Aspirin Synthesis ACS paper
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Aspirin
Synthesis
Pauline Atillo
Department of Chemistry MCC – Maple Woods
2601 NE Barry Rd, Kansas City, MO 64156
Project under the supervision of Professor David Kwon
November 13, 2023
Abstract
One of the most widely used pain relievers on the market today is aspirin. In this
experiment, aspirin will be synthesized using salicylic acid and acetic anhydride with a catalyst
of phosphoric acid to initiate its reaction. By following the procedure, this experiment yielded
70% of the expected weight. Purity was also tested in this experiment using the melting point test
and titration. The melting point of the aspirin in this experiment is 137 degrees Celsius, when the
expected pure aspirin must be 135 degrees Celsius, according to ACS. Lastly, by doing the
titration, the purity of aspirin in this experiment is 85%.
Introduction
Aspirin is an effective analgesic (pain reliever), antipyretic (fever reducer) and anti-
inflammatory agent and is one of the most widely used non-prescription drugs. The use of aspirin
had its origin in the 18th century, when it was found that an extract from the bark of willow trees was useful in reducing pain and fever. The active ingredient in willow bark was later found to be salicylic acid.
1
Salicylic acid is a natural product found in the bark of the willow tree and was used by the ancient Greeks and Native Americans, among others, to counter fever and pain. However, salicylic acid is bitter and irritates the stomach. A German chemist named Felix Hoffman is credited with being the first to synthesize aspirin in 1897. Hoffman's father had severe arthritis but could not tolerate salicylic acid he was taking for pain relief. The name given for Hoffman's new compound was A-spirin. Apparently, this comes from acetylation (A-), together with Spirin, part of the name for Meadow-sweet (Spiraea ulmaria), a plant rich in salicylates. Aspirin can be made by reacting salicylic acid with acetic acid in the presence of an acid catalyst. However, this reaction is slow and has a relatively low yield. If acetic anhydride is used instead of acetic acid, the reaction is much faster and has a higher yield (since acetic anhydride is much more reactive than acetic acid).
1.
Experimental Details
Part 1: Synthesis of Aspirin
Figure 1 shows how aspirin is synthesized by adding salicylic acid and acetic anhydride and using phosphoric acid as the catalyst. The goal of this experiment is to make 10 tablets of aspirin, and a tablet of aspirin contains 325 milligrams of aspirin. The weight that was measured was not based on the calculation but only on the estimation of having a lot of excess. By using stoichiometry, it is determined that the limiting reagent is salicylic acid, and acetic anhydride will
be in excess. The first step of this experiment was weighing 3.5 grams of salicylic acid and putting it in a 125-milliliter Erlenmeyer flask, followed by putting 8 milliliters of acetic anhydride in a graduated cylinder and then to the same flask and 8 drops of phosphoric acid to catalyze the reaction.
Figure 2
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Figure 2 shows the next step in this experiment, where a beaker filled with water is heated to approximately 90 degrees Celsius. The heating device used in this experiment is a Bunsen burner. After reaching the expected temperature, the flask with the mixture was put in the
hot bath for exactly 20 minutes. After the 20-minute mark was reached, the mixture was cooled off, and after it was cooled off, 50 milliliters of deionized water were added to the mixture and swirled to be mixed properly. The mixture was then cooled in an ice bath to activate crystallization. Putting the mixture in the ice bath alone did not quicken the crystallization, so using a spatula, the flask was scrapped with it. After seeing some white substance, it is now indicated that crystallization has happened.
Figure 3
After crystallization, it is now time to separate the substance from the liquid. Furthermore, it is now determined that the substance that crystallized was aspirin, and the liquid was a mixture of acetic acid and water. To precisely extract aspirin, ordinary filtration will not be
enough, so filtration using a vacuum is needed to fully extract the liquid. Looking at Figure 3, that is how filtration was set up in this experiment. After emptying the flask with the mixture on it, a little bit of ice water was put inside the flask to pick up some residue that was not put in the vacuum filter. After filtering, results were gathered.
Part 2: Purity of the synthesized aspirin
After the aspirin has been obtained, it is not certain that the obtained substance is pure; every experiment has errors. In this experiment, the purity of aspirin was tested with two methods: melting point and titration. In testing the melting point, a melting point apparatus was used. By looking at the picture below, some samples of aspirin were put in a very small tube, and
the length of the aspirin inside the small tube must be at least 0.5cm.
Melting Point Apparatus
After getting some samples of aspirin, they will then be put into the melting point apparatus, and one person must constantly observe the aspirin inside the tube so that when the aspirin melts, the melting point will then be recorded.
The second test to determine purity is titration. By looking at the chemical structure of aspirin in Figure 1, it can be seen that aspirin has an H ion, indicating that it is acidic. In this titration, it did not matter how much base was put inside the burette; what’s important is to remember the initial and final volume so the volume delivered will be calculated. In the absence of a phenolphthalein indicator, an electric pH indicator was used and then plugged into a laptop with software that tells the pH of the liquid where the indicator was dipped. A sample of 1 gram of aspirin was put in a small Erlenmeyer flask and added to a sufficient amount of water so the indicator could tell the pH. The base used in this experiment was sodium hydroxide (NaOH). It was 0.45 grams of pure NaOH was added with 50 milliliters of deionized water to dilute it and its molarity was then calculated. There are no special steps that have been done in this titration, just the normal putting of the base into the acid until the pH indicator reaches its peak (pH is approximately 7). Then the results were recorded.
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Results
Part 1: Synthesis of Aspirin
Table 1
Molar Mass of Salicylic Acid
Molar Mass of Acetic
Anhydride
Molar Mass of Aspirin
138.12 g/mol
102.09
180.16 g/mol
Using the information obtained from Table 1, the exact mass of salicylic acid to make 10 tablets of aspirin can be calculated. The volume of acetic anhydride required to make 10 tablets of aspirin can also be calculated. Looking at the balanced chemical reaction: C
7
H
6
O
3
+ C
4
H
6
O
3
=> C
9
H
8
O
4
+ HC
2
H
3
O
2
With the given data: 1 tablet = 325 milligrams
Change mg to g: 323mg ×
1
g
1000
mg
¿
3.25g
Solving for mass of salicylic acid (C
7
H
6
O
3
):
3.25g C
9
H
8
O
4
×
1
moLC
9
H
8
O
4
180.16
GC
9
H
8
O
4
×
1
molC
7
H
6
O
3
1
molC
9
H
8
O
4
×
138.12
gC
7
H
6
O
3
1
molC
7
H
6
O
3
=
2.49
g
C
7
H
6
O
3
Solving for volume of acetic anhydride (C
4
H
6
O3) with the given density of 1.08 g/mol:
3.25g C
9
H
8
O
4
×
1
moLC
9
H
8
O
4
180.16
GC
9
H
8
O
4
×
1
molC
4
H
6
O
3
1
molC
9
H
8
O
4
×
102.09
gC
4
H
6
O
3
1
molC
4
H
6
O
3
×
1
mlC
4
H
6
O
3
1.08
gC
4
H
6
O
3
=
1.70
ml
C
4
H
6
O3
The calculated mass for salicylic acid to form 10 tablets of aspirin was 2.49
grams, however, in this experiment, 3.5 grams of salicylic acid were used, so in theory, this experiment should yield more aspirin. The yield should be more than 3.25 grams. So, by calculating using the experimental value used, the mass of aspirin can be obtained: 3.5
gC
7
H
6
O
3
×
1
molC
7
H
6
O
3
138.12
gC
7
H
6
O
3
×
1
mol Aspirin
1
molC
7
H
6
O
3
×
180.16
g Aspirin
1
mol Aspirin
=
4.6
g Aspirin
So, in theory, this experiment should collect 4.6 grams
Aspirin.
This experiment only obtained 3.23 grams of Aspirin.
In that case, a percent yield should be calculated to know how much aspirin has crystalized.
%yield
=
ExperimentalValue
TheoreticalValue
×
100%
=
3.23
g
4.6
g
×
100%
=
70.22%
≈
70%
Thereby, only 70% of aspirin were collected during this experiment.
Part 2: Purity
The recorded melting point of aspirin in this experiment is 137
℃
which is closer to the melting point of pure aspirin which is 135
℃
, however this does not tell that the aspirin in
this experiment pure.
Table 2
Mass aspirin weighted(g)
1.00 g
Final Volume (ml)
26ml
Initial Volume (ml)
5ml
Volume of NaOH delivered (ml)
21ml
Moles of NaOH delivered
0.0047 mol
Moles of aspirin
0.0047 mol
Grams of aspirin (calculated)
0.85 g
Purity
85%
Solving for Molarity of NaOH:
M
=
mol
V
¿
0.45
g NaOH
40
g
mol
NaOH
0.050
L
¿
0.225 ≈
.025
M
Solving for moles NaOH delivered:
mol NaOH
=
M ×V
=
0.23
M ×
0.02
L
=
0.0047
mol
Moles of NaOH delivered and moles of aspirin should be the same because of M1V1 = M2V2
Solving for grams of Aspirin from the calculations above:
0.0047
mol Aspirin×
180.16
g Aspirin
1
mol Aspirin
=
0.85
g
Solving for % purity:
%
purity
=
100%
−
(
1.00
g
−
0.85
g
1.00
g
×
100%
)
=
100%
−
15%
¿
85%
The aspirin synthesized in this experiment is only 85% pure.
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Discussion
Part 1: Synthesis of Aspirin
The results of this experiment show that only 70% of aspirin was collected. This indicated that multiple errors were made during the time that the experiment was done. A factor in the error that was made in this experiment was the measurement of the chemicals. It is not certain that the apparatus that was used in this experiment was effective and exact; maybe the graduated cylinder that was used to measure the acetic anhydride was not put on straight. Maybe the balance used to measure the mass of salicylic acid was in bad condition; that is one factor that may have caused an error. Incorrect measurement of the reactants might cause the products to not be as expected. Another factor contributing to this error is that there was a lot of aspirin left in the flask after it was filtered; it was left in the walls of the flask so that neither water nor a spatula could get it out, and this aspirin was stubborn to be taken from the flask. That's why there
is no choice but to leave it be. Another error is that the Erlenmeyer flask that was used in this experiment was not cleaned very well by the past users. The unclean flask might have some chemicals that may have reacted to the mixture, making the yield less than expected. Another error is that maybe the mixture was not heated or cooled enough to cause a reaction. If the solution was not heated properly, it may not have undergone dissociation and dissolution of the acetic anhydride and salicylic acid. All these errors might have caused the percent yield to decrease.
Part 2: Purity
During the melting point test, it was discovered that the melting point of the aspirin synthesized in this experiment is a bit closer to a pure aspirin, however it is still not determined how pure it is, so another purity test is done using titration.
The reason why titration was used to check the purity of the aspirin in this experiment is that assuming the aspirin is not contaminated with other acids, the titration allows it to quantitatively determine the purity of your aspirin, using the grams collected .
3.
In this experiment, the calculated purity of the aspirin was only 85%. This says that there are errors that occurred during the synthesis. One error contributing to the impurity is the same error as the collecting: uncleansed apparatus. Uncleaned or not thoroughly cleansed flask may have had left over chemicals that have mixed with the solution in the first steps of this experiment that have caused the impurity. Another one is that there might be not enough heat that
made the salicylic acid and acetic anhydride to fully diffuse resulting to some unreacted reactants, making this experiment collect errors and impurities.
Conclusions
The goal of this experiment is to synthesize aspirin and it was met and successful. The
aspirin collected in this experiment did have errors and impurities, however. The collected mass
of the experiment was 3.6 grams when the expected mass was 4.6 grams giving a percent yield
of only 70%. The purity of the aspirin collected in this experiment was only 85%, which tells that
it is not safe to conclude that this aspirin is the same as the one people take for medicine.
Overall, performing this experiment with the given errors will not give an aspirin similar as the
one people take as pain relievers.
References
(1)
Laney College. Experiment 8 -Synthesis of Aspirin
; 2012. https://laney.edu/cheli-
fossum/wp-content/uploads/sites/210/2012/01/8-Synthesis-of-Aspirin.pdf
.
(2)
Chemistry 104
. Chemistry 104: Synthesis of Aspirin
. Latech.edu. http://www.chem.latech.edu/~deddy/chem104/104Aspirin.
htm.
(3)
Titration of Synthesized Aspirin
. https://www.bellevuecollege.edu/wp-
content/uploads/sites/140/2014/06/161lab_Aspirin-purityUpdatedPSGF8-23-2016-.pdf.
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