VIDYA NIKETAN SCHOOL

2022-2023

CHEMISTRY PROJECT

TOPIC: ASPRIN

NAME: MAYANK KUMAR

CLASS: XII-S3
ROLL NO.:
Under the supervision of
MRS. POONAM TEWATIA
 CERTIFICATE
This is to certify that Mayank Kumar of class XII-S3 has
successfully completed his/her project on topic Aspirin as
prescribed by Mrs. Poonam Tewatia during the academic year
2022-2023 as per the guidelines given by CBSE.

Sign of external

Sign of teacher
 ACKNOWLEDGEMENT
At the outset, I Express a great sense of gratitude towards my
guide Mrs. Poonam Tewatia 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. I would also like to thank my
esteemed principal sir for giving me the opportunity to
completed my work. Finally, I am thankful to my acquaintance.
 INDEX
S.NO. TOPIC Pg No.
1. INTRODUCTION

2. THE CREATORS: THE PRIONERS OF ASPRIN

SYNTHESIS
3. THEORY

4. PREPARATION OF ASPIRIN

5. SAFETY MEASURES

6. USES

7. SIDE EFFECTS

8. CONCLUSION

9. PHOTOGALLERY

10. BIBLIOGRAPHY
 INTRODUCTION
One of the most widely used nonprescription drugs is
aspirin. In the United States, more than 15,000 pounds are
sold each year. This is not surprising when one considers
the medicinal applications for aspirin. It is an effective
analgesic (pain killer) that can reduce the mild pain of
headache, toothache, neuralgia (never pain), muscle pain,
and join pain (from arthritis and rheumatism). Aspirin
behaves as an antipyretic drug (it reduces fever) and it is
an anti-inflammatory agent capable of reducing swelling
and redness associated with inflammation. It is also an
effective agent in preventing strokes and heart attacks due
to its ability to act as an anticoagulant by preventing
platelet aggregation. The father of modern medicine was
Hippocrates, who lived sometime between 460 B.C and
377 B.C. Hippocrates left historical records of pain relief
treatments, including the use of powder made from the
bark and leaves of the willow tree to help heal headaches,
pains and fevers. By 1829, scientists discovered that it was
the compound salicin in willow plants that gave pain relief.
It was a short time later that a tiny amount of bitter tasting,
yellow, needle-like crystals were isolated from willow bark
by Johann Buchner, professor of pharmacy at the
University of Munich. By 1829, a French chemist
improved the extraction procedure and was able to obtain
about 30g from 1.5kg of bark. In 1838, an Italian chemist
was able convert salicin to an acid of crystallized, colorless
needles, which he named salicylic acid. Since salicylic acid
contains phenolic and carboxylic acid groups, it was
irritating to the mouth, throat, and stomach. After
considerable work, the derivative acetylsalicylic acid was
found to have similar pain- relieving properties without the
harsh side effects. It was in 1899, that the Bayer Company
in Germany patented
the ester acetylsalicylic acid and marketed the product as
“aspirin” in 1899. Their
studies showed that this material was less of an irritant and
the acetylsalicylic acid hydrolyzed in the small intestine to
salicylic acid, which was then absorbed into the
bloodstream. The relationship between salicylic acid and
aspirin
THE CREATORS: THE PRIONERS OF
ASPRIN SYNTHESIS
The first person to do so was a French chemist named
Charles Frederic Gerhardt. In 1853, Gerhardt neutralized
salicylic acid by buffering it with sodium (sodium
salicylate) and acetyl chloride, creating acetylsalicylic
acid. Gerhardt's product worked but he had no desire to
market it and abandoned his discovery. In 1899, a German
chemist named Felix Hoffmann (Fig. 2), who worked for a
German company called
Bayer
, rediscovered Gerhardt's formula. Felix Hoffmann made
some of the formula and gave it to his father who was
suffering from the pain of arthritis, with good results. Felix
Hoffmann then convinced Bayer to market the new wonder
drug. Aspirin was patented on February 27, 1900. The
folks at Bayer came up with the name Aspirin, it comes
from the 'A" in acetyl chloride, the "spir" in spiraea
ulmaria (the plant they derived the salicylic acid from) and
the 'in' was a then familiar name ending for medicines.
Aspirin was first sold as a powder. In 1915, the first
Aspirin tablets were made. Interestingly, Aspirin ® was
once a trademark belonging to Bayer. After Germany lost
World War I, Bayer was forced to give it up as part of the
Treaty of Versailles in 1919.
 THEORY
Aspirin, acetylsalicylic acid, was first synthesized in 1893
by Felix Hofmann, a chemist for the German firm of
Bayer.This compound had he 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.
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
 PREPARATION OF ASPIRIN
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 (H 3PO 4). 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 an ice bath. Again, avoid swirling or stirring it any
more than necessary. Keep the flask in the ice bath about 5
minutes.
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 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
16 Transfer them to the watch glass.
17. Weigh the crystals on the watch glass, and calculate your
percent yield.
18. 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.
 SAFETY MEASURES
The chemicals used to synthesize aspirin present a health
hazard and exposure should be kept to a minimum:
1) Sulfuric Acid: A highly corrosive liquid that will cause
severe burns if it comes into contact with skin.
2) Salicylic Acid: Harmful by inhalation, ingestion, and
through skin absorption. An irritant.
3) Acetic anhydride: Poison. Corrosive. Cuases severe
burns. Harmful if swallowed or inhaled. Causes severe
respiratory irritation. Eye contact may cause serious
irritation or burns.
4) Ferric Chloride Solution: Corrosive
5) Ethanol: Toxic and flammable
6) Always wear Lab Grade coats and Safety Goggles
 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 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 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 rea, 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
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 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 are commonly used to verify the
purity of medications. Filtration is used to finish drying
organic material prior to the spectrometries.
BIBLIOGRAPHY