Organic Chemistry CH 200L (2015-2016) Experiment 2

Extraction of Caffeine from Lipton Tea

Marco Rafael P. Lorenzo, Maynard Drury A. Tolentino, Abegail B. Velasco, and Monamiele F. Yambao*
Department of Psychology, College of Science
University of Santo Tomas, Espaa Street, Manila 1051
Date Submitted: February 23, 2016

Abstract:
In this experiment, caffeine was isolated from tealeaves through the process of solid-liquid and liquid-liquid
extraction, single and multiple extraction. With the use of single extraction, 0.0290g of caffeine was obtained. On the other
hand, using multiple extraction, 0.0165 g of caffeine was yielded. These results lead to the calculations of the percent yield.
The percent yield for single and multiple extraction are 0.45% and 0.25% respectively, based on this data the expected result
multiple extraction to yield more caffeine than single extraction was not obtained.
Keywords: Caffeine, solid-liquid extraction, liquid-liquid extraction, single extraction, multiple extraction, percent yield

Introduction
Many organic compounds are obtained from natural sources through extraction. This method
takes advantage of the solubility characteristics of a particular organic substance with a given solvent.
The mixture is brought into contact with a solvent in which the substance of interest is soluble, but the
other substances present are insoluble. Extractions use two immiscible phases to separate the substance
from one phase into the other.[1] There are two types of extraction namely solid-liquid extraction and
liquid-liquid extraction.
In solid-liquid extraction compounds are dissolved in a solvent separating them from other
compounds due to differences in properties. In the experiment water is used as solvent because it is
nontoxic, easily removed, can dissolve caffeine and nonreactive. On the other hand, liquid-liquid
extraction consists of transferring one solute to another immiscible solvent. Dichloromethane meets the
criteria to be used as solvent in liquid-liquid extraction. It is nontoxic, easily removed, can dissolve
caffeine, nonreactive and immiscible with vehicle. Under liquid-liquid extraction there are also single
and multiple extraction. Multiple extraction with small quantities of solvent are better than single
extraction with the same total volume.
Caffeine belongs to the family of heterocyclic compounds known as purines. The chemical
formula is C8H10N4O2. Caffeine has a molar mass of 194.19 grams. Caffeine can be classified as
an alkaloid, a term used for substances produced as end products of nitrogen metabolism in some plants.
Like other alkaloids, caffeine has powerful physiological effects on humans and animals. It is soluble in
water and in many organic solvents, and it appears in pure form as white crystals. Caffeine can be

prepared by extraction from natural sources or by synthesis from uric acid. Caffeine is one of the main
substances that make up tea solution. Other than tea, coffee, chocolate, and some cola drinks contain
caffeine.[2] The commercial tea sample used in this experiment is Lipton tea which contains 55 mg of
caffeine per 8 fl. oz cup.[3]
Tealeaves consist primarily of cellulose and is not soluble to water because of its high molecular
weight. Caffeine is readily soluble in hot water (extracting solvent) and is thus separated from tea leaves.
However, other complex substances such as tannins colored phenolic compounds of high molecular
weightare also soluble to water. These tannins are insoluble in organic solvent such as
dichloromethane. Caffeine is more soluble in dichloromethane. Thus, caffeine can be extracted from the
tea solution using dichloromethane as solvent and tannins are remained in the aqueous solution. The
difference in density of water and dichloromethane determines what layer should be discarded. Since
water is less dense than dichloromethane, therefore water stays above the dichloromethane which
contains the caffeine.[1]
This experiment aimed to extract and to compute the percent of caffeine from Lipton tea with the
use of solid-liquid extraction (H2O as solvent), liquid-liquid extraction (dichloromethane as solvent),
single and multiple extraction.

Methodology:
The following set-ups were used for both single and multiple extractions:

Figure 1. Set-up for solid-liquid

extraction

Figure 1. Set-up for liquid -liquid

extraction

The materials used in the experiment are the following: 3 teabags of Lipton tea, 400 mL beaker,
150 mL boiling water, separatory funnel, 60 mL of dichloromethane (CH 2Cl2), Erlenmeyer flask, 20 mL
6M sodium hydroxide (NaOH), 1 spatula anhydrous sodium sulfate (Na2SO4), evaporating dish and
water bath.
Single and Multiple extraction were performed to extract caffeine from the tealeaves. For single
extraction the following procedures were followed. The tea were removed from the bag for weighing
and was later returned in the bag. The weights were recorded. The three tea bags were then placed in a
400 mL beaker with 150 mL boiling water. The tealeaves were boiled for five minutes. Ice were added
to cool the tea extract and was transferred in a separatory funnel. The tea extract must be cooled before

the addition of CH2Cl2 to avoid the evaporation of CH2Cl2 since it has a low boiling point which is equal
to 40C.[4] Sixty (60) mL of CH2Cl2 was added to the separatory funnel. The separatory funnel was
swirled gently to avoid emulsion being formed. Once the two layers of liquid were separated, the lower
layer (CH2Cl2) was drained into a 125 mL Erlenmeyer flask. The upper layer was discarded. Lower
layer was transferred in a separatory funnel and 20 mL 6M NaOH was added. Sodium hydroxide help
remove any acids or polyphenols that were extracted along with the caffeine. [4] The separatory funnel
was again swirled gently. Lower layer was drained into a clean dry 125 mL Erlenmeyer flask. The upper
layer was discarded .One spatula anhydrous Na 2SO4 was placed in the flask with the lower layer.
Sodium sulfate serve as the drying agent. The contents were swirled and decanted. The residue of the
mixture was discarded. The decantate was transferred in a pre-weighed evaporating dish and was
evaporated over a water bath. Evaporation of the dichloromethane yields crude caffeine. Then, the
collected caffeine was cooled and weighed. The percent yield of caffeine was calculated and its
description was recorded. Same procedures were done for the multiple extraction except that 20 mL of
CH2Cl2 was added into the separatory funnel then the funnel was swirled and the lower layer was then
drained and these procedures were done for three times.

Results and Discussion:

Table 1. Results for Single Extraction of Group 11 and Multiple Extraction of Group 9 and 10

Weight of tealeaves
Weight of empty evap. dish
Weight of empty evap. dish +
caffeine
Weight of caffeine
Percent (%) caffeine
Appearance of caffeine

Single Extraction
6.3962 g
118.7896 g

Multiple Extraction
6.3769 g
116.0002 g

118.8186 g

116.0167 g

0.0290 g
0.45 %
Yellowish-white powder

0.0165 g
0.25 %
White powder

Table 1 shows that the usage of single extraction yielded 0.0290 g caffeine which is greater than
the 0.0165 g caffeine produced by multiple extraction. The data above led to the computation of its
percent yield. The percent yield of single and multiple extraction are 0.45% and 0.25% respectively. The
results obtained contradicts to the idea that multiple extraction yields more caffeine compared to single
extraction.[4] Extracting caffeine by adding dichloromethane for three separate times will obtain as much
of the pure sample. This idea can be further illustrated by the distribution coefficient principle. This
principle reasons that a larger K value (distribution coefficient) is favorable for an efficient extraction.
The use of multiple extraction yields larger K value.[5]
Caffeine is a polar molecule consists of hydrogen bonding, London dispersion forces and dipoledipole forces as intermolecular forces. Water is a polar molecule consists of hydrogen bonding. [6] Polar
compounds such as caffeine are soluble to polar solvents like water, together they form hydrogen bonds.
[7]
Caffeine is hydrophilic (water loving) molecule therefore it is attracted to water. The addition of
CH2Cl2 will break the hydrogen bonds formed by the two. [6] Caffeine has greater attraction for organic

solvents such as CH2Cl2. Tannins are present as impurities in the dichloromethane with caffeine. Phenols
such as tannins are sufficiently acidic to be deprotonated by a weak base therefore an addition of a
strong base such as NaOH extracts the tannins into the aqueous solution because hydroxide ion is
sufficiently strong base to deprotonate the tannins. Na2SO4 removes the excess water from the sample.[8]
Although Lipton tea contains 55 mg, there should be 165 mg of caffeine in the three teabags
combined it is important to consider that 100% yield caffeine is physically impossible. There is a loss of
product during the process. It was also observed that there is a formation of emulsion in the separatory
funnel that resulted to a lesser yield. Emulsions are small droplets of the organic layer that are suspended
in the aqueous that are a result of vigorous shaking of the separatory funnel. To lessen or to remove the
emulsion, a stirring rod was used to stir gently the solution.[9] In addition to emulsion there are also
human errors to be considered that led to inaccurate results.
Conclusion:
Single extraction produced 0.0290 g of caffeine. On the other hand multiple extraction yielded
0.0165 g. The percent caffeine extracted from the tea sample using single and multiple extraction are
0.45% and 0.25% respectively. In this experiment, single extraction gained more caffeine than multiple
extraction. The expected results were not obtained due to the following errors: leakage of the mixture
from the separatory funnel, formation of emulsion, inaccurate separation of the lower layer from the
upper layer and spillage of the mixture during its transfer to another container.

References:
[1] Battelheim, F. & Landesberg, J. (2001). Laboratory experiments for organic and biochemistry (4th
ed.). Forth Worth: Saunders College.
[2] Vlab.amrita.edu. (2011). Extraction of caffeine from tea. Retrieved 21 February 2016, from
vlab.amrita.edu/?sub=3&brch=64&sim=169&cnt=1.
[3]

Exis. (2016). Caffeine in Lipton tea. Retrieved from

http://www.caffeineinformer.com/caffeine-content/lipton-tea.

21

February

2016,

from

[4] Pavia, D. (2016). A small-scale approach to organic laboratory techniques. Boston, MA: Cengage
Learning
[5] Trimble, J. (2014). Isolation of caffeine from tealeaves. Retrieved from 21 February 2016, from
http://www.odinity.com/isolation-of-caffeine-tea/.
[6] Solomons, G., Frhyle, C. & Snyder, S. (2014). Physical properties and molecular structure. Organic
Chemistry. Wiley & Sons Inc.
[7] Engel, R. (2011). Introduction to organic laboratory techniques: a small scale approach. Belmont,
CA: Thomson Brooks/Cole.
[8] Mcmurry J. (2010). Fundamentals of general, organic, and biological chemistry. Upper Saddle
River, NJ: Pearson Prentice Hall.

[9] Battelheim, F. & Landesberg, J. (2010). Laboratory experiments for introduction to general, organic
and biochemistry (7th ed.). Australia: Brooks/Cole Cengage Learning.

Appendix A
Schematic Diagram of Extraction of Caffeine from Lipton Tea

Appendix B
Computation of percent caffeine from tea leaves with the use of single and multiple extraction

weight of caffeine
Percent yield =(g)
X 100
weight

of

Single Extraction
0.0290 g

Percent yield =

6.3962 g

X 100 = 0.45%

Multiple Extraction
0.0165 g

Percent yield =

6.3769 g

X 100 = 0.25%

*Corresponding Member (Yambao, Monamiele F.)