Guide questions:

Tea leaves and coffee has different caffeine percentage. The purpose of this experiment is to
know the caffeine content of tea leaves where Lipton is the brand used for the experiment. But in
order to get the percentage of caffeine from the tea it is necessary to get first the caffeine from
the tea and this was done with the use of extraction. Extraction is needed so that the compound
caffeine is separated from the other compounds of the tea. The tea leaves were mixed with water
in order for the caffeine to be liquid in form. Since the tea bags burst while in the process of
boiling it the extract was filtered with the help of cotton and funnel. Cotton was more preferred
than the filter paper because there was lesser surface area that will absorb the liquid. After the
filtration of the extract it was placed in a separatory funnel. The purpose of separatory funnel is
that it allows clear and easier separation of the two layers due to the small interface on its lower
end.
Dichloromethane is an organic compound added with the extract since it is immiscible with
water. It was used to extract the caffeine because caffeine is more soluble with DCM than it is
with water. However, The product that is collected after extraction still has many impurities.
Tannins, another compound of tea, are also soluble with DCM therefore can be considered as an
impurity. Also, water and DCM is slightly soluble in each other. So, after separating the solvents,
residual water will remain the organic layer. Vigorous shaking produces small droplets, which
significantly increases the area of contact between the two phases and speeds equilibration of the
desired compound between them. Shaking should be as vigorous as possible without causing
formation of an emulsion. An emulsion is a mixture of immiscible solvents which refuses to
separate into two distinct phase.

Purification was done due to the impurities acquired by the extraction. Tannin which was
mentioned a while ago was theimpurity acquired since it is also soluble with the DCM and in
order to clear this impurity it must be turned into a salt. It is possible to separate the tannins from
caffeine, because tannins are acidic and can be converted to phenolic salts by deprotonation of
the OH group when a base is added, (Dullo, 2008). NaOH is used to wash the extract and to
further isolate the caffeine since the tannin will bond with it and forms a salt.
After purification of the extract it is necessary to dry the caffeine. A drying agent was added to
the organic layer because dichloromethane dissolved not only the caffeine, but water as well.
The drying agent, anhydrous sodium sulphate was added to remove excess water so that a pure
sample of caffeine could be obtained after the solvent evaporated at room temperature
(Williamson, 2011).
Characterization was lastly done in order to test if the caffeine was pure.

Conclusion: Overall, a total of .065 g was obtained from a possible amount of .055 g per tea bag,
or .11 g total. The total percent recovery was 59.1 %. This number reflects on how accurate the
procedure was performed. It was not possible to obtain 100% recovery because the reaction
never goes 100 % to completion and because of material loss through transfer during the
procedure.

http://www.linfield.edu/assets/files/chem/Courses/CHEM%20321/2014-week3-4-caffeinechem321l-53ebfd7b679e5.pdf

http://spot.pcc.edu/~tjenkins/chem
%20241/labs/241%20exp/Exp6_CaffeineExtraction/EXP1_Isolation%20of%20Caffeine.pdf
Dullo, A. Efficacy of green tea extract rich in catechin polyphenols and caffeine in increasing 24h energy expenditure and fat oxidation in humans. [Online] 2008. 1040-1044. www.ajcn.org
Williamson, K and Katherine Masters. Macroscale and Microscale Organic Experiments, 6th ed.;
Brooks/Cole, 2011.