EXPERIMENT 8 PROCEDURE CH226 (2)

Experiment 8 CH226: Isolation of Eugenol from Cloves
Objective
To isolate clove oil from cloves by steam distillation and extraction.
Introduction
Simple and fractional distillations are carried out on miscible mixtures. Distillation can
also be performed on mixtures in which the two compounds are not miscible. This process is
called co‐distillation. When one of the compounds is water, the process is called steam
distillation.
Steam distillation offers an advantage in that volatile compounds that are unstable or
have high boiling points can co‐distill with water at relatively low temperatures. This process
avoids decomposition that might occur at the normal boiling point of the compound of interest.
For example, eugenol, the major compound of clove oil, boils at a relatively high temperature of
254 °C. Steam distillation avoids this high temperature and results in the distillation of eugenol
at a temperature slightly less than 100 °C.
In practice, steam distillation is usually carried out by one of two methods. In the first
method, an excess amount of water is added to the compound of interest in a distilling flask. The
mixture is then heated to the boiling point. The resulting vapor is condensed and collected in a
receiving flask. The compound of interest is then separated from water, often by extraction. In
the second method, steam is bubbled into the compound of interest to effect the distillation. In
this experiment, the first method will be used because it is easier to set up.
Clove oil belongs to a large class of natural products called the essential oils. Many of
these compounds are used as flavorings and perfumes and, in the past, were considered to be the
“essence” of the plant from which they were derived. Cloves are the dried flower buds of the
clove tree, Eugenia caryophyllata, found in India and other locations in the Far East. Steam
distillation of cloves results in clove oil, which consists of several compounds. Eugenol is the
major compound, comprising 85‐90 %. Eugenol acetate comprises 9‐10 %.
In this experiment, you will steam distill clove oil from freshly ground cloves. Following
the distillation, clove oil and water will be present in the receiving flask. Because clove oil will
be a minor fraction of the distillate, the clove oil must be extracted from the water into an
organic solvent such as dichloromethane. Removing dichloromethane leaves clove oil as the
product.
Experimental Procedure
Part A: Isolation of Clove Oil
1) Weigh 5 g of dry ground cloves.
2) Transfer the ground cloves to a round‐bottom flask. Add 50 mL of distilled water and a few
boiling chips.
3) Assemble the distillation apparatus (see figure). You can use a graduated cylinder or
Erlenmeyer flask as the receiver. Start the flow of water through the condenser.
4) Ask your instructor to inspect your equipment set up. Turn on the heating mantle. When the
mixture boils, adjust the heat to maintain a distillation rate of approximately 1 drop per second.
5) Stop the distillation when approximately 30‐40 mL of distillate has been collected.
6) Allow the distillate to cool to room temperature. Carefully pour the distillate into a separatory
funnel. Add 10 mL of saturated NaCl solution.
7) Rinse the inside of the condenser and the receiver with 5‐10 mL of CH2Cl2 into the
separatory funnel.
8) Cap the separatory funnel and gently swirl the contents for several seconds. Vent the
separatory funnel frequently. After the pressure has been vented, shake the contents vigorously
to thoroughly mix the two layers.
9) Allow the layers to separate. Drain the CH2Cl2 layer into an Erlenmeyer flask.
10) Repeat the extraction of the aqueous layer twice, each time with 5 mL portion of CH2Cl2.
Combine organic layers in the same Erlenmeyer flask.
11) Dry the combined CH2Cl2 solution with anhydrous Na2SO4.
12) Decant the CH2Cl2 solution into a pre‐weighed beaker, making certain that no Na2SO4 is
transferred with the solution.
13) Place the beaker on a hot water bath to remove CH2Cl2.
14) When all of the CH2Cl2 has been evaporated, allow the beaker to cool to room temperature.
Weigh it to the nearest 0.001 g and record the weight. Subtract the mass of the empty beaker to
obtain the mass of the clove oil.
15) Report the weight and percent yield of clove oil on your worksheet.
16) Using silica gel TLC plates, run a TLC plate of the clove oil that you have isolated. Use a 1:2
mixture of dichloromethane-pentane to run your TLC plate. Can you tell which spot corresponds
to eugenol and which one is eugenol acetate?

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EXPERIMENT 8 PROCEDURE CH226 (2)

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Experiment 8 CH226: Isolation of Eugenol from Cloves

To isolate clove oil from cloves by steam distillation and extraction.

Part A: Isolation of Clove Oil

1) Weigh 5 g of dry ground cloves.

11) Dry the combined CH2Cl2 solution with anhydrous Na2SO4.

13) Place the beaker on a hot water bath to remove CH2Cl2.

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