Synthesis of Aspirin

Brendon Foley and Colin Read

Period 4

Due: 5/20/16
Abstract:

In this laboratory experiment, aspirin was synthesized from three grams of salicylic acid.

In order to do this, acetic anhydride and 85% phosphoric acid was mixed together. After heating

these substances for ten minutes, distilled water was added, and it was placed in an ice bath. This

started the crystallization process. A vacuum filtration apparatus was used to wash the final

product. To assess the purity of the aspirin, 0.02 M FeCl3 was added drop by drop until it turned

purple. The melting point was also found and compared to the true value to assess the purity.

2.4652 g of aspirin was produced in the end. It took two drops of 0.02 M FeCl3 to turn the aspirin

solution purple. The melting point was found to be 135C, which was the same as the true value.

Discussion:

Aspirin is a synthetic compound that is used medically to relieve pain and discomfort. It

was developed in the 1890s by Felix Hoffman of Bayer in the form of acetylsalicylic acid.

A chemical equation that shows the reaction of salicylic acid with acetic anhydride using a

phosphoric acid as a catalyst is shown below:

 Esterification is the name for a chemical reaction in which two reactants, usually an

alcohol and an acid, form an ester as the reaction product. Displayed below is the mechanism for

the synthesis of aspirin:

Crystalization is a solid-liquid separation in which mass transfer of a solute from a liquid

solution to a pure solid crystalline phase occurs. This applies to the lab as aspirin crystallizes

from the reaction of salicylic acid and acetic anhydride with phosphoric acid. Two purity tests

that will be used are measuring the melting point and mixing aspirin with methanol and adding

0.02 M FeCl3 to observe a purple color change.

(Sources: orgchem.Colorado.edu/ csudh.edu/ ncbi.nih.gov/ bioline.org)

Objectives:

In this lab, you will

1. synthesize aspirin through crystallization.

2. calculate the percent yield of aspirin.

3. assess the purity of the aspirin using melting point, a salicylic acid

indicator, and thin-layer chromatography.

Materials:

Analytical Balance 250 mL Florence flask

10 mL graduated cylinder 50.0 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 FeCl3
 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.

13. 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 your aspirin in a small labeled test tube for the next lab.
Clean all glassware thoroughly. Put away any glassware you used.

Data:

The masses of the objects used to calculate the mass of aspirin obtained

Objects Mass (g)

Filter Paper 0.5559

Watch Glass 57.5176

Filter paper, watch glass, and aspirin 60.5387

Melting Points of aspirin used to test the purity of the substance

Trial Starting Temp. (C) Ending Temp. (C)

1 125C 132C

2 137C 142C

3 132C 138C

Number of drops of 0.02 M FeCl3: 2 drops

Starting mass of salicylic acid: 2.9849 g

Analysis/calculations/error:

Theoretical Yield:

2.9849 g C7H6O3 1 mol C7H6O3 1 mol C9H8O4 180.157 g C9H8O4

138.121 g C7H6O3 1 mol C7H6O3 1 mol C9H8O4

= 3.8933 g C9H8O4

Mass of Aspirin Obtained:

60.5387 g - 0.5559 g - 57.5176 g = 2.4652 g

Percent Yield:

Mobtained Theoretical Yield 100 = 2.4652 g 3.8933 g 100 = 63.319%

Melting Points:

Trial 1- (125C + 132C) / 2 = 129C

Trial 2- (137C + 142C) / 2 = 140C

Trial 3- (132C + 138C) / 2 = 135C

Average Melting Point:

(129C + 140C + 135C) / 3 = 135C

Absolute Error:

E a = | Xe - Xt |

= | 135C - 135C |

= 0C

Percent Error:

E % = E a / Xt 100
 = 0C / 136C 100 = 0%

Conclusion:

After running this laboratory experiment, we were able to produce 2.4652 g of aspirin.

When we tested the purity of our aspirin, we were able to add 2 drops of 0.02 M FeCl3 before it

turned purple. When we tested the melting point to also assess the purity, we got an average of

135C. This value is actually the true value for the melting point of aspirin, so we ended up with

an absolute error of 0C and a percent error of 0%.

One place where we ran into some error was when we washed the crystals of aspirin on

the filter paper. We were not able to keep the crystals in the center of the filter paper so some of it

went through the Buchner funnel and into the Florence flask. This lowers our mass of aspirin

obtained and our percent yield of aspirin.

Overall we were pleased with our results. To improve the lab, we would be more careful

when transferring the aspirin crystals onto the filter paper to keep the crystals in the center in

order to keep them from washing into the flask. From running this laboratory experiment, we

learned how to successfully synthesize aspirin from salicylic acid and determine the purity of the

end product. This lab could be applied to the real world because Bayer can use these purity tests

if they needed to find how pure their aspirin is.