Purpose

The purpose of this experiment is to synthesize acetylsalicylic acid

(ASA, Aspirin TM) and then compare the purity of the synthesized
ASA with commercially made ASA.

Calculations:PercentYieldofASA
# of moles of Salicylic Acid= Mass of Salicylic Acid / Molar Mass of
Salicylic Acid = 1.991/138.121= 0.014 mol of Salicylic Acid
Mass of Acetic Anhydride= (Density of Acetic Anhydride) (Volume of
measured Acetic Anhydride) = (1.08) (5)= 5.4g of Acetic Anhydride
# of moles of Acetic Anhydride= Mass of Acetic Anhydride / Molar
Mass of Acetic Anhydride = 5.4 / 102.09= 0.053 moles of Acetic
Anhydride

C7H6O3 + C4H6O3 > C9H8O4 + C2H4O2

0.014 mol Salicylic Acid = 0.014 mol ASA 0.053 mol Acetic Anhydride
= 0.053 mol ASA
Therefore, Salicylic Acid is the limiting regent within the reaction and
the mass of ASA can now be determined.
Mass of ASA= (# of moles of ASA) (Molar mass of ASA) = (0.014)
(180.157)= 2.52 grams of ASA
Percent Yield= Actual Yield of ASA / Theoretical Yield of ASA =
2.17/2.52= 0.86(100)= 86% of ASA recovered

Discussion
Depending on the measurements taken of each compound used for the
reaction of ASA are linked to the quantitative values as depending on
how much Salicylic Acid was used would have affected the results of
ASA produced because Salicylic Acid is the limiting regent. The
accuracy of measurements would be determined to be close to the
theoretical yield as there was 86% of ASA recovered through the
measurements, although it is not the ideal 2.52 grams of ASA, other
sources of error could have affected these results.
The sources of error that could have occurred, would mostly have
occurred during measurements, calculations and transferring of
materials. Examples of errors within calculations and measurements
would have occurred with the measuring of the compounds such as
Salicylic Acid and due to the sensitivity of the balance, if it was not tared
properly the measurement of the Salicylic Acid would be off by a few
grams, and a small difference in grams could have affected the
calculations of the ASA produced. The other largest source of error
would have likely occurred during the transferring of all the materials.
Losing some material has a great effect on the percent yield as the
number of grams of ASA is greatly involved within those calculations.
When transferring from the Buchner funnel vacuum filtration setup
some of the ASA was stuck the sides of the filtration funnel and also
stuck to the filtration paper thus more mass was lost.
The purity of the ASA product produced after conducting the USP and
melting point tests results in a very impure ASA product. After creating a
vial of the ASA product and adding Iron (III) Chloride to the vial, the
color of the solution within the vial turned into a very deep purple,
which closely matched the laboratory made examples of 1.0% salicylic
acid being present within the ASA produced giving a visual
representation of how impure the ASA product is. When compared to
commercially made ASA, which had a 0.15% impurity is another
example of how impure the ASA product synthesized really is. From
conducting the melting point test, after putting ASA within the capillary

tube and into the melting point apparatus the change in state of ASA
occurred at 199 C and finished changing state at 125 C which is a very
big difference when compared to the actual melting point range of ASA
which is 138 140 C.
The purity of ASA synthesized within this lab when compared to the
commercially made ASA is greatly different as the ASA synthesized
when utilizing colourimetry the ASA synthesized had a very deep purple
color and this resulted in an estimation of 1.0% salicylic acid being
present within the ASA. When compared to the commercially made ASA
which had only 0.15% after estimation as it had a light brown color.
Throughout this experiment there are small changes that could greatly
affect the result of quality and quantity of the ASA synthesized. One
example of these changes would be using the analytic balance as
opposed to the other balances as the analytic balance would provide the
most accurate results in terms of measuring the grams of Salicylic Acid,
and because of how greatly the amount of Salicylic Acid affects the
purity of ASA and production of ASA as well this change would prove
very useful. To improve the quantity of ASA recovered, more
carefulness of transferring the materials between instruments should be
taken into consideration as a loss of product between instruments can
greatly affect the amount of ASA recovered throughout the process.
Another change that could have affected results would have to occur
when using the melting point apparatus, because the thermometer and
capillary tube are made of different materials thus the heat capacity of
each would be different, but however due to time constraints not enough
calibration was taken into consideration when conducting this test.

Conclusion
Although the initial hypothesis was not proven as there was a
considerable 14% difference between the actual yield and the theoretical
yield, this experiment has been proven to be a success as ASA was

successfully synthesized with having 86% percent yield when compared

to the actually although the quality was not the purest by having a 1.0%
estimation of Salicylic Acid contamination and a melting point of 119 C
125C, the ASA was easy to compare with the commercial ASA.