Page |1

Myeeka Hammond
May 24,2017
Extraction
Purpose: The most significant purpose of this experiment is to learn one of the
techniques for the separation of complex mixtures into individual components
and further understanding how to purify a mixture of compounds.
Introduction: Extraction is the selective transfer of any solute or impurity from
one phase into another. In any organic lab, the most common form of extraction
is liquid to liquid extraction, where a solute is transferred from one solvent, the
liquid phase, into another solvent, another liquid phase. This is the most useful
technique for separating a solute or an impurity from components in a mixture. A
term that is commonly used when talking about extractions distribution
coefficient, Kd. This simply refers to the ratio of the concentration of the solute in
each solvent, which is at equilibrium, at a specified temperature. Their two types
of extraction (1) batch extraction and (2) one time extraction. Of the two, batch
extraction is the better because multiple small extractions generate multiple
equilibrium stages of mass transfer of solute and are more efficient than a
onetime extraction which involves a single equilibrium stag of mass transfer of
solute. Since the partition coefficient of solute between the two solvents is
independent of the quantity of solvent being used for the extraction a large
volume of solvent in a onetime extraction is just adding cost without any value
addition. The main thing when doing an extraction experiment is knowing which
layer is the organic phase and which layer is the aqueous phase. In order to check
the identity of one of the layers, one must place a few drops of the layer into a
test tube containing water. If the layer is aqueous then the mixture should be
homogenous but if the layer is organic, two layers will form.
Materials:
1. One gram dimethoxybenze/benzoic acid mixture
2. A small Erlenmeyer flask
3. 45mL of diethyl ether
4. Ice bath
5. 10mL of 0.5 N sodium hydroxide
6. 125mL Erlenmeyer flask
7. 10mL of deionized water
8. One gram of anhydrous sodium sulfate
 Page |2
Myeeka Hammond
May 24,2017
Extraction
9. Litmus paper
10.5mL of hydro-chloric acid
11.30mL methylene chloride
12.250mL Erlenmeyer flask
13.Two 50mL Erlenmeyer flask
14.Hot water bath
15.Separatory funnel
16.Mel-Temp apparatus
17.Thermometer
18.Capillary tubes
Procedure: The first thing that was done was weighing out one gram of a
dimethoxybenzene/benzoic acid mixture, which was added to a small Erlenmeyer
flask, and about 45mL of dimethyl ether, which was cooled in an ice bath for
about 5-10 minutes. We then used the cooled dimethyl ether, in small amounts,
to dissolve the mixture and then transferred the mixture into a separatory funnel.
After using the rest of the cooled ether to rinse the Erlenmeyer flask we added
10mL of cooled 0.5 N sodium hydroxide solution to the separatory funnel and
shake the mixture in a back and forth manner. Once we were done shaking for
about fifteen to thirty seconds we drew off the aqueous phase into a 125mL
Erlenmeyer flask, and repeated the adding of the sodium hydroxide and releasing
the aqueous phase process two more times. To assure that all traces of the base
were gone, we extracted the ether layer with 10mL of cooled deionized water and
add it to the rest of the aqueous extracts in the Erlenmeyer flask. The ether layer
was then poured out from the top of the separatory funnel in to a 250mL
Erlenmeyer flask and dried by adding anhydrous sodium sulfate, swirling the
solution and stoppering the flask until ready for use later. We are now dealing
with the aqueous phase again by pouring it back into the separatory funnel along
with 5mL of cooled 3M hydro-chloric acid. To check the acidity of this solution we
used a litmus paper and the glass rod to make sure that the solution was acidic.
We then followed rh same procedure before to let off one of the phases through
the funnel by adding three 10mL portions of methylene chloride into a 250 mL
Erlenmeyer flask. One main thing that was different was what we used to dry the
substance, this time we used anhydrous magnesium sulfate, stoppered the flask
 Page |3
Myeeka Hammond
May 24,2017
Extraction
and set it aside with the other organic phase. While waiting for the hot bathe to
start boiling, we decanted the two organic phases into two separate 50mL
Erlenmeyer flasks. Then we added them to the hot bathe and we watched until all
the solution was evaporated and then we put the two flasks into a ice bath to cool
down and aid in the formation of the crystals. Once we obtained the crystals we
weighed them and used the Mel-temp apparatus to find the melting point of each
compound.
Data and observations: This lab was fun and cool to do. So, the very first thing
that was noticeable to my group members and I was the layer that formed when
we added the 10mL of 0.5 N of sodium hydroxide. This layer formed because the
compounds mixed and one layer, the lower layer, is denser than the other, the
bottom layer. Once the we shook to the funnel and started to let out the vapor
we realized that you not only hear when the vapor is released, but you can also
see the vapor go into the air. To me that vapor looked like a matrix movie when a
gun was shot it the show the bullet moving in slow-motion. Another time that this
layer formed was when we were washing the ether layer, which was the upper
layer, with deionized water. Unfortunately, while we were doing this part of the
experiment some of the solution spilled out of the funnel, which might be the
reason our percent recovery was lower than what is normally recovered. Our
percent revered for the benzoic acid was 25.7% and for p-Dimethoxybenzene we
recovered 1.5%. I believe that the extremely low recovery for the second
compound was due to the fact that when one of my partners was putting the
solution to heat in the hot bath he dropped it in the bath and some of the water
might have gotten into beaker and compromised the solution. Another
calculation that had to be made was the melting point of each compound. For
benzoic acid, we obtained a melting point range of 103.8-105C, which is low
compared to the literature values 122.41C. The only thing I can think of that
would affect the melting point for this compound is heating it too fast or it wasnt
packed tightly. For p-Dimethoxybenzene the melting point average was 49.8-
54.9C. Compared to the literature value, 54C, I think we got this one to be more
accurate. The only thing wrong is that it is not a sharp melting point which can
mean that the substance was not as pure as it needed to be to get a sharp melting
point.
 Page |4
Myeeka Hammond
May 24,2017
Extraction
Conclusion: If I was to say that I think we conquered the main concept of this lab,
I think I would be lying. Our percentage recovered was very low, and we were a
little confused on the procedure and had to constantly ask the professor for help
to further understand. But we did get enough of the compounds to get the
calculations that we needed. I think that the recovery was low because we lost
some of our solution while separating and it could also be because of the amount
of time we left the substances to dry for. The substance that was left drying for a
longer period of time recovered more of the pure compound than the one that
was drying for a lesser amount of time. One thing I think would help the lab go a
little more smoothly is a procedure that was a little easier to understand. That
was my biggest flaw with this experiment, some of the steps were more confusing
than others.
Post lab questions:
1. Why would ethyl alcohol not be a good solvent to use with water in an
extraction?
Ethyl alcohol would not be a good solvent because ethyl alcohol is soluble in
water.
2. How does the extraction procedure differ when the organic phase is (a)
less dense than water and (b) denser than water? What differences did
you observe between the two drying agents that you used in todays
extraction process?
If the organic phase is denser than water, then we collect the bottom phase
and aqueous phase will be on top. If the organic phase is less dense, we collect
the top phase and the aqueous phase is on the bottom. Magnesium sulfate is
fluffier than sodium sulfate and tends to remain suspended in solutions for
longer periods of time. Sodium sulfate, however, has the higher water
capacity.
3. What is the purpose of venting the separatory funnel by occasionally
opening the stopcock during the shaking process? Why is there a buildup
of pressure even when no gas is being produced by a chemical reaction?
 Page |5
Myeeka Hammond
May 24,2017
Extraction
The buildup of pressure will take place due to the formation of the ether of
organic solvent vapor produced by the heat of the hands. That is the reason
the separating funnel stopcock needs to be occasionally opened.
4. What is the biggest safety hazard in this experiment?
The biggest safety hazard in this experiment is evaporating any solvent into
the laboratory airspace shared by all.
5. Describe a procedure that might be used to separate p-dichlorobenzene
(a neutral compound) from p-chloroaniline ( a basic compound) by
extraction.
They can be separated by using hot water. When hot water is added into the
mixture, p-dichlorobenzene forms percipitate and settles down. It can thus be
skimmed and filtered. P-chloroaniline dissolved completely in water, thus can
be separated.
6. Why is it necessary to remove the stopper from the separatory funnel
when the liquid is being drained from it through the stopcock?
To release any possible buildup of pressure and to help the flow of liquid
through the small opening in the stopcock.