Name:

Section Day: Time:

Chemistry 132.L8. Isolation of Caffeine from Tea

Prelaboratory Assignment
Before coming to lab, find some information on the internet related to caffeine. You can do this via a
key word search or you may try the following web sites: http: //rtk.net/E569St32,
http: //www.meb.uni-bonn.de/Cancernet/600316.html, http: //www.ico.org/caffeine.htm,
http: //www.holymtn.com/tea/decaffeomated.htm and http://en.wikipedia.org/wiki/Caffeine. Use this
information to answer the following two questions.

1. Methylene chloride and ethyl acetate were both used at one time to remove caffeine from coffee.
Why do you suppose methylene chloride use was discontinued?

2. The supercritical carbon dioxide process for the extraction of caffeine is now the most widely used
method for food products. In your own words, explain this process. Why is it so widely used?

Introduction
Caffeine (C8H10N4O2) is an example of a class of compounds called alkaloids which are produced by
plants. Alkaloids are organic compounds that usually contain carbon, hydrogen, oxygen and nitrogen,
and are weak bases. The name alkaloid means “alkali-like”, where alkali is a base and hence refers to
these basic properties. Other examples of alkaloids include cocaine (a drug of abuse), strychnine (a
poison found in the seeds and bark of a tree), morphine (a pain killer obtained from opium), piperine
(found in black pepper), and quinine (found in Cinchona trees; added to tonic water; used to treat
malaria). It is clear that some alkaloids are beneficial, while others are extremely harmful.

Figure 1. Chemical structure of caffeine (C8H10N4O2) .

O
CH 3
H3C C
N C N
C C C
O N N H

CH 3
Caffeine is found naturally in tea, coffee beans, and kola nuts with concentration levels between 2
and 5 %. As most of you are aware, caffeine is a stimulant. Consequently, it is present in many over-
the-counter pharmaceutical products. Caffeine also has some undesirable side effects, such as an
increase in the heart rate, nervousness, restlessness, and insomnia. One can become addicted to caffeine,
resulting in physical dependence to this chemical.

In this experiment we will extract caffeine from tea leaves using an aqueous solution of sodium
carbonate and ethyl acetate. The sodium carbonate prevents the extraction of acidic compounds called
tannins from the tea leaves. Caffeine is more soluble in the organic solvent

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ethyl acetate than in water, so we will extract caffeine into the organic solvent to separate it from
glucose, tannins, and other water soluble compounds using a separatory funnel. Any water that remains
in the organic solvent will be removed using a drying agent called sodium sulfate. We will then boil off
the organic solvent to isolate unpurified (crude) caffeine. Lastly, we will calculate the rough percentage
of caffeine in the tea leaves.

Experimental

Obtain 4 tea bags and a 400 mL beaker. Tare the balance with the beaker, remove the strings from
the tea bags and determine the mass of the tea + tea bags. Subtract the approximate mass of the tea bags
(given by instructor) from this mass to determine the mass of the tea. Write down the mass of tea below.
→Mass of tea + tea bags g
→Mass of tea bags g
→Mass of tea g
Add 250 mL of water and 5 g of sodium carbonate (Na2CO3) to the beaker containing the tea and heat
the mixture to boiling. The mixture must boil for 15 minutes. Watch it carefully to make sure that it
does not boil over. Allow the mixture to cool for 5 minutes, add ice directly to the beaker to cool the
mixture to room temperature. At this point, remove the tea bags from the mixture and discard them in
the trash can. Add 50 mL of ethyl acetate (CH2Cl2) to the tea solution. Warning: ethyl acetate is a
volatile, toxic organic solvent. Keep open containers of this substance under the hood.
Rinse the separatory funnel at least five times with water to ensure that no soap from the previous lab
section remains. Pour your mixture into the separatory funnel. Place the glass stopper in the funnel and
gently tip the funnel upside down, making sure to hold the stopper in place. While the funnel is upside
down, open the stopcock to release the pressure. Warning: do not point the funnel at anyone. Close
the stopcock and set the funnel back on the ring. The ethyl acetate (organic) layer is the upper layer and
the water layer (aqueous) is the bottom layer. Once the layers have separated, open the stopcock to
collect as much of the aqueous layer in a 400 mL beaker as possible. Then drain the solvent layer into a
separate 400 mL beaker and set aside. Pour the aqueous layer back into the separatory funnel.
Add 50 mL more ethyl acetate to the funnel. Gently invert it as described above, vent it, and collect
the organic layer in the same 400 mL beaker and then drain the organic layer into it’s collection beaker.
Once again, pour the aqueous layer back into the separatory funnel. Repeat this procedure again with
another 50 mL of methylene chloride.
Leaving the organic extracts under the hood, carefully add 5 grams of sodium sulfate (Na2SO4) to the
solution to remove any water present in the solution. You may use a spatula or glass rod to push the
sodium sulfate onto droplets of water on the sides or top. Wait five minutes, and the solution should
appear clear (not brown and cloudy) if all of the water has been removed. Get help from your instructor
if your solution is still brown and cloudy.

Pre-weigh a clean, dry 250 mL beaker with two boiling chips. Record the mass below. Using a
funnel and filter paper, filter the liquid into the pre-weighed beaker. The solid and filter paper can be
thrown away in the trash.
Boil off the solvent by applying heat to the beaker. Ethyl acetate boils at a relatively low temperature
(77°C), so you do not have to apply a lot of heat (in other words don’t put the hot plate on high). Watch
the beaker carefully as you boil it down to make sure you do not burn the caffeine. While you are
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waiting, clean up your work station, putting the solids in the trash can and washing out the funnel with
soap and water. Rinse the funnel thoroughly with water to rinse out any residual soap.
When the solvent has been evaporated, remove the beaker from heat. Reweigh the mass of the
beaker and calculate the mass of your caffeine.
→Mass of beaker + boiling chips g
→Mass of beaker + chips + caffeine g
→Mass of caffeine g

Questions

1. Calculate the approximate percentage of caffeine in your tea, using the mass of the crude caffeine
isolated and the mass of tea leaves added to the beaker.

2. Why is the ethyl acetate layer above the water layer?

3. Do you think your final mass of caffeine represents all of the caffeine originally in your tea leaves?
List two places where you could have “lost” some of your final caffeine (not including human error).

Ethyl acetate, also known as acetic acid ethyl ester, ethyl ethanoate, or
Ethyl acetate
acetic ester, is a clear, flammable liquid with a characteristic, not
unpleasant smell like certain glues or nail polish removers. From the
chemical point of view it is an ester with formula: CH3COOCH2CH3. It

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may be formed (along with acetic acid) as a contaminant in wine that has General
been exposed to air. Ethyl acetate is used as a solvent in glues and nail Systematic
Ethyl acetate
polish removers, in chemical reactions, and for extractions. Ethyl acetate name
is a non-polar (lipophilic) to weakly polar (hydrophilic) aprotic solvent acetic acid ethyl
with an 8% solubility in water. Ethyl acetate is not stable in the presence ester
Other names
of strong aqueous bases and acids. ethyl ethanoate
acetic ester
Properties Molecular
C4H8O2
formula
Esters generally are not very soluble in water, they are quite volatile as
SMILES C1=NC=CC=C1
they cannot undergo hydrogen bonding due to lack of -OH groups. Ethyl
Molar mass 88.11 g/mol
acetate can dissolve up to 3% water and has a solubility of 8% in water at
Clear, colorless
room temperature. At elevated temperature its miscibility with water is Appearance
liquid
much higher. CAS
[141-78-6]
[edit] number
Other uses Properties
Ethyl acetate is a very effective poison for use in insect collecting and Density and 0.897 g/cm3,
phase liquid
study (entomology). In a jar charged with ethyl acetate, the vapors will
Solubility in 8.3 g/100 ml (20
kill the collected (usually adult) insect quickly without destroying it. It
water °C)
also keeps the insect soft enough to allow proper mounting suitable for a
Solubility in
collection. ethanol,
[edit] acetone,
Miscible
diethyl
Chemistry ether,
Ethyl acetate is an ester that is synthesized from acetic acid and ethanol benzene
in the presence of strong acids like sulfuric acid in an esterification Melting −83.6 °C (189.55
reaction. The two reactants and the H2SO4 catalyst are heated under point K)
reflux for approx. 40 min. Boiling 77.1 °C (350.25
point K)
CH3CH2OH + CH3COOH → CH3COOCH2CH3 + H2O Critical 250.11 °C
temperature (523.26 K)
Because the reaction is reversible and produces an equilibrium, yield is Viscosity
0.426 cP at 25
low unless driven to the right by removal of water. The yield can also be °C
increased by using an acid chloride, acetyl chloride (CH3COCl), instead Structure
of the carboxylic acid. This is usually performed in the presence of a base Dipole
1.78 D
such as pyridine (to remove HCl) and since it does not result in an moment
equilibrium more of the ester is produced. It is unstable in the presence of Hazards
strong bases like sodium hydroxide or strong acids like hydrochloric acid, MSDS External MSDS
and it is hydrolyzed back into ethanol and acetic acid, especially at Main Flammable (F),
elevated temperature. hazards Irritant (Xi)

From: http://en.wikipedia.org/wiki/Ethyl_acetate NFPA 704

Flash point −4 °C

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Instructor’s Notes

Materials (per 20 students)

20 400 mL beakers
10 250 mL beakers
40 Tea Bags Note: The yield of caffeine is better with fresh tea because caffeine is lost by
sublimation.
50 g sodium carbonate
100 g sodium sulfate
10 separatory funnels (the ones with glass stopcocks leak very badly)
10 funnels with filter paper
Stopcock grease
3.0 L of ethyl acetate
Ice

Comments: If the students wash the separatory funnel with soap, make sure they rinse the funnel
thoroughly with water. If they do not get all of the soap out of the funnel, their mixture will not
separate very well and they will waste a lot of time waiting for separation. If they do have problems
with separation, you can have them separate the separated layer using the funnel a second time. You can
also add much more than 5 g of Na2SO4 to “dry” the ethyl acetate.

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