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Addison Gasser Experiment 6

CHE 343-05

10/16/21

Isolation of Essential Oils Via Steam Distillation

The objective of this experiment was to isolate the essential oil cinnamaldehyde from cinnamon. This
was completed by first performing a microscale steam distillation, which is a separation technique used
for separating compounds that are insoluble, or slightly soluble, in water at all temperatures. Next, a
simple microscale extraction was performed to separate the essential oil from water. Finally, a liquid IR
spectroscopy was used to characterize the products.
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Data/Results
Mass of product:
Starting: 1.1188 g of cinnamon
Procedure
1. 1. Place 1.0-1.3 g of powdered cinnamon,
4-5 mL of distilled water, and a stir bar
into a 10.0 mL round bottom flask.
2. The steam distillation was set up. A reflux
condenser was attached to a
HickmanHinkle still, and the entire
apparatus was clamped in a sand bath. A
partial sheet of aluminum foil was used
to cover the bottom of the 10 mL round-
bottomed flask preventatively in order to
avoid overheating of the still head
3. Distillation: heat the sand bath to
approximately 150-160◦C and maintain
this temperature throughout distillation
using an external thermometer.
4. The co-distillate was removed with a 9”
Pasteur pipet as it was collected in the
still head well, and the pipet was used to
transfer the co-distillate into a centrifuge
tube. The distillation was continued in
this manner for approximately 40–60
minutes while it was made sure that the
temperature remained constant at about
150–160°C.
5. Isolation: Extract the distillate with 3
successive 2-3 mL portions of
dichloromethane.
6. All organic layers were combined in a
small E. flask and dried over anhydrous
sodium sulfate.
7. Using a Pasteur filter pipet, transfer the
dried solution into a small, tared filter
flask. To complete the transfer, add more
dichloromethane as a rinse.
8. Evaporate the solvent under vacuum
over a warm sand bath and obtain the
weight of the cinnamaldehyde product.
9. Obtain an IR spectrum of the sample.
Observations
Mass: 1.1550 g
The cinnamon was already in powder form
5 mL of distilled water was added
Stir bar added
Heat mantle was set at 180◦C then raised to 250◦C
After nothing was distilling, heat mantle was
raised up to 300 then 320◦C
Opaque, colorless distillate was constantly
collected in the well of the still head and
subsequently pipetted out into a centrifuge tube
every few minutes for about 90 minutes in total. It
took longer to reach a constant temperature due
to the cinnamon being a fine powder. The
temperature remained constant at 155°C the
entire time. All liquid portions were combined in a
single centrifuge tube.
Top layer: aqueous layer, cloudy white
Bottom layer: organic layer, clear, few cloudy
spots
The cloudy spots separated better after mixing
with a pipet
Anhydrous was added until clumping ceased
Filter flask: 38.4281 g
A small amount of dichloromethane was used to
rinse
Side arm flask was corked, and vacuum was
attached
Mass of filter flask after vacuum: 38.5912 g
Mass of sample: 0.1631 g
Peaks listed in results
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Final: 38.5912 g - 38.4281 g = 0.1631 g of cinnamaldehyde

Peak Value Functional Group

2967.3 cm-1 Aromatic C-H stretch
2854 cm-1 Fermi doublet
1675 cm-1 Carbonyl group
1261 cm-1 C-O stretching Bands
1015 cm-1 Trans disubstituted alkenes
~700 cm-1 Mono-substituted benzene ring

Set-Up Sketches

Discussion

This experiment demonstrates a

principle most are
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already familiar with and that is

that solids are more likely to
dissolve in a warm liquid than a
cold one. An impurity will not
dissolve when heat is applied,
and they can be removed from
the
hot solution through filtration.
Once impurities have been
removed the purified compound
can
begin to cool and reform the
bonds that it typically exhibits.
The purpose of this experiment was to learn and utilize techniques such as performing microscale steam
distillation as a separation procedure, executing microscale extraction based on simple solubility, and
running a liquid IR sample. Essential oils—either cinnamaldehyde from cinnamon or eugenol from cloves
—were separated in the steam distillation and then subsequently extracted from remaining water using
microscale extraction techniques. Finally, IR analysis was performed to obtain a spectrum from which
distinctive functional groups were then identified to confirm the identity of the essential oil product.
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Cinnamaldehyde has a very high boiling point (248°C), so steam distillation was necessary to distill the
compound from cinnamon in this experiment. Microscale steam distillation is a separation technique
that is commonly used for distilling oils, and other liquid compounds that are insoluble, or slightly
soluble, in water at all temperatures. It is used because these types of compounds are prone to
decomposing at high temperatures. This technique allowed the powdered cinnamon and water to ‘boil’
at a lower temperature due to the additive partial pressures of both substances. Once the water
vaporized, it ‘carried’ the cinnamaldehyde oils up into the still head of the apparatus to then be
collected. The oils, along with the water, were collected with a Pasteur pipet and put in a centrifuge
tube. There was such a low yield of cinnamaldehyde due to not all of it vaporizing along with the water
due to its higher boiling point.

The cinnamon was placed with deionized water and a stir bar into a 10 mL round-bottomed flask, and
the microscale steam distillation was set up properly. It was important that the steam distillation setup
included a Hickman-Hinkle still and reflux condenser so that the essential oil distillate could be collected.
The round-bottomed flask was placed in a sand bath that was heated to approximately 150–160°C
according to the external thermometer, but the actual distillation temperature of the round-bottomed
flask itself was approximately 100°C because it was being heated indirectly rather than directly. Every
few minutes, the constantly forming well of co-distillate was pipetted out of the setup and placed into a
centrifuge tube. This process continued for approximately 90 minutes. This took longer than the
anticipated 40-60 minutes because not nearly enough co-distillate had formed and been collected once
60 minutes had passed. This was due to the cinnamon being a fine powder, it took a larger amount of
time to heat up as it required a more gradual temperature increase.

The IR spectrum was used to identify the functional groups in each compound which confirmed the
identity of the oil. For cinnamaldehyde, an aromatic C-H stretch was noted at 2967.3 cm-1, a fermi
doublet was noted 2854 cm-1, and a carbonyl group was noted at 1675 cm-1. A C-O stretch of bonds at
1261 cm-1, a trans disubstituted alkenes at 1015 cm-1, and a monosubstituted benzene ring at
approximately 700 cm-1 was identified.

POST-LAB QUESTIONS

1. Regardless to whether a student isolated eugenol or cinnamaldehyde, there is often evidence of

a large O-H stretch on the IR spectra. This stretch would indicate an OH functional group that
was present in the oil or could indicate aqueous impurities. The misleading appearance of an O–
H stretch in cinnamaldehyde is most likely due to a remaining water presence in the compound.
The essential oil was probably not fully dried with vacuum filtration, or potentially not enough
drying agent was added. Since the essential oil was extracted from a water containing mixture, it
is highly likely that there was still some water remaining in with the compound that was not
pulled out before the IR spectra was run.