Experiment 21

Extraction of Caffeine from "Cola" Drink

Goals:
1. 2. 3.

Learn to use the separatory funnel. Learn the principles of liquid-liquid extraction. Learn to use melting point equipment to test the purity of the extracted product. Concept: Caffeine is the compound that is responsible for the stimulating action of coffee and tea. It is also present in chocolate, cocoa, colas and "stay awake-pills" It is an example of an alkaloid; a group of organic compounds containing nitrogen. They are produced by plants and have physiological actions. Chemically, they are weak organic bases. (Reference: Chapter 6: Amines and Amides) Materials: "Decarbonated Cola Drink" , CH2Cl2 (methylene chloride), anhydrous Na2SO4, boiling chips, hot plate, 125 mL-separatory funnel with stopper, 150 mL beakers, 150 mL Erlenmeyer flask, iron stand, iron ring, and clay triangle, melting point apparatus, melting point capillary tubes Procedure: 1. Transfer 60 mL of "Decarbonated Cola" into a 125-mL separatory funnel supported by an iron ring on the ring stand. Carefully, add 5.0 mL of methylene chloride (CH2Cl2) to the "Cola" in the separatory funnel and insert the stopper. (INSTRUCTOR, please show how to use the separatory funnel). Invert the flask and immediately open the stopcock to release the pressure inside the flask making sure the opening is NOT pointing towards you or your neighbor. Close the stopcock, and mix the contents of the flask by inverting gently. Do this procedure two or three times, each time opening the stopcock to release the pressure that builds up inside the flask. 2. Return the separatory funnel to the ring stand, remove the stopper and let stand to allow the aqueous layer (top layer) to separate from the methylene -caffeine layer (bottom layer). If an emulsion is formed, gently stir the emulsion using a glass rod.
3.

Drain the lower (methylene chloride) layer into a 125-mL erlenmeyer flask. Be careful not to include any water. Add 5.0 mL of methylene chloride (twice) to the aqueous layer in the separatory funnel and repeat steps 1 and 2. Combine the methylene-caffeine extracts.

4.

Add 0.5 g of anhydrous Na2SO 4 to the combined methylene-caffeine extract. Swirl the flask. Sodium sulfate, Na2SO4 (drying agent) will remove excess water that may still be present in the methylene-caffeine extract. Weigh a 150 mL beaker containing two or three boiling chips. Record this weight. Decant the methylene-caffeine extract into the pre-weighed beaker. Add about 2 mL of methylene chloride to the Na2SO4 to rinse and decant to the pre-weighed beaker. Evaporate the methylene chloride in the hood using very low heat (hot plate, setting 1 or 2). Be careful since the solvent may foam over. The solid that remains when the solvent (methylene chloride) is completely evaporated is the crude caffeine. Weigh the extracted caffeine during the next laboratory session. Show your product to your instructor. Calculate the mg (milligram) of caffeine in the 60 mL sample cola. Determine the melting point of your caffeine.____________oC

5.

6.

7. 8.

Report sheet: Weight of a 150 mL beaker with boiling stones g Weight of a 150 mL beaker with boiling stones and crude caffeine g Weight of caffeine (mg) in 60 mL sample mg 4. Calculate milligrams of caffeine/serving (1serving = 8 oz. drink). Show calculations.

Questions: 1. Why is the melting point of your extracted caffeine lower/higher than the literature value? What could be some possible causes of error? How could you improve the purity of your extracted caffeine?

2.

Why is it necessary to "decarbonate" the cola before extracting the caffeine?

3. Why is caffeine more soluble in methylene chloride (CH2Cl2), an organic solvent, than in water?

4.

Give 5 other examples of alkaloids and list their uses. (Ch.6 in your text book)