Isolation of Essential Oils from Cloves by Steam Distillation ***Record all raw measurements in your notebook, as well as all

observations and times. Goggles are required during the entire experiment! Ether is extremely flammable and must be handled carefully. Keep the ether closed except when it is necessary to have it open. Dispense and evaporate ether only in the hood. Steam distillation is a common technique for isolating essential oils from plants. Essential oils are mostly made up of terpenes and phenylpropanoids. Most essential oils contain multiple compounds, which is why gas chromatography-mass spectrometry (GC-MS) is the method of choice for analyzing complex oils. The gas chromatograph separates the individual compounds, which can then be analyzed by the mass spectrometer. Since eugenol is by far the major component of the essential oil of cloves, we can analyze it using infrared spectroscopy (IR), which would not be an ideal choice for most other essential oils. 1. Make sure you and your partner(s) are starting with a homogeneous plant sample. If you have whole seeds, you will need to crack them before weighing them using a mortar and pestle. Do not finely crush or grind your cloves! You want a lot of surface area but not a powder because powders can cause foaming that will complicate your distillation. 2. Describe your raw plant material in your notebook, including odor. Record all observations throughout the experiment in your notebook. 3. Each group member should transfer about 10 g of dried plant material into a 100-mL round bottom flask. Use a funnel to keep solids away from the neck of the flask so that it will seal properly. Do not use any grease. 4. Add 50 mL water. 5. Allow the cloves to soak while you assemble the apparatus shown below. You may go ahead and connect the water supply and turn it on gently. Do not turn on the heat until your instructor has a chance to make sure everything is set up correctly. Soak the cloves for at least 20 minutes. Record all actual start and stop times.
= Keck clamp
thermometer

distillation head

stopper jacketed condenser Claisen adapter 500 ml RBF heating mantle Erlenmeyer flask adapter

No Keck clamp here!!!

beaker with ice

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thermometer adapter

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6. After your instructor has checked your set-up, turn the heat on high until your solution just begins to simmer, and then turn the heat down to about half. Do not boil vigorously! If stuff from the flask being heated makes it into the condenser, then you will have to start over. Make sure you can read the thermometer between 95-105C. 7. After a few more minutes, a milky distillate should start dripping into the Erlenmeyer flask. As soon as you see this dripping, record the head temperature. If it does not drip within a few minutes of boiling, you can insulate the side-arm of the Claisen adapter with some glass wool. 8. Continue boiling until you collect about 15-20 mL of distillate. Try to maintain a drip rate of about one drop every three seconds by adjusting the heat as necessary. You may add water through the Claisen adapter if your water level gets low. Any cloudiness or oil drops you see in your distillate is normal. 9. Once you have collected about 30 mL of distillate, record the head temperature again. 10. Dissolve 0.5-1 g NaCl in your distillate. The added salt makes the water more polar and thus pushes the less polar essential oil compounds out of the aqueous layer. 11. Describe your distillate, including odor, in your notebook. 12. ***Swirl your Erlenmeyer flask and dump its contents into a separatory funnel. 13. Add 20 mL diethyl ether (CAUTION! FLAMMABLE!) to the Erlenmeyer flask, swirl to rinse the flask, and then dump this rinse into the separatory funnel. 14. Gently mix the two layers. Vent frequently so that pressure does not build up from the ether. 15. Put the separatory funnel on a ring stand and allow the layers to separate. The denser layer will be on the bottom. Water is denser than ether. 16. Label two containers as follows: aqueous, organic. Remove the stopper and then drain each layer into the appropriate container. 17. Put the aqueous layer back into the separatory funnel. 18. Repeat two more times with fresh ether (3 extractions total). You will collect all of the organic layers into the same container and you will reuse the aqueous container each time. 19. After you have performed the three separate extractions and have collected all three organic layers into a single container, dry (remove water) the organic solution with anhydrous sodium sulfate. Add as much as necessary to make your solution clear (not cloudy) and leave some of the sodium sulfate still somewhat granular (not completely clumpy). Do not ask your instructor how much you need. You need as much as you need and that will vary by person to person. There is no way to predetermine how much you need. If you are careful with your extractions and limit the water in your ether extracts, then you will not need much. 20. After removing water with the sodium sulfate, decant the rest of your organic solution into a beaker containing a Boileezer or boiling stick. 21. Evaporate the solvent gently in the hood until you have only about 5-15 mL of liquid left. 22. Label a 20 mL sample vial, add a Boileezer, and then weigh it. 23. Transfer your 5-15 mL remaining ether solution to this vial and then continue evaporating the ether. As soon as the ether stops boiling, immediately remove the vial from the heat. Do not overheat or you will lose some of your oil! 24. Let the vial cool, weigh it, and then cap it tightly. You will have only a tiny amount of oil. 25. Label all vials as LastnameFI-cloves-LabCode-Date. (e.g., BennettJ-cloves-M, 3/5/12 26. Then, by wafting, describe the odor of your oil. 27. All solids from this experiment should be discarded in the trash after filtering through a Buchner funnel. The liquids that you are not saving may go down the drain. Do not put any solids in the sinks or drains! Labs will be checked at the end and penalized for water leaking out of trashcans and solids in sinks. 28. Clean and return all borrowed glassware/equipment. 29. Turn in your notebook pages. 30. Turn in your vial of oil.