1 Extraction of Caffeine from Tea Leaves Janine Galicia*, Angelica Estorga, Cristina Gigante, and Adrian Go

Department of Chemistry, University of Santo Tomas, Manila, Philippines

Abstract Caffeine exists in tealeaves and can be easily extracted which was demonstrated in this experiment.In the experiment, teabags were boiled for 5 minutes followed by extraction using dichloromethane, with all washings taking place inside a separatory funnel. The remaining substance was then evaporated until only the crude caffeine was left. Sublimation was then used to extract the pure caffeine from the crude caffeine. Weight of sublimate is 0.0032g, % yield of caffeine is 0.075012% and melting point of the pure caffeine is 229 oC to 240 oC.

Introduction The purpose of this experiment is to isolate, purify and characterize caffeine from the tea leaves and to calculate the percentage yield of caffeine. Caffeine is considered the most commonly used psychoactive drug in the world. Approximately 80% of the world's population consumes it on a daily basis, and continuous research is being done on its health benefits and consequences. Caffeine is the common name for 1,3,7-trimethylxanthine. When purified, caffeine produces an intensely bitter white powder that provides a distinctive taste in soft drinks. [2] Caffeine belongs to a large class of compounds known as alkaloids. These are of plant origin, contain basic nitrogen, often have a bitter taste and complex structure, and usually have physiological activity. It is naturally found in certain leaves, seeds, and fruits of over 60 plants worldwide. The most common sources in our diet are coffee, tea leaves, cocoa beans, cola, and energy drinks. Caffeine can be easily extracted from teabags. The procedure one would normally do in making tea simply putting the teabags in hot water for a few minutes extracts most of the caffeine. Since caffeine is white, fine and powdery, it is obvious that water extracts more than just caffeine. The brown aqueous solution is subsequently extracted with dichloromethane to separate caffeine from other substances. Evaporation of the solvent leaves crude caffeine. Sublimation of the crude caffeine then yields pure caffeine. Purity of the pure caffeine is then tested through melting point.

Results and Discussions

Color Crude Caffeine Pure Caffeine Yellow Green White

Appearance Silky Feather - like Powdery

Shape Hair like Spikes

Size Fine Strands Fine Powder

Weight of sublimate = 31.4671g 31.4639g = 0.0032g

% yield of caffeine :0.0032 g x 100 4.2650 g Melting point : 229 oC 235oC = 0.075012%

Decantation was used in extracting the caffeine from the teabags in the boiling water.

Decantation is the process by which, a clear liquid obtained after sedimentation, is transferred into another container, without disturbing the settled particles.
Crude Caffeine wasobtained through Extraction. Extraction is a very common

laboratory procedure used when isolating or purifying a product. In this procedure, the organic product is isolated from inorganic substances. Here the organic solvent dichloromethane is used to extract caffeine from aqueous extract of tea leaves because caffeine is more soluble in dichloromethane . Gently shaking the separatory funnel was necessary to ensure the solvent moves amongst the tea leaf particles to extract all the caffeine. It agitates the tea leaf particles and separates any that are clumping together and hindering efficient extraction. It is also imperative to open the stopcock of the separatory funnel to vent it of any pressure building up inside. The separatory funnel must not be shaken vigorously because emulsion might form. Emulsion is the mixture of 2 or more immiscible liquids. Sodium hydroxide was used to make sure that other substances, which are slightly soluble to dichloromethane are eliminated by converting them to their salts that remain in the water. Anhydrous Sodium Sulfate was used as the catalyst in drying up the mixture. Catalysts are substances that speeds up a chemical reaction.

3 Pure Caffeine was obtained through Sublimation. Sublimation is the term for when matter undergoes a phase transition directly from a solid to gaseous form, or vapor, without passing through the more common liquid phase between the two. Melting point for purity was used as characterization. A closer melting point range signifies good confirmation for judging that a substance to be pure. Far melting point ranging signifies that the substance is not pure. In the experiment, we determined 2 melting points of substances, the standard and the sample caffeine. The standard had a melting point of 228oC to 230oC while the sample caffeine had a melting point of 229 oC 235 oC indicating that the standard was more pure than our sample caffeine. Crude Caffeine appeared to be yellow green in color, silky feather like appearance, hair like and fine. Pure Caffeine appeared to be white, fine and powdery. Weight of the sublimate was obtained by subtracting the weight of the empty vial from the weight of the vial with the pure caffeine.

Experimental The 3 teabags were opened and the weight of the combined tealeaves was recorded. The tealeaves were then returned in the bag; secured with a string and staple wire. The teabags were boiled in water (100 mL) for 5 minutes. The extract was then left to cool down. After cooling down, the tea extract was transferred in a separatory funnel containing DCM (20 mL). The separatory funnel was gently shaken 3 times after which the caffeine is already extracted. Pressure was released constantly. DCM lower layer as drained into a clean flask. The extraction was repeated thrice DCM (20 mL) on each repetition. DCM portions were combined. Water layer was discarded. The combined DCM was returned into the separatory funnel and was washed with NaOH solution (20 mL 6M). NaOH layer was discarded. DCM layer was drained into a clean dry beaker containing half spatula of anhyd Na2SO4. Solution was swirled to allow Na2SO4to settle. The solution was then placed in the lockers for drying up. After drying up, the crude caffeine was scraped from the beaker and was transferred in a filter tube with a fitted inner test tube serving as cold finger and into a hot air bath for at least 35 minutes. The cold finger was constantly refilled with ice water. Inner tube was carefully removed. Caffeine clinging in the cold finger was scraped off and was transferred in a vial. % yield was calculated. Weight of the sublimate was also recorded. With a mortar and pestle, caffeine crystals were grinded into a very fine powder. One end of a micro capillary was sealed by heating while rotating it at a 45-degree angle from the blue potion of a Bunsen Burner flame. Pulverized caffeine was scooped using the open end of the microtube. Caffeine were packed well at the bottom of the tube by letting it fall inside a 1 meter long glass tubing and letting it bounce up and down a table top. Same was done on the standard caffeine. Both standard and caffeine sample were tied against a thermometer. Thermometer was clamped and dipped in a beaker filled with cooking oil. Cooking oil was heated with a Bunsen Burner flame. Cooking oil was constantly stirred to evenly distribute the heat. Temperature range was recorded between the first appearances of liquid within the sample to the disappearance of the last traces of solid.

References: DeBartolo, M. (Fall 2002). Extraction of Caffeine from Tea. Retrieved January 3, 2011, from http://ochemonline.pbworks.com/f/08_caffeine1.pdf Garcia, C., &Manansala T. L. (November 2008).Laboratory manual in Organic and Biochemistry. University of Santo Tomas College of Science. Kovaks, B. (2007, June 26). What is Caffeine? Caffeine. Retrieved January 3, 2011, from http://www.medicinenet.com/caffeine/article.htm. Mohrig. Extraction Theory and General Procedure.Extraction. Retrieved January 3, 2011, from http://www.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/Techniq ues/Extraction/