Synthesis of mono and bis-4-methylpiperidiniummethyl-urea as corrosion inhibitors for steel in acidic media
Synthesis of mono and bis-4-methylpiperidiniummethyl-urea as corrosion inhibitors for steel in acidic media
Abbas TEIMOURI1(), Nasrin SOLTANI2, Alireza Najafi CHERMAHINI3
1. Department of Chemistry, Payame Noor University (PNU), Isfahan 81395-671, Iran; 2. Department of Chemistry, Payame Noor University (PNU), Shahin Shahr Branch, Isfahan 83196, Iran; 3. Department of Chemistry, Yasouj University, Yasouj 75918-74831, Iran
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.
. Synthesis of mono and bis-4-methylpiperidiniummethyl-urea as corrosion inhibitors for steel in acidic media[J]. Frontiers of Chemical Science and Engineering, 2011, 5(1): 43-50.
Abbas TEIMOURI, Nasrin SOLTANI, Alireza Najafi CHERMAHINI. Synthesis of mono and bis-4-methylpiperidiniummethyl-urea as corrosion inhibitors for steel in acidic media. Front Chem Sci Eng, 2011, 5(1): 43-50.
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 doi: 10.1016/j.corsci.2005.05.034
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 doi: 10.1023/B:JACH.0000031160.88906.03
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 doi: 10.1016/j.corsci.2004.01.023
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 doi: 10.1023/A:1003450818083
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 doi: 10.1016/S0010-938X(03)00103-3
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 doi: 10.1007/BF00242066
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 doi: 10.1023/A:1016348710085
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 doi: 10.1016/S0010-938X(02)00099-9
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 doi: 10.1007/BF00348786
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 doi: 10.1016/S0010-938X(99)00049-9
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
Metiko?-Hukovi? M, Babi? R, Gruba? Z. The study of aluminium corrosion in acidic solution with nontoxic inhibitors. Journal of Applied Electrochemistry , 2002, 32(1): 35–41 doi: 10.1023/A:1014265407060
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 doi: 10.1016/S0010-938X(00)00076-7
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 doi: 10.1007/BF01092693
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 doi: 10.5006/1.3280577
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 doi: 10.1016/j.jelechem.2003.11.018
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 doi: 10.1016/j.porgcoat.2004.06.005
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 doi: 10.1023/A:1004099412974
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 doi: 10.5006/1.3293606
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 doi: 10.1016/j.porgcoat.2005.06.001
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 doi: 10.1016/S0010-938X(01)00109-3
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 doi: 10.1016/0010-938X(91)90043-O
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) doi: 10.1007/BF02704314
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 doi: 10.1108/EUM0000000005633
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 doi: 10.1016/j.dyepig.2005.12.002
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 doi: 10.1016/j.saa.2006.07.037
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 doi: 10.1016/j.saa.2007.04.024
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 doi: 10.1016/j.corsci.2005.06.007
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 PA 2001
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 doi: 10.1016/j.corsci.2008.06.020
34
Donahue F M, Nobe K. Theory of organic corrosion inhibitors. Journal of the Electrochemical Society , 1965, 112(9): 886–891 doi: 10.1149/1.2423723
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 doi: 10.1016/S0010-938X(02)00246-9
