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Preparation of Azo Dyes

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UNIVERSITY OF SAN CARLOS

DEPARTMENT OF CHEMISTRY

NAME: Maniwang, Ma. Aiza C. DATE: March 21, 2011

COURSE: BS Chemistry II APPROVED: ___________

PREPARATION OF AZO DYES

ABSTRACT

In this experiment, the azo dyes p-nitrobenzene azoresorcinol and methyl orange were prepared by the azo coupling reaction. The p-nitrobenzene azoresorcinol dye was prepared from p-nitroaniline and resorcinol. The diazonium salt formed was from the reaction of the cold solution of dissolved p-nitroaniline in hydrochloric acid and water with the solution of sodium nitrite. Azo coupling was then followed by letting the diazonium react with a solution of resorcinol in water and sodium hydroxide. The resulting mixture was treated with excess …show more content…

Since diazonium salt slowly decomposes even at ice bath temperature, the solution was used immediately after preparation. They are also very unstable and tend to be explosive as solids. Before proceeding to azo coupling, the resorcinol was first dissolved in sodium hydroxide giving a violet liquid.

When the solution of diazonium salt was poured into the cold solution made from resorcinol, water and sodium hydroxide, a violet solution was obtained. Adding concentrated HCl in excess converted the violet solution to red solution. The azo coupling reaction had already taken place in this part. This reaction occurs most rapidly near neutrality or in slightly acidic solution. An azo coupling is an organic reaction between a diazonium compound and aniline, phenol or other activated aromatic compounds, which produces an azo compound. In this reaction, the diazonium salt is an electrophiles and the activated arene is a nucleophile in an electrophilic aromatic substitution.

Helianthin (Methyl Orange)

Methyl orange is an azo dye that forms orange crystals and is used as an acid-base indicator. The anion form of this azo dye is yellow and the acid form is red. It is synthesized from sulfanilic acid and dimethylaniline using a diazonium coupling reaction.

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Figure 1. Correlation between the colors of the dye with its structure

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