13/03/2021

Organic Chemistry Lab

Dr. Ghada Al Kadamany

Assignment 2: Caffeine Extraction

Spring 2020-2021
Section 11

By:
Leen Hamdash – 202001797
Mohamad El Atat – 202001902
 Caffeine extraction
Caffeine is a colorless, crystalline solid molecule found in more than 60 plants
naturally, and in manufactured products. Structurally, caffeine belongs to a class of
nitrogen bases called purines, and so, caffeine has two heterocycles. Also, caffeine
has a high melting point with a narrow range (235 -236 ℃) and is moderately
soluble in water (2.2 g/100 mL). However, it has a dramatic increase in solubility
when the solvent is changed into an organic solvent (i.e. Solubility in DCM = 14
g/100 mL), so a successful extraction relies on the big difference in the solubility
of caffeine in water and organic solvents.
Tea has caffeine, tannins (high molecular weight phenolic compound, soluble in
water), cellulose (insoluble in water), and chlorophyll. For caffeine to be extracted
from tea leaves, the following steps must be done. First, 15g of dry tea leaves are
wrapped in a cheesecloth bag. Then, the teabag is placed in a 600 mL beaker filled
with 150 mL of distilled water. 10g of sodium carbonate is added to the mixture.
Sodium carbonate is a basic compound; therefore, it is added to the mixture in
order to deprotonate the tannins and convert them into their salt which will be left
behind in the water. The mixture is heated on a hot plate, or Bunsen burner, till
boiling and left under boiling for 20 minutes in order to maximize the extraction of
water-soluble components; the insoluble cellular material will be left behind. Now
the extracted water solution from the tea leaves is obtained, the teabag is removed
and squeezed, and the mixture is left to cool at room temperature. The mixture is
then transferred to a separatory funnel. Now, 15 ml of DCM is added for the
exclusive extraction of caffeine. After that, the mixture is shaken gently to avoid
emulsions. To enhance the separation, sodium chloride (NaCl) is added to the
mixture in the separatory funnel which will allow the aqueous layer to be saturated
with salts, and so Caffeine will be further driven to the organic layer. The step of
the extraction is repeated twice for efficient extraction. Afterward, the drained
DCM extracts are combined in a 100 ml Erlenmeyer flask and sodium sulfate
(Na2SO4), a drying agent, is added to absorb the suspended water droplets in the
DCM layer. The drying agent is then filtrated and DCM. The solution is decanted
into a pre-weighed beaker (35.08 g). Then, DCM is left to evaporate in a boiling
water bath under the fume hood. Now, 35.63g of caffeine solid is left at the bottom
of the container. The crude caffeine will be recrystallized for purification from hot
ethanol and its melting point will be measured to confirm its identity and purity.
Questions:

1. Mass of recuperated caffeine = Final Beaker Mass – Pre-weighted Beaker Mass

= 35.63 – 35.08
= 0.55 g
15g of dry tea  0.55g caffeine
100g of dry tea  Xg of caffeine
X=3.67g of caffeine found in 100g of dry tea

2. It is not possible to use alcohol instead of dichloromethane as an extraction

solvent in this experiment because water and ethanol are miscible in all
proportions, so there will be a solution of caffeine in a water-ethanol mixture,
along with the other water-soluble components of the tea, and there would be
only one liquid layer, so separation of the layers would not viable in this case.

3. Pressure builds in the funnel as solvent evaporates into the headspace and
contributes additional vapor to the initial 1 atm pressure in the funnel especially
with highly volatile solvents, like ether or DCM. In order to safely release the
pressure, the system is periodically vented.

x
20
4. 3.2= 5−x ; x=1.95 g
100
5-x=3.05, so 3.05 g of O.C is remaining and another 20ml of diethyl ether is
used
y
20
3.2= 3.05− y ; y=1.2 g, 1.2 g of O . C is extracted second time
100
Total amount extracted is 1.2+1.95=3.15g

5. Separatory funnels function on the principle that immiscible liquids will

separate from each other naturally along with their solutes, creating different
layers of solution-solute. These layers can be separated by draining them from
the separatory funnel using the stopcock to control the flow.