University of Puthisastra

Department of Pharmacy

PW of Organic chemistry

Unit 4: Extraction Technique

 Extraction Technique

Objective :
1. Understand and usefulness the extraction method to purify of
compounds
2. Apply extraction technique to isolation of principle compound from
plants
 Extraction Technique
I. Introduction
☞ Extraction is one of the most important techniques for isolating and
purifying organic substances from plants

benzoic acid

Caffeine

Naphthalene

2-naphthol

Piperine
 Extraction Technique
I. Introduction
☞ Principle of extraction bas on the solubility of compound
relatively to 2 phases
-Density of Ether = 0.713g/ml
-Density of ED =1g/ml

benzoic acid Ether

Solubility :
0.24 g / 100ml of ED
2.70 g/ 100ml of Ether

ED
If we add 1.47g benzoic acid in mixed of ED/Ether.
- What’s the medium that content the high concentration of
benzoic acid ?
- What’s the % of benzoic acid in ether ?
 Extraction Technique
I. Introduction
☞ There are 3 types of Extraction:

❶Solid-Liquid extraction ❷Liquid-Liquid extraction

❸Acid-Base extraction
 Extraction Technique
II. Principle of Liquid-Liquid Extraction

• It involves shaking the liquid mixture with an

immiscible solvent which preferentially dissolves the
desired compound.
 Extraction Technique
II. Principle of Liquid-Liquid Extraction

• It involves shaking the liquid mixture with an

immiscible solvent which preferentially dissolves the
desired compound.
 Extraction Technique
II. Principle of Liquid-Liquid Extraction
☞ Practice advice on extraction :
1. Density of the solvent used for the extraction
2. Temperature of the extraction mixture
3. Venting the separatory funnel and why it is necessary
4. Improving the efficiency of an extraction by salting out if the
distribution coefficient is less than 2.0
5. Preventing and dispersing emulsions
6. Caring for the separatory funnel after an extraction
 Extraction Technique
II. Principle of Liquid-Liquid Extraction
☞ Practice advice on extraction :
1. Density of the solvent used for the extraction
2. Temperature of the extraction mixture

Ether : d = 0.71
ED : d =1

Solubility :
We want extract Salicylic in Ether/ED 0.24 g / 100ml of ED
(400C) ? 2.70 g/ 100ml of Ether

☞ What’s happen when we start extraction of warm aqueous solution ( ≈ 40 0C )

with Diethyl ether ?
 Extraction Technique
II. Principle of Liquid-Liquid Extraction
☞ Practice advice on extraction :
3. Venting the separatory funnel and why it is necessary

☞ Vent the extraction mixture immediately after the first inversion

and subsequently after every three or four inversions.

Failure to vent the separatory funnel when

extracting with Na2CO3 or NaHCO3 solution
can cause the stopper to pop out.
 Extraction Technique
II. Principle of Liquid-Liquid Extraction
☞ Practice advice on extraction :
4. Improving the efficiency of an extraction by salting out if the
distribution coefficient is less than 2.0
5. Preventing and dispersing emulsions
-Density of Ether = 0.713g/ml
-Density of ED =1g/ml
Compound A
Solubility :
0.5 g / 100ml of ED
1 g/ 100ml of Ether

K =[ substant]sol 1 /[ substant]sol 2

Salting out is done by adding a

saturated solution of NaCl
 Extraction of Caffeine from Coffee

I. Introduction
Caffeine Caffee Cocoa beans kola nuts

➔ Caffeine is an alkaloid in the xanthine family that present in some 60 plant

species, of which cocoa beans, kola nuts, tea leaves and coffee beans
➔ Liquid-liquid extraction technique :
- Selection of 2 immiscible solvents
Solvent Temperature Solubility of
☞ Which are the 2 immiscible solvent (◦C) caffeine (% w/w)

use to ? Water 25 2.2

Water 100 66.7

EtOH 25 1.2

EtOH 60 4.5

Ether 25 0.3

Ethyl Acetate 25 2.5

Chloroform 25 18.0

Acetone 25 2.0

Benzene 25 1.0
 Extraction of Caffeine from Coffee
CH2Cl2 d= 1.32
ED d = 1
II. Procedure
Place 10g of sodium carbonate and 15 g of instant soluble coffee in a 250 ml
beaker.Add hot deionized water (150 ml), stir the mixture, and heat until boiling.
Then cool the mixture to r.t. Pour the contents of the beaker into separatory
funnel and add 10 ml of CH2Cl2 . shaking the liquid mixture and allow to stable.
Collect the organic layer repeat 2 times . add 1g of Na 2SO4 and filtration ,
evaluation , recrystallization with EtOH
10 ml of CH2Cl2 10 ml of CH2Cl2

10 g of NaCO3 stir the mixture Cooling at r.t

15 g of Coffee powder
150 ml of hot ED Filtrate
heat until boiling

Wash with 15 ml of CH2Cl2

Add 1g of Na2SO4
Add EtHO
to dissolve

Recrystallization
Cooling at r.t
 Extraction of Caffeine from Coffee

1. What’s physical property of solvent that use in liquid-liquid extraction?

2. When we use heat in liquid-liquid extraction, What are the precaution ?
3. For what purpose is Na2SO4 used in liquid-liquid extraction ?
4. Explain about your ideas about choice Water/CH2Cl2 to extraction of
caffeine ?
References

- A microscale Approach to organic laboratory techniques , Donald

L.Pavia,Gary M. Lampman ,5th edition
- Experimental Organic Chemistry : A Miniscale and Microscale
Approach, John C. Gilbert ,Stephen F.Martin ,5th edition
- Quantitative Chemical Analysis 7th edition , Daniel C.Harris.
- Introduction to Laboratory techniques , Pavia Kriz ,Lampman Engel ,
1998
- Techniques in Organic Chemistry , 3rd edition , Jerry R.Mohrig ,
Christina Noring Hammond Paul F.Schatz
- Pharmacopeia European ,7th edition ,2010