[Type text]

Name: Erica Joy. David Date Performed:

Year & Section: DDM II-A Date Submitted:

Score: Instructor:

EXPERIMENT 2: EXTRACTION

2.1 OBJECTIVE

 Compare single and multiple extractions of caffeine from dried tea leaves.
 Calculate the percentage yield of caffeine for both extraction procedures.

2.2 BACKGROUND INFORMATION

Organic chemical reactions result from the mixture of organic and inorganic compounds. Every reaction involves
products, by produces, and starting materials. Some products can differ significantly from others in the way they
distribute themselves between two immiscible liquids. Such differences are useful in any extraction procedure.

2.3 MATERIALS

Bunsen burner Iron Ring

Separatory Funnel Iron Clamp

Beaker Teabags

Glass Rod Sodium Carbonate

Evaporating Dish Dichloromethane

Iron Stand Sodium Sulfate

2.4 PROCEDURE

1. Place 4.4g of anhydrous sodium carbonate in a 500ml beaker and add 100ml of distilled water. Heat in a water
bath until the solid dissolves.
2. Add 10g of tea leaves contained in a teabag to the said mixture. Cover the flask and boil the tea mixture for 10
minutes in a low flame.
3. Remove the tea bag and squeeze the liquid by pressing it against the side of the flask using a glass rod. Allow the
extract to cool to room temperature.
4. For the odd-numbered groups (single extraction), extract the aqueous solution with 60ml of dichloromethane in a
separatory funnel. Let it stand for 2 minutes or until the separation between two layers is clearly visible. Drain the
organic layer into clean Erlenmeyer flask. Discard the aqueous layer.
For the even-numbered groups(multiple extraction), extract the aqueous solution three times with 20ml of
dichloromethane each time in a separatory funnel. Let it stand for 2 minutes or until the separation between two
layers is clearly visible. Drain the organic layer into a clean Erlenmeyer flask. Discard the aqueous layer. Combine
all organic layer extracts.

CAUTION! DICHLOROMETHANE IS A SUSPECTED CARCINOGEN

5. Tansfer the extract into an Erlenmeyer flask containing half a spatula of anhydrous sodium sulfate. Decant into a
tared evaporating dish. Evaporate to dryness under the hood. Weigh the residue and calculate the percentage
recovery of caffeine.
[Type text]

QUESTIONS:

1. WHAT IS THE PRINCIPLE INVOLVED IN EXTRACTION?

Extraction is a technique used in chemical or biochemical processes to separate two or more different compounds based on
their relative solubilities in two different immiscible liquid solvents usually water (polar) and an organic solvent (non-polar).
There is a net transfer of one or more species from one liquid into another liquid phase, generally from aqueous to organic. The
transfer is driven by chemical potential, i.e. once the transfer is complete, the overall system of protons and electrons that make
up the solutes and the solvents are in a more stable configuration (lower free energy). The solvent that is enriched in solute(s) is
called extract. The feed solution that is depleted in solute(s) is called the raffinate. LLE is a basic technique in chemical
laboratories, where it is performed using a variety of apparatus, from separatory funnels to countercurrent
distribution equipment called as mixer settlers. This type of process is commonly performed after a chemical reaction as part of
the work-up, often including an acidic work-up.

2. DRAW THE STRUCTURES OF CAFFEINE, THEOBROMINE, THEOPHYLLINE, FLAVANOID,

TANNIN.

CAFFEINE THEOBROMINE THEOPHYLLINE

FLAVANOID TANNIN
[Type text]

3. WHAT IS THE ROLE OF SODIUM CARBONATE IN THE EXTRACTION OF CAFFEINE FROM

TEA LEAVES?

The sodium carbonate acts as a base - you could use sodium hydroxide instead. When you boil tea
leaves tannins dissolve in the water as well as the caffeine. If you do not use a base the tannins will also
be extracted into the solvent (i.e. methylene chloride) used in the subsequent extraction.

4. WHICH OF THE TWO LAYERS THAT FORM DURING THE EXTRACTION IN THE
DICHLOROMETHANE, EXPLAIN.

We have an aqueous solution of our tea extract from which you will extract the caffeine. In order to get
the caffeine out we have to extract it into an organic solvent (in your case dichloromethane). Add our
aqueous tea solution to a separatory funnel. Next add dichloromethane. Shake up the two immiscible layers
and let them sit until they separate. The dichloromethane layer will be the one on the bottom because
dichloromethane is denser than water.

5. DATA AND RESULTS:

 Weight of tea leaves used

- 10 grams
 Weight of the evaporating dish
- 83.5 grams
 Weight of the evaporating dish and the caffeine
- 85 grams
 Weight of caffeine (Residue)
- 1.5 grams

6. RECOVERY (SHOW COMPUTATION)

Percent recovery = amount of substance you actually collected / amount of substance we were supposed to collect, as a percent.

So another way of putting it:

Percent Recovery = (pure/impure) x 100
We had 10.0g of impure material and after recrystallization we collected 1.5 g of caffeine. Then our percent recovery is 15% (1.5/10
x 100).