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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
actual yield
100
( theoretical
yield )
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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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
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
12
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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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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16
17
2.0066
2.0358
5.0000
5.0000
5.4000
5.4000
2.3938
1.9547
18
0.2920
0.2917
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 3
Part III Salicylic Acid Standard Stock Solution
Batch
0.2249
0.2010
0.0016
0.0015
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
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.
Table 5
Absorbance of Synthesized Aspirin
Batch
0.3983
0.3974
0.119
0.203
5.0 10-5
1.010-4
5.010-6
1.010-5
0.0345
0.0691
0.3638
0.3283
91.33
82.62
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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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
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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
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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.
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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
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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
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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
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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
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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
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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.
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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
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molarity=
number of moles
volumeliters
g
mol
0.0145 mol
g
mol
2.6172 g
5.0 10 M 10
6
5.0 10 M
50
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
g
mol
0.0345 g
theoretical yield=0.3983 g
unreacted salicylic acid=0.0345 g
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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
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.
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Works Cited
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