EXPERIMENT 1: EXTRACTION OF CAFFEINE FROM TEA BAG

OBJECTIVE
To extract the caffeine that present in the tea bag and to calculate the % yield of caffeine
extracted from the tea bag.

INTRODUCTION
The active ingredient that makes the tea valuable to humans is caffeine. Caffeine (C
8
H
10
N
4
O
2
) is
an alkaloid that consists of Nitrogen and having properties of an organic amine base. They
usually taste bitter and often are physiologically active in humans.
Caffeine is belong to the naturally occuring group compound of Xanthines. Caffeine is the most
powerful xanthenes as it can increase alertness, stimulate the rate of heart beat, increase rate
of respiration and the central nervous system. The negative effects of Caffeine are its causes
addictive, nervousness, insomnia and headache.
Caffeine does not exist alone in tea leaves as the tea leaves also composed of cellulose,
chlorophyll, and tannins. The use of solvent such as Methylene Chloride is required to separate
the caffeine from the other compound by extraction method using separating funnel.







To obtain the pure caffeine, the organic solution was attached to the rotary evaporator. The
solid left in the round bottom flask was weighed and the % yield of caffeine was calculated and
tabulated in the result.



Figure 1: Caffeine structure
PROCEDURE
The experiment was carried out by weighing the tea bag first. 50 mL of distilled water was pour
into beaker. The distilled water was being heated for 10 minutes. The tea bag was inserted into
the boiling distilled water. The distilled water was being stirred for a few minutes so that the tea
mixed well.
The solution was then being poured into 100 mL of conical flask. The solution was left out to
give time for cooling. After cool, 0.5 g of Sodium Carbonate was added into the conical flask.
The solution was filter using cotton filter and then transferred into the separating funnel.
15 mL of Methylene Chloride was added into the solution. The mixture was shakes a few times.
The mixture solution was left for the emulsion to break. The organic layer was transferred into
another conical flask. The procedure was repeated 2 times by using 10 mL of Methylene
Chloride.
Sodium Chloride was added to the organic solution. The organic solution was filter using filter
paper to remove the excess sodium chloride. Anhydrous sodium sulphate was added to the
organic solution and was filtered again.
The solution was dried by using rotary evaporator. The round bottom flask was weighed again.














RESULT
weight
Teabags weight : 2.180 g
Empty round bottom flask : 74.682 g
Round bottom flask+
caffeine
: 74.564 g
Table 1: Data of experiment

CALCULATION
Weight of caffeine extracted from tea bag:
( ) ( )
= 74.682 g 74.564 g
= 0.1180 g
Percentage of caffeine in the tea:

( )
( )

= 5.413 %

OBSERVATION
When sodium carbonate added into the tea solution, the tea solution changed its colour from
yellowish light to black.
After add 15 mL of Methylene Chloride into separating funnel contain tea solution, the mixture
form 2 layers, which are organic layer and aqueous layer.





DISCUSSION
In this experiment, the caffeine was extracted by using extraction method. First, the tea
was immersed into the 50 mL of hot water in beaker for about 4 minutes. The hot water was
control to ensure the water does not over-boil. If over-heated, the amount of water will decrease
as vaporization occur.
The solution was left cool in the conical flask. To faster the cooling process, the conical
flask surface was flow with water. This procedure must be done before adding methylene
chloride, as its have boiling point only 40 Adding Methylene Chloride into a hot solution
causes the solvent to instantly vapourized.
Next, sodium carbonate was added into the cool solution. The function of sodium
carbonate is to remove tannin from being extracted along the caffeine in extraction procedure. It
converts tannin into sodium salt, which is not soluble with solvent. The solution was filter into
separating funnel with a cotton filtration to remove any impurities.
Extraction process was done by adding Methylene Chloride into separating funnel. The
funnel was shaken and released the gas pressure to avoid explosion. After that, the mixture was
leave for a few minutes for the equilibrium between the layers achieved. There should be 3
layers, which are the organic layer, the bubble layer and the aqueous layer. Remove the organic
layer into conical flask. Repeat the procedure by do the extraction 2 times using 10 mL of
Methylene Chloride and store the organic layer in the same conical flask.
To remove bubble present in the organic solution, add a few amount of sodium chloride
until the bubble disappeared. The organic layer was filtered. Anhydrous sodium sulphate was
added to remove some excess water that present in the organic solution. It was filtered into
round bottom flask and was evaporated by using rotary evaporator at 50
The weight of caffeine extracted is 0.1180 g and the calculated % yield of caffeine extracted
is 5.413%.
There may some error occur during experiment conducted. Extraction process may lead to
the lost of the small amount of caffeine. The mixture should be leave for a long time for the
distribution coefficient between layers occurs perfectly and the equilibrium can be achieved. So,
the caffeine can go to the organic layer part.
The tea solution temperature was not cool enough. Methylene chloride boiling point is
around 39 to 40 Vaporization of solvent occurs. The tea should be cooled using ice bath.
Next, the condition of apparatus and material lead the small error. The apparatus may
contaminate and this can affect the result of our caffeine extracted. The amount of sodium
chloride added was too much and become super-saturated. As filtered, there still a little amount
of organic solution present. The use of filter paper also can affect the result of caffeine extracted
as the filter paper is a cellulose type paper, so it also absorbed some liquid.

CONCLUSION
The objective of the experiment is achieved. The % yield of caffeine in tea is 5.413 %

QUESTIONS
1. Outline a separation scheme for isolating caffeine from tea (Experiment 11A or Experiment
11B). Use a flowchart similar in format to that shown in Technique 2.










2. Why was the sodium carbonate added in Experiment?
The addition of sodium carbonate help the tannin to be extracted into the aqueous part of
water,and some of them were partially hydrolyze to form acid.

3. The crude caffeine isolated from tea has a green tinge. Why?
The green tinge is due to the chlorophylls pigments of oxidation product.

4. What are some possible explanations for why the melting point of your isolated caffeine
may be lower than the literature value (236C)?
Isolated caffeine produced in this experiment may contain impurities or other compound. Thus,
it is not 100% pure caffeine. Therefore, its lower the melting point of caffeine
5. What would happen to the caffeine if the sublimation step were performed at atmospheric
pressure?
At atmospheric pressure more heat is needed for sublimation reaction. The more the heat is
absorbed, the imperfect its separation. For a good separation, lower pressure is vital.

REFERENCES
1. D.L.Pavia, G.M.Lampman, G.S.Kriz, R.G.Engel, Introduction to Organic Laboratory
Techniques, 3
rd
ed., page 493-495.
2. T.W G Solomon, Craig B Frhyle, Organic Chemistry, 10
th
ed.
3. http://www.ask.com/question/isolation-of-caffeine-from-tea-bag retrieved at 21
st
March
2014
4. http://www.scribd.com/doc/66268460/Extraction-of-Caffeine-From-Tealeaves#download
retrieved at 21
st
March 2014
5. http://courses.chem.psu.edu/chem36/Experiments/PDF's_for_techniques/Liquid_Liquid.
pdf retrieved at 22
nd
March 2014
6. http://www.thefragrantleaf.com/caffeine-and-tea retrieved at 22
nd
March 2014