Corrosion inhibitor activity of 1,3-diketone malonates for mild steel in aqueous hydrochloric acid solution

Corrosion Science

Volumn 61, Issue , 2012, Pages 171-184

  Fragoza Mar, Lubanski ^a   Olivares Xometl, Octavio ^b   Domínguez Aguilar, Marco A ^a   Flores, Eugenio A ^a   Arellanes Lozada, Paulina ^c   Jiménez Cruz, Federico ^a  

^a INSTITUTO MEXICANO DEL PETRÓLEO   (Mexico)

^b BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^c INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

Author keywords

A. Mild steel; B. Acid inhibition; B. Modelling studies; B. Polarization; C. Acid corrosion

Indexed keywords

ACID CORROSION; ACID INHIBITION; CORROSION INHIBITION EFFICIENCY; HYDROCHLORIC ACID SOLUTION; INHIBITOR EFFICIENCY; MALONATES; MODELLING STUDIES; MOLECULAR MOIETIES; POLARIZATION TESTS; QUANTUM CHEMICAL CALCULATIONS;

CORROSION INHIBITORS; CORROSION RESISTANCE; HYDROCHLORIC ACID; HYDROGEN; KETONES; POLARIZATION; QUANTUM CHEMISTRY;

CARBON STEEL;

EID: 84861938285     PISSN: 0010938X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.corsci.2012.04.031     Document Type: Article

References (55)

1. Granese S.L., Rosales B.M., Oviedo C., Zerbino J.O. The inhibition action of heterocyclic nitrogen organic compounds on Fe and steel in HCl media. Corros. Sci. 1992, 33:1439-1453.
2. Kel'in A.V. Recent advances in the synthesis of 1,3-diketones. Curr. Org. Chem. 2003, 7:1691-1711.
3. Gilli P., Bertolasi V., Ferreti V., Gilli G. Evidence for intramolecular N-H O resonance-assisted hydrogen bonding in β-enaminones and related heterodienes: a combined crystal-structural, IR and NMR spectroscopic, and quantum-mechanical investigation. J. Am. Chem. Soc. 2000, 122:10405-10417.
4. Jiménez-Cruz F., Maldonado L.A., Cetina R. A simple 1,5 → 1,3-diketone rearrangement. Tetrahedron Lett. 1998, 39:2685-2688.
5. Jiménez-Cruz F., Maldonado L.A., Cetina R., Ríos-Olivares H. Synthesis of 1-Aryl-1,3-diketones containing the dimethyl malonate moiety. Synth. Commun. 2000, 30:3439-3450.
6. Giacomelli F.C., Giacomelli M.F., Amadori M.F., Schmidt V., Spinelli A. A. Inhibitor effect of succinic acid on the corrosion resistance of mild steel: electrochemical, gravimetric and optical microscopic studies. Mater. Chem. Phys. 2004, 83:124-128.
7. 4. B. Electrochem. 1989, 5:319-323.
8. Ita B., Offiong O.E. The study of the inhibitory properties of benzoin, benzil, benzoin-(4-phenylthiosemicarbazone) and benzil-(4-phenylthiosemicarbazone) on the corrosion of mild steel in hydrochloric acid. Mater. Chem. Phys. 2001, 70:330-335.
9. M.F. Seijo, D.B. Bernhard, L. Nguyen, Formulations Including a 1,3-Dicarbonyl Compound Chelating Agent and Copper Corrosion Inhibiting Agent for Stripping Residues from Semiconductor Substrates Containing Copper Structures, US Patent 20020013238, 2002.
10. H.S. Gilbert, Compositions Containing Beta-diketochelating Compounds, US Patent 4324676, 1982.
11. Gece G. Drugs: a review of promising novel corrosion inhibitors. Corros. Sci. 2011, 53:3873-3898.
12. 4. Corros. Sci. 2011, 53:263-275.
13. Bouklah M., Hammouti B. Thermodynamic characterisation of steel corrosion for the corrosion inhibition of steel in sulphuric acid solutions by artemisia. Portugaliae Electrochim. Acta. 2006, 24:457-468.
14. Gaussian 03, Revision E.01, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. BakkenC. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M. W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Wallingford CT, 2004.
15. Becke A.D. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A 1988, 38:3098-3100.
16. Lee C., Yang W., Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37:785-789.
17. Sardella D.J., Heinert D.H., Shapiro B.L. Nuclear magnetic resonance studies of enol-enol and keto-enol equilibria in substituted benzoylacetones. J. Org. Chem. 1969, 34:2817-2821. A. Yogev, Y. Mazur, J. Org. Chem. 32(69) (1967) 2162.
18. Iglesias E. Enolization of benzoylacetone in aqueous surfactant solutions: a novel method for determining enolization constants. J. Phys. Chem. 1996, 100:12592-12599.
19. Beak P., Mills S.G. Solvent effects on keto-enol equilibria test of quantitative models. J. Org. Chem. 1985, 50:1216-1224.
20. Emsley J., Freeman N.J. β-diketone interactions - part 5: solvent effect on the keto enol equilibrium. J. Mol. Struct. 1987, 161:193-204.
21. Szauer T., Brandt A. Adsorption of oleates of various amines on iron in acidic solution. Electrochim. Acta. 1981, 26:1253-1256.
22. Ashassi-Sorkhabi H., Shaabani B., Seifzadeh D. Corrosion inhibition of mild Steel by some Schiff base compounds in hydrochloric acid. Appl. Surf. Sci. 2005, 239:154-164.
23. Zhang Q.B., Hua Y.X. Corrosion inhibition of mild Steel by alkylimidazolium ionic liquids in hydrochloric acid. Electrochim. Acta. 2009, 54:1881-1887.
24. Lebrini M., Bentiss F., Vezin H., Lagrenée M. The inhibition of mild steel corrosion in acidic solutions by 2,5-bis(4-pyridyl)-1,3,4-thiadiazole: structure-activity correlation. Corros. Sci. 2006, 48:1279-1291.
25. Tebbji K., Oudda H., Hammouti B., Benkaddour M., El Kodadi M., Ramdani A. Inhibition effect of two organic compounds pyridinepyrazole type in acidic corrosion of steel. Colloids Surfaces A: Physicochem. Eng. Aspects 2005, 259:143-149.
26. Krim O., Elidrissi A., Hammouti B., Ouslim A., Benkaddour M. Synthesis, characterization, and comparative study of pyridine derivatives as corrosion inhibitors of mild steel in HCl medium. Chem. Eng. Commun. 2009, 196:1536-1546.
27. Fu J.-J., Li S.-N., Cao L.-H., Wang Y., Yan L.-H., Lu L.-D. L-Tryptophan as green corrosion inhibitor for low carbon steel in hydrochloric acid solution. J. Mater. Sci. 2010, 45:979-986.
28. Shukla S.K., Quraishi M.A. The effects of pharmaceutical active compound doxycucline on the corrosion of mild steel in hydrochloric acid solution. Corros. Sci. 2010, 52:314-321.
29. Ahamad I., Prasad R., Quraishi M.A. Inhibition of mild steel corrosion in acid solution by Pheniramine drug: Experimental and theoretical study. Corros. Sci. 2010, 52:3033-3041.
30. Yadav D.K., Quraishi M.A., Maiti B. Inhibition effect of some benzylidenes on mild steel in 1M HCl: an experimental and theoretical correlation. Corros. Sci. 2012, 55:254-266.
31. Benabdellah M., Dafali A., Hammouti B., Aouniti A., Rhomari M., Raada A., Senhaji O., Robin J.J. The role of phosphonate derivatives on the corrosion inhibition of steel in HCl media. Chem. Eng. Commun. 2007, 194:1328-1341.
32. Shukla S.K., Quraishi M.A. 4-substituted anilinomethylpropionate: new and efficient corrosion inhibitors for mild steel in hydrochloric acid solution. Corros. Sci. 2009, 51:1990-1997.
33. Shukla S.K., Quraishi M.A. Cefotaxime sodium: A new and efficient corrosion inhibitor for mild steel in hydrochloric acid solution. Corros. Sci. 2009, 51:1007-1011.
34. Ali S.A., Al-Muallem H.A., Rahman S.U., Saeed M.T. Bis-isoxazolidines: a new class of corrosion inhibitors of mild steel in acidic media. Corros. Sci. 2008, 50:3070-3077.
35. Ahamad I., Prasad R., Quraishi M.A. Adsorption and inhibitive properties of some new Mannich bases of isatin derivatives on corrosion of mild steel in acidic media. Corros. Sci. 2010, 52:1472-1481.
36. Shanbhag A.V., Venkatesha T.V., Prabhu R.A., Kalkhambkar R.G., Kulkarni G.M. Corrosion inhibition of mild steel in acidic medium using hydrazides derivatives. J. Appl. Electrochem. 2008, 38:279-287.
37. Ali S.A., El-Sareef A.M., Al-Ghamdi R.F., Saeed M.T. The isoxazolidines: the effects of steric factor and hydrophobic chain length on the corrosion inhibition of mild steel in acidic medium. Corros. Sci. 2005, 47:2659-2678.
38. Kaddouri M., Cheriaa N., Souane R., Bouklah M., Aouniti A., Abidi R., Hammouti B., Vicens J. New calixarene derivatives as inhibitors of mild steel C-38 steel corrosion in 1 M HCl. J. Appl. Electrochem. 2008, 38:1253-1258.
39. Singh A.K., Quraishi M.A. Effect of 2,2'-benzothiazolyl disulfide on the corrosion of mild steel in acid media. Corros. Sci. 2009, 51:2752-2760.
40. Herrag L., Hammouti B., Elkadiri S., Aouniti A., Jama C., Vezin H., Bentiss F. Adsorption properties and inhibition of mild steel corrosion in hydrochloric solution by some newly synthesized diamine derivatives: experimental and theoretical investigations. Corros. Sci. 2010, 52:3042-3051.
41. Emeregül K.C., Hayvalí M. Studies on the effect of a newly synthesized Schiff base compound from phenazone and vanillin on the corrosion of steel in 2 M HCl. Corros. Sci. 2006, 48:797-812.
42. Satapathy A.K., Gunasekaran G., Sahoo S.C., Amit K., Rodrigues P.V. Corrosion inhibition by Justicia gendarussa plant extract in hydrochloric acid solution. Corros. Sci. 2009, 51:2848-2856.
43. Olivares O., Likhanova N.V., Gómez B., Navarrete J., Llanos-Serrano M.E., Arce E., Hallen J.M. Electrochemical and XPS studies of decylamides of alpha-amino acids adsorption on carbon steel in acidic environment. Appl. Surf. Sci. 2006, 252:2894-2909.
44. Saleh M.M., Atia A.A. Effects of structure of the ionic head of cationic surfactant on its inhibition of acid corrosion of mild steel. J. Appl. Electrochem. 2006, 36:899. O.L. Riggs, in: C.C. Nathan (Ed.), Corrosion Inhibitors, 2nd ed., Houston, TX, 1973.
45. Popova A.A., Sokolova E., Raicheva S., Christov M. AC and DC study of the temperature effect on mild steel corrosion in acid media in the presence of benzimidazole derivatives. Corros. Sci 2003, 45:33-58.
46. Gece G. The use of quantum chemical methods in corrosion inhibitor studies. Corros. Sci. 2008, 50:2981-2992.
47. Fukui K. Theory of Orientation and Stereoselection 1975, Springer-Verlag, New York.
48. Martinez S. Inhibitory mechanism of mimosa tannin using molecular modeling and substitutional adsorption isotherms. Mater. Chem. Phys. 2002, 77:97-102.
49. Gao G., Liang C. Electrochemical and DFT studies of β-amino-alcohols as corrosion inhibitors for brass. Electrochim. Acta 2007, 52:4554-4559.
50. 4 solution. Appl. Surf. Sci. 2007, 253:3913.
51. Allam N.K. Thermodynamic and quantum chemistry characterization of the adsorption of triazole derivatives during Muntz corrosion in acidic and neutral solutions. Appl. Surf. Sci. 2007, 253:4570-4577.
52. Ozcan M., Dehri I., Erbil M. Organic sulphur-containing compounds as corrosion inhibitors for mild steel in acidic media: correlation between inhibition efficiency and chemical structure. Appl. Surf. Sci. 2004, 236:155-164.
53. Kandemirli F., Sagdinc S. Theoretical study of corrosion inhibition of amides and thiosemicarbazones. Corros. Sci. 2007, 49:2118-2130.
54. Bereket G., Ogretic C., Ozsahim C. Quantum chemical studies on the inhibition efficiencies of some piperazine derivatives for the corrosion of steel in acidic medium. J. Mol. Struct. (THEOCHEM) 2003, 663:39-46.
55. Li W., He Q., Pei C., Hou B. Experimental and theoretical investigation of the adsorption behaviour of new triazole derivatives as inhibitors for mild steel corrosion in acid media. Electrochim. Acta 2007, 52:6386-6394.