Syntheses of Azo-Imine Derivatives from Vanillin as an Acid Base Indicator

https://doi.org/10.22146/ijc.21318

Bambang Purwono(1*), Chairil Anwar(2), Ahmad Hanapi(3)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(3) Department of Chemistry, Faculty of Science and Technology, UIN Maulana Malik Ibrahim, Malang
(*) Corresponding Author

Abstract


Preparations of azo, imine and azo-imine derivatives from vanillin as an indicator of acid-base titration have been carried out. The azo derivative of 4-hydroxy-3-methoxy-5-(phenylazo)benzaldehyde 2 was produced by diazotitation reaction of vanillin in 37.04% yield. The azo product was then refluxed with aniline in ethanol to yield azo-imine derivatives, 2-methoxy-6-(phenylazo)-4-((phenylimino)methyl)phenol 1 in 82.21% yield. The imine derivative, 2-methoxy-4-((phenylimino)methyl)-phenol 3 was obtained by refluxing of vanillin and aniline mixture in ethanol solvent and produced 82.17% yield. The imine product was then reacted with benzenediazonium chloride salt. However, the products indicated hydrolyzed product of 4-hydroxy-3-methoxy-5-(phenylazo)benzaldehyde 2 in 22.15% yield. The 2-methoxy-4-((phenylimino)methyl)phenol 2 could be used as an indicator for titration of NaOH by H2C2O4 with maximum concentration of H2C2O4 0.1 M while the target compound 1 could be used as titration indicator for titration of NaOH with H2C2O4 with same result using phenolphthalein indicator.

Keywords


vanillin; indicator of acid-base titration; azo-imine group

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References

[1] Purwono, B., and Mahardiani, 2009, Indo. J. Chem., 9, 1, 95–98.

[2] Khan, P.A., and Farooqui, M., 2011, J. Adv. Sci. Res., 2, 4, 20–27.

[3] Kirkan, B., and Gup, R., 2008, Turk. J. Chem., 32, 9–17.

[4] Al-Rubaie, L.A., and Mhessn, R.J., 2012, E-J. Chem., 9, 1, 465–470.

[5] Carofiglio, T., Fregonese, C., Mohr, G.J., Rastrelli, F., and Tonellato, U., 2006, Tetrahedron, 62, 1502–1507.

[6] Makedonski, P., Brandes, M., Grahn, W., Kowalsky, W., Wichern, J., Wiese, S., and Johannes, H-H, 2004, Dyes Pigm., 61, 2, 109–119.

[7] Hinks, D., Freeman, H.S., Arai, Y., and Ando, H., 2001, Dyes Pigm., 48, 1, 7–13.

[8] Khalil, R.A., Jalil, A.H., and Abd-Alrazzak,A.Y., 2009, J. Iran. Chem. Soc., 6, 2, 345–352.

[9] Ibrahim, M.N., and Sharrif, S.A.I., 2011, E-J. Chem., 8, 1, 180–184.

[10] Noroozi-Pesyan, N., Khalafy, J., and Malekpoor, Z., 2009, Prog. Color Colorants Coat., 2, 1, 61–70.

[11] Huang, Z., Wan, D., and Huang, J., 2001, Chem. Lett., 708–709.



DOI: https://doi.org/10.22146/ijc.21318

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Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

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