Escolar Documentos
Profissional Documentos
Cultura Documentos
Synthesis of Aspirin
Salicylic acid
Filter Paper
Acetic anhydride
Crude aspirin generated + Filter Paper
Table 2. Physical Observations
Compound
Observations
White fine powder with few bulk
particles
White crystals
Salicylic acid
Crude aspirin generated
II.
1.4383 g
Filter paper
0.6539 g
1.7687 g
Recrystallized Aspirin
1.1148 g
100 =77.51
1.4383 g
% Recovery
Observations
White fine crystals
Percentage Yield
Yield
100 %
( Experimental
Theoretical Yield )
Yield=
Theoretical Yield
2.1020 g
Since mol Salicylic acid < mol Acetic anhydride, Salicylic acid is the limiting reagent.
Balanced Reaction:
C7H6O3 + C4H6O3
C9H8O4 + C2H4O2
Salicylic
Acid
Aspirin
Therefore, the mole ratio between Salicylic acid and Aspirin is 1:1.
1 mol Aspirin
180.17 g Aspirin
=2.7286 g Aspirin
1mol Salicylic acid
1 mol Aspirin
mass
(Filter Paper)
100 % = 61.51%
(1.6844g
2.7386g )
recrystallied Aspirin
( mass ofTheoretecal
) 100
yield
%Yield=
mass
= Experimental Yield
1.1148 g
100 =40.8 6
( 2.7286
g)
%Yield=
Discussion
Synthesis of Aspirin
Acetylsalicylic acid or aspirin was obtained by a modified esterification
reaction. Esterification reaction is the reaction between a carboxylic acid and
an alcohol to prepare a compound containing an ester functional group and
water as a by-product. In synthesizing aspirin, an acid anhydride, acetic
anhydride, was used instead of carboxylic acid (e.g. acetic acid). This is
because esterification with acetic acid is unfavourable.
the limiting reagent and therefore, the acetic anhydride is added in excess.
After heating, there might still be unreacted acetic anhydride. Water will
react with the excess acetic anhydride to form acetic acid. 10 grams of
crushed ice is then added to the flask. This is crucial to separate aspirin from
other by-products of the reaction. Aspirin is slightly soluble in cold water
causing it to precipitate in cold environment. The precipitated aspirin was
collected by vacuum filtration. Acetic acid, Sulfuric acid and all other soluble
materials were passed though the filter paper.
The aspirin generated was weighed. The numerical data is summarized
on table 1. On table 2, physical differences are cited between salicylic acid
and the crude aspirin. Percentage yield for the crude aspirin was calculated:
61.51%. This percentage suggests a lower yield for pure aspirin. However, it
is still reasonable noting the flaws of the procedure itself. It is possible that
some of the yield didnt precipitated and were washed through the filtration
process. Other errors must be of mishandling and of personal errors.
Recrystallization
The aspirin collected from the first part of the experiment still needs
further purifying. The aspirin obtained might still contain contaminations
such as unreacted starting materials and unwanted products from sidereactions. The main impurity in the crude aspirin is salicylic acid which may
be the product of the hydrolysis of the product during isolation steps.
Recrystallization was the technique used in the experiment. A large fraction
of the crude aspirin was used in recrystallization. The small fraction was
saved for melting point determination in part 3. Recrystallization involves the
dissolution of a solid in a pre-selected solvent at an elevated temperature
thereby re-forming crystals upon cooling, leaving the impurities to
remain in solution to be filtered. The solvent used to dissolve the crude
aspirin was ethanol. Ethanol dissolves the aspirin and the impurities as
ethanol and all the compounds are polar (like dissolve like). 10 ml of water
was added, again, to react with the unreacted acetic anhydride and to
gradually cool down the solution. It is then heated to assure the dissolution
of the solid. After, it was cooled in an ice bath until crystals are formed.
Cooling will precipitate the pure aspirin and leave the soluble impurities to be
passed through the filter paper. The recrystallized aspirin is separated from
its impurities by suction filtration.
The data obtained in recrystallization is summarized on table 3. The
percentage recovery was 77.51% which is considered as an accepted
References
Zubrik, James W. 1997. The Organic Chem Lab Survival Manual: A Student's Guide to
Techniques. 4th ed. John Wiley & Sons.
McMurry, R.S. 2008. 7TH Ed. Organic Chemistry. USA: Prentice Hall, 332-345.
Pavia, Donald L. 2005. Introduction to Organic Laboratory Techniques: A Small Scale
Approach. USA: Brooks/Cole, 55-57.