Burhan Riaz

02/12/2011

CHM 2211L-0017

Extracting Eugenol from Cloves

Introduction: In this experiment, eugenol is extracted from cloves. Some techniques and skills that are

used in this experiment are gravity filtration, steam distillation, extraction, using drying agents, using a

rotary evaporator, and using an IR apparatus to obtain a spectrum. Eugenol is used as a dental

anesthetic. There are no notable safety hazards. The following is the structure of eugenol:

Results and Discussion:

The following is the IR for the final product:

Absorbance (cm-1) Shape Intensity Group-Motion

3505 Sharp Strong O-H Stretch (Alcohol)

2948 Sharp Strong C=C Stretch (Alkene)

Calculations:

The final product after the rotary evaporator came to 90.9g. This gives a percent recovery of almost

68%.Purity of the product was kept intact throughout the procedure. After the use of the CaSO4 as a

drying agent, fluted paper was used to keep out the CaSO4 after it had been used. During the actual

extraction of eugenol, a seperatory funnel was used so the waste product would not corrupt the results

in the IR.

Experimental:

First assemble a steam distillation apparatus attached to a 500 mL round bottom flask. Add 15g of cloves

and 150mL of H2O into the round bottom flask. Heat at 100C and add water if there is not enough

throughout the procedure. Stop until 100mL of the azeotrope is collected. The remaining cloves can be

thrown away. Using a seperatory funnel, add the 100mL distillate and 15mL of Ch2Cl2 and collect the

bottom layer. Repeat this procedure 2 more times until 45 mL of the crude product is collected. To dry

and purify eugenol add the 45mL extract and .5g CaSO4 into a small flask. Pour the contents into a

100mL round bottom flask using fluted paper to dispose the CaSO4. Assemble the rotary evaporator and

let the solution evaporate until there is only the purified crude product. Calculate the % recovery and

run an IR on the sample.

Source: Xanedu Coursepack CHM 2211 UCF Spring 2011

Questions 1,2,3,4,5

1. Why should the K salts of fatty acids yield soft soaps? because they are more soluble in water than

sodium salts of fatty acids (which yield hard soaps). They contain more water, so they are softer.

2. Why is the soap derived from coconut oil so soluble? The primary fatty acid of coconut oil is laureate,

a 12 carbon chain. After Saponification there is a relatively high ratio of glycerin to oil and the fatty acid

salts are more soluble than would be with longer chain fats.**

3. Why does adding a salt solution cause soap to precipitate?

It can form an insoluble compound that will precipitate with a soap molecule that is known as soap

scum.**

4. Why do you use a mixture of ethanol and water rather than simply water in the saponification

reaction? Because the ethanol allows the oil to mix with the solution better. Water and

oil do not mix, however, if you add ethanol to the mixture it will mix with the

oil to form a solution.

5. Sodium acetate and sodium propionate are poor soaps. Why? Because they do not have a long

enough hydrocarbon side to bind to dirt. Therefore there is not enough non polar substance in the

molecule to bind to nonpolar dirts, fats and oils. **

Literature Article "Soaps and Detergents"

Chemistry 49 (Sept. 1976) : 6

1. What was the title of this article?

Detergents, soaps and syndets

2. Who was the author?

Clifton E. Meloan

3. What chemical company first discovered floating soap by accident?

Proctor and Gamble

4. What caused the soap to float?

Extra boiling whipped air into the soap; rapid cooling trapped the air there.

5. In order to function, as a detergent, what property must a substance have?

Must reduce surface tension 72 to 30 dynes per cm^2

6. Approximately what % of soap is needed to form an effective detergent?

8-18%

7. Name one cationic detergent mentioned in this article:

Octadecyl ammonium chloride

8. Why are emulsifiers added to detergents?

To prevent dirt particles from redepositting on a fiber.

9. Why is sodium silicate added to detergents?

Helps prevent corrosion.

10. Why are enzymes added to detergents?

To hasten breakdown of protein and large molecules.