Isolation of Acetylsalicylic Acid from Aspirin Tablets

Gabrillo. Shaira L.
BS-Chemistry, University of San Carlos Talamban Campus

Abstract
Acetylsalicylic acid, common name aspirin, is a widely used drug for headaches and several
other ailments. Aspirin can be produced commercially using a process called esterification,
or treatment of salicylic acid with acetic anhydride to convert salicylic acids hydroxyl group
onto an ester group and producing aspirin. Purity of the commercially produced aspirin
should be kept in check since high dosage of salicylic acid, its common impurity, causes
adverse effects to human health. In this experiment, acetylsalicylic acid is isolated from
local aspirin tablets. Aspirin tablets were separated from the binders, and were then
subjected to recrystallization to obtain acetylsalicylic crystals. Purity and yield were
measured, which indicated the ineffectiveness of the isolation scheme used in the
experiment.
I. Introduction
Acetylsalicylic Acid, also known by
trade name Aspirin, is an acetyl derivative
of salicylic acid that is a white, crystalline,
weakly acidic substance, with melting
point 137C. Acetylsalicylic Acid is used in
analgesics,
anti-inflammatories,
antipyretics, anticoagulants and antirheumatics. It is also used as an additive
in food, animal feed, drug and cosmetic.
Large doses cause acid-base imbalance
and respiratory disturbances and can be
fatal, especially in children [1].
Aspirin decomposes rapidly in
solutions of ammonium acetate or of the
acetates,
carbonates,
citrates
or
hydroxides of the alkali metals. The
synthesis of aspirin is classified as an
esterification reaction. Salicylic acid is
treated with acetic anhydride, an acid
derivative, causing a chemical reaction
that turns salicylic acid's hydroxyl group
into an ester group (R-OH R-OCOCH3).
This process yields aspirin and acetic acid,
which is considered a by-product of this
reaction. Production of aspirin tablets
makes use of binders, or starch, to bind
together the acetylsalicylic acid so it
would remain intact as a tablet after
processing [2].
Salicylic acid is a common impurity
in aspirin. The presence of salicylic acid is
undesirable, because it causes more
irritation and stomach bleeding than
aspirin does. The FDA allows a maximum
of 0.15% salicylic acid in commercial
aspirin tablets [3]. Salicylic acid is a
phenolic phytohormone and is found in
plants [4]. Phenols, sometimes called

phenolics, are a class of chemical

compounds consisting of a hydroxyl group
(OH) bonded directly to an aromatic
hydrocarbon group [5].
FeCl3 reacts with a phenol group to
form a purple complex. Addition of FeCl 3 is
a common test for the presence of
phenols. In this experiment, acetylsalicylic
acid is extracted from a commercial
aspirin
tablet
via
filtration
and
recrystallization. This separation will be
accomplished by taking advantage of the
fact that each component (binder and
ASA) contains different functional groups
which will react differently when treated
with a specific reagent. Phenols are
differentiated from other groups, and
purity of the obtained Aspirin would be
tested by addition FeCl3 and comparison of
melting points.
II. Materials and methods
This experiment was performed in
the organic laboratory of the University of
San Carlos Talamban Campus. Aspirin
tablets used were manufactured by a local
drug manufacturer. Preliminary tests were
conducted to demonstrate which reactants
reacts with which reagents. In extracting
acetylsalicylic acid, aspirin tablets were
soaked in alcohol to solvate them.
Precipitate was filtered out and filtrate was
recrystallized. Purity of the acquired
compound and the product yield were
then measured out.
II.A. Preliminary Tests
Any observable changes and
indication of a reaction were recorded to

serve as a basis to the reactions that

would occur in the second part of the
experiment.
Five separate vials were prepared,
all of which containing 2 mL of distilled
water. To the first vial, a drop of 15% FeCl 3
was added, shaking it afterwards.
To the second vial, a microspatula
of acetylsalicylic acid was added, shaking
it afterwards. One drop of 15% FeCl3 was
added to the same vial.
To the third vial, a microspatula of
benzoic acid was added. 15% FeCl 3 was
then added to the same vial.
A microspatula of starch was added
to the fourth vial, after which a drop of I 2in-KI reagent was added.
A microspatula of acetylsalicylic
acid was added to the fifth vial, after
which a drop of I2-in-KI reagent was added.
II.B. Acetylsalicylic Acid Isolation
Ten aspirin tablets were placed in a
125-mL Erlenmeyer flask, where 10-mL of
95% alcohol was added. The flask was
heated to boiling in a steam bath to
dissolve the aspirin tablets, leaving white
residue behind. After complete solvation,
the hot solution was filtered to remove the
insoluble material. The collected filtrate
was then added with 50-mL cold water to
allow acetylsalicylic acid to recrystallize.
Recrystallization took place under room
temperature for the first 10 minutes
before it was transferred in an ice bath for
five minutes. To the white residue in the
filter paper, 2-mL of distilled water was
added. The filtrate was collected and was
treated with a drop of I2-in-KI reagent.
II.C. Purity Determination and Product
Yield
Acetylsalicylic acid was collected
by suction filtration using a Bchner
funnel. The crystals and the uncrystallised
acetylsalicylic acid were placed in a
Bchner funnel and were washed with a
little cold water. The filtrate was treated
with a drop of FeCl3 to determine purity.
Obtained crystals were placed in a
pre-weighed container and were allowed
to dry. After drying, weight of the obtained
crystals was measured out and percent
yield was calculated. Using a small
amount of the crystals, melting point

range of the
determined.

obtained

crystals

was

III. Results and Discussions

Results of the preliminary tests
conducted were as shown in the table
below:
Table 1. Observation on vials after addition of
reagents

Vial 1
Vial 2
Vial 3
Vial 4
Vial 5

Colorless solution,
observed
Color change from
purple
Colorless solution,
observed
Color change from
blue-black
Color change from
yellow

no

change

colorless to
no

change

colorless to
colorless to

FeCl3 does not react with water so

no color change was observed in vial 1 of
the preliminary test. FeCl3, however,
reacts with a phenolic compound to
produce a purple complex seen in vial 2.
Since acetylsalicylic acid sample used was
impure, or presence of salicylic acid
lingers in the aspirin sample, a reaction
occurred. The said reaction and the
general reaction between a phenol and
FeCl3 are illustrated in figures 1 and 2
below, respectively:
3C6H5OH + FeCl3

(C6H5O)3Fe + 3HCl

Figure 1. Reaction between salicylic acid and FeCl3

Figure 2. Reaction between a phenol and

FeCl3

No reaction was observed in vial 3

making it known that benzoic acid is not a
phenol. In vial 4, a color change was
observed marking presence of a reaction.
Reaction between starch and iodine in the
reagent was responsible for the blue-black
color observed. This reaction is a common
confirmatory test for the presence of

iodine of starch in a solution. In vial 5,

color changed from colorless to yellow.
This only shows water assuming the color
of the reagent, which was yellow, and
thereby showing that no reaction occurred
between acetylsalicylic acid and iodine.
This can be interpreted as the absence of
binders, or starch, in the sample of
acetylsalicylic acid used.
Aspirin is highly soluble in alcohol
due to its hydrogen bonding. After
solvation, white precipitate was observed
which was the binder, or the starch used
to bind the tablets together. The solution
was filtered to separate the acetylsalicylic
acid from the binders. Cold water was
added to the filtrate to recrystallize the
acetylsalicylic acid. Water was used as
recrystallization solvent for acetylsalicylic
acid since it has low solubility in water at
low temperatures so it is less likely to
dissolve in cold water and more likely to
recrystallize. Since the precipitate is
composed mainly of starch, it produced a
blue-black color after treatment of iodine
reagent.
After a total of fifteen minutes of
recrystallization, the contents of the
crystal container was dumped into the
Bchner funnel to subject it into suction
filtration. The filtrate, treated with FeCl 3,
displayed a purple color which meant the
obtained sample of acetylsalicylic acid is
impure or has unreacted salicylic acid
present. This notion was backed up by the
measured melting point range of the
obtained
sample
which
134-136C.
Compared to the actual melting point
range of 138-140C, the measured melting
point range was lower, indicating the
presence of impurities in the sample.
The
measurements
for
the
obtained sample and the pre-weighed
container were noted in table 2.
Table 2. Mass measurements of the sample
and container
Mass
in
grams

Filter paper
Watch glass
Filter paper + watch glass +
crystals
Crystals

1.20
42.92
45.81
1.69

Total product yield of the obtained sample

was calculated using equation 1 below:
%Yield = Collected mass
x 100
Initial mass
=
1.69 x 100 = 56%
3
Total aspirin yield was 56% percent, showing that
aspirin was not fully recovered in the experiment.
VI. Conclusion
Phenols are aromatic hydrocarbons
containing
one
or
more
hydroxyl
constituents. Salicylic acid, the active
metabolite in acetylsalicylic acid, is a
phenol and reacts with FeCl3 to produce a
purple complex. As per result obtained in
the experiment, isolated acetylsalicylic
acid was not pure. Also, only a meagre
amount of aspirin was collected. From this,
it can be deduced that the separation was
not effective. Aside from impurity of the
product, most of it did not completely
separate from the binders or stuck to the
surfaces it came in contact with, leading
to poor isolation. More yield could be
acquired by using a mixture with higher
alcohol content and by washing all
surfaces aspirin came in contact to with
alcohol to wash off the aspirin.
VI. Supporting Information
Phenols (chemical structure shown in figure
3) , sometimes called phenolics, are found in the
natural world, especially in the plant kingdom. They
are a class of chemical compounds consisting of a
hydroxyl group (OH) bonded directly to an
aromatic hydrocarbon group.Although similar to
alcohols, phenols have unique properties and are not
classified as alcohols since the hydroxyl group is not
bonded to a saturated carbon atom. They have higher
acidities due to the aromatic ring's tight coupling with
the oxygen and a relatively loose bond between the
oxygen and hydrogen. The acidity of the hydroxyl
group in phenols is commonly intermediate between
that of aliphatic alcohols and carboxylic acids [5].
Figure 3. Structure of a simple phenol

VIII. References
ACETYLSALICYLIC
ACID
|
[1]
http://www.chemicalland21.com/lifescience/phar/AC
ETYLSALICYLIC%20ACID.htm
[2] Aspirin | http://en.wikipedia.org/wiki/Aspirin
[3] Synthesis of Aspirin and Oil of Wintergreen |
http://www.marin.edu/homepages/ErikDunmire/CHE

M1
Exp
men
.pdf

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eri
t7A

Salicylic
Acid
http://en.wikipedia.org/wiki/Salicylic_acid
[5] Phenols | http://en.wikipedia.org/wiki/Phenols
[4]