Organic Chemistry Laboratory Manual 1

EXPERIMENT 3. EXTRACTION AND PURIFICATION OF CAFFEINE

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A large number of organic compounds can be isolated from plants, animals and
microorganisms through extraction procedures. Extracts are complex mixtures composed of
organic compounds bearing functional groups that are of different polarities. This difference in
polarities can be exploited in order to separate these organic compounds in the mixture using
solvent extraction method (also commonly known as liquid-liquid extraction). Solvent extraction
is a separation technique based on the relative solubility of the compounds between two
immiscible solvents, usually a polar solvent such as water and a non-polar organic solvent such
as dichloromethane.

In liquid-liquid extraction, a separatory funnel is used. It is a stoppered glassware that

contains a stopcock which controls the flow of the liquid (Figure 1). The liquid extract is poured
into the separatory funnel after which an organic solvent is added. The funnel is then sealed
with a glass stopper (Note 1). After ensuring that the glass stopper is tightly in place, the funnel
is inverted by holding the stopcock with your writing hand while supporting the glass stopper
pennyhead with the other. The stopcock is opened to release the pressure build-up from the
solvent (called venting) then closed back up. The funnel is shaken to facilitate the extraction
followed by venting (see instructor’s demo). Then, the funnel is oriented upright ready for
separation of the immiscible components.

Figure 1. Solvent Extraction Set-up

Another method of separation is sublimation. This is a process wherein solid substances

pass directly into the vapor phase when heated, and on cooling, pass directly back to the solid
phase without the intermediate appearance of a liquid state. For sublimation to occur, it is
necessary that the solid has a relatively high vapor pressure at a temperature below its melting
point. Generally, sublimation is carried out under reduced pressure. It affords a method of
obtaining a product of high purity and is widely used in the isolation of compounds that readily
sublime such as many amino acids, ketones, carboxylic acids and most acid anhydrides and
quinines.

In this experiment, extraction of caffeine from coffee or tea will be performed via solvent
extraction. The crude product will be purified by sublimation and the purity of the purified solid
will be determined via melting point.

Organic Chemistry Group ● Institute of Chemistry ● University of the Philippines Diliman

Organic Chemistry Laboratory Manual 2

MATERIALS AND APPARATUS

coffee (or tea) oil iron ring/iron stand

ethyl acetate separatory funnel coffee filter
6 M NaOH thermometer filter paper
anhydrous CaCl2 rubber band hot plate

PROCEDURE

A. Extraction of Caffeine

Weigh 6.0 grams of coffee (or tea) in a coffee filter. Boil 100-120 mL of distilled water in
a 250 mL beaker. Remove the beaker from the hot plate once it is boiling and immerse the
coffee filter containing the coffee (or tea). Let it steep for 5 minutes and occasionally stir the
solution. Filter the coffee (or tea) solution using fluted filter paper and cool the solution to room
temperature.

Extract the coffee (or tea) solution three times with 20.0 mL portions of ethyl acetate.
Wash the combined organic layers twice with 20.0 mL portions of 6.0 M NaOH and once with
20.0 mL of distilled water. Collect the organic layer and dry it with small amount of anhydrous
CaCl2 (Note 2).

Transfer the organic layer in a pre-weighed 100 mL beaker and let the solvent evaporate
using steam bath (Note 3). Determine the weight and note the color of the crude product.
Calculate the % recovery and determine the melting point of the crude product.

B. Purification of Caffeine by Sublimation

Cover the beaker with pre-weighed filter paper and seal with a rubber band. Place the
beaker in an oil bath such that about 1/3 of the beaker is immersed (Figure 2). Heat the water
bath to 180 °C.

Figure 2. Sublimation Set-up

Organic Chemistry Group ● Institute of Chemistry ● University of the Philippines Diliman

Organic Chemistry Laboratory Manual 3

Continue heating for at least an hour until needle-like crystals deposit on the filter paper
and at the sides of the beaker.

Carefully remove the filter paper and weigh it together with the sublimate. Report the
weight and the % recovery of pure caffeine. Determine the melting point of the purified caffeine.

NOTES

1. Wet the glass stopper with distilled water to prevent from being stuck in the funnel.

2. Continue adding anhydrous CaCl2 until it is freely swirling in the solution.

3. The fume is highly toxic. Assemble the set-up inside the fume hood.

WASTE DISPOSAL

Dispose the coffee, tea bags and coffee filter into the trash bin. The remaining crude solid in the
beaker should be disposed in the solid waste jar.

REFERENCES

Baldwin J. 1970. Experimental Organic Chemistry. McGraw Hill Book Co.

Berger D. 2010. Organic Chemistry Laboratory Manual. Bluffton University, New York.

Boord B and Bossert R. 1949. Laboratory Outlines and Notebook For Organic
Chemistry. J. Wiley and Sons.

Horak V, Crist D. 1975. Small scale organic techniques: Filtration and crystallization. J. Chem.
Educ. 52 (10), 664.

Pasto DJ and Jonhson ER. 1979. Laboratory Text for Organic Chemistry. Prentice
Hall Inc.

Pavia DL, Lampman GM, Kriz GS and Engel RG. 1995. Introduction to Organic
Laboratory Techniques: A Microscale Approach, 2nd edition. Saunders College
Publishing, USA.

Organic Chemistry Group ● Institute of Chemistry ● University of the Philippines Diliman