ACKNOWLEDGEMENT

I am grateful to my physics teacher, Mr.Amit Singh

for the invaluable guidance and feedback provided
throughout this project. Sir’s vast knowledge and
encouragement have been instrumental.

I would also like to thank our principal, Mrs.Rajni

nautiyal for enabling access to resources that made
this project possible.

I am deeply thankful to my parents for their

constant support and motivation. This project would
not have been achievable without them.

Name:- Kaushlendra
Saraswat

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 CERTIFICATE

This is to certify that, Kaushlendra Saraswat

of class XII of Gyan Deep Shiksha Bharati has
successfully completed his investigatory project on
“Synthesis of aspirin”.

Signature of internal Signature of external

Examiner Examiner

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 TABLE OF CONTENTS
 Acknowledgement
 Certificate
 Introduction
 Preparation of Aspirin
 Uses of Aspirin
 Side Effects
 Conclusion
 Photo gallery
 Bibliography

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 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 was better-tasting but still
irritated the stomach. Salicylic acid could
be modified to produce phenylsalicylate, 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.

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 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 the salicylate and acetate ions.

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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 102.1 g/mol).
Aspirin is a weak monoprotic 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.

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 p-Aminophenol Acetic anhydride Acetaminophen Acetic 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 fitter 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
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 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,
and 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
(H₃PO₂). 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.
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 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 an ice bath. Again, avoid
swirling or stirring it any more than necessary.
Keep the flask in the ice bath about 5 minutes.
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 10. Assemble the apparatus for a 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.
13. Heat the contents of the flask to boiling. The
crystals should all dissolve. If they don't, add a
few milli litres 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

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 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 watch glass.
16. Weigh the crystals on the watch glass, and
calculate your percent 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.

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 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 headache, 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

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 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 provide 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 the 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 reduces the overall risk of both getting
cancer and dying from cancer. Some conclude
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 the benefits are greater than the risks due to
bleeding in these at average risk.
• Aspirin decomposes rapidly in solutions of
ammonium acetate or of the acetates.
Carbonates, citrates, or hydroxides of the alkali
metals. It is stable in dry an, 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
dump together and form blood clots. Thus,
when aspirin inhibits prostaglandins, it inhibits
the formation of blood dots 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.

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 • 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, sub 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.
• Combat light cases of dandruff To remove
pesky dry skin flakes from your scalp, crush
two aspirin tablets and add them to a dab of
shampoo before washing hair as usual.
• Remove rust spots: To remove rust spots crush
an aspirin or two and wet the stained area, then
sprinkle the powder onto the rust and let it sit

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 for 10 minutes before wiping away with a damp
sponge.
• Prevent Cancer: An aspirin a day may help keep
cancer away. A recent study published in the
Annals of Oncology found the benefits of taking
aspirin to prevent some types of cancer
outweigh the harms. The researchers note the
effects of aspirin are not apparent until at least
three years after the start of use, and some
benefits are sustained for several years after
stopping daily aspirin therapy in long-term
users. If those between 50 and 65 started taking
aspirin daily for at least 10 years, there would be
a nine percent reduction in the number of
cancers, strokes, and heart attacks.

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 ASPIRIN SIDE EFFECTS
Common Side Effects of Aspirin:
 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 breaching
 Cold clammy skin
 Bloody Vomit or Vomit that looks like
coffee grounds
 Bright red blood in stools or black or tarry
stools

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 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 are
commonly used to verify the purity of medications
Filtration is used to finish drying organic material
prior to the spectrometries.

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 BIBLIOGRAPHY
• www.slideshare.net
• www.google.co.in
• Chemistry NCERT (XII)

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 PHOTO GALLERY

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