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Myeeka Hammond
June 7,2017
Isolation of Eugenol from Cloves by Distillation

Purpose: The purpose of the experiment is to use distillation to extract an essential oil, specifically

Eugenol oil, from a plant, the clove.

Introduction:

Essential oils are components of various compounds and are associated with scents and

medicinal purposes. Essential oils can be found in cloves, between 14% and 20% by weight and its

primary essential oil being eugenol, C10H1202. Eugenol, molecular formula shown in figure 1, has been

known to serve as a food flavoring additive and a dental anesthetic. Most oils are found to have long

hydrocarbons. Essential oils, however, are complex mixtures of fluids with a low viscosity that also

contains a variety of molecular species and functional chemistry groups. Cloves are the flower buds from

a tropical tree that grows in the Spice Islands of Indonesia and the islands of the Indian Ocean. In this

experiment, Steam distillation is used to extract essential oils, eugenol, from crushed cloves. Steam

distillation is utilized because of the oils high boiling points, which makes it difficult to extract

completely. When using steam distillation. The spice or herb is suspended in water, and as the water is

boiled and vaporizes, it extracts the essential oils and carries them over into the graduated cylinder. The

boiling point of eugenol is 225C but it is insoluble in water so it will steam distill at a temperature

slightly lower than the boiling point of the water.

Figure 1: Eugenol Chemical Structure

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Myeeka Hammond
June 7,2017
Isolation of Eugenol from Cloves by Distillation

Materials:

1. 2 Grams of cloves
2. 50 mL round bottom flask
3. 3 boiling chips
4. Heating mantel
5. Simple Distillation Apparatus
6. 25 ml graduated cylinder
7. 5 ml of Dichloromethane (CH2Cl2)
8. Anhydrous Magnesium sulfate (MgSO4)
9. Seperatory funnel
10. 2 Watch glass
11. 3 clips
12. IR spectrum Machine

Procedure: The experimenters obtained 2 grams of cloves, that were pre-grinded, and added them into

a 50-mL round bottom flask and added three boiling chips along with 25-mL of water. The solution was

then swirled the flask, which aided in wetting the cloves, and then left the flask to sit for about 10

minutes before beginning the distillation. While waiting for the ten minutes, the experimenters set up

the simple distillation apparatus and greased all the parts that were attached to ensure that it was

sealed. They then used the heating mantel to heat the flask to a boil and the vapor will start to distill

over the collection vessel. The distillation was continued for about 45 minutes or until 12-15 mL of the

condensation in the graduated cylinder was collected. After the distillation was completed, the

experimenters allowed it to cool to room temperature. Once it was cooled, the experimenters extracted

the eugenol from water using dichloromethane in a speratory funnel. This was done by adding 5mL of

the dichloromethane, shaking the funnel to mix the layers and then it was separated by opening the

cockstop to remove the lower layer, which is the CH2Cl2. The experimenters then repeated this

separation process again and then dried the CH2Cl2with about one gram of anhydrous Magnesium
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Myeeka Hammond
June 7,2017
Isolation of Eugenol from Cloves by Distillation

Sulfate. After it was transferred, the dried dichloromethane solution onto two tared watch glasses, then

rinsed it a little with CH2Cl2 and then allowed it to evaporate in the fume hood to isolate the eugenol oil.

Once the oil was obtained, it was weighed to get the mass and then found the IR spectrum using the IR

machine.

Calculation:

Percent yield = Grams of Eugenol/ Grams of clovers used X 100

Data and Observations: The calculated percent yield of 0.00% is relatively low. A possible explanation

for this low yield may have arose from an inadequate amount of dichloromethane during the extraction

method. The dichloromethane would help spate the eugenol and the water. Eugenol is more soluble in

dichloromethane than in water, and it would be found in the organic layer with dichloromethane. Other

than the low percent yield, the experiment proceeded as planned. There were no spills or other

abnormal physical losses. Some observations that my group members and I observed through-out the

experiment is that right before the solution in the round bottom flask started boiling all the cloves

started to club together and settle at the bottom of the flask. One thing was really cool to me was that

you could see the distillate running through the condenser, most likely because it is not the same color

as the water in there, and out in the graduated cylinder. The color of the distillate was a cloudy white

solution that eventually resulted in the eugenol oil.

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Myeeka Hammond
June 7,2017
Isolation of Eugenol from Cloves by Distillation

Conclusion: The result of this experiment showed that 0.00% of oil could be recovered from cloves by

steam distillation. The takeaway from this lab experiment was to learn the techniques of isolation of

natural products, which included steam distillation, drying organic solution, and liquid/liquid extraction.

It is possible that the ratio of the size of the glassware to the theoretical amount of eugenol (which was

obtained from the cloves in this experiment) is large which lead to a large percentage of the product on

the sides of the glass apparatus. If this is the case of our low percent yield, then further experiments

should include a larger sample of cloves for better/ improved recovery. Otherwise, it can be concluded,

from this specific experiment, that the specific sample of cloves used contains approximately 0.00% of

eugenol.

Post lab questions:

1. Calculate the percent (by mass) of eugenol in cloves based on your data. Eugenol typically

makes up about 15-20% of the mass of clove buds. Discuss reasons why you may not have

isolated this amount, and propose ways to increase your yield.

2. Examine the IR spectrum of eugenol, and identify the signals for the major functional groups.

3. A representative of 1H NMR spectrum of eugenol is shown below. Assign the signals to the

correct protons in the structure.

4. Eugenol can also be isolated from cloves using extraction with CO2. Discuss the advantages

and disadvantages of distillation verses CO2 extraction.

Distillation is more advantageous than carbon dioxide extraction because a larger product yield is

extracted. However, it takes time. Carbon dioxide extraction is also disadvantageous because the

pressure that builds up from sublimation can cause the cap on the test tube to come off.