Chem143 Lab 3

Martin Case/Corinne Sadlowski

Extraction and Recrystallization of Caffeine

http://en.wikipedia.org/wiki/Recrystallization_(chemistry) http://en.wikipedia.org/wiki/Caffeine Write-up for this lab to be completed on 10/6 and 10/8 Reagents and Equipment Caffeine tablets (2 each) Ethyl acetate (50 mL) Ethanol (20 mL) Caffeine TLC standard (few mg) TLC eluents (25 mL each) Chloroform Methanol Pestle and mortar 250 mL Erlenmeyer flask Separatory funnel 125 mL Erlenmeyer flask (2) Buchner funnel Vacuum flask TLC plates (silica, 5 x 3 cm, 10 plates) 100 mL beaker Filter paper Foil Capillary tubes Hand-held UV lamp Purpose The isolation, purification and structural analysis of physiologically active organic molecules from plants, animals and fungi are important aspects of organic chemistry. Many potent chemotherapeutic agents such as penicillin and taxol are natural products that were originally isolated and characterized by organic chemists. The purpose of this and the next lab is to introduce to you to this process of extraction, purification and characterization. Specifically, in this lab you will isolate and purify caffeine from a commercial preparation. In the next lab you will examine its nuclear magnetic resonance (NMR) spectrum. The use of teas and coffees as drinks is routine for most of us. The caffeine content of teas varies from 1-5% and for coffee between 1-1.5%. Although tea is slightly higher in caffeine concentration more coffee is generally used to brew a cup of coffee so the consumption of caffeine is higher when drinking coffee. Caffeine is a central nervous system (CNS) stimulant. It is used to increase alertness, brighten spirits and combat fatigue. The extraction of caffeine from tea and coffee is very messy and contamination with other compounds is a problem. This weeks lab will attempt to extract caffeine from No Doz or Vivarin tablets available as an over-the-counter formulation. The caffeine is extracted into ethyl acetate and the crude product is purified by recrystallization from ethanol. The purity of the product will be assessed by TLC.

Chem143 Lab 3

Martin Case/Corinne Sadlowski

Experimental Procedure 1. Extraction of caffeine Weigh 2 No-Doz or Vivarin tablets and crush using a mortar and pestle. Place the resulting powder in a 250 mL Erlenmeyer flask containing 100 mL of distilled water. Boil for 5 mins on a hotplate, remove from heat, and allow to cool to room temperature. Remove the suspended solids via suction filtration using a Buchner funnel, a vacuum flask (125ml), and an aspirator to apply a vacuum. Wet the filter paper before decanting the mixture to ensure proper suction. Transfer the supernatant to a separatory funnel. Add 30 mL ethyl acetate to the funnel, noting which layer is aqueous and which is organic (the density of ethyl acetate is 0.902 g/mL). Place the stopper in the top of the funnel, make sure the stopcock is closed, and shake while holding onto the top. Relieve built up pressure by releasing the stopcock (with the funnel inverted!). Return the separatory funnel to a resting position in a ring clamp and allow the layers to separate. Remove the stopper and collect the bottom layer in a 125 mL Erlenmeyer flask. If an emulsion occurs in which there is not a defined 2-layer system, add a few mL of saturated NaCl solution to break it up. Drain the top layer into a clean 125 mL Erlenmeyer flask. Close the stopcock, return the aqueous layer to the funnel, and add another 20 mL of ethyl acetate. Extract as described above, combining the organic layer with the previous extraction. Keep a few drops of the ethyl acetate extract aside in a capped vial for TLC analysis. Place the Erlenmeyer containing the organic layers on a hotplate in the hood (set between 3 and 4) and boil gently until all the solvent has evaporated, leaving behind a white solid. 2. Recrystallization of caffeine Add 15 mL ethanol to the white solid and gently warm to dissolve the impure caffeine in the solvent. If the solid does not dissolve, add an additional 5 mL of ethanol. Once dissolved, allow the flask to reach room temperature and then place it in an ice bath until crystals are observed. It may be necessary to scratch the sides of the flask to induce crystallization. Allow crystals to collect for about 10 mins. Vacuum filter the recovered crystals using a Buchner funnel and allow the vacuum to air-dry the crystals for about 5 mins. Weigh the crystals and calculate a yield by comparison to the weight and percent composition of the tablets. Place the recrystallized caffeine in a 10 dram snap-top vial, label the vial with your name and caffeine from lab 3, and place in your drawer for NMR analysis in the next lab. 3. TLC analysis You should spot the crude ethyl acetate extract, the recrystallized caffeine and an authentic sample of caffeine (3 spots). (a) Use a pencil to draw a baseline ~1 cm from the bottom of a 5 x 3 cm silica gel TLC plate. Mark the line 3 times at roughly equal intervals so that you know where to spot your samples. Dont mark too close to the edge of the plate. Make a note of which spots will correspond to which sample. (b) In Lab 1 you should have identified a good TLC eluent for caffeine. Use this to run your TLC. Visualize by UV, calculate the Rfs for the compounds, and sketch the TLC plate and the results in your notebook.

Chem143 Lab 3

Martin Case/Corinne Sadlowski

Write-up Report the yield of recrystallized caffeine. Comment on the purity of the crude extract compared to the recrystallized material. If you use any on-line or library resources, list them at the end of your report. Waste disposal Caffeine and water are not regulated as hazardous waste. Ethyl acetate and ethanol are regulated as hazardous wastes because they are ignitable below 140 F. The filter paper with ground tablet residue is non-hazardous and can be disposed of in the trashcan. The water layer from the extraction should contain only water and caffeine, but may be contaminated with ethyl acetate. Dispose of as chemical waste in the appropriate waste container. The ethanolic filtrate from the recrystallization contains ethanol and trace amounts of ethyl acetate. Dispose of as hazardous waste in the appropriate waste container. TLC plates may be contaminated with solvents. Discard as dry chemical waste in the solid waste container. Do not mix solid and liquid wastes. Pipettes and capillary tubes should be placed in the broken glass box at the front of the laboratory. Safety Your pre-lab should include a comprehensive safety assessment of all the solvents and chemicals used in this lab. Hot hotplates look a lot like cold hotplates, so dont touch the ceramic surface. Do not shine the UV lamp into unprotected eyes. Do not consume any caffeine prepared during this experiment, or any of the caffeine tablets. Assume that everything in a lab is contaminated with toxic material.