Umar Mohammed

7767461
Laboratory Section: B04
Rotation: 2
Room Number: 216
Locker Number: 1377
Experiment 2: Synthesis and Analysis of Acetylsalicylic Acid
Date of Experiment: Thursday January 29, 2015
Time of Experiment: 8:30 AM
Date Submitted: Monday February 2, 2015

Purpose
The purpose of this experiment is to synthesize acetylsalicylic acid (ASA, Aspirin )
and then compare the purity of the synthesized ASA with commercially made ASA utilizing
colourimetry and the differences in melting points.
The hypothesis made is that the synthesized ASA will have very little difference of
purity when compared to the commercial ASA after conducting the required tests.
Calculations: Percent Yield of ASA
Mass of Product ASA
Molar Mass of ASA
Volume of measured Acetic Anhydride
Density of Acetic Anhydride
Molar Mass of Acetic Anhydride
Mass of measured Salicylic Acid
Molar Mass of Salicylic Acid

2.17 g
180.157 g/mol
5.0 mL
1.08 g/mL
102.09 g/mol
1.991 g
138.121 g/mol

# 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

Utilizing the balanced equation above and stoichiometry the limiting regent must be
acquired before the number of moles of ASA can be determined theoretically. However because
there is a 1:1 ratio between each of the products and ASA, the # of moles of the products can be
directly converted into moles of ASA
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 placed within the ice bath, the reaction took a while to undergo requiring the
use of a glass rod to catalyze the reaction, however some mass was stuck onto the glass rod
resulting in a loss of mass, 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.

However these results are justified due to the reason of the synthesized ASA being
contaminated with other compounds such as Salicylic Acid. The reason the melting point range
is wider is because of it containing more Salicylic Acid than normal which means that there is
more Salicylic Acid required to melt than normal as well. The reason for the lower melting
point is because of ASA being less pure it contains weaker bonds where ASA molecules are
bonded to other impurities as opposed to pure ASA.
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. The small amount of Salicylic acid is
required within commercially made ASA as it is toxic to humans thus ruining the purpose of
ASA for human benefit.
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. It took a
considerably amount of time to cool down the melting point apparatus and if there was more
time, to allow both the capillary tube and thermometer to come about to the same temperature
then there could potentially have been a difference in measurement in melting point range.
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

References
1. Lab Manual
Kocxzanski,Krystyna; Xidos, James D. CHEM 1310 Laboratory Manual ; UMSU Copy Centre:
Winnipeg, MB, Canada , 2015 , pp 47-59
2. Table in online handbook
Laboratory Solvents and Other Liquid Reagents, in CRC Handbook of Chemistry and Physics,
95th ed. (Internet version 2014), Haynes, W.A., Ed.; CRC press: Boco Raton, FL.
http://www.hbcpnetbase.com/ (accessed Feb 1, 2015)