2022-10-0182

Synthesis of Para Red Dye

Mehroz Adnan Qureshi
Contribution from Department of Chemistry, Syed Babar Ali School of Science and Engineering,
Opposite U Block, 54792, DHA
Received April 06, 2020; Email: 22100182@lums.edu.pk

ABSTRACT: Three different solutions were prepared for the synthesis of the para red dye. First
of all a solution of 2-napthol was prepared in a buffer solution of sodium hydroxide and sodium
phosphate. Meanwhile in another beaker, a solution of p-nitro aniline and aqueous HCl was
prepared by heating on a beaker with constant stirring. Then a solution of sodium nitrite was
added in it and mixed thoroughly for some time for diazotization. After some time the solution
containing the 2-napthol and the one containing diazonium salt were mixed together. The
resulting mixture was reacted and left for 30 minutes with constant stirring to proceed the
reaction. After it, the product was obtained and filtered under vacuum. The product was weighed,
and IR and UV were taken. The yield came out to be 76.4%.

INTRODUCTION Solutions of acidified p-nitro aniline, 2-

napthol and sodium nitrate are mixed to
Purpose produce a red dye. The red dye will be
The purpose of this experiment is to use lab vacuum filtrated and the dye will be
techniques to produce para red dye. obtained.

Hypothesis Azo dyes

When acidified p-nitro aniline is added in
the sodium nitrite, it forms diazonium ions.
These react with 2-napthol to give para red
Azo dyes
dye obtained after vacuum filtration.
Diazotization
contain at
NH2

NaNO2 H Cl
N
N

+ NaCl + H2O + Cl-

least one
nitrogen-
+

N N
O O O O

nitrogen
Main Reaction

N
N OH
N
+ N

double bond
OH

N
O O
N

(N=N);
O O

Predicted Outcome
Para red dye will be produced.
Setup
however
2022-10-0182

many The azo

different groups are
structures generally
are possible connected to
1
benzene and
. Monoazo naphthalene
dyes have rings, but can
only one also be
N=N double attached to
bond, while aromatic
diazo and heterocycles
triazo dyes or enolizable
contain two aliphatic
and three groups.
N=N double These side
bonds, groups are
respectively. necessary for
imparting
2022-10-0182

the color of Azo dyes

the dye, with contain at
many least one
different nitrogen-
shades and nitrogen
intensities double bond
being (N=N);
possible. however
many
Azo dyes have generally one or more N=N
double bonds present in them. They are
often connected to a benzene or a
naphthalene ring. The side chain on these
rings dictate the color the dyes will
different
impart.1These dyes have the N=N which is
extremely unstable and highly reactive.
structures
Uses
Azo dyes are used in textiles, printing, are possible
cosmetics, drugs and food processing 1
industry. They are used extensively in
laboratories in biological strains or pH
indicators. With increase in industrialization,
. Monoazo
use of azo dyes has significantly increased. 2
Almost 60-70% of the food and textile
dyes have
industries use azo dyes.
Para red dye only one
Chemically known as 1-(4-Nitrophenylazo)-
2-naphthol, has the following properties: N=N double
2022-10-0182

bond, while heterocycles

diazo and or enolizable
triazo dyes aliphatic
contain two groups.
and three These side
N=N double groups are
bonds, necessary for
respectively. imparting
The azo the color of
groups are the dye, with
generally many
connected to different
benzene and shades and
naphthalene intensities
rings, but can being
also be possible.
attached to Azo dyes
aromatic contain at
2022-10-0182

least one triazo dyes

nitrogen- contain two
nitrogen and three
double bond N=N double
(N=N); bonds,
however respectively.
many The azo
different groups are
structures generally
are possible connected to
1
benzene and
. Monoazo naphthalene
dyes have rings, but can
only one also be
N=N double attached to
bond, while aromatic
diazo and heterocycles
or enolizable
2022-10-0182

aliphatic nitrogen
groups. double bond
These side (N=N);
groups are however
necessary for many
imparting different
the color of structures
the dye, with are possible
1
many
different . Monoazo
shades and dyes have
intensities only one
being N=N double
possible. bond, while
Azo dyes diazo and
contain at triazo dyes
least one contain two
nitrogen- and three
2022-10-0182

N=N double groups are

bonds, necessary for
respectively. imparting
The azo the color of
groups are the dye, with
generally many
connected to different
benzene and shades and
naphthalene intensities
rings, but can being
also be possible.
attached to Azo dyes
aromatic contain at
heterocycles least one
or enolizable nitrogen-
aliphatic nitrogen
groups. double bond
These side (N=N);
2022-10-0182

however The azo

many groups are
different generally
structures connected to
are possible benzene and
1 naphthalene
. Monoazo rings, but can
dyes have also be
only one attached to
N=N double aromatic
bond, while heterocycles
diazo and or enolizable
triazo dyes aliphatic
contain two groups.
and three These side
N=N double groups are
bonds, necessary for
respectively. imparting
2022-10-0182

the color of structures

the dye, with are possible
1
many
different . Monoazo
shades and dyes have
intensities only one
being N=N double
possible. bond, while
Azo dyes diazo and
contain at triazo dyes
least one contain two
nitrogen- and three
nitrogen N=N double
double bond bonds,
(N=N); respectively.
however The azo
many groups are
different
2022-10-0182

generally many
connected to different
benzene and shades and
naphthalene intensities
rings, but can being
also be possible.
attached to Azo dyes
aromatic contain at
heterocycles least one
or enolizable nitrogen-
aliphatic nitrogen
groups. double bond
These side (N=N);
groups are however
necessary for many
imparting different
the color of structures
the dye, with are possible
2022-10-0182

1
naphthalene
. Monoazo rings, but can
dyes have also be
only one attached to
N=N double aromatic
bond, while heterocycles
diazo and or enolizable
triazo dyes aliphatic
contain two groups.
and three These side
N=N double groups are
bonds, necessary for
respectively. imparting
The azo the color of
groups are the dye, with
generally many
connected to different
benzene and shades and
2022-10-0182

intensities only one

being N=N double
possible. bond, while
Azo dyes diazo and
contain at triazo dyes
least one contain two
nitrogen- and three
nitrogen N=N double
double bond bonds,
(N=N); respectively.
however The azo
many groups are
different generally
structures connected to
are possible benzene and
1 naphthalene
. Monoazo rings, but can
dyes have also be
2022-10-0182

attached to Azo dyes

aromatic contain at
heterocycles least one
or enolizable nitrogen-
aliphatic nitrogen
groups. double bond
These side (N=N);
groups are however
necessary for many
imparting different
the color of structures
the dye, with are possible
1
many
different . Monoazo
shades and dyes have
intensities only one
being N=N double
possible.
2022-10-0182

bond, while heterocycles

diazo and or enolizable
triazo dyes aliphatic
contain two groups.
and three These side
N=N double groups are
bonds, necessary for
respectively. imparting
The azo the color of
groups are the dye, with
generally many
connected to different
benzene and shades and
naphthalene intensities
rings, but can being
also be possible.
attached to
Properties

Molecular weight 293.28 g/mol

aromatic State Solid
Molecular Formula C16H11N3O3
2022-10-0182

3
hydrochloride solution. The solution was
swirled for some time for diazotization.
EXPERIMENTAL SECTION Making the Reaction Mixture
The diazonium salt mixture was then poured
Chemicals and materials.
in the solution containing the alkaline 2-
2-napthol, p-nitro aniline, sodium
napthol solution. The solution was stirred
hydroxide, tri-sodium phosphate, HCl and
for some time. Few drops of HCl was added
ethanol.
in the beaker and then, a magnetic bar was
placed in the beaker and was put on a stirrer
Glassware and equipment
for roughly 30 minutes at 30 degrees
Three beakers (two 250 and one 100ml), a
centigrade.
pipette, a pipette sucker, a magnetic bar, a
hot plate, hardened filter paper, Buchner
Vacuum Filtration
funnel, an Erlenmeyer flask, (100ml) a glass
The reaction mixture was poured in a
rod, a graduated cylinder, a spatula, an ice
vacuum filtration setup. The sides of the
bath and water bath.
beaker was washed with distilled water to
get any remaining dye as a filtrate. Then the
Procedure
dye was kept in an oven for some time and
Preparation of Solutions
then was air dried to remove any
Solution 1
unnecessary water. Then it was weighed and
1g of sodium hydroxide and 9.5g of tri-
yield was calculated. UV and IR were taken.
sodium phosphate was dissolved in 200ml of
water in a beaker as a buffer solution to
RESULTS AND DISCUSSION
maintain pH of the solution. 1.4g of 2-
napthol was also dissolved. The solution Spectroscopy Result
was chilled in an ice bath for 5 minutes with Following spectrum was observed under IR
stirring intermittently. spectroscope
Solution 2
Another solution was prepared by adding IR Spectrum.
3ml of distilled water. 1.4g of p-nitro aniline
90 80
Tra n smi t t an c e [ %]
60 70
50
40

31 15.3 7
30 65.8 2

15 74.3 7
15 54.4 4
14 97.9 8
14 54.0 0

13 28.3 1

12 00.3 0
11 52.5 6
11 04.9 9
1623. 91
1591. 46

1401. 44

1258. 12
1225. 33

858. 56
834. 46

746. 31
684. 27

40 00 35 00 30 00 25 00 20 00 15 00 10 00 50 0
Wave nu mbe r cm-1

was added in it. Then, 3ml of concentrated

HCl was added in it. Heat the solution on a
hot plate until it turns clear. Cool the
solution to room temperature. Then the
solution was poured into an Erlenmeyer
flask containing ice. This will form p-nitro
aniline hydrochloride.
Solution 3
0.8g of sodium nitrite was added 3.5ml of C:\PROGRAM FILES\OPUS_65\MEAS\Haniya-Mahnoor.1 Haniya-Mahnoor ATR platinum Diamond 1 Refl 13/03/2018

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water and was poured in p-nitro aniline

2022-10-0182

So, the complementary color is visible,

Wavelength(cm-1) Groups which is orange. This is in accordance to
the observation.
1734.61 C=O

3085.82, Benzene Ring Calculations

1497.98-1591.46, The yield = Actual/Theoretical x 100 =
1.91g/2.50g x 100 = 76.4%.
684.27-858.56
Discussions
1104.99,1152.56,1200.3 C-O
0 The yield might have reduced due to
early stopping of reaction while it was
1258.12,1225.13
still occurring. Some of the compound
1328.31-1104.99 C-N might have gotten into aqueous layer
during separation. Moreover, some of
the yield might have been lost during
filtration. As it is a reversible reaction,
The Spectrum is in coherence with the there was always a chance of having
literature value showing that the correct lesser yield than expected.
compound was identified. Benzyl acetate
was obtained. This value is in The mechanism of the reaction is given
accordance with the literature value. as follows.
+ N O
NaNO2 + HCl Na+Cl- + OH
UV-Vis Spectrum
O
NH2 N N N
NH2 Proton transfer
N O +
-H2O
N N
O O O O
N HO
O O
N N

OH N N
+

N
O O
N
O O

The melting point of the final product is

not taken as para red dye decomposes at
its melting point.

Diazotization is done at low temperature

As the spectrum shows that the as higher temperature can cause the
maximum absorption occurs at 485nm. reaction of the extremely reactive
2022-10-0182

diazonium ions with the other groups or

even water.

CONCLUSIONS

Para red dye was produced by

reacting diazonium ions with 2-
napthol. The net yield was 76.4%.
The produced compound was para
nitroaniline red as indicated by the
IR spectrum and UV spectrum.

Post Lab Questions

1. p-methyl aniline is more basic then

p-nitro aniline. This will cause a
slower reaction as the reaction
involves the removal of hydrogen
from aniline. With increasing
basicity, the possibility of removing
the hydrogen will decrease.
2. It is not advised to take the melting
point of the final product as para red
dye decomposes at its melting
temperature.
3. Diazotization is proceeded at low
temperature as diazonium ions are
extremely reactive. Increased
temperature provides the kinetic
energy for the reactions and so,
diazonium ions can react with even
water to form phenol.

REFERENCES
1
Al-Rubaie, L. A.-A. R.; Mhessn, R. J. Synthesis and Characterization of Azo Dye Para Red and New Derivatives. E-
Journal of Chemistry 2012, 9 (1), 465–470.

2
Chung, K.-T. The Significance of Azo-Reduction in the Mutagenesis and Carcinogenesis of Azo Dyes. Mutation
Research/Reviews in Genetic Toxicology 1983, 114 (3), 269–281.

3
Para Red. https://pubchem.ncbi.nlm.nih.gov/compound/Para-Red (accessed Apr 6, 2020).

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