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Lab 2 - Preparation of Acetaminophen

This experiment aimed to produce and purify acetaminophen through a reaction between p-aminophenol and acetic anhydride followed by recrystallization. The student obtained 7.187g of pure acetaminophen after filtration and purification, yielding an 86.2% recovery. The melting point of the pure product (172.2°C) was close to the literature value (169°C), indicating successful purification. Factors like loss during transfers and competing side reactions could lower the percent yield, while human error in temperature measurement could explain the slightly high melting point. The purpose of producing pure acetaminophen was achieved.

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6K views

Lab 2 - Preparation of Acetaminophen

This experiment aimed to produce and purify acetaminophen through a reaction between p-aminophenol and acetic anhydride followed by recrystallization. The student obtained 7.187g of pure acetaminophen after filtration and purification, yielding an 86.2% recovery. The melting point of the pure product (172.2°C) was close to the literature value (169°C), indicating successful purification. Factors like loss during transfers and competing side reactions could lower the percent yield, while human error in temperature measurement could explain the slightly high melting point. The purpose of producing pure acetaminophen was achieved.

Uploaded by

api-281862068
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© © All Rights Reserved
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Lab #2- Preparation of Acetaminophen

Lucus Turner
1131-02

PURPOSE: The purpose of this experiment is to produce and purify acetaminophen


by first reacting p-aminophenol with acetic anhydride and undergoing
recrystallization to produce a crude acetaminophen. It is than purified by a second
recrystallization using ethanol, the %yield will be calculated for pure product
produced and its purity measured by taking a melting point and comparing it to the
value listed in MSDS literature.

PROCEDURE: For a full description of this experiment, refer to Organic Chemistry


1131 Laboratory Manual. Experiment 2, Preparation of Acetaminophen, p. 12-15.
250 mL Erlenmeyer flasks were used instead of 500 mL.

REAGENTS/SAFETY: For a full list of reagents and safety refer to pre-lab for this
experiment.

REACTION STATEMENT:

OBSERVATIONS: A solution of 6.02 g of p-aminophenol and 125 mL of hydrochloric


acid was prepared and swirled in a beaker. The beaker was placed on a hotplate and
heated until the solution reached 53C. Once removed from the heat, 6 mL of acetic
anhydride was added causing the solution to have a jelly like consistency until
completely dissolving. Immediately after the anhydride dissolved, 25 mL sodium
was acetate was added, causing bubbles to form before settling. The solution was
cooled in an ice bath and stirred until a crystal was formed, the solution was
vacuum filtered and the crude acetaminophen was obtained, a small portion was

saved for lab #4. The crude crystal was put in a new clean Erlenmeyer flask with a
small amount of ethanol and heated until the crystal dissolved again. The solution
was cooled and stirred again until the solution recrystallized and vacuum filtered
once more to obtain the pure acetaminophen crystal. It was stored in a pre-weighed
vile for lab #4.

DATA:
-

Weight of pure acetaminophen obtained after subtracting the pre weighed


filter paper and vile= 7.187g.
Melting point of pure acetaminophen= 172.2C (MSDS states pure
acetaminophen has a melting point of 169C).

CALCULATIONS: To calculate the %yield of pure acetaminophen obtained the


theoretical yield must be calculated by finding the limiting reactant and then
calculating its theoretical yield if the experiment were performed with 100%
efficiency. To calculate limiting reactant:
Calculation of moles of paminophenol
Moles= mass/molar mass
n=m/MM
m= 6.02 g
MM= 109.14 g/mole
n= m/MM
n= 6.02 g/109.14 g/mole
n= 0.05516 mole

Calculation of moles of acetic


anhydride
Mass=density x volume
M=d x v
n=m/MM
v=6 mL
d= 1.082 g/mL
MM= 102.1 g/mole
m= 6 mL x 1.082 g/mL
m= 6.49 g
n= m/MM
n= 6.49g/102.1 g/mole
n= 0.06357 mole

Since p-aminophenol is the limiting reactant, it is used to calculate the theoretical


(100% efficiency) yield. Since the chemical equation of this reaction is balanced, the
moles of the resulting pure acetaminophen will have the same amount of moles as
the original reacting p-aminophenol did. Multiplying the moles by the molar mass of
acetaminophen will result in the theoretical yield.
n= 0.05516 mole
MM Acetaminophen= 151.16g/mole
m= n x MM
m= 0.05516 mole x 151.16 g/mole

m= 8.34 g

Finally, the percent yield is calculated by dividing the actual obtained weight of pure
acetaminophen by the theoretical yield and multiplying by one hundred.
%yield= actual yield/theoretical yield x 100
%yield= 7.187 g/8.34 g x 100
%yield= 86.2

DISCUSSION: Factors that could affect the percent yield- while 86.2% is a strong
yield, possibilities of errors to lose product must be examined. This could include:
loss of crystal during glass transfers and on filter paper during filtrations, competing
side reactions, recrystallization not being fully completed before filtration, and loss
of mass purifying the starting and crude material.

Factors that could affect melting point reading- one again 172.2C is a strong result
comparing to the known melting point of pure acetaminophen being 169C. As the
melting point obtained was higher than the known value, it is likely the cause was
due to human error as opposed to remaining impurities. This could include raising
the temperature too quickly on the melting point apparatus or packing the capillary
tube too full of the pure sample causing it to take slightly longer to melt.

Post Lab Questions


1) The crude product is washed with water to remove any leftover acetic acid
from the crude before purifying it.
2) The product was recrystallized in a now solvent to obtain a pure product. This
method involves dissolving the crude product in a suitable solvent (in this
case, ethanol) and then cooling the solution in an ice bath while stirring to
recrystallize the pure product. The product is than vacuum filtered with any
remaining soluble impurities filtered out of the final product with the ethanol.

CONCLUSION: The purpose of this experiment was to prepare pure


acetaminophen, and the results indicate this was a successful experiment. While
the melting point was slightly higher than the documented value, this was more
likely due to human error than it was impurities. A yield of 86.2% is also a successful
outcome of pure product as some of the pure product is always lost during lab
procedures.

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