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Chem 35.

1 - TEG

Silong, Rafaelle
Espiritu, Walter Aljhon
Tumimbang, Glenn Vincent

Experiment 1: Extraction of Caffeine from Coffee

February 11, 2014

I. Abstract
In pharmacology, a drug is a substance that is used in treatment, prevention or diagnosis of
diseases, or enhances physical or mental well-being. Some drugs are used to alter normal human body
functioning, such as in central nervous system. Also this drugs may be used for their perceived
psychological effects, which, when used in habituation, may cause addiction. In this experiment, the
psychoactive drug that is contained in most beverages is explored, that is caffeine.
II. Keywords: liquid-liquid extraction, Soxhlet extractor, coffee, caffeine, alkaloids, partition coefficient
III. Introduction
Caffeine according to News Medical is a
bitter, white-crystalline xanthine alkaloid. It is a
psychoactive drug and considered as a central
nervous system stimulant, it can ward of
drowsiness and restore alertness for a certain
amount of time. Although caffeine is widely
consumed an overdose of this drug can lead to
headaches, tremors, depressing moods, anxiety,
irritability even insomnia. This drug is usually
found in tea, soft-drinks and especially coffee.
Once you brew coffee, caffeine is
dissolved in the water along with its impurities,
the tannins. These tannins give the coffee its
dark color and bitter taste. Since the experiment
focuses on extracting caffeine the impurities
should be removed. In order to do this we make
use of different extraction methods like liquidliquid extraction, acid-base extraction and solidliquid extraction.
IV. Methodology
Using a commercial product, 20g of
finely powdered coffee was obtained and
wrapped in a filter paper placed in the Soxhlet
extractor. Ethanol was placed in a flask at the
bottom-most part of the extractor, and boiling
chips were added. Due to the absence of a

thimble A, filter paper was used as the porous


paper for the extraction to be successful. The
sample was refluxed for two hours until the
alcoholic extract (now with the impure caffeine)
was obtained. The solution was cooled to room
temperature.
After cooling, 10g of MgO was added in
70mL water. The solution was frequently stirred
under heat until the solvent has completely
evaporated. Water was once again added and
the solution was boiled one more time. A vacuum
pump was used to remove the hot solution. This
was done three times to rinse the extract.
Dilute sulfuric acid (2M) was added to
the watery extract and was boiled to evaporate at
least 2/3 of the solution. The remaining hot
extract is cooled down to room temperature. After
it was cooled, the extract was filtered three times
with 10mL chloroform in a separatory funnel. The
yellow, pale, colored solution was once again
filtered after the addition of 2mL sodium
hydroxide (2M) and 2 mL water to remove the
distinct color. The solvent was evaporated and
the crude product was obtained.
V. Results and Discussion
Caffeine is an alkaloid, a nitrogencontaining base that is used as a stimulant
known for its ability to take away drowsiness and

Chem 35.1 - TEG

return alertness in humans. Caffeine is naturally


found on cocoa, coffee beans, tea leaves, etc.

Figure1: Structure of caffeine

Decaffeination is the process of


removing caffeine from its source (thus,
beverages without caffeine is said to be
decaffeinated). Extraction of caffeine is fairly
easy because caffeine is polar and basic.
Caffeine is soluble in ethanol. However,
coffee is not entirely caffeine, tannins, which are
responsible for the brownish-black color of
brewed coffee, are added for coloration.
These impurities are removed via
liquid-liquid extraction (specifically, acid-base
extraction), where the key to extraction of
caffeine is its basicity. Tannins are soluble in
aqueous solvents while the neutral caffeine is
soluble in organic ones (i.e. chloroform). The
organic filtrates contain the desired crude
caffeine.
VI. Guide Questions
Discuss the following:
Liquid-liquid extraction
Liquid-liquid extraction involves the use of
solvents that are immiscible with each other (i.e
water and diethyl ether). The extraction also
depends on the density of the solvents being
used as it indicates which of the liquids will be
drained.

Experiment 1: Extraction of Caffeine from Coffee

Solid-liquid extraction
Also known as leaching, solid-liquid extraction
involves the use of liquid solvent to remove
solute particles from a solid
Acid-base extraction
Acid-base extraction is a type of liquid-liquid
extraction which involves the acidic or basic
properties of compounds. The methodology lies
on the assumption that organic compounds are
soluble in organic solvents but not in aqueous
ones. However, if the compound is protonated or
deprotonated, it will be rendered ionic, and thus
will be dissolved in aqueous solvents.
Why is it necessary to remove the stopper from a
separatory funnel when the liquid is being
drained from it through the stopcock?
It is necessary to remove the stopper from a
separatory funnel when the liquid is being
drained so that the pressure in the funnel will not
build up on the liquid (which causes the draining
liquid to bubble up that disturbs the stability of
the separated liquids inside the funnel). It is also
done to allow the air to push down the liquid
during draining. Failure to remove the stopper will
create a partial vacuum inside, which prevents
the flow of the liquid.
What is the purpose of adding magnesium oxide
in the extraction of caffeine?
Magnesium oxide acts as an adsorbent to the
caffeine. It is also oxidized to magnesium
hydroxide (Mg(OH)2) upon addition of water the
hydroxide. Adding this to coffee makes the
solution basic, converting caffeine to a form of
weak polarity. The base also reacts with the
acidic tannins, forming salts which can be
removed before extraction.

Chem 35.1 - TEG

What are alkaloids? What makes the isolation of


alkaloids easy versus other natural products?
Alkaloids are naturally occurring nitrogencontaining bases which have important
physiological effects such as morphine, nicotine,
quinine, and caffeine. Alkaloids are sparingly
soluble in water, but the salts formed after
reaction with acids are usually freely soluble.
Alkaloids are soluble in alcohols
Assume that the partition coefficient, K, for a
partitioning compound A between diethyl ether
and water is 3. Given 400mL of an aqueous
solution containing 12g of compound A, how
many grams could be removed from the solution
by a single extraction with 200mL of diethyl
ether?
g
solubility in organic layer (mL)
K=
g
solubility in aqueous layer (mL)
x
(
)
200mL
3 =
12g x
( 400mL )
x = 7.2g of compound A

Aniline, an amine is soluble in diethyl ether but


not in water; however, aniline is extracted from
diethyl ether with aqueous hydrochloric acid.
Explain.
Aniline is extracted from diethyl ether via acidbase extraction. The reaction of the acid to the
aniline will protonate the aniline, forming an
aqueous layer that can be separated from the
ether layer.
The equilibrium for phenol, sodium phenoxide,
sodium bicarbonate, and carbonic acid is shown
below:

Experiment 1: Extraction of Caffeine from Coffee

Phenol + NaHCO3
Na phenoxide + H2CO3
Determine the Keq for this reaction.
=

[ ][23 ]
[][3

VII. Conclusion and Recommendation


Successful extraction of caffeine from
coffee was performed in the experiment. SolidLiquid extraction through the use of a Soxhlet
apparatus was utilized in order to dissolve
desired compound from the sold sample. The
solubility of the desired compound in the solvent
is a very important factor that affects Solid-Liquid
Extraction. Magnesium oxide was added to serve
as a drying agent, minimizing impurities for the
sample. Acid-base extraction was employed to
separate tannins from caffeine. Tannins salt-out
from the solution upon the addition of sodium
hydroxide because it is acidic. Furthermore,
Liquid-liquid extraction was performed to
separate the aqueous phase from the organic
phase where caffeine is found. The efficiency of
the liquid-liquid extraction depends on the
partition coefficient.
It is recommended to increase the
number of refluxes in the Soxhlet apparatus and
to use a vacuum pump for filtration in order to
increase purity. Furthermore, to prevent the
burning of the caffeine while drying, it is
advisable to heat it using water bath.
References
Liquid-liquid extraction. Retrieved from:
http://chemwiki.ucdavis.edu/VV_Lab_Techniques
/Liquid-Liquid_Extraction

Chem 35.1 - TEG

Experiment 1: Extraction of Caffeine from Coffee

Solid-liquid extraction. Retrieved from:


http://www.che.boun.edu.tr/Courses/che302/Cha
pter%208.pdf
Acid-base extraction. Retrieved from:
http://chemwiki.ucdavis.edu/VV_Lab_Techniques
/Acid-Base_Extraction
Alkaloids. Retrieved from:
http://global.britannica.com/EBchecked/topic/156
72/alkaloid

I hereby certify that I substantially contribute to


this report,

Espiritu, Walter Aljhon

Silong, Rafaelle

Tumimbang, Glenn Vincent

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