Chemistry Investigatory

Project on Aspirin

2018-19
 Acknowledgement
At the outset, I Express a great sense of gratitude towards my
guide Mr. Subhojit Patra 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 my
esteemed principal madam for giving me the opportunity to
completed my work. Finally, I am thankful to my acquaintance.
This is to certify that Aditya Gupta of Class XII(Science) of Amrita
Vidyalayam, Durgapur has completed his project work under the
guidance and supervision of Mr.Subhojit Patra.

I Certify that this project is upto the expectation of CBSE guidelines.

…………………………………….
(Principal’s Signature)
 Teacher’s Certificate
This is to certify that Aditya Gupta of Class XII(Science) of class
XII(Science) of Amrita Vidyalayam, Durgapur has completed his
project under my guidance and supervision.

I Certify that this project is upto the expectation of CBSE guidelines.

……………………………………………..

(Teacher’s Signature)
 INDEX

Topic Pg. No

1.Inroduction 1

2.Preparation of 2-6
Aspirin
3.Uses 7-9

4.Side Effects 10

6.Conclusion 11

7.Photo Gallery 12

8.Bilbliography 13
 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.
 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. 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.

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 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 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.
• 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
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
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 breathing

➢ Cold, clammy skin

➢ Bloody vomit or vomit that looks like coffee grounds

➢ Bright red blood in stools or black or tarry stools

 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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