Chemistry’s

Investigatory
Project. (2021-2022)

Topic-Synthesis of
Aspirin.

-By ARMAN KESHRI (With Jayesh)

Class XII-B
 CERTIFICATE
This is to certify that the content of this project
entitled, “Synthesis of Aspirin” is the bona fide
work of ARMAN KESHRI, under the guidance of his
chemistry teacher- Sachin Saini, which fulfills all
the requirement issued by Central Board of
Secondary Education for the investigatory project
of class XII.

Signature of the Signature of the

chemistry teacher principal.
ACKNOWLEGDMENT

I would like to express my special thanks of gratitude to my

“Mr. Sachin Saini” as well as our school
chemistry teacher
principal “Mrs. Hardeep Kaur” who gave me this golden
opportunity to make this project, which helped me to gain more
knowledge about various concepts and aspects of the project.
INDEX
 Aim of the project
 Introduction
 Apparatus required
 Procedure
 Observation
 Conclusion
 Precautions
 Side effects
 Bibliography
 Aim of the
Experiment.

TO STUDY THE SYNTHESIS OF

ASPIRIN AND ITS EFFECT ON
PLANTS AND HUMANS.
INTRODUCTION
 Did you ever notice that whenever you have a headache or
fever, apart from paracetamol you must have also used Aspirin
many a times? It basically reduces the substances that causes
pain fever and inflammation.
It was first discovered by Felix Hoffman, a German chemist in
1897, while working for the Bayer Company, had modified
salicylic acid to create acetylsalicylic acid, which was
named aspirin.
Aspirin is used to reduce fever and relieve mild to moderate
pain from conditions such as muscle
aches, toothaches, common cold, and headaches. It may also
be used to reduce pain and swelling in conditions such
as arthritis.
 Aspirin is known as a salicylate and a nonsteroidal anti-
inflammatory drug (NSAID). Salicylic acid, whose name comes
from Salix, the willow family of plants, was derived from willow
bark extracts. In folk medicine, willow bark teas were used as
headache remedies and other tonics. Nowadays, salicylic acid is
administered in the form of aspirin which is less irritating to the
stomach than salicylic acid .It works by blocking a certain
natural substance in your body to reduce pain and swelling.
This effect reduces the risk of stroke and heart attack. If a
person has gone under a surgery on clogged arteries (such as
bypass surgery, carotid endarterectomy, coronary stent), doctor
direct them to use aspirin in low doses as a "blood thinner" to
prevent blood clots.

APPARATUS REQUIRED
First period Second Period Third period Fourth Period
Salicylic acid Shell Vial 125 mL Flask 3 x 50 mL test
tubes
Acetic anhydride melting point phenolphthalein ferric chloride
apparatus indicator dropper
85% phosphoric capillary tubes buret 2 x 50 mL beakers
acid
50 mL flask 0.1 M NaOH ethanol
Büchner funnel mortar and hot plate
pestle
buret clamp aspirin tablets Mortar and
pestle
stand with iron aspirin tablets
ring
wire gauze 50 mL graduated
cylinder
beaker of tap Parafilm
water
Aspirator spec 20
Burner cuvettes
distilled water Distilled water
ice bath centigram
balance
filter paper shell vial
Filter funnel
filter paper
stand with iron
ring

Procedure
Day 1 – Synthesis
Use a centigram balance to weigh a 50 mL Erlenmeyer flask.
Place about 2 g of sylicylic acid in the flask and weigh again. In
the fume hood, the instructor will transfer 5.0 mL of acetic
anhydride from a buret into the flask. Add 5 drops of 85%
phosphoric acid (catalyst) to the flask.
Clamp the flask in a beaker of tap water supported on a ring
stand over a burner flame. Stir if needed to dissolve the salicylic
acid. Heat the water to boiling, and shut off the flame. Keep the
flask in the hot water bath for 10 more minutes.
While the flask is still in the water bath, slowly add 2 mL of
distilled water to the flask to decompose any excess acetic
anhydride.
After a minute, remove the flask from the water bath and add
20 mL of distilled water. Let the flask cool to room temperature.
As the solution cools, crystals of aspirin will appear. Cool the
solution further by placing the reaction flask in an ice bath. Chill
5-10 mL of distilled water in a separate container.
Weigh a watch glass and filter paper on the centigram balance.
Set up a Büchner funnel on a vacuum flask connected to a
water aspirator. Place the filter paper in the funnel and moisten
with distilled water from a squirt bottle. Turn on the aspirator
and transfer the aspirin slurry into the funnel. Wash the crystals
with 5 mL of the cold DI water.
Transfer the filter paper and aspirin to a pre-weighed watch
glass and allow to air dry in your locker until the next lab
period.
It is safe to discard of the filtrate down the sink with water.
Day 2 – Analysis/Melting Point
Weigh the dry product to obtain the yield of the reaction.
Calculate the theoretical yield and percent yield of the reaction.
Pack a few crystals of your aspirin product in a melting point
capillary tube. Your instructor will demonstrate how to use the
melting point apparatus. Allow the temperature of the melting
point apparatus to increase 1 C per minute starting from 120
C. Measure the melting point range of the aspirin product. The
melting point range is the temperature when you first notice
the aspirin crystals melting up until the temperature when no
crystals remain.
Day 3 – Titration Analysis
Accurately weigh between 0.10-0.15 g of the aspirin product
into a 125 mL Erlenmeyer flask. Add 15 mL of 95 % ethanol and
swirl to dissolve. Add 2 drops of phenolphthalein indicator to
the flask.
Record the exact concentration of the standard 0.1 M NaOH
solution. Fill a buret with the standard NaOH solution and
record the initial volume. Titrate the sample until a faint pink
end point is reached. The pink color should last for at least 30
seconds after swirling.
Repeat the titration with 0.10-0.15 g of a crushed aspirin tablet.
You may need to use a mortar and pestle to crush the tablet.

Day 4 – Spectroscopic Analysis

Obtain three 50 mL test tubes. Mark them A, B, C with labeling
tape.
With a clean dropper, add 20 drops of a ferric chloride solution
to each tube.
Reagent A – Weigh 1.00 g of the aspirin product into a 50 mL
beaker. Add 10 mL of ethanol and gently warm the mixture on a
hot plate to dissolve. Do not use a Bunsen burner because
ethanol is flammable. Transfer 20 drops of this aspirin-ethanol
solution into tube A.
Reagent B – Weigh 1.00 g of the crushed aspirin tablet into a 50
mL beaker. Add 10 mL of ethanol and gently warm the mixture
on a hot plate to dissolve. The solution may appear cloudy due
to additives in the commercial aspirin. Filter this solution into a
shell vial and transfer 20 drops of this aspirin-ethanol solution
into tube B.
Reagent C - Transfer 20 drops of the standard 0.15% salicylic
acid solution into tube C.
Transfer 48 mL of DI water into each tube and seal the top with
parafilm. Invert the tube several times to mix the solution.
Your instructor will show you how to operate the spectrometer.
Allow the spectrometer to warm up for 10 minutes. Fill a
cuvette 2/3 full with the ferric chloride blank solution. Set the
spec 20 to a wavelength of 530 nm and zero the spectrometer
(zero absorbance) with a ferric chloride blank solution. Fill a
clean cuvette 2/3 with solution A and measure the absorbance
reading. Repeat the process for solutions B and C. Clean and
return the cuvettes once you are done with the readings so
others can take readings.
Observations
Aspirin belongs to the family of organic compounds known as esters
and is an acetyl derivative of salicylic acid. The esterification process
involves the reaction of a carboxyl group with a phenol group and
the reaction is reversible. So, according to Le Chatelier’s principle,
an excess of reactants must be used to shift the equilibrium to the
right, favouring the formation of aspirin. The overall mechanism
involved in the synthesis of aspirin from the reaction between acetic
anhydride and salicylic acid in the presence of concentrated acid
catalyst by means of curved arrow diagrams to highlight the transfer
of electrons.
Observations-2
EFFECTS OF ASPIRIN ON PLANTS

Following were the effects of Aspirin on plant “arabidopis”-

 NSAIDs exhibit striking activity in shaping Arabidopsis root

development

 NSAIDs interfere with auxin transport and endomembrane

trafficking

 NSAID treatments impair actin filament dynamics and

endosomal mobility

 NSAIDs directly target TWD1, suppressing its chaperone activity

and actin dynamics
Conclusion

Through this project, we have underlined the important aspects

regarding the synthesis of aspirin, its usage, its effects on humans-
both positive and negative effects and their effects on plants. We
have also provided an overview of the commercial synthesis of
aspirin and also given the purity of it when prepared in a laboratory.
Precautions
Wear goggles throughout this experiment. This experiment
uses salicylic acid, acetic anhydride and phosphoric acid. The
salicylic acid and aspirin may cause irritation to your skin or
eyes, but are basically not hazardous.

An excess of these chemicals can be disposed of in the sink or, if

packaged, in the trash.

If you spill some chemical, wipe it up with a wet paper towel

and throw the towel in the trash. The acetic anhydride and
sulfuric acid can cause bad burns.

Wear gloves when using these chemicals.

Excess chemicals must be disposed of in the plastic tub of

water. This will convert the acetic anhydride to vinegar and
dilute the sulfuric acid
Side effects
The most common side effects of aspirin are:
1. Stomach or gut irritation
2. Indigestion
3. Nausea
The following adverse effects are less common:
1. Worsening asthma symptoms
2. Vomiting
3. Stomach inflammation
4. Stomach bleeding
5. Bruising
Bibliography
Medical news today
Rxlist
Webmd
Research gate
Science daily
Latech
Lahc