GROUP PROJECT REPORT

EXTRACTION OF CAFFEINE FROM COFFEE AND TEST FOR PRESENCE OF

CARBONYL GROUP IN CAFFEINE

Muhammad Khalish Reeza bin Dzulkhalif, Nurul Izmaniza binti Roslan, Nurhaziqah
binti Hasbi, Presziny Latak Liwan, Muhammad Najmi Fitri bin Norizam, Muhammad
Nazmi bin Jefry, Raidah Najiah binti Sugino, Saerina Nurbayah Iskandar, Sharifah
Nur Aina Najwa binti Wan Muhamad Sariff

Centre for Pre-University Studies, Universiti Malaysia Sarawak

a2200776@siswa.unimas.my

Abstract
Caffeine is the most popular psychoactive substance in use today. The objective of this
experiment is to extract caffeine from coffee and to test the presence of ketone in the
caffeine molecular structure. The coffee sample is boiled with distilled water and its
residue is filtered using filter paper. The result shows that when mixed with Brady’s
reagent, the mixture turns into an orange precipitate. The caffeine extracted from the
Robusta Coffee is more than the caffeine extracted from the Arabica Coffee.

Keywords: Caffeine; Aldehyde; Ketone; Brady’s Reagent; Lucas’ Reagent; Tollens’

Reagent

Introduction
Coffee is one of the most popular beverages globally other than water and tea. The
stimulant caffeine is also the most popular psychoactive substance in use today. Although
many of us require our morning brew to operate, other people choose to abstain from
caffeine because of its impact on sleep, restlessness, or pregnancy. Fortunately, scientists
have devised several methods for us to enjoy coffee without caffeine (‘How is decaffeinated
coffee made?...’, 2018). Below, we examine the various approaches!

The type of bean used to make coffee affects its caffeine concentration. According to an
article titled '10 Differences Between Robusta and Arabica Coffee' published in 2014, the
caffeine content in Robusta beans is about 2.7%, which is nearly twice the amount found
in Arabica beans at 1.5%. In general, only most of the caffeine in coffee is removed during
decaffeination. In the EU, decaffeinated coffee may contain up to 0.1% caffeine while
decaffeination in the United States must eliminate 97% of the original caffeine content
(‘How is decaffeinated coffee made?...’, 2018).

The active ingredient that makes coffee valuable for humans is caffeine. People have been
using plants containing caffeine for medicinal and recreational purposes since ancient
times. But the chemical compound itself wasn't identified until 1819, when Friedlieb
Ferdinand Runge, a young physician, isolated and purified the white crystalline

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substance. According to the Better Health Channel, caffeine is a drug that activates and
heightens the activity of the nervous system and brain.

Caffeine is a member of the purine family of heterocyclic compounds and its IUPAC name
is 1, 3, 7-Trimethylpurine-2,6-dione. Its chemical formula is C8H10N4O2, and it can be
classified as an alkaloid, which is a type of substance that is produced as the end product
of nitrogen metabolism in certain plants. According to the article 'Caffeine' published in
2023, caffeine has a molar mass of 194.19 grams (6.85 ounces) and appears as white
crystals when pure. It is soluble in both water and many organic solvents. Caffeine can
be obtained either by extraction from natural sources or by synthesizing it from uric acid.

Figure 1: The chemical structure of caffeine (Caffeine Chemical Formula - Chemical Formula,
Structure And Physical Properties, n.d.)

Byju's article in 2023 explains that caffeine is classified as an alkaloid and is created by
the fusion of pyrimidinedione and imidazole rings. The pyrimidinedione ring consists of
two nitrogen atoms and has six members, while the imidazole ring contains two nitrogen
atoms and has five members.

Objective
1. Conduct an experiment to extract caffeine from coffee grounds.
2. To observe while extracting caffeine from coffee grounds solution.
3. To compare amount caffeine observed while extracting caffeine from coffee grounds
solution.
4. To prove the presence of carbonyl group in caffeine extracted.

Materials and methods

Materials:
18g of ground coffee (Arabica and Robusta coffee bean), 4g calcium carbonate, 40 mL
petroleum ether, distilled water, filter paper, saturated salt solution, 95% ethanol,
Brady’s reagent( 2,4-Dinitrophenylhydrazine) solution, Tollen’s Reagent, Lucas Reagent

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Methods:

Brady’s Reagent:

Tollens’ Reagent:

Lucas’ Reagent:

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Results and discussion

Coffee sample Caffeine amount

Arabica Less

Robusta More

Table 1: Results from the caffeine extraction experiment

Sample Observations

Caffeine + Brady’s Reagent Orange precipitate is produced

Caffeine + Tollen’s Reagent No changes

Caffeine + Lucas’ Reagent Solution is colourless

Table 2: Results from Brady’s , Tollen’s and Lucas’ Test

Discussion
In the first experiment, we use coffee bags instead of coffee grounds to extract caffeine
from because it would boost the filtration process for our extraction. The caffeine bags
would be put into a beaker and 60 mL of distilled water was poured into the same beaker.
Then, the solution was boiled for 15 minutes, during which the mixture was shaken to
prevent foaming. This can ensure accurate extraction results. Then, the mixture was
filtered using filter paper into another clean beaker to filter coffee grounds from the
desired solution. Then 250 mL of boiling distilled water was poured into the beaker. This
is to dissolve caffeine as much as possible. Letting the solution cool down too early may
result in a small amount of caffeine at the end of the experiment. The solution was then
put into a separatory funnel. The separatory funnel was then added with 15 mL of
petroleum ether and then shaken gently to mix the solution with the petroleum ether.
Caffeine is an organic compound and to separate caffeine from coffee solution, an organic
solution must be used. Organic compound is also known as a nonpolar compound. Organic
or nonpolar solution was used in this experiment to separate caffeine because like
dissolves like. Non polar substances dissolve in nonpolar solvent while polar substances
dissolve in polar solvent. Petroleum ether used in this experiment is an organic solution
that separates caffeine from coffee solution. This will result in two layers separating the
organic layer and aqueous layer. Then the separatory funnel was put to stand to separate
the layers. The upper layer (organic layer) is the petroleum ether containing caffeine.
Then the bottom layer was filtered out and the upper layer was put into another clean

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separatory funnel to filter more. A salt solution was then put into the solution as it was
hazy. A drying agent(we used calcium chloride) was put into the beaker to dry out the
water molecules remaining in the solution. Then, the solution was put into a clean beaker.
The solution was boiled to remove the petroleum ether until the caffeine crystals remain.
The beaker was put into the fume chamber to dry out any liquid left of the extraction.

From the first experiment, We have not obtained caffeine. This might be caused by
analytical error from ourselves, as we cannot pinpoint which solution is the caffeine
extract during the experiment. Other than that, there are also experimental errors, this
might be caused by the change in our materials for the extraction of caffeine, as we are
supposed to use the organic solvent dichloromethane, but due to the unavailability of the
said solvent, we turned to use petroleum ether. Dichloromethane should be used in this
experiment because caffeine has higher solubility in dichloromethane compared to other
solvents.

In the second experiment, we used the solution we obtained in the first experiment that
we assumed is caffeine extract. We mixed the solution with Brady’s reagent for the
Brady’s test, producing orange precipitate at the end. This shows the presence either
aldehyde or ketones in caffeine. Second test is the Tollens’ reagent test. Tollens’ reagent
is also called as ammoniacal silver nitrate solution. When an aldehyde is warmed with
Tollens’ reagent, a greyish black precipitate or silver mirror is formed. For the Tollens’
reagent test, the result is negative(no silver mirror solution). This is because the carbonyl
group in caffeine is a ketone. This proves again the integrity of the molecular structure of
the caffeine. For the Lucas’ reagent test, the result is a clear solution. This is because
there is no presence of secondary and tertiary alcohol in the caffeine which proves again
the integrity of the caffeine molecular structure.

Conclusion
An experiment has been conducted to extract caffeine from our chosen coffee beans,
Arabica and Robusta coffee beans. While extracting, we observed that there are separate
layers separating caffeine and coffee solution. There is a lot of amount of caffeine observed
in Robusta coffee solution than in Arabica coffee solution. To prove the presence of
carbonyl group in caffeine extracted, Brady’s test, Tollen’s test and Lucas’ test has been
conducted.

References
Journal Articles
Dagan, Y. and Doljansky, J.T. (2006) ‘Cognitive Performance during Sustained
Wakefulness: A Low Dose of Caffeine Is Equally Effective as Modafinil in Alleviating the
Nocturnal Decline’, Chronobiology International, 23(5), pp. 973–983. Available at:
https://doi.org/10.1080/07420520600920734.

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Pan, H.-Z. and Chen, H.-H. (2007) ‘Hyperalgesia, low-anxiety, and impairment of
avoidance learning in neonatal caffeine-treated rats’, Psychopharmacology, 191(1), pp.
119–125. Available at: https://doi.org/10.1007/s00213-006-0613-y.

Smith, A. (2002) ‘Effects of caffeine on human behavior’, Food and Chemical Toxicology,
40(9), pp. 1243–1255. Available at: https://doi.org/10.1016/S0278-6915(02)00096-0.

Giesbrecht, T. et al. (2010) ‘The combination of L-theanine and caffeine improves cognitive
performance and increases subjective alertness’, Nutritional Neuroscience, 13(6), pp. 283–
290. Available at: https://doi.org/10.1179/147683010X12611460764840.

Website Articles

10 Differences Between Robusta & Arabica Coffee (2014). Available at:

https://theroasterspack.com/blogs/news/15409365-10-differences-between-robusta-arabic
a-coffee#:~:text=One%20reason%20that%20the%20taste,double%20the%201.5%25%20of
%20Arabica. [Accessed: 25 Feb. 2023]
Better Health Channel (n. d.) Caffeine. Available at:
https://www.betterhealth.vic.gov.au/health/healthyliving/caffeine#:~:text=Caffeine%20is
%20a%20stimulant%2C%20which,you%20feel%20refreshed%20and%20focused.
[Accessed: 4 Mar. 2023]

Byju’s (2011) Caffeine Chemical Formula. Available at: https://byjus.com/caffeine-

chemical-formula/#:~:text=Caffeine%2C%20also%20known%2
0by%20the,such%20as%20coffee%20and%20tea [Accessed: 23 Feb. 2023]
Chemistry Explained (2023) Caffeine. Available at:
http://www.chemistryexplained.com/Bo-Ce/Caffeine.html [Accessed at: 23 Feb.2023]
Compound Interest (2018). How is decaffeinated coffee made? The chemistry of coffee
decaffeination. Available at: https://www.compoundchem.com/2018/09/26/coffee-
decaffeination/. [Accessed: 26 Feb. 2023]
Tilling, S. (2001) The Discovery and Isolation of Caffeine. Available at:
http://www.chm.bris.ac.uk/webprojects2001/tilling/isolation.htm [Accessed: 23 Feb.2023]

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