Experiment No.

1: Extraction of Caffeine from Coffee

Beatrice Emmanuelle Garcia│Shaine Dominique Santos│Marc Ralph Solomon
Submitted on March 31, 2017
ABSTRACT
Extraction of natural products is made possible by solvent extraction which employs the ability of a solute (organic
or inorganic) to distribute itself between an aqueous solution and an immiscible organic solvent (Rydberg, et al., 2004). This
important method, generally, involves a selective separation of the components in a mixture based on their relative
solubilities in two different immiscible liquids (Roy, 2015). In this experiment, three types of extractions were performed in
order to obtain a pure sample of caffeine from powdered coffee, since it exist together with tannins, undecomposed
chlorophyll, and other impurities. Soxhlet extraction using ethanol as solvent was first done to separate the organic
constituents from the crude sample. In order to dehydrate the resulting solution, magnesium oxide was then added to adsorb
the organic constituents from the solvent. Tannin salts were formed by acid-base base extraction using sodium hydroxide.
These salts, which are insoluble to organic solvent, were subsequently removed by evaporation of the aqueous layer to
which the salts were dissolved. Finally, the caffeine remained in the solution was extracted through liquid-liquid extraction.
White, crystalline powdered solids were isolated after the extractions. Using an infrared spectroscopic analysis, the isolated
substance is identified and confirmed to be caffeine. Calculations also showed that the percentage weight of the isolated
caffeine is 1.315%, while its yield relative to the theoretical yield is 93.93%. Thus, the different extractions that were used
to separate the constituents of coffee are efficient for isolating caffeine in its pure form.

Keywords: solvent extraction, extraction, caffeine, Soxhlet extraction

I. Introduction Different caffeinated products like coffee or tea have

Caffeine (C8H10O2N4), also known as 1,3,7-
trimethylxanthine or 1,3,7-trimethylpurine-2,6-dione,
is an alkaloid commonly contained in beverages such
as tea, coffee, and soda. It is also an ingredient of
some drugs. Furthermore, this substance occurs
naturally (to an extent of 4%) from tea leaves, coffee
beans, and cola nuts (Lundsberg, 1998). This
molecule exists as a bitter white crystalline solid
substance which has a melting point ranging from
234 to 236.5 C (Fieser & Williamson, 1992). The
structure of caffeine is shown below.
different caffeine levels. This can be known through
extracting caffeine from those products. Caffeine is
one of the alkaloids that are easiest to isolate, so it
can be easily through relatively simple methods. The
most common isolation technique is solid-liquid
extraction through the Soxhlet extractor wherein the
solvent is condensed and saturates the thimble
allowing the active material to be extracted. However,
Soxhlet extraction is not the only technique needed
to extract pure caffeine from the sample. This is due
to the presence of different impurities such as tannin
in the extract. Tannin is the substance that gives
coffee its brown color (Fieser & Williamson, 1992).
Both tannin and caffeine are insoluble in water which
makes it hard to isolate. To remove this impurity and
obtain pure caffeine, it is necessary to perform other
extraction techniques like liquid-liquid extraction
which depend on different solubilities and acid-base
extraction which depend on different polarities.

Figure 1. Structure of caffeine
Caffeine is the world’s most consumed legal drug
(Hopes, 1997). It is a cardiac, respiratory, and
psychic stimulant, and also a diuretic. The average
daily consumption of caffeine in the US is 300mg (US
FDA, 2012) and excessive intake of this drug may
result to restlessness, irritability, insomnia,
headaches, and muscle tremors (George, 2000;
Kamimori et al., 2000). An intake greater than 10g
may result to death.
This experiment aims to extract pure caffeine from
coffee beans by using the 3 extraction techniques
mentioned above. In addition to that, the properties of
caffeine will also be studied.
II. Methodology
To extract caffeine from coffee bean, soxhlet
extractor was used. The ground coffee beans were
placed in a thimble that was previously washed with
ethanol. The thimble was placed in the inner tube of
the Soxhlet extractor.

1 | Chem35.1 Extraction of Caffeine from Coffee

The round-bottomed flask was filled with 50 mL
ethanol and a small boiling chip. The Soxhlet
extractor was fitted in the round-bottomed flask, and
then the condenser was fitted in the Soxhlet extractor.
Rubber tubings were connected from the water
source to the condenser and another was connected
from the condenser to the sink for drainage. The
setup was placed under a heat source. The Soxhlet
extraction setup is shown below:
Figure 2. Soxhlet extraction set-up
Retrieved from http://1.bp.blogspot.com/-qBElc-
iz_ZQ/UVcPI_DqziI/AAAAAAAAA5c/UuX5dW0oroA/s640/1-s2.0-S0021967309016884-gr1.jpg
The sample was refluxed for two hours. To remove
the solvent in the sample, the extract was cooled to
room temperature and then 70ml solution of 10g
magnesium oxide in distilled water was added. The
solution was heated until the solvent has completely
evaporate. Addition of magnesium oxide prevented
the caffeine to evaporate.
Thirty milliliters of water was added to the dried
sample, and then was boiled. After boiling, the
sample was filtered through vacuum filtration. The
sample was filtered three times. After filtration, a few
drops of 2M sulfuric acid was added to the combined
extracts and was evaporated to 2/3 of its original
volume. After evaporation, it was filtered again and
then cooled. Addition of 2M sulfuric acid enhanced
the solubility of caffeine in water. These steps were
done to remove the adsorbed caffeine on the
magnesium oxide.
To remove the tannins and other impurities, three
different extractions were done. The first was liquid-
liquid extraction with chloroform. This was done three
times. The organic layer was removed, and the pale
yellow solution undergone an acid-base extraction
with 2M NaOH. The aqueous layer was removed, the
layer containing the caffeine undergone another
2 | Chem35.1 Extraction of Caffeine from Coffee
extraction with water. The aqueous layer was
removed. The organic layer containing caffeine was
evaporated to remove the solvent, and was then
dried. The dried product was recrystallized with water
to obtain a purer product. To verify this, its IR spectra
was obtained. The percent yield was calculated.
III. Results and Discussion
To be able to effectively extract caffeine from coffee,
series of different extractions are needed to be used.
The first type of extraction is solid-liquid extraction.
This is done with the Soxhlet Apparatus as shown in
Figure 2.
The powdered coffee is put into a thimble. It is
important that the coffee is finely ground or powdered
in order to have a more effective extraction due the
increase in the surface area of the sample. Ethanol is
then placed in the round bottom or boiling flask. As
the ethanol boils, its vapor passes through the tube
and into the reflux condenser. The condensed vapor
then drops into the thimble, extracting the soluble
material. Once the solution reaches the top of the fine
glass tube, it automatically siphons down to the
boiling flask, where the nonvolatile material will
accumulate. This process is exhaustive since it
indefinitely repeats, extracting more of the material.
The second type of extraction is liquid-liquid
extraction with the use of a separatory funnel as
shown in Figure 3. In order to isolate the caffeine,
chloroform is used as the organic solvent. Since
caffeine is relatively more soluble in chloroform, it is
easily transferred.
Figure 3. Separatory funnel set-up
Since chloroform is denser or heavier than the
aqueous solvent, it is drawn out first. The aqueous
layer is then extracted further to isolate most, if not
all, of the caffeine.
The third type of extraction is acid-base extraction. The recrystallized caffeine was subjected to Infrared
This is type of extraction is used to remove the Spectrometry Analysis. The spectra generated from
tannins present in the solution, consequently the spectrometer is shown in Figure 4.
removing the color. This is done through the addition
of sodium hydroxide solution, which reacts with the
acidic tannins, producing a salt that is insoluble in the
organic solvent but soluble in the aqueous solvent.
Finally, the mixture of combined organic layers is
evaporated to produce the caffeine crystals which are
then dried.
The final product is weighed to determine yield of the
product.

Table 1. Summary of measured data

Weight of powdered coffee 20.00g Figure 4. IR Spectra of Extracted Caffeine
Weight of caffeine crystals 0.263g

The spectra is then compared and matched to

According to the International Coffee Organization,
theoretical spectra of caffeine. Minor peaks in the
the percent weight of caffeine in Arabica beans is
fingerprint region signifies stretching of C-C, C=C,
from 0.8% to 1.4%.
and C-N bonds. Caffeine has 10 C-N bonds. While
Using the maximum of the range, the theoretical major peaks around 1600 and 1700 cm- are due to
amount of caffeine in the powdered coffee beans is the two carbonyl compounds and C=N bond. The
given by: peaks at around 3000 cm- are due to the C-H bonds
of methyl groups since caffeine has three methyl
groups on the cyclic structure (Paradkar & Irudayaraj,
𝑤𝑒𝑖𝑔ℎ𝑡𝑐𝑎𝑓𝑓𝑒𝑖𝑛𝑒 = 𝑤𝑒𝑖𝑔ℎ𝑡𝑐𝑜𝑓𝑓𝑒𝑒 𝑠𝑎𝑚𝑝𝑙𝑒 × 0.014 2014).
= 20.0 𝑔 × 0.014
= 0.280 𝑔 IV. Conclusion
Results showed that there is a significantly high yield
of caffeine obtained and this outcome can be
Using the computed theoretical weight caffeine and attributed, primarily, to the appropriate use of
the measured weight of caffeine extracted in the extraction technique and extracting solvent. Thus, the
experiment, the percent yield is given by: choice of extraction technique and extracting solvent
is crucial for an efficient isolation of caffeine,
considering its relative solubility.
𝑒𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
% 𝑦𝑖𝑒𝑙𝑑 = × 100
𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 V. References
0.263 𝑔
= × 100 Coffee (n.d.) Retrieved 29 March 2017 from
0.280 𝑔 https://monographs.iarc.fr/ENG/Monographs/
vol51/mono51-6A.pdf
= 93.93%
Table 2. Summary of computed data Food and Drugs Administration US (2012).
Percent weight of caffeine 1.315% Annual caffeine report. Retrieved 27 March
Percent yield 93.93% 2017 from
https://www.fda.gov/downloads/aboutfda/cen
tersoffices/officeoffoods/cfsan/cfsanfoiaelectr
onicreadingroom/ucm333191.pdf

3 | Chem35.1 Extraction of Caffeine from Coffee

 George AJ. (2000). Central nervous system
stimulants. Baillere’s Best Pract Res Clin
Endocrinol Metab 14(1):79-88.
Hopes M. (1997). What’s your poison?
LOCATION OF PRODUCER: Australian
Broadcasting Corp. Retrieved 29 March 2017
from
http://www.abc.net.au/quantum/poison/caffei
ne/ caffeine.htm.
Illy, E. & Pizano, D. (2003). Coffee and Health:
New research findings. Proceedings of the
International Seminar on Coffee and Health
40th Anniversary meeting of the ICO
Cartagena, Colombia. Retrieved 29 March
2017 from
http://www.ico.org/event_pdfs/proceedings.p
df
Kamimori GH, Penetar DM, Headley DB, Thorne
DR, Otterstetter R, Belenky G. (2000). Effect
of 3 caffeine doses on plasma
catecholamines and alertness during
prolonged wakefulness. Eur J Clinical
Pharmacol 56(8):537-544
Lundsberg, L.S. (1998). Caffeine consumption.
In: Spiller GA, editor. Caffeine. New York:
CRC Press. p 199-224.
Paradkar, M., & Irudayaraj, J. (2006). A Rapid
FTIR Spectroscopic Method for Estimation of
Caffeine in Soft Drinks and Total
Methylxanthines in Tea and Coffee. Journal of
Food Science, 67(7), 2507 - 2511.
doi:10.1111/j.1365-2621.2002.tb08767.x.
Roy, S. (2015). Solvent extraction. Retrieved 30
March 2017 from
https://www.slideshare.net/DilipSaha1/solvent-
extraction-51718683
Rydberg,J., et al., (2004). Solvent extraction
equilibria. Taylor and Francis Group, LLC.
Villarante, N. & Chiu, H. (2010). Laboratory
manual in organic chemistry II. University of
the Philippines Manila: Manila
Williamson, K. L., & Masters, K. M. (2010).
Macroscale and Microsale Organic
Experiments (6th ed.). Cengage Learning.
4 | Chem35.1 Extraction of Caffeine from Coffee
VI. Guide Questions
1. Discuss the following:
a. Liquid-liquid Extraction
In a liquid-liquid or solvent extraction, ether is
used as the extracting solvent in order to
separate a desired compound from the mixture.
The ideal properties of extraction solvent,
includes readiness to dissolve, high solubility,
low boiling point, immiscibility with the other
phase, and having high solvent power for
hydrocarbons. Extraction can also done by
using instruments such as the separatory
funnel. (Fieser & Williamson, 1992). Using the
solubility differences, the two immiscible
solvents would separate into the aqueous or
organic layer.
b. Solid-liquid Extraction
Solid-liquid extraction is done using a Soxhlet
apparatus which allows transfer of solutes in a
solid to a continuous liquid. This method
involves repeated extraction with hot water that
leads to the complete extraction of the crude
product from the organic solid placed in the
porous thimble (Mann & Saunders, 1974).
Caffeine, having lower molar weight, can be
isolated from coffee composed of other
compounds. Applications include brewing of tea
and coffee.
c. Acid-base Extraction
Acid-base extraction employs simple acid or
base reactions to separate organic substances
in a solution, whether they are strong acid, weak
acid, neutral, or basic. A weak base (sodium
bicarbonate) will react only to a strong acid
(benzoic acid) and forms an ionic salt (sodium
benzoate) which can be removed since it is
dissolved in the aqueous layer. On the other
hand, a strong base (hydroxide) will only react
with a weak acid (phenol) that can also be
dissolved and removed from the solution as an
ionic compound (sodium phenoxide). Thus,
what remains is the neutral compound. The
isolated compounds can be regenerated by
adding an acid or base to regenerate the
covalent compounds (Fieser & Williamson,
1992).
2. Why is it necessary to remove the stopper from a 𝑅
separatory funnel when liquid is being drained = 200𝑚𝐿 =3
from it through the stopcock? 12𝑔 − 𝑅
The extracting solvent, ether for instance, is 400𝑚𝐿
very volatile. In carrying acid-base reactions,
R = 7.2 g of compound A
liberation of gas occurs due to carbon dioxide
formation. The stopper must be removed from
6. Aniline, an amine, is soluble in diethyl ether but not
the separatory funnel because of the pressure
in water; however, aniline is extracted from diethyl
build-up. If the stopper is not remove when
ether with aqueous hydrochloric acid. Explain.
draining the contents, vacuum will build up,
Aniline is a weak base that when it reacts with
reducing the rate of draining, eventually
aqueous hydrochloric acid yielding anilinium
stopping removal, and then air will come in
chloride, an ionic compound. This dissolves in
through the stem, causing the layers to mix
the aqueous layer and thus can be separated
again. If the stopper is removed, there is equal
(Fieser & Williamson, 1992). This is an
pressure inside and outside the apparatus and
example of an acid-base extraction.
draining would be easier.
7. The equilibrium for phenol, sodium phenoxide,
3. What is the purpose of adding magnesium oxide
sodium bicarbonate, and carbonic acid is shown
in the extraction of caffeine?
below:
The water dissolved in organic solvent is an
impurity. Through evaporation, water can be
𝑃ℎ𝑒𝑛𝑜𝑙 + 𝑁𝑎𝐻𝐶𝑂3 ↔ 𝑠𝑜𝑑𝑖𝑢𝑚 𝑝ℎ𝑒𝑛𝑜𝑥𝑖𝑑𝑒 + 𝐻2 𝐶𝑂3
removed and leaving the desired compound. To
achieve more efficient removal of water, a
Determine the Keq for this reaction
drying agent or an adsorbant is used.
Magnesium oxide is added since
[phenoxide][𝐻 + ]
dichloromethane is also soluble to water. It acts 𝐾𝑎 = = 1.30x10−10
as an anhydrous chemical agent to dehydrate [phenol]
the solution. When added, all moisture in the
solution is absorbed and the caffeine is ([HCO3− ]+[𝐶𝑂3−2 ])[𝑁𝑎+ ]
𝐾𝑏 =
adsorbed while the extracting solvent (ethanol) [𝑁𝑎𝐻𝐶𝑂3 ]
evaporates. This leads to a purer sample due to = 2.33x10−8
less risks of impurities.
[sodium phenoxide][ H2CO3]
𝐾𝑎 = = 𝐾𝑎 × 𝐾𝑏
4. What are alkaloids? What makes the isolation of [phenol][ NaHCO3]
alkaloids easy versus other natural products?
= 𝟑. 𝟎𝟑𝐱𝟏𝟎−𝟏𝟖
Alkaloids are nitrogen-containing bases and are
naturally occurring amines. In acid-base
titrations, isolation of desired compound is done I hereby certify that I have given substantial contribution to
this report.
by forming soluble salts to the aqueous layer,
then removing them from the organic layer.
Alkaloids are easier to separate since they form _________________________
salts when acid is added. Garcia, Beatrice Emmanuelle

5. Assume that the partition coefficient, K, for

partitioning of compound A between diethyl ether _________________________
and water is 3. Given 400 mL of aqueous solution Santos, Shaine Dominique
containing 12 grams of compound A, how many
grams of A could be removed from the solution by
a single extraction with 200 mL of diethyl ether? ________________________

𝑔 Solomon, Marc Ralph

𝑆𝑜𝑙𝑢𝑏𝑖𝑙𝑖𝑡𝑦 𝑖𝑛 𝑜𝑟𝑔𝑎𝑛𝑖𝑐 𝑙𝑎𝑦𝑒𝑟 (𝑚𝐿)
𝐾= 𝑔 =3
𝑆𝑜𝑙𝑢𝑏𝑖𝑙𝑖𝑡𝑦 𝑖𝑛 𝑎𝑞𝑢𝑒𝑜𝑢𝑠 𝑙𝑎𝑦𝑒𝑟 (𝑚𝐿)

5 | Chem35.1 Extraction of Caffeine from Coffee