Chemistry Investigatory

Preparation of aspirin

Name
Class:
Roll Number:
Date:
Session:
Teacher InCharge:
 Acknowledgement

At the outset, I Express a great sense of gratitude

towards my
guide Miss for his writing effort and guidance
which he has culminated in this project.
I am also grateful to
him for giving me an insight into the various
aspects with regards to my project work. I would
also like to thank miss.Rajeshwari (PGT Chemistry)
for her writing effort and guidance
which she has culminated in this project.
I am also grateful to her for giving me an
insight into the various aspects with
regards to my project work.
 CERTIFICATE

This is to certify that of

class XII has successfully completed the
investigatory project on the topic ‘Preparation of
aspirin’under the guidance of
during the academic year 2023-24 in the fulfillment
of chemistry practical examination conducted by the
Central Borad of Secondary Education (CBSE).

................. .................
(Examiner’s signature) (Teacher’s signature)

....................
(Principal’s signature)
 Index

Topics page no.

1. Introduction 5
2. Preparation of aspirin 6-13
3. Uses 14-17
4. Side effects 18
5. Conclusion 19
6. photogallery 20
7. Bilbliography 21
 INTRODUCTION

Aspirin is the most widely used over-the-counter

drug in the world. The average tablet contains about
325 milligrams of acetylsalicylic acid with an inert
binding material such as starch. Aspirin is used to
relieve pain, reduce inflammation, and lower fever.
Aspirin originally was derived by boiling the bark
of the white willow tree. Although the salicin in
willow bark has analgesic properties, purified
salicylic acid was bitter and irritating when taken
orally. Salicylic acid was neutralized with sodium
to produce sodium salicylate, which tasted better
but still irritated the stomach. Salicylic acid
could be modified to produce phenyl salicylate,
which was better tasting and less irritating, but
released the toxic substance phenol when
metabolized. Felix Hoffman and Arthur Eichengrün
first synthesized the active ingredient in aspirin,
acetylsalicylic acid, in 1893.
 Preparation of Aspirin

Aim:
The purpose of this experiment is to prepare
acetylsalicylic acid, a.k.a. aspirin.

Theory:
Aspirin, acetylsalicylic acid, was first synthesized
in 1893 by Felix Hofmann, a chemist for the German
firm of Bayer. This compound had the medicinal
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 hydrolyzes forming salicylate
and acetate ions. However, its additional
physiological effects and biochemical reactions are
still not thoroughly understood. Aspirin (molar mass
of 180.2 g/mol) is prepared by reacting salicylic
acid (molar mass of 138.1 g/mol) with acetic
anhydride (molar mass of 102.1g/mol). Aspirin is a
weak monoprotic acid.

Salicylic Acetic Aspirin Acetic

Acid Anhydride Acid

Acetaminophen is an amide, a compound that is a

derivative of ammonia that has been reacted with an
acidic substance, in this case, acetic acid.
Acetaminophen acts as a fever reducer and pain
reliever. It can be found in several analgesic
preparations, such as Tylenol, some of which may
contain other ingredients such as caffeine and
buffers.

p-aminophenol acetic acetaminophen acetic

 anhydride acid

Qualitatively, the purity of an aspirin or

acetaminophen 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

(a colligative property of pure substances). The
degree of lowering of the melting point depends on
the nature and the concentration of the impurities.

Procedure:
1. Obtain a 50 mL Erlenmeyer flask, a filter flask,
a Buchner funnel, a watch glass, a thermometer, a
weigh boat, and two pieces of filter paper from the
supply area. If the Erlenmeyer flask contains water
droplets, heat it on a Bunsen burner to remove the
moisture.

2. Obtain the mass of the watch glass and record it

on your data sheet.
3. Weigh about 2 grams of salicylic acid into the
Erlenmeyer flask. Do not try to weigh out exactly
2.000 grams of the chemical; your results will be
fine with +/– 0.250 grams of salicylic acid. Since
you won’t need the mass of the flask for further
work, zero the balance with the flask in the pan.
Then remove the flask from the balance and dispense
the amount of chemical you need. Do not leave the
flask on the balance pan and try to get the
salicylic acid into it, you’ll make a mess.

4. Measure about 5 mL of acetic anhydride (density

1.082 g/mL) into a graduated cylinder, then pour
this into the flask with the salicylic acid. Acetic
anhydride will be in the fume hood, with a graduated
cylinder to measure it in. Swirl the contents of the
flask gently to mix them. The solid may not all
dissolve. Add 5 drops of 85% phosphoric acid
(H3PO4). This will also be in the hood.

5. 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.
6. Heat the water bath to about 75°C. Maintain this
temperature for 15 minutes. Move the burner away
from the bath when the water gets too hot. A few
degrees of temperature fluctuation will not hurt the
reaction, but excess heat will release acetic
anhydride vapor

7. At the end of 15 minutes, the salicylic acid

should all have dissolved and been converted to
acetylsalicylic acid. Remove the burner, and
cautiously add about 2 mL of distilled water to the
flask. This will decompose any remaining acetic
anhydride. You may observe some hot acetic acid
vapor being formed in this step.

8. When the liquid has stopped giving off vapor,

remove the flask from the water bath and add 20 mL
of distilled water. If two layers form, or the
liquid is hazy, swirl the flask to obtain a clear
solution. Allow the flask to cool until you can
handle it comfortably. While the flask cools,
crystals of aspirin will probably appear. Do not
move the flask or handle it excessively. The
largest, purest crystals form slowly from a solution
that is not being stirred.

9. Once the flask has cooled until you can handle

it, cool it further in a nice bath. Again, avoid
swirling or stirring it any more than necessary.
Keep the flask in the ice bath for about 5 minutes.

10. Assemble the apparatus for suction filtration.

Place the filter paper in the Buchner funnel, wet it
with distilled water, and start the aspirator. Pour
the contents of the flask into the filter. Use your
spatula to get as much of the aspirin into the
funnel as possible

11. Draw air through the funnel for a few minutes to

dry the crystals. Use the bottom of the Erlenmeyer
flask to compress the crystals and spread them so
they cover the filter paper. Transfer the crystals
to a weigh boat.12. Rinse the small Erlenmeyer flask
well, then add 20 mL of distilled water and return
the crystals to the flask. You will have to bend the
weigh boat and use your spatula to move the
crystals. Transfer as much of the solid as you can.
12. Rinse the small Erlenmeyer flask well, then add
20 mL of distilled water and return the crystals to
the flask. You will have to bend the weigh boat and
use your spatula to move the crystals. Transfer as
much of the solid as you can.

13. Heat the contents of the flask to boiling. The

crystals should all dissolve. If they don’t, add a
few milli liters of water to dissolve them. When all
the crystals have dissolved, remove the flask from
heat and cool it in water bath (a 250 mL beaker with
tap water is fine). Do this recrystallization
quickly to avoid hydrolysis of the aspirin.

14. When the flask and its contents are cool enough
to handle, cool them further in an ice bath. Keep
the flask in ice for about 5 minutes.
15. Filter the crystals as you did in step 11.
Transfer them to the watchglass.

16. Weigh the crystals on the watch glass and

calculate your percentage yield.
17. Scrub the flasks and the Buchner funnel with
soap and water, then rinse them well, before you
return them to the supply area. Rinse the weigh
boats and discard them.
 Uses

• 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 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 circumstance. There is
some evidence that aspirin is effective at
preventing colorectal cancer, though the
mechanisms of this effect are unclear

• Pain: Uncoated aspirin tablets, consisting of

about 90% acetylsalicylic acid.

• Headache: Aspirin, either by itself or in a

combined formulation, effectively treats some
types of headaches, Fever: Like its ability to
control pain, aspirin's ability to control fever
is due to its action on the prostaglandin
system. 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. Swelling and inflammation: Aspirin is
• used as an anti-inflammatory agent for both
acute and long-term inflammation, as well as for
treatment of inflammatory diseases

• Heart attacks and stroke: Aspirin is an

effective analgesic for acute pain but is
generally considered inferior to ibuprofen for
the alleviation of pain because aspirin is more
likely to cause gastrointestinal bleeding.
Aspirin is generally ineffective for those pains
caused by muscle. As with other NSAIDs,
combinations of aspirin and caffeine provides
slightly greater pain relief than aspirin alone.
Aspirin is used in the treatment of migraine

• Aspirin is an important part of treatment of

those who have had a myocardial infraction
(heart attack).

• For a subset of people, aspirin may help prevent

heart attacks and strokes. In lower doses,
aspirin prevents the progression of
 cardiovascular disease. Frequently, aspirin is
combined with ADP receptor inhibitors to prevent
blood clots. Aspirin decomposes rapidly in
solutions of ammonium acetate or of the
acetates, carbonates, citrates, or hydroxides of
alkali metals. It is stable in dry air, but
gradually hydrolyses in contact with moisture to
acetic and salicylic acids.

• Decreases inflammation: Inflammation is a

component of plaque build-up and inflamed plaque
is more likely to cause a heart attack or
stroke. Aspirin fights the inflammation
associated with heart disease.

• Inhibits blood clots: Some prostaglandins in the

blood trigger a series of events that cause
blood platelets to clump together and form blood
clots. Thus, when aspirin inhibits
prostaglandins, it inhibits the formation of
blood clots as well.

• Reduces the risk of death: Research has shown

that regular aspirin use is associated with a
reduction in death from all causes, particularly
 among the elderly, people with heart disease,
and people who are physically unfit.

• Remove sweat stains: Make a paste using ground

aspirin and water and apply it over the yellowed
area before laundering. The salicylic acid in
aspirin is an effective cleaning agent, working
the same way that other acidic substances like
vinegar and lemon juice do.

• Soothe mosquito bites: To tame itching caused by

a mosquito bite, rub a dampened aspirin pill
over the inflamed area until discomfort
subsides.

• Keep soil fresh: To keep your garden thriving,

add one aspirin per gallon of watering water in
order to prevent fungus from growing around the
roots of fresh flowers. The treatment will also
result in longer lasting flowers once the blooms
are cut
 Aspirin Side Effects:

• Vomiting
• Stomach pain
• Heartburn
• Drowsiness
• Nausea
• Serious Side Effects of Aspirin:
• Ringing in the ears
• Loss of hearing
• Hives or rash
• Swelling of the eyes, face, lips, tongue, or
throat
• Wheezing or breathing difficulties
• Hoarseness
• Fast heartbeat or fast breathing
• Cold, clammy skin
• Bloody vomit or vomit that looks like coffee
grounds
• Bright red blood in stools or black or tarry
stools
 Conclusion

The theory of this experiment was that

acetylsalicylic acid, also known as aspirin, can be
synthesized from salicylic acid, acetic anhydride,
and phosphoric acid. Esters are formed through
Fischer esterification. The information from the
data acquired from this experiment reveals that the
correct product, acetylsalicylic acid, was produced.
The techniques used in this experiment include, but
are not limited to, the following: TLC; filtration;
IR spectrometry; NMR spectrometry. Chromatography,
IR spectrometry, and NMR spectrometry is commonly
used to verify the purity of medications. Filtration
is used to finish drying organic material prior to
the spectrometries.
Photo gallery
 Bibliography

• www.google.co.in
• Chemistry NCERT (XII)