino)-5-methy-2,4 dihydro-3H- 1,2,4-triazole-3-thione) in 1M HCl: Experimental and Computational Study, Anal. Bioanal. Electrochem., 2017, 9, no. 5, 640–659.

I. Merimi, Y.EL Ouadi, R. Benkaddour, H. Lgaz, M. Messali, F. Jeffali and B. Hammouti, Improving corrosion inhibition potentials using two triazole derivatives for mild steel in acidic medium: Experimental and theoretical studies, Mater. Today: Proc., 2019, 13, no. 3, 920–930. doi: 10.1016/j.matpr.2019.04.056

F. Bentiss, M. Lagrenee, M. Traisnel and J.C. Hornez, The Corrosion Inhibition of Mild Steel in Acidic Media by a New Triazole Derivative, Corros. Sci., 1999, 41, 789–803.

S. EL Issami, L. Bazzi, M. Hilali, R. Salghi and S. Kertit, Inhibition of copper corrosion in HCl 0.5 M medium by some triazolic compounds, Ann. Chim. Sci. Matér., 2002, 27, no. 4, 63–72.

H.L. Wang, R.B. Liu and J. Xin, Inhibiting effects of some mercaptotriazole derivatives on the corrosion of mild steel in 1.0M HCl medium, Corros. Sci., 2004, 46, 2455–2466. doi: 10.1016/j.corsci.2004.01.023

M.A. Quraishi, S. Ahmad and M.Q. Ansari, Inhibition of steel corrosion by some new triazole derivatives in boiling hydrochloric acid, Br. Corros. J., 1997, 32, 297–300. doi: 10.1179/000705997798129223

F. Xu and B. Hou, Triazole derivatives ascorrosion inhibitors for mild steel in hydrochloric acid solution, Acta Metall. Sin. (Engl. Lett.), 2009, 22, no. 4, 247–254. doi: 10.1016/S1006-7191(08)60096-4

Y. Qiang, S. Zhang, Q. Xiang, B. Tan, W. Li, S. Chen and L. Guo, Halogeno-substituted indazoles against copper corrosion in industrial pickling process: a combined electrochemical, morphological and theoretical approach, RSC Adv., 2018, 8, 38860– 38871. doi: 10.1039/C8RA08238C

G.O. Resende, S.F. Teixeira, I.F. Figueiredo, A.A. Godoy, D.J.F. Lougon, B.A. Cotrim, and F.C. Souza, Synthesis of 1,2,3-Triazole Derivatives and Its Evaluation as Corrosion Inhibitors for Carbon Steel, Int. J. Electrochem., 2019, doi: 10.1155/2019/6759478

Y.M. Tang, Y. Chen, W.Z. Yang, X.S. Yin, Y. Liu and J.T. Wang, 3,5‐Bis(2‐thienyl)‐4‐ amino‐1,2,4‐triazole as a corrosion inhibitor for copper in acidic media, Anti-Corros. Methods Mater., 2010, 57, 227–233. doi: 10.1108/00035591011075850

M.A. Quraishi and R. Sardar, Aromatic Triazoles as Corrosion Inhibitors for Mild Steel in Acidic Environments, Corrosion, 2002, 58, no. 9, 748–755. doi: 10.5006/1.3277657

I. Fichtali, W. Laaboudi, E.M.El Hadrami, F.El Aroussi, A. Ben-Tama, M. Benlemlih and S.E. Stiriba, Synthesis, characterization and antimicrobial activity of novel benzophenone derived 1,2,3-triazoles, J. Mater. Environ. Sci., 2016, 7, no. 5, 1633– 1641.

I. Elazhary, M.R. Laamari, A. Boutouil, L. Bahsis, M.El Haddad, H. Anane and S.E. Stiriba, Comparative study of 1,2,3-triazole derivatives as corrosion inhibitors of mild steel in sulphuric acid solution, Anti-Corros. Methods Mater., 2019, 66, 544–555. doi: 10.1108/acmm-10-2018-2018

S. John, J. Joy, M. Prajila and A. Joseph, Electrochemical, quantum chemical, and molecular dynamics studies on the interaction of 4-amino-4H,3,5-di(methoxy)-1,2,4- triazole (ATD), BATD, and DBATD on copper metal in 1N H2SO4, Mater. Corros., 2011, 62, no. 11, 1031–1041. doi: 10.1002/maco.201005938

M.E. Belghiti, Y. Karzazi, A. Dafali, I.B. Obot, E.E. Ebenso, K.M. Emran, I. Bahadur, B. Hammouti and F. Bentiss, Anti-corrosive properties of 4-amino-3,5- bis(disubstituted)-1,2,4-triazole derivatives on mild steel corrosion in 2 M H3PO4 solution: Experimental and theoretical studies, J. Mol. Liq., 2016, 216, 874–886. doi: 10.1016/j.molliq.2015.12.093

M. Lashgari, M.R. Arshadi and M. Biglar, Comparative Studies of Some Heterocyclic Compounds as Corrosion Inhibitors of Copper in Phosphoric Acid Media, Chem. Eng. Commun., 2010, 197, no. 10, 1303–1314. doi: 10.1080/00986441003622887

L.H. Madkour, S. Kaya and I.B. Obot, Computational, Monte Carlo simulation and experimental studies of some arylazotriazoles (AATR) and their copper complexes in corrosion inhibition process, J. Mol. Liq., 2018, 260, 351–374. doi: 10.1016/j.molliq.2018.01.055

Q.A. Jawad, A.Q. Hameed, M.K. Abood, A.A. Al-Amiery, L.M. Shaker, A.A.H. Kadhum and M.S. Takriff, Synthesis and comparative study of novel triazole derived as corrosion inhibitor of mild steel in HCl medium complemented with DFT calculations, Int. J. Corros. Scale Inhib., 2020, 9, no. 2, 688–705. doi: 10.17675/2305- 6894-2020-9-2-19

Yu.I. Kuznetsov, Triazoles as a class of multifunctional corrosion inhibitors. Review. Part II. 1,2,3-Benzotriazole and its derivatives. Iron and steels, Int. J. Corros. Scale Inhib., 2020, 9, no. 3, 780–811. doi: 10.17675/2305-6894-2020-9-3-1

Yu.I. Kuznetsov, Triazoles as a class of multifunctional corrosion inhibitors. A review. Part I. 1,2,3-Benzotriazole and its derivatives. Copper, zinc and their alloys, Int. J. Corros. Scale Inhib., 2018, 7, no. 3, 271–307. doi: 10.17675/2305-6894-2018-7-3-1

B. Jiang, S.L. Jiang, X. Liu, A.L. Ma and Y.G. Zheng, Corrosion Inhibition Performance of Triazole Derivatives on Copper-Nickel Alloy in 3.5 wt.% NaCl Solution, J. Mater. Eng. Perform., 2015, 24, no. 12, 4797–4808. doi: 10.1007/s11665-015-1759-8

M. Damej, D. Chebabe, S. Abbout, H. Erramli, A. Oubair and N. Hajjaji, Corrosion inhibition of brass 60Cu–40Zn in 3% NaCl solution by 3-amino-1,2,4-triazole-5-thiol, Heliyon, 2020, 6, no. 6, e04026. doi: 10.1016/j.heliyon.2020.e04026

El-S.M. Sherif, R.M. Erasmus and J.D. Comins, Corrosion of copper in aerated acidic pickling solutions and its inhibition by 3-amino-1,2,4-triazole-5-thiol, J. Colloid Interface Sci., 2006, 306, no. 1, 96–104. doi: 10.1016/j.jcis.2006.10.029

P.D.R. Kumari, J. Nayak and A.N. Shetty, 3-Methyl-4-amino-5-mercapto-1,2,4-triazole as corrosion inhibitor for 6061/Al-15(vol-%) SiC(p) composite in 0.5 M sodium hydroxide solution, J. Mater. Environ. Sci., 2011, 2, no. 4, 387–402.

A.Al Maofari, G. Ezznaydy, Y. Idouli, F. Guédira, S. Zaydoun, N. Labjar and S.El Hajjaji, Inhibitive action of 3,4'-bi-1,2,4-Triazole on the corrosion of copper in NaCl 3% solution, J. Mater. Environ. Sci., 2014, 5, no. 1, 2081–2085.

M.D. Plotnikova, A.D. Solovyev, A.B. Shein, A.N. Bakiev and A.S. Sofronov, New inhibitors based on substituted 1,2,4-triazoles for mild steel in hydrochloric acid solutions, Int. J. Corros. Scale Inhib., 2021, 10, no. 3, 1230–1244. doi: 10.17675/2305- 6894-2021-10-3-23

A. Zarrouk, B. Hammouti, S.S. Al-Deyab, R. Salghi, H. Zarrok, C. Jama and F. Bentiss, Corrosion inhibition performance of 3, 5-diamino-1, 2, 4-triazole for protection of copper in nitric acid solution, Int. J. Electrochem. Sci., 2012, 7, no. 7, 5997–6011.

A.S. Fouda, M.A. El-Morsi, M. Gaber and M. Fakeeh, A comparative study of the corrosion inhibition of carbon steel in HCl solution by 1‐[(5‐mercapto‐1H‐1,2,4‐triazole‐ 3‐yl) diazenyl] naphthalene‐2‐ol (HL) and its manganese complex, Chem. Data Collect., 2020, 28, 100479. doi: 10.1016/j.cdc.2020.100479

S.El Issami, L. Bazzi, A. Benlhachemi, R. Salghi, B. Hammouti and S. Kertit, Triazolic compounds as corrosion inhibitors for copper in hydrochloric acid, Pigm. Resin Technol., 2007, 36, no. 3, 161–168. doi: 10.1108/03699420710749027

B. El Ibrahimi, A. Soumoue, A. Jmiai, H. Bourzi, R. Oukhrib, K. El Mouaden, S. El Issami and L. Bazzi, Computational study of some triazole derivatives (un- and protonated forms) and their copper complexes in corrosion inhibition process, J. Mol. Struct., 2016, 1125, 93–102. doi: 10.1016/j.molstruc.2016.06.057

The authors declare that there are no conflicts of interest present.