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Synthesis of Para-Red

The student synthesized para-red dye through electrophilic aromatic substitution. 1.82 g of para-red dye was produced from reacting 1.4 g of p-nitroaniline and 0.15 g of B-naphthol. Cotton fabric was dyed red with the para-red product. The percent yield was calculated to be 61.27%, indicating a relatively successful experiment. Maintaining the temperature of the reaction solutions in an ice bath could help maximize the para-red dye yield.

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2K views3 pages

Synthesis of Para-Red

The student synthesized para-red dye through electrophilic aromatic substitution. 1.82 g of para-red dye was produced from reacting 1.4 g of p-nitroaniline and 0.15 g of B-naphthol. Cotton fabric was dyed red with the para-red product. The percent yield was calculated to be 61.27%, indicating a relatively successful experiment. Maintaining the temperature of the reaction solutions in an ice bath could help maximize the para-red dye yield.

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Bettina Alexandra Y.

Veloso 30B
Experiment No. 8: Synthesis of Para-Red May 25, 2019

Data and Results


Picture A: Amount of Para-Red Product ​(75 ml)

Picture B: Cloth Dyed with Para-Red Product


Table A: Quantitative Data of Preparation of Para-Red Dye Experiment

Reagents Mass

p-Nitroaniline 1.4 g

B-naphthol 0.15 g

Para-Red Dye (Final Product) 78.09 (weight of 150 ml beaker and dye)
-76.27 g (weight of empty 150 ml beaker)=
1.82 g [after suction filtration]

Discussion
In the preparation of para-red through​ electrophilic aromatic substitution,​ the product dye
is ​achieved through the diazotization of aniline, the decomposition of diazonium ions and the
synthesizing of para-red through p-nitroaniline and B-naphthol.​ A piece of cotton fabric is then
dyed with para-red as seen in Picture B. ​The fabric is first dipped into an alkaline solution of
B-naphthol and then completely soaked in a p-nitrobenzenediazonium ion solution.​ During this
point of the experiment, the solution and cloth will be completely covered with para-red dye.

Since the components of the para-red dye are added consecutively so that the insoluble
components can be bound firmly to the fibers of the cotton cloth, Para-red is considered an
ingrain dye.​ It is also considered an ​azo dye​ to the unique (-N=N-) in its chemical structure.

In this experiment, ​1.82 g of Para-Red was produced.​ In order to gauge the percent yield
of this product, the theoretical yield was first calculated through determining the limiting
reagent. Then, the percent yield formula was conducted to​ yield 61.27 % signifying a relatively
successful experiment​, however product yield could have been maximized through correctly
carrying out the suction filtration and minimizing the transferring of the liquids between
glasswares in an attempt to reduce the potential of small amounts of reactants being left
throughout the course of the experiment.​ Furthermore, ​maintaining the temperature of the two
unique solutions in an ice-water bath​ can maximize the product yield of the para-red dye by
providing a smoother and more successful reaction between the two solutions. Thus, prepping
the ice-water bath and strategizing its location for easy transfer is a crucial step in order to
maximize the para-red dye product in this experiment.

Sample Calculations
Calculating for Theoretical Yield
Since p-nitroaniline is the limiting reagent, we then calculate the theoretical yield using the
amount of grams used in the beginning of the experiment: 1.4g of p-nitroaniline.
1.4 g p-nitroaniline /138.124 g/mol p-nitroaniline x 293.277 g/mol azo dye= ​2.97 g para-red
dye
Calculating for Percent Yield
Thus, 1.82/2.97 x 100 = ​61.27%

Sources
1. Lytle, J.​ Synthesis of an Azo Dye. ​[cited 25 May 2019]. Available from:
https://www.scribd.com/doc/49001508/Synthesis-of-an-Azo-Dye
2. Pubchem.ncbi.nlm.nih.gov. 2019 [cited 25 May 2019]. Available from:
https://pubchem.ncbi.nlm.nih.gov
3. Yanza A. Survey of Organic Chemistry Laboratory Manual. 1st ed. Quezon City: Ateneo
de Manila University: 2014.

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