Synthesis of mono and bis-4-methylpiperidiniummethyl-urea as corrosion inhibitors for steel in acidic media

Abstract

Mono and bis-4-methylpiperidiniummethyl urea were synthesized, characterized and used as new corrosion inhibitors of mild steel in the acidic media. Inhibitory effect of two compounds on mild steel surface in the 1 mol·L^-1 sulphuric acid has been studied by a series of techniques, such as potentiodynamic polarization, weight loss and quantum chemical calculation methods. Potentiodynamic polarization measurements showed that two inhibitors are mixed type. All measurements showed that inhibition efficiencies enhanced with increase of inhibitor concentration. This reveals that inhibitive actions of inhibitors were mainly due to adsorption on mild steel surface. Density functional (DFT) calculations have been carried out for the title compounds by performing HF and DFT levels of theory using the standard 6-31G* basis set.

Keywords

corrosion inhibitors / mild steel / acidic medium / theoretical studies / DFT

References

[1] Bentiss F, Lebrini M, Lagrenee M. Thermodynamic characterization of metal dissolution and inhibitor adsorption processes in mild steel/2,5-bis(n-thienyl)-1,3,4-thiadiazoles/hydrochloric acid system. Corrosion Science, 2005, 47(12): 2915–2931

[2] Khaled F, Babic-Samardzija K, Hackerman N. Piperidines as corrosion inhibitors for iron in HCl. Journal of Applied Electrochemistry, 2004, 34(7): 697–704

[3] Wang H L, Liu R B, Xin J. Inhibiting effects of some mercapto-triazole derivatives on the corrosion of mild steel in 1.0 M HCl medium. Corrosion Science, 2004, 46(10): 2455–2466

[4] El-Rehim S S A, Ibrahim M A M, Khaled K F. 4-Aminoantipyrine as an inhibitor of mild steel corrosion in HCl solution. Journal of Applied Electrochemistry, 1999, 29(5): 593–599

[5] Zor S, Dogan P, Yazici B. Inhibition of acidic corrosion of iron and aluminium by SDBS at different temperatures. Corros Rev, 2005, 23: 217–232

[6] Emregül K C, Kurtaran R, Atakol O. An investigation of chloride-substituted Schiff bases as corrosion inhibitors for steel. Corrosion Science, 2003, 45(12): 2803–2817

[7] Rengamani S, Muralidharan S, Anbu K M, Venkatakrishna I S. Inhibiting and accelerating effects of aminophenols on the corrosion and permeation of hydrogen through mild steel in acidic solutions. Journal of Applied Electrochemistry, 1994, 24(4): 355–360

[8] Quraishi M A, Jamal D. Inhibition of mild steel corrosion in the presence of fatty acid triazoles. Journal of Applied Electrochemistry, 2002, 32(4): 425–430

[9] Ali S, Saeed M T, Rahman S U. The isoxazolidines: a new class of corrosion inhibitors of mild steel in acidic medium. Corrosion Science, 2003, 45(2): 253–266

[10] Zvauya R, Dawson J L. Inhibition studies in sweet corrosion systems by a quaternary ammonium compound. Journal of Applied Electrochemistry, 1994, 24(9): 943–947

[11] Bentiss F, Traisnel M, Lagrenee M. The substituted 1,3,4-oxadiazoles: a new class of corrosion inhibitors of mild steel in acidic media. Corrosion Science, 2000, 42(1): 127–146

[12] Schmitt G. Application of inhibitors in acid media. Report prepared for the European Federation of Corrosion Working Party on Inhibitors. Br Corros J, 1984, 19(4): 165–176

[13] Metikoš-Huković M, Babić R, Grubač Z. The study of aluminium corrosion in acidic solution with nontoxic inhibitors. Journal of Applied Electrochemistry, 2002, 32(1): 35–41

[14] Lagrenée M, Mernari B, Chaibi N, Traisnel M, Vezin H, Bentiss F. Investigation of the inhibitive effect of substituted oxadiazoles on the corrosion of mild steel in HCl medium. Corrosion Science, 2001, 43(5): 951–962

[15] Agrawal R, Namboodhiri T K G. The inhibition of corrosion and hydrogen embrittlement of AISI 410 stainless steel. Journal of Applied Electrochemistry, 1992, 22(4): 383–389

[16] Khamis E. The effect of temperature on the acidic dissolution of steel in the presence of inhibitors. Corrosion, 1990, 46: 476–484

[17] Bentiss F, Lagrene’e M, Traisnel M. 2,5-Bis(n-Pyridyl)-1,3,4-oxadiazoles as corrosion inhibitors for mild steel in acidic media. Corrosion, 2000, 56(7): 733–742

[18] Cruz J, Martínez R, Genesca J, García-Ochoa E. Experimental and theoretical study of 1-(2-ethylamino)-2-methylimidazoline as an inhibitor of carbon steel corrosion in acid media. Journal of Electroanalytical Chemistry, 2004, 566(1): 111–121

[19] Bouklah M, Benchat N, Aouniti A, Hammouti B, Benkaddour M, Lagren’ee M, Vezin H, Bentiss F. Effect of the substitution of an oxygen atom by sulphur in a pyridazinic molecule towards inhibition of corrosion of steel in 0.5 M H₂SO₄ medium. Progress in Organic Coatings, 2004, 51(2): 118–124

[20] Quraishi M A, Rawat J, Ajmal M. A novel class of acid corrosion inhibitors for mild steel. Journal of Applied Electrochemistry, 2000, 30(6): 745–751

[21] Hammouti B, Aouniti A, Taleb M, Brighli M, Kertit S. L-Methionine methyl ester hydrochloride as a corrosion inhibitor of iron in acid chloride solution. Corrosion, 1995, 51(6): 411–416

[22] Tebbji K, Aouniti A, Benkaddour M, Oudda H, Bouabdallah I, Hammouti B, Ramdani A. New bipyrazolic derivatives as corrosion inhibitors of steel in 1M HCl. Progress in Organic Coatings, 2005, 54(3): 170–174

[23] Huynh N, Bottle S E, Notoya T, Trueman A, Hinton B, Schweinsberg D P. Studies on alkyl esters of carboxybenzotriazole as inhibitors for copper corrosion. Corrosion Science, 2002, 44(6): 1257–1276

[24] Sankarapapavinasam S, Pushpanaden F, Ahmed M F. Piperidine, piperidones and tetrahydrothiopyrones as inhibitors for the corrosion of copper in H₂SO₄. Corrosion Science, 1991, 32(2): 193–203

[25] Muralidharan S, Chandrasekar R, Iyer S V. Effect of piperidones on hydrogen permeation and corrosion inhibition of mild steel in acidic solutions. Proceedings of the Indiana Academy of Sciences, 2000, 112(2): 127–136 (Chem Sci)

[26] Athar Suroor S M, Ali H, Quraishi M A. A study of some new organic inhibitors on corrosion of N-80 and mild steel in hydrochloric acid. Anti-Corros Methods Mater, 2001, 48(4): 251–255

[27] Dabbagh H A, Teimouri A, Chermahini A N. Green and efficient diazotization and diazo coupling reactions on clays. Dyes and Pigments, 2007, 73(2): 239–244

[28] Dabbagh H A, Teimouri A, Chermahini A N, Shiasi R. DFT and ab initio calculations of the vibrational frequencies and visible spectra of triazenes derived from cyclic amines. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2007, 67(2): 437–443

[29] Dabbagh H. A, Teimouri A, ChermahiniA N, Shahraki M. DFT and ab initio study of structure of dyes derived from 2-hydroxy and 2,4-dihydroxy benzoic acids. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, 69(2): 449–459

[30] Zhang D Q, An Z X, Pan Q Y, Gao L X, Zhou G D. Comparative study of bis-piperidiniummethyl-urea and mono-piperidiniummethyl-urea as volatile corrosion inhibitors for mild steel. Corrosion Science, 2006, 48(6): 1437–1448

[31] ASTM. Standard Practice for Laboratory Immersion Corrosion Testing of Metals, G 31-72, ASTM, Philadelphia, PA, 1990, 401

[32] Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Montgomery J A Jr, Vreven T, Kudin K N, Burant J C, Millam J M, Iyengar S S, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson G A, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox J E, Hratchian H P, Cross J B, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R, Pomelli C, Ochterski J W, Ayala P Y, Morokuma K, Voth G A, Salvador P, Dannenberg J J, Zakrzewski V G, Dapprich S, Daniels A D, Strain M C, Farkas O, Malick D K, Rabuck A D, Raghavachari K, Foresman J B, Ortiz J V, Cui Q, Baboul A G, Clifford S, Cioslowski J, Stefanov B B, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin R L, Fox D J, Keith T, Al-Laham M A, Peng C Y, Nanayakkara A, Challacombe M, Gill P M W, Johnson B, Chen W, Wong M W, Gonzalez C, Pople J A. Gaussian Inc, Pittsburgh PA2001

[33] Behpour M, Ghoreishi S M, Soltani N, Salavati-Niasari M, Hamadanian M, Gandomi A. Electrochemical and theoretical investigation on the corrosion inhibition of mild steel by thiosalicylaldehyde derivatives in hydrochloric acid solution. Corrosion Science, 2008, 50(8): 2172–2181

[34] Donahue F M, Nobe K. Theory of organic corrosion inhibitors. Journal of the Electrochemical Society, 1965, 112(9): 886–891

[35] Hosseini M, Mertens S F L, Arshadi M R. Synergism and antagonism in mild steel corrosion inhibition by sodium dodecylbenzenesulphonate and hexamethylenetetramine. Corrosion Science, 2003, 45(7): 1473–1489

[36] Wang H L, Liu R B, Xin J. Inhibiting effects of some mercapto-triazole derivatives on the corrosion of mild steel in 1.0 M HCl medium. Corrosion Science, 2004, 46(10): 2455–2466

Acknowledgments

This study was financially supported by Payame Noor University in Isfahan research fund. The authors would like to thank Mr. M. Emami for his contributions in computational calculations.

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2014 Higher Education Press and Springer-Verlag Berlin Heidelberg