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SYNTHESIS OF ASPIRIN
Laboratory Section 2
CATHRINA F. BAGARINAO
Instructor
ABSTRACT
In this experiment, crude aspirin were synthesized from the reaction of salicylic acid and acetic
anhydride under acidic conditions. Moreover, the crude aspirin was purified through
recrystallization, the necessary values were calculated, lastly the purity of the product was
measured by determining its melting point range. Aspirin was obtained by reacting salicylic acid
with acetic anhydride, a derivative of acetic acid. 2.020 g of salicylic acid yielded 2.219 g of
aspirin. The percent yield was calculated to be 84.21%. Through the process of recrystallization,
the unreacted acetic anhydride and salicylic acid that was still present in the solution were isolated
from the aspirin, which yielded to a purified aspirin product. Through melting point
determination, it was confirmed that the recrystallized aspirin is indeed purer than the crude
aspirin. The purified aspirin has narrow melting point range (150 - 155 oC), and is closer to the
theoretical value (135 oC).
INTRODUCTION
METHODOLOGY
A. Synthesis of Aspirin
In this experiment, 2.020 g of salicylic acid was placed in an Erlenmeyer flask. It was
made sure that the flask was totally dry to avoid any traces of water affecting the synthesis
process. Conducted in the fume hood, 5 ml of acetic anhydride was measured in a dry 10 ml
graduated cylinder. The measured acetic anhydride was added to the salicylic acid placed in an
Erlenmeyer flask. After gently swirling the flask to mix the liquid with the solid, 5 drops of
concentrated sulfuric acid were added. For approximately 10 minutes, the flask was placed in a
hot-water bath that was already prepared. With the use of a glass rod, the mixture was stirred
gently.
The flask was removed from the water bath. With continuous swirling, 2 mL of distilled
was added a few drops at a time. A piece of crushed ice was also added. After letting the flask to
cool to room temperature, it was placed in an ice bath to allow the solution to crystallize.
A vacuum filtration set-up was prepared. A dry, pre-
weighed filter paper was placed inside the Buchner
funnel, and then moistened with distilled water.
Suction filtration was used to obtain the white
precipitate, and cold water was used to wash any
remaining crystals from the flask. The suction was
kept for several minutes to help dry the crystals. The
filter paper with aspirin on it was allowed to
C. Phenol Test
Small portions of the salicylic acid, crude aspirin, and pure aspirin were placed in three
separate test tubes. Then, the three samples were dissolved with ethanol. After that, two drops of
FeCl3 was added into the solutions and finally, the appearance of purple color in the three
solutions was observed.
DISCUSSION
Aspirin is synthesized through the acid-catalysed reaction of salicylic acid and acetic anhydride.
Based on its structure, it can be observed that aspirin or acetylsalicylic acid has an ester
functional group. The synthesis of aspirin is an esterification reaction, although it does not follow
the conventional process. Instead of a reaction between a carboxylic acid and an alcohol, the
synthesis of aspirin involves the reaction of the alcohol group in the salicylic acid and one
acetate group in the acetic anhydride (an acid derivative). The by-product of the reaction is acetic
acid.
In the experiment, salicylic acid was allowed to react with excess acetic anhydride. 2.020
grams of salicylic acid yielded 2.219 grams of aspirin. Theoretically, that amount of salicylic
acid should have yielded 2.635 grams of aspirin. The percent yield of aspirin is 84.21%.
Although an excess amount of acetic anhydride was used, it does not guarantee that all of the
salicylic acid will react. This resulted to a lesser amount of aspirin. When starting with 2.150 g of
salicylic acid and an excess of acetic anhydride, the theoretical yield of aspirin would be 2.804
grams. Meanwhile, a 2.00 g salicylic acid will be needing 1.37 mL of acetic anhydride in order
to completely react in the reaction.
Aspirin toxicity causes respiratory alkalosis in adults due to its direct stimulatory actions
on respiratory centers in the medulla. An anion gap metabolic acidosis is the outcome of aspirin
poisoning. The krebs cycle is disrupted by salicylate, which uncouples oxidative phosphorylation
and interferes with aerobic respiration. Lactate is produced anaerobically as a result of this.
Salicylate, despite being an acid, does not contribute much to acidosis. Hypoglycemia, fever, and
fluid loss are also caused by the disruption of aerobic respiration (The University of Chicago
Pediatrics Clerkship, 2013).
Recrystallization is a purification technique that utilizes the varying solubility of a
compound at different temperatures. In this technique, a suitable solvent is first selected. A
solvent is suitable if the compound to be purified is slightly soluble in it at room temperature, but
is completely soluble at high temperatures. When a solvent has been selected, the compound is
dissolved in it at a high temperature. Then, the solution is allowed to gradually cool, and because
of the decrease in solubility, the compound solidifies again. The impurities in the compound are
left behind in the liquid part of the solution. The purified compound can then be isolated through
filtration.
The said procedure was applied to purify the crude aspirin although it was already
predetermined that a solution of ethanol and water is to be used as the solvent. Recrystallized
aspirin has a more crystalline appearance and has finer particles than crude aspirin.
The melting point of a solid substance can be used to measure its purity. As predicted by
colligative properties, the melting point of an impure substance will be lower than the melting
point of a pure substance. A substance is pure if its melting point range is narrow and is close to
the true or theoretical value. On the other hand, an impure substance will have a wide melting
point range and is far from the theoretical value.
In the experiment, the synthesized aspirin has a melting point range of 150 oC – 155 oC.
The range has a difference of 5 oC. Taking the average of the melting point range gives a value of
152.5 oC, and comparing this value to the theoretical value of 135 oC gives an error of 12.96%.
Since the melting point range is narrow and is comparatively close to the theoretical value, then
it can be said that the aspirin is relatively pure.
CONCLUSION
Aspirin was obtained by reacting salicylic acid with acetic anhydride, a derivative of
acetic acid. 2.020 g of salicylic acid yielded 2.219 g of aspirin. The percent yield was calculated
to be 84.21%. Through the process of recrystallization, the unreacted acetic anhydride and
salicylic acid that was still present in the solution were isolated from the aspirin, which yielded to a
purified aspirin product. Through melting point determination, it was confirmed that the
recrystallized aspirin is indeed purer than the crude aspirin. The purified aspirin has narrow
melting point range (150 - 155 oC), and is closer to the theoretical value (135 oC).
I. REFERENCES
Aspirin. http://www2.ohlone.edu/people/jklent/labs/101b_labs/aspirin.pdf
Brown, T.E. Lemay Jr., H.E. Bursten, B.E. Murphy, C.J. Woodward, P. (2014) Chemistry:
The Central Science, 12th edition. Philippines: Pearson Education South Asia. p. 594 –
595
Experiment 5 – Aspirin Synthesis. http://www.lahc.edu/classes/chemistry/arias/Exp
%205%20-%20AspirinF11.pdf
El-Magbri, M. (2014). The Synthesis and Analysis of Aspirin.
https://edspace.american.edu/me3609a/wp-content/uploads/sites/409/2015/10/
Synthesis-of-Aspirin.pdf
E-29 Esterification. (n/d). https://scilearn.sydney.edu.au/fychemistry/prelab/e29.pdf
Fryhle, C.B., Graham Solomons, T.W. (2011). Organic Chemistry, 10th edition. John Wiley
& Sons, Inc. p. 797 – 798
National Center for Biotechnology Information. PubChem Compund Database; CID = 2244,
https://pubchem.ncbi.nlm.nih.gov/compound/2244
National Center for Biotechnology Information. PubChem Compund Database; CID = 338,
https://pubchem.ncbi.nlm.nih.gov/compound/338
Petrucci, R.H., Harwood, W.S., Herring, G.E., Madura, J. General Chemistry: Principles &
Modern Applications, 9th Edition. Upper Saddle River, NJ: Pearson Education, Inc.,
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Smith, J.G., (2011). Organic Chemistry, 3rd edition. McGraw-Hill Companies, Inc. p 267
The University of Chicago Pediatrics Clerkship. (2013). Aspirin toxicity.
https://pedclerk.bsd.uchicago.edu/page/aspirin-poisoning
II. APPENDICES
( 138.121 )(
1 mol SA 1 mol a cetic anℎydride
V acetic anℎydride= ( mass of SA )
g 1 mol SA )( 1 mol a cetic anℎydride 1.082 g )
1 02.09 g
)( 1 mL