Marougail Morris Phillips Finalpaper

Marougail - Morris - Phillips
Introduction
Headaches, back pains, sore legs, risk of a serious heart attackthe list of
health issues and pains people have today seems never ending. To alleviate some of
the pain, people often pop one or two aspirin into their mouth. Although countless
people consume aspirin each day, most are oblivious to the tedious process and the
active ingredients that are behind the production of this drug. Aspirin may seem like a
simple drug, but the complex process behind it is unknown to many.
The purpose of this experiment was to synthesize aspirin and then analyze two
of aspirins intensive properties: melting point and absorbance. Melting point and
absorbance are intensive properties of aspirin because they do not depend on the
amount of matter present. The experiment also calculated the percent yield of
synthesized aspirin. Percent yield is considered to be an extensive property because
the amount of matter present does have an effect on the results.
To accomplish this research experiment, aspirin was first produced by mixing
salicylic acid and distilled water. The solution was then heated using a hot plate, filtered
using a Bchner funnel, and set aside to crystallize into a powder-like substance. After
the aspirin crystallized, a portion of it was melted using a Melt Station to determine its
melting point range. Another sample was examined using a spectrometer to determine
its absorbance. The percent yield of each synthesized aspirin batch was then calculated
using the determined absorbance along with multiple mathematical calculations.
The results of this experiment can be applied to the lives of common people as
well as the pharmaceutical industry. Regular people can learn about the ingredients in
aspirin as well as discover how the common drug is created. The pharmaceutical

industry can explore new methods to increase the amount of product being produced
when making aspirin. Pharmaceutical companies could make modifications to the
recrystallization method in order to decrease the amount of aspirin lost during this
process. This can improve the purity of their product and enhance efficiency. This
experiment will essentially expose the making of aspirin and its properties.

Review of Literature
The purpose of this experiment was to synthesize and analyze aspirin. To
synthesize aspirin, salicylic acid was reacted with acetic anhydride. The synthesized
sample was analyzed to ensure that aspirin was indeed synthesized, as well as to
determine the relative purity of the synthesized aspirin. During the analysis, the melting
temperature of the sample and the absorbance of salicylic acid impurity in the aspirin
sample were measured. The melting point and absorbance of aspirin are considered
intensive properties, meaning the properties are not affected by the amount of aspirin
present. Regardless of the amount of aspirin being analyzed, the melting point and
absorbance will always be the same. The percent yield of the synthesized aspirin was
also calculated using the absorbance value. Percent yield is not classified as an
intensive property of aspirin, but rather as an extensive property, because it does
depend on the amount of aspirin that is in a sample.
Aspirin is a salicylate, or a nonsteroidal anti-inflammatory drug (NSAID). Aspirin
is also an analgesic, a type of medicine used to relieve pain. Additionally, it is an
antipyretic, which reduces fever and inflammation. Aspirin is frequently used to treat
cardiovascular conditions including heart attacks, strokes, and angina ("Aspirin Uses,
Dosage, Side Effects"). Aspirin is an ester, a compound that is formed in the reaction of
an acid (a compound containing a carboxyl group) and an alcohol (a compound
containing a hydroxyl group). As exemplified in this experiment, aspirin is formed by the
reaction of the carboxyl group in acetic acid with the hydroxyl group in the salicylic acid
("Aspirin").

The synthesis of aspirin occurs in the reaction of salicylic acid and acetic
anhydride at approximately ninety degrees Celsius, with the addition of catalysts
("Aspirin"). In this experiment, phosphoric acid, H 3PO4, served as the catalyst. A catalyst
is a chemical substance that affects the rate of the chemical reaction. In a process
called catalysis, the catalyst changes the activation energy required for the completion
of the reaction. A catalyst provides an alternative pathway that has a lower activation
energy than the reaction pathway taken without a catalyst. The lower activation energy
allows the chemical reaction to occur more rapidly ("Catalyst"). Phosphoric acid is a
positive catalyst, meaning that it speeds up the rate of the chemical reaction by lowering
the activation energy.
Figure 1. Reaction of Salicylic Acid and Acetic Anhydride

Figure 1 above displays the reaction between salicylic acid and acetic anhydride
in the presence of the catalyst, phosphoric acid, H3PO4, to produce acetyl salicylic acid,
or aspirin and acetic acid.
After the aspirin has been synthesized, it must be separated from the reaction
solution and purified. Purification is essential in order to remove the unreacted acetic
anhydride and salicylic acid, as well as the acetic acid and phosphoric acid products
from the aspirin. Aspirin is insoluble in water; therefore, the aspirin can be isolated from
the reaction solution by washing the aspirin crystals with cold distilled water to filter the
reaction solution. The addition of water causes the acetic anhydride to decompose while
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the aspirin remains. Acetic acid and phosphoric acid can be removed with the addition
of the cold water because they are both soluble in water. However, salicylic acid is not
completely soluble in water, and it is not entirely removed when the crystals are
washed. Complete purification is reached through recrystallization. In this process, the
aspirin is dissolved in ethanol. The solution slowly cools, and the aspirin crystallizes out
of the solution, leaving behind the salicylic acid and other impurities ("The Synthesis of
Aspirin").
Following synthesis and purification, the melting temperature of the aspirin
sample was measured. To determine the melting temperature of the aspirin, a sample of
the synthesized aspirin was pulverized, inserted into a capillary tube, and connected to
a Melt Station, until the sample had melted completely. The samples melting
temperature was compared to the standard melting temperature of aspirin. The
standard value, or the known melting temperature of pharmaceutical aspirin, is 135 C
("Aspirin C9H8O4 - Pubchem"). The difference between the known melting temperature
and the melting point of the aspirin sample aids in indicating the accuracy of the aspirin
synthesis. The melting point of a compound is affected by its purity because the crystal
lattice, or the arrangement of atoms inside the crystals of the compound, is disrupted by
the presence of an impurity. For this reason, the melting point of the synthesized aspirin
can be used to estimate its purity because an impure compound will show a melting
point that is farther away from the known melting point than that of a pure compound. A
compound that melts at a narrow range, and at a temperature near the standard melting
point is considered to be pure. The further away the experimental melting point from the

known melting point, and the wider the melting point range, the less pure the compound
is.
The absorbance of the synthesized aspirin was also measured using a
spectrometer. A spectrometer is a device that measures the intensity of light as a
function of its wavelength. The spectrometer measures the quantity of light the
synthesized sample absorbs by passing a beam of light through the sample to reach a
detector ("Spectrophotometry). The absorbance of the synthesized aspirin was used to
calculate the percent yield of the sample. The absorbance can also be compared to the
absorbance of aspirin determined in the Vernier lab (Vernier Software & Technology).
Some aspects of the Beer-Lambert Law were used to analyze the absorbance of
the aspirin sample. Beers law states that the absorbance of a substance that is
dissolved in a non-absorbing solvent is directly proportional to the concentration of the
substance. According to this law, the absorbance of the aspirin sample can be used to
measure the concentration of the sample. The calibration curve of five standard
solutions with varying concentrations of salicylic acid was used in order to determine the
corresponding concentration from the absorbance of the aspirin sample.
Figure 2. Beers Law Plot

Figure 2 above shows the Beers Law Plot displaying the absorbance values and
concentrations obtained from the standard lab. This plot shows that as concentration
increases, the absorbance increases also. The Beers Law Plot was used in the process
to determine concentration and percent yield of the aspirin.
percent of aspirinsample=
actual yield
100
( theoretical
yield )
Figure 3. Percent Yield Formula

Figure 3 above displays the formula that was used to determine the percent yield
of the aspirin samples. The percent yield is equal to the ratio of the actual yield to the
theoretical yield multiplied by one hundred.
The percent yield of the synthesized aspirin was calculated during the analysis.
Percent yield describes how much of a material was produced in a reaction compared
to how much would be produced in an ideal reaction based on the conversion of the
limiting reactant. The percent yield was calculated to analyze the efficiency of the
reaction that synthesized the aspirin sample, and therefore determine how successful
the method of synthesis was. A low percent yield might suggest that the method of
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synthesis did not yield optimal product and may need improvement. A higher
percentage yield might suggest that the method employed was an efficient one.
However, when the percent yield is over 100%, this suggests that the product contains
some impurities. Impurities may result if the product is still wet with solvent, if the
products are not precisely separated from one another, or if there is waste in the
synthesized sample.
Other researchers have previously conducted experiments regarding the
synthesis of aspirin. In one experiment, the researchers described the results of the
aspirin synthesis, explaining that a milky, white mixture was observed when the salicylic
acid, acetic anhydride, and phosphoric acid were mixed. Moreover, the researchers
concluded that the melting point of the synthesized aspirin, which was 120 C to 124 C,
was near the standard melting point of aspirin. The percent yield was equal to 109.25%,
suggesting a slight error was made in the procedure. The experiment of the
predecessors differs from the chemistry experiment that was conducted because the
product was differentiated from commercial aspirin using iodine testing, showing that
commercial aspirin contains starch. The experiment described is applicable because it
uses the same catalyst that was used in this experiment to speed up the reaction.
In another experiment, researchers similarly synthesized aspirin by reacting
salicylic acid with acetic anhydride. However, sulfuric acid is used as the catalyst,
instead of phosphoric acid (Synthesis and Analysis of Aspirin"). This experiment
remains applicable, because a catalyst is present in the synthesis of aspirin.
In yet another experiment, aspirin was synthesized and analyzed for its melting
point and purity. This experiment is applicable because it describes the method to

determine the melting point of the sample using a melt station. However, this
experiment differs from the experiment that was conducted because the purity of the
sample was determined after the addition of ferric chloride, only based on its color. A
resulting purple color implied that a phenol group was present; the intensity of the color
determined the impurity of the sample ("Synthesis and Analysis of Aspirin").
Finally, in another previously conducted experiment, aspirin was synthesized,
and the purity of the synthesized aspirin was measured. This experiment differs from the
experiment that was conducted because it does not analyze the melting point of the
aspirin, which is important in determining the purity of a sample. However, the
experiment remains applicable because aspirin was synthesized in the reaction of
acetic anhydride with salicylic acid in the presence of phosphoric acid. Similar to the
experiment that was conducted, this previously conducted experiment both synthesized
and analyzed aspirin ("Synthesis and Characterization of Aspirin").
Problem Statement
Problem:
The purpose of the experiment was to synthesize aspirin and analyze properties
of aspirin by comparing the melting point, absorbance, and percent yield of the
synthesized aspirin to the known melting point, absorbance, and percent yield of
pharmaceutical aspirin.
Hypotheses:
The melting point of the synthesized aspirin will be within fifteen degrees of the
known melting point of aspirin. The absorbance of the synthesized aspirin will be less
than the absorbance calculated in the standard lab, which is 0.277. The percent yield for
the synthesized aspirin will be less than fifty percent.
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Data:
The independent variable was the synthesized aspirin. The dependent variables
were the melting point, absorbance, and percent yield of the synthesized aspirin.
Descriptive statistics were used to analyze the results of this experiment. Descriptive
statistics were appropriate for this experiment because there were not enough trials
conducted to perform a t test, and a descriptive analysis described the characteristics of
the sample aspirin. A descriptive analysis would allow the intensive properties of the
sample aspirin to be compared to the attributes of pharmaceutical aspirin.
Experimental Design
Materials:
50 mL Erlenmeyer flask
(2) 250 mL Erlenmeyer flask
500 mL Erlenmeyer flask
100 mL Volumetric flask
(2) 10 mL Graduated Cylinder
25 mL Graduated Cylinder
100 mL Beaker
(2) 250 mL Beaker
400 mL Beaker
500 mL Beaker
1000 mL Beaker
15 g Solid Salicylic Acid, C H O
LabQuest with LoggerPro software
1.5 mL 85% phosphoric acid solution, H PO
30 mL liquid acetic anhydride, C H O
7
11
Bchner funnel
Filter
Filter paper
Ice bath
Hot plate
3 mL Plastic Beral pipet
Scoopula
Spatula
(3) Plastic cuvette
(6) Glass capillary tube
Mortar and Pestle
Vernier Melt Station (0.1 C)
Spectrometer (0.001)
Analytical Scale (0.0001 g)
(2) Watch glass

0.025 M Iron (III) nitrate solution, Fe(NO )
Gallon distilled water
120 mL ethanol, C H O
Temperature probe (0.01 C)
Tongs
Tweezers
3 3
Procedure:
Part I Synthesize Aspirin
1. Obtain and wear goggles. Wear appropriate clothing and gloves to protect arms and
hands.
2. Turn on the hot plate to be used for the hot bath that will be prepared later on.
Maintain the temperature throughout the following procedures.
3. Measure out 2 grams of solid salicylic acid into a 50 mL Erlenmeyer flask.
4. Add 5 mL of acetic anhydride and 5 drops of 85% phosphoric acid (H PO ) solution.
Swirl the mixture by gently moving the flask so the contents mix. If necessary, use a
small amount of distilled water to rinse down bits of solid on the inner walls of the
flask.
CAUTION: Handle the phosphoric acid and acetic anhydride with care. Both
substances can cause painful burns if they come in contact with skin.
3
5. Synthesize the aspirin:

a. Place the 1000 mL beaker on the prepared hot plate. Monitor the water
temperature between 70-80 C using a temperature probe.
b. Partially submerge the 250 mL flask and contents in the hot-water bath, using
tongs to keep the flask up right in the hot water bath.
c. Heat the mixture in the hot-water bath for approximately 10-15 minutes, or until
the mixture ceases releasing vapors. Stir the mixture occasionally during heating.
Add 2 mL of distilled water about after 6-8 minutes of heating.
6. Crystallize the aspirin:
a. When no vapors are appearing, carefully remove the flask from the hot plate and
add 20 mL of distilled water.
b. Allow the mixture to cool to room temperature. Transfer the flask to an ice bath for
about five minutes. Crystals of aspirin should form in the flask as the mixture cools.
7. Wash the synthesized aspirin:
a. Set up a vacuum filtration using a Bchner funnel. Weigh and record the mass of
the filter paper to the nearest 0.0001 gram before filtering the solid.
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b. Transfer the contents of the flask to a Bchner funnel assembly. Filter the mixture
with vacuum suction.
c. When the liquid has been drawn through the funnel, wash the crystals with
approximately 50 mL of cold distilled water.
d. Using tweezers, gently transfer the filter paper with the product onto the watch
glass to air dry. Let the crystals air dry until the next lab period.
e. In the following lab period, weigh the dried recrystallized product on the filter
paper and record the mass to the nearest 0.0001 gram. Record the mass of the dry
aspirin sample in the data table.
Part II Test the Melting Temperature of an Aspirin Sample
8. Prepare a sample for melting:
a. Use a mortar and pestle to pulverize about 0.2 grams of the synthesized aspirin
and place it in a small pile in the mortar.
b. Pack a capillary tube 1/8 inch deep with the aspirin sample by inserting the open
end into the pile of aspirin. A small amount of the solid will be pushed up into the
capillary tube.
c. Tap the closed end of the capillary tube on the table top to compress the sample
into the closed end.
d. Check the control knob on the Melt Station to confirm that it is off.
e. Carefully insert the capillary tube of solid into one of the sample holders of the
Melt Station.
9. Connect the Melt Station power supply to an electrical outlet.
10. Connect the Melt Station sensor cable to the LabQuest.
11. Start the data-collection program, and then choose New from the File menu. Collect
the melting temperature data for 20 minutes.
12. In the first trial, observe the melting process and make an estimate of the melting
temperature of the aspirin sample.
a. Start data collection.
b. Set the Melt Station to a setting of 220 C. The red light will turn on, to indicate
active heating.
c. Carefully observe the sample. When the solid begins to melt, click Mark to mark
the temperature on the graph. Once the entire solid has completely melted, click
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Mark again. The two values marked on the graph describe the estimated melting
temperature range of the substance that will be recorded in Table 2.
d. When the approximate melting temperature range for the sample is determined,
stop data collection. Store the run by tapping the File Cabinet icon in LabQuest.
Discard the capillary tube and sample.
e. On the Melt Station, turn the control knob to the Fan/Cooling setting to be
prepared for the next trial. The blue light will turn on, indicating that the fan is cooling
the Melt Station.
13. Use a previously prepared sample in a capillary tube, as described in Step 8, to
determine the melting temperature of the sample:
a. Start data collection.
b. On the Melt Station, turn the control knob to the Rapid Heat setting.
c. Carefully observe the temperature vs. time graph. When the temperature is within
approximately 10C of the lowest possible melting temperature of the sample, turn
the control knob to a temperature setting corresponding to the expected melting
temperature, approximately 135 C.
d. Carefully observe the sample. When the solid begins to melt, click Mark to mark
the temperature on the graph. When the entire solid has completely melted, click
Mark again. The two values marked on the graph describe the estimated melting
temperature range of the substance. Stop data collection when this step is finished.
e. Store the run, and discard the capillary tube and sample.
f. On the Melt Station, turn the control knob to the Fan/Cooling setting to prepare for
the next trial.
14. Repeat Step 13 until the melting temperature range of the aspirin is determined.
Record the melting temperature range in Table 2.
15. Turn the control knob on the Melt Station to Off at the end of the testing.
Part III Test the Spectrophotometric Absorbance of an Aspirin Sample
16. Calibrate the Milton Roy Company Spectronic Spectrometer, 20D
(0420434A):
a. To prepare a blank cuvette, fill a cuvette 3/4 full with 0.025 M Fe(NO ) solution.
Place the blank cuvette in the Spectrophotometer.
3 3
b. Adjust the wavelength knob (top) so that the digital display reads the desired
wavelength of 590 nm, to correspond with the orange color of the solution.
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c. Adjust the transmittance knob (front panel, left knob) so that the transmittance
reads 100.0. Be careful not to turn too far to avoid turning the instrument off.
d. The absorbance mode on the Spectrophotometer should now read 0, if not, adjust
the absorbance knob to 0.
17. Prepare the stock salicylic acid solution:
a. Measure out about 0.20 grams of salicylic acid. Record the mass to the nearest
0.0001 gram in Table 3.
b. Transfer the salicylic acid to a 250 mL beaker and add 10 mL of ethanol. Swirl the
beaker to dissolve the solid.
c. Add 150 mL of distilled water to the beaker and mix the solution.
d. Transfer the solution from the beaker to a 250 mL volumetric flask. Thoroughly
rinse the beaker with several portions of distilled water and transfer the rinse water
to the volumetric flask. Add enough distilled water to fill the flask to the 250 mL mark.
Mix the solution thoroughly. Calculate the precise molar concentration of the stock
solution and record it in data Table 3.
18. Prepare the synthesized aspirin sample for testing:
a. Measure out about 0.4 grams of aspirin and transfer it to the 250 mL beaker.
Record the mass of the aspirin used to the nearest 0.0001 gram.
b. Add 10 mL of ethanol to the beaker of aspirin sample. Swirl the mixture to dissolve
the solid.
c. Add 150 mL of distilled water to the beaker. Mix the solution.
d. Transfer the solution from the beaker to a 250 mL volumetric flask. Thoroughly
rinse the beaker with several portions of distilled water, and transfer the rinse water
to the volumetric flask. Add distilled water, as needed, to fill the flask to the 250 mL
mark. Mix the solution thoroughly.
e. Transfer 5 mL of the aspirin solution from the 250 mL volumetric flask to a clean
and dry 100 mL volumetric flask. Add 0.025 M Fe(NO ) solution to the flask to make
precisely 100.0 mL. Mix the solution thoroughly.
3 3
19. Measure and record the absorbance value of the treated aspirin sample: (This must
be done within 10 minutes of completing Step 21)
a. Rinse and fill the cuvette 3/4 full with the sample. Place the cuvette in the
Spectrophotometer.
b. Monitor the absorbance value on the Spectrophotometer. Record the absorbance
in the data table.
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20. Discard all solutions. Clean materials and return to original spot.
Diagrams:
Figure 4. Aspirin Crystals Formed in Flask

Figure 4 shows the crystals that should form after the sixth step of the procedure.
Figure 5. Part I Materials

Figure 5 shows most of the materials used during the synthesis of aspirin in the
first part of the experiment. Not all materials are shown, such as flasks and beakers.
16
Figure 6. Part II Materials

Figure 6 displays the materials used in the second part of the experiment when
the synthesized aspirin samples were melted. Not all materials are shown.
Figure 7. Part III Materials

Figure 7 shows the materials used in the third part of the experiment when the
absorbance of the synthesized aspirin samples was analyzed. Not all materials are
shown.
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Figure 8. Melt Station Set-up

Figure 8 above shows the set-up of the melt station and LabQuest. This was
used to determine the melting ranges and average melting points.
Data and Observations

During the experiment, aspirin was synthesized and analyzed. To begin, the
aspirin was produced using salicylic acid, acetic anhydride, phosphoric acid, and
distilled water. Masses of the supplies used, as well as the volume of one of the
solutions, are listed in the table below.
Table 1
Part I Synthesis of Aspirin
Batch
Mass of salicylic acid used (g)
2.0066
2.0358
Volume of acetic anhydride used (mL)
5.0000
5.0000
Mass of acetic anhydride (1.08 g/mL) used (g)
5.4000
5.4000
Mass of aspirin and filter paper (g)
2.3938
1.9547
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Mass of filter paper (g)
0.2920
0.2917
Mass of aspirin synthesized (g)
2.1018
1.6630
Table 1 displays the mass of the salicylic acid, acetic anhydride, filter paper used,
and aspirin produced. The volume of the acetic anhydride is also shown.
After the aspirin was created and had time to crystallize, samples of each batch
were placed into capillary tubes and melted in the Melt Station. When the aspirin began
to melt, a mark was made on the LabQuest to signify the beginning of the melting
range. The aspirin sample then had time to melt completely; when the sample was fully
melted, another mark was made on the LabQuest. The two marks made up the melting
range of a sample. In total, three melting ranges were found from each batch of aspirin
in order to find an average range. The average of the range was then calculated to be
classified as the melting point of each batch of aspirin. The ranges, the average melting
range, and the average melting point of each batch are placed in the table below.
Table 2
Part II Melting Temperature Data
Batc
h
Trial
Melting
Temperature
Range
(C)
129.0-138.7
125.2-131.6
141.0-144.6
122.3-160.5
134.2-148.1
115.8-148.5
Average Range of
Melting Temperature
(C)
19
Average Melting
Temperature
(C)
131.7-138.3
135.0
124.1-152.4
138.3

Table 2 displays the average melting points of the first and second batches of
aspirin produced. Three samples from each batch were tested and averaged, giving an
average range.
Once samples from each batch of aspirin were melted, the absorbance of each
batch was calculated. To do this, a salicylic acid and distilled water solution was first
produced. The masses of the salicylic acid used in each solution are listed in the table
below. The moles of salicylic acid were also calculated (see Appendix A), along with the
initial molarity of the salicylic acid, and inserted into the table below.
Table 3
Part III Salicylic Acid Standard Stock Solution
Batch
Initial mass of salicylic acid (g)
0.2249
0.2010
Moles of salicylic acid (mol)
0.0016
0.0015
Initial molarity of salicylic acid (mol/L)
0.0065
0.0058
Table 3 displays information recorded and calculated about the salicylic acid
including the initial mass, number of moles, and molarity of the salicylic acid. This data
was used to calculate percent yield and absorbance.
To continue with finding the absorbance of each aspirin sample, a concentration
curve needed to be created with the following data. The values are from the Vernier lab.
20

The calibration curve was then used to convert the absorbance values to concentration
values.
Table 4
Part III Beers Law Data for Salicylic Acid Standard Solutions
Trial
Concentration of Salicylic Acid

Standard Solutions
(M)
Absorbance of Salicylic Acid

Standard Solutions
5.79 10-4
1.005
4.63 10-4
0.832
3.47 10-4
0.616
2.32 10-4
0.423
1.16 10-4
0.211
Table 4 displays the given concentration of each standard salicylic acid solution
with its given corresponding absorbance. The values are essentially data points that
create a curve. The curve is shown below, along with the equation that plots the curve.
Figure 9. Absorbance vs. Concentration

Figure 9 displays the graph of the salicylic acid standard solutions absorbance
and concentration.
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The mass and absorbance of the synthesized aspirin along with the
concentration, number of moles, and mass of salicylic acid in the aspirin sample were
recorded in the table below. The mass of aspirin in the sample was also recorded.
Finally, the percent of aspirin in the sample and the percent of aspirin in the sample
after correction for purity were entered into the table.
Table 5
Absorbance of Synthesized Aspirin
Batch
Initial mass of aspirin sample (g)
0.3983
0.3974
Absorbance of aspirin sample
0.119
0.203
Concentration of salicylic acid (mol/L)
5.0 10-5
1.010-4
Moles of salicylic acid in aspirin sample (mol)
5.010-6
1.010-5
Mass of salicylic acid in aspirin sample (g)
0.0345
0.0691
Mass of aspirin in sample (g)
0.3638
0.3283
Percent aspirin in sample (%)
91.33
82.62
Percent aspirin in sample Corrected for Purity (%)
73.35
51.72
Table 5 displays the mass and absorbance of the aspirin sample; concentration,
moles, and mass of salicylic acid in the aspirin sample; mass of aspirin in the sample;
and the percent of aspirin in the sample before and after correction for purity. Percents
of aspirin in each sample were calculated using equations (see Appendix C).
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During the experimental process, observations were written down and recorded
into the table below.
Table 6
Observations
Batc
h
1
Observations
The Fe(NO ) turned orange when diluted with distilled water. The aspirin
produced was a gritty, powder-like substance.
The synthesized aspirin was pure white.
The aspirin mixed with ethanol and distilled water was purple.
The stock salicylic acid, ethanol, and distilled water solution showed the
darkest purple color.
Gracie observed the Melt Station.
Veronica and Megan calibrated the spectrometer.
3 3
The aspirin produced had small, thin particles.

The synthesized aspirin was pure white.
This sample also took a longer time to melt.
The aspirin mixed with ethanol and distilled water was less purple than the
previous batch and displayed an orange tint.
Gracie observed the Melt Station.
Veronica and Megan calibrated the spectrometer.
Table 6 contains the observations of both aspirin batches produced.
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Figure 10. Synthesized Aspirin Batch One

Figure 10 displays the dried crystals after the reaction between salicylic acid and
acetic anhydride. This is the synthesized aspirin of batch one.
Figure 11. Synthesized Aspirin Batch Two

acetic anhydride. This is the synthesized aspirin of batch two.
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Data Analysis and Interpretation

Data was collected for the melting point and absorbance of the aspirin samples.
After synthesizing the aspirin, the data for the melting point was collected using a Melt
Station and LabQuest. Next, absorbance was calculated for each aspirin sample using
the spectrometer. The absorbance data was then used to calculate the percent yield of
the synthesized aspirin samples. Descriptive analysis was used to analyze the data
collected in this experiment. This method of analysis was the most appropriate for this
25

experiment because this experiment was only conducted twice; therefore, there were
not enough trials to conduct a statistical test. Descriptive analysis was a valid way to
analyze the synthesized aspirin because it summarized the characteristics of the aspirin
and described the graphs of the data collected from the analysis of the aspirin.
Additionally, the processes used from the Vernier lab to analyze the aspirin are
accepted processes; therefore, the accepted processes represent the control. Although
the trials were not randomized and were only replicated once, the processes that
occurred during the experiment have been used multiple times in the past and have
been proven to yield proper results. To find the melting point of the synthesized aspirin
samples, procedures were followed from a standard lab, ensuring accuracy. The same
was done to determine the absorbance and percent yield.
Figure 12. Melting Point of the First Run from the First Batch
Figure 12 displays a graph of the temperature of the synthesized aspirin while in
the Melt Station as a dependent variable of the time in minutes. There are two marks
indicated on the graph. The first mark was created when the synthesized aspirin began
26

melting, while the second mark was made when the aspirin sample was completely
melted. The two marks were created to form a range; the range for the melting point of
the first run from the first batch of synthesized aspirin is from 129.0 C to 138.7 C. The
red line indicates the known melting point of pharmaceutical aspirin, which is 135.0 C.
As visible on the graph, the known melting temperature of aspirin is between the melting
range of the synthesized aspirin sample. Therefore, although the aspirin sample began
to melt when it was below the pharmaceutical aspirin melting point, it required a higher
temperature to fully melt. The final melting temperature of the synthesized aspirin was
138.7 C. Furthermore, the graph displays a steep positive slope. For the first minute,
the temperature remained constant at room temperature; however, it began to increase
continuously until the aspirin sample finally reached its melting point. The line segment
that is created by the two marks has a slope of approximately 9.798, meaning that with
every minute after the substance started to melt, the temperature increased by about
9.798 degrees Celsius. Finally, the synthesized aspirin sample took approximately ten
minutes to melt completely after being placed into the Melt Station.
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Figure 13. Melting Point of the Second Run from the First Batch
Figure 13 pictures a temperature graph of the second run from the first batch of
synthesized aspirin while in the Melt Station. The second mark is below the red line; this
sample of aspirin did not require as high of a temperature to melt compared to
pharmaceutical aspirin. The aspirin sample in this particular run quickly started to heat
up as soon as it was inserted into the Melt Station. When the sample reached a
temperature of 125.2 C and started to melt, the increase in temperature started to slow
down until the substance was fully melted at 131.6 C. The slope of the line segment
created by the two marks is about 1.433, which implies that every minute after the
aspirin began to melt, the temperature would increase by approximately 1.433 degrees
Celsius. The aspirin sample took approximately seven minutes to completely melt,
which is almost three minutes less than it took to completely melt in the first sample of
aspirin from the first batch.
28
Figure 14. Melting Point of the Third Run from the First Batch
Figure 14 displays a graph of the temperature of the third sample from the first
batch of synthesized aspirin as it was inside the Melt Station. The melting range of this
sample of synthesized aspirin is from 141.0 C to 144.6 C, as shown in the graph. It is
noticeable that the temperature where the aspirin began to melt, as well as the
temperature where the aspirin was completely melted, is higher than the pharmaceutical
aspirin melting temperature. This suggests that this particular aspirin sample required a
higher temperature in order to melt compared to the known aspirin melting point.
Additionally, the slope of the graph is steep and constant. The line segment created by
the two marks has a slope of 22.500, which means that with every minute after the
sample began melting, the temperature increased by 22.500 degrees Celsius. During
the first several seconds of melting, the temperature of the Melt Station was fluctuating
around 75.0 C until it started to increase rapidly. The temperature continued to quickly
increase until the aspirin sample was melted thoroughly. Finally, this aspirin sample only
29

took about four minutes to completely melt, which is a very short time period compared
to the previous samples.
The average melting temperature range of batch one is 131.7 C to 138.3 C,
resulting in an average melting temperature of 135.0 C. Therefore, this batch of
synthesized aspirin melted precisely at the known melting point of aspirin on average.
Figure 15. Melting Point of the First Run of the Second Batch
Figure 15 displays the temperature of the synthesized aspirin sample from the
second batch while in the Melt Station over time. The melting range of the first run from
the second batch synthesized is from 122.3 C, when the aspirin began melting, to
160.5 C, when the aspirin sample was fully melted. Although the standard aspirin
melting point of 135.0 C is within this range, this aspirin sample required a much higher
temperature to melt entirely. The graph also shows that the temperature began to
increase immediately after the aspirin sample was placed in the melt station. Similar to
the first run from the first batch of synthesized aspirin, the temperature is at room
temperature at the beginning, and it begins to increase continuously until the aspirin
30

sample finally reaches its melting point. Just as in the first and third runs of the first
synthesized batch of aspirin, the temperature of the first run of this second batch of
aspirin shows a steep positive line, which implies that the temperature was increasing
rapidly and continuously until the aspirin sample was completely melted. The slope of
the line segment formed by the two marks is about 10.914. This means that with every
minute that passed after the aspirin sample began to melt, the temperature increased
by about 10.914 degrees Celsius. Moreover, the aspirin sample took approximately ten
minutes to melt completely, which is very similar to the first run sample from the first
batch of synthesized aspirin.
Figure 16. Melting Point of the Second Run of the Second Batch
Figure 16 displays the temperature of the synthesized aspirin sample of the
second run from the second batch while melting over time. The melting range of this
aspirin sample was between 134.2 C to 148.1 C, from when the aspirin sample began
melting to when the sample was melted entirely. The first mark that shows when the
31

aspirin sample began melting is very close to the known melting point of aspirin;
however, the synthesized aspirin required a higher temperature to melt completely. The
graph shows a positive gradual slope, indicating that the temperature was increasing
slowly throughout the melting process. The slope of the line segment formed by the two
marks is about 1.691, which means that with every minute after the sample began to
melt, the temperature increased by about 1.691 degrees Celsius. Unlike the analysis of
the previous synthesized aspirin samples, the temperature of the melt station at the
beginning of melting was significantly high at about 125 C. Lastly, the aspirin sample
took approximately twelve minutes to melt completely.
Figure 17. Melting Point of the Third Run of the Second Batch
Figure 17 shows the temperature graph for the third sample of the second batch
of synthesized aspirin while inside the Melt Station. The melting range, which is the time
between when the aspirin began to melt and when it was thoroughly melted, is from
115.8 C to 148.5 C. The known melting point of aspirin is within this range; however,
this particular sample had a very large time in between when it began to melt and when
32

it was fully melted. Unlike previous graphs, particularly the graph for the third run of the
first batch of synthesized aspirin, the temperature of the Melt Station did not increase
rapidly. There was a constant increase in temperature throughout this run. Additionally,
this aspirin sample required a high melting temperature at almost fourteen degrees
above the known aspirin melting point. The slope of the line segment created by the two
marks is about 2.774. This illustrates that with each passing minute after the aspirin
sample began to melt, the temperature increased by about 2.774 degrees Celsius.
Finally, this sample took over seventeen minutes to completely melt and had a melting
range that lasted over ten minutes. This result is surprising considering the Melt Station
started at a high temperature of almost 100 C.
The average melting temperature range of batch two is 124.1-152.4 C, resulting
in an average melting temperature of 138.3 C. This is a mere 3.3 C above the known
melting point of aspirin.
Although the same method was applied to analyze the melting points of the
synthesized aspirin samples, there were differences in the time the samples took to
begin melting. Some of the samples began melting quickly, while others took a longer
period of time. For example, the graph in Figure 14 shows that the particular sample
only took about three minutes to start melting. On the contrary, the aspirin sample in
Figure 12 took almost nine minutes to begin melting.
Additionally, the various lengths of melting ranges, which can also be referred to
as the time between the two marks on the graph, indicated a difference in melting
speed. In some graphs, particularly the graph in Figure 6, there is a large amount of
time in between when the aspirin sample first started to melt to when the sample was
33

completely melted. On the other hand, there are graphs that have a short melting range,
such as the graphs in Figure 12 and Figure 14, where the aspirin sample would start to
melt and was entirely melted shortly after.
Furthermore, another aspect that can be compared is the melting temperature of
all of the samples. Although all of the samples that were analyzed contained the known
melting point of aspirin, some required a higher temperature to melt completely, such as
the sample in Figure 17. The melting temperature of the sample in Figure 17 was
seventeen degrees over the known aspirin melting point. On the other hand, Figure 13
involved a sample that had a melting point below the standard aspirin melting point.
In addition, the slopes of the graphs displaying the temperatures of the
synthesized aspirin samples were analyzed. Although all of the graphs showed a
positive trend in the slope, there were times when the slope remained constant until the
melting point was reached. Also, while some graphs were steep, others were more
gradual. For instance, in Figure 16, the slope of the graph was gradual and did not have
a rapid increase in temperature. In Figure 15, the increase in temperature was not slow.
There was a rapid increase in temperature; however, the slope stayed constant until the
melting point was reached. In Figure 13, the slope changed after three minutes of being
in the melting station. The temperature changed from rapidly increasing to slowly
increasing.
Finally, the initial temperature of the Melt Station was an aspect that can be
compared for each of the samples. For certain aspirin samples, the melting stations
initial temperature was at room temperature; however, for other aspirin samples, the
initial temperature of the melting station was much higher. For instance, in Figure 12
34

and Figure 15, the Melt Station was initially at room temperature. However, for the
analysis of the aspirin sample described in Figure 16, the initial temperature of the
melting station was over 100 C.
Figure 18. Box Plot of Start of Melting Temperatures

Figure 18 displays a box plot of the beginning melting temperatures of the first
and second batches of synthesized aspirin. The data shows the temperature when the
aspirin began to melt, which is represented by the first mark on each temperature
graph. The beginning temperatures ranged from 115.59 C to 140.79 C. This is a
noticeably large difference of 25.20 C. The median of the six melting temperatures is
126.89 C while the first quartile is 122.09 C and the third quartile is 133.99 C. The
quartile values make up the interquartile range, which spans 11.90 C. Although a box
plot arranges data as an organized visual, plotting only six data points may cause a
statistical visual error. Typically, thirty or more data points are needed to validate
statistical conditions; six data points may deceive the eye. Only six data values were
available, so the data was still arranged into a box plot in order to compare them.
35
Figure 19. Box Plot of Complete Melt Temperatures

Figure 19 shows a box plot of the temperatures found during the analysis of the
end melting temperatures of the first and second batches of synthesized aspirin. The
data represents the temperature when the entire aspirin sample was melted completely.
The final melting temperature of melted samples ranged from 131.60 C to 164.94 C.
This large range has a difference of 33.34 C. The median of the six melting
temperatures is 146.35 C, the first quartile melting mark is at 138.70 C, and the third
quartile melting mark is at 152.94 C. The first and third quartile values make up the
interquartile range, which has a range of 14.24 C.
When comparing the box plots of both the beginning of the melting range and the
end of the melting range, there is some overlapping. The overlapping of the two box
plots spans from 131.90 C, the minimum of the end of the melting range, to 140.79 C,
the maximum of the beginning of the melting range. This makes up a span of 8.89 C.
This implies that some temperatures of a sample when the aspirin was entirely melted
36

were lower than some temperatures of a sample when the aspirin was just beginning to
melt.
Figure 20. Normal Probability Plot

Figure 20 above displays the normal probability plot of the average melting
points in degrees Celsius. Three runs were conducted to determine a range for the
melting point of the aspirin synthesized for both batches. Each range was averaged,
and all six averages were plotted on the normal probability plot. Five of the six averages
are plotted fairly close to the normal probability line, with one of the five averages being
plotted right onto the line. This normal probability plot shows that the data for the
average melting points were moderately normal.
37
Figure 21. Absorbance vs. Concentration for Salicylic Acid

Figure 21 displays the concentration curve used to determine the concentration
that corresponds with a specific absorbance. The concentration is then used in the
mathematical equation that calculates the percent yield of the synthesized aspirin.
Using the spectrometer, the absorbance of the first aspirin sample from batch one was
found. The absorbance of the batch one aspirin sample is 0.1190. The graph in Figure
18 can be used to find the corresponding concentration of a sample with a 0.1190
absorbance; the concentration is approximately 5.0 x 10 -5 moles per liter of solution. The
absorbance of the batch two sample is 0.2030, with a corresponding concentration of
1.0 x 10-4 moles per liter of solution. The absorbance of batch one and two, 0.1190 and
0.2030, are very close in relationship to each other.
The percent yield of the synthesized aspirin for each batch was determined (see
Appendix B). The percent yield of the synthesized aspirin from batch one was 73.35%
while the percent yield of the synthesized aspirin for batch two was approximately
51.72%. The percent yield for batch one is noticeably higher than the percent yield of
batch two.
38

Overall, two intensive properties of both batches of synthesized aspirin were
analyzed: the melting point and absorbance. The percent yield of each synthesized
aspirin batch was also calculated. The first batch of sample aspirin had the exact same
melting point as commercial aspirin while the second batch had a melting point that was
slightly higher. Furthermore, the first aspirin sample had a lower absorbance than the
second batch of aspirin did. Finally, the first aspirin batch was found to have a higher
percent yield than the second batch.
Conclusion
The purpose of this experiment was to synthesize and analyze aspirin. The
synthesized aspirin was the independent variable. The melting point, absorbance, and
percent yield of the synthesized aspirin were the dependent variables that were tested
and calculated. Melting point and absorbance are classified as intensive properties of
aspirin because they do not depend on the amount of aspirin that is being analyzed.
Percent yield is an extensive property because the amount of aspirin in a sample does
affect its data. The first hypothesis stated that the melting point of the synthesized
aspirin would be within fifteen degrees of 135 C, the known melting point of aspirin.
This hypothesis was accepted based on the melting point ranges of the synthesized
aspirin samples. It was also hypothesized that the absorbance of the synthesized
aspirin would be less than 0.277, the absorbance calculated in the Vernier lab. This
hypothesis was accepted because the absorbances of both aspirin samples were below
0.277. Finally, the last hypothesis estimated that the percent yield of the synthesized
aspirin would be less than fifty percent. This hypothesis was rejected by the data of the
39

synthesized aspirin samples because both aspirin samples had a percent yield higher
than fifty percent. The hypotheses were based on values from the Vernier lab that this
experiment modeled. (Vernier Software & Technology) The values determined in this
experiment were also compared to the values in the Vernier lab.
Melting point, as well as percent yield which is determined from absorbance, both
helped in determining the purity of the synthesized aspirin samples. When a
synthesized aspirin sample has a temperature near the known pharmaceutical melting
temperature of 135 C, a reflection of precision is shown. The difference between the
determined and standard melting temperatures aids in indicating the accuracy of the
aspirin synthesis. A pure compound will result in a melting point that is relatively near
the known melting point of pharmaceutical aspirin due to accuracy. The melting point of
the synthesized aspirin can be used to estimate its purity because an impure compound
will show a melting point that is further away than that of the pure compound.
Furthermore, the more narrow the melting range, the purer the compound.
Therefore, a compound that melts at a narrow range and at a temperature near the
known melting point is most likely to be pure. The further away the experimental melting
point and the broader the melting point range, the less pure the compound is.
The melting temperature of the aspirin was the first variable analyzed. The
average melting point of the synthesized aspirin from the first batch was 135 C, with an
average melting range of 131.7-138.3 C. This melting point supports the hypothesis
because it is not only within fifteen degrees of the known melting point, but it is also
exactly equal to the known melting point of aspirin. The first synthesized aspirin sample
had a narrow range of only about 6.6 degrees Celsius.
40

The percent yield that was calculated supports the correlation between melting
point and purity. The percent yield of the first aspirin sample was 91.33%, with a purified
percent yield of 73.35%. The percent yield displays that the first batch of synthesized
aspirin had a high percent yield; therefore, the aspirin sample was pure indeed. This
percent yield is higher than fifty percent, and thus calls for a rejection of the initial
hypothesis.
The melting point of the second batch of aspirin differed from the known melting
point of commercial aspirin due to the impurities of the aspirin samples. The second
aspirin batch had an average melting temperature of 138.3 C, with a broad melting
range from 124.1 C to 152.4 C. This melting point supports the hypothesis because
138.3 C is only 3.3 degrees higher than 135 C. The percent yield of this aspirin
sample was 82.62%, with a purified percent yield of 51.72%, and therefore rejects the
hypothesis. The broad melting range of 28.3 degrees and lower percent yield support
that the sample was not as pure as the first batch of synthesized aspirin.
Absorbance further aids in determining the purity of the synthesized aspirin.
Absorbance of an aspirin sample describes the amount of light that is absorbed or
reflected by the substance. There is a directly proportional relationship between
absorbance and concentration, which is the amount of a substance in a defined space.
This relationship is displayed in the absorbance and corresponding concentrations that
were determined during the experiment. The first batch of aspirin had a lower
absorbance of 0.119 and a lower concentration of 5.0 10-5. The absorbance of the
second batch of aspirin had a higher absorbance of 0.203, along with a higher
concentration of 1.0 10-4. Therefore, a high absorbance yields a high concentration. A
41

high concentration suggests that there is a large number of moles per liter of the
substance. Applying this knowledge to the results of this experiment, the more
concentrated the solution with the aspirin was, the purer it was.
The aspirin produced in this experiment had a much lower absorbance than
expected. The absorbance of both aspirin batches differed slightly from the absorbance
value calculated in the standard lab. In this experiment, the absorbance of the first
aspirin batch was 0.119 while the absorbance of the second batch of aspirin was 0.203.
These differed from and were lower than the absorbance determined in the standard
lab, which was 0.277. However, the absorbance of both aspirin samples that were
determined in this experiment support the hypothesis because they are both less than
0.277, which was expected. This large difference may be a result of impurities in the
sample, much like how the melting point was affected by the impurity of the second
sample.
Although the absorbance and concentration values determined for the aspirin
samples suggest that the second batch of aspirin had a higher concentration of salicylic
acid than the first, this implication contradicts the melting point and percent yield values.
The melting point and percent yield values prove that the first batch of aspirin was more
pure due to a melting point closer to the standard and a higher percent yield. However,
the absorbance and corresponding concentration suggest that the second batch of
aspirin was more pure due to a higher concentration of salicylic acid. The first sample of
synthesized aspirin had an average melting point of exactly 135 C, and a narrower
melting point range. Trial one also had a high percent yield, which helps prove the
sample was pure. On the contrary, trial two had a higher absorbance value compared to
42

trial one, which can prove that the second trials aspirin was pure; however, trial two had
a lower percent yield. This contradiction in data proves that both absorbance and
percent yield have an effect on the classification of whether or not an aspirin sample is
pure. This reasoning suggests that both aspirin samples are pure, but aspirin batch one
is quite pure and batch two is less pure.
Several factors may have affected the impurity of the aspirin samples. The
percent yield for both synthesized aspirin batches was above the hypothesized percent
yield of fifty percent after the samples were checked for purity (See Appendices B and C
for purity calculations). As described previously, the high percent yield suggests a purer
substance, but the absorbance shows otherwise. The synthesized aspirin was exposed
throughout the course of the trial period, causing possible contamination to the
substance. Possible contamination may have been the cause of inadequate results of
the absorbance that contradict the other variables.
Furthermore, this contradiction of purity might be due to the differing wavelength
settings and varying spectrometers. The absorbance of the five standard solutions that
were used to create a calibration curve were acquired from the Vernier lab. These
absorbance values were determined on a Vernier SpectroVis Plus Spectrophotometer,
which is a different spectrometer than the one used in this experiment. The Vernier
equipment was digital, while the spectrometer used in this experiment was analog. In
this experiment, the wavelength of the spectrophotometer was set to 590 nanometers
because that wavelength corresponded to the purple color of the synthesized solution
created with the iron (III) nitrate and salicylic acid. The spectrometer used to determine
the five standard solutions from the Vernier Lab may have been set to a different
43

wavelength, but this detail was not specified. Differing equipment may cause conflicting
data. Since science supports the correlation between the melting temperature and
percent yield, the absorbance may be the issue.
The values collected in this experiment agree with current research, specifically
the results from the Vernier lab that was modeled. As mentioned previously, the melting
points that were determined in this experiment agree with the melting point results from
the Vernier lab as both are near the known melting point of aspirin. Another experiment
conducted showed a melting point range between 120-124 C. Although the results
collected in this experiment display a more accurate melting point that is closer to the
known melting point of aspirin, the results of this experiment still do agree with the
previously conducted experiment mentioned because both melting ranges are close to
the standard melting point of aspirin. The percent yields of 73.35% and 51.72%, agree
with the Vernier research that displayed a percent yield of 55.9%. This sample had a
lesser purified percent yield than the given 55.9% and a higher average melting
temperature.
Along with success comes complications. Discrepancies in the data may have
been caused by errors in the experimental design. The first issue that occurred in the
experimental design that may have had an effect on the results was during part one: the
synthesis of the aspirin. While producing the aspirin, the beaker containing the aspirin
was partially submerged in the hot water bath until vapors stopped releasing or until a
certain time limit was reached. Due to the batches of aspirin being synthesized on
different days, the batches of aspirin had differences in consistency of data results and
44

overall appearance (see Appendix D), which may have been caused by the differing
lengths of time the samples were in the hot water bath.
Another issue that occurred during the experimental design was when the
synthesized aspirin was filtered using the Bchner funnel. After the aspirin was
produced, it was necessary that the excess impurities be filtered from it. Depending on
how long the filter ran for, the aspirin batches may have caused a difference in
consistency of the crystals and purity. Also, the percent yield of the synthesized aspirin
would be affected by the quality of filtration because some of the synthesized aspirin
may have been corrupted or disposed of while the filter paper with the aspirin crystals
was being removed from the funnel.
Lastly, absorbance could have been affected by steps in the experimental design.
The differing positions of the cuvettes while in the spectrometer could have affected the
amount of light being reflected and absorbed; therefore the placement of each cuvette
could have had an effect on the absorbance.
The last hindrance was the spectrometer usage. The spectrometer caused many
difficulties while calculating absorbances. Sometimes the spectrometer would max out
while the wavelength was set, which delayed the data collection. Also, the spectrometer
used in the experiment was much less equipped compared to the spectrometer the
Vernier lab suggested to use. The standard concentrations that were used were tested
on a different spectrometer. A calibration curve was made from these standards that
helped calculate absorbance of the aspirin samples. This caused contradiction between
data results.
45

The errors in the experimental design had a negative impact on the results and
conclusion of the experiment. The largest experimental design issue was the
spectrometer used in the absorbance analysis. This issue seemed to impact the data
results greatly. All of the errors that occurred during research had an effect on the data
results. There were some errors that could have been prevented and were not; which
implies the data may be less reliable.
If this experiment was conducted again, a more advanced spectrometer would be
preferred. The different spectrometer used in the Vernier lab determined the proper
wavelength setting. This would be much more efficient and would increase accuracy
between absorbance and purity. The results would become more reliable in turn. Also,
emphasizing accuracy during measuring and recording is key to precision.
The research completed in this lab can be expanded on in future pharmaceutical
research; in fact, expansion on both the synthesis and analysis can be done. To expand
on the synthesis of aspirin, bigger or smaller batches can be synthesized to allow larger
or smaller analyses to be done.
To expand on the research from the analysis perspective, attributes other than
melting point, absorbance, and percent yield of the synthesized aspirin can be observed
and tested. For instance, the antipyretic, analgesic, blood-clot-reducing, and antiinflammatory properties of aspirin can be tested. To test the antipyretic property of
synthesized aspirin, a patient or test subject could consume the aspirin while having a
fever, and the difference in temperatures of before and after consumption could be
compared. Additionally, to analyze the analgesic aspect of aspirin, a subject in pain
could rate their pain on scale and compare the rate to the amount of pain they have
46

proceeding the consumption of the aspirin. Also, to test the property of aspirin that
reduces blood clots, a test subject with existing blood clots can consume the
synthesized aspirin and find the difference in the amount of blood clots before and after
consumption of the aspirin. Finally, the anti-inflammatory attribute of synthesized aspirin
can be investigated by allowing a test subject to consume the aspirin while having an
inflamed area of the body to compare the inflammation from before and after.
This research along with the expanded research could assist the pharmaceutical
industry, specifically brands such as Tylenol, Advil, or Bayer that commercially
produce aspirin. This experiment essentially mimicked the work of pharmacists and
demonstrates the process of synthesizing a pain reliever to non-pharmacists. Data
results prove that even small mistakes can have an effect on the purity of the aspirin, so
pharmacists will be able to discover different synthesizing methods with the help of the
research to improve the purity of their product. Quality and amount of product is vital in
the pharmaceutical industry. This aspect is demonstrated in this experiment with the
percent yield of the aspirin.
All in all, the results of this experiment are beneficial to the pharmaceutical
industry and the common people. Being informed on how aspirin is synthesized
exposes the true ingredients and the method used to make this common pain-reliever.
This experiment manifests that behind each aspirin consumed lies the product of
several diligent employees.
47
Acknowledgements
Thanks and appreciation is given to the people that guided and encouraged us
through the course of this experiment. Specifically, thanks to Mrs. Hilliard for her
guidance. She was kind enough to go out of her way to provide the proper equipment
needed to complete this experiment which would not be available otherwise. Her
supportive, positive reinforcements pushed this experiment to reach its full potential.
Thanks to Mrs. Dewey for being helpful, and supporting this experiment by perfecting
the data. Lastly, thanks to Mr. Supal for always instilling positive and encouraging
thought along the way.
48
Appendix A: Molarity Calculations for Data and Observations

number of moles=mass
1 mole
mass
=
molar mass molar mass
mass=0.2249 g
molar mass of salicylic acid=138.13 g
number of moles=0.2249
1
0.2249
=
138.13 139.13
number of moles 0.0016 moles

Figure 1. Mole Calculations
Figure 1 displays the formula to calculate the number of moles in the mass of a
specific compound. In this case, the number of moles being found is from a sample of
0.2249 grams of salicylic acid. The mass was divided by the molar mass of salicylic
acid, which was found by adding the molar masses of all of the elements that make up
49

salicylic acid. This amount of moles was used in the calculations to calculate percent
yield and absorbance.
molarity=
number of moles
volumeliters
Figure 2. Molarity Equation

Figure 2 shows the calculation used to find the molarity of a substance. The
molarity can also be known as the concentration of a substance. To calculate molarity,
the number of moles is divided by the volume of a solution.
Appendix B: Actual and Theoretical Yield Calculations

moles of salicylic acid=mass of salicylic acidused molecular weight of salicylic acid
2.0066 g 138.13
g
mol
0.0145 mol
theoretical mass of aspirin=moles of salicylic acid produced molecular weight of aspirin

0.0145 mol 180.16
g
mol
2.6172 g
molar amount of salicylic acid impurity100 mL sample=concentration 10

5
5.0 10 M 10
6
5.0 10 M
50
molar amount of salicylic acid impurity100 mL sample
5.0 106 M (
( 2505 )
250
)
5
2.50 10 mol
mass of salicylic acid=moles of salicylic acidinitial aspirin sample molecular weight of salicylic acid
4
2.50 10 mol 138.13
g
mol
0.0345 g
actual yield=initial mass of salicylic acidunreacted salicylic acid

actual yield=0.3638 g
theoretical yield=0.3983 g
unreacted salicylic acid=0.0345 g
Figure 1. Calculations for Math in Percent Yield of Synthesized Aspirin

The calculations above were completed in order to lead to the percent yield of
the first batch of synthesized aspirin.
51
Appendix C: Percent Yield Calculations
percent of aspirinsample=
actual yield
100
( theoretical
yield )
0.3638
)100
0.3983
91.33
mass of the synthesized aspirin corrected for purity=mass of the synthesized aspirin aspirinsample
2.1018 0.9133
52

1.9196 g
corrected for purity
( actual yield
) 100
theoretical yield
percent yield=
g
100
( 1.9196
2.6172 g )
0.7335 100
73.35
Figure 1. Calculations for Percent Yield of Synthesized Aspirin Batch
The calculations above were completed in order to determine the percent yield of
the batch of synthesized aspirin.
Appendix D: Appearance of Aspirin

The appearance of each aspirin sample differed. The first batch was grainy while
the second batch was flaky.
53
Figure 1. Synthesized Aspirin Batch One

acetic anhydride. This is the synthesized aspirin of batch one.
Figure 2. Synthesized Aspiring Batch Two

acetic anhydride. This is the synthesized aspirin of batch two.
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Marougail Morris Phillips Finalpaper

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