CHEM 3760

TECH 705 Extraction

Objectives
Solvent-solvent extraction is a technique used to
separate components of a mixture that have very
different solubilities in each of two solvents which are
immiscible.
One solvent is usually water, the other a volatile
organic solvent of low or moderate polarity (e.g., ethyl
acetate or diethyl ether).
The efficiency of the separation (partitioning) depends
on the relative solubilities of the components to be
separated in the two immiscible solvents.

CHEM 3760
TECH 705 Extraction
Separatory Funnel Technique
The separatory funnel is suspended on
an iron ring in the hood.
Be sure to remember to tighten the
stopcock before use (it should be
loosened for storage).
Add the two solvents and the
substance to be extracted. Do not fill
the separatory funnel more than 3/4 full
so as to allow room for agitation.
Stopper the funnel.

CHEM 3760
TECH 705 Extraction
Separatory Funnel Technique

Cradle the funnel with your

fingertips of one hand and invert
the funnel gently, then open the
stopcock to release the pressure.
(Make sure the tip is pointed into
the hood before you vent.)
Close the stopcock, rock the
funnel gently a few times, invert it
and vent the pressure as before.
Agitate again, venting the
pressure several times.
DONT FORGET TO VENT!

CHEM 3760
TECH 705 Extraction
Separatory Funnel Technique

Place the separatory funnel in the iron

ring attached to supports in the hood
and let the two layers (phases) separate.

Remove the stopper, and drain the lower

layer through the stopcock.

Pour off the top layer out of the top of

the separatory funnel.

Be sure to label each phase that you

remove from the separatory funnel.
(It is best to keep all phases until you
are sure that you have the desired
product. Then the others may be
discarded as directed.)

CHEM 3760
TECH 705 Extraction
Acid-Base Properties of Organic Compounds

CHEM 3760
TECH 705 Extraction
O

ter t-butyl methyl ether (MTBE)

OH
+

H3C
H3C

O
+

CH3

OH
H3C
p-toluic acid

p-tert-butylphenol

biphenyl
MIX
NaHCO3 solution

aqueous layer

ether layer
(extraction)
OH
+
biphenyl

H3C
H3C

O
O

CH3 p-tert-butylphenol

4
3

NaOH solution

ether layer

Na

p-toluic acid

H3C

HCl solution

filtrate

residue
(filtration)

aqueous layer

discard

(extraction)

O
OH
O

biphenyl

H3C
H3C

Na2SO4
anhydrous

decantate

CH3
5

residue
(decantation)
discard

H3C

Na

p-tert-butylphenol
HCl solution

filtrate

residue
(filtration)

discard
OH

biphenyl
H3C
H3C

vapor
residue
(evaporate)
discard

biphenyl

CH3

p-tert-butylphenol

p-toluic acid

CHEM 3760
TECH 705 Extraction

Using the Mel-Temp

Preparing the sample
Place the open end of a
capillary tube in a finely
ground sample of a solid.
If you can see the sample
in the tube, you have
enough (~1 to 2 mm)
Tap the capillary tube on
the bench to force the
sample to the closed end
of the tube.

CHEM 3760
TECH 705 Extraction

Using the Mel-Temp

Taking the melting point
The Mel-Temp should be
close to room
temperature.
Insert the capillary tube in
one of the three slots and
place your thermometer
into the larger opening.

(Thermometer)

CHEM 3760
TECH 705 Extraction
Using the Mel-Temp
Monitor your sample with your eye about six inches
away from the viewfinder.
Adjust the control knob as specified by your T.A. for the
experiment.
You will record two temperatures: the temperature at
which your sample begins to melt, and the temperature
at which the last portion of solid melts completely.
Record the melting point of your compound as a range in
your lab notebook.

CHEM 3760
TECH 705 Extraction
Drying Organic Solvents

Organic solvents which have come in contact with water will have
some water dissolved in them, even though they are immiscible with
water. (Organic layers containing water appear cloudy.)

The solubility of water in organic solvents is dependent upon

intermolecular forces:
Hexane 0.01 g / 100 g
Diethyl ether 1.26 g / 100 g
Ethyl Acetate 3.3 g / 100 g

Water can be removed from organic compounds when the compound

is in solution by using a drying agent.

Drying agents are anhydrous salts which readily form hydrates, which
can then be removed by filtration or by decanting.

CHEM 3760
TECH 705 Extraction
Calculation of Percent Recovery
The percent recovery represents the amount of each
component (biphenyl, p-toluic acid, and p-tertbutylphenol) that are isolate upon completion of the
extraction.
% Recovery =

weight of isolated compound

initial weight of compound

x 100

Remember to accurately weigh both the starting

amount of material used in the extraction
experiment and the recovered amount of
compound.