Pupil

Experimen
t
Extraction of Caffeine
from tablets

Learner Guide

Introduction
Tea and coffee are two of the most commonly consumed drinks in the
world. The active ingredient that makes them valuable to humans is
caffeine. Caffeine is an alkaloid, a class of naturally occurring compounds
having the properties of an organic amine base.
Extraction of caffeine from tea leaves is
quite a common experiment at Advanced
Higher level – usually as a project.
Caffeine does not exist alone in tea
leaves; the leaves are mainly cellulose,
pigments and chlorophylls, and tannins.
Tannins are phenolic compounds of high
molecular weight. The acidic phenols of
tannins can complex with metals like
calcium to form solid precipitates.
Because of the various contaminants that need to be removed, extraction
from tea leaves is a little more complex and time consuming so we are
going to make the extraction from caffeine tablets.
Most traditional caffeine extractions specify chloroform (trichloromethane)
or dichloromethane. Chlorinated hydrocarbons are not good for the
environment and so we are using a greener process to extract the
caffeine.
There are a few options but we think the best one is ethyl ethanoate
(ethyl acetate) for the extraction.
The recrystallisation is simply done using hot ethanol.
Experiment
You will need
Caffeine pills (each pill contains 50mg 2 g Sodium carbonate
caffeine)
~8 g Anhydrous sodium sulphate 50 cm3 Ethyl Ethanoate
50 cm3 Ethanol Separating funnel
250 cm3 beakers (x3) 50/100 cm3 Measuring Cylinder (x2)
Bunsen burner, tripod & gauze or Evaporating dish / crystallising basin
hotplate
Filter funnel & paper Small Buchner / Hirsch funnel, filter
paper and vacuum pump.
Ice bath and ice Balance
Spatula Access to a kettle
Stirring rod 100 cm3 Conical flask and stopper
(x2)
100 cm3 beaker (x2) Cotton wool
Pasteur pipettes Clamp and stand

Instructions
1. Add 50 cm3 of boiling water (from a kettle) to 10 caffeine pills in a
250 cm3 beaker.
2. Continue to boil, over a Bunsen burner or on a hotplate, for up to 5
minutes, stirring occasionally to ensure the pills have disintegrated.
3. Filter off the insoluble magnesium stearate into a 250 cm 3 beaker.
4. Add 2g sodium carbonate and dissolve, stirring if needed.
5. Cool the solution down in an ice bath.
6. Transfer to a separating funnel and extract the caffeine with ethyl
ethanoate (twice with 20 cm3 and then once with 10 cm3).
Do not shake too hard (a swirling action is better) as there is the
possibility of creating an emulsion. This may separate on standing
but it could take a long time.
7. Combine the ethyl ethanoate extracts in a 100 cm 3 conical flask and
add 8g anhydrous sodium sulphate to dry the solvent.
8. Preweigh the crystallising basin and record the value.
9. Decant the now dry solvent into an evaporating/crystallising basin.
Transfer this to the fume cupboard to evaporate
This will ensure that the solvent has all evaporated off before the next
part of this experiment.

The experiment can be paused here and the recrystallisation can take
place on another day if desired.

Recrystallisation of caffeine
The crude caffeine, or the caffeine sample provided can be purified by
sublimation or by recrystallization. Several solvents can be used for this
but the easiest and cheapest is ethanol.
1. Weigh the crude product.
2. Dissolve the crude caffeine in a small amount of ethanol
a. Put the container with the crude caffeine in on a hotplate, add
20 cm3 of ethanol and warm.
b. Swirl/stir to dissolve the caffeine. If it doesn’t dissolve, add a
bit more ethanol until it has.
3. Allow to cool slowly in a corked conical flask. After recrystallization
has occurred, cool the flask further in an ice bath.
4. Weigh your filter paper and record the mass.
5. Filter the chilled solution in a small Buchner or Hirsch funnel.
6. Dry in air and weigh.

Identification
Caffeine sublimes so you cannot get a boiling point. It is possible to carry
out Thin Layer Chromatography (TLC) on it.
You will need
TLC sheet cut to size if needed Ethanol
TLC solvent* Iodine crystals
1 beaker/ bottle for developing TLC 1 glass bottle with lid for visualisation
plate of TLC plate
Hair dryer
* 6 parts Water: 1 part 2 mol l-1 ammonia

Method
 1. Dissolve a small amount of caffeine in hot ethanol and spot the TLC
plate with it: a small spot near bottom of sheet.
2. Add the solvent to the beaker/bottle and run the TLC plate.
3. When complete remove the plate from the beaker and dry with a
hair dryer.

Visualisation
Place a few iodine crystals and the dry TLC plate in a small bottle and
tighten the lid. The iodine fumes will react with the caffeine to leave a
spot.
The distance travelled can be compared with pure caffeine.
To speed up the process the bottle can be placed in a beaker of hot water.
NB circle the spot with a pencil after removing from the visualisation
bottle as the iodine stain does fade over time.

Safety

Ethyl Ethanoate is a highly flammable and is an irritant to the respiratory

tract, mucous membranes, eyes and gums. Keep away from sources of
ignition.

Ethanol is highly flammable. Keep away from sources of ignition.