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Isolating Clove Oil

from Cloves Using

Steam Distillation
Steam Distillation is a special type of distillation for temperature sensitive
materials like natural aromatic compounds.
-This distillation can be performed on two immiscible liquids so called
When two immiscible liquids are distilled, the total vapor pressure P
the liquid is equal to the sum of the vapor pressure of each compound. This
relationship is known as Daltons Law.
- P
is not dependent on mole fraction of each component which would be
included if the liquids were miscible, because the vaporization of each liquid
is independent of the other.
- Advantage : steam distillation allows distillation of organic compounds with
high boiling points to distill below 100 C avoiding decomposition.
Essential Oils
A volatile oil, usually having the characteristic odor or flavor of the plant, frequently
is a water-immiscible liquid separated by distillation from the plant material. Such
oils are used to make perfumes, flavorings, cosmetics, incenses, and medicine.
For example: Clove oil consists of several compounds such as
eugenol, which is the major component (85-90%) and eugenol
acetate (9-10%). Eugenol has a boiling temperature of 254 C.
Steam Distillation Set Up
stopper instead of thermometer
125 mL
fill with H
mark level
with marker
500 mL flask with boiling chip
Changes from the Lab Manual
1. Use 10 grams of powdered cloves rather than 5
grams of whole cloves.
2. Use 500 mL round bottom flask rather than a 100 mL
round bottom flask.
3. Collect distillate in a 125 mL Erlenmeyer flask.
4. Use a hot plate for your heat source
rather than a heating mantle.
5. Use ether to extract the distillate rather than methylene
Formation of big bubbles during
the distillation
Adding Cloves into the round bottom
flask using the stemless funnel
Clove Powder in the Flask
Experimental Procedure
Steam Distillation:
Don't forget to apply grease at every glass joint.
Distill at a steady rate (try distilling at 1 drop per 2 seconds).
Maintain water level by adding water from the addition funnel.
Distill until no oily layer is apparent. Collect at least 100 mL of
Transfer distillate to a separatory (sep) funnel and add 10 mL of
saturated NaCl solution to the sep funnel.
Rinse condenser and receiving flask each with 5 mL of ether and
transfer this to the separatory funnel.
Swirl gently and vent the sep funnel.
THEN vigorously shake with
frequent venting.

ether layer
aqueous layer
- Drain the aqueous layer. Transfer the ether layer (top layer) to a 50 mL
flask and return the aqueous layer (bottom layer) to the sep funnel.
- Rinse two more times with 5 mL portions of ether. With each step
combine the ether layers and repeat extraction of the aqueous
layer with the combined ether layers.
- Dry the combined ether extracts over anhydrous Na
for 5 minutes.
Decant as much as possible before removing balance with pipet.
- Filter ether solution through a cotton plugged pipet into a preweighed
50 mL round bottom flask
- Rinse the Na
with three additional 2-mL portions of ether and
filter into the preweighed 50 mL round bottom flask.
Simple Distillation:
- Remove ether by simple distillation. Place your receiver in an ice bath.
- Then remove last traces of ether with House Vacuum.
Simple Distillation
stopper instead of thermometer
flask in an
ice bath
50 mL flask with boiling chip
- Determine % recovery of eugenol. DO NOT dissolve eugenol in
Waste: - 1 bottle is in the hood for ether / water waste.
- DO NOT collect cloves! Decant water into sink, put cloves in
a paper towl and throw away in trash can.
- Next week, converting eugenol to the ester derivative
Omit : 1. TLC
2. The qualitative tests described in the module.
Don't forget: You will also weigh, perform TLC, and measure the melting point
for each of your compounds from last week. You need to submit your samples
in marked vials as instructed by your TA. You must turn in your TLC plates with
your lab report in an envelope.
Final Notes