The Extraction of Caffeine from Tea
An Old Undergraduate Experiment Revisited
Scott D. Murray and Peter J. Hansen1
Northwestern College, Orange City, IA 51041
For at least three decades a common undergraduate or-
ganic chemistry experiment has consisted of the extraction
of caffeine from tea leaves. The caffeine is extracted from
the tea leaves using hot or boiling water, extracted from
this aqueous solution using an immiscible organic solvent,
isolated in crude form by evaporating off the organic sol-
vent, and purified by recrystallization or sublimation. Dur-
ing the 60’s and 70’s the organic solvent of choice was chlo-
roform (J-3), while more recent organic laboratory
manuals have specified the use of dichloromethane (4-7).
Both chloroform and dichloromethane generally are recog-
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nized as having significant toxicity. Chloroform is a “con-
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firmed carcinogen” and dichloromethane is a “suspected hu-
man carcinogen” (8). A recent article reported increasing
concerns about “chlorinated organics as a class and human
health” (9). These potential hazards prompted the authors to
seek a more suitable organic solvent for use in this experi-
ment.
The initial set of criteria used in selecting an alternative
organic solvent included:
1. immiscibility with water;
2. low toxicity;
3. low cost;
4. high stability (especiallywith respect to peroxide forma-
tion); and
5. appreciable caffeine solubility.
The reasons for the first four are apparent, while the last
is necessary for a favorable caffeine partition coefficient
between the organic solvent and water. Unfortunately, we
were unable to identify a common organic solvent that met
all five of these criteria. Leggett, et al., however, reported
that the salting-out effect can be employed to reduce dra-
matically the solubility in water of some normally water-
1
Author to whom correspondence should be addressed.
miscible organic solvents (10). This suggested to us that
the first criterion above could be relaxed.
Employing the salting-out effect, a number of common or-
ganic solvents were tested and of these 1-propanol appeared
to be the most suitable. In comparison to either chloroform or
dichloromethane, 1-propanol is less toxic (8) and less expen-
sive {by a factor of two). In addition, it is stable under normal
storage conditions and readily dissolves caffeine.
Experimental
Pour 200 mL of boiling water into a beaker containing
10-12 tea bags and allow the beaker to stand for 10 min.
Decant the “tea” from the tea bags and compress the tea
bags to maximize solvent recovery. Return the tea bags to
the original beaker, and repeat this extraction twice using
50-mL portions of boiling water. Combine the aqueous ex-
tracts, cool, add sodium chloride (26 g/100 mL of “tea”) and
calcium hydroxide (~1 g), the latter to precipitate tannins.
Filter this solution using Celite, fast filter paper, and vac-
uum filtration. (This filtration may be omitted without se-
riously affecting one’s results, but the unfiltered extract is
prone to emulsion formation during the next step.)
Transfer the filtrate to a separatory funnel and extract
with three successive portions of 1-propanol (45, 35, and 35
mL). Combine the 1-propanol extracts in a flask and
evaporate off the solvent (-80% 1-propanol and -20%
water) using rotary evaporation or distillation.
Rinse the residue in the flask (mostly sodium chloride) with
two successive 10-mL portions of acetone to extract the crude
caffeine. Filter this acetone extract and carefully boil off the
acetone. The crude caffeine obtained can be purified by re-
crystallization (dissolve in 2-3 mL toluene and add hexane to
effect crystallization) or by sublimation (5-7).
Volume 72 Number 9 September 1995 851
Discussion
The purified caffeine obtained in this experiment was
identified using IR spectroscopy.
The sodium chloride concentration specified above is sig-
nificantly less than that required to saturate the aqueous
solution. If the aqueous layer is saturated with sodium
chloride, crystallization of a portion of the sodium chloride
will occur upon addition of the 1-propanol. Analysis of the
two layers of a water/l-propanol/sodium chloride ternary
system with a composition similar to that used in this ex-
periment yielded the results given in the table.
Composition of the Water/1-Propanol/Sodium Chloride
Ternary System
Aqueous Layer (%) 1 -Propanol Layer (%)
water 74 19
6 80
1 -propanol
sodium chloride 20 1
The partition coefficient of caffeine between the 1-propanol
and aqueous phases was determined to be approximately
3.7—probably lower than the corresponding values for the
chloroform/water and dichloromethane/water systems. (Using
the reported solubilities of caffeine in chloroform and in water
(11), a rough estimate of 8.3 was calculated for the partition
coefficient of caffeine between these two solvents. For the di-
chloromethane/water system a value was not established, but
one might expect a value similar to that for the chloro-
form/water system.) Nonetheless, given the conditions of this
852 Journal of Chemical Education
experiment it is estimated that approximately 80%' of the
caffeine in the tea leaves is recovered as crude caffeine.
Using a larger quantity of 1-propanol or a smaller quantity
of water would obviously increase the percentage of caf-
feine extracted from the aqueous layer, but the latter
would reduce the percentage of caffeine extracted from the
tea leaves by the water since the tea leaves retain a signifi-
cant quantity of water.
The procedures employed in this experiment do not re-
quire dry 1-propanol. The 1-propanol/water solvent mix-
ture that is recovered by rotary evaporation or distillation
can be saved and used repeatedly. This recycling reduces
both waste generation and cost. If recycled 1-propanol is
used in the procedure described above, the amounts should
be increased by about 25% to account for the dissolved
water present in this solvent.
Literature Cited
1. Helmkamp, G. K.; Johnson, H. W, Selected Experiments in Organic Chemistry, 2nd
ed.; Freeman: San Francisco, 1968; pp 157-158.
2. O’Connor, R. In The Freeman Library of Laboratory Separates in Chemistry; Bird-
whistell, R. K.; O'Connor, R. Eds.; Freeman: San Francisco, 1971; Vol. 2.
3. Pavia, D. L.; Lampman, G. M.; Kriz, G. S. Introduction to Organic Laboratory Tech-
niques; Saunders: Philadelphia, 1976; pp 58—62.
4. Williamson, K, L. Macroscale and Microscale Organic Experiments; Heath: Toronto,
1989; pp 130-133.
5. Mayo, D. W.; Pike, R. M.; Butcher, S. S. Microscale Organic Laboratory, 2nd ed.;
Wiley; New York, 1989; pp 162-164.
6. Nimitz, J. S. Experiments in Organic Chemistry; Prentice-Hall: Englewood Cliffs,
NJ, 1991; pp 61-62.
7. Landgrebe, J. A. Theory and Practice in the Organic Laboratory, 4th ed.;
Brooks/Cole: Pacific Grove, CA, 1993; pp 381-383.
8. Lewis, R. J. Hazardous Chemicals Desk Reference, 2nd ed.; Van Nostrand Reinhold:
New York, 1991.
9. Hileman, B. Chem. Eng. News 1993, 71 (16), 11-20.
10. Leggett, D. C.; Jenkins, T. F.; Miyares, P. H. Anal. Chem. 1990, 62, 1355—1356.
11. Budavari, S. The Merck Index, 11th ed.; Merck: Rahway, NJ, 1989; p 248.