The Synthesis of Imidazoline Derivative Compounds as Corrosion Inhibitor towards Carbon Steel in 1% NaCl Solution

Authors

  • Deana Wahyuningrum 1Organic Chemistry Research Group, Chemistry Department, Faculty of Mathematics and Natural Science, Institut Teknologi Bandung, Indonesia
  • Sadijah Achmad 1Organic Chemistry Research Group, Chemistry Department, Faculty of Mathematics and Natural Science, Institut Teknologi Bandung, Indonesia
  • Yana Maolana Syah 1Organic Chemistry Research Group, Chemistry Department, Faculty of Mathematics and Natural Science, Institut Teknologi Bandung, Indonesia
  • Buchari Buchari 2Analytical Chemistry Research Group, Chemistry Department, Faculty of Mathematics and Natural Science, Institut Teknologi Bandung, Indonesia
  • Bambang Ariwahjoedi 3Physical and Inorganic Chemistry Research Group, Chemistry Department, Faculty of Mathematics and Natural Science, Institut Teknologi Bandung, Indonesia

DOI:

https://doi.org/10.5614/itbj.sci.2008.40.1.4

Abstract

Oleic imidazoline is one of the nitrogen containing heterocyclic compounds that has been widely used as commercial corrosion inhibitor, especially in minimizing the carbon dioxide induced corrosion process in oilfield mining. In this present work, some imidazoline derivative compounds have been synthesized utilizing both conventional and microwave assisted organic synthesis (MAOS) methods, in order to determine their corrosion inhibition properties on carbon steel surface. The MAOS method is more effective in synthesizing these compounds than the conventional method regarding to the higher chemical yields of products (91% to 94%) and the shorter reaction times (7 to 10 minutes). The characterization of corrosion inhibition activities of the synthesized products towards carbon steel in 1% NaCl solution was determined by the Tafel plot method. The corrosion inhibition activities of compound 1b ((Z)-2-(2-(heptadec-8-enyl)-4,5-dihydroimidazol-1-yl)ethanamine), 2b ((Z)-2-(2-(heptadec-8-enyl)-4,5-dihydroimidazol-1-yl)ethanol) and 3b (2-(2-heptadecyl-4,5-dihydroimidazol-1-yl)ethanamine) at 8 ppm concentration in 1% NaCl solution are, respectively, 32.18%, 39.59% and 12.73%. The heptadec-8-enyl and hydroxyethyl substituents at C(2) and N(1) position of imidazoline ring, respectively, gave the most effective corrosion inhibition activity towards carbon steel compared to the presence of other substituents. The increase in concentrations of compound 1b, 2b and 3b in 1% NaCl solution tends to improve their corrosion inhibition activities. Based on the analysis of the free Gibbs adsorption energy (G0ads) values of compound 1b, 2b and 3b (-32.97, -34.34 and -31.27 kJ/mol, respectively), these compounds have the potential to interact with carbon steel through semi-physiosorption or semi-chemisorption.

References

Hong, T. & Jepson, W.P., Corrosion Inhibitor Studies in Large Flow Loop at High Temperature and High Pressure, Corrosion Science, 43, 1839-1849, 2001.

Cao, P., Gu, R. & Tian, Z., Surface-Enhanced Raman Spectroscopy Studies on the Interaction of Imidazole with a Silver Electrode in Acetonitrile Solution, J. Phys. Chem. B., 107, 769-7773, 2003.

Zhao, L., et al., Corrosion Inhibition Approach of Oil Production Systems in Offshore Oilfield, Materials and Corrosion, 55(9), 684-688, 2004.

Edwards, A., Osborn, C., Webster, D.K., Ostovar, J.P. & Doyle, M., Mechanistic Studies of the Corrosion Inhibitor Oleic Imidazoline, Corrosion Science, 36(2), 315-325, 1994.

Ali Hassanzadeh, et al., Inhibitor Selection Based On Nichols Plot in Corrosion Studies, Acta. Chim. Slov., 51, 305a^316, 2004.

Gomma, G.K., Effect of Azole Compounds on Corrosion of Copper in Acid Medium, Materials Chemistry and Physics, 56, 27-34, 1998.

Popova, A., Christov, M., Raicheva, S. & Sokolova, E., Adsorption and Inhibitive Properties of Benzimidazole Derivatives in Acid Mild Steel Corrosion, Corrosion Science, 46, 1333-1350, 2004.

Raicheva, S.N., Aleksiev, B.V. & Sokolova, E.I., The Effect of The Chemical Structure of Some Nitrogen- and Sulphur-Containing Organic Compounds on Their Corrosion Inhibiting Action, Corrosion Science, 34(2), 343-350, 1992.

Ramachandran, S., Jovancicevic, V., Molecular Modelling of the Inhibition of Mild Steel Carbon Dioxide Corrosion by Imidazolines, Corrosion, 55(33), 259-267, 1999.

Ramachandran, S., Tsai, B.L., Blanco, M., Chen, H., Tang, Y. & Goddard III, W.A., Atomistic Simulations of Oleic Imidazolines Bound to Ferric Clusters, J. Phys. Chem. A, 101, 83-89, 1997.

Ramachandran, S., Tsai, BL., Blanco, M., Chen, H., Tang, Y. & Goddard III, W.A., Self-Assembled Monolayer Mechanism for Corrosion Inhibitor of Iron by Imidazolines, Langmuir, 12, 6419-6428, 1996.

Frantz, D.E., et al., Synthesis of Substituted Imidazoles via Organocatalysis, Organic Letters, 2004. 6(5), 843-846.

Kappe, C.O., Controlled Microwave Heating in Modern Organic Synthesis, Angew. Chem. Int. ed., 43, 6250-6284, 2004.

Usyatinsky, A.Y. & Y.L. Khmelnitsky, Microwave-Assisted Synthesis of Substituted Imidazole on A Solid Support Under Solvent-Free Conditions, Tetrahedron Letters, 41, 5031-5034, 2000.

Wolkenberg, S.E., et al., Efficient Synthesis of Imidazoles from Aldehydes and 1,2-Diketones Using Microwave Irradiation, Organic Letters, 6(9), 1453-1456, 2004.

Abdel-Jalil, R.D., Voelter, W. & Stoll, R., Microwave-assisted synthesis of 1-aryl-3-acetyl-1,4,5,6-tetrahydrobenzimidazo[1,2-d][1,2,4]triazine: first example of a novel ring system, Tetrahedron Letters, 46, 1725-1726, 2005.

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Issue

Vol. 40 No. 1 (2008)

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Articles