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SYNTHESIS OF ACETYLSALICYLIC ACID (ASPIRIN)

Adolfo, Angela Nicole G., Alcaraz Frances Jillian F., Aliman, Stephanie T., Astor, Jashmin D.,
Bauzon, Franchesca D., Cabral, Danica Rose G.

Department of Pharmacy, Faculty of Pharmacy


University of Santo Tomas

ABSTRACT

Acetylsalicylic acid, or commonly known as Aspirin, is one of the most widely used drugs
to reduce fever. It is under the drug classification of a Nonsteroidal Anti-Inflammatory Drug or
NSAID in short, Anticoagulant, Antiplatelet, Non-Opioid Analgesic, Antipyretic & Fibrinolytic
(Thrombolytic). Aspirin is formed through the combination of salicylic acid and acetic anhydride.
Both salicylic acid and acetic anhydride are mixed to create a crude product. In this experiment
Aspirin was studied of how it was produced and how the product would react to different reagents.
A commercial aspirin went through a procedure producing a synthesized aspirin, making up
different results from the reactants and products seeing the differences of the results from each.

INTRODUCTION

Acetylsalicylic Acid commonly known


as Aspirin is among the most widely used
medicine. Aspirin is also among the oldest. It
has the ability to reduce swelling, redness,
and soreness, it also acts as an analgesic to
reduce pain. The synthesis of aspirin is
acquired from salicylic acid which can be
extracted in willow trees. The boiling point of
Structural Formula of Aspirin
salicylic acid is 211C, a melting point of
(Acetylsalicylic Acid)
159C and a density of 1.44 g/mol.
Acetic anhydride is an organic
compound also known as a type of acetic
Crystallization refers to the formation
anhydride. The molecular formula for acetic
of solid crystals from a homogeneous
anhydride is C4H6O3. The synthesis of acetic
solution. It is one of the most used purifying
anhydride is quite simple as long as you
methods inorganic experiments. The
remember the term 'carboxylic acid.' A
substance to be purified is dependent to its
carboxylic acid is a functional group whose
solubility in change of temperature whether
molecular formula is defined as RCOOH.
in a hot or cold solvent. It is the main factor
Acetic anhydride is useful as a building block
that affects crystallization. The substance to
for other chemicals, such as the household
be crystallized should show the ideal
staple item vinegar. This usefulness also
solubility. It is essentially a solid-liquid
carries into the pharmaceutical industry.
separation technique and a very important
Acetic anhydride is used to make aspirin. As
one at that. Organic compounds that are
we see in the equation below, when acetic
solid in room temperature are usually purified
anhydride reacts with salicylic acid, aspirin is
by crystallization. The desired substance will
produced.
crystallize on cooling, but the impurities will
not. The objectives of experiment are the
following: (1) to explore the chemical process
in the synthesis of aspirin; (2) to be able to
calculate for the percentage yield of the
synthesized aspirin.

Structural Formula of Acetic Anhydride

METHODOLOGY

The materials needed for this experiment


are test tubes, beakers, glass rod, iron
ring/tripod, plastic wash bottle, Bunsen
burner, clamp, pipette, and watch glass. The
samples and reagents needed are salicylic
acid, acetic anhydride, conc. H2SO4,
Formation of Acetylsalicylic Acid commercial aspirin, benzoic acid, benzyl
alcohol, 2& FeCl3, iodine solution, and mL of ice-cold water to the beaker, stir
methyl alcohol. then pack the beaker in ice for 10
minutes for the aspirin to crystallize. Filter
A. Reaction of Acetic Anhydride and
the crystals using filter paper and allow to
Salicylic Acid
dry overnight, then measure the weight of
Get exactly 2.00g of salicylic acid
dried aspirin and compute for percentage
and place it in a clean, dry 20-cm test
yield.
tube. Place exactly 5.00 mL of acetic
anhydride and 5 drops of conc. H2SO4
B. Ferric Chloride Test for Salicylic Acid
into the same test tube. Stir it until the
In a 6 clean 10-cm test tubes,
salicylic acid dissolves.
place 1 mL of water each. Put a crystal of
Prepare the set-up for the
salicylic acid in the first test tube,
preparation of aspirin by bringing a 250-
powdered commercial aspirin in the
mL beaker three-fourths full of tap water
second test tube, synthesized aspirin in
to a boil; support it in a ring stand. Fill the
the third, benzoic acid in the fourth, 1 mL
wash bottle with distilled water and pack
of benzyl alcohol in the fifth, and dont
it in ice contained in a large beaker. Once
add anything in the last test tube because
the water begins to boil, turn the burner
it will serve as the control. Shake the test
off and place the test tube in a water bath;
tubes to dissolve the solid and place 2
stir well for 1 minute.
drops of 2% ferric chloride. Observe the
Let the reaction mixture to remain
color changes.
in the water bath for 20-30 minutes.
Remove the test tube from the water
C. Starch Test
bath, then cautiously pour the contents
In a three 10-cm test tubes, place
into 5 mL of water in a 150-mL beaker.
2 mL of water each. Put a small amount
Stir for 1 minute once the reaction in the
of synthesized aspirin in the first test
beaker subsides. Slowly add water until
tube, powdered commercial aspirin in the
a maximum of 40 drops until the solution
second, and dont add anything in the
becomes cloudy. If the solution returns to
third because this will serve as the
being clear, continue to add water.
control. Add 1 drop of iodine solution to
Rinse the test tube with ice-cold
each test tube. The presence of starch
water once the crystals of aspirin appear
will be indicated by blue or blue-black
in the beaker, adding the rinse to the
color change.
solution in the 150-mL beaker. Place 20
D. Preparation of Methyl Salicylate Table 1 - Reaction of Acetic Anhydride and
Place exactly 1.00g of salicylic Salicylic Acid
acid in a 20-cm test tube. Place 5 mL of
methyl alcohol and 3 drops of conc.
H2SO4 in the same test tube. Stir to
dissolve the salicylic acid in the alcohol.
Place it in a water bath for 15 minutes. A
mint aroma will indicate the presence of
methyl salicylate.

The formation of Acetylsalicylic Acid


RESULTS AND DISCUSSION is seen through the figure (Figure 1) below,
The experiment performed has 4 which went through a reaction of Salicylic
portions of experiments performed. First of is Acid and Acetic Anhydride. Also forming
the Reaction of Acetic Anhydride and Acetic Acid along with ASA or Aspirin.
Salicylic Acid which was performed/finished
the longest, wherein the second objective
would be accomplished. Then there is
theres the Ferric Chloride Test for Salicylic
Acid, Starch Test, and lastly Preparation of
Methyl Salicylate where the first objective will
take part. For the results of the first part of
the experiment the group was instructed to Figure 1. Formation of Acetylsalicylic Acid
collect 1g of Salicylic Acid. And to collect the
right or exact amount, they used a watch
glassed. Firstly, they calibrated the watch Limiting Reagent: Salicylic Acid (C7H6O3)
glass (93g) and they weighed an addition of
1g (94g) to achieve the specified amount.
After that the members collected 5mL of
Acetic Anhydride and 5 drops of conc. H2SO4
(Sulfuric Acid) with caution. Through these
they have collected the reagents they
needed to use for the experiment.
Acetic Anhydride:

Salicylic Acid:

Theoretical Yield:

Figure 2. Reaction of Acetic Anhydride


with Alicylic Acid

Percentage Yield: In the second portion of the


experiment, six chosen samples were
tested. And out of all the samples only three
had a reaction with Ferric Chloride. And
those are Salicylic Acid, Commercial Aspirin,
and Synthesized Aspirin. In conclusion that
Ferric Chloride has a rapid reaction with
In this part of the experiment, the Salicylic Acid knowing that all three consists
members witnessed the synthesize of of the reagent. And comparing from the
aspirin, wherein the percentage yield was results (seen from Table 2) Salicylic gave a
obtained from. Coming from the calculations more rapid reaction with Ferric Chloride
(seen above) the amount of acetic anhydride regarding the value or hue of the three
and salicylic acid used was calculated samples. As for the other samples they gave
through Stoichiometric calculations. There no reaction, as they maintained a colorless
we obtained the limiting reagent. And then reaction.
computed for the limiting reagent.
Table 2 Ferric Chloride Test for Salicylic In the third part of the experiment the
Acid Starch Test was performed. Wherein only
Commercial Aspirin was the only sample to
give a reaction with iodine solution, creating
a dark-green solution as seen from the
results from Table 3.

Table 3 Starch Test

As seen from Figure 3 (below) only 5


samples were immediately observed,
And as seen from Figure 4 the
because of the reason that the Synthesized
Synthesized Aspirin sample was still not
Aspirin was still being done by the other
tested. But later on gave a colorless solution
members. The experiment was completely
as a result. And as seen from the figure,
achieved in the second meeting.
Commercial Aspirin still had a light hue for
the color green. But after standing, the
sample gave a dark-green solution

Figure 4. Starch Test (without Synthesized


Figure 3. Ferric Chloride Test for Salicylic
Aspirin)
Acid (without Synthesized Aspirin)
The last portion of the experiment thus eliminated. Recrystallization removed
performed was Preparation of Methyl impurities from the formed aspirin, which
Salicylate which should give a minty aroma involved salicylic acid. To test for purity, a
to say that the experiment was a success. number of tests were conducted. One of
And from the given results, the sample did which was the ferric chloride test. A complex
give a efficacent oli-like smell or a minty with an intense violet color is formed when
aroma. But after a few moments, the smell ferric chloride is added to salicylic acid.
could not be much perceived anymore as it When ferric chloride is added to pure aspirin
was in the first moment when it was however, no reaction will occur. Another test
accomplished. is the starch test, which is used to detect the
presence of starch in the samples: prepared
aspirin, commercially available aspirin, and
control. Commercially available aspirin
should react to the iodine solution (it should
turn blue-violet or purple) because most
pharmaceutical companies add starch to
their products for aesthetic appeal.

Methyl salicylate, commonly known as oil of


wintergreen, is another ester of salicylic acid.
It is synthesized in a manner similar to
aspirin, but at a lower temperature. Similar to
aspirin, it also contains compounds that have
analgesic and antipyretic properties. It was
Figure 5. Preparation of Methyl Salicylate first isolated in 1843 by extraction from a
plant (Gaultheria spp.) which is in the mint
family, which explains the characteristic
CONCLUSION minty odor of methyl salicylate.

In the experiment, aspirin was prepared


from the chemical reaction of salicylic acid
and acetic anhydride. Upon the addition of
cold water, acetic acid was formed and was
REFERENCES

Website:

The Synthesis of Organic Aspirin. (2008,


February 28). Retrieved from
http://www.studymode.com/essays/Lab-
Report-Synthesis-Organic-Aspirin-First-
Year-Chemistry-65188753.html

Acetic anhydride. (2015, May 15). Retrieved


from
http://webbook.nist.gov/cgi/cbook.cgi?ID=C
108247&Mask=8

Books:

Bathan, G.I., Bayquen, A.V., Crisostomo,


A.B.C., Cruz, C.T., de Guia, R.M., Farrow,
F.L., Pea G.T., Sarile, A.S., Torres, P.C..
(2014). Laboratory Manual in Organic
Chemistry Revised Edition. Quezon City,
Manila: C & E Publishing, Inc.