Topic: Comparison of Catalysis of Aspirin Synthesis by Sulfuric Acid and Phosphoric Acid

Introduction
Aspirin is a pain-reliever and an anti-inflammatory drug. First synthesized in 1853, Aspirin continues
to be the most widely consumed drug in the world, with 50 million kilograms of it being produced
every year in the United States. It is a derivative of salicylic acid, a naturally available compound in
the bark of willow tree.
From the medicinal chemistry option in IB Chemistry, I learnt that aspirin can be synthesized with
salicylic acid and acetyl chloride in the presence of phosphoric acid. Upon further research, I found
out that catalyst is essential for a reliable yield and that the reaction can be catalyzed by other acids
too. Two of the most popular catalysts used for aspirin synthesis are sulfuric acid and phosphoric acid.
Even upon extensive research, I was unable to encounter a head-to-head comparison between the
efficiency of the two catalysts. The Chemistry Internal Assessment gave me the perfect opportunity to
curb my curiosity to compare sulfuric acid and phosphoric acid in order to find the most efficient
catalyst for synthesis of aspirin.
Research Question
Which acid catalyst (Sulfuric Acid, Phosphoric Acid) is more efficient in the synthesis of aspirin,
determined by Percentage yield and Melting point of the product?

Background Information
Catalyst
A catalyst enhances the rate of a reaction by facilitating active interaction between reactant molecules.
A catalyst may do so by lowering the activation energy of a reaction and/or forming an unstable and
reactive transition state in combination with a reactant. Although a catalyst binds to the reactant, it
does not classify as a reactant because it is regenerated at the end of a reaction, and hence is not
consumed. In acid-catalyzed reactions such as the acetylation of salicylic acid, Hydrogen ion is the
catalyst. The protonation of reactant destabilizes the reactant making it highly reactive. The reactive
transition molecule reacts to form a more stable compound, i.e. the product.1
Aspirin Synthesis
Aspirin, chemically known as acetylsalicylic acid, is synthesized by acetylation of salicylic acid.
Acetylation is the addition of an acetyl group (-COCH3) to a compound. The synthesis of aspirin is
classified as an esterification reaction. To synthesize aspirin, salicylic acid is reacted with an
acetylating agent (acetyl halide or anhydride of a carboxylic acid) in the presence of a small amount
of concentrated acid, which acts as a catalyst.2 Acetic anhydride was chosen over acetyl chloride as an
acetylating agent for this investigation upon consideration of acetyl chloride’s tendency to produce
acidic fumes by reacting with water vapor in air. This reaction yields aspirin and acetic acid,
a byproduct of the reaction.

1
IUPAC Compendium of Chemical Terminology, Electronic version,
<http://goldbook.iupac.org/C00876.html/>
2
“Synthesis of Aspirin”. Web 26 Dec 2016.
<http://www.laney.edu/wp/cheli-fossum/files/2012/01/8-Synthesis-of-Aspirin.pdf/>
1
The equation for overall reaction is shown below:

Figure 1 - General Equation for Synthesis of Aspirin

Water is added to the reaction flask to crystallize aspirin and quench the reaction. Acetic
anhydride reacts with water to form acetic acid. Acetic acid can be easily separated from aspirin by
vacuum filtration since acetic acid is highly soluble in water. The aspirin isolated in this step is the
“crude product”. The percentage yield will be determined for the crude product obtained in this
reaction.
Mechanism of Acetylation
In reality, acetylation of salicylic acid is a multi-step reversible reaction during which the
catalyst acts to increase the rate of reaction. The detailed mechanism is provided below:

Figure 2 - Mechanism of acetylation of salicylic acid

As shown above, the mechanism involves bonding of acetic anhydride to the hydroxyl group of
salicylic acid. The protonation of the reactant molecules in step 1 and step 4 leads to the splitting of
the anhydride into two acetyl groups to form acetylsalicylic acid and acetic acid. Protonation of
molecules makes them more reactive. Since the protonation is only a part of the forward reaction in
step 1 and step 4, only the forward reaction is catalyzed and the equilibrium shifts to the right, giving
higher yield of the product.3

3
“Synthesis of Esters”. Web 23 Feb 2017.
<http://www.chem.ucalgary.ca/courses/350/mechanistic_etext/Ch15/ch15-4-5.html/>
2
The hydrolysis of acetic anhydride in step 5 is highly exothermic, but happens very slowly at room
temperature, so there is no observable temperature change.4 On adding the catalyst, the reaction will
be faster, so the temperature change should be fast enough to be observed using a thermometer. The
rate of this temperature rise can be used to model and compare the rate of reaction. The time taken for
a temperature change of 5°C was measure in this experiment.
Salicylic acid is a white powdered solid, and is insoluble in acetic anhydride, which is a colorless
liquid. The disappearance of the white powder would indicate the complete reaction of salicylic acid
with acetic anhydride. Post incubation in the water bath, the reaction mixture was checked for white
powder to determine the presence of unreacted salicylic acid.
Determination of Purity using Melting Point
The temperature at which a solid exists in equilibrium with its liquid state is the melting point of the
solid. It is an intrinsic physical property for each substance. Since aspirin is a crystalline solid, its
melting point can be used to assess its purity. An impure crystal melts at a lower temperature than its
pure counterpart. The lower melting point is a result of the disturbances in the crystalline lattice of the
compound due to the presence of impurities. In a pure crystalline solid, the molecules, which are
congruent, are arranged in an orderly and closely packed manner. In this arrangement, the molecules
experience maximum intermolecular forces and hence have the highest melting point. The introduction
of a foreign molecule, however, breaks the lattice, causing a decrease in the intermolecular forces
because the molecules are now present farther apart from each other.5 The same is illustrated in the
images below using the analogy of a brick wall and a football.

Figure 3 - Comparison of a pure and impure crystalline lattice structure using analogy of a brick wall

Pure aspirin melts at 135°C.6 As the concentration of impurity increases, the melting point decreases.
Therefore, a lower melting point will mean higher concentration of impurities.
Purity can also be determined through recrystallization where the product is dissolved in ethanol by
heating and then cooled to remove salicylic acid, which is soluble in ethanol. This method assumes
that all the impurities are soluble in ethanol, which may not be the case. Also, aspirin is soluble in
ethanol at 0.03 g/cm3. The loss of mass is significant considering that the theoretical yield itself is 2.60
g, as calculated further in this report. So, due to the high magnitude of error, melting point was chosen
to determine purity over recrystallization.

4
“Acetylation of a Hydroxyl Group”. Web 22 Feb 2017. 6
<http://www.sciencemadness.org/talk/files.php?pid=283075&aid=23357/>
5
“Use of Melting Point Apparatus”. Web. 09 Feb 2016.
<https://www.chm.uri.edu/mmcgregor/chm228/use_of_melting_point_apparatus.pdf/>
6
“Acetyl-salicylic acid”. Web. 26 Mar 2016. <https://pubchem.ncbi.nlm.nih.gov/compound/aspirin#section=Melting-
Point/>
3
Hypothesis
Percentage Yield of Aspirin: Sulfuric Acid will give a higher percentage yield than Phosphoric Acid
because it is a stronger acid, and hence has higher protonating potential. This is because, as explained
in the Background Information, protonation, the catalytic step, takes place twice during the acetylation
of salicylic acid.
Purity of Aspirin: Aspirin synthesized using phosphoric acid will be purer than aspirin synthesized
using sulfuric acid. This is because sulfuric acid is highly corrosive which might lead to secondary
reactions and subsequent formation of byproducts.7 Phosphoric Acid, on the other hand, is minimally
reactive compared to Sulfuric Acid, and hence does not form byproducts.

Variables
Independent Variable: Catalyst
- Sulfuric acid
- Phosphoric acid
Although both the catalysts are acids and catalyze the reaction through the same mechanism. They
have different strength as acids and different reactivity.
Dependent Variable: Percentage yield (%) and Melting Point (°C) of the Aspirin product
Controlled Variables:
Variable Effect of the variable Method of Control
Amount of Catalyst Amount of Catalyst is 5 drops of each acid catalyst at
positively correlated to the equal concentrations of 85%
increment in rate. (vol.) were measured using a
dropper.
Amount of reactants – Mass of Amount of reactants is Using a weight balance, equal
salicylic acid and Volume of proportional to the yield of the masses of 2g salicylic acid
acetic anhydride product. In case of a solid, it were weighed in a beaker.
also affects the concentration Identical pipette was used to
of reactants in the reaction transfer 5 ml of Acetic
mixture, and hence affects the anhydride to each trial setup.
rate of reaction.
Temperature of the water bath Temperature affects the The temperature of the water
kinetics of the reactants and bath was maintained at 80°C
hence the rate of the reaction. using a thermostat.
Time period of incubation in The duration of incubation is The duration of incubation was
the water bath proportional to the energy controlled using a stopwatch to
given to the reactants. 10 minutes for each trial.

7
"The Power of Acid Catalysis." Master Organic Chemistry RSS. Web. 09 Mar. 2016.
<http://www.masterorganicchemistry.com/2010/04/21/the-power-of-acid-catalysis/>.
4
Safety, Ethical, and Environmental Considerations
Concerns: Salicylic Acid irritates skin and eyes on contact. Acetic anhydride is corrosive flammable.
It is volatile and forms toxic fumes in the air. Sulfuric Acid and Phosphoric Acid and extremely
corrosive. Acetic anhydride and Sulfuric acid react violently with water. Acids and acetic anhydride
react violently with water.

Precautions: Gloves, chemical vapor resistant mask, goggles, apron were worn throughout the
experiment. The experiment was conducted in a corner in a well ventilated area next to an exhaust fan
to prevent stagnation and accumulation of fumes, and also avoid chemical exposure to fellow students.
The heating was done using a water bath to avoid contact with fire. The reaction flask was covered
with Aluminum foil to contain the acetic anhydride fumes. A heap of sand was kept ready close to the
experimental setup in case of chemical spillage to prevent the spread of harmful chemicals (acids,
acetic anhydride). Also acids and acetic anhydride were stored away from water in tightly closed
volumetric flasks. The resulting chemicals (aspirin and acetic acid) are harmless and hence disposed
into a sealed common chemical disposal container after the experiment. The concentrated acid
leftovers were diluted and then neutralized with Sodium hydroxide and tested with litmus paper before
disposing the same way as the other chemicals.

Method
Apparatus
Apparatus Quantity Apparatus Quantity
50 cm3 Beaker 3 Aspirator 1
10 cm3 Pipette 1 Bunsen burner 1
Thiele tube 1 Ice Bath 1
Oil 50 cm3 Filter Paper 6
50 cm3 Graduated Cylinder 1 Digital Weight Balance 1
(±0.01 g)
Buchner Flask 1 Thermometer (±0.5 °C) 2
Aluminum foil 1 Pack Dropper 1
Buchner Funnel 1 String 1 roll
Desiccator 1 Clamp Stand 1
Chemicals
Chemical Quantity Chemical Quantity
Salicylic Acid 15 g Distilled Water 100 cm3
Acetic anhydride 40 cm3 Crushed Ice Half a 500 cm3
beaker
Phosphoric Acid 10 cm3 Sulfuric Acid 10 cm3

5
Procedure
The Procedure was referenced from an organic chemistry laboratory manual8, with some changes
being made to match the apparatus and chemicals available in the school laboratory.
Synthesis of Aspirin
1. 5.0 cm3 of acetic anhydride was transferred to a 100 cm3 beaker using a pipette. 10 drops of
acid (catalyst) were added to the flask.
2. 2.00 g of salicylic acid was weighed on a weigh paper and subsequently transferred to the
beaker. The mixture was stirred by swirling the beaker.
3. A stopwatch was started immediately and time taken for temperature rise of 5°C was recorded.
4. Following this, the beaker was incubated in the hot water bath at 80°C for 10 more minutes.
5. The beaker was taken out of the water bath followed by addition of 10 cm3 of distilled water.
The beaker cooled to room temperature. The beaker was placed in an ice bath to completely
crystalize aspirin.
6. The weight of a filter paper was recorded using a
weight balance.
7. A Buchner funnel with the filter paper was placed in
Buchner flask (as shown on the right) and moistened
with distilled water from a squirt bottle. The aspirin
slurry was transferred into the funnel and vacuum
filtered using an aspirator for 5 mins. The crystals
obtained were washed with cold distilled water.
8. The watch glass with aspirin was placed overnight in a
desiccator.
9. The watch glass along with the filter paper and the
aspirin was weighed on a weight balance.
10. The procedure was repeated for 3 trials with sulfuric
acid and phosphoric acid each. Figure 4 - Vacuum Filtration set up

Melting Point Analysis

1. A capillary tube was sealed on one end by heating on a Bunsen
burner flame and cooled.
2. It was then filled with powdered aspirin to form a 1 cm column
of aspirin crystals by tapping the open end against the aspirin.
3. The capillary tube was then attached to the bulb of a
thermometer using a string.
4. The thermometer bulb was lowered into a Thiele tube and set
up as shown on the right.
5. The oil was heated rapidly using a Bunsen burner until the oil
reached 120°C, after which the flame was lowered and the
heating was continued at a rate no higher than 2°C per minute.
6. The temperature at which the crystals begin to melt was
recorded as the melting point of the aspirin sample.
Figure 5 - Melting point
7. The procedure was repeated for 3 trials with sulfuric acid and apparatus set up
phosphoric acid each.

8
Ross, T., Sevenair, J., Organic Chemistry Laboratroy Manual, 6th Ed; Wiley Custom: Hoboken NJ, 2006, p 94-96
6
Data Collection
Table 1 - Mass of Filter Paper pre and post Vacuum Filtration

Catalyst Used
Mass of Filter
Paper/g ±0.01 Sulfuric Acid Phosphoric Acid
Trial 1 Trial 2 Trial 3 Trial 1 Trial 2 Trial 3
Initial Mass 0.78 0.88 0.81 0.82 0.86 0.89
Final Mass 3.01 3.29 3.13 2.54 2.6 2.77
Difference 2.23 2.41 2.32 1.72 1.74 1.88
Initial Mass – The mass of plain filter prior to vacuum filtration
Final Mass – The mass of filter paper post vacuum filtration. This is the combined mass of filter
paper and aspirin residue.
Difference – Mass of Aspirin produced. The mass could also have been calculated by scraping the
crystals off the filter paper but this causes a great error since the grainy, irregular texture of the filter
paper disallows complete extraction of the crystals by scraping.
Table 2 - Data of reaction catalyzed by Sulfuric acid
Trial Number Time taken for 5°C Mass of Aspirin Melting Point of
temperature rise/s ±0.3 Produced/g ±0.02 Aspirin/°C ±1

Trial 1 9.2 2.23 123

Trial 2 13.1 2.41 126
Trial 3 12.4 2.32 127
Table 3 - Data of reaction catalyzed by Phosphoric acid
Trial Number Time taken for 5°C Mass of Aspirin Melting Point of
temperature rise/s ±0.3 Produced/g ±0.02 Aspirin/°C ±1

Trial 1 23.7 1.72 130

Trial 2 20.0 1.74 129
Trial 3 21.2 1.88 133

Uncertainties: Mass of Aspirin was calculated by subtracting the mass filter paper after vacuum
filtration (with aspirin) from the mass of plain filter paper before vacuum filtration (without aspirin).
The uncertainty of the mass (±0.02) is a sum of uncertainties of initial mass and final mass from Table
2 used to calculate the mass of the product. The absolute uncertainty of time taken for temperature rise
in is equal to my average reaction time, which affects the starting and stopping of the stopwatch. The
uncertainties of Mass and Melting point of aspirin follow the respective uncertainties of the weight
balance and the thermometer.
Qualitative Observations: At the end of the 10 minute incubation period, the reaction mixture was a
colorless liquid with no trace of any solid, including the white, powdered salicylic acid. During the
incubation, the salicylic acid in the sulfuric acid catalyzed reaction disappeared faster (at around the 7
minute mark) than in the reaction catalyzed by phosphoric acid, in which the salicylic acid disappeared
around the 9 minute mark.

7
Data Processing
Percentage Yield of Aspirin

Table 4 - Percentage Yield of Aspirin

Percentage Yield
Catalyst
Trial 1 Trial 2 Trial 3
Sulfuric Acid 85.8 92.7 89.2
Phosphoric Acid 66.2 67.0 72.3

The percentage yield was calculated using the following equation:

𝑬𝒙𝒑𝒆𝒓𝒊𝒎𝒆𝒏𝒕𝒂𝒍 𝒀𝒊𝒆𝒍𝒅
𝑷𝒆𝒓𝒄𝒆𝒏𝒕𝒂𝒈𝒆 𝒀𝒊𝒆𝒍𝒅 = ∗ 𝟏𝟎𝟎
𝑻𝒉𝒆𝒐𝒓𝒆𝒕𝒊𝒄𝒂𝒍 𝒀𝒊𝒆𝒍𝒅

The theoretical yield of aspirin was calculated by considering the 2g of salicylic acid as the limiting
reagent, since excess acetic anhydride was used in the reaction.
C7H6O3 + C4H6O3  C9H8O4 + C2H4O2
From the equation, it can be deduced that the mole ratio of salicylic acid and aspirin is 1:1. 1 mole of
salicylic should theoretically produce 1 mole aspirin, because the limiting reagent is salicylic acid.
Molar mass of salicylic acid = 138.13 g
Molar mass of aspirin = 180.17 g
𝑀𝑎𝑠𝑠 𝑜𝑓 𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑
Number of moles of salicylic acid used =
𝑀𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑
2.00
=
138.13
= 0.0144 moles
Theoretical yield of Aspirin (g) = No. of moles of aspirin * Molar mass of aspirin
= 0.0144 * 180.17
= 2.60 g
Sample Calculation using Trial 1 of Sulfuric acid:
𝟐.𝟐𝟑
𝑷𝒆𝒓𝒄𝒆𝒏𝒕𝒂𝒈𝒆 𝒀𝒊𝒆𝒍𝒅 = 𝟐.𝟔𝟎 ∗ 100
𝑷𝒆𝒓𝒄𝒆𝒏𝒕𝒂𝒈𝒆 𝒀𝒊𝒆𝒍𝒅 = 85.8 %
Comparison of catalysts
Table 5 - Comparison of catalysis by Sulfuric Acid and Phosphoric Acid
Catalyst
Sulfuric acid Phosphoric acid
Type of Data
Random Random
Average Uncertainty Average Uncertainty
Time taken for 5°C
temperature rise/s 11.6 2.0 21.6 1.9
Percentage Yield/%
89.2 3.5 68.5 3.1
Melting Point of Aspirin/°C
125 2 131 2
8
Average
The average for the three data values for each set was calculated using the following equation:
(𝒂𝟏 + 𝒂𝟐 +. . . 𝒂𝒏 )
𝑨𝒗𝒆𝒓𝒂𝒈𝒆 =
𝒏
For this investigation, the value of n was 3 because three trials were conducted for each data set.
Sample Calculation for average melting point of Sulfuric Acid:
(𝟏𝟐𝟑 + 𝟏𝟐𝟔 + 𝟏𝟐𝟕)
𝑨𝒗𝒆𝒓𝒂𝒈𝒆 =
𝟑
𝑨𝒗𝒆𝒓𝒂𝒈𝒆 = 𝟏𝟐𝟓 °𝑪
Propagation of Uncertainties

The random uncertainty for mean was calculated as half of the range of data values obtained.
(𝑴𝒂𝒙𝒊𝒎𝒖𝒎 𝑽𝒂𝒍𝒖𝒆 − 𝑴𝒊𝒏𝒊𝒎𝒖𝒎 𝑽𝒂𝒍𝒖𝒆)
𝑹𝒂𝒏𝒅𝒐𝒎 𝑼𝒏𝒄𝒆𝒓𝒕𝒂𝒊𝒏𝒕𝒚 =
𝟐
Sample Calculation for Random Uncertainty of Sulfuric Acid:
(𝟖𝟐. 𝟕 − 𝟕𝟕. 𝟖)
𝑹𝒂𝒏𝒅𝒐𝒎 𝑼𝒏𝒄𝒆𝒓𝒕𝒂𝒊𝒏𝒕𝒚 =
𝟐
𝑹𝒂𝒏𝒅𝒐𝒎 𝑼𝒏𝒄𝒆𝒓𝒕𝒂𝒊𝒏𝒕𝒚 = 𝟐. 𝟓
The same method of calculation for all the random uncertainties in this investigation.
Graphical Representation of Data
Graph 1 - Time taken for the temperature of reaction mixture to rise by 5°C
In can be observed in
Time taken for temperature rise of reaction Table 5 and Graph 1,
sulfuric acid catalyzed
mixture by 5°C
reaction takes less time
25.0 than the phosphoric
Time taken for temperature rise of

acid catalyzed reaction

20.0
reaction mixture by 5°C/s

for a temperature
increase of 5°C. Since
15.0
acetylation of salicylic
10.0 acid is an exothermic
reaction, this means
5.0 that the reaction
catalyzed by sulfuric
0.0 acid was faster than the
Reaction catalyzed by Sulfuric acid Reaction catalyzed by Phosphoric acid
reaction catalyzed by
phosphoric acid.
Also, the faster disappearance of salicylic acid in the sulfuric acid catalyzed reaction means that
salicylic acid reacts faster in the presence of sulfuric acid compared to phosphoric acid. This credits
the assertion that sulfuric acid provides a faster rate of reaction.

9
Graph 2 - Percentage Yield of Aspirin synthesized using each catalyst
According to Table 5
Percentage Yield and Graph 2, sulfuric
acid catalyzed
100.0
89.2
synthesis of aspirin has
80.0 approximately 20%
Percentage Yield

68.5 greater percentage

60.0 yield than that of
phosphoric acid
40.0
catalyzed reaction.
20.0 Thus, sulfuric acid
catalysis produces 20%
0.0 more crude aspirin than
Reaction catalyzed by Sulfuric acid phosphoric acid
Reaction catalyzed by Phosphoric acid
catalysis.

Graph 3 - Melting Point of Aspirin synthesized using each catalyst

Based on Table 5 and
Melting Point Analysis Graph 3, aspirin
140
produced with sulfuric
Acid has a lower
135 melting point than the
Melting Point/°C ±1

aspirin formed with

130
phosphoric acid. Since
125 the deviation from the
melting point is
120 proportional to the
115
concentration of
impurities, sulfuric
110 acid catalyzed aspirin
Pure Aspirin
is less pure than
Synthesised using Sulfuric acid
phosphoric acid
Synthesised using Phosphoric acid
catalyzed aspirin.
The random error of the all the plotted data (although visibly existent) does not falsify the comparison
between the two catalysts. Since there is no overlap in the error bars in any of the graphs above, the
difference in the data gathered for sulfuric acid and phosphoric acid is considered to be statistically
significant.

Conclusion
The scientific explanation for the observations in the data analysis will be provided in this section.
Sulfuric acid is much stronger than phosphoric acid. So, sulfuric acid produces more hydrogen ions
than phosphoric acid at equimolar concentrations. Since, hydrogen ion is the catalytic molecule, its
concentration is proportional to the rate of reaction. Therefore, the rate of reaction is faster with sulfuric
acid than with phosphoric acid.
The percentage yield with the two catalysts can be explained using the effect of the catalyst in shifting
the equilibrium of the reaction. Organic synthesis reactions like synthesis of aspirin are reversible and
do not go to completion.9 The hydrogen ions catalyze the reaction by protonating the salicylic acid.
Protonation makes the salicylic acid more reactive, hence shifting the equilibrium to the right.

9
Schobert, Harold H., The Chemistry of Hydrocarbon Fuels; Butterworth-Heinemann, 2013. 4
10
Therefore, the concentration of hydrogen ions is positively correlated to the percentage yield, which is
why sulfuric acid has a higher percentage yield than phosphoric acid.
The lower melting point of sulfuric acid catalyzed aspirin is due to higher concentration of impurities.
More impurities cause more breaks in the crystalline lattice allowing for weaker intermolecular forces.
The higher concentration of impurities can be
attributed to the reactivity of the sulfate ion (SO42-).
Concentrated sulfuric acid is also a weak oxidizing
agent. Thus, using sulfuric acid can lead to unwanted
side reactions.10 In the synthesis of aspirin, sulfate ion
can oxidize salicylic acid to form sulfo-salicylic acid,
which is shown on the right. Phosphoric Acid, however Figure 6 - Sulfonation of Salicylic acid
is weak and does not oxidize any of the reactants. But the lower melting point of the sample compared
to that of pure aspirin can be due the presence of unreacted salicylic acid, since, as explained above,
the acetylation of salicylic acid does not go to completion.
The aim of this investigation was to identify the more efficient catalyst between sulfuric acid and
phosphoric acid. Efficiency does not only include the amount of product formed but also the magnitude
of resources (including reactants, time, and reaction conditions) that are needed to make the product.
The results were in conformation with hypotheses for percentage yield and purity of the product. It can
be concluded that sulfuric acid is the most efficient catalyst because it provides greater yield of crude
product and a faster rate of reaction, which means a greater amount of product can be formed in a
smaller amount of time than with phosphoric acid. Also, since the difference in melting point (6°C) of
the aspirin produced by sulfuric acid and phosphoric acid is not every large, the difference in purity of
the two samples in not significantly large. Also, the, the presence is not a huge concern because the
aspirin has to undergo intense purification either way because of the stringent purity requirements for
a drug.

Evaluation
Weaknesses:
Error Impact on Experiment Corrective Measures

Melting point analysis as an Uneven distribution of The melting point can be tested
assessment of purity assumes impurities, which is commonly multiple times by collecting crystals
that impurities are evenly the case, gives an erroneous from different parts of the sample
distributed throughout the melting point for the product and the average can be calculated for
product an accurate melting point.
Salicylic acid is not completely On cooling the reaction Ethanol can be used to crystallize
soluble in water. mixture in step 4 of aspirin aspirin, because both salicylic acid
synthesis, unreacted salicylic and acetic acid are soluble in
acid also crystallizes along ethanol. If ethanol is used, the
with aspirin. reaction mixture need to be cooled
before adding ethanol and the
experiment should be conducted in a
closed chamber or a fume hood
because of high volatility of ethanol.

10
"The Power of Acid Catalysis." Master Organic Chemistry RSS. Web. 09 Mar. 2016.
<http://www.masterorganicchemistry.com/2010/04/21/the-power-of-acid-catalysis/>.
11
Strengths:
Corrective Measures Impact on Experiment

3 factors of catalyzed reaction (rate of reaction, Multiple factors of analysis provide a wider base
percentage yield, purity of the product) to compare of comparison and a more conclusive result based
the efficiency of the two catalysts (sulfuric acid, on not one but multiple, varied factors
phosphoric acid)
Textbooks, journals and lab manuals were the main Textbooks, journals and well referenced lab
source of information cited in this report. manuals are more credible and more accurate than
websites because the authors of these sources are
experts in the area of concern.

Extended Research
1. The investigation could have be extended to include other acids, with a wide range of pH, as
catalysts. Similarly, bases could also be investigated for their catalytic efficiency. The
catalysts could be tested and compared at different concentrations in order to determine the
most efficient catalyst and model an efficient reaction with minimum byproducts.
2. The time period of heating and the temperature of the reaction can be changed to measure the
impact of these factors, especially in case of weak acids where the reaction is slow and may
have high yield for longer reaction times.
3. A comparison can also be done for yields and purity with different reactants. For instance, the
yield of aspirin with acetyl chloride and acetic anhydride can be compared.

Bibliography
“Acetyl-salicylic acid”. Web. 26 Mar 2016.
<https://pubchem.ncbi.nlm.nih.gov/compound/aspirin#section=Melting-Point/>
“Acetylation of a Hydroxyl Group”. Web 22 Feb 2017. 6
<http://www.sciencemadness.org/talk/files.php?pid=283075&aid=23357/>
Ross, T., Sevenair, J., Organic Chemistry Laboratroy Manual, 6th Ed; Wiley Custom:
Hoboken NJ, 2006, 94-96
IUPAC Compendium of Chemical Terminology, Electronic version,
<http://goldbook.iupac.org/C00876.html/>
Schobert, Harold H., The Chemistry of Hydrocarbon Fuels; Butterworth-Heinemann, 2013. 4
“Synthesis of Esters”. Web 23 Feb 2017.
<http://www.chem.ucalgary.ca/courses/350/mechanistic_etext/Ch15/ch15-4-5.html/>
“Synthesis of Aspirin”. Web 26 Dec 2016,
<http://www.laney.edu/wp/cheli-fossum/files/2012/01/8-Synthesis-of-Aspirin.pdf/>
"The Power of Acid Catalysis." Master Organic Chemistry RSS. Web. 09 Mar. 2016.
<http://www.masterorganicchemistry.com/2010/04/21/the-power-of-acid-catalysis/>.
“Use of Melting Point Apparatus”. Web. 09 Feb 2016.
<https://www.chm.uri.edu/mmcgregor/chm228/use_of_melting_point_apparatus.pdf>

12