_1SB Acetaminophen Lab Report
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BHATT1
Acetaminophen Lab Report
CHM 235: Wednesday, 7:30-10:20am,
Room H 336; Hood 8
March, 31st, 2023
TA – Margaret Madsen
Arizona State University
SHREYA BHATT
BHATT 2
Abstract
Acetaminophen, also known as paracetamol, is a widely used pain reliever and fever reducer.
This lab report describes the synthesis of acetaminophen from p-aminophenol using acetic
anhydride as the acetylating agent and phosphoric acid as the catalyst. The reaction was carried
out at room temperature and the product was isolated by vacuum filtration and purified by
recrystallization. The purity of the final product was confirmed by measuring its melting point
and analyzing its IR spectrum. Melting points for crude and pure products were obtained, as well
as percent yields of 159% and 71.22%, respectively. The IR spectrum showed bond vibrations
similar to a spectrum of pure acetaminophen, which was another way of characterizing the
sample. The IR spectrum showed characteristic peaks for the acetaminophen molecule,
confirming the success of the synthesis.
Introduction
Acetaminophen, also known as paracetamol, is a widely used analgesic and antipyretic drug. It is
a widely used over-the-counter medication for the relief of pain and fever. It is classified as an
analgesic and antipyretic drug and is typically used to treat headaches, muscle aches, and fever.
The chemical name of acetaminophen is N-(4-hydroxyphenyl)acetamide and its molecular
formula is C8H9NO2. It is a derivative of p-aminophenol and is synthesized through the reaction
with acetic anhydride and a catalyst, typically phosphoric acid or sulfuric acid. The reaction is
below:-
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The synthesized product is typically a mixture of acetaminophen and unreacted p-aminophenol.
Therefore, it is necessary to purify the product through recrystallization. Recrystallization is a
common purification technique that involves dissolving the crude product in a suitable solvent
and then cooling the solution to allow the crystals to form. The crystals can then be collected
through filtration and dried to obtain a pure product.
Experimental
To synthesize acetaminophen, 0.149 g of p-aminophenol was mixed with 0.3 mL of acetic
anhydride, 0.5 ml of water
and 2 drops of phosphoric acid in a round-bottom flask.
A magnetic
stir bar was put into the mixture, and an air condenser was attached. The mixture was heated and
stirred using a heat plate and the refluxing technique until all solids were dissolved. After 15
minutes, the flask was cooled so that it’s easy to touch , and the spin vane and air condenser were
removed. The mixture was then cooled in an ice bath until crystals formed. Once the crystals
were formed, the crystals were filtered using a Hirsch funnel and rinsed with cold water. The
crystals were then weighed, crushed, and used for recrystallization, with a small sample collected
for obtaining the melting point. The remaining crystals were dissolved in a 50:50 methanol-water
solution and cooled to room temperature. The product was filtered again, and the recrystallized
product was weighed. Once, the weighing was done the crystals were crushed, and used for
obtaining the melting point and then was used for recording the IR spectrum.
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Results
Chemicals
Weight (g)
Melting Point (C)
P-aminophenol in the
beginning
0.149g
We didn’t do MP for the
beginning stage
Crude Product
0.330g
181.4-183.5 C
Pure Product
0.147g
169.8-170.9 C
Percent Recovery of the product :
(0.147)/(0.330)*100=
44.54%
Moles of p-aminophenol:
0.00136534mol
Moles of Crude product:
0.00218307mol
Moles of Recrystallized product:
0.00097246mol
Percent Yield:
( 0.00097246mol )/(0.00136534mol )*100= 71.22%
% Chemical Yield of Crude product:
(0.00218307mol )/(0.00136534mol )*100= 159%
%
Chemical Yield of Pure Product:
( 0.00097246mol )/(0.00136534mol )*100= 71.22%
The table above shows the Melting point and weights of chemicals after every stage. And, below
the table there are calculations of the % yields.
Below is the copy of my IR Spectrum.
Table with Peak Lables from IR Spectrum
Sample Peak (cm-1 )
Specific Bond VibrationFunctional Group
3325.2
N-H
Amide
3105.67
O-H
Alcohol
1648.11
C=O
Amide
1608.96
C=C
Benzene Ring
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Discussion:
Chemical synthesis involves breaking reactant bonds and forming new product bonds to create a
new structure. Refluxing was used to condense vapors and supply energy to reactions for an
extended period. Increasing the temperature produces activation energy that allows molecules to
transition, breaking old bonds and forming new ones. Crystallization and recrystallization
techniques were used to isolate and purify the new molecules. Melting point ranges were taken,
with the crude product having a range of 181.4C-183.5C and the pure product having a range of
169.8C-170.9C, fitting within the range for pure acetaminophen (168C-172C). The crude
product had a higher range due to impurities, so recrystallization was performed to purify the
sample further, resulting in a smaller range for the recrystallized product. The percent chemical
yield was calculated based on the number of moles in the crude and pure products, with a 159%
yield for the crude product and a 71.22% yield for the pure product, leading to a 44.54%
recovery of pure acetaminophen. The experiment demonstrated the importance of careful
handling and precise measurements. An IR spectrum of the recrystallized product showed peaks
at 1608.96cm-1, 1648.11cm-1, 3105.67cm-1, and 3325.2cm-1, corresponding to bond vibrations
of benzene ring, C=O, O-H, and N-H. Overall, the experiment was successful based on the
correct melting point ranges and IR spectrum. The source of error can be not drying the product
fully and weighing it whe it was heavy that’s why crude product’s % yield is high.
Conclusion
The aim of the experiment was to synthesize acetaminophen through isolation, purification, and
characterization to determine the sample's purity. The experiment was deemed successful based
on the obtained melting points and the IR spectrum. The yields for the crude and pure product, as
well as overall recovery, were not as expected because the crude product’s % yield was slightly
BHATT 6
higher than expected because of the error in the experiment. But, overall it was a successful
experiment. Chemical synthesis is a valuable technique in a laboratory as it enables the
production of a pure product from multiple reactants.
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References
Login
. (n.d.). Weblogin.asu.edu. Retrieved April 1, 2023, from
https://asu.instructure.com/courses/138989/files/58339968
Ch, N. H., & N, O. (2006).
Synthesis of Acetaminophen p -Aminophenol Acetic
anhydride Acetaminophen Acetic Acid
.
http://rene.souty.free.fr/IMG/pdf/ParacetamolProtocolFLORIDacetaminophen.
pdf
BHATT 8
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