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Synthesis of 1-phenylazo-2-naphthol
ABSTRACT
The synthesis of 1-phenylazo-2-naphthol occurs through a diazotization reaction, which forms diazonium salts, as well as a coupling
reaction that results to the formation of coupling products.[1] These two reactions produced Sudan-1, a compound that may be used
for dyeing or as coloring agents. In this experiment, phenyldiazonium chloride and -naphthol were made to react in order to form
the red azo dye. This dye was then used to color a piece of fabric through ingrain dyeing which produced an orange hue on the cloth.
The solution was then recrystallized but was not able to give off any yield, resulting in a 100% error from the theoretical value of
0.54g.
The ingrain dyeing procedure was done by placing the cotton The reaction mixtures were kept at temperatures below 5C in
fabric in a cold -naphthol solution that is submerged in an ice bath order to prevent the formation of side products such as phenol,
and was left for 2-3 minutes in order to soak up the solution. The which is of no use to its synthesis. If this reaction was done under
fabric was then removed and then patted dry in between two filter basic conditions, this would lead to the production of a pink N-
papers. The fabric was then immersed in the phenyldiazonium nitroso compound which is also not necessary for the synthesis of
chloride solution for several minutes then was rinsed well with the phenyldiazonium ion. [5]
running water.
P a g e |2
Fig. 3. Reaction mechanism of the side product N-Nitroso [5] The theoretical color of the Sudan-1 that is to be obtained was
red due to the conjugated double bonds present in its structure
In the second container, the -naphthol solution is then which allowed for the absorption of light in the visible region. The
prepared by dissolving it in NaOH, a basic solution, which forms a red color of the crystals is attributed to the presence of the OH
resonance-stabilized naphthoxide ion. If the reaction was done in auxochrome. This intensifies and enhances the color of the dye as it
an acidic medium, the -naphthol will be protonated and thus will increases the wavelength of absorption. [2]
form a carbocation. The carbocations tend to be very reactive so
they can react with the nucleophiles present in the solution which A 0% yield was obtained during the synthesis of 1-phenylazo-2-
will lead to the production of side products. [6] naphthol which may have been caused by several sources of error.
One of the most prominent errors would be the temperature at
which the experiment was done in. It was important that the
reaction mixture was done at temperatures below 5C in order to
prevent to formation of side products and in order to ensure that
the synthesis of the two components undergoes completion, but
due to the extremely hot temperature of the current season, the
Fig. 4. Reaction mechanism of the -naphthol solution [6] temperature of the reaction was harder to maintain. The purity of
the reagents used may also have played a part as the aniline used
The use of the two-pot synthesis method for the synthesis of 1- was already brown indicating its low purity.
phenylazo-2-naphthol was necessary as the two components were
prepared in different pH levels, with the phenyldiazodium chloride There are several types of dyeing, one of which is direct dyeing.
done in an acidic medium and the -naphthol solution done in a Direct dyeing is composed of the fabric and the dye and is mainly
basic medium. The phynyldiazonium chloride solution is then used for fabrics and dyes of the same IMFA. Ingrain dyeing on the
added to the -naphthol solution to start the coupling reaction other hand uses the fabric as well as the components of the dye,
which causes the diazonium ion to attack the carbon of the - also known as dye precursors. This is used when the fabric and dye
naphthol. [3] There are two possible carbons for the diazonium ion have different IMFAs so the smaller dye precursors are used so that
to attack but the attack on C1 is more favored than C3 since it is they are able to seep into the fabric. The synthesis of the dye is then
more stable as it has 7 resonance structures, with 4 that are done within the fabric itself, creating a dye molecule that is big
aromatic, while C3 has 6 with 2 that are aromatic. which will then in turn be trapped inside the fabric. The two
properties used in order to assess the quality of the dye are fastness
and levelness. Fastness consists of retention factor of the dye as
well as its resistance to fading. Levelness on the other hand refers
to the uniformity of the color that the dye imparts on the fabric. [7]
The synthesis of 1-phenylazo-2-naphthol from phenyldiazonium [9] National Institute of Standards and Technology. http://webbook
chloride and -naphthol did not give any yield leading to a 100% .nist.gov/cgi/cbook.cgi?ID=C842079&Mask=400 (Accessed April 26,
error from the theoretical value of 0.54 g. The experimental melting 2016).
point in turn could not be determined from its theoretical value of
133-134 C [9] thus the purity of the dye could not be assessed. The
filter paper used exhibited a red orange color indicating that the
Sudan-1 had been produced but due to the extremely low yield, it
could not be weighed. Despite not obtaining any 1-phenylazo-2-
naphthol, the fabric was still successfully dyed through ingrain
dyeing as it was able to produce an orange hue.
References
Appendix I
248.29 g
0.0022 mol Sudan 1 = 0.54 grams Sudan- 1
mol