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Exp - 2, Extraction Lab - 97-2003

This experiment involves separating a mixture of three organic compounds (benzoic acid, 2-naphthol, and naphthalene) using a two-base extraction procedure, which utilizes sodium carbonate and sodium hydroxide bases to extract the compounds into aqueous layers based on their solubility properties, followed by acidification, crystallization, filtration, and analysis to obtain purified samples of each compound. Safety precautions for venting separatory funnels and proper waste disposal are also outlined.

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126 views

Exp - 2, Extraction Lab - 97-2003

This experiment involves separating a mixture of three organic compounds (benzoic acid, 2-naphthol, and naphthalene) using a two-base extraction procedure, which utilizes sodium carbonate and sodium hydroxide bases to extract the compounds into aqueous layers based on their solubility properties, followed by acidification, crystallization, filtration, and analysis to obtain purified samples of each compound. Safety precautions for venting separatory funnels and proper waste disposal are also outlined.

Uploaded by

venu11chemist
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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Experiment # 2

Two- base extraction


• Flow Chart

Impure
compound

Isolation Extraction

• Recrystallization
• Distillation
Purification • Chromatography

• Melting point
Establishing • Boiling point
purity • Spectroscopy
What is extraction all about !
• The technique, extraction is employed for the isolation of the desired
product from the reaction mixture

• The extraction procedure involves partitioning the reaction mixture


between two immiscible liquids , an organic solvent and water.

• The usual organic extracting solvents are dichloromethane ( CH2Cl2 ),


ether ( CH3CH2OCH2CH3 ), ethyl acetate (CH3COOCH2CH3 )

• Except dichlorormethane and chloroform, all other organic solvents


ocupy top layer

• To test which layer is which add a drop of water to the separatory


funnel having two layers, if the water drop pass the top layer and goes to
the bottom layer then the bottom layer is aqueous layer.
Solubility rules
• This separation technique makes use of three solubility rules

1. Organic compounds are soluble in organic solvents


(exceptions)

2. Ionic compounds (salts) are soluble in water but insoluble


in organic solvents.

3. Organic compounds containing greater than 4 carbons are


insoluble in water
Theory of extraction
• The extraction involves partitioning of compounds between two immiscible
phases,Sx , the extracting phase, and So , the original phase

• The partitioning of compounds is due the difference in solubilities of a


substance in two immiscible solvents.

• The ratio of the solute distributed between the two phases will depend on
the relative solubilities of the solute in each phase.

• At a given temperature, the ratio of concentrations of a solute in the two


phases will always be constant, known as the distribution coefficient or the
partition coefficient, K, and is an equilibrium constant.

• The concentrations of solute in each solvent are approximated to the


solubilities of the solute in the pure solvent
[A] in Sx Solubility of A in Sx grams of A in Sx ml of So
K = = = X
[A] in So Solubility of A in So grams of A in So ml of Sx
Theory of extraction cont’d
Consider a compound, A, which dissolves in ether to the extent of 12g/100 ml
and dissolves in water to the extent of 6 g/100ml

K = 12 g/100 ml ether = 2
6 g/100 ml water
If a solution of 6g of A in 100 ml of water is shaken with 100 ml of ether then

K= ( x g of A/100 ml ether)
=2
(6 - x g of A /100 ml water)

From which x = 4.0 g of A in the ether layer


6 – x = 2.0 g left in the water layer

It is, however, more efficient to extract the 100 ml of aqueous solution twice
with 50 ml portions of ether rather than once with a 100 ml portion
( x g of A/50 ml ether)
K = = 2
(6 - x g of A /100 ml water)

From which x = 3.0 g of A in the ether layer


6 – x = 3.0 g left in the water layer
Theory of extraction cont’d
• If this 3.0 g/100ml of water is extracted once more with 50 ml of ether
we can calculate that 1.5 g will be in the ether layer, leaving 1.5 g in
the water layer.

• So two extractions with 50 ml portions of ether will extract total


3.0g + 1.5g = 4.5 g of A, while one extraction with a 100 ml portion
of ether removes only 4.0 g of A.

• Three extractions with 33 1∕3 ml portions of ether would extract


4.7 g.

• In general the fraction of solute A, FA , in original solvent after ‘n’


extractions is given by
n

Conclusion : Multiple extractions are better than one large one.


Types of extraction

Extraction

Simple Acid-Base
extraction extraction
Acid-Base
extraction
Mechanism
Two-Base Extraction
Aim : The aim of the experiment is to separate a mixture of
three organic compounds, benzoic acid, 2 – naphthol,
and naphthalene.

Apparatus: Separatory funnel, ice water bath, apparatus


for vacuum filtration, Erlenmeyer flasks

Dissolution: Dissolve 1.5 g of the mixture by swirling it


with 30 ml of diethyl ether in a 125 ml Erlenmeyer flask

Extraction:
1. The ether solution is transferred to a separatory funnel
and 20 ml of 1.25M (10%) aqueous sodium carbonate
is added to it. Now swirl the unstoppered funnel until all
foaming has subsided. Then stopper the funnel and,
holding both the stopcock and the stopper of the funnel
tightly, invert the funnel and immediately vent it by
opening the stopcock. Finally, shake the funnel with
frequent venting until gas is no longer evolved.
Separate the layers, transferring the aqueous layer to a
125 ml Erlenmeyer flask labeled “ Bicarbonate Extract”
Extraction procedure cont’d
Extract the organic solution with a 20 ml of 2.5 M
(10%) aq. sodium hydroxide, venting the funnel
frequently during the process. Transfer the
aqueous layer to a 125 ml Erlenmeyer flask
labeled “Hydroxide Extract.” Transfer the
organic solution to a 50 ml Erlenmeyer flask
labeled “Neutral Compound” and containing
two spatula-tips of anhydrous sodium sulfate.
Loosely film the flask with paraffin film, and let
it stand for at least 15 min with occasional
swirling.

Note : Shake gently to avoid emulsions. Emulsion


is a suspension of one liquid as droplets in
another

Precipitating and Drying : Cool the “Hydroxide


Extract” in an ice-water bath. Carefully acidify
this solution with 3M hydrochloric acid, so that
the solution is distinctly acidic to pH paper.
Upon acidification, a precipitate should form;
cool the mixture for 10-15 min to complete the
crystallization.
.
Extraction procedure cont’d

• Collect the precipitate by vacuum filtration using a Buchner or Hirsch funnel.


Wash the solid on the filter paper with a small portion of cold water. Transfer
the solid to a labeled watchglass, cover it with a piece of filter paper, and allow
the product to air-dry until the next laboratory period. After drying, transfer the
benzoic acid to a dry, tared vial.

• For the Bicarbonate extract follow the same procedure

• Separate the “Neutral Compound” from the drying agent by decantation into a
beaker. Keep it in the drawer until the next lab period so that the solvent is
evaporated. Scrape the contents of the beaker onto a piece of weighing paper
and then transfer it to a dry, tared vial.

Analysis : Determine the melting point of each crude product.


Safety

• Always point the stem of the separatory funnel away from others during
venting .

• Wear always safety goggles and gloves.

Disposal
• Dispose of the filter papers in solid waste container.
• Flush the acidic filtrates down the drain.
• Lab Report
 This should cover
1. Introduction
2. Reaction and mechanisms
3. Table of reagents
4. Table of reactants
5. Procedure
6. Flow chart
7. Observations
8. Results
9. Conclusions and discussions
 Due Friday, 02/04/2011.

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