Extraction of caffeine from coffee or tea 1) Take a 2-neck-round-bottom flask and put a cooler in the central neck; 2) Put

in the flask 35 g of ground coffee or 10 tea bags (please take off the paper covers), 12 g of Na2CO3 and 200 mL of distilled water. Close the side neck with a stopper and, while stirring, bring the mixture to reflux, keeping it for about 20 minutes. (Na2CO3 is added in order to make caffeine present as the free base.) 3) Filter the mixture over a Bchner funnel, wait until the liquid phase cools down to room temperature and put it into a 500 mL extraction funnel; 4) Add 50 mL of CH2Cl2 to the funnel and start the extraction. NOTE: do not shake the funnel vigorously othewise an emulsion difficult to break can form; just put it upsidedown and swirl it gently with a rotatory motion for 5 minutes, opening the stopcock at regular intervals. 5) Leave the funnel on the support until the two phases separate (Despite of the taken precautions, the organic phase can be anyways emulsioned. Dont worry and go on). 6) Separate the organic phase, extract the water phase with other 50 mL of CH2Cl2 (in the same way you did before) and collect the two organic phases. 7) Put 10 g (or more if necessary) of MgSO4 in the collected organic phases: at this point the emulsion should break producing two well-separated phases. Filter the mixture directly into a new extraction funnel and separate again the organic phase. 8) Dry the organic phase with about 1 spatula of MgSO4, stir for 5 minutes and filter the solid away. 9) Remove the solvent with a rotavap. A solid residue, containing the caffeine as a main substance, should be obtained. Purification of caffein by crystallization 10) Dissolve the residue in about 6 mL (or more, if necessary) of hot acetone and add hexane dropwise to the solution until the solution becomes slightly cloudy. 11) Let the cloudy solution slowly cool down to room temperature: crystals of caffeine should separate from the solution. 12) Filter the crystals and dry them overnight.

13) Measurement of IR and melting point (236 C).

Information of Caffeine:

When coffee or tea is brewed, caffeine is dissolved into the water along with tannins. These tannins are what give the coffee its dark color. Since we are focused on isolating only caffeine, the tannins need to be removed. The addition of Na2CO3 reacts with the tannins to form a salt. These salts are soluble in water but are insoluble in an organic solvent such as dichloromethane. The solubility of caffeine in water is 2.2 mg/mL at 25C, 180 mg/mL at 80C, and 670 mg/mL at 100C. It is quite soluble in dichloromethane, the solvent used in this experiment to extract the caffeine from water.