Jiara Laine Montano

1 September 2016

Chem 26AA

9 September 2016
Experiment no. 3: Extraction of Caffeine from Tea

Data and Results

Sample

Plate no. 1
Caffeine from Tea
Distance
Retardation
Factor
19 mm
0.63

Plate no. 2
Caffeine from Redbull
Distance
Retardation
Factor
0 mm
0

A (extracted)
B(extracted +
19 mm
0.63
18 mm
standard)
C (standard)
20 mm
0.67
18 mm
Table 1 Distance travelled and Retardation of Extracted Caffeine

0.6
0.6

Discussion
This experiment aimed to extract caffeine from tea. In this experiment, Sunny Selects Black
Tea was used. This type and brand of black tea contains about 61 mg of Caffeine per tea bag.
From this data, approximately 244 mg of caffeine can theoretically be extracted using
four tea bags of the said tea. However, due to some circumstances the experimental value of
the caffeine extracted (in grams) has not been obtained but it can be inferred from the other
data sets of other experimenters that the experimental value will be less than the literature
value. It is expected that the amount of caffeine extracted is less than 244 mg. However,
if approximately 100 mg of caffeine can be obtained from 4 tea bags steeped in 50 mL
water the amount of caffeine that can be extracted once with 30 mL dichloromethane is
86 mg. But if it was run 5 times with 6 mL dichloromethane the total caffeine extracted
would be expected to be 98 mg (refer to Appendix).
In this experiment, dichloromethane was used to extract pure caffeine from the steeped tea
~50 mL water. The mixture was run through a separation funnel and dichloromethane was
run over the mixture. In this liquid-liquid extraction, caffeine becomes soluble in
dichloromethane and this solution subsided to the bottom separating itself from the other
components of tea, making it possible to extract caffeine. Ideally the color of the extracted
coffee would be white, however sometimes the extracted caffeine may deviate from this
color. Deviations in color may be caused by impurities in the tea or the dichloromethane
used. The extracted caffeine can, however, be further purified by the process of
sublimation and centrifugation (Handy 2002).
This dichloromethane-caffeine solution was then tested for purity using TLC plates. During
this test ultraviolet light was used to visualize caffeine. This is because cannot normally
be seen in white light. To be able to see it, it had to be exposed to a lighting that had a
frequency and wavelength that allows caffeine to block the light hitting the plate which
in this case would be UV light. This method allows darks spots to appear in the plate.

Given this, two extracts, one from a caffeinated drink (redbull) and the other from tea, were
run through the TLC. Based from the results in table 1, the extracted caffeine can be said
to be relatively pure for the distance travelled by the extract and the standard were of
similar values. This slight deviation may have been the result of the uneven travelling of the
solvent from the baseline to the solvent front. On the other hand, the extract from the
caffeinated beverage did not have caffeine travel on the TLC plate. This is probably
because the extract dropped on the TLC was dilute and was somehow lost when the
TLC plate was developed.
This test is possible because of the separation of compounds. This is based on the
competition of the solute and the mobile phase for binding places on the stationary
phase. For example, if the stationary phase is polar, given two compounds that differ in
polarity, the more polar compound has a stronger interaction with the stationary phase
and is, therefore, more capable to dispel the mobile phase from the binding places. As a
consequence, the less polar compound moves higher up the plate (Bankhede et al. 2012).
Conclusion
From the experimental data and results, the objective of this experiment which is to extract
and determine the purity of the caffeine from tea was accomplished. Although the extraction
and purity test (TLC) was accomplished, the melting point test was not completed due to the
accidental disposal of the extracted caffeine. Nevertheless, it suggested that to further
improve the purity of the extract, sublimation and centrifugation can be done. Furthermore, it
is also suggested that distillation be done to avoid impurities from dichloromethane.
References
G., D., & A. (2014). Extraction RCS [PDF]. Department of Chemistry, Ateneo de Manila
University.
Handy, Carol. Caffeine Extraction CH2CCl2. Portland: Portland Community College, 2 Dec.
2002. PDF.
Bankhede, Hemant, Stepan, Ajay Pal Singh, and Geoffrey O. Joel. "Thin Layer
Chromatography (TLC): Principle (with Animation)." PharmaXChange.info.
PharmaXchange, 8 Nov. 2012. Web. 08 Sept. 2016.
Appendix
1. TLC Plates

Figure 1 TLC
Plates from
caffeine
extracted
from tea (left)
and Red bull
(right)

2. Calculation for the Retardation Factor (Rf)

distance travelled by the spot
19 mm
Rf =
=
distance travelled by the solvent 30 mm
3. Amount of Extracted Caffeine
Given: 100 mg caffeine; steeped in 50 mL water, 30 mL dichloromethane, KD = 10
Let: x be the solubility of caffeine in water, 10x be the solubility of caffeine
Extracted once:
50 x+10 x (30 )=100
350 x=100

x=0.29 mg/mL
10 x ( 30 )=85.71mg
86 mg
Extracted five successive times:
a.1st
110 x=100
x=0.909 mg/ mL
60 x=54.55 mg

b. 2nd
110 x=0.909(50)

c. 3rd
110 x=20.66 mg/mL
x 0.1878
60 x=11.27 mg
d. 4th
110 x=9.39
x=0.085 mg/ mL
60 x=5.12 mg

e. 5th
110 x=4.27
x=0.03881

x=0.4132 mg/mL

60 x=2.33 mg

60 x=24.79 mg

Total caffeine=54.55 mg+24.79 mg +11.27

98.06 mg=98 mg