Experiment 4 Extraction: An Aqueous Solution (Water) and An Organic Solvent

Experiment 4
EXTRACTION
Introduction
Extraction is a physical process used to separate a substance (solute) from a mixture. The idea consists of
shaking the mixture containing the substance to be extracted with an immiscible solvent. The solute distributes
itself between the 2 solvents according to its solubility in these two solvents. The two liquid phases are usually
an aqueous solution (water) and an organic solvent.
The extraction process is carried out in a separatory funnel.
Distribution Coefficient
The Distribution Coefficient (constant),KD= So/Sw

Where So is the solubility of the solute in the organic phase[g/mL] and Sw is the solubility of the solute in the
water phase[g/mL].
Choice of a good extraction solvent
A good extraction solvent must meet the following conditions:

(1) should be immiscible with water
(2) should have a low boiling point (volatile) so that it can easily be removed from the organic compound by
evaporation;
(3) should dissolve the substance to be extracted to a high extent
(4) should be nonflammable, nontoxic and cheap
Extraction organic solvents can be less dense than water and can be denser.
(1) Commonly used extraction solvents which are less dense include diethyl ether (the most common extraction
solvent of all- it is flammable and forms peroxides with air- may explode), ethyl acetate and hydrocarbons, such
as light benzene (cause cancer), hexane or toluene. [upper layer]
(2) The denser solvents comprise chlorinated solvents, such as dichloromethane, carbon tetrachloride (CCl4)
and chloroform (CHCl3), with dichloromethane being the preferred solvent because of its lower toxicity.
However, chlorinated solvents do have a greater tendency to form emulsions than non-chlorinated solvents.
[Lower layer]
Emulsions are suspensions of small droplets of one immiscible liquid in another.

In order to break an emulsion, one can follow one of the following steps:
 Swirl the separatory funnel
 Stir the emulsified layer with a glass rod
 Add a salt
 Centrifuge the whole mixture
Example: A particular extraction proceeds with a distribution coefficient of 4. The system consists of 50g of
organic compound (A) dissolved in 50mL of water (solvent 1). In this illustration the effectiveness of two 25mL
extractions with diethyl ether (solvent 2) is compared with one 50mL extraction with ether.
KD= 4 => the solubility of the organic compound (A) in diethyl ether is 4 times the solubility in water.
[1] Case one: Doing one extraction of 50 mL of ether.
KD= 4 = (x/50) /(50-x/50) => 4 = 50x /50 (50-x) => x = 40g extracted
% recovery = (40/50)*100 = 80%
[2] Case two: Doing 2 consecutive extractions of 25 mL of ether each time.
First extraction:
K = 4 = (x/25)/(50-x/50) => 4 = 50x / 25 (50-x) => x = 33g extracted
Therefore, 50-33=17g remains in water
Second extraction:
K = 4 = (x/25)/(17-x/50) => 4 = 50x / 25 (17-x) =>x = 11g extracted
Combine all two ether extracts (33+11) and there is 44g recovered from the ether extracts
% recovery = (44/50)*100 = 88%
Conclusion:
Multiple extractions is more efficient than a single extraction.
Acid-Base Extractions ( Extraction based on chemical reactions):

1) An organic base (amine, R ─ NH2) is extracted with a dilute mineral acid (5%HCl).
Organic base + Inorganic acid → Salt + Water

Non-polar polar (ionic, dissolves in water)
Example: + -
R ─ NH2 + HCl → R ─ NH3 , Cl
Amine group 5% dilute ionic compound, polar, dissolves in water,
Non-polar hydrochloric acid move to the upper layer
Organic salt + Inorganic base → Inorganic Salt + Organic base (recover)

Example:
R ─ NH3Cl + NaOH → NaCl + R ─ NH2
Salt1 base1 salt2 base2
2) An organic acid (R ─COOH) is extracted with a dilute mineral base (5%NaHCO3).
Organic acid + Inorganic base → Salt + Water

Non-polar polar (ionic, dissolves in water)
Example: - +
R ─ COOH + NaHCO3 → R ─ COO , Na
Carbonyl group 5% dilute ionic compound, polar, dissolves in water,
Non-polar sodium bicarbonate move to the upper layer
Organic salt + Inorganic acid → Inorganic Salt + Organic acid (recover)

Example:
R ─ COONa + HCl → NaCl + R ─ COOH
Salt1 acid1 salt2 acid2
3) Weak organic acids (phenols, Ø─OH) are extracted with 5%NaOH.

Sources of Errors:
There are some systematic errors in this experiment as we perform it.
 For example, you do not weigh the tea, you weigh the tea bag, which has not only tea but also string and
paper in its weight.
 When you squeeze the tea (liquid) out of the tea bag, some of the liquid (containing caffeine) remains
behind in the wet bag.
 some caffeine will remain behind in the water.

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Experiment 4

The Distribution Coefficient (constant),KD= So/Sw

Choice of a good extraction solvent

A good extraction solvent must meet the following conditions:

Emulsions are suspensions of small droplets of one immiscible liquid in another.

[2] Case two: Doing 2 consecutive extractions of 25 mL of ether each time.

Therefore, 50-33=17g remains in water

Acid-Base Extractions ( Extraction based on chemical reactions):

Organic base + Inorganic acid → Salt + Water

Organic salt + Inorganic base → Inorganic Salt + Organic base (recover)

2) An organic acid (R ─COOH) is extracted with a dilute mineral base (5%NaHCO3).

Organic acid + Inorganic base → Salt + Water

Organic salt + Inorganic acid → Inorganic Salt + Organic acid (recover)

3) Weak organic acids (phenols, Ø─OH) are extracted with 5%NaOH.

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