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 : Hermin Hardyanti Utami

ID : 111 304 0202

Group : VII

Class : ICP B

Have been checked by assistant and assistant coordinator. So, this report is

accepted.

Makkassar, December 2012

Assistant Coordinator

Fandi Ahmad, S.Pd.

Assistant

Muh. Jufri

Known By,

Responsibility Lecturer

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.

Cocaine (a central nerveus

system stimulant obtained

from the laeves of the coca

plant).

N

O O

CH3

O

O

C 6H 5

CH3

Morphine ( an opium alkaloid, although it is an

excelent analgesic, its use is restricted because

of the potential for addiction. Heroin is the

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.

N

NN

N

O

O

CH 3

CH 3

CH 3 N

N

CH 3

N

NCl

CH 3 O

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 pro-

oxidant 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).

OH

OH

O

N

CH 3

H

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

25°C, 180 mg/mL at 80°C, and 670 mg/mL at 100°C. 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. Observation Result

1.

2.

3.

4.

5.

6.

7.

8.

9.

10.

11.

12.

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

Taken extract

Mixed with MgO suspension and

150 mL water

Vapored it

Mixtured with water 250 mL

Filtered it buchner and 2 times 125

mL water

Vapor it until 1/3 volume

Filtered with buchner

50 g tea

3 times circulation

Sample in soxlet and tea colour

isn’t concentration

12 minutes

12 minutes

12 minutes

12 minutes

10 minutes

10 minutes

10 minutes

10 minutes

8 minutes

8 minutes

Brownish black solution

Green brown solution

Until formed powder

Black solution

Black solution

Brown solution

Brown solution

13.

14.

15.

16.

17.

Filled to separating funnel + 15 ml

chloroform + shaked (5 minutes)

Taken transparant solution and

keep it calm

The solution is heated

Balanced dust if caffeine

Determine dust caffeine melting

point

Separate 3 layers :

- Brown Solution

- Brown Transparant

- Transparant solution

Transparent solution

Dust of caffeine (yellow)

0,1596 g yellow dust

196-202°C

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 ethanol’s 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, 7-

trimethylxanthyne is C8H10N8O2 with chemical structure:

N

NN

N

O

O

CH 3

CH 3

CH 3

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

it’s 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 196-202°C melting point. It was different with theory because

caffeine’s melting point was 227-202°C 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 :

NH

NH

N

H

N

H

+ 2C 2H 5OH

N

NN

H

N

CH3

O

O

CH3

(1, 3-dimethylxanthyne)

N

NN

H

N

CH3

O

O

CH 3

+ MgO + H 2O + 2CHCl 3

N

NN

N

O

O

CH 3

CH3

CH3

+ O 2 + 3Cl 2 + Mg2+

(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 :

N

NN

N

O

O

CH 3

CH 3

CH 3

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 1°C because the characteristic of pure

compound has interval of melting point as much as 1°C.