Group 5

group leader :Naser Ayat

Group members :Mahreen Shafiq
Maria Hashmi
Marium Tehreem
Synthesis of aspirin
 IUPAC Name 2-acetyloxybenzoic acid
Chemical name : 2-
Ethanoyloxybenzene carboxylic acid
After experiment students will be able to:

1 2 3
Understand the Identify the Learn the aspirin
process of aspirin advantage of aspirin purification
preparation . as pain reliever . procedure.
 Where Did Aspirin
Come From?
Aspirin was first derived from the bark of a willow
tree.
Hippocrates described it as a bitter powder that
reduced fever.
In 1897 a German chemist Felix Hoffman who worked
in German company, made some formula and gave it
to his father who suffering from pain arthritis .
With good result , Felix convinced Bayer to market the
new wonder drug.
Aspirin was first as powder.
In 1915 the first aspirin tablets made.
 The aim of the experiment is
synthesis aspirin and evaluate the
purity of their product 

 aim of the
experiment  and
Synthesis of aspirin from salicylic principle:
acid occurs by acetylation process in
acidic medium. Salicylic acid interacts
with acetic anhydride in presence of
few drops of concentrated sulphuric
acid to produce aspirin and a
molecule of acetic acid.
 • Physical State: Crystalline
• Appearance : white
• Odor: Odorless
properties: • Nature: acidic & aromatic
• pH: 3.5
• Solubility : in organic solvent
• Molecular formula: C9H8O4
• Molecular weight: 180.16
 • The chemicals used to synthesize aspirin present a
health hazard and exposure should be kept to
minimum:
• 1) Sulfuric Acid: A highly corrosive liquid that will
cause severe burns if it comes into contact with
skin.

Safety
• 2) Salicylic Acid: Harmful by inhalation, ingestion,
and through skin absorption. An irritant.
• 3 Acetic anhydride: Poison. Corrosive. Causes
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
Equation:
 Conical flask

Water bath

Material Stirrer

required: Thermometer

Funnel

Filter paper
Chemicals:
conc.H2SO4
Few drops

Acetic anhydride
6ml
Salicylic acid
3g/mol
 • Add about 2 g of salicylic acid to a pre-weighed
50 mL Erlenmeyer flask .
• Add 5.0 mL of acetic anhydride to the flask.
• Add 5 drops of phosphoric acid to the mixture
and stir with a clean glass stirring rod.
Procedure • Caution: acetic anhydride and phosphoric acid
can produce burns. They are located in the fume
hood.
• Clamp the flask to a ring stand and immerse it in
a 400 mL beaker containing tap water.
• Heat the bath to 750c and maintain this
temperature for 5 minutes while stirring the
mixture to dissolve the contents.
 After heating, cautiously add 2 mL DI water to the
flask and stir.
Remove the mixture from the water bath and let
cool to room temperature (25oC).
Remember DO NOT touch the hot ring clamp until
has had sufficient time to cool.
Once the flask is cooled to room temperature, add
Procedure: 20 mL of DI water and stir
.Place the flask in an ice bath to speed the
crystallization process.
Allow the flask to remain in the ice bath for 5
minutes.
If crystals have not formed after 5 minutes,
vigorously scratch the inside of the flask with a
glass stirring rod
 • Collect the Aspirin crystals by vacuum filtration using
a Buchner funnel.
• Secure the funnel by clamping it to a ring stand to
prevent spilling your residue.
Procedure: • Remember moisten the filter paper once it is inside
the funnel by using a small amount of DI water in a
squeeze bottle.
• This will secure the filter paper so that it is “flush” to
the bottom surface of the funnel
• wash the aspirin crystals with a 5 mL portion of ice-
cold DI water.
• Turn on the suction to remove the wash water and
repeat the washing with another 5 mL portion of ice-
cold DI water
• Allow air to be drawn over the crystals by suction for
3 minutes until the crystals are dry.
Procedure:
• When the crystals are dry and fluffy, determine the mass of your
aspirin. Record this weight as your actual yield of aspirin.
• Calculate the amount of aspirin you could produce, called the
theoretical yield of aspirin.
• This value is based on the stochiometric amounts of reactants in the
balanced equation and the limiting reagent.
• Calculate the percent yield of aspirin you produced by dividing the
actual yield by the theoretical yield of aspirin and multiply by 100%.
 Calculation:
• Molecular weight of
salicylic acid: 138
• Molecular weight of
aspirin:180
• 138 g of salicylic acid
yield =180 g of aspirin
• So 1g =180/138
• Thus 5g=5.180/138=6.5g
Calculation formula:
Testing the purity of aspirin:
 Testing the Purity of your Product 
•  If any salicylic acid is left unreacted at the end of our experiment,
we can detect its presence with 1% iron(III) chloride solution.
•  The phenol group present in salicylic acid will turn purple.
•  “Pure” aspirin will not react with iron(III)chloride.
Uses:
• Aspirin is used to reduce fever and relieve mild to moderate pain from
conditions such as muscle aches, toothaches, common cold,
and headaches.
• It may also be used to reduce pain and swelling in conditions such
as arthritis.
•  Aspirin is known as a salicylate and a non steroidal anti-inflammatory
drug (NSAID).
• It works by blocking a certain natural substance in your body to
reduce pain and swelling.
 Side effect of aspirin are:
Heart burn , abdominal pain
• Stomach upset ,dark urine
• Difficulty in hearing , Kidney problems
• Ringing in ears, vomiting
• Nausea, dizziness
Side effect: • Generally people do well with aspirin , but it’s
very important to remember that aspirin
should never be taken on an empty stomach .
You always some food & it needs to be taken
after having food, because it can cause gastric
irritation or acidity.
• But generally it is well-tolerated. Again very
important to remember do not self medicate
on your own, always consult with your doctor
before you take this medicine.
 • Aspirin is used to treat or prevent heart
attack, strokes,& chest pain.
• It is used as pain-killer
Important • Aspirin should not be given to child who has
information a fever, especially if the child also has flu
symptoms or chicken pox.
about • Aspirin can cause serious condition , called
aspirin: Reye’s syndrome in children
• Avoid drinking alcohol while you are talking
this medication. Because alcohol may
increase your risk of stomach bleeding
Caution!

¨ Be careful not to
¨ Do NOT take your
inhale the salicylic
aspirin home and use
acid when weighing it
it on yourself.
out at the balances!!!