Extraction and Isolation of Caffeine from Ground Coffee Beans

Curias, L.Q., Hufalar, K.L., & Magtaas, R.H.

Submitted on March 31, 2017
Abstract
Caffeine is the most widely used legal drug in the world. It is found naturally in tea leaves and coffee beans.
For this experiment, caffeine is extracted from coffee in order to determine its properties and to calculate the
percent yield. Extraction of caffeine comes in three processes. First is the solid-liquid extraction. It is the
dissolution of a solid substance from a solid carrier in a liquid solvent. In this case, the grounded coffee is
the solid carrier and the ethanol is the liquid solvent. Second is the liquid-liquid extraction. It is used to
remove the brown color of the caffeine, and is defined as the transfer of a soluble solid from one of the two
immiscible solvents. The solvents added are water and chloroform, which is the extracting and organic
solvent. Finally, the third is the acid-base extraction. This is used to fully separate the caffeine from the
sample, and the addition of a base, in this case, sodium hydroxide, reacts with the tannins, which are quite
acidic. The amount of caffeine extracted is 0.025 grams and a percent yield of 10.16%. The final product is
then subjected to infrared radiation spectra, and it is found out that final product still had impurities due to
the presence of OH bonds at the 3000 cm - region. It is recommended to follow the procedures properly to
avoid further experimental errors, which in turn, can increase the percent yield.

Keywords: Caffeine, Solid-Liquid Extraction, Liquid-Liquid Extraction, Acid-Base Extraction, Soxhlet

apparatus

I. Introduction

Caffeine is a naturally occurring xanthine

derivative. It is a methylxanthine alkaloid and is
structurally related to adenosine. Alkaloids are
basic nitrogenous plant products, and are
possessing heterocyclic nitrogen as their structural
unit (Dewick, 2009). Caffeine acts primarily as an
adenosine receptor antagonist with psychotropic
and anti-inflammatory activities (National Cancer
Institute, n.d.). It is a central nervous system
stimulant, and has been very useful in restoring
mental alertness. Figure 2. Caffeine in pow dered form. Retrieved from
https://yahoo.com

Friedlieb Ferdinand Runge performed the first

Figure 1. Chemical structures of caffeine and adenosine.
Retrieved from https://upload.wikimedia.org
This xanthine derivative, when isolated, is a white
crystalline solid with a melting point of 235C -
238C. It is soluble in water at 25C, pyrrole,
pyridine, and tetrahydrofuran. It has a chemical
name of 1,3,7-trimethylxanthine and a chemical
formula of C H N O .
8 10 4 2
Caffeine is described as both a food and drug
isolation of pure caffeine from coffee beans in 1820
(Weinberg & Bealer, 2001). Obtaining pure
caffeine from coffee is not easy since coffee
contains other compounds that are soluble in
chloroform (Williamson, 2011). These compounds
are the diterpenes, cafestol, and kahweol. Both are
naturally present in the oil contained in coffee.
Diterpenes are also soluble in ethanol and diethyl
ether. Antioxidants are also found in coffee. Thes e
include chlorogenic acids and melanoidins. Tannic
acid, also known as gallotanic acid, is an astringent
product plant product also present in coffee
(Kalmus, 2015). This gives the coffee its dark color.
The common solvents used in isolation of caffeine
are benzene, chloroform, trichloroethylene, and
dichloromethane. In the experiment, chloroform
(CHCl ) is used.
3

additive, and is used to treat tiredness, drowsines s

(Nichols, 2016). It is also used to improve the The objectives of this experiment are to extract
effects of some pain relievers. It occurs naturally in caffeine from coffee beans, and to determine its
tea leaves, coffee beans, kola nuts, guarana, and properties and the yield of extraction.
yerba mate.

Chem 35.1: Extraction and Isolation of Caffeine from Ground Coffee Beans
Page 1 of 5
II. Experimental
Twenty grams of finely powdered Liberica beans
were obtained and subjected to reflux extraction
using a Soxhlet extractor, with 95% EtOH as the
solvent, for two hours. After the extraction, an
alcoholic extract was acquired and cooled to room
temperature. Ten grams of MgO in 70-mL H2O was
added to the cooled extract. The solution was
heated until the solvent completely evaporat ed.
30-mL H2O was added to obtained dry residue.
The resulting solution was boiled afterwards. Hot
solution was subjected to vacuum filtration three
times with additional 10-mL H2O per repetition.
Few drops of dilute H2SO4 were added to the
combined water extracts. Resulting solution was
heated until two-thirds of the solution evaporat ed.
Remaining hot solution was then filtered and
cooled to room temperature. The filtrate underwent
liquid-liquid extraction in a separatory funnel with
10-mL chloroform as solvent. The aforementioned
procedure was done three times. The organic
layers were collected thereafter. Two milliliters of
NaOH and 2-mL H2O were added to remove the
color of the obtained solution. The solution was
heated until solvent evaporated and then dried.
Percent yield and IR spectra of the product were
determined and obtained.
III. Results
Table 1. Summary of data obtained.
Weight of powdered coffee beans
20.000
(g)
Weight of caffeine crystals (g) 0.025
According to Daud, Ling, and Hassan (2001), the
caffeine concentration of Liberica beans is 1.23 %
by weight. Using this value, the amount of caffeine
in the sample used is given by,
increase its surface area which in turn increased
= (20.000 ) (0.0123 ) solvent, ethanol, was appropriate for the procedure
= 0.246
Using the theoretical weight of caffeine and the
obtained weight in the experiment, the percent
yield of caffeine is given by,
0.025
% = 100%
0.246
= 10.16%
Chem 35.1: Extraction and Isolation of Caffeine from Ground Coffee Beans
On the other hand, the crude caffeine extract was
subjected to an Infrared Spectrometer. The
spectra obtained was also compared to the spectra
of pure caffeine.
Figure 3. IR spectra of crude caffeine extract (green) and pure
caffeine (black).
IV. Discussion
Extraction of caffeine coming from naturally -
occurring coffee beans through a simple distillation
or recrystallization process is quite difficult to
achieve because of the number of distinct organic
compounds found in these beans such as tannins
and lipids along with caffeine which could
contribute to a positive error to the amount of
caffeine in a given mass of grounded coffee beans.
In the proposed methodology, caffeine was
extracted properly through a three-step extraction
procedure which includes: liquid-liquid, solid-liquid,
and acid-base extraction.
Solid-liquid extraction is defined as the dissolution
of a solid substance from a solid carrier in a liquid
solvent. In the study, the extraction was achieved
using the Soxhlet apparatus, as shown in Figure 4,
wherein the grounded coffee acted as the carrier
solid and ethanol as the solvent. The solid sample
was contained in a porous filter paper thimble. This
sample was prepared in a powdered form to
the rate of dissolution in the solvent. The chosen
with it being organic and having a relatively low
boiling point which made the first extraction faster.
This solvent was heated up in the boiling flask until
vapors formed which were condensed in the
condenser tube. The condensed liquid then fell into
the sample container and passed through the
paper thimble with the dissolved impure caffeine.
When the glass tube inside was filled up, it was
automatically siphoned down into the boiling flask
which made the process perpetual. This method is
very efficient since the solvent was recycled
throughout the procedure; the process was done
independently of manual interaction; and the solid
sample was ensured to be dissolved in the solvent
given its low solubility.
Page 2 of 5

Figure 4. Soxhlet apparatus setup. Retrieved from
https://chem.libretexts.org
After the first extraction, the resulting product still
had a color of brown which does not characterize
pure caffeine which was white and therefore,
another extraction process was made. This
extraction process is the liquid-liquid extraction
method which is defined as the transfer of a soluble
solid from one of the two immiscible solvents. It
was required that the solid sample should be more
soluble in the destination solvent for it to be
properly separated. In this case, the two solvent s
used were water, the aqueous layer with the
dissolved impure caffeine, and chloroform, the
extracting solvent and organic layer. The
extracting solvent used was appropriate since it
just dissolved the solute and did not react with it or
with the other solvent; it was immiscible, and it was
highly volatile (-24.2 oC) which made it easier to
separate with the sample. This process was done
using a separatory funnel as shown in Figure. 5.
The aqueous sample was mixed with the solvent
and shaken to transfer the solute into the
extracting solvent. The purer caffeine was easily
transferred to the solvent since it had a relatively
high partition coefficient which is denoted by the
following equation,
Chem 35.1: Extraction and Isolation of Caffeine from Ground Coffee Beans
Figure 5. Separatory funnel setup. Retrieved from
http://chemistry.oregonstate.edu
wherein solvent 2 is the organic solvent and 1 is
the aqueous solvent. It can also be denoted as the
ratio of solubility of the sample in the organic
solution to the aqueous solution. With chloroform
having a higher density than water, the organic
layer settled at the bottom of the funnel. When the
organic layer was drained from the funnel, it was
necessary to remove the stopper to prevent
negative pressure in the container which can deter
the draining process. If the stopper wasnt remove,
there could be a risk of mixing the two layers which
can be induced by air going inside from the bottom
drain to balance the pressure inside. The resulting
product was still impure since it had a pale yellow
color.
To fully separate caffeine from the impure sample,
the acid-base extraction method was used. The
addition of sodium hydroxide was done to remove
tannins from the sample which are acidic. The
base did not react with the caffeine since it is an
alkaloid. Alkaloids are naturally-occurring amines
which are basic. The caffeine was easily separated
from the tannins since the salt formed by adding an
acid was soluble in the aqueous layer. This layer
was then evaporated and the remaining product
was subjected to recrystallization. The crystalline
solid was then subjected to infrared
spectrophotometry. The plot showed minor peaks
in the fingerprint region which represented the
stretching of C-C, C=C, and C-N bonds. A distinct
peak was also observed in 1600-1700 cm- region
which proved the presence of carbonyl groups.
The peaks around 3000 cm - signified the presenc e
of C-H bonds of the methyl groups in caffeine. The
final product, which passed three extractions
processes, still had some impurities. This can be
seen in the region further from the 3000 cm - point
which signified the presence of OH bonds.
Page 3 of 5
V. Conclusion
Extraction and isolation of caffeine from ground
coffee beans was made possible through different
methods of extraction. Solid-liquid extraction was
used to dissolve desired compounds from the initial
solid sample. Addition of MgO is necessary to
further minimize the impurities. Acid-base
extraction, through the use of NaOH, was
performed to confirm that the acidic compounds
present, like tannins, remain water soluble and that
the caffeine will be present as the base. Moreover,
liquid-liquid extraction was utilized to separate the
organic phase, which contains the caffeine, from
the aqueous phase through the use of chloroform
as solvent.
Results of the experiment show that the isolation
of caffeine in the Liberica coffee sample was
successful, although it still has some impurities as
shown in the IR spectra.
It is recommended to increase the number of reflux
extractions to produce a purer solution.
VI. Guide Questions
Assume that the partition coefficient, K, for
partitioning of compound A between diethyl
ether and water is 3. Given 400 mL of aqueous
solution 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?
n.a. (n.d. ). Compounds in Coffee. Retrieved from
=
http://coffeeandhealth.org/all -about -
200
3 = 12
400
= 7.2 n.a. (n.d.). CAFFEINE. Retrieved from
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, which is weak base, becomes an ionic
compound anilinium chloride when reacted with
aqueous hydrochloric acid. The reaction is as
follows:
Chem 35.1: Extraction and Isolation of Caffeine from Ground Coffee Beans
This ionic compound dissolves in the aqueous
layer, thus, it can be separated using diethyl ether.
The equilibrium for phenol, sodium phenoxide,
sodium bicarbonate, and carbonic acid is
shown below:
+ 3 + 2 3
Determine the Keq for this reaction
[ ] [ + ]
= = 1.30x10 10
[ ]
([3 ] + [3 2 ])[+ ]
= = 2.33x10 8
[3 ]
[] [ 2 3 ]
= =
[ ] [ 3 ]
= 3.03x10 18
VII. References
n.a. (n. d.). Caffeine. Retrieved from
https://www.ncbi.nlm.nih.gov/mesh/68002
110.
n.a. (n. d.). Caffeine (Code C328). Retrieved from
https://ncit.nci.nih.gov/ncitbrowser/Conce
ptReport.jsp?dictionary=NCI_Thesaurus&
ns=NCI_Thesaurus&code= C328.
coffee/compounds-in-coffee/.
n.a. (n.d.). CAFFEINE. Retrieved from
http://www.ilo.org.dyn/icsc/showcard.displ
ay?p_card_iD=0405.
https://toxnet.nlm.nih.gov/cgi-
bin/sis/search2/r?dbs+hsdb:@term+@rn+
@rel+58-08-2.
n.a. (n.d.). Showing metabocard for Caffeine.
Retrieved from
http://www.hmdb.ca/metabolites/HMDB01
847.
n.a. (n.d.). What is an Alk aloid? Classification of
alk aloids. Retrieved from
http://www.plantscience4u.com/2013/02/
what-is-alkaloid.html#.WN0qmW-GO00.
Dewick, P. (2009). Medicinal Natural Products
(3rd ed). pp 187
Page 4 of 5
Harbolic, B. (n.d.). Caffeine. Retrieved from I hereby certify that I have given substantial
http://www.medicinenet.com/caffeine/artic contribution to this report:
le.htm#what_is_caffeine.

Kalmus, S. (2015). Tannins and Acids in Coffee. CURIAS, Lee Amherstia Q.

Retrieved from
http://www.livestrong.com/article/455484-
HUFALAR, Karl Joseph L.
tannins-and-acids-in-coffee/

Ling, L.S., Daud, N.N., & Hassan, O. (2001).

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Nichols, H. (2016). Caffeine: All You Need to

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Chem 35.1: Extraction and Isolation of Caffeine from Ground Coffee Beans
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