Planning

1.0

Aim:

The aim of this investigation is to use three analytical methods in order to make a
comparison between the mass of acetylsalicylic acid in synthesised samples of aspirin.
Four different methods will be used to test the purity of synthesised aspirin. Through, the
best analytical method will be chosen and then used to test pure aspirin. Percentage
purity of aspirin samples can be determined by analysing the quantity of acetylsalicylic
acid. Quantitative methods such as forward titrations, backward titrations and
colorimeter will be used.

2.0

Background Information:

Acetylsalicylic acid is commonly referred to as aspirin and is an aromatic acetate with

the formula C9H8O4. Being regarded as an analgesic, anti-inflammatory and antipyretic
drug, aspirin relieves pain, reduces swelling and lowers body temperature.
Aspirin is not affected by the highly acidic conditions maintained in the stomach however
it can be hydrolysed by alkaline conditions within the intestines. This causes the
conversion of aspirin into ethanoate ions and salicylate ions.
CH3COOC6H4COOH + 20H-

CH3COO- + HOC6H4COO- + H2O

Aspirin originated in the early 1800s, when extracts of willow bark and meadow flowers
were said to relieve pain and hence resulted in the active ingredients in willow bark to be
isolated and then later identified as salicin. Although, salicin was the active ingredient in
willow bark it didnt have any pharmacological effect on individuals until the body itself
hydrolyses and oxidise it into salicylic acid.in contrast to its eventual pharmacological
effect, salicylic acid cause severe side effects including irritation to the mouths lining,
gullet and stomach. This then prompted chemists to formulate another chemical, sodium
salicylate. During trials, it showed sign of pain relief and reducing fever, however
patients began to critics the taste often causing them to vomit. It was only in the 1890s
when a German company, Bayer, discovered acetylsalicylic acid (aspirin), which caused
minimal side effect and had a reasonable taste.

3.0

Methods

3.1 Paperchromatography
1. Cut the chromatography paper to the dimensions shown below.

2. Draw a line using a pencil, 1.5cm from the bottom edge of the paper and draw another
identification mark at the top of the paper.
3. Dip a clean capillary tube into the sample of vinegar used and apply a quick gentle
touch onto the chromatography paper in order to attain a spot of no more than 0.5cm in
diameter. Allow the spot to dry.
4. Roll up the chromatography paper into a cylinder and secure it with a plastic paper
clip in a solvent, which contains 60 parts butan-1-ol, 15 parts ethanoic acid and 25 parts
water. Cover the beaker with a plastic sheer, in order to produce a saturate atmosphere.
5. Remove the chromatography paper from the beaker. Dry the paper, without
unfastening it. Spray the paper with bromocresol green solution in the fume cupboard
and allow it to dry.
6. A yellow colour should gradually appear and circle it with a pencil.
Each compound has a characteristic Rf value and hence by using this method it is
possible to identify the substances, which are added to vinegar other than ethanoic acid.
Rf= Distance travelled by compounds from original spot / Distance travelled by solvent
from original spot

3.2 Forward Titration

1. Weigh 3g of the powdered aspirin sample by putting the weighing boat on the
electronic balance and tarring it.
2. Measure 100cm3 of ethanol using the measuring cylinder and pour it into the beaker.
3. Add the aspirin to the beaker.
4. Reweigh the weighing boat to calculate how much aspirin was put into the beaker.
5. Stir the solution until all the aspirin has dissolved.
6. Use the volumetric pipette to add 10cm3 of the solution in the conical flask.
7. Add 3 drops of phenolphthalein indicator to the solution in the conical flask.
8. Set up burette and stand making sure that the burette is vertical.
9. Rinse the burette with a small amount of sodium hydroxide.
10. Use funnel to fill the burette with sodium hydroxide at eye-level, making sure the tap
is closed. Record the initial value.
11. Run the sodium hydroxide into the aspirin solution in the conical flask drop by drop
until the colour changes to the first permanent pink colour. Check the pH of the solution
after each drop using a pH meter. Record the final volume of sodium hydroxide.
12. Calculate the titre value correct to 2 decimal places.
13. Repeat the titration until three concordant results are obtained, all within 0.1 cm 3 of
each other.

14. Repeat the same procedure for other samples of aspirin.

Information required:
1.
2.
3.
4.
5.

Molar ratio of the reaction

Volume of acid
Concentration of acid
Volume of base
Concentration of base

Moles= concentration (moldm-3) * volume (dm3)

Therefore concentration of acetylsalicylic acid can be calculated once titration is
complete. From this, the number of moles and mass of acetylsalicylic acid can be
calculated. This will give the mass of aspirin present and hence the percentage purity
can be derived.

3.3 Backward Titration