Part 3 Experiments

87
 Experiment 1 SIMPLE DISTILLATION

In this experiment, you will perform a distillation of a mixture of two liquids and measure the temperature
change, without actually separating the two liquids. The purpose of this technique experiment is: 1) to
observe the distillation behavior of a homogeneous liquid mixture, and 2) to develop the basic distillation
skill often used in organic synthesis.

Background Reading
Read Chapter 6 about the distillation technique. Also review heating mantle in section 3.3.

Webpage Demonstration
A PowerPoint demonstration about the distillation setup is available on the organic laboratory course
website: http://www.sinc.sunysb.edu/Class/orgolab/che327383384ppts.htm, and on Blackboard as well.
You may wish to print this out (six frames to a page is convenient) for reference during the lab period.

Properties of New Materials

Name Appearance Boiling Point (oC) Hazard Statements

95% Ethanol Colorless liquid 78 Flammable

Skin and eye irritation

Water Colorless liquid 100 -------------

Safety Precautions
If you break a thermometer, inform the lab staff so they can deal with the broken glass, and
mercury hazard (if any). Do not attempt cleanup yourself.
Never plug the heating mantle into the wall socket.
Never distill to dryness.

Pre-Lab Study Questions

Always ask yourself what is the purpose of each step in the procedure. In addition, consider the following
for this experiment.
1. What is a liquids boiling point? What is normal boiling point?
2. How is a compounds boiling point affected by its molecular structure?
3. Why should a distilling flask be at least about one-third full but no more than half full?
4. What would be the effect on temperature measurement of a thermometer that was positioned too
high? Too low? Explain.
5. Why is it dangerous to heat a closed system containing volatiles?

88
Experimental Procedures
Part A Apparatus Assembly for Simple Distillation
Step in procedure
1) Set up a distillation as shown in Figure
E1.1 and also on the webpage.
a) In a 100 ml round bottom flask (rbf),
put 20 mL 95% ethanol, 20 mL tap
water, and a boiling stone.
b) Clamp the rbf (the pot) containing
the ethanol-water mixture to a ring
stand at a height of about 10 cm from
the base.
c) Support a 100 mL heating mantle on
a ring and fit the mantle as snugly as
possible to the flask.
d) Plug the heating mantle into a
Variac; the switch should be in the
off position.
e) Lightly grease the ground glass joint
that will be connected.
f) Insert the thermometer into its cap,
and then slip on the o-ring below the
cap.
g) Connect the thermometer and cap to
the distillation apparatus; connect the
assembly to the rbf; adjust the
thermometer position.
Comments
If you break a thermometer, inform your TAs so
they can deal with the broken glass and mercury
hazard. Do not attempt cleanup yourself.
Generally a distilling flask should be at least about
one-third full but no more than half full.
Having a boiling stone will prevent the liquid from
violent distillation (also called bumping).
It is necessary to clamp at the neck of any flask that
is heated. Support of the flask allows quick
removal of the heat source should the reaction
begin to go out of control.
Any space between the sides of the rbf and the
heating mantle can be filled with an aluminum foil
collar. Never place foil underneath the rbf you
could start a fire.
With the Variac, you will be able to control the
voltage, and thus the range of heating and the
maximum temperature attainable. Never plug the
heating mantle into the wall socket you could
start a fire.
Greasing will allow for later ease of disassembly.
Be moderate. Remember that too much grease will
dissolve in the product and contaminate it.
Be sure to place the o-ring in the proper position so
that a seal is created.
In distillation, you will be sure to get an accurate
boiling point only if the top of the thermometer
bulb is level with the bottom of the side arm, as
shown by the dotted line in Figure E1.1.
To ensure that the thermometer does not touch the
inside glass wall of the apparatus, you may need to
support the upper stem against a clamp on the ring
stand.
89
 h) Place a 50 mL graduated cylinder
below the drip tip of the distillation
apparatus.
i) Connect hoses to the condenser, and
connect the bottom one to the faucet.
j) Turn on the water faucet and adjust
the flow to a gentle stream.
top of bulb level with
bottom of side arm
clamp here
Figure E1.1 The setup for the Simple Distillation experiment.
90
If the first graduation on your cylinder is above 2
mL, you will need to fill the cylinder with water up
to a convenient graduation. Make sure to record
the start volume so that you can keep track of the
actual volume of distillate that will be collected.
Use the clear thin-walled hosing instead of the red
thick-walled hosing. The first is more flexible and
less likely to be forced off by high water pressure.
Too high a water pressure can force the hoses off in
the next step, causing a flood.
Rest thermometer
on a clamp here.
water out
water in
Be sure to plug the heating
mantle into the Variac.
Part B Simple Distillation of an Ethanol-Water Mixture
Step in procedure
1) To begin distillation, turn on the
Variac and adjust the setting.
2) Observe the rise of the vapor head
(the liquid-vapor line) and adjust the
thermometer if necessary.
3) Adjust the rate of distillation to
reach a moderate, steady distillation
rate.
4) Collect the distillate in the 50 mL
graduated cylinder.
5) Stop distilling when you have
collected at least 26 mL of distillate
or if there is a small amount of
liquid remaining in the pot.
6) On the due date, submit to your TA
the completed report form (p. 93).
[Consult the End-of-Lab Checklist on the next page for storing product and discarding residues.]
Comments
The Variac setting depends on the boiling temperature of
the liquid. You should try a low setting (about 50-60 V
or 15-20%, depending on the type of Variac being used)
initially since ethanol has a relatively low boiling point.
As the liquid begins to boil, the vapor head will rise until
it reaches the bottom of the side arm (the position shown
by the dotted line in Figure E1.1). If you have placed
your thermometer correctly, the bulb will be completely
bathed by liquid and vapor in equilibrium.
A relatively slower dripping rate (1 drop about every 4
or 5 seconds) is recommended here so that you can
accurately measure Thead and receive better results.
To adjust the rate, you may need to raise or lower the
Variac setting. If necessary, you may insulate the rbf
and distillation head against lab drafts. A tent of
aluminum foil is good for this purpose, but be sure the
foil does not touch the glass. Leave open a small flap so
that you can view the liquid remaining in the pot. Save
the foil at the end.
In a table in your notebook, at intervals of 2 mL, record
the volume of the distillate and the corresponding
boiling temperature measured on the thermometer head
(Thead). If you added water to your cylinder before
distillation, make the necessary adjustments.
NEVER distil to dryness rapid decomposition of
high-boiling impurities could start a fire or explosion.
When most of the liquid has been distilled, the
temperature may drop somewhat, due to insufficient
volatile material remaining to bathe the thermometer.
Consult the End-of-Lab Checklist on the next page for
discarding residues.
At the end of the lab period, be sure to submit all carbon
copies, even if you have a notebook page only partially
completed. Continue on a fresh page next time.
91
End-of-Lab Checklist

Save Discard

Keep any foil that you used for insulation. Discard the liquid samples into the LIQUID
WASTE container

92
 CHE 327 SIMPLE DISTILLATION RESULT FORM 2014-2015

Students name_______________________________ TAs name_______________________

Grade__________

On this and all reports, keep your answers succinct (20-30 words). Excessively wordy answers that
do not express the ideas clearly will not receive full credit.

1. Fill in the table below based on your data collected during the Simple Distillation experiment.

Volume of Distillate ( mL) 2 4 6 8 10 12 14

Thead (oC)
(continued)
Volume of Distillate ( mL) 16 18 20 22 24 26 28
o
Thead ( C)

2. a) In the space below, plot your data with the volume of distillate as the horizontal axis and head
temperature (Thead) as the vertical axis. Draw a smooth curve through the points plotted.

b) Clearly indicate the following by placing the corresponding letter on the distillation curve above
and use brackets to specify where each fraction begins and ends:
A. Fraction of the distillate composed mostly of ethanol.
B. Fraction of the distillate composed mostly of water.
C. Fraction of the distillate containing a mixture of ethanol and water.

c) As you know from your reading in Chapter 6, the simple distillation technique can be used to
separate liquids in a mixture by changing collecting flasks at the appropriate time. Based on your
distillation curve above, describe what you would do to get at least partial separation of ethanol and
water if you performed the experiment again.

93
94