EXPERIMENT 2

Liquid-liquid Extraction of Caffeine from Tea Leaves (Cameila sinensis)

Objectives

● To extract caffeine from commercial green tea samples by applying both solid-
liquid extraction and liquid-liquid extraction

Figure 2.1 | Structure of Caffeine

● To demonstrate the proper techniques in liquid-liquid extraction

● To calculate the % recovery for the recrystallization process

Safety Precautions

Organic solvents and bases can injure your skin and eyes. Avoid direct contact
with these chemicals. Should you accidentally get some on your skin, rinse the area
well with running water for several minutes. If the area of exposure is your eyes, it is
very important that you use the eye wash for a minimum of five minutes.

Dichloromethane (DCM) is a suspected carcinogenic compound. Avoid direct

contact and inhalation of this compound. If possible, work in a fume hood or in a well-
ventilated area.

Solid Na2CO3 and Na2SO4 may irritate your nose. Always wear proper personal
protective equipment (PPEs).

Notify your instructor or have a fellow student alert the instructor to any accident.

Procedure

This experiment is to be done in groups of two. Collaboration is important and

you are expected to discuss all results and observations with your partner. Be sure to
record your partner’s observations in your laboratory notebook.

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 Liquid-liquid extractions will be done in a separatory funnel. As much as possible,
use clean and dried glassware in measuring the solvents and reagents to avoid
contamination. Record or take a picture of all observations, both before and after mixing
the materials or chemicals.

1. Place 200 mL of distilled water, 5.0 g sodium carbonate (Na 2CO3), and 2-3
pieces of boiling chips in a 400 mL beaker. Heat the solution to boiling.

2. Weigh the contents of 5 – 6 green tea bags sample. After recording the mass,
return the tea leaves inside the bag and staple them.

3. Upon boiling of the aqueous carbonate solution, add the weighed tea bags. Turn
off the heat source and let the tea sit for five minutes with occasional stirring.

4. After brewing the tea, decant the liquid to a new 400 mL beaker. Try not to carry
over the solids from the brewing step (liquid-solid extraction). (Note: If there is
solid present, filter it.) This will be the aqueous layer (A) for the remaining steps.
Let the solution cool to room temperature.

5. Measure and record the volume of the aqueous solution (A) using a graduated
cylinder. Transfer the aqueous tea extract in a separatory funnel containing 50
mL dichloromethane (DCM) (organic layer, O), and extract the caffeine.

6. Close the funnel with the stopper and shake vigorously. Release pressure
constantly. Wait until the separation between the two layers is evident. Drain the
DCM lower layer into a clean Erlenmeyer flask.

7. Return the aqueous layer into the separatory funnel. Repeat another round of
extraction twice, i.e., 50 mL DCM x 2. Combine all CH 2Cl2 portions.

8. Return the combined DCM layers into the separatory funnel and wash with 100
mL 10% NaOH solution.

9. Drain the DCM layer into a clean, dry 250-mL Erlenmeyer flask. Discard the
NaOH layer.

10. If there is an emulsion formed, wash the organic extract with 100 mL saturated
sodium chloride solution.

11. Drain the DCM layer into a clean, dry 250-mL Erlenmeyer flask. Discard the
sodium chloride solution.

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 12. Using your spatula, add anhydrous sodium sulfate (Na 2SO4) until no clumps are
observed. Swirl and allow the Na2SO4 to settle and filter.

13. Evaporate the solvent using a hot water bath in the fume hood. When the volume
of the extract is less than 50 mL, transfer the contents into a clean, dry pre-
weighed 50-mL Erlenmeyer flask. Continue heating until a few amounts of the
solvent is left. (Do not heat to dryness)

14. Cover the flask with aluminum foil and let it cool. When the flask is at room
temperature, weigh the flask. Compute the percent recovery the following
equation:

mass of caffeine extracted ( g)

Percent Recovery = x 100 %
mass of tea leaves sample ( g)

Waste Disposals

Combine all organic mixtures in a beaker and dispose the mixture in the
halogenated organic waste container.

Combine all aqueous layer extracts then dispose this in the organic-aqueous
waste container.

Dissolve unused Na2CO3 and Na2SO4 in water before disposal in the inorganic-
aqueous waste container.

All chemically contaminated materials (i.e., tissues, gloves, paper towels, etc.)
should be disposed of in the chemical solid waste bins.

Dispose of used boiling chips on ‘broken glassware’ container.

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REPORT SHEET SAMPLES

Complete the following data or information.

Mass of tea leaves (g)

Mass of Na2CO3 (g)

Volume of H2O (mL)

Volume of aqueous extract (mL)

Volume of DCM (1st, mL)

Volume of DCM (2nd, mL)

Volume of DCM (3rd, mL)

Volume of 10% NaOH solution (mL)

Mass of Empty 50-mL Erlenmeyer flask

Mass of 50-mL Erlenmeyer flask + Crude

Caffeine

Mass of Crude Caffeine (g)

% Recovery of caffeine

Paste on the boxes below the picture of the crude caffeine. Label the boxes properly.

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