ARMY PUBLIC SCHOOL

BIKANER

CHEMISTRY INVESTIGATORY PROJECT

SESSION – 2019-20

TOPIC – PREPERATION OF ASPIRIN

SUBMITTED TO: SUBMITTED BY:

MR. HIMANSHU SHARMA SUSHANT KUMAR

TIWARI

(PGT CHEMISTRY) CLASS : XII A

 CONTENTS
 Acknowledgement

 Certificate

 Theory

 Apparatus

 Synthesis

 Analysis

 Safety precautions

 Result

 Verification

 Bibliography
 ACKNOWLEDGEMENT

I owe my sincere gratitude to our principal for her able

guidance and encouragements had a long way in completion
of the project.

The work of this has been carried out under the supervision
and guidance of Mr.Himanshu Sharma (PGT Chemistry).

It is a herculean task for me to able to express my gratitude

adequately to my teacher’s guidance without whose critical
appreciation, encouragement and consideration attitude
completion of this project would not have been possible.

Sushant Kumar Tiwari

XII A

CERTIFICATE

This is to certify that Sushant Kumar Tiwari of class XII A

has completed the project titled PREPARATION OF
ASPIRIN under my supervision and guidance of
Mr. Himanshu Sharma (PGT Chemistry). The work done
by him is up to a satisfactory level as per CBSE needs and
has developed the file with great sincerity and efforts.

Mr. Himanshu Sharma Mrs. Neena Singh

 (PGT Chemistry)
(Principal)

THEORY

Aspirin, acetylsalicylic acid, was first synthesized in 1893

by Felix Hofmann, a chemist for the German firm of Bayer.
This compound had the medical properties of salicylic acid,
an extract of willow bark, without the unpleasant taste or the
high degree of irritation of the mucous membranes lining the
mouth, gullet and stomach.

Aspirin is both an organic ester and an organic acid. It is

used extensively in medicine as a pain killer(analgesic) and
as a fever reducing drug(antipyretic). When ingested,
acetylsalicylic acid remains intact in the acidic stomach, but
in the basic medium of the upper intestinal tract, it
hydrolyses forming the salicylate and acetate ions. However,
its additional physiological effects and biochemical reactions
are still not thoroughly understood.

Aspirin (molar mass = 180.2 g/mol) is prepared by reacting

salicylic acid (molar mass = 138.1 g/mol) with acetic
anhydride(molar mass = 102.1 g/mol). Aspirin is a weak
monoprotic acid.

Qualitatively, the purity of aspirin sample can be determined

from its melting point. The melting point of a substance is
essentially independent of atmospheric pressure, but it is
always lowered by the presence of impurities. The degree of
lowering of the melting point depends on the nature and the
concentration of the impurities.
 APPARATUS
Materials:
1. Distilled water
2. Acetic Anhydride
3. Salicylic Acid
4. Conc. Sulphuric Acid
5. 1% FeCl3
6. Ethanol
Equipment:
1. Ring Stand
2. Clamp
3. Bunsen burner
4. Water bath
5. Dropper
6. Spatula
7. Glass string rod
8. 2 beaker (400 ml)
9. 150 ml beaker
10. Flask (125 ml)
11. Watch glass
12. Funnel
13. Filter flask
14. Test tubes
15. Hot plate
16. Pan balance
SYNTHESIS OF ASPIRIN

PROCEDURE:

1. Weigh 4.0 g of salicylic acid in a 125 ml Erlenmeyer flask.

Using this quantity of salicylic acid to calculate the theoretical
yield of aspirin. Record the weigh on the report sheet.

2. Carefully add 6 ml of acetic anhydride to the flask.

3. Using extreme caution add drops of concentrated sulphuric

acid to the flask swirl gently and place the flask in beaker of
boiling water. Clamp the flask to a ring stand and heat for 20
minutes, constantly stir with glass rod until the entire solid is
completely dissolved.
4. Remove the flask from the boiling water bath and allow
cooling to room temperature. Crystallization should occur
during cooling. If the crystals do not grow, let the flask sit
undisturbed until crystals stop growing then add the 40 ml of
ice water. If crystals do not grow, slowly pour the solution into
a 250 ml beaker containing 40 ml of ice water, mix thoroughly
and place the beaker in ice water and let sit undisturbed until
crystals have grown. The water destroys any unreacted acetic
anhydride and will cause the insoluble aspirin to precipitate
out of solution.

5. Collect the crystals through filter paper by the method of

filtration.

6. Wash the crystals with two 10 ml portions of cold water

followed by one 10 ml portion of cold ethanol. Allow the
crude product to dry, and then weigh it on the pan balance.

7. Weigh a watch glass. Add the crystals and re-weigh. Calculate

the weight of crude aspirin. Determine the percent yield. Test
a small amount of this crude product for determination of its
melting point.

8. Test the freshly made product for purity. Aspirin naturally

decompose into acetic acid over time so the purity test should
be done with freshly prepared aspirin.
RECRYSTALLIZATION:

The crude aspirin needs to be further purified. The crude products

obtained from preparation of most of the organic compound are
contaminated by unreacted starting materials and substances from
side reaction.

These can be eliminated by a simple process known as

Recrystallization. The next phase of this experiment involves the
recrystallization and thus purification of crude aspirin sample.
ANALYSIS:

Determination of melting point:

 Fill a capillary melting point tube a depth of 0.2 cm with the

recrystallized aspirin.

 Place the capillary tube in the melting point apparatus.

 Determine the melting point. (For pure Aspirin it is 135oC)

 The aspirin sample should be labelled with your name, the

mass of the aspirin, the percent yield, and its melting point.
SAFETY PRECAUTIONS:
 Wear safety glasses at all times in laboratory.
Acetic anhydride is corrosive and its vapor is
irritating to the respiratory system.

 Avoid skin contact and inhalation of the vapors. In

the event of skin contact, rinse well with cold water.
If the vapors are inhaled, move to an area where
fresh air is available.

 Sulphuric acid is corrosive. Avoid skin contact. In

the event of skin contact, rinse well with cold water.

 p-aminophenol is harmful by inhalation and by

contact with the skin. In the event of skin contact,
 rinse well with cold water. If the vapors are inhaled,
move to an area where fresh air is available.

Result:

Mass of salicylic acid = 4.0 g

Moles of salicylic acid = 4.0 g/138.1 g/mol
= 0.028 mol
Volume of acetic anhydride = 5 ml
Density of acetic anhydride = 1.08 g/mol
Mass of acetic anhydride = 1.08 g/mol X 5 ml
= 5.4 g
Moles of acetic anhydride = 5.4 g / 102.1 g/mol
= 0.052 mol
Mass of Aspirin that can be theoretically produced
 = 0.028 mol X 180.1 g/mol
= 5.04 g
Actual yield
Amount of Aspirin obtained = 5.1 g

Verification:

Procedure and Observations:

Test Observations Inference

Action of blue litmus Blue litmus turns to red Aspirin is confirmed
paper as carboxylic group
reacts with blue
litmus

NaHCO3 test. Add a Brisk effervescence as Aspirin is confirmed

pinch of aspirin to an CO2 evolves when acid
aqueous NaHCO3 reacts with NaHCO3
solution.
 Ferric chloride test. Deep violet colour Aspirin was
Boil 0.5 g Aspirin with complex is obtained confirmed
10% NaOH solution until
a clear solution is
obtained. Cool and add
dil. HCl. Dissolve the
white precipitate obtained
in alcohol and then add a
few drops of Ferric
Chloride solution.

Bibliography:

 NCERT Chemistry Class XII

 Lab manual in Chemistry (S.K

Kundra)

 Wikipedia
 www.cbseportal.com

 Google