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9, 2017
B.S. in Chemistry II Date submitted: Feb. 16, 2017
Experiment No. 2
ISOLATION OF CAFFEINE FROM TEA
I. Summary of Results
II. Discussion
A good application of this method is the isolation of caffeine from tea. Tea is an aromatic
beverage commonly prepared by pouring hot or boiling water over cured leaves of the Camellia
sinensis, an evergreen shrub. One component of tea is caffeine, which is a natural organic
substance. Caffeine is probably the most commonly used additive drugs. It belongs to a large
class of organic compounds called alkaloids which vary widely in structure and reactivity. All
alkaloids have a nitrogen atom that allows most of them to accept a proton and act as a base, or
alkaline substance. The name alkaloid comes from this characteristic.
In the experiment, tea leaves (Lipton Tea Yellow) were used for caffeine extraction.
Boiling chips were added in 100 ml of water being boiled in order to prevent bumping and
enable the smooth formation of bubbles in the boiling process. The temperature is kept high in
order to increase the solubility of caffeine in water. The boiling water was then poured over the
tea leaves and covered by a watch glass for a few minutes to transfer the caffeine from the leaves
into the water. The solution was then poured into a cheese cloth to separate caffeine from other
insoluble substances in the leaves like cellulose which is insoluble in water. Addition of sodium
chloride (NaCl) was part of the salting out process wherein water separated from the rest since
salt is immiscible in water for both are polar compounds. Calcium hydroxide acts as a base and
was used to precipitate out the tannic acid as calcium tannate.
In the liquid-liquid extraction of caffeine, the cooled tea extract was poured into a
separatory funnel and added with 20 ml dichloromethane (DCM). This was then inverted and
vented gently to release the pressure upon addition of DCM. In case of emulsion formations,
addition of salt is required to polarize it,causing it to be less soluble with other substances. When
layers were left to separate, the aqueous layer (clear) is on top and the organic layer (brown) is at
the bottom because it is denser. The liquid-liquid extraction was repeated twice more for
accuracy.
For the washing and drying part, 10% NaOH solution was added to the caffeine extract
inside the separatory funnel to remove acids and other impurities. The extract was then
transferred back to a flask and added with anhydrous sodium sulfate to remove traces of water
until the solution is clear with powdery compositions.
Before distilling the extract, it was decanted into a 250 ml round bottom flask and added
with few boiling chips again. Distillation is a process of separating the component or substances
from a liquid mixture by selective evaporation and condensation. The extract was heated to 40
degrees Celsius (slightly higher than the actual boiling point of DCM which is 39.6 degrees
Celsius) to assure that caffeine residue will remain in the round bottom flask. The volume of
distillate collected was 16.5 ml. The crude caffeine was rinsed with acetone and was let to
evaporate. 0.0765 grams of crude caffeine were obtained which signifies that 0.765% of the tea
sample were caffeine.
At the end of the experiment, the amount of recovered caffeine was 0.0765 grams. As
compared to the expected amount, there is quite a large difference which yielded a large
percentage of error.
III. Conclusion
The estimated amount of caffeine that can be extracted in the tea leaves sample was 275
mg; however the amount of caffeine recovered was only 76.5 mg which is very small from the
expected value. Several factors might have caused the error to be quite large such as the
emulsion formations during the liquid-liquid extraction and human errors. To avoid emulsions, it
is recommended that the separatory funnel should be swirled gently.
This laboratory experiment taught the concepts of boiling point, densities, etc. which are
important in complex chemical reactions. Also, it successfully demonstrated how extraction
works as a method of separation.
McMurry, John, 2008. Organic Chemistry (7th ed.) . Books/Col, University of Massachusetts:
Thompson Learning Inc.
SMITH, J. G., 2009. Organic Chemistry (3rd ed.) 1221 Avenue of the Americas, New York, NY
10020: The McGraw-Hill Companies, Inc.
SOLOMONS, T.W.G. & FRYHLE, C.B. 2004. Organic Chemistry (8th ed.) New Jersey: John
Wiley and Sons
VI. Calculations
X = % caffeine recovery
. ()
X= 100%
.
0.07650
X= 100%
10.0000
X= 0.7650 %
Y = % error
Y= 100%
0.2750.0765
Y= 100%
0.275
Y= 72.18 %