Isolation Of Eugenol

Introduction

In this experiment, the essential oil eugenol (the main component of oil of cloves) will be isolated from whole cloves using the technique of simple distillation, which is often used to isolate liquid natural products from plants. The mixture of whole cloves and distilled water will then be heated to boiling and the distillate (a eugenol/water mixture) will be collected. The eugenol will then be separated from the water by extraction with pentane. The pentane solutions will then be dried over magnesium sulfate, remove the magnesium sulfate by vacuum filtration and remove the pentane from the filtrate by evaporation on a water bath in the hood. The percent recovery from cloves will be determined and the product will be analyzed by transmission infrared spectroscopy (IR).

Oil of cloves, which consists almost entirely of eugenol and its acetate, is used in perfumeries, flavorings, essential oils and in medicine (local antiseptic and analgesic).

Reaction: See flow chart attached

Data and observation

Substance Amount isolated (g.) Percent recovery (%) Observations

Eugenol 0.712 7.12 Large droplet of yellow oil with an aromatic spicy odor.

Acetyleugenol 0.528 5.28 Clear to pale yellow oily liquid with aromatic spicy odor.

Calculations

Percent recovery of eugenol

Amt. Eugenol isolated 0.712 g

% Recovery = ------------------------------ = -------------- x 100 = 7.12 %

Amt. Cloves used 10 g

IR spectrograph: See IR graph attached

Conclusion

Simple distillation of whole cloves produced 0.712 g of a yellow oil with spicy aromatic odor, which contained in its IR spectrum the functional groups O-H (at 3453 cm-1), sp2 C-H (3009 cm-1), C=C-H (2980 cm-1), and alkene C=C (at 1600 cm-1) and aromatic C=C (at 1520 cm-1). These data are consistent with the structure of eugenol. In addition, the IR of the product from the simple distillation of cloves