Abstract
Imidazoline and imidazoline derivatives are extensively employed as effective corrosion inhibitors due to their low toxicity, low cost and environmental friendliness. Their chemical structure consists of a 5-membered heterocyclic ring (C3N2H4) with two nitrogen atoms that are readily adsorbed onto metal surfaces. Also, a pendant side chain or alkyl amine substituent acts as an anchor that helps to maintain its adsorption on steel surfaces. The tail portion is a long hydrocarbon chain that can form a hydrophobic film on a surface. These molecular structures make it very attractive as a starting point for several enhancements in corrosion inhibition research. Moreover, modification of an imidazoline structure can be more effective in enhancing its effectiveness in corrosion inhibition. This review compiled all information regarding imidazoline and imidazoline derivatives used as effective corrosion inhibitors in the petroleum industry. It includes their chemical structures and properties, synthesis processes, characterisation and performance evaluations. The review also gives an overview of various types of imidazoline inhibitors with their preparation processes, metal types, corrosive media and concentration range for measurements.
Funding source: National Energy Technology Center (ENTEC), National Science and Technology Development Agency
About the authors
Nipaporn Sriplai received a PhD degree in material science and nanotechnology from Khon Kaen University, Thailand. Presently, she works as a postdoctoral researcher at National Energy Technology Center (ENTEC), National Science and Technology Development Agency (NSTDA), Thailand. Her research interests lie in the development of corrosion inhibitor formulations to prevent corrosion in gas pipelines and synthesis of corrosion inhibition compounds.
Korakot Sombatmankhong received a PhD in chemical engineering from of University of Cambridge, UK. Currently, she is a senior researcher at National Energy Technology Center (ENTEC), National Science and Technology Development Agency (NSTDA), Thailand. She has more than 10 years of research experience on chemical deformulation/formulation, polymer gel electrolyte, fuel cells, organic synthesis and arsenic/mercury removal. She has been working in several industry-sponsored research projects, such as the development of corrosion inhibition formulation, imidazoline synthesis and pipeline decommissioning processes.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: This work was supported by National Energy Technology Center (ENTEC), National Science and Technology Development Agency (NSTDA).
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
Abd El-Lateef, H.M., Shalabi, K., and Abdelhamid, A.A. (2021). One-pot synthesis of novel triphenyl hexyl imidazole derivatives catalyzed by ionic liquid for acid corrosion inhibition of C1018 steel: experimental and computational perspectives. J. Mol. Liq. 334: 116081, https://doi.org/10.1016/j.molliq.2021.116081.Search in Google Scholar
Abd El-Lateef, H.M., Maharram, A.A., Leylufer, I., and Ismayilov, T.A. (2012). Corrosion protection of steel pipelines against CO2 corrosion-a review. Chem. J. 2: 52–63.Search in Google Scholar
Agrawal, A.K. (2001). Corrosion monitoring. In: Buschow, K.H.J., Cahn, R.W., Flemings, M.C., Ilschner, B., Kramer, E.J., Mahajan, S., and Veyssière, P. (Eds.), Encyclopedia of materials: science and technology. Elsevier, Oxford.Search in Google Scholar
Al-Moubaraki, A.H. and Obot, I.B. (2021). Corrosion challenges in petroleum refinery operations: sources, mechanisms, mitigation, and future outlook. J. Saudi Chem. Soc. 25: 101370, https://doi.org/10.1016/j.jscs.2021.101370.Search in Google Scholar
Alaoui, K., Dkhireche, N., Touhami, M.E., and El Kacimi, Y. (2020). Review of application of imidazole and imidazole derivatives as corrosion inhibitors of metals. In: New Challenges and Industrial Applications for Corrosion Prevention and Control. IGI Global, United States.10.4018/978-1-7998-2775-7.ch005Search in Google Scholar
Alhaffar, M., Umoren, S., Obot, I., and Ali, S. (2018). Isoxazolidine derivatives as corrosion inhibitors for low carbon steel in HCl solution: experimental, theoretical and effect of KI studies. RSC Adv. 8: 1764–1777, https://doi.org/10.1039/c7ra11549k.Search in Google Scholar PubMed PubMed Central
Angst, U.M. and Büchler, M. (2016). Corrosion rate measurements in concrete-a closer look at the linear polarization resistance method. In: Dehn, F., Beushausen, H.-D., Alexander, M.G., Moyo, P. (Eds.), Concrete repair, rehabilitation and retrofitting IV. Taylor & Francis Group, London, pp. 198–199.10.1201/b18972-125Search in Google Scholar
Ansari, K.R., Quraishi, M.A., Singh, A., Ramkumar, S., and Obote, I.B. (2016). Corrosion inhibition of N80 steel in 15% HCl by pyrazolone derivatives: electrochemical, surface and quantum chemical studies. RSC Adv. 6: 24130–24141, https://doi.org/10.1039/c5ra25441h.Search in Google Scholar
Arya, S.B. and Joseph, F.J. (2021). Electrochemical methods in tribocorrosion. In: Siddaiah, A., Ramachandran, R., and Menezes, P.L. (Eds.), Tribocorrosion, Chapter 3. Academic Press, United States.Search in Google Scholar
Bajpai, D. and Tyagi, V.K. (2006). Fatty imidazolines: chemistry, synthesis, properties and their industrial applications. J. Oleo Sci. 55: 319–329, https://doi.org/10.5650/jos.55.319.Search in Google Scholar
Bajpai, D. and Tyagi, V.K. (2008). Microwave synthesis of cationic fatty imidazolines and their characterization. J. Surfactants Deterg. 11: 79–87, https://doi.org/10.1007/s11743-007-1057-z.Search in Google Scholar
Bereket, G., Hür, E., and Öğretir, C. (2002). Quantum chemical studies on some imidazole derivatives as corrosion inhibitors for iron in acidic medium. J. Mol. Struct. Theochem 578: 79–88, https://doi.org/10.1016/S0166-1280(01)00684-4.Search in Google Scholar
Budiana, S., Andreana, B., Rahayu, D.U.C., Nurani, D.A., Krisnandi, Y.K., and Budianto, E. (2020). Synthesis of imidazoline-palmitic derivative using MAOS (microwave assisted organic synthesis) method. IOP Conf. Ser. Mater. Sci. Eng. 763: 012006, https://doi.org/10.1088/1757-899x/763/1/012006.Search in Google Scholar
Demirbas, A. (2008). Production of biodiesel from tall oil. Energy Sources, Part A Recovery, Util. Environ. Eff. 30: 1896–1902, https://doi.org/10.1080/15567030701468050.Search in Google Scholar
Desimone, M.P., Gordillo, G., and Simison, S.N. (2011). The effect of temperature and concentration on the corrosion inhibition mechanism of an amphiphilic amido-amine in CO2 saturated solution. Corrosion Sci. 53: 4033–4043, https://doi.org/10.1016/j.corsci.2011.08.009.Search in Google Scholar
Ditama, I., Muktiarti, N., and Soegijono, B. (2020). Imidazoline derivatives based on silane functional group as corrosion inhibitor on mild steel. AIP Conf. Proc. 2242: 020019.10.1063/5.0007979Search in Google Scholar
El-Katori, E.E., Ahmed, M., and Nady, H. (2022). Imidazole derivatives based on glycourils as efficient anti-corrosion inhibitors for copper in HNO3 solution: synthesis, electrochemical, surface, and theoretical approaches. Colloids Surf. A Physicochem. Eng. Asp. 649: 129391, https://doi.org/10.1016/j.colsurfa.2022.129391.Search in Google Scholar
Fazal, B.R., Becker, T., Kinsella, B. and Lepkova, K. (2022). A review of plant extracts as green corrosion inhibitors for CO2 corrosion of carbon steel. NPJ Mater. Degrad. 6: 5, https://doi.org/10.1038/s41529-021-00201-5.Search in Google Scholar
Ferm, R.J. and Riebsomer, J.L. (1954). The chemistry of the 2-imidazolines and imidazolidines. Chem. Rev. 54: 593–613, https://doi.org/10.1021/cr60170a002.Search in Google Scholar
Fuchs-Godec, R. (2006). The adsorption, CMC determination and corrosion inhibition of some N-alkyl quaternary ammonium salts on carbon steel surface in 2M H2SO4. Colloids Surf. A Physicochem. Eng. Asp. 280: 130–139, https://doi.org/10.1016/j.colsurfa.2006.01.046.Search in Google Scholar
Geng, S., Hu, J., Yu, J., Zhang, C., Wang, H., and Zhong, X. (2022). Rosin imidazoline as an eco-friendly corrosion inhibitor for the carbon steel in CO2-containing solution and its synergistic effect with thiourea. J. Mol. Struct. 1250: 131778, https://doi.org/10.1016/j.molstruc.2021.131778.Search in Google Scholar
Guo, W., Talha, M., Lin, Y., Ma, Y., and Kong, X. (2021). Effect of phosphonate functional group on corrosion inhibition of imidazoline derivatives in acidic environment. J. Colloid Interface Sci. 597: 242–259, https://doi.org/10.1016/j.jcis.2021.02.131.Search in Google Scholar PubMed
Hadjichristov, G.B., Marinov, Y.G., Vlakhov, T.E., and Scaramuzza, N. (2021). Phospholipid Langmuir-Blodgett nano-thin monolayers: electrical response to cadmium ions and harmful volatile organic compounds. In: Iglič, A., Rappolt, M., and García-Sáez, A.J. (Eds.), Advances in biomembranes and lipid self-assembly, Chapter 5. Academic Press, United States.10.1016/bs.abl.2021.11.005Search in Google Scholar
Haladu, S.A., Umoren, S.A., Ali, S.A., Solomon, M.M. and Mohammed, A.-R.I. (2019). Synthesis, characterization and electrochemical evaluation of anticorrosion property of a tetrapolymer for carbon steel in strong acid media. Chin. J. Chem. Eng. 27: 965–978, https://doi.org/10.1016/j.cjche.2018.07.015.Search in Google Scholar
He, X., Jiang, Y., Li, C., Wang, W., Hou, B., and Wu, L. (2014). Inhibition properties and adsorption behavior of imidazole and 2-phenyl-2-imidazoline on AA5052 in 1.0 M HCl solution. Corrosion Sci. 83: 124–136, https://doi.org/10.1016/j.corsci.2014.02.004.Search in Google Scholar
Hooshmand Zaferani, S., Sharifi, M., Zaarei, D., and Shishesaz, M.R. (2013). Application of eco-friendly products as corrosion inhibitors for metals in acid pickling processes – a review. J. Environ. Chem. Eng. 1: 652–657, https://doi.org/10.1016/j.jece.2013.09.019.Search in Google Scholar
Hou, Y., Zhu, L., He, K., Yang, Z., Ma, S., and Lei, J. (2022). Synthesis of three imidazole derivatives and corrosion inhibition performance for copper. J. Mol. Liq. 348: 118432, https://doi.org/10.1016/j.molliq.2021.118432.Search in Google Scholar
Huang, J., Li, Z., Liaw, B.Y., and Zhang, J. (2016). Graphical analysis of electrochemical impedance spectroscopy data in Bode and Nyquist representations. J. Power Sources 309: 82–98, https://doi.org/10.1016/j.jpowsour.2016.01.073.Search in Google Scholar
Jaal, R.A., Ismail, M.C., and Ariwahjoedi, B. (2014). A review of CO2 corrosion inhibition by imidazoline-based inhibitor. In: MATEC Web of conferences. EDP Sciences, France, 05012.10.1051/matecconf/20141305012Search in Google Scholar
Jevremović, I., Singer, M., Nešić, S., and Mišković-Stanković, V. (2013). Inhibition properties of self-assembled corrosion inhibitor talloil diethylenetriamine imidazoline for mild steel corrosion in chloride solution saturated with carbon dioxide. Corrosion Sci. 77: 265–272, https://doi.org/10.1016/j.corsci.2013.08.012.Search in Google Scholar
Ji Ram, V., Sethi, A., Nath, M., and Pratap, R. (2019). Five-membered heterocycles. In: The chemistry of heterocycles, Chapter 5. Elsevier, United States.10.1016/B978-0-08-101033-4.00002-4Search in Google Scholar
Kong, X., FanWeiyu, L., Ming, Q., ChengduoLuo, H., and Yao, Y. (2016). Study on the synthesis and corrosion inhibition performance of Mannich-modified imidazoline. Kemija u Industriji 65: 353–358, https://doi.org/10.15255/kui.2016.014.Search in Google Scholar
Kousar, K., Walczak, M.S., Ljungdahl, T., Wetzel, A., Oskarsson, H., Restuccia, P., Ahmad, E.A., Harrison, N.M., and Lindsay, R. (2021). Corrosion inhibition of carbon steel in hydrochloric acid: elucidating the performance of an imidazoline-based surfactant. Corrosion Sci. 180: 109195, https://doi.org/10.1016/j.corsci.2020.109195.Search in Google Scholar
Kousar, K., Ljungdahl, T., Wetzel, A., Dowhyj, M., Oskarsson, H., Walton, A.S., Walczak, M.S., and Lindsay, R. (2020). An exemplar imidazoline surfactant for corrosion inhibitor studies: synthesis, characterization, and physicochemical properties. J. Surfactants Deterg. 23: 225–234, https://doi.org/10.1002/jsde.12363.Search in Google Scholar
Law, D.W., Millard, S.G., and Bungey, J.H. (2000). Linear polarisation resistance measurements using a potentiostatically controlled guard ring. NDT E Int. 33: 15–21, https://doi.org/10.1016/s0963-8695(99)00015-8.Search in Google Scholar
Levinson, M.I. (1999). Rinse-added fabric softener technology at the close of the twentieth century. J. Surfactants Deterg. 2: 223–235, https://doi.org/10.1007/s11743-999-0077-4.Search in Google Scholar
Li, Y.Z., Xu, N., Guo, X.P., and Zhang, G.A. (2017). Inhibition effect of imidazoline inhibitor on the crevice corrosion of N80 carbon steel in the CO2-saturated NaCl solution containing acetic acid. Corrosion Sci. 126: 127–141, https://doi.org/10.1016/j.corsci.2017.06.021.Search in Google Scholar
Li, Z., Xu, X., Li, Y. and Liu, Z. (2021). Effect of imidazoline inhibitor on stress corrosion cracking of P110 steel in simulated annulus environments of CO2 injection well. J. Electroanal. Chem. 886: 115105, https://doi.org/10.1016/j.jelechem.2021.115105.Search in Google Scholar
Liu, H. and Du, D.M. (2009). Recent advances in the synthesis of 2-imidazolines and their applications in homogeneous catalysis. Adv. Synth. Catal. 351: 489–519, https://doi.org/10.1002/adsc.200800797.Search in Google Scholar
Martin, J.A. and Valone, F.W. (1985). The existence of imidazoline corrosion inhibitors. Corrosion 41: 5, https://doi.org/10.5006/1.3582003.Search in Google Scholar
Martínez-Palou, R., Rivera, J., Zepeda, L.G., Rodríguez, A.N., Hernández, M.A., Marín-Cruz, J., and Estrada, A. (2004). Evaluation of corrosion inhibitors synthesized from fatty acids and fatty alcohols isolated from sugar cane wax. Corrosion 60: 465–470, https://doi.org/10.5006/1.3299242.Search in Google Scholar
Martínez-Palou, R., de Paz, G., Marín-Cruz, J. and Zepeda, L.G. (2003). Synthesis of long chain 2-alkyl-1-(2-hydroxyethyl)-2-imidazolines under microwave in solvent-free conditions. Synlett 2003: 1847–1849, https://doi.org/10.1055/s-2003-41410.Search in Google Scholar
McMahon, A.J. (1991). The mechanism of action of an oleic imidazoline based corrosion inhibitor for oilfield use. Colloid. Surface. 59: 187–208, https://doi.org/10.1016/0166-6622(91)80247-l.Search in Google Scholar
Mehedi, M.S.A. and Tepe, J.J. (2020). Recent advances in the synthesis of imidazolines (2009–2020). Adv. Synth. Catal. 362: 4189–4225, https://doi.org/10.1002/adsc.202000709.Search in Google Scholar
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- and Tribo-Corrosion 3: 22, https://doi.org/10.1007/s40735-017-0080-5.Search in Google Scholar
Mishra, A., Aslam, J., Verma, C., Quraishi, M.A., and Ebenso, E.E. (2020). Imidazoles as highly effective heterocyclic corrosion inhibitors for metals and alloys in aqueous electrolytes: a review. J. Taiwan Inst. Chem. Eng. 114: 341–358, https://doi.org/10.1016/j.jtice.2020.08.034.Search in Google Scholar
Monticelli, C. (2018). Corrosion inhibitors. In: Wandelt, K. (Ed.), Encyclopedia of interfacial chemistry. Oxford: Elsevier.10.1016/B978-0-12-409547-2.13443-2Search in Google Scholar
Moradighadi, N., Lewis, S., Olivo, J.D., Young, D., Brown, B., and Nešić, S. (2021). Determining critical micelle concentration of organic corrosion inhibitors and its effectiveness in corrosion mitigation. Corrosion 77: 266–275, https://doi.org/10.5006/3679.Search in Google Scholar
Morales-Gil, P., Walczak, M.S., Camargo, C., Cottis, R., Romero, J.M., and Lindsay, R. (2015). Corrosion inhibition of carbon-steel with 2-mercaptobenzimidazole in hydrochloric acid. Corrosion Sci. 101: 47–55, https://doi.org/10.1016/j.corsci.2015.08.032.Search in Google Scholar
Mu, M., Chen, Y., Dong, Y., Aijun, Y., and Liao, Q. (2017). Synergistic inhibition effect of imidazoline derivative and potassium iodide on carbon steel corrosion in amidosulfuric acid solution. Corrosion Rev. 35: 463–471, https://doi.org/10.1515/corrrev-2017-0035.Search in Google Scholar
Muktiarti, N., Ditama, I., and Soegijono, B. (2020). Characterization of imidazoline derivates synthesized from soybean oil fatty acids as corrosion inhibitors on mild steel. AIP Conf. Proc. 2242: 020023.10.1063/5.0007980Search in Google Scholar
Munis, A., Zhao, T., Zheng, M., Rehman, A.U. and Wang, F. (2020). A newly synthesized green corrosion inhibitor imidazoline derivative for carbon steel in 7.5% NH4Cl solution. Sustain. Chem. Pharm. 16: 100258, https://doi.org/10.1016/j.scp.2020.100258.Search in Google Scholar
Nkomo, D. and Masia, N. (2021). An insight on corrosion resistance ability of biocompatible dental implants through electrochemical impedance spectroscopy. IntechOpen, United Kingdom.10.5772/intechopen.100330Search in Google Scholar
Obike, A., Okafor, P., Uwakwe, K., Jiang, X., and Qu, D. (2018). The inhibition of CO2 corrosion of L360 mild steel in 3.5% NaCl solution by imidazoline derivatives. Int. J. Corrosion Scale Inhib. 7: 318–330.10.17675/2305-6894-2018-7-3-3Search in Google Scholar
Ouakki, M., Galai, M. and Cherkaoui, M. (2022). Imidazole derivatives as efficient and potential class of corrosion inhibitors for metals and alloys in aqueous electrolytes: a review. J. Mol. Liq. 345: 117815, https://doi.org/10.1016/j.molliq.2021.117815.Search in Google Scholar
Ouakki, M., Galai, M., Rbaa, M., Abousalem, A.S., Lakhrissi, B., Rifi, E.H., and Cherkaoui, M. (2019). Quantum chemical and experimental evaluation of the inhibitory action of two imidazole derivatives on mild steel corrosion in sulphuric acid medium. Heliyon 5: e02759, https://doi.org/10.1016/j.heliyon.2019.e02759.Search in Google Scholar PubMed PubMed Central
Pan, C., Mao, J., and Jin, W. (2020). Effect of imidazoline inhibitor on the rehabilitation of reinforced concrete with electromigration method. Materials 13: 398, https://doi.org/10.3390/ma13020398.Search in Google Scholar PubMed PubMed Central
Pavithra, M.K., Venkatesha, T.V., Vathsala, K., and Nayana, K.O. (2010). Synergistic effect of halide ions on improving corrosion inhibition behaviour of benzisothiozole-3-piperizine hydrochloride on mild steel in 0.5M H2SO4 medium. Corrosion Sci. 52: 3811–3819, https://doi.org/10.1016/j.corsci.2010.07.034.Search in Google Scholar
Pearson, P. and Cousins, A. (2016). Assessment of corrosion in amine-based post-combustion capture of carbon dioxide systems. In: Feron, P.H.M. (Ed.). Absorption-based post-combustion capture of carbon dioxide. Woodhead Publishing, United States, p. 18.10.1016/B978-0-08-100514-9.00018-4Search in Google Scholar
Popova, A., Christov, M., and Vasilev, A. (2007). Inhibitive properties of quaternary ammonium bromides of N-containing heterocycles on acid mild steel corrosion. Part II: EIS results. Corrosion Sci. 49: 3290–3302, https://doi.org/10.1016/j.corsci.2007.03.012.Search in Google Scholar
Porcayo-Calderon, J., De La Escalera, L.M.M., Canto, J., and Casales-Diaz, M. (2015). Imidazoline derivatives based on coffee oil as CO2 corrosion inhibitor. Int. J. Electrochem. Sci. 10: 3160–3176.Search in Google Scholar
Poursaee, A. (2014). Corrosion sensing for assessing and monitoring civil infrastructures. In: Wang, M.L., Lynch, J.P., and Sohn, H. (Eds.), Sensor technologies for civil infrastructures. Woodhead Publishing, United States, p. 13.10.1533/9780857099136.357Search in Google Scholar
Qian, S. and Cheng, Y.F. (2019). Synergism of imidazoline and sodium dodecylbenzenesulphonate inhibitors on corrosion inhibition of X52 carbon steel in CO2-saturated chloride solutions. J. Mol. Liq. 294: 111674, https://doi.org/10.1016/j.molliq.2019.111674.Search in Google Scholar
Rahayu, D.U.C., Krisnandi, Y.K., Susanto, B.H., Abdullah, I., Nurani, D.A., Saragi, I.R., Yuniastuti, A., Mujahiduzzakka, M., Cahyani, S., Fitriani, S., et al.. (2021). Synthesis of oleic-imidazoline and investigation on its inhibition efficiency for the corrosion of low carbon steel in chloride environments. Int. J. Corrosion Scale Inhib. 10: 1282–1293.10.17675/2305-6894-2021-10-3-25Search in Google Scholar
Rodríguez-Valdez, L.M., Villamisar, W., Casales, M., González-Rodriguez, J.G., Martínez-Villafañe, A., Martinez, L., and Glossman-Mitnik, D. (2006). Computational simulations of the molecular structure and corrosion properties of amidoethyl, aminoethyl and hydroxyethyl imidazolines inhibitors. Corrosion Sci. 48: 4053–4064, https://doi.org/10.1016/j.corsci.2006.05.036.Search in Google Scholar
Shamsa, A., Barker, R., Hua, Y., Barmatov, E., Hughes, T.L., and Neville, A. (2020). Performance evaluation of an imidazoline corrosion inhibitor in a CO2-saturated environment with emphasis on localised corrosion. Corrosion Sci. 176: 108916, https://doi.org/10.1016/j.corsci.2020.108916.Search in Google Scholar
Shamsa, A., Barker, R., Hua, Y., Barmatov, E., Hughes, T.L., and Neville, A. (2021). Impact of corrosion products on performance of imidazoline corrosion inhibitor on X65 carbon steel in CO2 environments. Corrosion Sci. 185: 109423, https://doi.org/10.1016/j.corsci.2021.109423.Search in Google Scholar
Shamsa, A., Barmatov, E., Hughes, T.L., Hua, Y., Neville, A., and Barker, R. (2022). Hydrolysis of imidazoline based corrosion inhibitor and effects on inhibition performance of X65 steel in CO2 saturated brine. J. Petrol. Sci. Eng. 208: 109235, https://doi.org/10.1016/j.petrol.2021.109235.Search in Google Scholar
Sharma, M.K. and Ghuge, R.B. (2018). Chemical and biological profiles of vicinal diaryl-substituted thiophenes, imidazolines, selendiazoles, and isoselenazoles. In: Vicinal diaryl substituted heterocycles, Chapter 10. Elsevier, United States, pp. 305–326.10.1016/B978-0-08-102237-5.00010-9Search in Google Scholar
Solomon, M.M., Umoren, S.A., Quraishi, M.A. and Mazumder, M.A.J. (2019a). Corrosion inhibition of N80 steel in simulated acidizing environment by N-(2-(2-pentadecyl-4, 5-dihydro-1H-imidazol-1-YL) ethyl) palmitamide. J. Mol. Liq. 273: 476–487, https://doi.org/10.1016/j.molliq.2018.10.032.Search in Google Scholar
Solomon, M.M., Umoren, S.A., Quraishi, M.A., and Salman, M. (2019b). Myristic acid based imidazoline derivative as effective corrosion inhibitor for steel in 15% HCl medium. J. Colloid Interface Sci. 551: 47–60, https://doi.org/10.1016/j.jcis.2019.05.004.Search in Google Scholar PubMed
Solomon, M.M., Umoren, S.A., Quraishi, M.A., Tripathy, D.B. and Abai, E.J. (2020). Effect of akyl chain length, flow, and temperature on the corrosion inhibition of carbon steel in a simulated acidizing environment by an imidazoline-based inhibitor. J. Petrol. Sci. Eng. 187: 106801, https://doi.org/10.1016/j.petrol.2019.106801.Search in Google Scholar
Stupnisek, L.E., Kasunic, D., and Vorkapic, F.J. (1995). Imidazole derivatives as corrosion inhibitors for zinc in hydrochloric acid. Corrosion 51: 767–772, https://doi.org/10.5006/1.3293554.Search in Google Scholar
Tan, Y.J., Bailey, S., and Kinsella, B. (1996). An investigation of the formation and destruction of corrosion inhibitor films using electrochemical impedance spectroscopy (EIS). Corrosion Sci. 38: 1545–1561, https://doi.org/10.1016/0010-938x(96)00047-9.Search in Google Scholar
Telegdi, J., Shaban, A., and Vastag, G. (2018). Biocorrosion—steel. In: Wandelt, K. (Ed.), Encyclopedia of interfacial chemistry. Elsevier, Oxford.10.1016/B978-0-12-409547-2.13591-7Search in Google Scholar
Tripathy, D.B. and Mishra, A. (2017). Convenient synthesis, characterization and surface active properties of novel cationic gemini surfactants with carbonate linkage based on C12C18 sat./unsat. fatty acids. J. Appl. Res. Technol. 15: 93–101, https://doi.org/10.1016/j.jart.2016.12.004.Search in Google Scholar
Tyagi, R., Tyagi, V.K., and Pandey, S.K. (2007). Imidazoline and its derivatives: an overview. J. Oleo Sci. 56: 211–222, https://doi.org/10.5650/jos.56.211.Search in Google Scholar PubMed
Umoren, S.A. (2016). Polypropylene glycol: a novel corrosion inhibitor for ×60 pipeline steel in 15% HCl solution. J. Mol. Liq. 219: 946–958, https://doi.org/10.1016/j.molliq.2016.03.077.Search in Google Scholar
Usman, B.J. and Ali, S.A. (2018). Carbon dioxide corrosion inhibitors: a review. Arabian J. Sci. Eng. 43: 1–22, https://doi.org/10.1007/s13369-017-2949-5.Search in Google Scholar
Usyatinsky, A.Y. and Khmelnitsky, Y.L. (2000). Microwave-assisted synthesis of substituted imidazoles on a solid support under solvent-free conditions. Tetrahedron Lett. 41: 5031–5034, https://doi.org/10.1016/s0040-4039(00)00771-1.Search in Google Scholar
Vedalakshmi, R., Manoharan, S.P., Song, H.-W., and Palaniswamy, N. (2009). Application of harmonic analysis in measuring the corrosion rate of rebar in concrete. Corrosion Sci. 51: 2777–2789, https://doi.org/10.1016/j.corsci.2009.07.014.Search in Google Scholar
Vinutha, M.R. and Venkatesha, T.V. (2016). Review on mechanistic action of inhibitors on steel corrosion in acidic media. Port. Electrochim. Acta 34: 157–184, https://doi.org/10.4152/pea.201603157.Search in Google Scholar
Wahyuningrum, D., Achmad, S., Syah, Y., Buchari, B., and Ariwahjoedi, B. (2008). The synthesis of imidazoline derivative compounds as corrosion inhibitor towards carbon steel in 1% NaCl Solution. ITB J. Sci. 40: 33–48, https://doi.org/10.5614/itbj.sci.2008.40.1.4.Search in Google Scholar
Wang, B., Du, M., Zhang, J., and Gao, C.J. (2011). Electrochemical and surface analysis studies on corrosion inhibition of Q235 steel by imidazoline derivative against CO2 corrosion. Corrosion Sci. 53: 353–361, https://doi.org/10.1016/j.corsci.2010.09.042.Search in Google Scholar
Wang, B., Du, M., Zhang, J., Li, C., Liu, J., Liu, H., Li, R., and Li, Z. (2019). Corrosion inhibition of mild steel by the hydrolysate of an imidazoline-based inhibitor in CO2-saturated solution. RSC Adv. 9: 36546–36557, https://doi.org/10.1039/c9ra05322k.Search in Google Scholar PubMed PubMed Central
Wang, P., Xiong, L., He, Z., Xu, X., Hu, J., Chen, Q., Zhang, R., Pu, J., and Guo, L. (2022). Synergistic effect of imidazoline derivative and benzimidazole as corrosion inhibitors for Q235 steel: an electrochemical, XPS, FT-IR and MD study. Arabian J. Sci. Eng. 47: 7123–7134, https://doi.org/10.1007/s13369-021-06540-4.Search in Google Scholar
Wolkenberg, S., Wisnoski, D., Leister, W., Wang, Y., Zhao, Z., and Lindsley, C. (2004). Efficient synthesis of imidazoles from aldehydes and 1,2-diketones using microwave irradiation. Org. Lett. 6: 1453–1456, https://doi.org/10.1021/ol049682b.Search in Google Scholar PubMed
Xhanari, K., Wang, Y., Yang, Z., and Finšgar, M. (2021). A review of recent advances in the inhibition of sweet corrosion. Chem. Rec. 21: 1845–1875.10.1002/tcr.202100072Search in Google Scholar PubMed
Xiong, L., Wang, P., He, Z., Chen, Q., Pu, J., and Zhang, R. (2021). Corrosion behaviors of Q235 carbon steel under imidazoline derivatives as corrosion inhibitors: experimental and computational investigations. Arab. J. Chem. 14: 102952, https://doi.org/10.1016/j.arabjc.2020.102952.Search in Google Scholar
Yoo, S.-H., Kim, Y.-W., Chung, K., Baik, S.-Y., and Kim, J.-S. (2012). Synthesis and corrosion inhibition behavior of imidazoline derivatives based on vegetable oil. Corrosion Sci. 59: 42–54, https://doi.org/10.1016/j.corsci.2012.02.011.Search in Google Scholar
Zeng, D., Dong, B., Shi, S., Pan, J., Yu, H., Li, J., Ding, Y., and Cai, L. (2018). Effects of temperature on corrosion of N80 and 3Cr steels in the simulated CO2 auxiliary steam drive environment. Arabian J. Sci. Eng. 43: 3845–3854, https://doi.org/10.1007/s13369-018-3081-x.Search in Google Scholar
Zhang, G., Chen, C., Lu, M., Chai, C., and Wu, Y. (2007). Evaluation of inhibition efficiency of an imidazoline derivative in CO2-containing aqueous solution. Mater. Chem. Phys. 105: 331–340, https://doi.org/10.1016/j.matchemphys.2007.04.076.Search in Google Scholar
Zhang, H., Gao, K., Yan, L., and Pang, X. (2017). Inhibition of the corrosion of X70 and Q235 steel in CO2-saturated brine by imidazoline-based inhibitor. J. Electroanal. Chem. 791: 83–94, https://doi.org/10.1016/j.jelechem.2017.02.046.Search in Google Scholar
Zhang, H., Pang, X. and Gao, K. (2018). Localized CO2 corrosion of carbon steel with different microstructures in brine solutions with an imidazoline-based inhibitor. Appl. Surf. Sci. 442: 446–460, https://doi.org/10.1016/j.apsusc.2018.02.115.Search in Google Scholar
Zhang, H., Pang, X., Zhou, M., Liu, C., Wei, L., and Gao, K. (2015a). The behavior of pre-corrosion effect on the performance of imidazoline-based inhibitor in 3 wt.% NaCl solution saturated with CO2. Appl. Surf. Sci. 356: 63–72, https://doi.org/10.1016/j.apsusc.2015.08.003.Search in Google Scholar
Zhang, J., Gong, X.‐L., Song, W.‐W., Jiang, B., and Du, M. (2012). Synthesis of imidazoline‐based dissymmetric bis‐quaternary ammonium gemini surfactant and its inhibition mechanism on Q235 steel in hydrochloric acid medium. Mater. Corros. 63: 636–645.10.1002/maco.201006051Search in Google Scholar
Zhang, J., Niu, L., Zhu, F., Li, C., and Du, M. (2013). Theoretical and experimental studies for corrosion inhibition performance of Q235 steel by imidazoline inhibitors against CO2 corrosion. J. Surfactants Deterg. 16: 947–956, https://doi.org/10.1007/s11743-013-1515-8.Search in Google Scholar
Zhang, K., Xu, B., Yang, W., Yin, X., Liu, Y., and Chen, Y. (2015b). Halogen-substituted imidazoline derivatives as corrosion inhibitors for mild steel in hydrochloric acid solution. Corrosion Sci. 90: 284–295, https://doi.org/10.1016/j.corsci.2014.10.032.Search in Google Scholar
Zhang, K., Yang, W., Xu, B., Liu, Y., Yin, X., and Chen, Y. (2015c). Corrosion inhibition of mild steel by bromide-substituted imidazoline in hydrochloric acid. J. Taiwan Inst. Chem. Eng. 57: 167–174, https://doi.org/10.1016/j.jtice.2015.05.021.Search in Google Scholar
Zhang, L., He, Y., Zhou, Y., Yang, R., Yang, Q., Qing, D. and Niu, Q. (2015d). A novel imidazoline derivative as corrosion inhibitor for P110 carbon steel in hydrochloric acid environment. Petroleum 1: 237–243, https://doi.org/10.1016/j.petlm.2015.10.007.Search in Google Scholar
Zhang, X., Wang, F., He, Y., and Du, Y. (2001). Study of the inhibition mechanism of imidazoline amide on CO2 corrosion of Armco iron. Corrosion Sci. 43: 1417–1431, https://doi.org/10.1016/s0010-938x(00)00160-8.Search in Google Scholar
Zhao, J. and Chen, G. (2012). The synergistic inhibition effect of oleic-based imidazoline and sodium benzoate on mild steel corrosion in a CO2-saturated brine solution. Electrochim. Acta 69: 247–255, https://doi.org/10.1016/j.electacta.2012.02.101.Search in Google Scholar
Zhao, P., Ren, R., Zhou, H., Ouyang, J., Li, Z., and Sun, D. (2021). Preparation and properties of imidazoline surfactant as additive for warm mix asphalt. Construct. Build. Mater. 273: 121692, https://doi.org/10.1016/j.conbuildmat.2020.121692.Search in Google Scholar
Zhao, B. and Zou, L.K. (2013). Corrosion inhibition of chloroacetic-acid modified imidazoline for Q235 steel in H2SO4 solution. Adv. Mater. Res. 710: 41–44, https://doi.org/10.4028/www.scientific.net/AMR.710.41.Search in Google Scholar
Zheng, Z., Hu, J., Eliaz, N., Zhou, L., Yuan, X., and Zhong, X. (2022). Mercaptopropionic acid-modified oleic imidazoline as a highly efficient corrosion inhibitor for carbon steel in CO2-saturated formation water. Corrosion Sci. 194: 109930, https://doi.org/10.1016/j.corsci.2021.109930.Search in Google Scholar
Zhong, H., Shi, Z., Jiang, G., and Yuan, Z. (2020). Synergistic inhibitory effects of free nitrous acid and imidazoline derivative on metal corrosion in a simulated water injection system. Water Res. 184: 116122, https://doi.org/10.1016/j.watres.2020.116122.Search in Google Scholar PubMed
Zuo, Y., Yang, L., Tan, Y., Wang, Y. and Zhao, J. (2017). The effects of thioureido imidazoline and NaNO2 on passivation and pitting corrosion of X70 steel in acidic NaCl solution. Corrosion Sci. 120: 99–106, https://doi.org/10.1016/j.corsci.2016.12.015.Search in Google Scholar
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