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.

Key words： corrosion inhibitors; mild steel; acidic medium; theoretical studies; DFT

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.

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