Title: Steam Distillation: The isolation of eugenol from cloves.

Objective: To isolate a natural product from cloves by performing steam distillation using
microscale distillation apparatus.

Materials needed:

Ground cloves, graduated cylinder, deionized water, 25- mL round bottom flask, magnetic spin
bar, microscale distillation apparatus ( Flask, hickman still head, water condenser), sand bath,
heating mantle, thermometer, aluminum foil, 15 mL screw cap centrifuge tube, separatory funnel,
erlenmeyer flask and spatula.

Chemicals Needed:

Sodium sulfate, anhydrous sodium sulfate, and 2mL Ch₂Cl₂.

Procedure:

1. Using a graduated cylinder measure 15 mL deionized water and add 1 g of crushed cloves into
a 25 mL microdistillation set.

2. Place a magnetic stirring bar and start distillation at a temperature of 85-90˚C.

3. Continue distillation until 5-8 mL of the distillate has been collected, and place in a
Erlenmeyer flask.

4. Add sodium sulfate to the solution till it becomes saturated.

5. Added 2.0 – 3.0 mL CH2Cl2 and mixed the solution

5. Transfer to a separatory funnel and drain off the lower layer.

6. Transferred the upper organic layer into a conical bottom Erlenmeyer flask, and added 1 drop

of NaOH and 1 drop of phenolphthalein, if it turns pink it is a positive result.

7. Added 2-3 drops of acetic acid, if it gives off a fruity smell, it is a positive result.

Data and Results

Observations Result after addition of chemicals

Distillation: white milky color

Separatory funnel:

Upper layer: clear

Bottom layer: Milky white

Addition of 1 drop of NaOH + 1 drop of Pink color.

phenolphtalein

Addition of 2-3 drops of acetic acid Clear solution and fruity smell.

Discussion:

In this experimented we isolated eugenol from cloves, which is a natural chemical found in
cloves. Eugenol is a phenylpropene, and belongs to phenylpropanoids class of chemical
compounds. In appearance, eugenol is a colourless to pale yellow aromatic liquid, and is
commonly used in perfumes, flavorings and essential oils.

Boiling point of eugenol is 248˚C, and can be obtained at a lower temperature by performing
steam distillation. In steam distillation the total vapor pressure of the heterogeneous mixture is
the sum of the vapor pressures of the individual components; which leads to a higher vapor
pressure for the mixture, which leads to a lower boiling point for the mixture ( Raoults law).
Steam distillation can be carried out in two ways; direct and live steam method. In direct, the
steam is generated by boiling a mixture of the copound of interest and water, where live method
is where steam is used from an external source. This experiment involved using direct steam
distillation.

Conclusion:

In conclusion my lab partner and I successfully isolated eugenol from clove using steam
distillation. Our results were obtained by heating a mixture of 15 mL of distilled water and 1.02 g
of cloves at a temperature of 90˚C. Once the distillate was collected, sodium sulfate was added as
a drying agent until the mixture was saturated. Ch₂Cl₂ was then added to separate organic layer
from aqueous layer. The solution was then separated from organic layer and aqueous layer by
using a separatory funnel. After draining of the lower layer, the upper layer was obtained in a
Erlenmeyer flask and NaOH was added for the removal of remaining water and tested with
phenolphthalein, which gave a pink solution. 3 drops of acetic acid were also added to the
mixture which turned the solution back to a clear solution and gave off a fruity smell.