MAPUA UNIVERSITY

School of Chemical, Biological, and Materials Engineering and Sciences

Experiment No. 1.4

Liquid-Liquid Extraction: Extract Caffeine from your Everyday Drinks

Submitted By:

Date Performed:

Date Submitted:

Faculty In-charge
 School of Chemical, Biological and Materials Engineering and Sciences

I. Introduction

In liquid-liquid extraction, the substances or solvents in a sample solution

were separated into immiscible liquids according to the reactivities and
solubilities of the present compounds (de Haan, Eral, & Schuur, 2020). This
process of separation is commonly applied in the agricultural, pharmaceutical,
and food safety industries. Example of the practices are extractive metallurgy
of phosphorus and potassium for agricultural industries; fermentation of amino
acids, antibiotics, and steroids for pharmaceutical industries; and determination
of pesticides in food for food safety industries (de Haan, Eral, & Schuur, 2020;
Khatibi, Hamidi, & Siahi-Shadbad, 2020). This experiment aims to separate
caffeine from soda, coffee, and tea through liquid-liquid extraction using
dichloromethane. From this, the following sub-objectives are expected: (1) to
discuss the fundamentals and processes behind extraction theory, (2) to
determine the components in each liquid layers, (3) to demonstrate the steps
and techniques in liquid-liquid extraction in order to separate caffeine.

II. Theory

In the English language, extraction means drawing something out of an

object (The World Publishing Company, 1959). The same idea goes in
chemistry. Liquid-liquid extraction, also known as solvent extraction, or simply
extraction refers to the selective separation or isolation of substances from a
liquid mixture or solution using their relative solubilities, whether compounds
are miscible or immiscible liquid, and their reactivities, mechanisms undergoing
reversible reactions (Schimdt & Strube, 2000). Furthermore, extractions which
demand chemical reaction or interaction, a subsequent method of separation
is required in order to reverse the formation of these complex compounds while
extractions relying on physical means, distillation or other modes of separation
are performed (Hanson, 1971).

Caffeine (1,3,7-trimethylxanthine or 1,3,7-trimethyl-2,6-dioxopurine) is an

odorless, colorless solid powder compound at room temperature with a bitter
taste (Tarka, Jr. & Hurst, 1998). It has been widely consumed around the world
and around 80% of adults consume it from various forms and sources (Dews,
1982). Most importantly, caffeine is known for its pharmacokinetic and
metabolizing properties and their effect on the physiology of the human body
(Dews, 1982). On the other hand, dichloromethane (CH2Cl2) is a volatile,
colorless, polar, and sweet-odored liquid which is commonly used as a solvent
and is immiscible in water (Chemical Entities of Biological Interest , 2016).
 School of Chemical, Biological and Materials Engineering and Sciences

III. Methodology

The materials needed for the extraction of caffeine were dichloromethane

(DCM), soda, coffee, and tea. Whereas the apparatus or equipment required
for the experiment were a Buchner funnel, 4 pcs. of Erlenmeyer flasks, filter
papers, a heating plate, an iron clamp, an iron stand, a glass funnel, a
separatory funnel, and a vacuum filtration flask. The step-by-step process of
liquid-liquid extraction of caffeine from the samples, namely coffee, tea, and
soda, were shown in Figure 1.

Figure 1. Process Flow Diagram for the Isolation of Caffeine through Liquid-
Liquid Extraction

IV. Results

In Table 1, it tabulates the data recorded in the experiment about the

isolation of caffeine through liquid-liquid extraction such as the volume of the
coffee sample used, the mass of extracted caffeine after removing DCM
through evaporation, and the percent recovery of caffeine.

Volume of the coffee sample 100 mL

Mass of extracted caffeine 0.036 g
Percent recovery of caffeine 0.036 %

Table 1. Complete Date for the Isolation of Caffeine through Liquid-Liquid

Extraction
 School of Chemical, Biological and Materials Engineering and Sciences

V. Discussion

After separating the caffeine using the funnel, the caffeine exists in both the
organic and aqueous state which is the reason multiple stages of separation
must be performed. Then, the extracted solution was heated in order to remove
the solvent which is DCM through evaporation. The remaining substance which
is caffeine was weighed and the measured mass was 0.036 g and the percent
recovery 0.036 %. As stated in the experiment, there are 40 mg of caffeine in
100 mL of coffee. Looking at the measured mass of caffeine, it is close to the
data stated before the start of the experimentation process.

From the experiment, it can be concluded that we are able to discuss the
fundamentals and processes behind extraction theory, to determine the
components in each liquid layers, and to demonstrate the steps and techniques
in liquid-liquid extraction in order to separate caffeine.

VI. References

Cesaro, A., Russo, E., & Crescenzi, V. (1976). Thermodynamics of Caffeine

Aqueous Solutions. The Journal of Physical Chemistry, 80(3), 335-339.
doi:10.1021/j100544a026
Chemical Entities of Biological Interest . (2016, December 15).
dichloromethane. Retrieved from Chemical Entities of Biological Interest
: https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15767
de Haan, A. B., Eral, H. B., & Schuur, B. (2020). Chapter 5. Liquid–Liquid
Extraction. In A. B. de Haan, H. B. Eral, & B. Schuur, Industrial
Separation Processes (pp. 117-154). De Gruyter: Berlin.
doi:10.1515/9783110654806-005
Dews, P. B. (1982). Caffeine. Annual Review of Nutrition, 2(1), 323-341.
doi:10.1146/annurev.nu.02.070182.001543
Hanson, C. (1971). Solvent Extaction: The Current Position. In C. Hanson
(Ed.), Recent Advances in Liquid-Liquid Extraction (pp. 1-14). Oxford:
Pergamom Press.
Khatibi, S. A., Hamidi, S., & Siahi-Shadbad, M. R. (2020). Application of liquid-
liquid extraction for the determination of antibiotics in the foodstuff:
Recent trends and developments. Critical Reviews in Analytical
Chemistry, 1-16. doi:10.1080/10408347.2020.1798211
 School of Chemical, Biological and Materials Engineering and Sciences

Schimdt, A., & Strube, J. (2000). Application and Fundamentals of Liquid–

Liquid Extraction Processes: Purification of Biologicals, Botanicals, and
Strategic Metals. In C. Ley (Ed.), Kirk-Othmer Encyclopedia of Chemical
Technology (pp. 1-52). Hoboken: John Wiley & Sons, Inc.
doi:10.1002/0471238961.koe00041
Tarka, Jr., S. M., & Hurst, W. J. (1998). Introduction to the Chemistry, Isolation,
and Biosynthesis of Methylxanthines. In G. A. Spiller, Caffeine (1st ed.,
pp. 1-9). Boca Raton: CRC Press. doi:10.1201/9780429126789
The World Publishing Company. (1959). New Handy Webster Dictionary: An
Illustrated Self-Pronouncing Dictionary of the English Language.
Cleveland: The World Publishing Company.

VII. Appendix

Calculating for the Percentage Recovery of Extracted Caffeine

Assume density of coffee as 1 g/mL

mass of coffee sample = volume of coffee sample x density of coffee

= 100 mL x 1 g/mL
= 100 g

mass of extracted caffeine

%recovery = x 100%
mass of coffee sample
0.036 g
= x 100%
100 g
= 0.036 %