St. V.S.

Public Schoo
2022-2023

CHEMISTRY
INVESTIGATORY
PROJECT

SYNTHESIS OF
ASPIRIN
FROM
ACETYL
CHLORIDE

Abhay Singh
Student, St. V.S. Public School, Roll No. 02
Class XII Science

Under the Supervision of

Mr. Nitin Kumar
Chemistry Teacher, St. V.S. Public School
ACKNOWLEDGEMENT

Mere words won’t be able to express my gratitude and thankfulness

for the various people without whose involvement this project
couldn’t have been accomplished successfully.

I wish to express my deepest feelings of gratitude to Nitin Sir for

his erudite involvement and sustained guidance which has been
pivotal in my project work. His minute observation, precious
insights, and critical comments have indeed greatly helped shape
my ideas.
The guidance and support received from all my classmates, who
contributed to the project, was vital for the success of this project. I
am also humbly grateful to my parents for their constant support,
helpfulness, and encouragement throughout the project.

Abhay Singh


INDEX
1. AIM OF PROJECT 1
2. INTRODUCTION 2
3. THEORY 6
4. APPARATUS 7
5. SAFETY PRECAUTIONS 8
6. PROCEDURE 9
7. REPORT 11
8. PHOTOGRAPHS 13
9. CONCLUSIONS 14
10. REFERENCES 15
AIM OF
PROJECT
THE EXPERIMENT SEEKS TO SYNTHESIZE AND
PURIFY ASPIRIN FROM A REACTION OF
SALICYLIC ACID AND ACETYL CHLORIDE

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 INTRODUCTION
THE FIRST DISCOVERY

4,000 years ago: The ancient Sumerians made a surprising

discovery. If they scraped the bark off a particular kind of tree and
ate it, their pain disappeared. Little did they know that why they'd
found was destined to influence the future course of medicine.

What the Sumerians had discovered was a precursor to the

medicine known today as aspirin. Aspirin's active ingredient is found
commonly in willow trees and other wild plants, which is how it
came to infuse the medical traditions of Sumer, ancient Egypt,
ancient Greece, and other cultures.

Around 400 BC: Hippocrates, thought of as the father of modern

medicine, first recommended chewing willow bark for pain relief and
making willow leaf tea to ease the pain of childbirth.

LEARNING ABOUT ITS POTENTIAL

It took over 2,000 years for us to comprehensively investigate its

potential. In the mid-18th century, an Englishman named Edward
Stone ran five years of experiments, showing that willow bark
crushed into a powder and eaten could cure a fever. It took nearly
another 70 years for a German pharmacist, Johann Buchner, to

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finally identify and purify the substance that made all this possible, a
compound called Salicin.

By then, doctors were routinely using willow bark and other salicin-
rich plants, like the herb meadowsweet, to ease pain, fever, and
inflammation.

In 1853: A French chemist managed to chemically synthesize the

compound, creating a substance called acetylsalicylic acid.

INDUSTRIAL USAGE

In 1897: The pharmaceutical company Bayer found a new method

by chemist Felix Hoffman and began marketing the compound as a
pain reliever called aspirin.This was widely recognized as one of the
first synthetic pharmaceutical drugs.

Originally, aspirin was just Bayer's brand name:

A for acetyl, and spir for meadowsweet, whose botanical name is

Spiraea ulmaria.

Soon, aspirin became synonymous with acetylsalicylic acid.

As its influence grew, aspirin was found to ease not just pain, but
also many inflammation-related problems, like rheumatoid arthritis,
pericarditis, which enflames the fluid-filled sack around the heart,
and Kawasaki disease, where blood vessels become inflamed.

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WORKING OF ASPIRIN

The analgesic drug interrupts the production of certain chemicals

called prostaglandins, which control the transmission of pain
sensations and inflammation.

DOWNFALL AND SIDE EFFECTS

Over time, research has also uncovered aspirin's risks.

Overconsumption can cause bleeding in the intestines and the
brain. It can also trigger Reye's Syndrome, a rare but often fatal
illness that affects the brain and liver in children with an infection.

In the late 20th century, aspirin's success had been overshadowed

by newer pain killers with fewer side effects, like acetaminophen
(Paracetamol) and ibuprofen.

But in the 1980s, further discoveries about aspirin's benefits revived

interest in it. In fact, the 1982 Nobel Prize winners also
demonstrated that aspirin slows production of thromboxanes,
chemicals that cause clumping of platelets, which in turn form blood
clots.

NEW DISCOVERIES

A landmark clinical trial showed that aspirin reduced heart attack

risk by 44% in participants who took the drug. Today, doctors
prescribe it to people at risk of heart attack or stroke because it cuts

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the likelihood of clots forming in the arteries that supply the heart
and brain.

Even more intriguingly, there's a growing body of research that

suggests aspirin reduces the risk of getting and dying from cancer
especially colorectal cancer. This might be due to aspirin's anti-
platelet effects. By reducing platelet activity, aspirin may decrease
the levels of a certain protein that helps cancer cells spread.These
discoveries have transformed aspirin from a mere pain reliever to a
potentially life-saving treatment.

DID YOU KNOW?

• Today, we consume about 100 billion aspirin tablets each year,
and researchers continue searching for new applications.

• Already, aspirin's versatility has transformed modern medicine,

which is astounding considering its humble beginning in a
scraping of willow bark.

5
THEORY
Aspirin is both an organic ester and an organic acid. Aspirin is a
weak monoprotic 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 hydrolyzes
forming the salicylate and acetate ions.

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

acid (molar mass of 138.1 g/mol) with acetyl chloride (molar mass
of 102.1 g/mol) in the presence of pyridine.

The Chemical Reaction is as follows:

HOC6H4COOH + CH3COCl CH3COOC6H4COOH + HCl

salicylic acetyl Aspirin hydrochloric

acid chloride (acetylsalicylic acid) acid
C7H6O3 CH3COCl C9H8O4 HCl

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 APPARATUS
CHEMICALS REQUIRED
• Salicylic Acid - 10 g
• Pyridine - 7 ml
• Acetyl Chloride - 7.5 ml
• Acetic Acid
• Conc. Hydrochloric Acid

LABORATORY EQUIPMENTS REQUIRED

• Analytical Balance
• Erlenmeyer Flask (100 ml, Conical Flask)
• Graduated Cylinder
• Dropper
• Cold Distilled Water
• Beaker
• Water Bath
• Clamp (To hold the Erlenmeyer Flask)
• Funnel
• Filter Paper
• Watch Glass
• Glass Rod
• Bunsen Burner

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SAFETY PRECAUTIONS
SAFETY APPARATUS
• Laboratory Coat
• Hand Gloves
• Safety Goggles
• Face Mask
• Vaseline( To prevent burning sensation in case of fallacies)

SAFETY MEASURES
• Salicylic Acid may irritate the skin in high concentrations. Take
appropriate care to avoid contact.
• Acetyl chloride has irritating vapours and smell. Avoid inhaling
them. Transfer acetyl chloride drop wise to the graduated cylinder.
• Handle all hot equipments with caution and never leave the
Bunsen burner flame unattended.
• The hot beakers and flasks must be handled with care and should
only be moved using tongs.
• The aspirin is not pure enough for practical use as a drug. It is
used only for investigatory purposes.
• Perform the experiment in an open laboratory. Do not attempt the
project in a closed space. Always keep wearing your mask while
performing the experiment.

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 PROCEDURE
1. Obtain a 100 mL Erlenmeyer flask from the supply area. If the
Erlenmeyer flask contains water droplets, heat it on a Bunsen
burner to remove the moisture.

2. Weigh about 10 grams of salicylic acid into the Erlenmeyer flask

using an analytical balance. Do not add lumps of salicylic acid.

3. Measure about 7.0 ml of pyridine in a graduating cylinder then

pour this into the flask with the salicylic acid. Carefully pour
pyridine from the cylinder to the flask drop-wise. Constantly
swirl the contents of the flask using glass rod gently to mix
them. The solid may not all dissolve (If lumps were taken). Do
this part in an open laboratory or near a window and keep it
away from your face.

4. Measure about 7.5 ml of acetyl chloride in a graduating cylinder

and then carefully pour this into the flask with salicylic acid drop-
wise. Constantly stir the flask while adding acetyl chloride. Due
to the exothermic nature of the reaction, the flask would become
hot at the bottom.

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5. Cool the hot flask in distil water ice bath for a few minutes. The
content of the flask would become semi-solid (Jelly like) after
cooling.

6. Set up a Bunsen burner and ring stand. Use a 250 mL beaker to

make a water bath. Clamp the Erlenmeyer flask in the water
bath. Heat the water bath to about 75°C. Maintain this
temperature for 5-15 minutes. Move the burner away from the
bath when the water gets too hot. Remove the burner when the
semi-solid has been converted to liquid again.

7. At the end of 5-15 minutes, the salicylic acid should all have
dissolved and been converted to acetylsalicylic acid. Remove
the burner, and cautiously pour the solution in a thin stream into
about 300 ml of cold distil water ice bath, stirring the mixture
meanwhile with glass rod. The acetylsalicylic acid solidifies at
once. Wait till no more crystals are formed.

8. After cooling, setup a funnel with a filter paper in it. Put this
funnel into a beaker or a flask. Now filter the mixture and collect
the solid crystal residue in a watch glass.

9. Clean and rinse the mixture with acetic acid to purify it. Take it in
a watch glass and let the excess water evaporate. Measure the
weight of aspirin formed. Collect the sample in a vial or poly zip.

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REPORT
OBSERVATION
The acetylsalicylic acid formed has the following physical properties
STATE: Crystalline Solid
COLOUR: Colour is white to very lightly pink.
TEXTURE: The texture is brittle (powder like).
SMELL: The smell is similar to that of vinegar.
WEIGHT OF ASPIRIN FORMED:

CALCULATIONS
The limiting reagent here is salicylic acid, hence yield should be
calculated from its amount taken.

Molecular Formula of Salicylic Acid: C7H6O3

Molecular Formula of Acetyl Salicylic Acid: C9H8O4

Molecular Weight of Salicylic Acid: 138 g/mol

Molecular Formula of Acetyl Salicylic Acid: 180 g/mol

Theoretical Yield:
138 g of Salicylic Acid gives 180 g of Aspirin
Therefore, 10 g of Salicylic Acid will give X g of Aspirin
X = 10 x 180 = 13.04 g
138

Percentage Yield = Practical Yield x 100 =

Theoretical Yield

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 PHOTOGRAPHS & SAMPLES

Addition of Pyridine Swirling the mixture

Addition of Acetyl Chloride

12



Heating in Water Bath Stirring for Crystallisation

Aspirin Sample

13
CONCLUSIONS
Aspirin was synthesized and the percentage yield was

found to be ____ %.

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 BIBLIOGRAPHY
• http://www.webassign.net/userimages/fgdennis@waynecc/
Lab_Aspirin_Intro.pdf
• http://www.lahc.edu/classes/chemistry/arias/Exp%205%20-
%20AspirinF11.pdf
• https://labmonk.com/synthesis-of-aspirin-from-salicylic-acid-using-
_______________________________________________________________
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• _______________________________________________________________
Project
________
• https://www.scribd.com/document/332348586/Synthesis-of-
_______________________________________________________________
Aspirin-From-Salicylic-Acid-and-Acetic-Anhydride
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• Chemistry [ NCERT BOOK ]

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