Organic Chemistry Laboratory (2012 2013) 2A-BC: Experiment 2

Extraction of Caffeine from Tea Leaves with the Single Extraction Method Group 9: (author/ member no. 2) Miguel Lorenzo M. Tan Casis

Abstract: Extraction is defined as a separation method in which a solvent removes one or more soluble components from a mixture of solids, liquids, or both. The theory of extraction lies in the concept of immiscibility between two phases to separate a solute from the other phase, which is to be showcased by this study, being one objective. The others are to extract caffeine from tea leaves and compare single from multiple extraction. In this experiment, caffeine was extracted from tea leaves by using the single extraction procedure. A 10 g tea bag was boiled in a solution of anhydrous sodium carbonate and distilled water (4.4g and 100 ml respectively), then was placed in a separatory funnel with 60 ml of dichloromethane. The extract was drained into an Erlenmeyer flask then transferred into an evaporating dish containing half a spatula of anhydrous sodium sulphate, afterwards evaporated to dryness. The extract was then weighed and found to be 6.33 g. The percentage yield was computed by dividing the weight of the caffeine crystals (residue in evaporating dish) by the weight of the tea leaves used. The percentage yield was 63.3%. These results were compared with those obtained from multiple extraction in terms of their efficiency.

Introduction Extraction is defined as a separation method in which a solvent removes one or more soluble components from a mixture of solids, liquids, or both. The theory of extraction lies in the concept of immiscibility between two phases to separate a solute from the other phase. There are two main types of extraction in chemistry, namely Solid-Liquid Extraction and Liquid-Liquid Extraction (itself subdivided into two categories: simple and multiple). The latter, in practice, has an analyte with a favorable solubility towards an organic solvent. This results in the transfer of said analyte to the organic phase from the aqueous phase when the two immiscible liquids come in contact. Thus, the remaining steps are simply confined to decantation, mechanical separation, and evaporation (of organic phase).

Among the materials to be utilized in this experiment, tea is central, being the source of the component to be extracted: caffeine. This second-most popular drink in the world comes in a variety of forms-green, black, oolong- but is scientifically noted for its high content of polyphenols. This substance combats freeradicals and prevents cancer and other body ailments. With the tea leaves tough cellulose insoluble in water, boiling has been an easy separating method to get at the chemicals in store (e.g. caffeine, tannin, ascorbic acid, etc.). To isolate one of these components is a different matter, however. Pure caffeine is a white, tasteless substance that makes up as much as 5% of the weight of tea leaves. By structure, caffeine is closely related to the purine bases, guanine and adenine, found in deoxyribonucleic acids (DNA).

Its solubility in organic compounds is the reason for the inclusion of dichloromethane to act as the second of the two immiscible liquids. To disallow tannin from contaminating the organic compound solution, some procedures recommend bases such as calcium carbonate to be added to the aqueous solution beforehand, neutralizing and turning tannin into salts insoluble in dichloromethane. Objectives of the study, as hinted and inferred previously, would be the extraction of caffeine from tea leaves, computation of percentage of caffeine in the tea leaves, comprehension of extraction process, and comparison of efficiency between single and multiple extraction procedures. Scope would be limited to a single experiment involving extraction of caffeine from tea leaves using common lab apparatus. Methodology

4.4 g of anhydrous sodium carbonate was added to 100 ml of distilled water in a small Erlenmeyer flask. The solution was heated in a water bath till solute dissolved. Next, 10 grams of tea leaves in a tea bag was lowered into the flask and then the mixture was boiled for 10 minutes on a low flame. The excess liquid within the bag was also collected by pressing said bag against the side of the flask with a glass rod. Numbered as odd, the group assigned to this study opted to perform single extraction. Boiled tea solution was transferred into a separatory funnel, itself in place in an extraction setup. Afterwards, 60 ml of dichloromethane was added to the aqueous solution. To encourage the caffeine to dissolve into the dichloromethane, manual aggravation was required, with each group member taking turns to rotate the separatory funnel on the palm of their hand, allowing the contents to swirl, and occasionally opening the cap to allow air to escape.

Fig. 2 (Extraction Setup)

Fig. 1 ( Overview of Methodology)

Finally, after fifteen sets of rotations, the separatory funnel was set back onto the iron ring and left to stand for 2 minutes until the separation between the two layers was visible. Then, with a glass rod, the air bubbles

underneath the darker layer were scraped upward to remove them from the solution. The organic solution was drained into the Erlenmeyer flask beneath it and the aqueous solution was disposed of. Following that, the extract (organic solution) was transferred on to an evaporating dish with half a spatula of anhydrous sodium sulphate (the compound was to act as a drying agent to absorb excess water). The dish was subsequently covered with a parafilm which was punctured with holes, then put on a hot plate to evaporate to dryness. The entire dish with the extract was now weighed using an analytical balance. The figures that showed up were then subtracted by the weight of the dish alone (it was weighed previously using a triple-beam balance), to compute for the weight of pure caffeine: 6.33g. Then that amount was divided by the weight

found that the caffeine crystals were 6.33 g in all. With that weight divided by the amount of tea leaves (10 g) and then multiplied by 100, a percentage yield of 63.3 % was computed. Results obtained from multiple extraction were all significantly lower (e.g. 9.72 %), but the difference was a result of probable error on this studies part and not due to accepted fact. Outside sources have repeatedly stressed the superiority of multiple extraction.

References
http://www2.intota.com/experts.asp?strSearch Type=all&strQuery=chemical+extraction Date Accessed: July 22, 2012 http://www2.sci.uszeged.hu/inorg/Sample%20prep%20for%20org anics.pdf Date Accessed: July 22, 2012

of the tea leaves and then the quotient multiplied by 100, resulting in the percentage yield. Results and Discussion
A. Weight of Tea Leaves B. Weight of Evaporating Dish and Extract C. Weight of Evaporating Dish *D. Weight of Extract *E. Percentage Yield Fig.3 ( Table of Data Obtained) *D. Weight of Extract = 117.53 111.2 g = 6.33g *E. Percentage Yield = 6.33g/10g X 100 = 6.33 % 10g 117.53g 111.2g 6.33g 63.3 %

http://www.umm.edu/altmed/articles/greentea-000255.htm/ Date Accessed: July 22, 2012 http://www.o-cha.net/english/cup/pdf/38.pdf Date Accessed: July 22, 2012 http://www.scribd.com/doc/25378352/MULTIP LE-EXTRACTION-OF-CAFFEINE-FROM-DRIEDTEA-LEAVES-USING-DICHLOROMETHANE Date Accessed: July 22, 2012

The experimented ended with the drying of the extract. After weighing the filled evaporating dish (117.53 g) and then subtracting that amount to the weight of the evaporating dish alone (111.2 g), it was

http://answers.yahoo.com/question/index? qid=20080709222546AAXl8j4 Date Accessed: July 22, 2012