Isolation of Caffeine from Tea

Tea leafs contain from 2 to 5% caffeine, along with cellulose, tannins, flavonoid pigments and
chlorophylls (see structures of caffeine and tannins on next page). The caffeine can be extracted from tea
using hot water. However, the tannins, pigments and chlorophylls will also be extracted into the water.
The caffeine can then be extracted from the water using methylene chloride (dichloromethane). Since the
tannins are acidic, base is added to the aqueous extract in order to ionize the tannins and insure that they
remain in the aqueous layer. Along with the caffeine, the chlorophylls (which are present only in small
quantities) will also go into the organic layer. Thus, the caffeine that you obtain after evaporating the
methylene chloride will not be totally pure. Either sublimation or crystallization can be used to further
purify the caffeine. However, we will not do that in this experiment (the caffeine is already close to pure).
Conclusion:

Question & Answers:

A. Discuss briefly the role of the following in the isolation of caffeine:

i. sodium carbonate

Sodium carbonate also a base, and it is added in the first extraction to make sure that the caffeine
remains in the free base form (that is, to prevent it from reacting with any acids that may be present).

If you do not use a base the tannins will also be extracted into the solvent (i.e. methylene chloride) used
in the subsequent extraction . The base converts the tannins into their sodium salts - being ionic these
salts are not soluble in solvents like methylene chloride so remain in the aqueous layer during
extraction. This allows purer caffeine to be extracted.

ii. sodium sulfate

Sodium sulfate serves as a drying agent in most reactions to absorb all excess water from the solution.

A. Give at least three characteristics of chloroform that make it a good extracting solvent for
caffeine.
Chloroform was chosen as the solvent because Caffeine is very soluble in this substance.
Thus, when the separatory funnel is used, the Caffeine in the tea dissolves into the
Chloroform and the rest of the tea can be discarded. This is done three times so that the
amount of Caffeine left in the discarded tea is minimized. This is followed by two
washings with Sodium Hydroxide and one with water. It is believed that the Sodium
Hydroxide weakens the attraction Chloroform has on Caffeine, allowing the Caffeine to be
isolated more easily later on.
B. How efficient is the extraction of tea leaves containing 1.0 g of caffeine with two 30-mL portions
of chloroform over that of a single step extraction (K25ºC = 8.36)?
C. What are emulsions? Why do they form during extractions? How are they minimized?
D. Why is it necessary to remove a stopper from a separatory funnel when liquid is being drained
from it through a stopcock.