Synthesis of Aspirin

Braden Paulinellie & Drew Bankovich

Assigned: May 10, 2016
Due: May 20, 2016
Abstract:
In this experiment, aspirin will be synthesized from salicylic acid. To start this process,
acetic anhydride and 85% phosphoric acid will be added to the salicylic acid and will heat for ten
minutes. Distilled water will be added and the reaction flask will be placed in an ice bath,
starting the crystallization process. In order to wash the final product, a vacuum apparatus will be
assembled and used. There are two ways of checking for impurities that are a part of the end of
this experiment: drops of 0.02 M FeCl will be added until it turns purple and the melting point
will be determined and compared to the true value. It took one drop to turn the solution purple.
Calculations will include finding the mass of aspirin obtained, the melting point of the aspirin,
the percent yield, and the error. Results from this lab include 2.7970 g of aspirin obtained, a
135.6C melting point, a percent yield of 71.5%, and a 0.6C absolute error with a 0.4% error.

Discussion:
Aspirin is a synthetic compound used medicinally to relieve mild or chronic pain, and
reduce fevers and inflammation. Aspirin is an over-the-counter drug that is available to the public
is a form of pain medication. Aspen came to being in the late 1890s in the form of acetylsalicylic
acid when chemist Felix Hoffmann, Of Germany, gave some to his father and hopes to cure his
fathers Rheumatism. Once he noticed that the compounded had helped, Hoffmann created a
powder form and shared it with other chemists, physicians, and pharmacies.
Esterification is the process of reacting alcohol with carboxylic acid in order to produce
and Ester and water. Esterification can also be done through the use of alcohol and acid
anhydrides, which produces the exact same products. This is the form that we will use in order to
complete this lab.
Crystallization is the process in which the mass transfer of solute from the liquid solution
to a pure solid crystalline phase occurs. This process is how we will produce our pure solid
aspirin throughout this lab. In order to check for purity, at the end of this lab, we will use two
purity check tests. The first test being the melting point test, which uses a melting apparatus to
strategically measure the boiling point, which will then be compared to the boiling point of a
pure sample. The second test is the salicylic acid test, which checks for impurities by dissolving
a small sample of aspirin in ~1 mL of methanol. Then, 0.02 M FeCl3 is added by drops until a
color change occurs. A purple color yields impurities in your sample of aspirin.
Chemical Equation:
 Mechanism:

Objectives:
In this lab, you will
1. synthesize aspirin through crystallization
2. calculate the percent yield of aspirin
3. assess the purity of aspirin using melting point, a salicylic acid indicator, and a thin layer
chromatography

Materials List:
Analytical balance 250 mL Florence flask
10 mL graduated cylinder 100.0 mL graduated cylinder
Hot plate Thermometer
600 mL beaker Stirring rod
Buchner funnel 9.0 cm filter paper
1-hole rubber stopper Aspirator
Suction Erlenmeyer Watch glass
Rubber hose Test tube rack
Small test tube Melting point apparatus

Chemicals:
Salicylic acid
Acetic anhydride
Phosphoric acid
Distilled water
Ice
Methanol
0.02 M FeCl
 Safety:
Salicylic acid and aspirin may cause skin and eye irritation, but are basically non hazardous.
Acetic anhydride and phosphoric acid can cause bad burns. Handle these chemicals with care,
avoid breathing their vapors, and always wear safety goggles.

Procedure:
1. Using the analytic balance, measure 3.00 g of salicylic acid and place it into a 250 mL Florence
flask.
2. Measure 6.00 mL of acetic anhydride and add this to your flask.
3. Carefully add 5 to 10 drops of 85% phosphoric acid (the catalyst) to the flask and swirl gently for
a few minutes to mix the components thoroughly.
4. Add ~200 mL of tap water to the 600 mL beaker. Place the reaction flask into the water, and heat
it on a hot plate at 70C to 80C for 10 minutes.
5. After heating, remove the flask from the beaker and cautiously add 20 drops of distilled water.
6. Add 20.0 mL of distilled water and cool the reaction flask in an ice bath (600 mL beaker with ice
water). If crystals do not appear, you can scratch the walls of the flask with a stirring rod to
induce crystallization.
7. Assemble a vacuum filtration apparatus.
8. Mass a piece of 9.0 cm filter paper. Place the filter paper in the Buchner funnel and dampen it
with distilled water. Turn on the water flow for the apparatus.
9. Vacuum filter the solid aspirin through the pre-massed filter paper. Wash the crystals with 2-3
mL of chilled water. Allow the air to be drawn through the solid and filter paper for 15 minutes.
The liquid in the bottom of the flask is mostly water and can be washed down the sink.
10. Record the mass of a watch glass. Place the filter paper with the product on a watch glass. Place
the watch glass on a piece of paper with you and your partners name on it. Place the watch
glass in the drying oven. Your product will dry overnight.
11. After drying, mass the filter paper, aspirin and watch glass.
12. Check for impurities by dissolving a small sample of aspirin (~0.01g) in ~1 mL of methanol.
Then drop by drop add 0.02 M FeCl3. The appearance of a purple hue indicates salicylic acid
impurities in your aspirin. Assess the purity of your aspirin product by measuring the melting
point of the aspirin using the melting point determination procedure.

Cleanup:
Keep a small sample of aspirin in a small labeled test tube for the next lab.
Clean all glassware thoroughly. Put away any glassware used.
Data:
 The mass of objects used to calculate the aspirin obtained.
Object Mass (g)

Filter Paper 0.5309 g

Watch Glass 45.0278 g

Filter paper, watch glass, & aspirin 48.3557 g

The melting points of each trials of aspirin to test the purity.

Trial Start to Melt (C) Finish Melting (C)

1 132.4C 134.2C

2 135.6C 137.2C

3 136.2C 138.0C

The number of drops of FeCl to turn purple: 1 drop

The mass of salicylic acid used in finding the theoretical yield: 3.00 g

Analysis/Calculations/Error:
Theoretical yield:
3.00 g CHO 1 mol CHO 1 mol CHO 180.157 g CHO

138.121 g CHO 1 mol CHO 1 mol CHO

= 3.91 g CHO

Mass of Aspirin Obtained:

Mobtained = Mall three -Mwatch glass - Mfilter paper
= 48.3557 g - 45.0278 g - 0.5309 g = 2.7970 g

Percent yield:
% yield = Experimental/Theoretical yield x 100
2.7970 g/3.91 g x 100 = 71.5%
Melting Point for Each Trial:
MP = (Start Temperature + Finishing Temperature)/2
Trial 1 (132.4C + 132.4C)/2 = 133.3C
Trial 2 (135.6C + 137.2C)/2 = 136.4C
Trial 3 (136.2C + 138.0C)/2 = 137.1C
Average Melting Point:
MP = (Avg 1 +Avg 2 + Avg 3)/3
MP= (133.3C + 136.4C + 137.1C)/3 = 135.6C

Error:
Absolute Error = |Xt - Xe| = |135.6C - 135C| = 0.6C
Percent Error= Ea/Xt x 100 = 0.6C/135C x 100 = 0.4%

Conclusion:
In conclusion, we obtained 2.7970 g of aspirin which lead to a percent yield of 71.5%.
When we tested for impurities, we were only able to add one drop of FeCl before it turned
purple. We also tested the purity of our aspirin by finding the melting point. For each of the three
trials we found the melting point to be 133.3C, 136.4C, and 137.1C which gave us the average
melting point of 135.6C. Using this average and the true melting point of 135C, we calculated
our absolute error to be 0.6C, ultimately giving us a percent error of 0.4%.
Error in the lab occurred due to personal error. When we tried taking the filter paper with
the aspirin on it out of the Buchner funnel, the filter paper ripped a little bit. We did our best to
try avoiding losing any aspirin but we lost some, as we had to work around the tears. This would
have lowered our mass of aspirin obtained. This error would obviously have decreased our
percent yield since we lost some of the aspirin obtained.
After performing this lab, we were very pleased with our results. We would have liked a
higher percent yield but our percent error was nearly perfect. To improve our results, we could
have waited for the filter paper to dry before trying to take it out of the Buchner funnel. This
would have helped us avoid tears in the paper. From this lab, we learned how to synthesize
aspirin and how to find the purity of it by determining the melting point of the compound and by
the use of a salicylic acid indicator. In the real world, a drug company making aspirin could test
the purity of it in a similar way by finding the melting point.