Experiment title: Extraction of

caffeine from Tea

Lebanese American Uni

Aim of the experiment:
The aim of this experiment is to separate caffeine present in tea by liquid-liquid extraction using
DCM (dichloromethane CH2Cl2) as extraction solvent in order to deduce the percentage of caffeine
in tea.

Experimental:
5 g of already weighed and wrapped dry tea leaves in cheesecloth bag were put in a 400 ml beaker.
Then, 150 ml of distilled water were measured using a graduated cylinder then added to the beaker.
20g of Na2CO3 (sodium carbonate) that were already weighed on a balance using a weighing boat
were added to the tea and water in the beaker. After that, the beaker was placed on a hot plate, the
heating was set to maximum and the solution was left to boil for 10 to 15 minutes. After that, the
heating plate was turned off and the beaker was placed on the bench.
Then, the setup for extraction was prepared. An O-ring was clamped to a stand in order to support
the separatory funnel. The separatory funnel was cleaned using distilled water and it was made
sure that it does not leak and that it has the right cap by testing if it was working well before it was
used in the experiment. The solution in the beaker was transferred into the separatory funnel which
was placed on the O-ring which was fixed on a metal stand.
After the extraction, the solution in the separatory funnel was discarded and the funnel was washed
and dried, while the solution in the Erlenmeyer contained at that step only caffeine and DCM. The
next step was to add one spatula of MgSO4 (Magnesium Sulfate), the drying agent to the solution in
order to absorb excess water drained in the organic solvent. The dried extract was decanted into a
clean, dry and pre-weighed 50 mL beaker of 27.66 g, which was placed on a hot plate under the
fume hood for evaporation. After the DCM had evaporated, the caffeine was extracted. The beaker
containing the remaining caffeine was left to cool then weighed on an organic balance, and the
results were recorded afterwards (mass of the beaker+ caffeine=27.67 g) . The mass of the beaker
containing caffeine was compared to the initial mass of the beaker without caffeine.
The masses obtained were used to find the %recovery of the caffeine in the tea leaves.

Results:
Mass of Tea Bag 5g

Mass of Empty Beaker (organic 27.66 g

balance)

Mass of Beaker + Caffeine 27.67 g

(organic balance)

Mass of Extracted Caffeine 0.01 g

The tea bags have been already weighed and found to be 15g.
The mass of extracted caffeine is found by comparing the mass of the beaker when empty and when
containing the caffeine
Mass of Caffeine=Massbeaker +caffeine −Massbeaker =27.67−27.66=0.01 g
The % recovery of caffeine is found by dividing the mass of the extracted caffeine (pure colorless
crystalline solids) to the mass of the whole tea bag (sample)
mass purecaffeine 0.01
% Recovery of Caffeine= ×100= ×100=0.2 %
mass tea bag 5

Discussion:
Caffeine structurally belongs to a class of nitrogen bases called purines which basicity
comes from the lone pair of electrons found around the nitrogen. Caffeine is also a weakly
polar molecule. The nitrogen present in caffeine controls solubility, knowing that caffeine is
more soluble in organic solvents (Solubility in DCM= 14g/100mL) than in water where it is
moderately soluble (2.2g/100mL). 150 ml of distilled water was measured using a graduated
cylinder for more accuracy, and then was added to pre-weighed 5 grams (about 1 bag) of
tea leaves into a 400 ml beaker.
Then, 20 grams of sodium carbonate (Na2CO3) which were also pre-weighed, were added to
the prepared solution in the flask to make the water solution basic and proceed with
extraction. During the extraction of caffeine, tannin is also extracted. Tannin, is the other
organic compound found in tea, dissolves in both water and organic solvent. Therefore,
Na2CO3 was added, which makes the medium basic. Knowing that tannin is acidic, it will
react with the basic Na2CO3, and transformed to an aqueous salt: phenolic salts by
deprotonation of the –OH group. By this method, tannin would not be collected in the
organic layer, but would be dissolved as a salt in the aqueous layer. The organic layer
would only contain caffeine. (Tannins will become only soluble in water and very soluble in
hot water).
After that, the solution was placed in a clean separatory funnel which was placed on an O-
ring after it was made sure that there is no leakage from the separatory funnel and that it
had the right cap (stopcock was in the "closed" position, where the stopcock is horizontal) .
The height of the O-ring was adjusted so it wasn’t too high for spilling to occur and so
there would be no splashing on the walls of the flask in a way that the stem of the funnel
touched the side of the receiving flask. 20 ml dichloromethane were taken in a measuring
cylinder and divided into 2 equal portions, that is because extraction is more efficient when
using small equal amounts of the solvent rather than one big volume. In fact, KD increases
when smaller volumes are used. Before using the separatory funnel, it was made sure that
it did not leak and that it had the right cap to make sure that spilling would not occur.
After adding the first 10 ml of dichloromethane, the separatory funnel was sealed using the
cap to be able to reverse it, and it was very gently swirled to decrease emulsion (the funnel
was held such as the fingers of one hand securely covered the stopper, while the other hand
gripped the bottom of the funnel). The separatory funnel was also vented by opening the
stopcock after the swirl to release the pressure inside it thus, to prevent pressure buildup.
Otherwise, the stopcock would blow out due to the buildup of this pressure, and even the
whole funnel might explode. The cap was removed and the stopcock was opened until the
meniscus of the line of separation reached the bottom of the funnel This process was
repeated after the addition of the other 10 ml of solvent.
Caffeine has hydrophobic properties and is soluble in an organic solvent. Because of that,
the organic solvent CH2Cl2 was added and two immiscible layers formed, an organic layer
and an aqueous layer. caffeine is usually a polar substance, but it becomes significantly less
polar when it is in a basic solution: caffeine has a favorable distribution coefficient in the
extraction solvent CH2Cl2. Therefore, it is soluble in dichloromethane and suspends in the
organic layer. Dichloromethane is an alkyl halide and is denser than water (having a
density of 1.33 g/ml>1g/ml of water), so it is located at the bottom of the separatory funnel.
Dichloromethane is also inert with respect to caffeine and the other compounds in tea, and
therefore would not react with any molecule. In addition, it has a low boiling point (about
40 degrees Celsius), therefore, it would evaporate quickly that’s why we directly used the
DCM after it was placed out of the fume hood without further waiting). If the solution was
not cooled before adding dichloromethane, it would have evaporated and caffeine would
not be properly extracted. Not to forget that its low boiling point allows it to be easily
removed from the extracted caffeine. In addition, DCM is very volatile (it was kept under
the hood) and it will explode in hot solutions (that is why we cooled the solution).

Emulsion is a colloidal suspension of one liquid in another, and they form because the
relative densities of the layers become too similar, taking longer for the layers to separate,
or because the relative polarities of the two layers become too similar due to the nature of
the solutes dissolved in them, finally sometimes emulsions form because the layers were
shaken too long and/or too vigorously. Usually to break the emulsion, a glass rod is used to
pop the bubbles and break up the colloidal suspension. After retrieving the organic layer in
an Erlenmeyer flask, a few brown specks remain in the clear organic solution. So, NaCl is
usually added to the flask to establish salting out effect, NaCl which is a neutral salt
changes the density of the aqueous layer. The addition of an inorganic salt into a mixture of
water and a water-miscible organic solvent causes a separation of the solvent from the
mixture and the formation of a two-phase system. This phenomenon is referred to as "salt
effect” BUT THIS WAS NOT USED IN OUR EXPERIMENT SINCE NO EMULSION
WAS FORMED (OR IT COULD HAVE FORMED AND CONTRIBITED TO SOURCES
OF ERROR BUT WE DID NOT TAKE INTO CONSIDERATION).

After the extraction, the solution in the Erlenmeyer contained only DCM and caffeine.