PREFACE

It gives me immense pleasure in presenting this

project report on the topic ‘Preparation of Aspirin’.
It presents facts about the materials involved in the
preparation of Aspirin and the procedure of
preparation. It shows how Aspirin is prepared in the
laboratory and highlights the key points to be
taken care of while performing the activity.
The topic truly compelled us to learn and has
increased my understanding of the subject.
Performing the experiment has greatly enhanced
my perception of the concepts involved.
This report has been prepared in accordance with
the guidelines given by our Chemistry teacher Mr.
R Pathak. I hope that it fulfils all criteria and is up
to the mark. Utmost care has been taken to
eliminate mistakes. All suggestions and reviews are
welcome.

Taqdees Mariam
 ACKNOWLEDGEMENTS

I would like to express my deepest appreciation to

all those who provided me the possibility to
complete this report. A special gratitude I give to
our Chemistry teacher, Mr. R Pathak, whose
constant support, suggestions and encouragement
helped me to complete my project and write this
report.
Furthermore, I would like to acknowledge with
much appreciation the crucial role of Mr. R L Sahoo,
who gave us the permission to use all required
equipment and necessary materials to complete
the experiment. A special thanks goes to my group
members, who helped me and gave their valuable
suggestions. Last but not the least, many thanks
go to my parents, who have invested their full
efforts in guiding me.
I am deeply thankful to all those who have
provided me with the opportunity to perform this
activity.

Taqdees Mariam

CERTIFICATE

This is to certify that Taqdees Mariam, Roll No.

of class XII, Delhi Public School,
Vindhyanagar, has successfully completed her
Chemistry Project prescribed by the CBSE for the
session 2016-2017 with full attention and honesty
under my guidance while adhering to all the rules
and regulations.
She is a disciplined student and bears a good moral
character.
Dr. J Pandey Mr. R
Pathak
Principal
Chemistry Teacher
Delhi Public School, Delhi
Public School,
Vindhyanagar
Vindhyanagar
 INTRODUCTION

Aspirin (acetylsalicylic acid) is a compound derived

from salicylic acid. Salicylic acid is a natural
product found in the bark of the willow tree and
was used by the ancient Greeks and Native
Americans, among others, to counter inflammation,
fever and pain. However, salicylic acid is bitter and
irritates the stomach.
The German chemist Felix Hoffman is credited with
being the first to synthesize aspirin in 1897.
Friedrich Bayer patented the name Aspirin and
began marketing the product in 1899. It was a
huge success and sales grew rapidly. Bayer's
company is generally reckoned to have been the
first pharmaceutical company, and the production
of aspirin is generally accepted to have laid the
foundation of the modern pharmaceutical industry.
Aspirin is one of the most widely used medications
globally with an estimated 40,000 tonnes (50 to
120 billion pills) being consumed each year. It is on
the WHO Model List of Essential Medicines, the
most important medications needed in a basic
health system.
Aspirin is used in the treatment of a number of
conditions, including fever, pain, rheumatic fever,
and inflammatory diseases, such as rheumatoid
arthritis, pericarditis, and Kawasaki disease. Lower
doses of aspirin have also shown to reduce the risk
of death from a heart attack, or the risk of stroke in
some circumstances. There is some evidence that
aspirin is effective at preventing colorectal cancer,
though the mechanisms of this effect are unclear.
Aspirin is an effective analgesic for acute pain.
However, it is likely to cause gastrointestinal
bleeding. Although aspirin's use as an antipyretic in
adults is well-established, many medical societies
and regulatory agencies strongly advise against
using aspirin for treatment of fever in children
because of the risk of Reye's syndrome, a rare but
often fatal illness associated with the use of aspirin
or other salicylates in children during episodes of
viral or bacterial infection.
Aspirin decomposes rapidly in solutions of
ammonium acetate or the acetates, carbonates,
citrates, or hydroxides of the alkali metals. It is
stable in dry air, but gradually hydrolyses in
contact with moisture to acetic and salicylic acids.
In solution with alkalis, the hydrolysis proceeds
rapidly and the clear solutions formed may consist
entirely of acetate and salicylate.
Aspirin is a white, crystalline, weakly acidic
substance, with a melting point of 136 °C, and a
boiling point of 140 °C. Its acid dissociation
constant (pKa) is 3.5 at 25 °C. Aspirin can exhibit
polymorphism.
In 1971, British pharmacologist John Robert Vane
showed aspirin suppressed the production of
prostaglandins and thromboxanes. For this
discovery he was awarded the 1982 Nobel Prize in
Physiology or Medicine, jointly with Sune Bergström
and Bengt Ingemar Samuelsson.
The synthesis of aspirin is classified as an
esterification reaction. Salicylic acid is treated with
acetic anhydride, 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.
 CHEMICALS REQUIRED

SALICYLIC ACID:
Salicylic Acid (2-Hydroxybenzoic acid) is a
monohydroxybenzoic acid, a type of phenolic acid
and a beta hydroxy acid. It has the formula C7H6O3.
This colorless crystalline organic acid is widely
used in organic synthesis and functions as a plant
hormone. It is derived from the metabolism of
salicin. In addition to serving as an important
active metabolite of aspirin (acetylsalicylic acid), it
is best known for its use as a key ingredient in
topical anti-acne products. The salts and esters of
salicylic acid are known as salicylates.
Sodium salicylate is commercially prepared by
treating sodium phenolate (the sodium salt of
phenol) with carbon dioxide at high pressure (100
atm) and high temperature (390 K) – a method
known as the Kolbe-Schmitt reaction. Acidification
of the product with sulphuric acid gives salicylic
acid:

It can also be prepared by the hydrolysis of aspirin

(acetylsalicylic acid) or methyl salicylate (oil of
wintergreen) with a strong acid or base.
It occurs as white or colourless crystals with a
density of 1.443 g/cm3. Its melting point is 158.6 °C
and boiling point is 200 °C. It decomposes at
211 °C.

ACETIC ANHYDRIDE:
Acetic anhydride, or ethanoic anhydride, is the
chemical compound with the formula (CH3CO)2O.
Commonly abbreviated Ac2O, it is the simplest
isolable anhydride of a carboxylic acid and is
widely used as a reagent in organic synthesis. It is
a colorless liquid that smells strongly of acetic acid,
which is formed by its reaction with moisture in the
air.
Acetic anhydride was first synthesized in 1852 by
the French chemist Charles Frédéric Gerhardt by
heating potassium acetate with benzoyl chloride.
Acetic anhydride is produced by carbonylation of
methyl acetate:

CH3CO2CH3 + CO → (CH3CO)2O
It is present as a colourless liquid with a melting
point of −73.1 °C and a boiling point of 139.8 °C.
Its density is 1.082 g cm−3 .

SULPHURIC ACID:
Sulphuric acid is a highly corrosive strong mineral
acid with the molecular formula H 2SO4 and
molecular weight 98.079 g/mol. It is a pungent-
ethereal, colourless to slightly yellow viscous liquid
that is soluble in water at all concentrations.
Sometimes, it is dyed dark brown during
production to alert people to its hazards. The
historical name of this acid is oil of vitriol.
Sulphuric acid is a diprotic acid and shows different
properties depending upon its concentration. Its
corrosiveness on other materials, like metals, living
tissues or even stones, can be mainly ascribed to
its strong acidic nature and, if concentrated, strong
dehydrating and oxidizing properties. Sulphuric
acid at a high concentration can cause very serious
damage upon contact, since not only does it cause
chemical burns via hydrolysis, but also secondary
thermal burns through dehydration. It can lead to
permanent blindness if splashed onto eyes and
irreversible damage if swallowed. It is hygroscopic,
readily absorbing water vapour from the air.
Sulphuric acid has a wide range of applications
including in domestic acidic drain cleaners, as an
electrolyte in lead-acid batteries and in various
cleaning agents. It is also a central substance in
the chemical industry. Principal uses include
mineral processing, fertilizer manufacturing, oil
refining, wastewater processing, and chemical
synthesis. It is widely produced with different
methods, such as contact process, wet sulphuric
acid process and lead chamber process.
It is a colourless, clear and odourless liquid with a
melting point of 10 °C and a boiling point of 337
°C. It decomposes above 300 °C.

ETHANOL:
Ethanol is a volatile, flammable, colorless liquid
with a slight chemical odor. It is used as an
antiseptic, a solvent, a fuel, and due to its low
freezing point, the active fluid in many alcohol
thermometers. The molecule is a simple one, being
an ethyl group linked to a hydroxyl group. Its
structural formula IS CH3CH2OH, which is often
written as C2H5OH or EtOH.
It burns with a smokeless blue flame that is not
always visible in normal light.
It is a colourless liquid with a density of 0.789
g/cm3 . Its melting point is −114 °C and its boiling
point is 78.37 °C.

ICE:
Ice is water frozen into a solid state. Ice molecules
can exhibit up to sixteen different phases (packing
geometries) that depend on temperature and
pressure. When water is cooled rapidly
(quenching), up to three different types of
amorphous ice can form depending on the history
of its pressure and temperature.
It is formed at temperature equal to 0 °C or lower
at 1 atm pressure.
 EQUIPMENT

 Ring Stand
 Clamp
 Medicine Dropper
 Spatula
 Glass Stirring Rod
 2 400 ml Beakers
 150 ml Beaker
 125 ml Erlenmeyer Flask
 Watch Glass
 Buckner Funnel
 Filter Flask
 Vacuum Tubing
 Hot Plate
 Electronic Balance
 Calculator
 Fume Hood

THEORY
In this experiment, aspirin will be synthesized
utilizing a reaction very similar to the way it is
manufactured industrially. Salicylic acid acting as
an alcohol is reacted with acetic anhydride acting
as the acid in an esterification reaction to produce
an ester, acetylsalicylic acid (aspirin).
Concentrated sulfuric acid is used as a catalyst.

MECHANISM:

RECRYSTALLIZATION:
Solid compounds synthesized in the laboratory
usually contain impurities that must be separated
from the product before final confirmation tests are
performed. One of the most commonly used
techniques is recrystallization. The recrystallization
process is based on the changes in the solubility of
a compound as temperature changes. In
accordance with Le Chatelier's Principle, when the
dissolution process is endothermic (heat is
absorbed), solubility (solubility product) increases
with rising temperature.
If the sample is placed in a minimal amount of a
suitable solvent and then heated to near the
boiling point of the solvent, the sample will dissolve
completely forming a saturated solution. As the
sample is allowed to cool slowly to room
temperature, the compound becomes less soluble
(more saturated) and crystals come out of solution.
Any soluble impurities present in unsaturated
amounts will remain in solution. Thus, the
impurities can now be separated from the
compound by vacuum filtration.
Solvents used in the recrystallization process must
be matched to the compound being purified. The
attributes of a suitable solvent include:
● The solute particles are generally insoluble in
cold solvent, but soluble in hot solvent.
● The solvent should have a steep solubility vs
temperature curve for the solute.
● The boiling point of the solvent must be less
than the melting point of the solute.
● The solvent should not react with the solute.
● The solubility of an organic compound is a
function of the polarities of both the solvent and
the solute.
 PROCEDURE

1. Half-fill 400 ml beaker with tap water and heat it

on a hot plate to temperature of 45-50°C. This will
serve as a hot bath for the reaction. It is important
that the temperature of the water bath be steady
before heating the reactants.
2. Tare weight a plastic weighing tray to the
nearest 0.001 g.
3. Add approximately 2 g of Salicylic Acid and
determine its mass to the nearest 0.001 g.
4. Transfer the salicylic acid to a 125 mL
Erlenmeyer flask.
5. Take the flask to the fume hood.
6. Add approximately 5 mL of acetic anhydride
(Density – 1.08 g/mL) to a small graduated cylinder
and determine its volume to the nearest 0.01 ml.
7. Add the acetic anhydride to the flask containing
the salicylic acid and swirl.
8. Carefully add 4 drops of concentrated sulphuric
acid catalyst to the reaction mixture.
9. Swirl the mixture gently.
10. Heat the flask in the hot water bath for 10
minutes, stirring with a glass stirring rod or metal
spatula until the salicylic acid dissolves completely.
11. Prepare an ice-water bath in a 400 ml beaker
(about 50 ml tap water, 50 g ice)
12. Remove the flask from the hot water bath and
allow the reaction mixture to cool in the ice-water
bath until no more precipitation occurs.
Note: Particles of the acetylsalicylic acid (Aspirin)
product should begin to recrystallize out of solution
as the mixture cools. Swirl the mixture if
recrystallization does not start.
13. After the precipitation is complete, add 20 mL
of cold distilled water to the reaction flask in 5 mL
increments (wash off stirring rod), swirl to mix, and
again cool the mixture in the ice bath.
Vacuum Filtration I:
14. Set up the Vacuum Filtration apparatus.
a. Place a paper filter in the Buckner funnel
b. Insert Buckner funnel securely into the neck of
the filtration flask.
c. Attach vacuum tubing to flask and vacuum
source
d. Moisten filter paper with distilled water.
e. Turn the vacuum on and insure the moistened
filter paper forms a seal with the bottom of the
funnel.
15. Transfer the reaction mixture to the Buchner
funnel and continue to pull vacuum until all liquid is
transferred from the funnel to the flask.
16. Use the liquid in the filtration receiving flask to
rinse more product from the reaction flask and
continue the filtration.
17. Rinse the product in the funnel with small
increments of cold distilled water.
18. Continue to draw air through the filtration
apparatus until the crystals are relatively dry.
Recrystallization:
19. Transfer the product crystals to a 150 mL
beaker
20. Add 8 mL of ethanol.
21. Warm the beaker in the water bath until the
crystals dissolve completely.
22. Add 17 mL of distilled water.
23. Cover the beaker with a watch glass and set
aside to cool to room temperature.
24. Place the beaker in the ice-water bath to
complete recrystallization.
Vacuum Filtration II:
25. Setup the vacuum filtration apparatus again
with a new moistened filter.
26. Transfer the recrystallization mixture to the
Buckner Funnel and filter the purified product.
Note: Do not rinse the product in the funnel with
any additional alcohol.
Simply scrape the beaker with a spatula to
transfer as much of the product crystals as possible
to the Buchner Funnel.
27. Transfer the crystals to a paper towel for
drying.
28. Pat dry the crystals with a new piece of filter
paper.
29. Transfer the dried crystals to a pre-weighed
watch glass.

OBSERVATIONS

1.Melting point of Aspirin is 135°C.

2.The yield of crude aspirin is about 2.5g.
 Paste a picture
here
Regards : ali

PRECAUTIONS

1.Acetic anhydride is a corrosive liquid and quite

flammable.
2.Avoid breathing vapors and carry out all
transfers in the fume hood.
3.Concentrated sulphuric acid is also highly
corrosive and must be handled with care.
4.Avoid contact on skin or clothing. Wash with
copious amounts of water if a spill occurs.
5.Use clean and dry apparatus.
6.Water bath should be maintained at 45-50°C.
7.Recrystallization should be done properly to
obtain crude aspirin.
8.The amount of chemicals should be measured
appropriately and accurately.

CONTENTS
1.Certificate
2
2.Preface
3
3.Acknowledgements
4
4.Introduction
6
 5.Theory
9
6.Chemicals Required
12
7.Equipment
18
8.Procedure
19
9.Observations
23
10. Precautions
24
11. Bibliography
25
12. Declaration
26
 DECLARATION

I, Taqdees Mariam hereby declare that I have

completed my Chemistry Project Work with the
best of my knowledge and ability.
This project is complete in all respects for All India
Senior Secondary Certificate Examination.

Taqdees Mariam
Class: XII
Roll No.:
Delhi Public School,
Vindhyanagar