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CHEMISTRY PROJECT

PREPARATION OF ASPIRIN

HEM SHEELA MODEL SCHOOL, DURGAPUR

NAME: SAYANDIP MONDAL

CLASS: XII

SEC: D

SESSION: 2019-20

BOARD ROLL NO:

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ACKNOWLEDGEMENT
I would like to express my special thanks
of gratitude to my teacher Sir Madan
Mohan Pitt for his guidance and
supervision, for providing necessary
information regarding the project and for
his help in completing the project. I would
also like to take the opportunity to thank
our principal Miss Anindita Home
Choudhury who gave me the golden
opportunity to do this wonderful project
on the topic preparation of Aspirin, which
also helped me in doing a lot of Research
hence enhancing my knowledge.
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CERTIFICATE
To whom it may concern:
This is to certify that Sayandip Mondal
of class 12-D
of Hem Sheela Model School, Durgapur
Session 2019-20 has completed the
Chemistry Project appertaining to
having fulfilled all requirements of this
Project.

EXTERNAL SIGNATURE

PRINCIPAL SIGNATURE SUBJECT TEACHER

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INDEX

Sl. CONTENTS Page Nos. Sign

No.
1 Introduction 05-06

2 Medicinal Uses 06-07

3 Aim 07

4 Theory 07

5 Materials Required 07-08

6 Safety Precautions 08

7 Procedure 08-09

8 Report 09-10

9 Bibliography 10
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INTRODUCTION

Aspirin, also known as acetylsalicylic acid (ASA), is a medication used to treat pain, fever,
or inflammation. Specific inflammatory conditions which aspirin is used to treat
include Kawasaki disease, pericarditis, and rheumatic fever. Aspirin given shortly after
a heart attack decreases the risk of death. Aspirin is also used long-term to help prevent
further heart attacks, ischaemic strokes, and blood clots in people at high risk. It may also
decrease the risk of certain types of cancer, particularly colorectal cancer. For pain or fever,
effects typically begin within 30 minutes. Aspirin is a non-steroidal anti-inflammatory
drug (NSAID) and works similarly to other NSAIDs but also suppresses the normal
functioning of platelets.
One common adverse effect is an upset stomach. More significant side effects
include stomach ulcers, stomach bleeding, and worsening asthma. Bleeding risk is greater
among those who are older, drink alcohol, take other NSAIDs, or are on other blood
thinners. Aspirin is not recommended in the last part of pregnancy. It is not generally
recommended in children with infections because of the risk of Reye syndrome. High doses
may result in ringing in the ears.
A precursor to aspirin found in leaves from the willow tree has been used for its health
effects for at least 2,400 years. In 1853, chemist Charles Frederic Gerhardt treated the
medicine sodium salicylate with acetyl chloride to produce acetylsalicylic acid for the first
time. For the next fifty years, other chemists established the chemical structure and came
up with more efficient production methods. In 1897, scientists at the Bayer company began
studying acetylsalicylic acid as a less-irritating replacement medication for common
salicylate medicines. By 1899, Bayer had named it "Aspirin" and sold it around the
world. Aspirin's popularity grew over the first half of the twentieth century leading to
competition between many brands and formulations.

STRUCTURE
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PHYSICAL PROPERTIES
Aspirin, an acetyl derivative of salicylic acid.
 Structure: white crystalline solid
 Acidic Nature: weakly acidic substance
 Melting Point: 136 °C (277 °F)
 Boiling point: 140 °C (284 °F)
 Acid dissociation constant (pKa): 3.5 at 25 °C (77 °F).

MEDICAL USE

Aspirin is used in the treatment of a number of conditions, including fever, pain, rheumatic
fever, and inflammatory conditions, such as rheumatoid arthritis, pericarditis, and Kawasaki
disease. Lower doses of aspirin have also been shown to reduce the risk of death from
a heart attack, or the risk of stroke in people who are at high risk or who have
cardiovascular disease, but not in elderly people who are otherwise healthy. There is some
evidence that aspirin is effective at preventing colorectal cancer, though the mechanisms of
this effect are unclear.
Pain
Aspirin is an effective analgesic for acute pain, although it is generally considered inferior
to ibuprofen because aspirin is more likely to cause gastrointestinal bleeding. Aspirin is
generally ineffective for those pains caused by muscle cramps, bloating, gastric distension,
or acute skin irritation. As with other NSAIDs, combinations of aspirin and caffeine provide
slightly greater pain relief than aspirin alone. Effervescent formulations of aspirin relieve
pain faster than aspirin in tablets, which makes them useful for the treatment
of migraines. Topical aspirin may be effective for treating some types of neuropathic pain.
Headache
Aspirin, either by itself or in a combined formulation, effectively treats certain types of a
headache, but its efficacy may be questionable for others. Secondary headaches, meaning
those caused by another disorder or trauma, should be promptly treated by a medical
provider.
Among primary headaches, the International Classification of Headache
Disorders distinguishes between tension headache (the most common), migraine,
and cluster headache. Aspirin or other over-the-counter analgesics are widely recognized as
effective for the treatment of tension headache.
Aspirin, especially as a component of an aspirin/paracetamol/caffeine combination, is
considered a first-line therapy in the treatment of migraine, and comparable to lower doses
of sumatriptan. It is most effective at stopping migraines when they are first beginning.
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Fever
Like its ability to control pain, aspirin's ability to control fever is due to its action on
the prostaglandin system through its irreversible inhibition of COX. Although aspirin's use as
an antipyretic in adults is well established, many medical societies and regulatory agencies,
including the American Academy of Family Physicians, the American Academy of Paediatrics,
and the Food and Drug Administration, 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. Because of the risk of Reye's syndrome in children, in 1986, the FDA
required labelling on all aspirin-containing medications advising against its use in children
and teenagers.
Inflammation
Aspirin is used as an anti-inflammatory agent for both acute and long-term inflammation, as
well as for treatment of inflammatory diseases, such as rheumatoid arthritis.

AIM
To synthesize some common pain relievers: aspirin and to determine the purity of the
aspirin.

THEORY
 Aspirin 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.
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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 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.

Materials Needed
1. Salicylic acid
2. Acetic anhydride
3. Sulphuric acid, concentrated
4. Ethanol
5. Dropper
6. Erlenmeyer flask, 125-mL
7. Beakers, 2 400-mL, 100-mL, 10 or 20-mL
8. Graduated cylinders, 10-mL, 25-mL
9. Watch glass
10. Stirring rod
11. Vial to hold aspirin sample
12. Ring stand
13. Clamp (to hold 125-mL Erlenmeyer flask)
14. Buchner funnel
15. Filter paper to fit Buchner funnel
16. Vacuum filtration flask
17. Rubber tubing for vacuum flask
18. Ice
19. Thermometer, 110°C
20. Melting point capillary tube
21. Melting point apparatus
22. dropper
23. Disposable IR card
24. Optional: rubber gloves

SAFETY PRECAUTIONS
1. Wear safety glasses or goggles at all times in the laboratory.
Acetic anhydride is corrosive and its vapour is irritating to the respiratory system.
2. Avoid skin contact and inhalation of the vapours. In the event of skin contact, rinse
well with cold water.
3. Sulphuric acid is corrosive. Avoid skin contact. In the event of skin contact, rinse well
with cold water.
4. P-aminophenol is harmful by inhalation and by contact with the skin. In the event of
skin contact, rinse well with cold water.
5. If any harmful vapours are inhaled, move to an area where fresh air is available.
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Procedure
1. Weigh out 2.0 g of salicylic acid. Place it in a 125-mL Erlenmeyer flask.
2. Add 5 mL of acetic anhydride. Swirl the flask to wet the salicylic acid crystals. Add 5
drops of concentrated sulphuric acid, to the mixture.
3. Gently heat the flask in a boiling water bath for about 10 minutes.
4. Remove the flask from the hot water bath and add 10 mL of deionized ice water to
decompose any excess acetic anhydride. Chill the solution in an ice bath until crystals
of aspirin no longer form, stirring occasionally to decompose residual acetic
anhydride. If an "oil" appears instead of a solid, reheat the flask in the hot water
bath until the oil disappears and again cool.
5. Set up a vacuum filtration apparatus. Wet the filter paper in the Buchner funnel with
1-2 mL of distilled water.
6. Turn on the water aspirator. Decant the liquid onto the filter paper, minimizing any
transfer of the solid aspirin. If some aspirin is inadvertently transferred to the filter,
that will not cause any difficulty.
7. Add 15 mL of cold water to the flask, swirl, and chill again. Pour the liquid and the
crystals of aspirin onto the filter paper. Repeat until the transfer of the crystals to
the vacuum filter is complete.
8. Wash the aspirin crystals on the filter paper with 10 mL of ice water.
9. Maintain the vacuum to dry the crystals as best possible.
10. If aspirin forms in the filtrate in the vacuum flask, transfer the filtrate and aspirin to a
beaker, chill in an ice bath, and vacuum filter as before, using a new piece of filter
paper. Dispose of the filtrate in the sink.
11. Determine the mass of the crude aspirin crystals.

Recrystallization of the Aspirin.

1. The major impurity in aspirin is salicylic acid. It can be removed by a
recrystallization.
2. Place the aspirin crystals in a 100-mL beaker. Add 8 mL of ethanol and 25 mL of
water.
3. Warm the mixture in a 60°C water bath (no flame, use a hot plate or a hot water bath).
Warm the mixture until the aspirin dissolves. (If the solid does not dissolve after
heating, consult with your instructor.)
4. Cover the beaker with a watch glass, remove it from the heat, and set it aside to cool
slowly. Set the beaker in an ice bath. Beautiful needle-like crystals of acetylsalicylic
acid form.
5. Collect the aspirin by vacuum filtration. Wash the crystals with two 10-mL volumes
of ice water. Maintain the vacuum to air dry the aspirin. If time does not permit, place
the filter paper and aspirin sample on a watch glass and allow them to air-dry. The
time for air-drying the sample may require that it be left with your instructor until the
next laboratory period.
6. Transfer the dry aspirin crystals to a pre-weighed sample container or vial. Determine
the mass of the aspirin crystals.
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Determine the Melting Point of the Aspirin Sample

1. Fill a capillary melting point tube to a depth of 0.2 cm with the recrystallized aspirin.
Place the capillary tube in the melting point apparatus. Determine its melting point.
2. Pure aspirin melts at 135°C.
3. The aspirin sample should be labelled with your name, the mass of the aspirin,
percentage yield and its melting point.

Verification of Aspirin
1. Place a small amount of your aspirin sample (about 0.10 g) in a 10-mL or 20-mL
beaker. Add approximately 2 mL of ethanol. Stir or swirl to dissolve. If necessary,
warm the mixture slightly on a hot plate to assist in solution.
2. CAUTION: Ethanol is flammable. Do not allow it to boil.
3. Place one or two drops of the acetaminophen solution on a disposable IR card. Allow
the ethanol to evaporate.

Report Sheet

Name ______________________________________ Class/Section _______________

Date ________________________

PREPARATION OF ASPIRIN

DATA
Preparation of Aspirin

 Mass of salicylic acid ____________ g

 Mass of crude aspirin ____________ g
 Mass of purified aspirin ____________ g
 Theoretical yield of aspirin (calculations shown below) ____________ g
 Percent yield of aspirin (calculations shown below) ____________ %
 Melting point of aspirin ____________°C
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CALCULATIONS

Bibliography
 https://en.wikipedia.org/wiki/Aspirin
 www.webassign.net
 pages.mtu.edu
 Comprehensive Chemistry Practical Lab Manual
 NCERT Chemistry(Chapter: Chemistry in Everyday Life)
 Comprehensive Chemistry(Chapter: Chemistry in Everyday Life)