The Extraction

of Caffeine
from Tea
By: Courtney Lecker, Nick
Johnson, and Courtney
Tharp
Purpose:
The purpose of this experiment was to
extract caffeine from tea using various
extraction methods.

Discussion:
Several organic compounds of interest are produced in plants and animals as natural
products, such as the stimulant caffeine, salicylic acid, a component in the synthesis of aspirin,
and tamoxifen, an anti-cancer drug. You must be able to isolate these specific compounds from
the hundreds of other compounds in their natural resources in order to extract them. Luckily,
cellulose (figure 1) is a major component of tea leaves. Cellulose is an insoluble polymer of
glucose. Caffeine (figure 2) is water soluble. That difference in solubility can be used an
advantage when separating caffeine from tea leaves by using simple organic extraction
procedures and hot water.





Figure 1: cellulose Figure 2: caffeine
N
N
N
N
C H
3
CH
3
CH
3
O
O
O
CH
2
OH
H
H
HO
H
H
OH
H
O
H
OH
H
H
CH
2
OH
H
OH
H
O
CH
2
OH
H
H
HO
H
H
OH
H
O
O O R
O R
Objectives:
In this lab, you will...
extract caffeine from tea leaves.
assess the purity of the caffeine.
calculate the percent of caffeine in a tea
bag.


Materials:
50, 100, 400 mL Beakers 1 Tea Bag string and tag removed
10 mL Graduated Cylinder 1 M Na
2
CO
3

2 5 mL Centrifuge Tubes Aluminum Foil (10 cm X 10 cm)
Small Test Tube w/ cork stopper Ethyl Acetate
Stirring Rod Na
2
SO
4

Analytical Balance Sand
Beaker Tongs Ice
Crucible Tongs Paper towels
Scoopula Plastic Pipet
Hot Plate Centrifuge
Safety Goggles


Safety:
Wear safety goggles at all times.
No open flame is to be used in organic
lab. Many organic compounds are
flammable

Procedure:
Part 1: Tea Extraction
Find and record the mass of a tea bag with tea. Record the mass of an
empty tea bag from the chalkboard.
Place 10 mL of a 1 M Na
2
CO
3
solution in a 50 mL beaker. Place the
beaker on a hot plate.
Pinch the top of the bag with a piece of Al foil. Put the bag into the
solution, but wrap the Al foil around the top of the beaker. This will
keep the bag off of the bottom of the beaker.
Poke a small hole in the Al foil to allow steam to escape, and to add
distilled water to the solution as needed to maintain the 10 mL level.
Boil for 5 minutes. DO NOT ALLOW THE SOLUTION TO BOIL OVER.
Carefully remove the beaker from hot plate using beaker tongs. Allow
to air cool for a few minutes, then cool to room temperature quickly
using an ice bath. Remove the foil and the bag. Squeeze out excess
fluid from tea bag with crucible tongs being careful not to break the
bag. Discard the tea bag. You should have no more than 8 mL of
solution. If you have more, boil off more water to concentrate the
solution.
If you need to boil longer, make sure the outside of the 50 mL beaker
is dry before placing it on the hot plate. Be sure to cool the extract
to room temperature in ice bath.
Diagram 1:
(without the tea bag)
Part 2: Ethyl Acetate Extraction
Add 3 mL of ethyl acetate to the solution. Gently swirl the beaker
for ~30 seconds.
If the beaker is shaken vigorously, the contents may spew out.
Vigorous shaking may cause the formation of an emulsion,
which is more difficult to separate.
Add half of the solution to a 5 mL centrifuge tube, and the other
half to a second 5 mL centrifuge tube. Make sure the volumes are
exactly equal.
Be sure to balance the centrifuge by putting the tubes in
opposite holes.
Centrifuge the mixture for 4 minutes.
Remove tubes from centrifuge. Using a plastic pipet, carefully
remove the clear upper layer of liquid. Squeeze the bulb of the
pipet before putting the tip of the pipet into the liquid. Put the tip
all the way to the bottom of the clear layer and release the bulb
slowly. This will be a mixture of caffeine and ethyl acetate. Place
this liquid into a small test tube. Remove as much of the clear layer
as possible.
Pour the dark layer back into the beaker. Repeat steps 4 7
without cleaning the centrifuge tubes or the beaker. After each
extraction, be sure to pipet the clear top layer into your test tube.
After the third extraction, discard the lower dark layer down the sink
with plenty of water.

Diagram 2:
Part 3: Drying and Evaporating the Ethyl
Acetate/Caffeine Mixture
Add a small amount (1/2 pea-sized) of Na
2
SO
4
to
your test tube. Swirl gently. The crystals will clump.
Continue to add small amounts of crystals to the test
tube until the addition of new crystals does not
produce more clumping, or until you cannot add
any more to the test tube.
Using the stirring rod, decant the fluid portion of your
test tube into a 100 mL beaker by carefully pouring
the fluid along the stirring rod. Avoid getting any
crystals of Na
2
SO
4
into the beaker.
After the decanting process is completed, the ethyl
acetate must be carefully and slowly evaporated
leaving only the crude caffeine behind. Place the
100 mL beaker in a sand bath (400 mL Beaker ~1/3
full of sand) and heat to ~100C. Gently swirl the
beaker in the sand bath. Just as the solvent has
evaporated, remove the beaker. The crude caffeine
will coat the bottom of the beaker.

Diagram 3:
Part 4: Caffeine Sublimation
Assemble a sublimation apparatus as follows:
Clean and dry (inside and out) a 50 mL beaker. Record its
mass.
Place the 50 mL beaker inside the 100 mL beaker containing
your crude caffeine. This is your sublimation apparatus.
Place the sublimation apparatus on a hot plate and begin
heating. Fill the small beaker with chips of ice. Be careful not
to let ice or water fall into the larger beaker.
Continue heating until the sublimation process is complete (all
the crude caffeine is off of the outer beaker). When heated,
the pure caffeine will sublime and deposit on the outside of the
50 mL beaker. Carefully observe the sublimation process
occurring between the 50 and 100 mL beakers.
Remove the apparatus from the hot plate with beaker tongs
and allow to cool. Remove the inner beaker very cautiously
and carefully pour off the ice water making certain no water
comes in contact with the sublimed caffeine crystals.
Dry the inside of the 50 mL beaker using a paper towel. Find
and record the mass of the beaker with the caffeine on its
bottom. Scrape the product from the beaker into a small test
tube. Keep your caffeine for the TLC lab.

Diagram 4:
Data:
Mass of the teabag: 2.4738 g
Average mass of an empty teabag: 0.1749 g
Mass of tea: 2.2989 g
Mass of 50 mL beaker: 30.2057 g
Mass after sublimation: 30.2157 g
Mass of caffeine: 0.0070 g
Throughout this lab, we collected various measurements of the caffeine
and other objects to help with our calculations.
Calculations:
Finding the mass of tea in the teabag:
Mass of the teabag Average mass of an empty
teabag
2.4738 g 0.1749 g
= 2.2989 g of tea

Finding the mass of caffeine:
Mass after sublimation Mass of 50 mL beaker
30.2157 g 30.2087 g
= 0.0070 g

Percent of caffeine in one bag of tea:
(mass of caffeine/mass of tea) x 100%
(0.0070 g / 2.2989 g) x 100%
0.30% caffeine per teabag

Error:
Absolute error:
|Accepted value Experimental value|
|0.055 g 0.0070 g|
= 0.048 g

Percent error:
(Absolute error / Accepted value) x 100%
(0.048 g / 0.055 g) x 100%
= 87% error
Conclusion:
In this lab, we had to find the percent of caffeine in a teabag.
Throughout the lab, we encountered a few difficulties and
problems that could have raised our percent error. One of the
errors that occurred took place in step three. When we had to
add Na2SO4 to the test tube, we couldnt add the Na2SO4
until it didnt clump because we had too much solution in the
test tube. This would have been random error due to the
excess of the solution. This would have also raised the percent
error because the Na2SO4 wouldnt be able to accumulate as
much and dry the ethyl acetate. Another problem we had
was during step two. We had to centrifuge the solution and
pipet the upper layer. When pipetting, we couldnt extract all
of the liquid. This means we wouldnt have removed all of the
ethyl acetate, which contains the caffeine. This would have
personal error and it would raise our error by not extracting all
the caffeine.
Overall, I would say our results could have been better. This
causes us to not be pleased with our results. If we had to do it
over again, I believe we would try to centrifuge more to extract
more caffeine, and to also use a larger test tube so we
wouldnt run out of room.