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Synthesis of Acetaminophen
Ryan Kirdahy
SCH 121 02
May 2nd, 2016
Kirdahy 2
II. Introduction:
Acetaminophen is a very common fever reducer and pain reliever. It is routinely used as an
cough, flu, colds, and treat allergies (Acetaminophen Information). Fever reducers are known as
antipyretics, and analgesics can be defined as pain relievers. Acetaminophen has both of these
properties. It is an antipyretic because it targets the center in the brain that regulates temperature.
Acetaminophen sends signals to lower the reduce the temperature of the body and in turn,
reduces a fever. Also, it reduces the pain felt by the user by decreasing the bodys sensitivity to
pain. This means a greater amount of pain must be present to overcome the effects of
acetaminophen. However, acetaminophen cannot reduce the inflammation that may be causing
the pain being experienced, it just masks the pain (List of NSAIDs). Examples where
synthesized using p-aminophenol (Figure 1) and anhydride (Figure 2) and an acid catalyst (H3O).
The product of this reaction is acetaminophen and acetic acid. Acetate would originally form, but
would protonate to form acetic acid. The objective was to perform and record the process of
synthesizing acetaminophen.
III. Results:
P-aminophenol was a white powder that was added to an Erlenmeyer flask in the amount of
1.53 g. Twenty-five milliliters of distilled water was also added to the solution. This was
followed by 20 drops of 85% phosphoric acid. The p-aminophenol did not fully dissolve in the
solution immediately, so it the liquid was clear with white particles in it. Two milliliters of acetic
anhydride were added to Erlenmeyer flask. The Erlenmeyer flask was added to an ice bath on a
hot plate and the solution dissolved and it became uniform. After 30 minutes the solution became
a milky, white precipitate. The solution was filtered and the white precipitate was the left.
Twenty milliliters of distilled water were added to the white precipitate, and the solution was
added to an ice bath for recrystallization to occur. White/off-white crystals formed. After
filtering the crystals, they were weighed. The acetaminophen crystals had a total mass of 0.37 g.
One week later the crystals were reweighed at a mass of 0.32 g. The loss of mass was water
being evaporated off. The melting point of acetaminophen is 169 C. The acetaminophen crystals
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were added to a Mel-Temp instrument to determine the melting point. The melting point was
found to be between 171-172 C which is close to the expected melting point, so it was a fairly
pure compound.
The chemical equation in Figure 4 is a balanced reaction because all of the atoms on the
the reactant side can be accounted for on the product side of the reaction. The acid catalyst is not
accounted for in the reaction because it is not changed throughout the reaction.
The starting mass of p-aminophenol (Figure 1) was 1.53 g. From that 1.53 g of p-
aminophenol, 0.37 g of acetaminophen was obtained. After one week the product had a decrease
in mass as the water evaporated, so the actual yield of the experiment was 0.32 g. To calculate
the theoretical yield for the experiment, a limiting reagent must be determined. It is necessary to
convert them both to moles of acetaminophen to compare the results. The starting mass of p-
aminophenol to moles of p-aminophenol. From there, another conversion must be made by using
1 mole acetaminophen/1 mole p-aminophenol. This step makes the reaction go from moles of p-
acetaminophen. To compare this to the other reactant another conversion must be made. This
conversion starts with 2.0 mL of acetic anhydride. The first step in the equation is to use the
density of acetic anhydride (1.08 g acetic anhydride/1 mL) to convert it to grams. The next step
is to convert from grams of acetic anhydride to moles of acetic anhydride, so the conversion 1
mole acetic anhydride/102.09 g (molar mass of acetic anhydride) is used. The final step is to
convert to moles of acetaminophen so it can be compared to the first conversion. This is done by
using 1 mole acetaminophen/1 mole acetic anhydride. The result of this equation is 0.0212 moles
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acetaminophen. Between these two, p-aminophenol is the limiting reagent. By using the limiting
reagent, the theoretical yield can then be determined. The limiting reagent (0.0140 moles
acetaminophen. The actual yield of pure acetaminophen (0.32 g acetaminophen) can then be
divided by the theoretical yield of pure acetaminophen (2.116 g acetaminophen) and multiplied
by 100 to get the percent yield. The percent yield of pure acetaminophen was 15.123%. Refer to
IV. Discussions:
During recrystallization, heat causes the solvent to dissolve because solubility increases with
an increase in temperature. This forms a supersaturated solution, which is a solution with excess
solvent. A supersaturated solution will form crystals during recrystallization, so when the solvent
is cooled the end product will be pure crystals. The crystals are pure because the impurities
should be either completely soluble or insoluble at all temperatures. This excludes the impurities
There are many reasons as to why the product in most reactions are not pure, especially with
amateur organic chemistry students. The first possibility as to why the product may not be pure
is cross-contamination. This could be a very common issue in a lab setting where several groups
are using the same equipment. If the equipment is not cleaned properly, there could be left over
residue from whatever was used previously. It is important to clean the glass wear and any other
tools thoroughly with distilled water before the experiment. It is key that it is distilled water
because normal water can cause there to be more impurities (Sources of Impurity).
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Another issue with having inexperienced students in a lab setting could be human error in
packaging. Some compounds may be very similar in color, texture, or other characteristics.
These similarities could lead to mislabeling or misuse of different compounds. This would cause
impurities for the obvious reason of either mixing the wrong compounds or creating a mixture of
the wrong compounds because they have similar external characteristics (Sources of Impurity).
The melting point can effectively be used to determine the purity of a product when the
melting point is known. Once the melting point is known, it is possible to observe the
temperature at which the compound melts. If the compounds melted at a temperature close to the
expected melting point, it can be assumed that the compound is mostly pure. A very pure
compound will have a uniform melting point with a range of less than one degree Celsius
because it is a very uniform compound. The more impurities will cause an increase in the
melting point range or completely change the melting point (Melting Point Determination).
Phenacetin can be synthesized from the reactants acetaminophen and ethyl iodide. These
reactants need hydrogen iodide and potassium carbonate as acid catalysts to help increase the
V. Conclusion:
its antipyretic and analgesics properties. It is capable of reducing fevers and also reducing pain.
It is obtained by synthesizing p-aminophenol and acetic anhydride with the presence of an acid
catalyst. This reaction yields acetaminophen and acetate, but in the presence of a base the acetate
is protonated and becomes acetic acid. In the reaction, 1.53 g of p-aminophenol was used along
with distilled water and 85% phosphoric acid. After performing the reaction and carrying out a
filtration, 0.37 g of acetaminophen product was obtain. This was left to sit for one week to dry
out any excess water. After one week, the final mass was 0.32 g of acetaminophen. After
calculating the actual yield of pure acetaminophen (0.32 g) and the theoretical yield of pure
acetaminophen (2.116 g) it was possible to calculate the percent yield of pure acetaminophen.
The percent yield of pure acetaminophen for this reaction was 15.123%. To help determine
purity it was compared to the actual melting point of acetaminophen (169 C). It was discovered
that the melting point range for the acetaminophen obtained was 171-172 C.
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Works Cited
2016. <http://www.knowyourdose.org/common-medicines/>.
"Melting Point Determiantion." Melting Point Determiantion. N.p., n.d. Web. 04 May 2016.
<http://www.inc.bme.hu/en/subjects/genchem/meltingpoint.html>.
"NSAID List: NSAIDs." NSAID List: NSAIDs. N.p., Dec. 2008. Web. 04 May 2016.
<http://www.lyberty.com/encyc/articles/nsaid.html>.
"U.S. Food and Drug Administration." Acetaminophen Information. FDA, 13 Apr. 2016. Web.
30 Apr. 2016.
<http://www.fda.gov/Drugs/DrugSafety/InformationbyDrugClass/ucm165107.htm>.