The Extraction of Caffeine From

Tea
Harry Brennan
Period 3
Monday, March 20, 2017

Abstract:

The purpose of this laboratory exercise was to successfully extract caffeine from tea
leaves using simple organic extraction techniques. First, tea was brewed using a beaker and a hot
plate. This tea was then mixed with ethyl acetate and placed into a centrifuge, where it was
rotated at high speed for 4 minutes. The clear layer on top that was separated from the dark tea
was removed and placed into a test tube, and the process was repeated twice more. Sodium
sulfate was then added to this liquid until it no longer clumped. Then, the remaining liquid was
decanted into a 100 mL beaker and heated until evaporation occurred and only crude caffeine
remained. This crude substance was then put through a sublimation process when a 50 mL
beaker full of ice was rested on top of the 100 mL beaker. The crude caffeine sublimed, leaving
only pure caffeine on the surface of the 50 mL beaker. This was then weighed to determine the
mass of caffeine in the tea bag. A series of simple calculations was completed, and a value was
found. The experimental value was found to be 36.2 mg, but the theoretical value was 55 mg.
The absolute error was 19 mg, and the percent error was 35%.

Discussion:

Many drugs are found within nature, and natural resources can be utilized in order to
make certain compounds that are present in everyday life. Some of these include aspirin, derived
from willow bark, morphine/codeine, derived from the opium poppy, and perhaps the most well
known drug of all: caffeine. Caffeine is found in various plants and products such as coffee
beans, tea leaves, cacao pods, kola nuts and garana. According to legend, a Chinese emperor
discovered caffeine and its powers when he dropped leaves into hot water and created the first
cup of his “restorative beverage” - also known as tea. Another component of tea leaves besides
caffeine is catechin - a type of phenol with the properties of an antioxidant. Various catechins
and polyphenols are present in tea leaves, but the major component of all plants (including tea
leaves) is cellulose. The structure of caffeine, as well as the structure of cellulose are shown
below:

Caffeine Cellulose
In order to extract caffeine from tea, several methods are used. First, a solid/liquid
extraction must take place in order to get the solid natural product into the liquid solvent. This
can be done by simply brewing a cup of tea. This begins the process. The extraction process
selectively dissolves one or more of the mixture compounds into a suitable solvent. The solution
of these dissolved compounds is referred to as the extract. In this lab, a centrifuge is used to
isolate the caffeine from the other compounds found in the tea. A centrifuge is a device that spins
liquid samples at high speeds, thus creating a strong centripetal force that causes the denser
materials to travel towards the bottom of the centrifuge tube more rapidly than they would under
the force of normal gravity. In this lab, the centrifuge is used in order to drive the other
compounds in the tea downward, leaving a clear organic layer of liquid containing caffeine at the
top.
The lab setup for this exercise involves a variety of different apparatuses and equipment.
First, tea is steeped in a beaker on a hot plate. Ethyl acetate is added and a centrifuge is used to
begin separating the caffeine from the tea. The clear liquid collected after the centrifuge process
is eventually drained and heated over a hot plate, evaporating the liquid and leaving the crude
caffeine behind. A sublimation apparatus is then assembled, which involves a 50 mL beaker
filled with ice being placed inside a 100 mL beaker where the crude caffeine is deposited.
Sublimation occurs when the crude caffeine is heated by the hot plate, turned into a gas, and then
turned right back into a pure solid when it hits the cold surface of the 50 mL beaker. After this
process, pure caffeine is isolated from the other compounds, and calculations can be done to
determine an experimental value for the amount of caffeine in a tea bag.

Sources: http://edspace.american.edu/ap7794a/wp-content/uploads/sites/159/2015/03/Isolation-
of-Caffeine-from-Tea-Leaves-via-Acid-Base-Liquid-Liquid-Extraction.pdf,
http://www.theenglishgarden.co.uk/plants/5-drugs-derived-from-plants/,
http://vlab.amrita.edu/?sub=3&brch=64&sim=169&cnt=1

Objectives:

In this experiment, you will...

1. Extract caffeine from tea leaves.
2. 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 Na2CO3
● 2 5 mL Centrifuge Tubes
● Aluminum Foil (10 cm X 10 cm)
● Small Test Tube w/ cork stopper
● Ethyl Acetate
● Stirring Rod
● Na2SO4
● Analytical Balance
● Sand
● Beaker Tongs
● Ice
 ● Crucible Tongs
● Scoopula
● Hot Plate
● Safety Goggles
● Centrifuge
● Paper Towels
● Plastic Pipets

Safety:

● Wear safety goggles at all times.

● No open flame is to be used in organic lab. Many organic compounds are flammable.
● Balance the centrifuge carefully. An unbalanced centrifuge can cause serious harm to an
individual.

Procedure:

Part 1: Tea Extraction

1. Find and record the mass of a tea bag with tea. Record the mass of an empty
tea bag from the chalkboard.
2. 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 10 cm x 10 cm 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 IT TO BOIL OVER.
3. Carefully remove the beaker from hot plate using crucible 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.
Part 2: Ethyl Acetate Extraction
4. Add 3 mL of ethyl acetate to the solution. Gently swirl the beaker for ~30
seconds.
5. 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.
- Balance the centrifuge by putting the tubes in opposite holes.
- Centrifuge the mixture for 4 minutes.
6. 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.
7. 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.
8. After the third extraction, discard the lower dark layer down the sink with
plenty of water.
Part 3: “Drying” and Evaporating the Ethyl Acetate/Caffeine Mixture
9. Add a small amount (1/2 pea-sized) of Na 2 SO 4 to your test tube. Gently tap
the side of the test tube. 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.
10. 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.
11. After the decanting process is completed, the ethyl acetate must be carefully
and slowly evaporated leaving only the crude caffeine behind. Turn the hot
plate on medium high. Hold the 100 mL beaker a few centimeters above the
surface of the hot plate and swirl the mixture in the beaker. Do not let it boil.
The solid crude caffeine will remain in the beaker.
Part 4: Caffeine Sublimation
12. 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.
13. Place the sublimation apparatus on a hot plate and begin heating on medium
heat. Fill the small beaker with chips of ice. Do not let ice or water fall into
the larger beaker.
14. 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.
15. 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.
16. Dry the inside of the 50 mL beaker using a paper towel. Record the mass of
the beaker with the caffeine on the bottom. Scrape the product from the
beaker into a small test tube and cork it. Keep the caffeine for the TLC lab.

Source: “The Extraction of Caffeine from Tea” Lab Handout

Cleanup:

● Discard the tea bags in the trash.

● Rinse the used sodium sulfate down the drain with plenty of tap water.
● Clean all glassware with soapy water, rinsing three times with tap water and
three times with distilled water. Return used equipment to its proper location.

Data:

The masses that will be used to experimentally determine the percent of caffeine in one tea
bag.
Object Mass (in grams)

Tea bag w/ tea 2.5033

Empty tea bag 0.1958

50 mL beaker w/o caffeine 29.5121

50 mL beaker w/ caffeine 29.5483

Analysis/calculations/error:

1. Calculate the mass of tea in the tea bag.

Tea bag w/ tea - Empty tea bag= 2.5033 g - 0.1958 g= 2.3075 g
2. Calculate the mass of caffeine obtained.
50 mL beaker w/ caffeine - 50 mL beaker w/o caffeine= 29.5483 g - 29.5121 g= 0.0362 g
3. Calculate the percent of caffeine in one tea bag.
Mass of caffeine / Mass of tea x 100%= 0.0362 g / 2.3075 g x 100% = 1.57%
4. Conversion of grams to milligrams:
0.0362 g / 1 g x 1000 mg= 36.2 mg
5. Percent yield:
Exp. mass of caffeine / theoretical mass of caffeine x 100% = 36.2 mg / 55 mg x 100%= 66%
6. Theoretical percent of caffeine in one tea bag:
Mass of caffeine / Mass of tea x 100%= 0.055 g / 2.3075 g x 100%= 2.4 %

Error Calculations:
Experimental mass of caffeine, percent in bag, percent yield: 36.2 mg, 1.57%, 66%
Theoretical mass of caffeine, percent in bag: 55 mg, 2.4 %

Absolute Error:

Ea = |XE - XT | = |36.2 mg - 55 mg| = 19 mg

Ea = 19 mg

Percent Error:

E% = Ea /XT x 100% = 19 mg / 55 mg x 100% = 35%

E% = 35%

Conclusions:

In this laboratory exercise, caffeine was extracted from tea leaves using simple organic
extraction techniques. We experimentally determined that our tea bag contained 32.6 mg of
caffeine, which meant that the percentage of caffeine in the bag was 1.57%. The theoretical value
for how much caffeine was in the tea bag was 55 mg, which meant that the percentage of
caffeine in the bag was 2.4%. Our absolute error was 19 mg, and our percent error was 35%.
Errors occur in any experiment, and this lab definitely contained personal error. Caffeine
could have been lost at several steps throughout the lab, such as the step when the clear liquid
was removed from the centrifuge tube, when the liquid was drained from the tube with the
sodium sulfate solution in it, or when the caffeine sublimed onto the 50 mL beaker. For example,
we may have not been as precise as possible when decanting the liquid from the test tube in
which we added sodium sulfate, leaving some caffeine behind in the tube and lowering the
result. Also, when dealing with milligrams, a very small unit of measurement, even the slightest
error can cause a large spike in percent error because of the small values.
Overall, we were not extremely pleased with the results of our lab. We had a high
absolute and percent error. In order to improve the results, we could be more careful and precise
when transferring the liquid, as well as sucking it out of the centrifuge tube. The results would
have been much closer to the true value if more time was taken to ensure all caffeine was
removed and kept throughout each step of the lab. From this lab, we learned how to use
laboratory equipment such as a centrifuge and a simple sublimation apparatus in order to extract
caffeine from a tea bag. This lab could be applied to a real world scenario, such as a
manufacturer determining how much caffeine is in a product they sell. This lab setup could be
used to determine how much caffeine is present, and the product could then be labeled and sold.