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MATERIALS Distilling flask (250ml) Erlenmeyer flask (250ml) Graduated cylinder (50ml) Separatory funnel (250ml) Test tubes Clamps Rubber tubing Adaptor Condenser Filtration funnel Watch glass Red litmus paper Ice bath Filter paper Iron ring Spatula

REAGENTS Ground cloves Distilled water Hexane NaOH (10% w/v) HCl (6.00 M) Anhydrous Na2SO4 NaCl 1% FeCl3

Bayer’s Reagent Table 1. List of materials and reagents used Part I: Distillation of Cloves A 5.00g sample of ground cloves weighed on an analytical balance was wrapped in a filter paper tied to a

string about 10 inches long, similar to a tea bag. The filter paper with ground cloves was immersed in a distilling flask with 75.0ml of distilled water. A distillation set-up was assembled as shown in Figure 1 below.

thermomet er

water out

clamp here

Iron clamp distilling flask w/ cloves

condense r adapte r water in Bunsen burner graduate d cylinder

Iron stand Figure 1. Distillation set-up

After turning on the water supply, the water was allowed to boil. 50.00 ml of distillate was collected from the steam distillation process. The temperature of the steam was noted every after 5.00ml of collected distillate.

Part II: Active Solvent Extraction and Characterization The collected 50.00 ml of distillate was transferred into a 250-ml Erlenmeyer flask to which 3.0g of NaCl was added to, and was swirled until dissolved. The distillate with NaCl was cooled in an ice bath before transferring in a 250-ml separatory funnel. 25.0 ml of Hexane was added in the separatory funnel. The funnel was shook with occasional venting in order to release pressure build-up. After 5 minutes of shaking, there were two layers formed. A set-up for the separation of layers was prepared and is shown in Figure 2 below. The bottom aqueous layer was discarded, having only the upper organic layer left inside the funnel. Separatory funnel iron ring

Figure 2. Separation set-up Afterwards, 25.0ml of 10% NaOH was added, repeating the same shaking and venting process for five minutes. This time, the bottom aqueous layer was separated to a 250-ml Erlenmeyer flask, discarding the upper organic layer. The aqueous layer was cooled in an ice bath and acidified using enough 6.00 M of HCl. The acidity was tested using a red litmus paper. The acidified aqueous layer was placed back in the separatory funnel. 25.0 ml of Hexane was added, repeating the same shaking and venting process for five minutes. The bottom aqueous layer was discarded, and the upper organic layer was transferred to a 250-ml Erlenmeyer flask. A small amount of anhydrous Na2SO4 was added to the obtained upper organic layer. The hexane extract was filtered.

RESULTS AND DISCUSSION The steam’s temperature was recorded every 5.00ml of distillate was obtained in the distillation process. After 50.0ml of collected distillate, the temperature every 5.00ml of collected distillate is summarized in Figure 3.

Temperature in °C

120 100 80 60 40 20 0 5 10 15 20 25 30 35 40 45 50

Volume of distillate collected Figure 3. The temperature of steam every 5.00ml of collected distillate in ml Figure 3 shows that after collecting 50.00ml of sample, the temperature remains constant at 98°C every 5.00mL
of collected distillate. The collected eugenol underwent two qualitative tests. In reaction to potassium permanganate, the eugenol was observed to have a purple discoloration and slowly turning into brown. This indicates the presence of an alkyne/double bond structure in the collected eugenol sample. (Jason)

FOLLOW-UP QUESTIONS AND APPLICATIONS 1. Draw the structures of eugenol, eugenol acetate, and caryopyllene and explain the basis of separation of eugenol from the other components in clove oil. Eugenol Eugenol acetate Caryopyllene

Figure 4. structures of eugenol, eugenol acetate and caryopyllene (Jeffers, J.)

2. What is the temperature of volatilization of eugenol? Is this higher or lower than the actual boiling point of eugenol and why? The temperature of volatilization of eugenol is almost but not higher than 100°C. The actual boiling point of eugenol is 254°C, making the temperature of volatilization much lower than its boiling point. Volitile compounds such as eugenol decompose at very high temperatures. Steam distillation avoids very high temperatures to distill eugenol at its temperature of volatilization, which is 98°C in this experiment. (Cebrian, p.19), (Jeffers, para. 3) 3. What are the biological and pharmacological properties of eugenol? Eugenol is used as an insect attractant, UV absorber, analgesic, biocide, and antiseptic. It is also used as a surgical dressing when mixed with zinc oxide. In dentistry, eugenol is used in making filling materials, dental cements, and sealers. (Primary info, n.d.) 4. Illustrate the reaction between eugenol and FeCl3. What is the implication of this reaction?

Figure 5. Reaction of Eugenol to Ferric chloride (FeCl3) The ferric chloride test is used to determine the presence of a phenol structure in a compound. Change in colorations such as turning blue, red, green, or purple shows that phenol is present. (Cebrian, p. 20) 5. Illustrate the reaction between eugenol and Bayer’s reagent. What is the implication of this reaction?

Figure 6. Reaction of Eugenol to Potassium permanganate (KMnO4) Bayer’s test using Bayer’s reagent or potassium permanganate (KMnO4) is used to test unsaturation or the presence of alkyne structures or double bonds. (Jason, 2007)


Cebrian, T. (2007). Isolating Clove Oil from Cloves Using Steam Distillation. Chemistry Lab Experiment Packet. Retrieved from University of California Santa Cruz website on December 8, 2012 in Jason. (2007). What is Baeyer’s test?. Message posted on October 22, 2007. Retrieved from University of Illinois Department of Physics website on December 8, 2012 in Jeffers, J. (n.d.). Isolation of Clove Oil from Cloves, a Natural Product Extraction. CHM220 Steam Distillation and Extraction Lab. The Modular Laboratory Program in Chemistry, Tech 722. Retrieved from Kalamazoo Valley Community College website on December 8, 2012 in Primary Info. (n.d.). Eugenol: Information @ a Glance. Retrieved from Primary Information Services website on December 8, 2012 in