HERMIN HARDYANTI UTAMI (111 304 0202)

CHEMISTRY DEPARTMENT MATHEMATIC AND SCIENCE FACULTY STATE UNIVERSITY OF MAKASSAR 2012

RATIFICATION PAGE The complete report of Organic Chemistry II with the title of Caffeine Extraction which made by : Name ID Group Class : Hermin Hardyanti Utami : 111 304 0202 : VII : ICP B

Have been checked by assistant and assistant coordinator. So, this report is accepted. Makkassar, December Assistant Coordinator Assistant 2012

Fandi Ahmad, S.Pd. Known By, Responsibility Lecturer

Muh. Jufri

Dra. Hj. Ramdani, M.Si.

A. Title of Experiment
Caffeine Extraction

B. Purpose of Experiment
Known continue extraction with heat intermediately

C. Preview of Literature
In this course in term extraction refers to the process where by a component in a mixtures is transferred into another solvent phase. The operation involves shaking an immiscible pair of liquids, where by a solute passes from a liquid to the other. Commonly one of the liquids will be an aqueous (water) solution an the other an organic solvent (e.g diethyl ether or CH2Cl2) or a solution involving an organic solvent. Before using the separating funnel, apply a thin coat of grease or when dicholoromethane is used as solvent a film of water to glass tap (DO NOT grease teflon taps). Check for leaks by adding a small volume at the solvent to used to the separating funnel with the tap inserted and closed (Anshori, 2005: 1). The ease with which amines are extracted into aqueous acid, combined with their regeneration on treatment with base, make it a simple matter to separate amines from other plant materials and nitrogen containing natural producucts were among the earliest organic compounds to be studied. Their basic properties lead amines obtained from plants to be called alkaloids. The number of known alkaloids excededs 5.000. They are special interest because most are characterized by high level of biological activitity. Some examples include cocaine, consine, and morphine.
O O CH3

Cocaine (a central nerveus system plant).

C 6H 5

stimulant

obtained

N H 3C

from the laeves of the coca

O

HO

Morphine ( an opium alkaloid, although it is an excelent analgesic, its use is restricted because of the potential for addiction. Heroin is the

O N H HO CH3

diacitate ester of morphine)

(Carey, F.A. 2001: 869).

A natural product is a compound synthesized by a plant or animal. Alkaloids are natural products that contain one or more nitrogens and are found in leaves bark, roots or seeds of plant. Example include caffeinee (found in tea leaves, coffee beans, and colanuts) and nicotine (found in tabacco leaves). Morphine is an alkaloids obtained from opium the juice derived from a species of puppy. Morphine is 50 times than aspirin as an analgesic but it is addictive and suppresses respiration. Heroin is a synthetic compund that is made by acetylating morphine.
O H 3C N N CH3 CH3 N

CH3 N

N
N

CH3 N

Cl C 6H 5

Caffeine

Nicotine

Valium (Bruice, PY. 2003: 884).

Caffeinee (1, 3, 7-trimethylvathine) is an habitual substance present in a wide variaty of a beverages and in chocolate-besed foods and it is also as drugs. The antioxidant ability of caffeinee has been reported in contrast with its prooxidant effects derived from its action mechanism such as systemic release of catholamines. The aim of this work was to evaluate the effect of caffeinee on exercise ovaditive stress, measuring plasma vitamins A, E, C, and melonaldhyde (MDA) as markers of nonenzimatic antioxidant status and lipid peroxidation respectively (Olcina. 2006: 621).

Caffeinee (C8H10N4O2) is an alkaloid are bitter tasting natural nitrogen containing compounds found in plants. The basic property of alkaloids comes from lone pair of electrons found on at least one nitrogen. Alkaloids are often found to have potent physiological activity. Some better known examples are morhine, heroin, lysergic acid (LSD), cocain quine, strychine and nicotine. The basic N in caffeine can be to increase or decrease is water solubility as a cation. On the other hand if caffeinee is in the basic environment it takes the neutral form, and is only some somewhat polar. Tea leaves contains tannins which are acidic as well as a number of colored compounds and small amount of undercomposed chlorophyll (soluble in chloromethane). The solubility in water is 2,2 mg/mL at 25C, 180 mg/mL at 80C, and 670 mg/mL at 100C. Caffeinee can be aesily extracted from tea bags. The procedure one would see to make a cup of tea simply stepping the tea with very hot water for about 7 minutes, extract most of the caffeinee (Caballero, M.J. 2001).

D. Apparatus and Chemicals

1. Apparatus a. Soxlet equipment, 1 piece b. Breaker 250 mL, 1 piece c. Buchner funnel, 1 piece d. Beaker glass 1000 mL, 1 piece e. Graduated cylinder 25 mL, 1 piece f. Porceline cruicible, 3 pieces g. Stative and clamp, 1 piece h. Wash bottle, 1 piece i. Bunsen, casa, tripot, 1 piece j. Hot plate, 1 piece k. Separating funnel, 1 piece l. Erlenmeyer m. Balance, 1 piece n. Stirbar, 3 pieces

o. Rough and smooth cloth, 1 piece p. Wood clamp and spoon, 1 piece q. Boiling stone 2. Chemical a. Tea b. Ethanol 96% c. MgO d. Aluminium foil e. Boiling water f. H2SO4 dilute g. Filtering paper h. Aquadest i. Matches j. Ice cube k. Chloroform (CHCl3) l. Whatmann filtering paper

E. Work Procedure
1. As many as 50,00 grams of tea is balanced. 2. The tea is covered with filtering paper and it is bond. 3. The tea that already (after covered) is put in soxlet and the ethanol is poured through the tea until a half of rounded flask. 4. The extraction process is done and it is waited until obtained 10th circulation. 5. As many as 17,5 grams of MgO suspension solved in 150 mL H2O. 6. Let it dry when vapor. 7. Extract the powder with boiling water 250 mL (incruicible) and suck while heat with buchner. 8. Repeat it 3 times with boiling water 125 mL. 9. It solution collect becone one after added 25 mL H2SO4 dilute. 10. Vaporate until 1/3 initial volume.

11. Extract with separating funnel with 15 mL chloroform 5 times. 12. Chloroform is vaporated and recris if there is crystal. 13. Test melting point to know the purity.

F. Observation Result
No. 1. 2. 3. 4. 5. Observation Meassured sample (tea) Filled sample to filtering paper Added ethanol to soxhlet Set soxlet and filled Noted circulation 1st 2nd 3rd 4th 5th 6th 7th 8th 9th 10th 6. 7. 8. 9. 10. 11. 12. Taken extract 150 mL water Vapored it Mixtured with water 250 mL mL water Vapor it until 1/3 volume Filtered with buchner Brown solution Brown solution Until formed powder Black solution 12 minutes 12 minutes 12 minutes 12 minutes 10 minutes 10 minutes 10 minutes 10 minutes 8 minutes 8 minutes Brownish black solution 3 times circulation Sample in soxlet and tea colour isnt concentration Result 50 g tea

Mixed with MgO suspension and Green brown solution

Filtered it buchner and 2 times 125 Black solution

13.

Filled to separating funnel + 15 ml Separate 3 layers : chloroform + shaked (5 minutes) - Brown Solution - Brown Transparant - Transparant solution

14. 15. 16. 17.

Taken transparant solution and keep it calm The solution is heated Balanced dust if caffeine Determine dust caffeine melting point

Transparent solution Dust of caffeine (yellow) 0,1596 g yellow dust 196-202C

G. Discussion
In this experiment, used sample is tea, where tea is covered with filtering paper and then into soxlet. Caffeine extraction from tea did with continuous extraction by heating process with soxlet. The basic principal of soxlet is extraction of compound in solid phase (tea) with liquid solvent (ethanol). In the extraction process, used ethanol as the solvent because ethanols properties are equal with caffeine, they are polar and low boiling point. In the extraction process, some boiling stone is added into rounded flask in order to prevented explossion occured in the rounded flask. In this stage, soxlet was set and the ethanol were vaporated until three times circulation, the tea also covered with filtering paper and then ethanol were heated. When the athanol condensed and passed through condensor, the tea became liquid and collected until the ethanol back down to to rounded flask. Heating process did until 10 times circulation. The first till the 4th circulation were 12 minutes, the 5th till the 8th circulation were 10 minutes, and the 9th till the 10th circulation were 8 minutes. Caffeine is an alkaloid derived from coffee bean, tea leaves, and cacao leaves. This extraction use tea because tea containing 4-5% caffeine more than coffee. Caffeine is an alkaloid which contains alkali nitrogen with 194,19 grams of molecular weight. The chemical formula of caffeine or 1, 3, 7trimethylxanthyne is C8H10N8O2 with chemical structure:

O H 3C N N CH3

CH3 N

This extraction ended when the solution became thick or saturated. It means the acquired extract is caffeine from tea (separation between caffeine from tea powder). The result of this extraction was black-brown solution. This solution added with suspension of MgO in water. suspension of MgO in water were to help the solvent to push the caffeine from tea until it soluble into water and to got the chemicals in tea, addition of MgO also purpose to kept structure of caffeine when heating. Then the product solution vaporated till become powder. This vaporation purposed to vaporing the solvent. After that both solution and powder separated by filterizing. When filterizing occured, this solution added with hot water because hot water could open the pores of caffeine so that there were more caffeine extract and it could be extracted perfectly. The obtained filtrate were have to be thicked again until 1/3 initial volume to vaporate water in filtrate so that consentration of caffeine became thicker and another chemical that consist in could be passed away. But before thicked, the filtrate added dilute sulfuric acid (H2SO4) to decrease solution pH so that the structure of caffeine would not damaged. In high pH (alkali), the structure of caffeine is easily damaged so that its important to added some acid. Then this solution strained again. The filtrate from last strain were into separating funnel. After that added 15 mL chloroform (CHCl3) into it. The filtrate were into separating funnel should be in room temperature because if it were too cold, the solution would be precipated because high molecular weight and pressure. Addition of choloroform did 5 times, and shaked every in addition to increase contact chance between caffeine and chloroform. This shaking might not too strongly because could result emulsion between chloroform and water. While it were shaked, tap of separating funnel opened occasionally so that volatile chemical from extract could be vaporated. Addition of chloroform were to bind caffeine from solution so that

caffeine separated from another chemical in solution. Caffeine binded to chloroform because chloroform were nonpolaric compound that could binding another nonpolaric compound like caffeine. The shaked solution devided into 3 layer. The upper layer was brown because containing residue. The middle layer was light brown. It was caffeine which still mixed with residue. The bottom layer was transparent. Smaller density would be on upper layer. Caffeine solution filtered with buchner strainer so that caffeine separated from another chemical. This solution added chloroform once more so that remaining caffeine could be separated perfectly. Separated caffeine heated to vaporating chloroform in solution. Result of this vaporation were 0,1596 grams of yellow powder. This powder were purity tested and acquired 196-202C melting point. It was different with theory because caffeines melting point was 227-202C in theory. It was occured because the tea were mixed with another chemical and also caffeine were not soluble perfectly. The reaction of this experiment is :
H N O H 3C H N

HN HN

+
N H

N N CH3

2C 2 H 5 OH O N

(1, 3-dimethylxanthyne)
O H 3C N N CH3 H 3C N N CH3 H N

+
N

MgO

H 2O

2CHCl

CH3 N

+
N

O2

3Cl 2

Mg

2+

(1, 3, 7- trimethylxanthyne)

H. Closing
1. Conclusion a. Caffeine is extracted from tea because of continuous extraction process through heating 2. Suggestion a. Apperantices should be carefull when adding chloroform. b. Laborant must prepare our apparatus and chemical. c. Assistant should be diligent to teach us about the procedure.

BIBLIOGRAPHY
Anshori. 2005. Organic Chemistry. Bandung: Padjadjaran University. Bruice, P.Y.. 2003. Organic Chemistry 4th edition. London: Longman Valey. Caballero, M.J.. 2001. Extraction of Caffeine From Tea Leaves. USA: Dragon Alley. Carey, F.A.. 2001. Organic Chemistry 4th edition. Virginia: M.C. Graw Hill. Olcina, dkk. 2006. Effect of Caffeine on Oxidative Stress During Maximum Incremental Exercise. Spain: Journal of Sports Science and Medicine.

ANSWER OF QUESTION
1. Structure of caffeine is :
O H 3C N N CH3 CH3 N

2.

Ethanol used bacause it is polar compound and also caffeine could be bond with polar compound, So, caffeine could be solvent in ethanol and ethanol is volatile so it will be easy to evaporated.

3.

The melting point of a compound, specially it can be used to determine the purity of caffeine if the interval is 1C because the characteristic of pure compound has interval of melting point as much as 1C.