LABORATORY REPORT CHM456

EXPERIMENT 4 : THE PREPARATION OF

ACETYLSALICYLIC ACID (ASPIRIN)

NAME : MAWADDAH BINTI AHMAD NABIL

MATRIC NO. : 2017442624

NAME of PARTNER : NURUL NATHASHA BINTI

SHAHROM

MATRIC NO. : 2017420668

DATE OF EXPERIMENT : 1 NOV 2017

OBJECTIVE
The purpose of this experiment is to prepared acetylsalicylic acid

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. The structure of salicylic acid is shown below. Although
salicylic acid was effective at reducing pain and fever, it also had some unpleasant side
effects. It is irritating to the lining of the mouth, esophagus and stomach, and can cause
haemorrhaging of the stomach lining. In 1899, the Bayer Company in Germany patented a
drug they called aspirin, which was a modification of salicylic acid.

Salicylic acid (C7H6O3) Acetylsalicylic acid (aspirin), (C9H8O4)

The acetylsalicylic acid can be prepared by the reaction between salicylic acid and
acetic anhydride. In this reaction, the hydroxyl group from benzene ring was reacted with
acetic acid to form ester functional group, so this reaction is referred as esterification
reaction. Concentrated sulphuric acid is the catalyst in this experiment which make the
reaction is complete. Crystallization process was required in this experiment because there
is some impurities such as unreacted salicylic acid and acetic anhydride presence with the
acetylsalicylic acid. So the process is needed to make sure there is impurities in the last
product. Thus the separation of acetylsalicylic acid from other materials was accomplished
and the product also washed with distilled water after the crystal was formed because the
water can decrease the soluble of acetylsalicylic acid and dissolves the left impurities.

Recrystallization process was formed to more purify the product. Methanol was used
as solvent in order to prevent the decomposition of salicylic acid because water can make
aspirin partially decompose while heating the solution. If the aspirin decompose , we cannot
get the correct result for this experiment. The impurities which is salicylic acid will
decompose from incomplete reaction with acetic anhydride, so after recrystallization, there
is no impurities in the last product.
CHEMICALS REQUIRED

2.0g salicylic acid

5.0 mL acetic anhydride
5 drops concentrated sulphuric acid
50 mL water
1% ferric chloride
Cold water

APPARATUS

125-mL Erlenmeyer flask

Glass rod
Vacuum filtration setup
Filter paper
Hot water bath/steam bath
Ice bath
Buchner funnel
Test tubes
PROCEDURE
1) 2.0g of salicylic acid was weight and placed in a 125mL Erlenmeyer flask. 5.0mL of
acetic anhydride was added followed by 5 drops of concentrated sulphuric acid.
2) The flas was swirl gently until the salicylic acid dissolved. The flask was heated on the
steam bath at about 50°C for 10 minutes. The flask was allow to cool at room
temperature, during which time the acetylcylic acid start to crystallized from the
reaction mixture.
3) Then, the flask was put in ice bath until the crystallization finish occurred. After
crystal formation is completed, 50 mL of water was added and cool the mixture in ice
bath.
4) The product was collected by vacuum filtration on Buchner funnel. A small amount
of additional cold water was used to aid in the transfer of crystals to funnel.
5) The crystals are rinse several times with small portion of cold water. It was continue
drawing air through the crystals on the Buchner funnel by suction until the crystals
are free of solvent.
6) The crystals are removed for air drying. The crude product was weight which may
contain some unreacted salicylic acid, and the percentage of yield of crude
acetylsalicylic acid was calculated.
7) Three small test tubes was obtain. 0.5 mL of water was added into each of the test
tube.
8) A small amount of salicylic acid was dissolved in first tube. A similar amount of
product was added in the second tube and the third tube was contained only solvent
that serve as the control.
9) A drop of 1% ferric chloride solution was added to each tube and the color change
after shaking was noted.
10) Formation of an iron-phenol complex with Fe(III) gives a definite color ranging from
red to violet, depending on the particular phenol present.
11) The product of first filtration was dissolved in a minimum of hot ethyl acetate (not
more than 2-3 mL) in a Erlenmeyer flask, it was gently and continuously heating the
mixture on a steam bath.
12) The mixture was cool to room temperature and its start to crystallized.
13) The product was collected by vacuum filtration using a Buchner funnel. Remaining
material was rinsed out of the flask with a few mL of cold petroleum ether.
14) The residual solvents was disposed in the waste container for non-halogenated
organic waste.
15) The melting point of the product was obtained with a completely dried sample. Pure
aspirin has a melting point at 135-136°C.
16) The product was placed in a small vial, label properly and submitted to instructor.
RESULT

Mass of salicyclic acid 2.0246 g

Mass of filter paper 1.3426 g
Total mass after recrystallization 2.2448 g – 1.3426 g
= 0.9022 g

C7H6O3 + C4H6O3  C9H8O4 + CH3COOH

Molar mass of salicylic acid 138.121 g/mol
Mass of salicylic acid 2.0246 g

Number of mole of salicylic acid 2.0246 g / 138 .121

= 0.01466mol

1 mol of salicyclic acid react with 1 mol of acetic anhydride to produce 1 mol of
acetylsalicylic acid
0.01466 mol of salicyclic acid react with 0.01466 mol of acetic anhydride to produce
0.01466 mol of acetylsalicylic acid

Theoretical yield of acetylsalicyclic acid 0.01466 mol x 180.157

= 2.6407 g

Percentage yield of acetylsalicyclic acid (0.9022 g / 2.6407 g) x 100%

= 32.17%

RESULT FOR FERRIC TEST

Test tube A Colorless of solution change to purple
Test tube B Colorless of solution change to violet.

Test tube C There is no change in colour which is

colourless solution.
DISCUSSION
In this experiment we are prepared acetylsalicylic acid. As we know acetylsalicylic
acid is a drug that is widely used as an antipyretic agent that is to reduce fever, as an
analgesic agent which is to reduce pain and as an anti-inflammatory. Chemically
acetylsalicylic acid is an ester. Esters are the products of the reaction of acids with alcohols.

The first part of the experiment was the preparation of Acetylsalicylic Acid (Aspirin). A
white, milky mixture was obtained when salicylic acid, acetic anhydride and phosphoric acid
(a catalyst) were mixed. This shows that the oxygen in salicylic acid attacks one of the
carbons in acetic anhydride. Heating of the mixture was done and a clear yellow liquid was
obtained. Heating was employed so that salicylic acid would melt and react with acetic
anhydride. On the other hand, water was added after heating. This is to prevent the
reaction of acetic anhydride with water at the start of the experiment, if this had happened,
no aspirin could have formed. In this manner, acetic anhydride was decomposed after the
formation of aspirin.

The second part of the experiment was recrystallization. This is the second part of the
purification process. Ethanol was used to dissolve aspirin along with the impurities such as
salicylic acid and others.

From the result the theoretical yield for this experiment is 2.6407 g while the actual
yield is 0.9022 g. The percentage yield we get is 32.17%. There is large different percentage
yield of this experiment to 100%.There maybe error occur when the temperature required
for on the step of the experiment that is 50˚C, we do not maintained the temperature so the
reaction do not completely react.

There also may occur error when we cut the filter paper, the pen ink may
contaminated our product so we need to make sure that we cut all the filter paper which
contained the ink. While we are doing experiment we should take care of some precaution.
As we know the acetic anhydride can causes severe burns and harmful to inhaled. We
should wear gloves when handling the acetic anhydride solution and handle it in the fume
board carefully.

The next experiment which is test of ferric chloride purity. From the result that we
obtained from the experiment.

Test tube A = Colourless of solution change to purple.

Test tube b = Colourless of solution change to violet.

Test tube c = There is no change in colour which is colourless solution.

Ferric chloride do not react with aspirin. It will react with salicylic acid which is used
to synthesize aspirin. In this light, adding an aqueous ferric chloride solution into a sample of
aspirin is a better way to see if there any unreacted salicylic acid which is not react. A purple
colour indicate the unreacted salicylic acid , so a purple colour should not exhibit any color
change. For test tube A and B salicylic acid was added so the ferric chloride was reacted with
the salicylic acid added while in the test tube C salicylic acid doesn’t added to the test. So
there is no impurities exists in the product of the experiment.
CONCLUSION
In conclusion of this experiment, we can conclude that how to prepare acetylsalicylic
acid (Aspirin). Acetylsalicylic acid was prepared and actual yield are obtained from the
product in the experiment which is 0.9022 g while the theoretical yield we calculated is
2.6407 g. The percentage yield is 32.17%. There are a few sources of error in this particular
experiment. One notable source of error is the amount of product wasted in transfers from
one piece of equipment to another. Spilling of product or solution is another source of error.
This could be rectified by using a greater amount of salicylic acid and acetic anhydride in the
beginning of the experiment. This experiment could also be made better by reducing the
number of transfers between containers. From the ferric chloride test, we can conclude that
there are no impurities in the product of the experiment.

REFRENCES
Loboratory Manual CHM456

www.8-synthesis-of-aspirin.pdf

www.odinity.com/characterization-of-aspirin/
QUESTION
1. What is the purpose of the concentrated sulphuric acid used in the first step?

It is used as a source of protons (H+) for used as a catalyst during the esterification of
thealcohol group from salicylic acid, with aceetic anhydride.

2. What would happen if the sulphuric acid were left out?

The reaction would be slow because sulfuric acid acts as a catalyst that speed up the
reaction.

3. If you used 5.0g of salicylic acid and excess acetic anhydride in the proceding
synthesis of aspirin, what would be the theoretical yield of acetylsalicylic acid in
moles? In grams?

Moles salicylic acid = 5.0 g 138.123 g / mol

= 0.036 mol
Ratio between salicylic acid and acetylsalicylic acid = 1:1
Mass = 0.036 x 180.157 g/mol
= 6.5 g

4. What is the equation for the decomposition reaction that can occur with aspirin?

water + acetylsalicylic acid ---> acetic acid + salicylic acid

5. Most aspirin tablets contain five grain of acetylsalicylic acid. How many miligrams is
this?
1 grain = 60 mg
5 grains = 5x60mg =300 mg

6. A student performed the reaction in this experiment using a water bath at 90°C
instead of 50°C. The final product was tested for the presence of phenols with ferric
chloride. This test was negative.

Within the salicylic acid portionof the mechanism, a polymerization reaction occur
because there was such a high temperature. The polymer that was created was an
impurity and due to this impurity the melting point of the product was lower than
expected.