Synthesis, structural characterization and corrosion inhibition performance of propargyl- and allyl-containing aryloxy alcohol derivatives in H₂S medium
Original scientific paper
DOI:
https://doi.org/10.5599/jese.3611Keywords:
aryloxy alcohol derivatives, corrosion inhibitor, electrochemical impedance spectroscopy, corrosion protection, hydrogen sulfideAbstract
Two novel aryloxy alcohol derivatives, one containing a terminal C≡C bond (RH-1) and an allyl ether containing a C=C bond (RH-2), were synthesized and evaluated as corrosion inhibitors for St-3 carbon steel in a hydrogen sulphide (H₂S)-containing medium. Their molecular structures were characterized by Fourier-transform infrared (FTIR) spectroscopy and nuclear magnetic resonance - ¹H NMR and ¹³C NMR. Corrosion inhibition performance was investigated using gravimetric measurements, electrochemical impedance spectroscopy (EIS), potentiodynamic polarization, surface characterization and density functional theory (DFT) calculations. Gravimetric experiments were conducted over the temperature range of 25 to 50 °C using inhibitor concentrations of 10 to 30 ppm. Both compounds effectively reduced the corrosion rate, with inhibition efficiency increasing with inhibitor concentration. At 25 °C and 30 ppm, EIS showed maximum inhibition efficiencies of 97.0 % for RH-1 and 94.0 % for RH-2. EIS measurements showed a substantial increase in charge-transfer resistance and a decrease in double-layer capacitance, consistent with progressive inhibitor adsorption and formation of a protective interfacial layer. Surface analyses further supported the formation of protective inhibitor-containing films on the steel surface. DFT calculations indicated greater electron-donating ability and a stronger adsorption tendency for RH-1, consistent with its superior experimental inhibition performance. The higher efficiency of RH-1 was associated with its propargyl (C≡C) functionality, which promotes stronger interaction with the steel surface than the allyl (C=C) functionality of RH-2. The combined experimental and theoretical results demonstrate that these aryloxy alcohol derivatives provide effective corrosion inhibition of carbon steel in H₂S-containing environments.
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[1] M. B. Kermani, A. Morshed, Carbon dioxide corrosion in oil and gas production: A compendium, Corrosion 59 (2003) 659-683. https://doi.org/10.5006/1.3277596 DOI: https://doi.org/10.5006/1.3277596
[2] S. Nešić, Key issues related to modelling of internal corrosion of oil and gas pipelines: A review, Corrosion Science 49 (2007) 4308-4338. https://doi.org/10.1016/j.corsci.2007.06.006 DOI: https://doi.org/10.1016/j.corsci.2007.06.006
[3] U. Bharatiya, P. Gal, A. Agrawal, M. Shah, A. Sircar, Effect of corrosion on crude oil and natural gas pipeline with emphasis on prevention by ecofriendly corrosion inhibitors: A comprehensive review, Journal of Bio- and Tribo-Corrosion 5 (2019) 35. https://doi.org/10.1007/s40735-019-0225-9 DOI: https://doi.org/10.1007/s40735-019-0225-9
[4] P. B. Raja, M. Ismail, S. Ghoreishiamiri, J. Mirza, M. C. Ismail, S. Kakooei, A. A. Rahim, Reviews on corrosion inhibitors: A short view, Chemical Engineering Communications 203 (2016) 1145-1156. https://doi.org/10.1080/00986445.2016.1172485 DOI: https://doi.org/10.1080/00986445.2016.1172485
[5] S. Lynch, Discussion of some recent literature on hydrogen-embrittlement mechanisms: Addressing common misunderstandings, Corrosion Reviews 37 (2019) 377-395. https://doi.org/10.1515/corrrev-2019-0017 DOI: https://doi.org/10.1515/corrrev-2019-0017
[6] S. J. Kim, Effect of the elastic tensile load on the electrochemical corrosion behavior and diffusible hydrogen content of ferritic steel in acidic environment, International Journal of Hydrogen Energy 42 (2017) 19367-19375. https://doi.org/10.1016/j.ijhydene.2017.05.210 DOI: https://doi.org/10.1016/j.ijhydene.2017.05.210
[7] X. Li, X. Ma, J. Zhang, E. Akiyama, Y. Wang, X. Song, Review of hydrogen embrittlement in metals: Hydrogen diffusion, hydrogen characterization, hydrogen embrittlement mechanism and prevention, Acta Metallurgica Sinica (English Letters) 33 (2020) 759-773. https://doi.org/10.1007/s40195-020-01039-7 DOI: https://doi.org/10.1007/s40195-020-01039-7
[8] J. S. Park, J. W. Lee, J. K. Hwang, S. J. Kim, Effects of alloying elements (C, Mo) on hydrogen assisted cracking behaviors of A516-65 steels in sour environments, Materials 13 (2020) 4188. https://doi.org/10.3390/ma13184188 DOI: https://doi.org/10.3390/ma13184188
[9] E. F. Sultanov, A. N. Gurbanov, I. Z. Sardarova, Investigation of the bactericidal-inhibitory effect of sulfonate and benzalkonium chloride-based substance against corrosion caused by hydrogen sulfide (H₂S), carbon dioxide (CO₂), and microorganisms, Nafta-Gaz 82 (2026) 52-59. https://doi.org/10.18668/NG.2026.01.05 DOI: https://doi.org/10.18668/NG.2026.01.05
[10] E. K. Iskandarov, I. N. Aliyev, A. Yergali, Laboratory and field testing of a pyrocondensate-based and clay-modified composition for apparent hydrate-onset control and erosion-wear mitiga¬tion in natural gas pipelines, Energies 19 (2026) 2755. https://doi.org/10.3390/en19122755 DOI: https://doi.org/10.3390/en19122755
[11] L. Bekbayeva, E.-S. Negim, R. Zhanibekov, R. Sharipov, G. Maldybayev, D. Puzikova, N. Kenzin, A. A. B. Maridan, Epoxy coatings for anticorrosion applications, Complex Use of Mineral Resources 337 (2026) 35-46. https://doi.org/10.31643/2026/6445.15 DOI: https://doi.org/10.31643/2026/6445.15
[12] G. Palanisamy, Corrosion inhibitors, in Corrosion Inhibitors, A. Singh Ed., IntechOpen, 2019, pp. 2-26. https://doi.org/10.5772/intechopen.80542 DOI: https://doi.org/10.5772/intechopen.80542
[13] M. A. Quraishi, D. S. Chauhan, F. A. Ansari, Development of environmentally benign corrosion inhibitors for organic acid environments for oil-gas industry, Journal of Molecular Liquids 329 (2021) 115514. https://doi.org/10.1016/j.molliq.2021.115514 DOI: https://doi.org/10.1016/j.molliq.2021.115514
[14] R. M. Palou, N. V. Likhanova, Applications of ionic liquids as corrosion inhibitors in the oil indus¬try, in: Applications of Ionic Liquids in the Oil Industry: Towards a Sustainable Industry, Bentham Science Publishers, 2023, pp. 94-121. https://doi.org/10.2174/9789815079579123010008 DOI: https://doi.org/10.2174/9789815079579123010008
[15] A. Thakur, S. Kaya, A. S. Abousalem, S. Sharma, R. Ganjoo, H. Assad, A. Kumar, Computa-tional and experimental studies on the corrosion inhibition performance of an aerial extract of Cnicus benedictus weed on the acidic corrosion of mild steel, Process Safety and Environmental Protection 161 (2022) 801-818. https://doi.org/10.1016/j.psep.2022.03.082 DOI: https://doi.org/10.1016/j.psep.2022.03.082
[16] S. Boukerche, H. Ferkous, A. Delimi, A. Sedik, A. Djedouani, K. O. Rachedi, H. Bouchoukh, M. Berredjem, M. Zahzouh, A. Himour, S. Bellucci, M. Alam, Y. Benguerba, Anti-corrosion perfor¬mance of dehydroacetic acid thiosemicarbazone on XC38 carbon steel in an acidic medium, Arabian Journal of Chemistry 16 (2023) 105061. https://doi.org/10.1016/j.arabjc.2023.105061 DOI: https://doi.org/10.1016/j.arabjc.2023.105061
[17] Z. El Adnani, M. Mcharfi, M. Sfaira, M. Benzakour, A. T. Benjelloun, M. Ebn Touhami, DFT theoretical study of 7-R-3-methylquinoxalin-2(1H)-thiones as corrosion inhibitors in hydro-chloric acid, Corrosion Science 68 (2013) 223-230. https://doi.org/10.1016/j.corsci.2012.11.020 DOI: https://doi.org/10.1016/j.corsci.2012.11.020
[18] Q. Wang, X. Zhou, R. Wang, R. Aslam, X. Sun, Y. Sun, Z. Yan, X. Li, Synergistic effect of KI on corrosion inhibition of carbon steel by Styphnolobium japonicum (L.) Schott in H₂SO₄ solution, Journal of Molecular Structure 1309 (2024) 138251. https://doi.org/10.1016/j.molstruc.2024.138251 DOI: https://doi.org/10.1016/j.molstruc.2024.138251
[19] G. Wei, S. Deng, Y. Qiang, Y. Zhang, X. Li, Halogenated pyrimidines as promising inhibitors for cold-rolled steel in HCl and H₂SO₄ media: Experiments and theoretical calculations, Corrosion Science 246 (2025) 112724. https://doi.org/10.1016/j.corsci.2025.112724 DOI: https://doi.org/10.1016/j.corsci.2025.112724
[20] H. M. Abd El-Lateef, M. M. Khalaf, M. Gouda, K. Shalabi, F. El-Taib Heakal, A. S. M. Al-Janabi, S. Shaaban, Novel water-soluble organoselenocyanates and symmetrical diselenides tethered to N-succinanilate and N-maleanilate as corrosion inhibitors for reinforced steel in simulated concrete pore solution, Construction and Building Materials 366 (2023) 130135. https://doi.org/10.1016/j.conbuildmat.2022.130135 DOI: https://doi.org/10.1016/j.conbuildmat.2022.130135
[21] S. Shaaban, K. Shalabi, T. A. Yousef, M. Abou-Krisha, A. A. Alanazi, H. A. Althikrallah, M. Alaasar, A. M. Abu-Dief, A. S. M. Al-Janabi, Promising organoselenium corrosion inhibitors for C1018 steel in hydrochloric acid environments, Journal of the Taiwan Institute of Chemical Engineers 165 (2024) 105766. https://doi.org/10.1016/j.jtice.2024.105766 DOI: https://doi.org/10.1016/j.jtice.2024.105766
[22] K. R. Ansari, M. A. Quraishi, A. Singh, Schiff’s bases of pyridyl-substituted triazoles as new and effective corrosion inhibitors for mild steel in hydrochloric acid solution, Corrosion Science 79 (2014) 5-15. https://doi.org/10.1016/j.corsci.2013.10.009 DOI: https://doi.org/10.1016/j.corsci.2013.10.009
[23] M. A. Migahed, A. Elgendy, M. M. El-Rabiei, H. Nady, E. G. Zaki, Novel gemini cationic surfactants as corrosion inhibitors for X-65 steel in oilfield-produced water under sweet conditions: Combined experimental and computational investigations, Journal of Molecular Structure 1159 (2018) 10-22. https://doi.org/10.1016/j.molstruc.2018.01.033 DOI: https://doi.org/10.1016/j.molstruc.2018.01.033
[24] K. M. Abd El-Khalek, K. Shalabi, M. A. Ismail, A. E. S. Fouda, 5-Arylidene-1,3-dialkylbarbituric acid derivatives as efficient corrosion inhibitors for carbon steel in molar hydrochloric acid solution, RSC Advances 12 (2022) 10443-10459. https://doi.org/10.1039/D2RA00696K DOI: https://doi.org/10.1039/D2RA00696K
[25] A. A. Olajire, Corrosion inhibition of offshore oil and gas production facilities using organic compound inhibitors: A review, Journal of Molecular Liquids 248 (2017) 775-808. https://doi.org/10.1016/j.molliq.2017.10.097 DOI: https://doi.org/10.1016/j.molliq.2017.10.097
[26] B. E. A. Rani, B. B. J. Basu, Green inhibitors for corrosion protection of metals and alloys, International Journal of Corrosion 2012 (2012) 380217. https://doi.org/10.1155/2012/380217 DOI: https://doi.org/10.1155/2012/380217
[27] C. Boulechfar, H. Ferkous, S. Djellali, M. A. Amin, S. Boufas, A. Djedouani, A. Delimi, Y. Ben Amor, K. Yadav, B. H. Jeon, Y. Benguerba, DFT/molecular-scale, MD simulation and assessment of the eco-friendly anti-corrosion performance of a novel Schiff base on XC38 carbon steel in acidic medium, Journal of Molecular Liquids 344 (2021) 117874. https://doi.org/10.1016/j.molliq.2021.117874 DOI: https://doi.org/10.1016/j.molliq.2021.117874
[28] H. M. Yang, Role of organic and eco-friendly inhibitors on the corrosion mitigation of steel in acidic environments: A state-of-the-art review, Molecules 26 (2021) 3473. https://doi.org/10.3390/molecules26113473 DOI: https://doi.org/10.3390/molecules26113473
[29] N. M. El Basiony, A. Elgendy, H. Nady, M. A. Migahed, E. G. Zaki, Adsorption characteristics and inhibition effect of two Schiff base compounds on corrosion of mild steel in 0.5 M HCl solution: Experimental, DFT studies, and Monte Carlo simulation, RSC Advances 9 (2019) 10473-10485. https://doi.org/10.1039/C9RA00397E DOI: https://doi.org/10.1039/C9RA00397E
[30] R. Oukhrib, Y. Abdellaoui, A. Berisha, H. Abou Oualid, J. Halili, K. Jusufi, M. Ait El Had, H. Bourzi, S. El Issami, F. A. Asmary, V. S. Parmar, C. Len, DFT, Monte Carlo and molecular dynamics simulations for the prediction of corrosion inhibition efficiency of novel pyrazolyl nucleosides on Cu(111) surface in acidic media, Scientific Reports 11 (2021) 3771. https://doi.org/10.1038/s41598-021-82927-5 DOI: https://doi.org/10.1038/s41598-021-82927-5
[31] P. A. Baghbadrani, A. N. Chermahini, Theoretical investigation of corrosion inhibition by 5-hydrazino tetrazole tautomers using DFT calculations and Monte Carlo simulation, Results in Chemistry 22 (2026) 103087. https://doi.org/10.1016/j.rechem.2026.103087 DOI: https://doi.org/10.1016/j.rechem.2026.103087
[32] H. M. H. Farh, M. E. A. Ben Seghier, T. Zayed, A comprehensive review of corrosion protection and control techniques for metallic pipelines, Engineering Failure Analysis 143 (2023) 106885. https://doi.org/10.1016/j.engfailanal.2022.106885 DOI: https://doi.org/10.1016/j.engfailanal.2022.106885
[33] A. A. Adamu, O. R. A. Iyun, J. D. Habila, Adsorption and thermodynamic studies of the corrosion inhibition effect of Desmodium adscendens (Swartz) extract on carbon steel in 2 M HCl, BMC Chemistry 19 (2025) 163. https://doi.org/10.1186/s13065-025-01541-y DOI: https://doi.org/10.1186/s13065-025-01541-y
[34] G. M. Talybov, S. V. Ibrahimova, Allyl and propargyl ethers of dihaloalkanols: Synthesis and study of them as antimicrobial additives, French-Ukrainian Journal of Chemistry 13 (2025) 24-30. https://doi.org/10.17721/fujcV13I2P24-30 DOI: https://doi.org/10.17721/fujcV13I2P24-30
[35] G. R. Gurbanov, A. V. Gasimzade, Enhancing demulsification efficiency and corrosion protection in oil industry: A study of novel compositions, Voprosy Khimii i Khimicheskoi Tekhnologii 2 (2024) 18-25. http://dx.doi.org/10.32434/0321-4095-2024-153-2-18-25 DOI: https://doi.org/10.32434/0321-4095-2024-153-2-18-25
[36] G. R. Gurbanov, A. V. Gasimzade, S. F. Alikishiyeva-Balamiyeva, Research of bactericide-inhibitor properties of new compositions based on gossypol resin and chloroprene, Nafta-Gaz 81 (2025) 58-66. https://doi.org/10.18668/NG.2025.01.07 DOI: https://doi.org/10.18668/NG.2025.01.05
[37] A. V. Gasimzade, Z. I. Farzalizade, Development and performance evaluation of a synergistic composite inhibitor against electrochemical and microbiologically influenced corrosion, Voprosy Khimii i Khimicheskoi Tekhnologii 165 (2026) 30-40. https://doi.org/10.32434/0321-4095-2026-165-2-30-40 DOI: https://doi.org/10.32434/0321-4095-2026-165-2-30-40
[38] G. R. Gurbanov, A. V. Gasimzade, Study of the bactericidal-inhibitor properties of new rea-gents, Rudarsko-Geološko-Naftni Zbornik 41 (2026) 15-30. https://doi.org/10.17794/rgn.2026.2.2 DOI: https://doi.org/10.17794/rgn.2026.2.2
[39] ASTM International, ASTM G31-21: Standard Guide for Laboratory Immersion Corrosion Testing of Metals, 2021. https://doi.org/10.1520/G0031-21 DOI: https://doi.org/10.1520/G0031-21
[40] Y. P. Asmara, T. Kurniawan, Corrosion prediction for corrosion rate of carbon steel in oil and gas environment, Indonesian Journal of Science and Technology 3 (2018) 64-74. https://doi.org/10.17509/ijost.v3i1.10808 DOI: https://doi.org/10.17509/ijost.v3i1.10808
[41] ASTM International, ASTM G106-89, Standard Practice for Verification of Algorithm and Equipment for Electrochemical Impedance Measurements, 2023. https://doi.org/10.1520/G0106-89R23 DOI: https://doi.org/10.1520/G0106-89R23
[42] F. Bentiss, M. Lebrini, H. Vezin, F. Chai, M. Traisnel, M. Lagrenée, Enhanced corrosion resistance of carbon steel in sulfuric acid medium by some macrocyclic polyether compounds containing a 1,3,4-thiadiazole moiety: AC impedance and computational studies, Corrosion Science 51 (2009) 2165-2173. https://doi.org/10.1016/j.corsci.2009.05.049 DOI: https://doi.org/10.1016/j.corsci.2009.05.049
[43] F. El-Hajjaji, E. Ech-chihbi, N. Rezki, F. Benhiba, M. Taleb, D. S. Chauhan, M. A. Quraishi, Electrochemical and theoretical insights on the adsorption and corrosion inhibition of novel pyridinium-derived ionic liquids for mild steel in 1 M HCl, Journal of Molecular Liquids 314 (2020) 113737. https://doi.org/10.1016/j.molliq.2020.113737 DOI: https://doi.org/10.1016/j.molliq.2020.113737
[44] K. Dahmani, M. Galai, M. Rbaa, A. Ech-Chebab, N. Errahmany, L. Guo, A. A. Al Obaid, A. Hmada, I. Warad, B. Lakhrissi, M. Ebn Touhami, M. Cherkaoui, Evaluating the efficacy of synthesized quinoline derivatives as corrosion inhibitors for mild steel in acidic environ-ments: An analysis using electrochemical, computational, and surface techniques, Journal of Molecular Structure 1295 (2024) 136514. https://doi.org/10.1016/j.molstruc.2023.136514 DOI: https://doi.org/10.1016/j.molstruc.2023.136514
[45] D. Sharma, A. Thakur, M. K. Sharma, R. Sharma, S. Kumar, A. Sihmar, H. Dahiya, G. Jha, A. Kumar, A. K. Sharma, H. Om, Effective corrosion inhibition of mild steel using novel
1,3,4-oxadiazole-pyridine hybrids: Synthesis, electrochemical, morphological, and computational insights, Environmental Research 234 (2023) 116555. https://doi.org/10.1016/j.envres.2023.116555 DOI: https://doi.org/10.1016/j.envres.2023.116555
[46] J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Jane¬sko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Ren¬dell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian 16 Revision C.01, Gaussian, Inc., Wallingford, CT, USA, 2016. https://gaussian.com/gaussian16/
[47] R. Dennington, T. Keith, J. Millam, GaussView, Version 6, Semichem Inc., Shawnee Mission, KS, USA, 2016. https://gaussian.com/wp-content/uploads/dl/gv6.pdf?utm_source=chatgpt.com
[48] G. W. Snedecor, W. G. Cochran, Statistical Methods, 8th ed., Iowa State University Press, Ames, IA, USA, 1989. ISBN: 978-0-8138-1561-9.
[49] D. C. Montgomery, Design and Analysis of Experiments, 10th ed., Wiley, Hoboken, NJ, USA, 2020 ISBN: 978-1-119-72210-6.
[50] M. G. Lagutkin, A. S. Abramov, S. V. Mikhailovskii, V. G. Sorokin, S. R. Koryukin, Yu. V. Filatov, Statistics and analysis of corrosion damage of fuel storage pipelines and vertical tanks, Chemi¬cal and Petroleum Engineering 53 (2017) 139-142. https://doi.org/10.1007/s10556-017-0310-1 DOI: https://doi.org/10.1007/s10556-017-0310-1
[51] OriginLab Corporation, OriginPro 2024, 2023. https://www.originlab.com/origin
[52] K. Al-Amin, M. Kawsar, M. T. R. B. Mamun, M. S. Hossain, Fourier transform infrared spectroscopic technique for analysis of inorganic materials, Nanoscale Advances 7 (2025) 6677-6702. https://doi.org/10.1039/D5NA00522A DOI: https://doi.org/10.1039/D5NA00522A
[53] T. Nunney, Using Deconvolution Methods to Improve the Spectral and Spatial Resolution of XPS Data, Thermo Fisher Scientific, Application Note AN0117-EN-12-2019, 2019. https://documents.thermofisher.com/TFS-Assets/MSD/Application-Notes/AN0117-XPS-deconvolution.pdf
[54] Y. Cui, C. Hao, B. Dai, H. Peng, W. Yang, X-ray photoelectron spectroscopy for alloy research: From fundamental principles to advanced applications, Metals 16 (2026) 444. https://doi.org/10.3390/met16040444 DOI: https://doi.org/10.3390/met16040444
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