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TA 1

CHEM 22161
Synthesis of Medicinal Agent:
Synthesis of Aspirin

Student Name :
Wekasinghe

Kasun

Perform Date

25-08-2015

Date :

25-08-2014

Experiment number : 01
Experiment Title :

Synthesis of Medicinal Agent:


Synthesis of Aspirin

Objectives :
To introduce single step synthetic reactions , to
familiarize with purification and identification techniques of
solid organic products and to introduce limiting reagent
and percentage yield.

Theory :
Ethyl salicylate is the ester formed by the condensation of salicylic acid
and ethanol. It is a clear liquid that is sparingly soluble in
water, but soluble in alcohol and ether. Ethyl acetate is used
as a pain killer that should be taken orally where it is called
Aspirin. Aspirin is used to treat pain, and reduce fever or
inflammation. It is sometimes used to treat or prevent heart
attacks, strokes, and chest pain. For the Synthesis H3PO4 is used as a catalyst.

Methyl salicylate can be produced by condensation of salicylic acid with methanol.


As a derivative of salicylic acid, it is used commonly in
external application ointments for the relief of muscle pain and
cramping because it can penetrate the skin . It has a pleasant
smell it is usually called Oil of Wintergreen. Oil of
wintergreen is also used as a flavoring agent in commercial
food products.

Ethyl salicylate Synthesis Mechanism

Materials:
Conical Flask (125 mL)
Salicylic acid (1.5 g)
Acetic anhydride (3.5 mL)
Distilled Water
Glass rods
Beakers
Buchner Funnels
Vacuum Filter

Glass wear & Chemicals


Filter Papers
Phosphoric Acid (H3PO4) (85%,
0.50mL, 10 drops)
Ice
Hot Plate
Ethyl Alcohol
Watch glasses
Spatula

Procedure:
Pure salicylic acid (1.5 g ) was pleased in a conical flask (125 mL) and Acetic
anhydride(3.5 mL) was added . Phosphoric acid (85%, 0.50 mL,10 drops) was added
and was mixed well. The synthesis reaction was run by heating the mixture in a
boiling water bath for 10 minutes with continue stirring. After 10 minutes cold
water (10 mL) was added. After addition distilled water (40mL) was added and the
mixture was mixed well and cooled in an ice bath. After crystal formation the
mixture was filtered in a Buchner funnel using a vacuum filter. Aspirin obtained by
the crystallization was dried and the weight was taken.
Few crystals of Aspirin was taken to a test tube and Methanol (1mL) was
added and dissolved. After dissolution FeCl3 (2%, 0.15mL) was added and color
change was observed.
Impure aspirin obtained was dissolved in minimum amount of Ethyl Alcohol
and was warmed in a water bath until solution is completely dissolved. After
complete dissolution, distilled water was added until a permanent turbidity is
formed. The warming is continued till the solution become transparent and taken to
cool down. After crystals form crystals were filtered and dried. Dried crystals were
collected and melting point was determined.

Results :
Total Weight of the sample(Aspirin, Filter papers) : 6.93 g
Weight of the wet Filter papers
: 2.34 g
Salicylic acid test for aspirin is Negetive. No color change in 2% FeCl3
Melting point of the Synthesized Aspirin : 1350C

Calculation :

Molar ratio
Density
Molecular weight
Mass
Volume
Purity
Initial moles
Reacted moles
Left moles

1
138 g mol-1
1.5g
99%
0.0108 mol
0.0108 mol
0

1
102g mol-1
1.08 g mL-1
3.5 mL
98%
0.0363 mol
0.0108 mol
0.0255 mol

1
180 g mol-1
0.0108 mol
0.0108 mol

If Acetic anhydiride is the limiting Reagent


Salicylic : Acetic anhydiride =

1 :

Number of Acetic anhydiride moles = (1.08g mL-1 x 3.5 mL x 98)/(100 x 102 g mol-1)
= 0.0363 mol
Number of needed Salicylic = 0.0363 mol
If Salicylic acid is the limiting Reagent
Salicylic : Acetic anhydiride =

1 :

Salicylic Initial number of moles = (1.5 g x 99 / 100 x 138 g mol-1


=
0.01076 mol
= 0.0108 mol
Number of needed Acetic anhydirid = 0.0363 mol
So the Limiting reagent is Salicylic Acid
Theoretical ;
Weight of Pure Aspirin = 0.0108 mol x 180 g mol-1
= 1.944 g

Observed and measured ;


Total Weight of the sample(Aspirin, wet Filter papers) = 6.93 g
Weight of the wet Filter papers

= 2.34 g

Final Weight of Pure Aspirin = (5.93- 3.34) g


= 2.59 g
Percentage yield = Observed weight x 100%
Theoretical weight
= (2.59 g x100 %) / 1.944 g
= 133.23 %

Discussion :
In this experiment the Limiting reagent is Salicylic acid. So in
the medium an excess Acidic anhydride is left behind. Due to this
excess acetic anhydride solution the synthesized sample containing
solution get a light pink residue. So it is important to remove any
unwanted chemicals to get purified Aspirin. So a recrystallization
method is done using ethyl alcohol and water.
In this experiment 85% syrus Phosphoric acid is used as a
catalyst. It help the reaction by involving in its mechanism to
synthesise aspirin. It catalyses and increase rate of esterification.
It is important to test the presence of trace amount of salicylic
acid. To qualitatively identify 2% FeCl3 is used. FeCl3 gives dark purple
color is observed. But for this experiment as the salicylic is the limiting
reagent so that it does not give such a color change.
The yield of the synthesized product is important to chemist as it
determines the easiest and high product rate of given compound in a
Industrial level. In this experiment the yield of pure Aspirin was
calculated using both observed and theoretical weight values. The
Percentage yield was 133.23%. Usually it should be a value less than
100%. But in this experiment due to presence of water molecules/
wetness it becomes a higher value. So it is important to dry the aspirin
sample before finding the percentage yield.
In this experiment the Purity of the aspirin Synthesized is also
tested. It is done by using the melting point. In this experiment the
melting point observed was 1350C. by the Experimental true value for
the aspirin Melting point is 138 0C. This slight deviation occurs due to
the presence of water molecules/wetness of aspirin sample.

Conclusion :
Percentage yield is 133.23% and not pure Aspirin.
Melting Point is 1350C
Aspiri n Synthesised is not pure due to the presence of water.

References :
http://www.drugs.com/aspirin.html (25-08-2015)
http://www.academia.edu/4728996/Acetylsalicylic_Acid_Aspirin_Synthesis (25-08-2015)
http://chemwiki.ucdavis.edu/Physical_Chemistry/Physical_Properties_of_Matter/Solutions
_and_Mixtures/Case_Studies/RECRYSTALLIZATION (25-08-2015)
http://www.wiredchemist.com/chemistry/instructional/laboratorytutorials/recrystallization(25-08-2015)