WHAT EFFECT DOES CHANGE IN REFLUX TIME

HAVE ON THE YIELD OF ACETYLSALICYLIC ACID

?
SYNTHESIS OF ASPIRIN
• Salicylic acid reacts with acetic anhydride in the presence of an acid catalyst to produce
acetylsalicylic acid and acetic acid(ethanoic acid).
• Sulfuric acid or phosphoric acid are often used to catalyze the reaction.
• Salicylic acid can react with acetic (ethanoic) acid in an esterification reaction, but the
reaction is very slow, taking days to reach equilibrium, and the yield is low : For this
reason, the commercial preparation of aspirin relies on the faster reaction between
salicylic acid and the more reactive acetic anhydride which produces a greater yield of
aspirin.

• To ensure the reaction goes as quickly as possible we heat it. To

make sure the product is not lost by evaporation we use a
reflux condenser. The hot gas produced rises up the tube and is
cooled by the running water causing the gas to condense and
return to the mixture as liquid thus saving the product.
SYNTHESIS OF ASPIRIN
METHOD
• First react acetic acid with Salicylic acid in presence of sulfuric acid
using a reflux condenser.
• Wait for 35 minutes and add ice to solution so solid can start forming.
• Repeat the step above with different time : 45 and 60 minutes.
• Then need to separate the solid from the rest of the unwanted mixture.
This can be done by pouring the entire contents of your flask through
a fluted filter.
• Then calculate the percentage yield
• https://www.birmingham.ac.uk/undergraduate/preparing-for-
university/stem/Chemistry/stem-legacy-purify-organic.aspx- VIDEO
TABLES AND GRAPHS
• Table and graph of yield of aspirin produced from different reflux time.

yeild
6
5
%
Y 4
E
3
I
2 yeild
L
D 1
0
10 20 30 40
Reflux time
CONCLUSION
• In the conclusion I will analyze the the graphs and tell at what reflux time the
highest yield was formed.
• I will describe the trend in the results of the tables and graphs and compare it
with my hypothesis.
WEBSITES
• TLC
https://schoolworkhelper.net/tlc-of-aspirin-lab-explained/
• Aspirin
https://pubchem.ncbi.nlm.nih.gov/compound/aspirin#section=2
D-Structure
• Melting point- purity
http://intro.chem.okstate.edu/ChemSource/medicine/lab1.htm
• Video
https://www.youtube.com/watch?v=hyTtGGnXu8k