Synthesis of Aspirin.edited
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1
SYNTHESIS OF ASPIRIN
Student’s Name
Institutional Affiliation
Course
Instructor’s Name
Date
2
Synthesis of Aspirin
Objective
To react 2.1 gram of salicylic acid with 5 gram of acetic anhydride in the presence of
concentrated sulphuric acid to form Aspirin. To prepare benzoic acid by reacting 5 gram of ethyl
benzoate with 50 cm3 of sodium hydroxide, and finally test the purity of Aspirin and the
functional group present.
Materials and Equipment’s
Thermometer
Stopwatch
Magnetic stirrer
Erlenmeyer flask
Test tube
Dropper
Clamp and stand
Flat bottomed flask
Beaker
Buchner funnel
Filter paper
Spatula
3
Reflux apparatus
Stirrer rod
NAME
FORMULA
AND
STRUCTURE
MW
(G/
ML)
MP
(
)
℃
BP
(
)
℃
DENS
ITY
(G/C
M3)
COLOU
R
SOLID/L
IQUID
WATER
H2O
18.0
2
0
100
1
colorless
liquid
ETHANOL
C2H60
46.0
1
-
114.
5
78.5
0.789
colorless
liquid
SODIUM
HYDROXIDE
NaOH
39.9
97
318.
4
1388
2.13
white
solid
IRON (III)
CHLORIDE
FeCl3
162.
2
306
315
2.9
Dark
green
solid
HYDROCHLORI
C ACID
HCl
36.4
58
-
114.
22
-
85.0
5
1.2
Colorless
liquid
CONCENTRATE
D SULPHURIC
ACID
H2SO4
98.0
79
10
337
1.83
colorless
liquid
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4
SALICYLIC
ACID
C7H6O3
138.
12
211
158.
6
1.44
White
crystals
solid
BENZOIC ACID
C7H6O2
122.
12
122.
3
249.
2
1.27
colorless
liquid
METHYL
BENZOATE
C8H8O2
136.
15
-15
199
1.08
colorless
liquid
ASPIRIN
C9H8O4
180.
158
135
140
1.4
White
crystals
solid
ACETIC
ANHYDRIDE
C4H6O3
102.
09
-
73.1
139.
8
1.08
colorless
liquid
5
Procedure
Procedure
observations
1.
Weigh 2.1 gram of salicylic acid
2.
Put this mass into an Erlenmeyer
flask in a water bath maintained at
45 degrees Celsius to 50 degrees
Celsius.
3.
Add 5 ml of acetic anhydride into
the Erlenmeyer flask.
4.
Add a magnetic stirrer as the flask
is in a heating mantle that allows
stirring.
5.
Add five drops of concentrated
sulphuric acid.
6.
Allow the Erlenmeyer flask to cool
to allow the product to recrystallize.
If it doesn't recrystallize, scratch the
inside of the wall with an ice cube.
Cloudy so formed
7.
Add 30 ml of ice-cold water, and
place it in the ice cubes.
8.
Set the vacuum filtration apparatus
9.
Transfer the solution into the
Buchner funnel to allow filtration
10. Add 30 ml of water to the Buchner
funnel will help to get rid of
impurity.
11. Collect a tiny amount of residue for
purity analysis
12. Add five ethanol to the filtrate on a
6
heating mantle to recrystallize
13. Add 40 ml of water into the beaker
and allow it to cool to room
temperature for recrystallization.
Scratch the walls with an ice cube to
allow the crystals to form
14. Put the beaker in the ice cube and
set up the vacuum filtration
apparatus.
15. Put the solution in the Buchner
funnel to allow filtration. Rinse the
funnel with ice-cold water after
filtration
16. Take a small amount of the filtrate
(pure Aspirin) for analysis.
Procedure for Purity Analysis
FeCl3 Test
Procedure
Observations
Place a small amount of salicylic acid into a
beaker
Colorless solution
To this beaker and the two other beakers
containing pure and crude Aspirin, add I
ml of 95% ethanol.
Colorless solution
Add 1 ml of 25 % into the three beakers
In the Crude Aspirin
Purple color
In salicylic acid
Purple color
Pure Aspirin
No colorless
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7
Saponification of Ester
Preparation of Benzoic acid
Objective
To react 5 gram of ethyl benzoate with 50 cm3 of sodium hydroxide in the presence of
hydrochloric acid to produce benzoic acid
Procedure
procedure
Observation
1.
Weigh 5 gram of ester, ethyl
benzoate, in a conical flask
2.
Add 50 cm3 of NaOH into the
solution.
3.
Add boiling chip and turn on the
heating mantle.
4.
Set up the reflux apparatus, and
perform a reflux experiment
5.
Cool the mixture to room
temperature and transfer into a
beaker
6.
Add 30 cm3 of hydrochloric acid
into the mixture in the beaker
White precipitate formed
7.
Setup the vacuum filtration
apparatus and filter the reaction
mixture. Wash with water to allow
the total transfer.
8.
Transfer the residue into a beaker
9.
Add 100cm3 of water into the
Clear solution formed
8
benzoic acid and stirrer
continuously, and heat to 60 cm3 to
20 cm3 to all the benzoic acid to
dissolve.
10. Filter the solution via vacuum
filtration and allow it to
recrystallize
11. Transfer the filtrate into a beaker,
and allow it to cool to room
temperature
Cloudy solution formed
12. Set up the vacuum filtration and
filter pure benzoic acid. Wash out
the beaker with water to ensure
complete transfer
13. Transfer the benzoic acid crystals
into a preweighed petri dish. And
allow it to dry and weigh.
Results
Synthesis of Aspirin
2.1 g Salicylic acid
5 ml of acetic anhydride
1 ml of concentrated sulphuric acid
9
From the equation provided, the mole ratios are 1:1
Hence the number of moles of salicylic acid is equal to the number of moles of Aspirin.
The number of moles of salicylic = weighed mass/ relative mass
Weighed mass = 2.0g
Relative mass = 138.12 g/mol
Thus, number of moles = (2.0g/138.12g/mol) = 0.0145moles
These moles are equal to those in aspirin
Thus, theoretical weight = no. of moles * MW
MW of Aspirin = 180.158 g/mol
Theoretical weight = 0.0145 *180.158 = 2.6087g
Actual weight = 1.1 g
% percent yield = (actual weight/theoretical value) *100
= (1.1g/2.6087g) *100
= 42.1666%
= 42.17%
Preparation of Benzoic acid
0.9 g of Methyl benzoate
50 cm3 of sodium hydroxide
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10
0.54g Benzoic acid
From the equation provided, the mole ratios are 1:1
Hence the number of moles of methyl benzoate is equal to the number of moles of Benzoic.
The number of moles of methyl benzoate = weighed mass/ relative mass
Weighed mass = 0.9g
Relative mass = 136.15 g/mol
Thus, number of moles = (0.9g/136.15g/mol) = 0.0066moles
These moles are equal to those in Benzoic Acid
Thus, theoretical weight = no. of moles * MW
MW of benzoic acid = 122.12g/mol
Theoretical weight = 0.0066 *122.12 = 0.805992g
Actual weight = 0.54 g
% percent yield = (actual weight/theoretical value) *100
= (0.54g/0.805992g) *100
= 66.9982%
= 66.99%
Discussion
2.1 g of salicylic acid was reacted with 5 ml of acetic anhydride in the presence of 1 ml of
concentrated sulphuric acid, which acted as a catalyst. When concentrated sulphuric acid was
11
added to the solution, a cloudy solution was formed, which indicated Aspirin's presence. The
solution was carried out at 50 degrees Celsius for 5 minutes, which ensures enough heat and time
for everything to react. The product (Aspirin) was precipitated, collected, and recrystallized to
purify it. Water was added to the funnel to get rid of impurities. Acetic anhydride is eliminated
by the rinsing of the funnel and the beaker with water. When iron (III) chloride was added to
either the pure or crude Aspirin and salicylic color change was observed, which identified if the
pure Aspirin was pure. In the purity test, ethanol was employed as it has a low boiling point and
high volatility hence efficient recrystallization. In the test tube containing salicylic acid and
crude Aspirin, a dark purple color was observed to indicate that the solution in those test tubes
contained a phenol group with an OH connected directly to it.
The test tube with pure Aspirin color change was not observed; hence pure Aspirin was
synthesized. Furthermore, the results formed when FTIR analysis was carried out an OH, CO
(carbonyl group) were marked by peaks in those regions.
In the preparation of Benzoic acid, 5 g of ethyl benzoate was reacted with 50 cm3 of sodium
hydroxide in hydrochloric acid as a catalyst and hence creating a conducive environment for the
reaction.
The formation of the white precipitate by the addition of hydrochloric acid indicated
the formation of benzoic acid. This product was filtrated and recrystallized to form pure benzoic
acid. To form crystals, the solution was allowed to cool at room temperature, and during
filtration, water was added to ensure the total transfer of the solution of benzoic acid.
Conclusion
This lab experiment was a success by forming Aspirin, by reacting 2.1-gram salicylic
acid by 5 ml acetic acid in the presence of concentrated sulphuric acid. Also, the preparation of
12
benzoic acid by reacting methyl benzoate with sodium hydroxide in hydrochloric presence was a
success as pure benzoic acid was reacted.
In both, 100 % yield was not observed. In the
synthesis of Aspirin, 42.17% was observed, while 66.99% yield was observed in benzoic acid
preparation. A significant reason for this discrepancy was due to transfer losses. That is, total
transfer was not a success. Also, the reflux in the preparation of benzoic acid may not have gone
to completion. Some of the Aspirin and benzoic acid may have dissolved in water. The results
were taken in rounded figures for great precision.
References
https://labmonk.com/synthesis-of-aspirin-from-salicylic-acid-using-acetic-
anhydride#:~:text=Principle%3A%20Synthesis%20of%20aspirin%20from,a
%20molecule%20of%20acetic%20acid
.
https://labmonk.com/synthesis-of-benzoic-acid-from-alkyl-benzoate
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Publisher:Cengage Learning

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