ISOLATION OF CAFFEINE FROM SODA DRINK

An Experiment on Extraction of Caffeine from a Soda Drink using Liquid-liquid Extraction

Written By

Krista Leigh Belocura

University of San Carlos

Talamban Campus

December 2019
Introduction

The most widely consumed stimulant in the world is caffeine. It is also the most highly studied ergogenic
aids (Andrews, n.d.). It acts as adenosine receptor blockers and phosphodiesterase inhibitors. Best known
for its ability to decrease fatigue and increase mental alertness as a result of stimulating the brain,
“wakefulness” is associated with this stimulant. Despite its benefits, it also has its adverse effects like
counteracting the anti-anxiety effects of medications and increasing the bad effects of stimulant drugs like
amphetamines and methylphenidate (Connolly, 2019). It can cause acute intoxication when ingested at
amounts 1-5 g, with plasma concentrations higher than 80 mg/mL.

Caffeine is slightly soluble in most polar solvents but is highly soluble in less polar solvents (Pradeep,
Rameshaiah & Ashoka, 2019). Its melting point is 234°C-239°C and its chemical formula is C8H10N4O2. It is
an intensely bitter, white powder in its pure state. Caffeine is an alkaloid of the methylxanthine family, which
also includes the similar compounds theophylline and theobromine. The structure of caffeine is

Figure 1. Structural Formula of Caffeine

Caffeine can be extracted from different sources, such as plants, tea leaves, tea bags, soda, and coffee
beans among many others. Also, it can be produced synthetically (Heffron, 2013). There are various
methods in extracting caffeine and each method uses different solvents and techniques. In this experiment,
liquid-liquid extraction (LLE) was applied. Basically, this method separates compounds or metal complexes
based on their relative solubilities in two different immiscible liquids. The experiment focused on caffeine
extraction in a soda drink, specifically Coke, using water (polar) and dichloromethane (slightly polar).

LLE is composed of steps of mixing followed by a step of phase separation. Equilibrium is reached when
the chemical potential of the extractable solution is the same in the two phases. This mechanism follows
the definition of the distribution coefficient, Kd. This dimensionless property describes how a chemical
substance distributes itself between two phases (Johanson, 2010). In solvent extraction, it is a measure of
how well-extracted a species is.

𝐶1
𝐾=
𝐶2

Equation 1. Distribution Coefficient Formula, Kd

where C1 and C2 are the equilibrium concentration of the solute in the two phases respectively. In this
experiment, C1 is DCM and C2 is H2O. The objectives of this experiment are to (1) isolate caffeine from a
commercial soft drink using solvent extraction, (2) determine the melting point of caffeine, (3) explain the
purposes of the steps and to (4) cite ways to improve the yield of the isolation procedure.
Methodology

Two hundred milliliters (mL) of soda drink was measured using a beaker. Afterwards, twenty mL of
concentrated ammonia were added to the mixture.

One hundred mL of the caffeine solution was transferred into a 250-mL separatory funnel, then mixed with
twenty mL of dichloromethane (DCM). Because the addition created tension and pressure inside the funnel,
the funnel’s cover was held tightly. The funnel was inverted, while still holding the cover, then immediately
vented by opening the stopcock. Consequently, this step was repeated five times. It was noted that
vigorous shaking should be avoided.

Once there was no more fizzing, the DCM layer was drained through a funnel that was plugged with cotton
and a layer of anhydrous sodium sulfate. Then, these steps were repeated twice and the filtrates from the
first batch and the second batch were pooled together in the same beaker.

The beaker containing the pooled filtrate was then submerged in a hot water bath, allowing the solvent to
boil off until only 5 mL of the mixture remained in the beaker. Subsequently, ten drops of petroleum ether
were added to the concentrate and the surface of the beaker was scratched using a clean dry steering rod
to induce crystallization. Then the beaker was placed in an ice bath to let the solvent evaporate to dryness.
Finally, the extract’s melting point was determined.

The dried caffeine powder scratched from the surface of the beaker was placed inside a capillary tube until
the sample packed into the bottom of the tube. This capillary tube was placed into the melting point setup
and the Bunsen burner was turned on. The sample was carefully observed and the temperature when the
sample started to melt was noted.

Presentation of Results
Table 1. Observations from the Experiment
Mixture Reaction
Soda drink + Concentrated Ammonia No layer formed, no fizzing
Dichloromethane + Soda drink + Concentrated Ammonia Fizzed violently, created two layers
Filtrate + Petroleum ether Smoked

Figure 2. After heating the sample at around its melting point, the sample was burnt before melting

Sample’s Melting Point: 224°C-232°C

Discussion of Results

Concentrated ammonia is a weak alkaline liquid and gives a solution a high pH. The H + and Cl- that were
attached to the caffeine hydrochloride reacted with the concentrated ammonia to form ammonium chloride
and the caffeine hydrochloride was converted to the free base form of caffeine, which is much less polar
than caffeine hydrochloride and much less soluble in water, causing it to precipitate out. The sucrose that
originally dissolved in the water remained in solution. Then, the nonpolar caffeine free base dissolved
readily in DCM, but the somewhat polar sucrose stayed in the water. This step produced fizzing and small
droplets in the solution, which significantly increased the area of contact between the two phases and sped
the equilibration of the desired compound between them.

The addition created tension and pressure inside the funnel, so the funnel’s cover was held tightly. The
funnel was inverted, while still holding the cover, and then immediately vented by opening the stopcock.
This step was crucial because it eased the tension in the mixture caused by pressure buildup of carbon
dioxide. Vigorous shaking was avoided because it may have caused formation of emulsion, a mixture of
immiscible solvents which refuses to separate into two distinct phases, thus making the extraction of
caffeine hard to complete. Because caffeine with dichloromethane and sucrose with water do not form
homogeneous mixture, due to their polarity and density, two layers were formed in the separatory funnel.

Once there was no more fizzing, the DCM layer was drained (bottom layer of the flask) through a funnel
that was plugged with cotton and a layer of anhydrous sodium sulfate. This step annihilated the emulsion
formed in the methylene chloride layer. Subsequently, all the previous steps were repeated twice and the
filtrates from the first batch and the second batch were pooled together in the same beaker.

The beaker containing the pooled filtrate was then submerged in a hot water bath, dissolving the crude
caffeine, leaving out only the pure caffeine. This is important because pure caffeine has a lower boiling
point than the rest of the impurities making it crude.

Moreover, the addition of petroleum ether made the caffeine precipitate. Caffeine is less soluble in this
mixed solvent, so it produced the crystals of the extracted caffeine. After the crystals emerged, the beaker’s
sides were scratched. This technique encourages nucleation of a seed crystal, thus increasing the size of
the extracted caffeine crystals (Nichols, 2019).

One mistake in this experiment was the failure to measure the yield (extract), which would have been
useful to determine percent yield, percent recovery and percent error. These might have been crucial in
deciding whether soda drinks have high concentrations of caffeine and whether the method used was
effective. Furthermore, there was a considerable number of transfers throughout the experiment which
presented numerous opportunities of product loss. Thus, it is suggested that the steps must be read
carefully and executed with care and presence of mind. Another recommendation is to use sublimation
procedure which allows caffeine to have the ability to pass directly from solid to vapor and reverse to form a
solid, without undergoing the liquid phase.
After the extraction process, the melting point of the extracted caffeine was determined through a heating
bath setup. DCM was evaporated first because it has a boiling point in the range 30°C – 40°C while
caffeine’s boiling point is 173°C. It was observed that the sample started to melt at 224°C and when it
reached 232°C, all the samples were completely melted. Its high melting point indicates that caffeine has
greater intermolecular forces and less vapor pressure. This is vital for its storage and transport. If it had a
low melting point, it may cause leaks or decomposition of the product even before it arrives at the market.

Conclusion

These findings are proof that caffeine is present in soda drinks. This implies that those who are under
medication for depression or those who are advised by their doctors to avoid taking in caffeine should also
avoid drinking soda.

Moreover, it can be concluded from the experiment that multiple extraction performs better than a single
extraction because there is more surface area contact with lesser volumes, thus mixing the solution faster
and more thoroughly than with larger volumes of liquid.

Although the procedure seems easy to understand, the process is tedious and needs careful attention in
order to maximize extract yield. If it were in the industry, each step must be well-planned so that product
loss would be minimal.

Lastly, caffeine has a high melting point, which means that it has a high boiling point and great
intermolecular forces. These characteristic properties of caffeine serve useful in the industry for both its
production and transport. Also, it gives doctors information about its effect towards their patients and how
long it stays in the body system before it is completely washed out.

References

Andrews, R. All About Caffeine. Retrieved 27 November 2019, from

https://www.precisionnutrition.com/all-about-caffeine

Connolly, M. (2019). Anxiety and Caffeine. Retrieved 28 November 2019, from

https://www.psycom.net/anxiety-and-caffeine

Johanson, G. (2010). Comprehensive Toxicology. Retrieved 28 November 2019, from

https://www.sciencedirect.com/referencework/9780080468846/comprehensive-toxicology

Nichols, L. (2019). 3.5E: Initiating Crystallization. Retrieved 30 November 2019, from

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_Lab_Technique
s_(Nichols)/3%3A_Crystallization/3.5%3A_Procedural_Generalities/3.5E%3A_Initiating_Crystallization

Pradeep, S., Rameshaiah, G., & Ashoka, H. (2019). Caffeine Extraction and Characterization. Section:
General Science Sci. Journal Impact Factor 4.016, 7(9), 16. Retrieved from
https://www.researchgate.net/publication/326293350