FACULTY OF SCIENCE, TECHNOLOGY AND MATHEMATICS OrganicxBiochemistry

Experiment #: 1
Experiment Title: Liquid Liquid Extraction

Group #: 1

Denilyn Madrid1, Renyrick Manaloto1, Carla Bianca Salutin1

1
FSTEM, CTD, Philippine Normal University, Taft Avenue, Malate, Manila

Date Performed: 05/12/2021

Date Submitted: 06/16/2021

I. Read: Williamson, K. L., & Masters, K. M. (2011). Macroscale and microscale Organic
experiments. In Macroscale and microscale organic experiments (6th ed., pp. 131-145).
Boston, MA: Cengage Learning.
II. Watch the Pre-Lab Video Series
III. Explore and Perform the Simulation experiment for Liquid-Liquid Extraction.
IV. Answer the Guide questions.

a. Liquid-Liquid Extraction Simulator Procedure

1. Begin the animation with “Click Here to Start Experiment,” and click
“continue” to proceed through each steps.
2. After the animation pauses, please read the onscreen notes provided
before clicking “continue.”
3. You may click on any blue text to learn more.

Note: This animation represents some of the steps you are likely to take after
quenching an organic reaction with water (perhaps aq. acid or aq. base), so
the reaction mixture will be the aqueous phase in the separatory funnel. It is
colored blue to make it visible, and the blue circles and blue dots represent
solutes.

b. Data Sheet

1. Sketch a separatory (“sep”) funnel and label the following parts:

a. ring stand
b. stopcock
c. stopper
d. stem
e. support ring

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2. Draw a schematic diagram of the experiment.

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3. Note any precautionary measures that need to be observed in doing this

experiment.

 Wearing of protective gears to protect yourself (e.g gloves,

laboratory coat, goggles...etc)
 Proper handling of chemicals or solutions when doing the
experiment.
 Using a (small glass) funnel when pouring the solution into
another container to avoid any spillages.

4. Record your observation in the table below:

Observation
Steps
1st Extraction
After removing the impurities on the solution with water, it
Step 1 was poured on the sep funnel, and to make sure that no
product will be wasted, they use ether.
Then, they add ether and water to wash the solution to the
Step 2
sep funnel.
Step 3 They closed the sep funnel with the stopper.
They remove the sep funnel in the apparatus/ring stand,
and they make sure first that the stopper is closed before
they carefully invert the funnel. Then, they gently shake the
Step 4
funnel and from time to time, they open the stop cock to
release the pressure. It was done several times to ensure
the solutions are mixed.
After that, they put the funnel back in the ring stand and wait
until the solutions are separated again. Then, we can see
Step 5
that the ether layer is on the top and the denser aqueous
solution is at the bottom.
The stopper is removed first and then they put the empty
Step 6 flask under the stem before opening the stop cock and drain
the bottom layer.
Then, the first flask was removed and was replaced with
Step 7 another empty flask and the remaining solution was drained
out.
The steps were repeated but they use new ether to apply or
mix on the first solution (aqueous layer). Then, the last
drained solution (organic layer) was combined with the first
2nd Extraction
extracted organic layer. Then, we can see that there are
more aqueous solutions and the organic solution was lesser
in the aqueous layer.
The steps were repeated but they use new ether to apply or
mix on the first and second extracted solution (aqueous
layer). Then, the last drained solution (organic layer) was
3rd Extraction combined with the first and second extracted organic layer.
Then, we can see in the aqueous layer that it is an almost
pure aqueous solution and there’s almost no organic
solution.

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To wash the solution, we can use water which is done on

*Washing
the sep funnel.
To dry, a drying agent like magnesium sulfate was added
to the organic layer. When the solution formed a clump it
means that there should be more drying agent to mix on the
*Drying
solution because it’s still wet, but if there’s already a
“snowstorm effect” it means it is already enough and the
solution is already dry.
Now, they’ll remove the drying agent through gravity
*Solvent removal
filtration.

c. Guide Questions:
1. What is it necessary to mix the solvents well inside the separatory funnel?
It is important to mix the solvents well because it increases the
contact surface area and the distribution of solutes occurs rapidly.

2. Whys is there a need to vent out the separatory funnel?

It is necessary to vent out the separatory funnel because as you
shake and swirl the two immiscible and volatile solvents it builds up a
pressure, and this may force the stopper out and worst it could lead to
breakage of the apparatus.

3. What should you do if an emulsion was formed in your mixture?

There are a lot of options to deal with an emulsion, one of the
easiest way is just to swirl and stir it. If that doesn’t work, you can add
concentrated sodium chloride to increase the ionic strength of the aqueous
layer and decrease the solubility of organic solvent. If this still doesn’t work,
the last thing you can do is the vacuum filtration to filter the entire mixture.

4. What should you do if there is some question about which layer is the
organic one during an extraction procedure?
From our observation and according to the video, the usual location
of the organic solution is on the top part of the funnel. However, there are
materials or solutions that this observation can be applied so we can take
a look at the paper where the information of the solutions are or listen to
what the teacher has instructed.

5. Why is it necessary to remove the stopper from a separatory funnel when

liquid is being drained from it through the stopcock?
The reason the stopper was removed from a separatory funnel
when liquid is being drained is because of the pressure that should be
released and the process of draining out the liquid will be faster. Also, it
may stop the process of draining which can lead to another mixing of the
liquids or solutions.

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6. What are the separatory funnel etiquettes?

Some of the etiquettes for the separatory funnel are the following:
 Before performing the experiment, one should be checking if the
sep funnel’s parts are all in place and properly set up.
 When filling up the sep funnel, it should not be full a half-point is
enough.
 One should be careful when shaking the funnel, make sure that
the stopper is tightly closed to avoid spillage.
 After using the sep funnel, one should properly cleanse it and dry
it before storing it.

7. Differentiate washing and extraction.

The main difference between extraction and washing is the one that
we remove. For washing, we use a solvent to remove unwanted
compounds. On the other hand, extraction uses solvent too but the
compounds that we remove are the compound of interest or the compound
that we wanted.

8. Just prior to drying an organic layer with a drying agent, you notice water
droplets in the organic layer. What should you do next?
If there are water droplets present to the organic layer before drying,
it should be transferred to another container, which is the Erlenmeyer flask,
and add a solid drying agent to the solution. When it is done, you can now
proceed to completely drying it.

9. Saturated aqueous sodium chloride (d = 1.2 g/mL) is added to the following

mixtures in order to dry the organic layer. Which layer is likely to be on the
bottom in each case?
a. Sodium chloride layer or a layer containing a high-density organic
compound dissolved in methylene chloride (d = 1.4 g/mL)
The layer containing a high-density organic compound
dissolved in methylene chloride will remain in the bottom layer.

b. Sodium chloride layer or a layer containing a low-density organic

compound dissolved in methylene chloride (d = 1.1 g/mL)
Sodium chloride will be the bottom layer.

10. Why is multiple extraction better than single extraction?

Multiple extraction can definitely isolate our desired compound than
doing it just once.

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