EXTRACTION

Venus Tibalao, Cheene Meryll Urmatam, Abby Valdesancho,

Gian Paula Villamayor, Ramon Villanueva III and Thea Ferina Vital
Group 9 2C Pharmacy Organic Chemistry Laboratory

ABSTRACT

Caffeine, a substance usually found in coffee and tea, is considered as the most prevalent drug in the world. It has a
molecular formula of (C
8
H
10
N
4
O
2
). The aim of this investigation was to separate caffeine from tea using a single
extraction method. The said process was done by extracting the goal substance from the components of the tea only
once. In order to make the separation possible, anhydrous sodium carbonate diluted with water was added to the tea.
After disturbing the mixture, two components with different densities was visibly seen in the funnel. The denser
substance, dichloromethane, was eventually extracted from the container and was evaporated until caffeine became a
residue. 1% of percentage by weight yield of caffeine was obtained after extraction. The result of this experiment was
then compared to those groups who obtained their percentage by weight yield of caffeine using a multiple extraction
method. Apparently, the said groups achieved a higher percentage by weight yield. The comparison concluded that
multiple extraction method is a more convenient way to extract caffeine from tea because it allows more caffeine to
be extracted.

INTRODUCTION
Extraction is a method used to isolate
compounds based upon their different solubilities
in two solvents that are immiscible. There are
two techniques of extraction: liquid-liquid
extraction and solid-liquid extraction. Solid-liquid
extraction is a form of chromatography designed
to extract, separate, and/ or adsorb one or more
components from a liquid phase onto a stationary
phase. The only kind of extraction that is
performed in teaching laboratories is liquid-liquid
extraction by which a compound is pulled from
solvent A to solvent B where solvents A and B
immiscible. The said extraction is commonly
performed using a separatory funnel.

The goal of this experiment is to isolate
caffeine from black tea.

EXPERIMENTAL
A. Compounds tested (or Samples used)

Caffeine (from black tea)

Caffeine is a bitter substance (alkaloid) found
in coffee, tea, soft drinks, chocolate, kola nuts,
and certain medicines. One of its common effects
on the body includes stimulation on the central
nervous system. The said compound is the most
widely used and the most popular drug in the
world. Caffeine is called Theine when its found in
Tea but it is the same molecule (C
8
H
10
N
4
O
2
). The
chemical name of the alleged drug is 1,3,7-
trimethyl-1H-purine-2,6(3H,7H)-dione-3,7-
dihydro-1,3,7-trimethyl-1H-purine-2,6-dione.


Figure 1: Chemical Structure of Caffeine

Anhydrous Sodium Carbonate

Figure 2: Chemical Structure of Anhydrous
Sodium Carbonate

This kind of sodium carbonate lacks water in its
component.

Figure 3: Chemical Structure of Anhydrous
Sodium Sulfate

Just like the image above (Figure 3), this kind
of sodium sulfate lacks water in its component.

B. Procedure

Liquid-liquid extraction

4.4 g of anhydrous sodium carbonate was
placed in a small Erlenmeyer flask and 100 mL of
distilled water was added on the said container.
The flask was heated in a water bath until the
solid was dissolved. 10 g of tea leaves contained
in a teabag was added to the said mixture. A
flask was used to cover the vessel. The tea
mixture was then boiled on a low flame for 10
minutes.

The teabag, removed from the flask, was
squeezed by pressing it against the side of the
flask using a glass rod until all of the liquid in it
comes out. Single extraction was used to extract
the aqueous solution with 60 mL of
dichloromethane in a separatory funnel. The
solution was left to settle for 2 minutes until the
separation between two layers became visible.
The organic layer was then drained into an
Erlenmeyer flask and the aqueous layer was
eventually discarded.

The extract was transferred into an Erlenmeyer
flask containing half a spatula of anhydrous
sodium sulfate. It was then decanted into a tared
evaporating dish. The extract was evaporated to
dryness. The residue was weighed and its
percentage yield was calculated.

RESULTS AND DISCUSSION
Caffeine was extracted by utilizing single
extraction method wherein the organic solvent
and water bilayer are separated only once. The
other type of extraction, namely Multiple
Extraction Method was applied by other groups to
extract the said substance. The multiple
extraction method is actually a more efficient
way to separate the components of the tea
because more extract is acquired in this process.


Figure 4: Single Extraction Set-Up

In Figure 4, a separatory funnel containing the
two components of the extract can be visibly
seen. The upper brown component is the tea
while the orange component on the lower part is
actually dichloromethane. The latter tends to
settle down because it is denser than the tea.

After extracting the needed sample, anhydrous
sodium sulfate was used in order to soak up the
water-containing component of an unwanted
substance present in the extract.

Table 1. Data Gathered from the
Experiment

a. Weight of tea
leaves used
10 g
b. Weight of
evaporating dish
+ caffeine
115.9 g
c. Weight of empty
evaporating dish
115. 8 g
d. Weight of
caffeine
0.1 g

The method below was used to obtain the
percentage by weight yield of the extract:

Residue = (Weight of evaporating dish +
caffeine) (Weight of empty evaporating dish)
= 115.9 g 115.8 g
= 0.1 g residue (caffeine)

% by weight yield = residue (caffeine) x 100
sample (tea leaves)
= 0.1 g of caffeine x 100
10 g tea leaves
= 1% by weight yield of
caffeine

1% by weight yield of caffeine was acquired
through a single extraction process by dividing
the residue by the sample and multiplied all over
100. Other groups who made the multiple
extraction process obtained a higher percentage
(12% by weight yield was obtained by Group 1).
The comparison of the said outcomes concludes
that multiple extraction is more efficient than
simple extraction because of the latters ability to
separate a higher amount of extract.

REFERENCES
[1] Bayquen,A.,Cruz,C., De Guia,R. Lampa,
F., Pena, G., Sarile, A., Torres,P.
Laboratory Manual in Organic
Chemistry, pp.27-28
[2]http://www.wfu.edu/chemistry/courses/organi
c/extract/extraction.htm
[3]http://chemwiki.ucdavis.edu/Reference/Lab_T
echniques/Liquid-Liquid_Extraction
[4]http://blog.myteabreak.com/2011/05/18/thei
ne/
[5]http://www.nlm.nih.gov/medlineplus/caffeine.
html
[6]http://www.druginfo.adf.org.au/drug-
facts/caffeine