Experiment 2: Caffeine from Tea

Objectives:
1. Isolation of caffeine from tea by solid-liquid, followed by liquid-liquid extraction.
2. Purification of the product by sublimation or recrystallization
Introduction:
Caffeine is a member of the class of compounds organic chemists call alkaloids.
Alkaloids are nitrogen containing basic compounds that are found in plants. They usually taste
bitter and often are physiologically active in humans.

Caffeine is thought to act on the brain by blocking adenosine receptors. Adenosine, when
bound to receptors of nerve cells, slows down nerve cell activity; this happens, among other
times, during sleep. The Caffeine molecule, being similar to Adenosine, binds to the same
receptors but doesn't cause the cells to slow down; instead, the Caffeine blocks the receptors and
thereby Adenosine action.

Choosing extraction conditions for isolation of a product from its natural source depends
on both the properties of the compound and the composition of the source. In our case caffeine is
soluble in both water and organic solvents. It is possible to extract caffeine from leaves by

solid/liquid extraction to hot water. The medium polarity of caffeine implies that it can be further
separated from water soluble compounds by extraction to a polar non-protic solvent.
The basic N in caffeine can be used to increase or decrease its water solubility. Acidic
conditions will form the conjugate acid salt giving caffeine increased water solubility as a cation.
On the other hand if caffeine is in a basic environment it takes the neutral form and is only
somewhat polar.

Apparatus: Erlenmeyer flask, separatory funnel, Whatman No. 4 filter paper,

dichloromethane, Rotary evaporator.
Materials: Tea leaves, Calcium carbonate, cotton wool, anhydrous magnesium sulphate,
Petroleum ether.
Procedures:
Isolation of caffeine:
1. Tea leaves were weighted with calcium carbonate powder and water were bring to a
gentle boil.
2. Filter the tea leaves while still hot and then placed the filtrate into an ice-water bath.
3. Sodium chloride was added and the solution was extracted with methylene chloride
(dichloromethane).
4. The lower layer was collected (organic layer) and treated the organic layer with
magnesium sulphate.
5. The aqueous layer was extracted with methyl chloride. The organic layer was collected
and added anhydrous magnesium sulphate.
6. The organic layer was filter using a small piece of cotton wool into a pre-tared roundbottom flask.
7. The solvent was removed using rotary evaporator and product was weighted and
percentage yield was calculated based on the amount of tea originally used.

Purification of caffeine by sublimation:

1.
2.
3.
4.

The crude caffeine was placed into a petri dish.

The petri dish was placed on a hotplate and covered with 3 disks of filter paper.
The petri dish was covered by beaker containing 30-50ml of water.
After few minutes white vapours of caffeine inside petri disk and sublimated on the filter

paper.
5. After 5 minutes the heat was turned off and the system was left to cool down at room
temperature.
6. The purified caffeine was weight and calculated.
Results & Calculations:
Table 1:
Isolation of Caffeine
Tea leaves

10.0000g

Empty round bottom flask

150.0489g

Round bottom flask + Crude Caffeine

150.1796g

Crude caffeine

0.1307g

Table 2:
Purification of Crude Caffein
Watch glass + Filter Paper

32.7210g

Watch glass + Filter Paper + Purified

32.7924g

Caffeine
Purified caffeine

0.0714g

Percentage yield of extraction:

% yield = Mass of crude caffeine
Mass of tea leaves
= 0.1307g / 10g x 100%

x 100%

= 1.31 %
% Recovery of the sublimation
% yield = Mass of purified caffeine x 100%
Mass of crude caffeine
= 0.0714g / 0.1307 x 100%
= 54.62 %

Melting point of caffeine obtained after sublimation : 231C -233 C

Literature melting point of caffeine : 236 C
Colour of the product : Pale Yellow
Shape of Crystals

: Pale yellowish amorphous solid

Table 3:
IR spectra of:
Pure caffeine
N-H stretch
C-H stretch
N-H bend

Synthesized caffeine
3110 cm-1
2955 cm-1
1663 cm-1

N-H stretch
C-H stretch
N-H bend

3110 cm-1
2953 cm-1
1655 cm-1

Discussion:
In this experiment, the water soluble substances in tea leaves were extracted using hot
water. Sodium carbonate is added to the extraction medium is to ensure that the acidic substance
remains water soluble and that the caffeine will be present as the free base. Due to some of the
compounds in the tea leaves are also soluble in dichloromethane. So, by adding sodium

carbonate to the solution, formed insoluble tannin salts which can be removed from the solution
before the caffeine is extracted.
The dichloromethane extract primarily contained caffeine with small amounts of
impurities. This is because Caffeine is also water soluble, but by keeping washing with basic
solution can minimizes the caffeine lost, while maximizing the removal of impurities.
After extraction and evaporation the caffeine, the crude caffeine collected still contains of
impurities. One of the method is to purify the crude caffeine through purification which based on
the ability of caffeine to sublime. Sublimation is the ability to pass directly from solid state to the
vapor state and condense back to a solid form without passing through liquid phase.

Since the impurities in crude caffeine extract do not sublime under the same condition as
caffeine, sublimation will result in pure caffeine.

Form the IR spectrum obtained for both pure caffeine and synthesized caffeine. Both of it have
similarity where pure caffeine and synthesized caffeine have N-H stretch at 3110cm -1 and
3110cm-1, C-H stretch at 2955cm-1 and 2953cm-1, N-H bend at 1663cm-1 and 1655cm-1
respectively.

The percentage yield of the crude caffeine form the tea leaves is 1.31% where the
percentage yield of the purified caffeine from the crude caffeine is 54.62%.

Conclusion:
The extraction of the caffeine from the tea leaves can be done by using solid-liquid
followed by liquid-liquid extraction and purified by using sublimation method. The percentage
yield of the crude caffeine form the tea leaves is 1.31% and the percentage yield of the purified
caffeine from the crude caffeine is 54.62%.

Bibliography
Anon., 2014. Caffeien Boiling and Melting Points. [Online]
Available at: http://chemistry.stackexchange.com/questions/7426/caffeine-boilingand-melting-points
[Accessed 24 June 2014].
Anon., 2014. Isolation of Caffeien from Tea. [Online]
Available at: http://science.csustan.edu/almy/3012/caffeine.htm
[Accessed 23 June 2014].
Odinity.com, 2014. Odinity Organic Chemistry Lab. [Online]
Available at: http://www.odinity.com/caffeine-isolated-tea-bags/
[Accessed 24 June 2014].