OBJECTIVE To determine the amount of crude caffeine in the tea bag.

INTRODUCTION Caffeine is a member of the class of compounds organic chemists call alkaloids. Alkaloids are nitrogen containing basic compounds that are found in plants. They usually taste bitter and often are physiologically active in humans. The names of some of these compounds are familiar to you even if the structures arent: nicotine, morphine, strychnine, and cocaine. The role or roles these compounds play in the life of the plants in which they are found is not well understood. Caffeine is found in a number of things ingested by people. The table to the right lists some of them. Caffeine acts as a stimulant. It stimulates the heart, respiration, the central nervous system, and is a diuretic. Its use can cause nervousness, insomnia and headaches. It is physically addictive. Tea leaves consist mostly of cellulose, a water-insoluble polymer of glucose, which is a simple sugar which is it is a monosaccharide. Cellulose performs a function in plants similar to the fibrous proteins in animals. Along with the cellulose are found a number of other things including caffeine, tannins that it is a phenolic compound whereas this compound had an -OH directly bonded to an aromatic ring and a small amount of chlorophyll.

Tea leafs contain from 2 to 5% caffeine, along with cellulose, tannins, flavonoid pigments and chlorophylls. The caffeine can be extracted from tea using hot water. However, the tannins, pigments and chlorophylls will also be extracted into the water. The caffeine can then be extracted from the water using methylene chloride (dichloromethane). Since the tannins are acidic, base is added to the aqueous extract in order to ionize the tannins and insure that they remain in the aqueous layer. Along with the caffeine, the chlorophylls (which are present only in small quantities) will also go into the organic layer.

PROCEDURE 1. Round bottom flask and tea beg was weighed and recorded. 2. 50ml of water was filled into 100ml beaker. 3. The beaker was covered with watch glass and the water was heated on a hot plate until the water almost boiling. 4. The tea bag was inserted into the hot water until 15 minutes. 5. The hot tea was transferred into small conical flask and 0.5g of sodium carbonate was added. 6. The solution was filtered into small separatory funnel and cotton was used for filtration. 7. 15ml of methylene chloride was added to separatory funnel and the extraction was started. 8. The lower methylene chloride layer and 10ml of fresh methylene chloride was added. This step was repeated twice. 9. The combined methylene chloride layer was dried using anhydrous sodium sulphate. 10. The dried methylene chloride solution was transferred into pre-weighed small round bottomed flask and the solvent was evaporated using the rotary-evaporator. 11. The round bottomed flask was weighed and the result was recorded. RESULT Mass of empty round bottom flask Mass of round bottom flask+ crude caffeine Mass of crude caffeine Mass of petri dish Mass of petri dish + tea bag Mass of tea bag Mass of sodium carbonate Weight percent recovery of caffeine form tea bag = = = = = = = = 45.8728 g 45.921 0.0483 g g

58.0098 g 60.5929 g 2.5831 0.5002 1.8700% g g

CALCULATION The equation for calculating the percentage of caffeine in tea bag is as follows:
amount of caffeine recovered percentage of caffeine = -------------------------------------- x 100% weight of tea

0.0483 g percentage of caffeine = -------------------------------------- x 100% 2.5831

= 1.8700 % DISCUSSION Caffeine can be extracted easily from tea bags. The procedure one would use to make a tea solutions with very hot water for a few minutes to extracts most of the caffeine. Since caffeine is white, slightly bitter, odorless, crystalline solid, it is obvious that water extracts more than just caffeine. When the brown aqueous solution is subsequently extracted with dichloromethane, primarily caffeine dissolves in the organic solvent and the evaporation process will leaves crude caffeine. The idea in this experiment is to extract the water soluble materials in the tea bag into hot water. From the theory, the solubility of caffeine in water is 22 mg/ml at 25oC, 180 mg/ml at 80oC, and 670 mg/ml at 100oC. Caffeine is an alkaloid and organic base. The function of sodium carbonate (NaHCO3) was added in the first extraction to ensure the caffeine remains in the free base form. In other word, NaHCO3 was added to control the pH value of the solution. Besides that, water and the tannins will be converted to phenolic anions, which are not soluble in the dichloromethane but are soluble in highly polar water.

The hot solution then was allowed to cool at room temperature and the caffeine is then extracted from the water with dichloromethane (methylene chloride), which is an organic solvent that is insoluble in water. Since caffeine is more soluble in dichloromethane (140 mg/ml) than it is in water (22 mg/ml), it readily dissolves in the dichloromethane. However, the tannins are slightly soluble in the dichloromethane. But in this experiment, we want to separate the caffeine from the tannins by having the caffeine dissolve in the dichloromethane and the tannins remain in the water. We can do this by taking advantage of the fact that phenols are acidic enough to be converted to their salts (deprotonation of the -OH group) by reaction with sodium carbonate.

From the experiment, the concentrated tea solution is extracted with added dichloromethane. From that, emulsion was formed. There are substances in tea that cause small droplets of the organic layer to remain suspended in the aqueous layer. Consequently, when extract the caffeine from the water into the dichloromethane we should not shake the separatory funnel vigorously because the caffeine will not be extracted into the organic layer. We need to use a gentle rocking motion of the separatory funnel. It is also to save and combine the dichloromethane extracts after each extraction. There are have an emulsion which is it is a cloudy layer between two clear layers whereas it is sometimes possible to break the emulsion by swirling the contents of the funnel or stirring the contents using a glass rod. Allow the layers to separate. Besides that, Methylene Chloride is denser than water so it will be the lower layer. The solution was extracted with 15mL portions of dichloromethane (CH2Cl2) and repeated twice with 10ml of fresh dichloromethane to ensure that all the crude caffeine does not leaves in the separatory funnel. The anhydrous sodium sulfate was added to dried the combined methylene chloride as a function as to absorb the small amount of water that is dissolved in the dichloromethane and small amounts of water from the aqueous layer that may have gotten into the flask. It is also as a function to break the emulsion.

Based on the experiment, we get the amount of caffeine in the tea bag is 48mg which is it is include in the range based on the theory, are 30-75mg per cup. So that we can conclude our result was acceptable because it is close to the expected values.

Dichloromethane will irritate the skin. So that, we need to wear gloves when working with CH2Cl2 and do not get dichloromethane on our hand as a precaution steps. We also need to avoid direct contact with these compounds. Evaporate the dichloromethane in the fume hood to keep exposure to a minimum. Besides that, make sure that the stopcock is closed when done the extraction process to make sure the extraction solution does not fill out from the separatory funnel. Furthermore, there are some systematic errors occur when we conduct the experiment such as we does not weigh the tea, but we weigh the tea bag, which has not only tea but also string and paper in its weight. When we squeeze the tea solution out of the tea bag, some of the liquid still containing caffeine remains behind in the wet bag.

CONCLUSION The amount of caffeine in 2.5831 g tea bag is 0.0483g. The weight percentage of recovery caffeine in a tea bag is 1.8700%. As the amount of caffeine in our experiment is 0.0483g (48mg) include in the range of the theory which is 30 -70mg per cup. We can conclude that our experiment success. REFERENCES http://ochemonline.pbworks.com/f/08_caffeine1.pdf http://facweb.northseattle.edu/amohamed/CHEM%20102N/Labs/Lab%206_Isolation%20of%20 Caffeine.pdf http://employees.oneonta.edu/knauerbr/chem226/226expts/226_expt06_pro.pdf http://www.usask.ca/chemistry/courses/255/laboratory/PDF/EXP1_Isolation%20of%20Caffeine. pdf http://web.fccj.org/~smilczan/ten/CAFFEINE.pdf

Full mark(s) Objective of the experiment Introduction Experimental procedure Result and observations Calculations Discussion Conclusion Answers to questions References Pre-laboratory techniques Laboratory techniques Total marks 1.0 2.0 1.0 3.0 3.0 2.0 1.0 3.0 1.0 2.0 1.0 20

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