ASPIRIN

AND ITS
USES
 CONTENT
1 INTRODUCTION

2 PREPARATION OF ASPIRIN

3 SYNTHESIS OF ASPIRIN

4 REACTION MECHANISM

5 USES OF ASPIRIN

6 SIDE EFFECTS OF ASPIRIN

7 CONCLUSION
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
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.

SOME IMAGES OF ASPIRIN:

FORMULA OF ASPIRIN

APPARATUS 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

CHEMICALS REQUIRED:
⁰ Salicylic Acid- 10 g
⁰ Pyridine - 7 ml
⁰ Acetyl Chloride- 7.5 ml
⁰ Acetic Acid
⁰ Conc. Hydrochloric Acid

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, in 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 102.1g/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

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:
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.
Obtain the mass of the watch glass and record it on
your data sheet.
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.
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.
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 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 vapour.
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
vapour being formed in this step 8.
When the liquid has stopped giving off vapour,
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.
 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.
 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.
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.
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.
Heat the contents of the flask to boiling. The
crystals should all dissolve. If they don’t, add a few
millilitres 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.
 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.
 Filter the crystals as you did in step 11. Transfer
them to the watch glass.
 Weigh the crystals on the watch glass, and
calculate your percent yield.
 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.

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.

CALCULATION:
 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

SYNTHESIS OF ASPIRIN:
The synthesis of aspirin is classified as an
esterification reaction. Salicylic acid is treated with
acetic anhydride, an acid derivative, causing a chemical
reaction that turns salicylic acid’s hydroxyl group into
an ester group (R-OH R-OCOCH3).This process
yields aspirin and acetic acid, which is considered a
byproduct of this reaction. Small amounts of sulfuric
acid (and occasionally phosphoric acid) are almost
always use as a catalyst.
REACTION MECHANISM:
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 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 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 the
benefits are greater than the risks due to bleeding in
those 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 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.
 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 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
 SIDE EFFECTS OF ASPIRIN
COMMON SIDE EFFECTS:
Vomiting
Stomach pain
Heart burn
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
CONCLUSION:

In conclusion, the project on aspirin and its

uses sheds light on the multifaceted nature of this
widely-used medication. Aspirin, known for its
analgesic, anti-inflammatory, and antipyretic properties,
has been a staple in medicine cabinets for decades. Its
versatility extends beyond pain relief, with significant
implications in cardiovascular health, particularly in the
prevention of heart attacks and strokes.
Through a comprehensive examination of
aspirin's mechanisms of action, pharmacokinetics, and
therapeutic applications, this project underscores its
importance in various medical contexts. From
managing acute pain to reducing the risk of
cardiovascular events, aspirin's efficacy is supported by
a wealth of scientific evidence.
However, it's crucial to acknowledge the
potential risks associated with aspirin use, including
gastrointestinal bleeding and other adverse effects,
particularly in certain populations such as those with a
history of ulcers or bleeding disorders.
 Moving forward, ongoing research continues
to explore aspirin's role in healthcare, including its
potential in cancer prevention and treatment. As our
understanding evolves, it's essential for healthcare
professionals and patients alike to weigh the benefits
and risks carefully, ensuring informed decision-making
regarding aspirin therapy.
Ultimately, this project underscores aspirin's
enduring significance in modern medicine while
emphasizing the importance of responsible use and
ongoing research to maximize its benefits while
minimizing potential harm.