Single Extraction of Caffeine from Tea leaves

Kimberly T. Victoriano, Steven John E. Villafuerte, Klarisa D. Viloria, Liana Alpha T. Yamzon Group 9 2F-Pharmacy Organic Chemistry Laboratory

ABSTRACT
The experiment was performed so as to differentiate single from multiple extraction and to be able to calculate the percentage yield of caffeine for both extraction procedures. The principles related to extraction were discussed. Like all of the experiments, it can be dangerous if handled carelessly. Dichloromethane is a suspected carcinogen. For faster completion, division of labor was observed. After preparing the sodium carbonate solution, we immersed it with weighed tea bags and allowed to boil for 10 minutes. Anhydrous sodium sulfate was weighed while waiting for the mixture to boil. The group was tasked to perform single extraction and after the two layers was clearly visible, the organic layer or the lower layer which contain Dichloromethane and the extracted caffeine was drained and was transferred into Evaporating dish with anhydrous sodium sulfate which was evaporated to dryness. The residue weighed and the percentage yield came of about 10%. This shows that there are caffeine present in the tea samples.

INTRODUCTION
The process of separating the organic compound into the main compound is called Extraction. It uses two immiscible phases to separate a solute from one phase into the other. There are two types of extractions performed in the laboratory: single extraction and multiple extractions. Single extraction is done when the dichloromethane is introduced once while multiple extraction, dichloromethane is introduced three times. In this experiment, we used particularly Liquid-liquid single extraction, also known as solvent extraction and partitioning which uses a separatory funnel. Extraction process selectively dissolves one or more of the mixture compounds into an appropriate solvent. The objective of experiment is to isolate the caffeine from the tea sample. Caffeine is a bitter substance found in coffee, tea, soft drinks, chocolate, kola nuts, and certain medicines. It has many effects on the body's metabolism, including stimulating the central nervous system. This can make you more alert and give you a boost of energy. Caffeine belongs to a family of naturally occurring compounds known as xanthines. Xanthines are therapeutically active compounds found in plants and organism. They have a psychostimulant effect and help improve concentration and cognition. Caffeine is chemically 1,3,7trimethylxanthine .

Figure 1. Structural Formula of Xanthine

The two major xanthines found in plants are Caffeine (in coffee, guarana, mate and tea) and Theobromine (in cocoa and mate). Theophylline is also naturally found in tea as traces.

Figure 2. Structural Formula of Theobromine commonly found in chocolates.

together with other compounds in particular, the tannins that are slightly soluble in the dichloromethane which can be eliminated by converting it to their salts (phenolic anions) by adding sodium carbonate, which remain in the water. Caffeine is very soluble in Dichloromethane. When dichloromethane is added to the previous water-caffeine solution, the caffeine is immediately transferred to dichloromethane. The addition of dichloromethane produces two layers. Dichloromethane can be seen on the bottom layer of the separatory funnel since it is denser compare to water. The upper and lower layer is separated by decantation or by carefully opening the knob of the separatory funnel. After decantation, the solution is added by anhydrous sodium sulfate to trap the water in the solution and after spontaneous evaporation, it is definite that caffeine was the only substance left in the evaporating dish.

EXPERIMENTAL A. COMPOUND TESTED

The tea bags used was Lipton Unflavored tea with caffeine.
Figure 3. Structural Formula of Caffeine commonly found in coffees.

Extractions can be performed by utilizing the different chemical properties of a certain solvent. The solvent used in the experiment is water. The solubility of caffeine to water is necessary to create a solution of water and caffeine which will be mixed with dichloromethane. First, caffeine will be extracted from tea leaves by boiling them in water. Although caffeine is soluble with water, the caffeine will remain in the solution

There is a 55mg of caffeine per 8 fl. Oz cup of tea.

B. PROCEDURE

The experiment required a Bunsen burner, separatory funnel, Erlenmeyer flask, glass rod, evaporating dish, watch glasses, iron stand, iron ring, iron clamp, unflavored tea bags with caffeine, sodium carbonate, dichloromethane and sodium sulfate. As an odd number group we were assigned to take single extraction. First, weigh the evaporating dish, weigh 4.4 grams of sodium carbonate in a 250mL beaker which was dissolved in a pre-heated 100ml of distilled water. Add 10g of tea leaves contained on a teabag to the said mixture. Let it boil for 10 minutes in low flame. Remove the teabag and squeeze it using two watch glasses. Before the mixture was transferred in the separatory funnel, it was cooled by having it in a running water this was too eliminate the pressure emitted if the mixture was transferred in the separatory funnel when hot. After cooling, the mixture was transferred to the separatory funnel and the dichloromethane

was added . The separatory funnel was turned upside down and the stop cock was opened so to release the pressure inside. To mix, the solution was swirled and was turned upside down to release again the pressure inside. This procedure was repeated for two minutes. After swirling, the two layers will be evident; the lower layer was drained to a beaker and treated with Sodium sulfate. It was spontaneously evaporated and the residue is caffeine from the tea leaves.

RESULTS AND DISCUSSION

The experiment followed the single extraction and it accumulated less caffeine than of the multiple extractions because there is repeated extraction process. Notice in the picture that there are two layers. The upper layer was aqueous layer while the lower layer was the organic layer. The organic layer was composed of the Dichloromethane and the caffeine. The caffeines can be extracted from the leaves by boiling them in water. The tannins found in the tea is eliminated due to the sodium carbonate solution. The purpose of anhydrous sodium sulfate was

a drying agent. It absorbs all remaining water present in the mixture. Table 1. Data Gathered Weight Of The Tea Leaves Used Weight Of The Empty Evaporating Dish Weight Of The Evaporating Dish With The Extracted Caffeine Weight Of The Caffeine 10 Grams 130 Grams

Internet Sources:

http://www.nlm.nih.gov/medlineplus/caffeine. html obtained July 24, 2013 http://firstyear.chem.usyd.edu.au/prelab/e28.s html obtained July 24, 2013 http://www.scribd.com/doc/24382592/Extracti on-of-Caffeine-From-Tea-Leaves obtained July 24, 2013 http://www.bioxtract.com/plant-basedactives/xanthines/index.html obtained July 24, 2013

131 Grams

1 Gram

Percentage Yield
% yield =

% yield =

% yield = 10 %

A percentage yield of 10.0% was computed after getting the ratio of the weight of caffeine and weight of tea leaves used and was multiplied by 100.This means that for every 10.00 g. of tealeaves, an amount of 0.1 grams of caffeine is contained.

References
Book: Bayquen, A. V., Cruz C. T., de Guia, R.M., Lampa, F.F., Pena, G.T., Sarile, A.S.,Torres, P.C.(2009) Laboratory manual in Organic Chemistry. Quezon city, Philippines.: C & E Publishing