Gunay Mehdıyeva MUZAKIR, Musa Baıramov RZA, Shahnaz Hosseınzadeh BAHADOR, Gulnara Hasanova MUSA

Allylphenoxypiperidinium halides as corrosion inhibitors of carbon steel and biocides

A series of 1- 4- 2-allylphenoxy butyl piperidin-1-ium halides 4a-d was synthesized and characterized via spectroscopic methods FTIR, $^{1}$H NMR . The corrosion inhibition of the synthesized halides on carbon steel in water-salt-hydrocarbon environment, saturated with H$_{2}$S, was investigated. For this purpose, a series of techniques such as gravimetric measurement, potentiodynamic polarisation, and scanning electron microscope SEM were used and some thermodynamic parameters of corrosion process $\Delta G_{ads.}$, $\Delta H^{0}_{ads.}$, $\Delta S^{0}_{ads.} $ were evaluated. The steel surface was checked by SEM, and the steel surface showed good surface coverage. The results showed that the synthesized compounds at the concentrations 125, 150 mg x L$^{-1}$ have corrosion inhibition activity of 78%-95% by gravimetric measurements and 8%-92% by potentiodynamic measurements at 100, 150 mg x L$^{-1}$. The biological activity was examined against sulphate-reducing bacteria SRB . It was revealed that at the concentration of compounds 4c and 4d, 100 mg x L$^{-1}$, the antibacterial activity was 100%.

Keywords:

Piperidinium halides phenolic compounds, corrosion inhibitors, adsorption, biocides,

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1. Tsoeunyane MG, Makhatha ME, Arotiba OA. Corrosion inhibition of mild steel by poly(butylene succinate)-Lhistidine extended with 1,6-diisocynatohexane polymer composite in 1 M HCl. International journal of corrosion 2019; Article ID 7406409: 12. doi: 10.1155/2019/7406409
2. Rbaa M, Galai M, Benhiba F, Obot IB, Oudda H et al. Sinthesis and investigation of quinazoline derivatives based on 8-hydroxyquinoline as corrosion inhibitors for mild steel in acidic environment: experimental and theoretical studies. Ionics 2019; 25: 3473-3491. doi: 10.1007/s11581-018-2817-7
3. Chakravarthy MP, Mohana KN. Adsorption and Corrosion Inhibition Characteristics of Some Nicotinamide Derivatives on Mild Steel in Hydrochloric Acid Solution. ISRN Corrosion 2014; Article ID 687276. doi: 10.1155/ 2014/687276
4. Abd El-Lateef HM, Tantawy AH, Abdelhamid AA. Novel quaternary ammonium-based cationic surfactants: synthesis, surface activity and evaluation as corrosion inhibitors for C1018 carbon steel in acidic chloride solution. Journal of Surfactants and Detergents 2017; 20: 735-753. doi: 10.1007/s11743-017-1947-7
5. Abdel Hameed RS, Alfakeer M, Abdallah M. Inhibiting properties of some heterocyclic amide derivatives as potential nontoxic corrosion inhibitors for carbon steel in 1.0 M sulfuric acid. Surface engineering and applied electrochemistry 2018; 54: 599-606. doi: 10.3103/S1098375518060054
6. Santos da Silva P, Ferrera de Senna L, Maccado Goncalves MM, Baptista do Lago DC. Microbyologically-influenced corrosion of 1020 carbon steel in Artificial Seawater using garlic oil as natural biocide. Materials research 2019; 22: e20180401. doi: 10.1590/1980-5373-MR-2018-0401
7. Manga SS, Oyeleke SB, Ibrahim AD, Aliero AA, Bagudo AI. Influence of bacteria associated with corrosion of metals. Continental journal of microbiology 2012; 6: 19-25
8. Badawi AM, Hegazy MA, El-Sawy AA, Ahmed HM, Kamel WM. Novel quaternary ammonium hydroxide cationic surfactants as corrosion inhibitors for carbon steel and as biocides for sulfate-reducing bacteria (SRB). Materials Chemistry and Physics 2010; 124: 458-465. doi: 10.1016/j.matchemphys.2010.06.066
9. Kudryavtsev DB, Panteleeva AR, Yurina AV, Lukashenko SS, Khodyrev YP et al. Polymeric inhibitors of hydrogen sulfide corrosion. Russian Journal of Petroleum Chemistry 2009; 49 (3): 193-198. doi: 10.1134/S0965544109030025
10. Sikachina A. Polyaminopolyphosðíonates and polyaminopolycarbonates (that are chelators) in mission of inhibiting of microbiological corrosion with Desulfovibrio desulfuricans. Bulletin of Science and Practice 2017; 6: 24-40. doi: 10.5281/zenodo.808189
11. Ashassi-Sorkhabi H, Asghari E, Ejbari P. Electrochemical Studies of Adsorption and Inhibitive Performance of Basic Yellow 28 Dye on Mild Steel Corrosion in Acid Solutions. Acta Chimica Sloveniya 2011; 58: 270-277.
12. Vishwanatham S, Haldar N. Furfuryl alcohol as corrosion inhibitor for N80 steel in hydrochloric acid. Corrosion Science 2008; 50 (11): 2999-3004. doi: 10.1134/ S0965544109030025
13. Offurum FC, Oguzie EE, Offurum JC. Surface response methodology for mild steel corrosion control using udara bark extract as inhibitor. Continental Journal of Engineering Sciences 2017; 12 (1): 20-29. doi: 10.5281/zenodo.580792
14. Deivanayagam P, Malarvizhi I, Selvaraj S. Corrosion inhibition efficacy of ethanolic extract of mimusops elengi leaves (MEL) on copper in natural sea water. International Journal of Multidisciplinary Research and Development 2015; 2 (4): 100-107. doi: 10.22271/ijmrd
15. Abd El Rehim SS, Abdel-Fatah HT, El-Sehiety HE. Inhibitive action of Cystine on the corrosion of low alloy steel ASTM A213 grade T22 in sulfamic acid solutions. Arabian Journal of chemistry 2016; 9: 388-394. doi: 10.1016/j.arabjc.2011.05.003
16. Abeng FE, Idim VD, Obonovo OE, Magu TO. Adsorbtion and adsorption isotherms: application to corrosion inhibition studies of mild steel in 2 M HCl. World Scientific News 2017; 77 (2): 298-313.
17. Asassi-Sorkhabi H, Seifzadeh D. Analysis of raw and trend removed EN data in time domain to evaluate corrosion inhibition effects of New Fuchsin dye on steel corrosion and comparison of results with EIS. Journal of Applied Electrochemistry 2008; 38 (11): 1545-1552. doi: 10.1007/s10800-008-9602-7
18. Asassi-Sorkhabi H, Seifzadeh D, Hosseini MG. EN, EIS and polarization studies to evaluate the inhibition effect of 3H-phenothiazin-3-one, 7-dimethylamin on mild steel corrosion in 1M HCl solution. Corrosion Science 2008; 50 (12): 3363-3370. doi: 10.1016/j.corsci.2008.09.022
19. Asassi-Sorkhabi H, Shaabani B, Seifzadeh D. Effect of some pyrimidinic Schiff bases on the corrosion of mild steel in hydrochloric acid solution. Electrochimica Acta 2005; 50: 3446-3452. doi: 10.1016/j.electacta.2004.12.019
20. Al-Novayzer FM, Abdalla M, El-Mossalami EX. N,N-di-(polyoxyethylene)-4-dodecylanyline as corrosion inhibitor for steel in hydrochloric acid solutions. Russian Journal of Chemistry and Technology of Fuels and Oils 2012; 6: 453-463. doi: 10.1007/s10553-012-0324-5
21. Sikachina A. Inhibition of corrosion with organic compounds in the water and salt and acid medium. The aspect of izomerism and the interclass aspect of the inhibition process. Bulletin of Science and Practice 2018; 4 (1): 10-23. doi: 10.5281/ zenodo.1146983
22. Elemike EE, Nwankwo HU, Onwundiwe DC, Hosten EC. Sinthesis, structures, spectral properties and DFT quantum chemical calculations of (E)-4-(((4-propylphenyl)imino)methyl)phenol and (E)-4-((2-tolylimino)methyl)phenol; their corrosion inhibition studies of mild steel in aqueous HCl. Journal of Molecular Structure 2017; 1141: 12-22. doi: 10.1016/j.molstruc.2017.03.071
23. Batyeva ES, Ugryumov OV, Varnavskaya OA, Khodyrev YuP, Platov EV et al. New, effective carbon dioxide and hydrogen sulfide corrosion inhibitors based on white phosphorus, sulfur, alcohols, and amines. Russian Journal of Petroleum Chemistry 2013; 53: 139-143. doi: 10.1134/S0965544113020138
24. Rakhmatullin RR, Levashova VI, Dekhtyar’ TF. Synthesis and properties of quaternary ammonium salts on the basis of piperidine. Russian Journal of Petroleum Chemistry 2013; 53: 134-138. doi: 10.1134/S0965544113020102
25. Kudryavtsev DB, Panteleeva AR, Yurina AV, Lukashenko SS, Khodyrev YP et al. Polymeric inhibitors of hydrogen sulfide corrosion. Russian Journal of Petroleum Chemistry 2009; 49: 193-198. doi: 10.1134/S0965544109030025
26. Veliev MG, Chalabieva AZ, Vezirova IA, Shatirova MI, Gadzhieva MI. Functional derivatives of acetylene as reagents for inhibiting the growth of sulfate-reducing bacteria in oil production. Russian Journal of Petroleum Chemistry 2010; 50: 484-488. doi: 10.1134/S0965544110060137
27. Batyeva ES, Ugryumov OV, Varnavskaya OA, Khodyrev YP, Platova EV. New, effective carbon dioxide and hydrogen sulfide corrosion inhibitors based on white phosphorus, sulfur, alcohols, and amines. Russian Journal of Petroleum Chemistry 2013; 53: 139-143. doi: 10.1134/S0965544113020138
28. Mekhtiyeva GM, Magerramov AM, Bairamov MR, Agayeva MA, Khoseinzadeh SB et al. Alkenylphenol-based pyridinium salts as hydrogen sulfide corrosion inhibitors and agents for inhibiting the growth of sulfate-reducing bacteria in oil production. Russian Journal of Petroleum Chemistry 2015; 55 (3): 247-251. doi: 10.1134/S0965544115030081
29. Maharramov AM, Bairamov MR, Agayeva MA, Mehdiyeva GM, Mammadov IG. Alkenylphenols: preparation, transformation and application. Russian Chemical Review 2015; 84: 1258-1278. doi: 10.1070/RCR4437.
30. Maras N, Polane S, Kocevar M. Synthesis of Aryl Alkyl Ethers by Alkylation of Phenols with Quaternary Ammonium Salts. Acta Chimica Slovenica 2010; 57 (1): 29-36.
31. Hirschbeck V, Gehrtz PH, Fleischer I. Regioselective thiocarbonylation of vinyl arenes. Journal of American Chemical Society 2016; 138 (51): 16794-16799. doi: 10.1021/jacs.6b11020
32. Kohei W, Takashi M, Eri I, Chihiro M, Yasushi Y et al. Hydrazone–Pd-catalyzed direct intermolecular reaction of o-alkynylphenols with allylic acetates. Organic and Biomolecular Chemistry 2018; 4 (16): 575-584. doi: 10.1039/C8OB90094
33. Po-Yuan Ch, Yi-Hua W, Mon-Huei H, Tzu-Pin W. Cerium Ammonium Nitrate-Mediated the Oxidative Dimerization of p-Alkenylphenols: A New Synthesis of Substituted (+ -)-trans-Dihydrobenzofurans. ChemInform 2013; 69 (2): 653-657. doi: 10.1016/j.tet.2012.11.006
34. Castro AM. Claisen Rearrangement over the Past Nine Decades. Chemical Review 2004; 104: 2939-3002. doi: 10.1021/cr020703u
35. Yoshida NC, Benedetti AM, Dos Santos RA, Ramos CS, Batista R et al. Alkenylphenols from Piper dilatatum and P. diospyrifolium. Phytochemistry Letters 2018; 25: 136-140. doi: 10.1016/j.phytol.2018.04.006
36. Horikoshi S, Matsuzaki Sh, Mitani T, Serpone N. Microwave frequency effects on dielectric properties of some common solvents and on microwave-assisted syntheses: 2-Allylphenol and the C12 -C2 -C12 Gemini surfactant. Radiation Physics and Chemistry 2012; 81: 1885-1895. doi: 10.1016/j.radphyschem.2012. 07.011
37. Krivoruchko EV. Phenolic compounds of Cornus mas and Cornus officinalis. Chemistry of Natural Compounds 2018; 54 (1): 646-647. doi: 10.24959/ubphj.18.151
38. Gavezotti P, Navarra S, Caufin S, Danielli B, Magrone P et al. Synthesis of Enantiomerically Enriched Dimers of Vinylphenols by Tandem Action of Laccases and Lipases. Advanced Synthesis and Catalysis 2011; 353: 2421-2430. doi: 10.1002/adsc.201100413
39. Sasano K, Takaya Y, Iwasawa N. Palladium(II)-Catalyzed Direct Carboxylation of Alkenyl C–H Bonds with CO2 . Journal of American Chemical Society 2013; 135: 10954-10957. doi: 10.1021/ja405503y
40. Musalov MV, Ishigeev RS, Udalova SI, Musalova MV, Kurkutov EO et al. Synthesis of fused compounds on the basis of chalcogen chlorides and 2-allylphenols. Russian Journal of Organic Chemistry 2018; 54: 1035-1040. doi: 10.1134/S1070428018070114
41. Maharramov AM, Bairamov MR, Mehdiyeva GM, Hoseinzadeh SB, Askerov RK. 1,4-Bis[2-(prop-1-enyl)phenoxy] butane. Acta Crystallographica Section E 2011; 67: o1478. doi: 10.1107/S1600536811018538
42. Maharramov AM, Bairamov MR, Mehdiyeva GM, Hoseinzadeh SB, Rashidov BA. 1,10-Bis[2-(prop-1-enyl)phenoxy] decane. Acta Crystallographica Section E 2012; E68: o266. doi: 10.1107/S1600536811055061
43. Qu T, Zhang J, Meng Z, Liu X, Cao Y et al. Metabolism of fungicide 2-allylphenol in Rhizoctonia cerealis. Ecotoxicology and Environmental Safety 2014; 102: 136-141. doi: 10.1016/j.ecoenv.2014.01.025
44. Maharramov AM, Bairamov MR, Hoseinzadeh ShB, Agayeva MA, Mehdiyeva GM et al. Synthesis of hydrogen sulfide corrosion inhibitors for oil production. Russian journal of Petroleum Chemistry 2013; 53 (6): 423-425. doi: 10.1134/S0965544113060121
45. Rani R, Arora S, Kaur J, Kumari M. Phenolic compounds as antioxidants and chemopreventive drugs from Streptomyces cellulosae strain TES17 isolated from rhizosphere of Camellia sinensis. BMC Complementary and Alternative Medicine 2018; 18 (1): 82-86. doi: 10.1186 /s12906-018-2154-4
46. Maharramov AM, Bairamov MR, Mehdiyeva GM, Agayeva MA. Study of radical copolymerization of aminomethylated derivatives of alkenylphenols with styrene. Russian Journal of Polymer Science B 2012; 54 (7-8): 399-406. doi: 10.1134/ S1560090412080039
47. Maharramov AM, Bayramov MR, Mehdiyeva GM, Agayeva MA, Mammadova PS et al. Synthesis of aminomethylated derivatives of allylphenols and study of their antimicrobial characteristics in motor oil. Russian Journal of Applied Chemistry 2007; 80: 665-668. doi: 10.1134/S1070427207040295
48. Maharramov AM, Bayramov MR, Mehdiyeva GM, Agayeva MA, Mammadova PS et al. Study of aminomethylation derivatives of allylphenols as antimicrobial additives for TS-1 jet fuel. Russian Journal of Petroleum Chemistry 2008; 48: 63-66. doi: 10.1134/S096554410801012X
49. Maharramov AM, Bayramov MR, Mehdiyeva GM, Abushev RA, Agayeva MA et al. Aminomethylated derivatives of 2-propenyl- and 4-isopropenylphenols as antimicrobial additives for petroleum products. Russian Journal of Petroleum Chemistry 2010; 50: 69-73. doi: 10.1134/S096554411001010X
50. Vicca P, Steudel S, Smout S, Raats A, Genoe J et al. Interlayer Processing for Active Matrix Organic Light Emitting Diode (OLED) Displays. Thin Solid Films 2010; 519: 391-393. doi: 10.5772/19376
51. Chiu CJ, Pei ZW, Chang SP, Chang SJ. Influence of weight ratio of poly(4-vinylphenol) insulator on electronic properties of InGaZnO thin-film transistor. Journal of Nanomaterials 2012 (2012) Art.ID 698123. doi: 10.1155/2012/698123
52. Bairamov MR, Magerramov AM, Aliyev IA, Hosseinzadeh ShB, Mehdiyeva GM. Study of 2-allylphenol with symmetric dibromo(C1-C2)alkanes. Elmi Eserler — Fundamental Elmler. 2011; 37: 128-130.
53. RD 39-0147-103-350-89: Methodology for monitoring microbiological contamination of oilfield waters and evaluating the protective and bactericidal action of reagents. Ufa, Russia: VNIISSPTneft, 1989, pp. 21.
54. Hamadi L, Mansouri S, Oulmi K, Kareche A. The use of amino acids as corrosion inhibitors for metals: a review. Egyptian Journal of Petroleum 2018; 27: 1157-1165. doi: 10.1016/j.ejpe.2018.04.004
55. Mohan R, Joseph A. Corrosion protection of mild steel in hydrochloric acid up to 313 K usingpropyl benzimidazole: Electroanalytical, adsorption and quantumchemical studies. Egyptian Journal of Petroleum 2018; 27: 11-20. doi: 10.1016/j.ejpe.2016.12.003
56. Vekantesh R, Geetha K. Synthesis, characterization and antimicrobial activity of nickel (II) complexes derived from pentadentate schiff base. International Journal of Applied and Advanced Scientific Research. 2017; 2 (1): 94-98. doi: 10.5281/zenodo.259868