Indonesian Journal of Chemistry
Vol 13, No 1 (2013)

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

Bambang Purwono (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281)
Chairil Anwar (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281)
Ahmad Hanapi (Department of Chemistry, Faculty of Science and Technology, UIN Maulana Malik Ibrahim, Malang)



Article Info

Publish Date
06 May 2013

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.

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Journal Info

Abbrev

ijc

Publisher

Subject

Chemical Engineering, Chemistry & Bioengineering Chemistry

Description

Indonesian Journal of Chemistry is an International, peer-reviewed, open access journal that publishes original research articles, review articles, as well as short communication in all areas of chemistry including applied chemistry. The journal is accredited by The Ministry of Research, Technology ...