One of the most important classes of dyes in the industry are azo dyes, compounds that

have the general structure of Ar-N=N-Ar,’ in which Ar and Ar’ are two aromatic fragments
(Solomons, 2011). Many of the dyes in this class are used typically as pH indicators because of
their ability to function as weak or strong acids or bases. Common examples of azo dyes which
are used as pH indicators are methyl red, methyl orange, and congo red. Aside from that, they
also have numerous industrial uses such as artificial color source for textile, food and beverage,
and clothing (Mcmurry, 2008).
The color of these dyes are credited to the azo linkage, N=N, which brings two aromatic
rings together. These aromatic compounds, also called chromopores, are responsible for the
colors of the dyes (Al-Rubaie & Mhessn, 2012). The conjugation from an electron-donating group
through the N=N bridge to an electron-withdrawing group on the other side results to an intense
color. There are changes in color due to the extended system of delocalized p electron that allows
the absorption of light in the visible region of the EM spectrum (Solomons, 2011)
These compounds are a result of a two-step reaction involving a diazonium salt and
coupling component. First, an aromatic diazonium ion from an aniline derivative is synthesized.
In this diazotization reaction, the primary arylamine reacts with nitrous acid to produce the
intermediate, an arenediazonium salt. The arenediazonium salt, a weak electrophile, is then
coupled with aromatic substrates such as phenols and tertiary amines (McMurry, 2008). An Azo
compound is the end product of this reaction.

Fig 1. Coupling mechanism of an arenediazonium salt and an aromatic substrate (McMurry, 2008)

The aim of this experiment was to synthesize 1-(phenylazo)-2-napthanol or Sudan-I dye

through a two-step reaction, diazotization and coupling. A red/orange product was expected to
be produced after executing the steps for the reactions. After successfully attaining a yield, the
physical properties of the azo dye were noted.

Al-Rubaie, L. A. A. R., & Mhessn, R. J. (2012). Synthesis and characterization of azo dye para red
and new derivatives. Journal of Chemistry, 9(1), 465-470. Chicago
McMurry, J. (2008). Organic Chemistry. (7th ed.). Brooks/Cole.
Solomons, G. T. W., & Fryhle, C. (2011). Organic Chemistry. (10th ed.). USA: John Wiley & Sons
Inc.
Conclusion:

Don’t mind notes lang.

This experiment was conducted to synthesized 1-phenylazo-2-naphthol or Sudan-1, a

powdered substance with a red-orange color, following the 2 reactions – diazotization and
coupling reaction. Aniline and β-naphthol was used as starting reagents. The resulting product
was purified using recrystallization and its melting point was determined. A cotton fabric was also
dyed using the synthesized Sudan-1.

Many synthetic dyes, also called diazo dyes, are coupling products of the reaction of
arenediazonium salts and highly activated aromatic substrates such as phenols and anilines.
Many of the coupling products are used as acid-base indicators and food coloring agents. For
instance, methyl red, an indicator dye, is used on laboratories to indicate the acidic content of a
chemical solution and butter yellow, which is used for margarine. Some diazo compounds are
also used as biological staining agents and textile dyes. 2

The diazonium salt reacts as an electrophile with an electron-rich coupling component, like a β-
naphthol and naphthaline derivative through an electrophilic aromatic substitution mechanism.