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Extraction

Description

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

Have been checked by assistant and assistant coordinator

Makkassar,

December Assistant Coordinator

Assistant

Fandi Ahmad,

Known By,

Responsibility Lecturer

Ramdani,

Title of Experiment Caffeine Extraction

Purpose of Experiment Known continue extraction with heat intermediately

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

They are special interest because most are characterized by high level of biological activitity

Some examples include cocaine,

Cocaine (a central nerveus

Morphine ( an opium alkaloid,

its use is restricted because of the potential for addiction

Heroin is the O

diacitate ester of morphine) N H CH3

(Carey,

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,

Example include caffeinee (found in tea leaves,

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

Caffeine

Cl C 6H 5

Nicotine

Valium (Bruice,

2003: 884)

Caffeinee (1,

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,

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,

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,

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,

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,

1 piece j

Hot plate,

1 piece k

Separating funnel,

1 piece l

Erlenmeyer m

Balance,

1 piece n

Stirbar,

3 pieces

Rough and smooth cloth,

1 piece p

Wood clamp and spoon,

1 piece q

Boiling stone 2

Chemical a

Ethanol 96% c

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

Work Procedure 1

As many as 50,00 grams of tea is balanced

The tea is covered with filtering paper and it is bond

The tea that already (after covered) is put in soxlet and the ethanol is poured through the tea until a half of rounded flask

The extraction process is done and it is waited until obtained 10th circulation

As many as 17,5 grams of MgO suspension solved in 150 mL H2O

Let it dry when vapor

Extract the powder with boiling water 250 mL (incruicible) and suck while heat with buchner

Repeat it 3 times with boiling water 125 mL

It solution collect becone one after added 25 mL H2SO4 dilute

Vaporate until 1/3 initial volume

Extract with separating funnel with 15 mL chloroform 5 times

Chloroform is vaporated and recris if there is crystal

Test melting point to know the purity

Observation Result No

Observation

Meassured sample (tea)

50 g tea

Filled sample to filtering paper

Added ethanol to soxhlet

Set soxlet and filled

Sample in soxlet and tea colour isn’t concentration

Noted circulation 1st

12 minutes

12 minutes

12 minutes

12 minutes

10 minutes

10 minutes

10 minutes

10 minutes

8 minutes

8 minutes

Taken extract

Brownish black solution

Mixed with MgO suspension and Green brown solution 150 mL water

Vapored it

Until formed powder

Mixtured with water 250 mL

Black solution

Filtered it buchner and 2 times 125 Black solution mL water

Vapor it until 1/3 volume

Brown solution

Filtered with buchner

Brown solution

Filled to separating funnel + 15 ml Separate 3 layers : chloroform + shaked (5 minutes)

Taken transparant solution and

Transparent solution

The solution is heated

Dust of caffeine (yellow)

Balanced dust if caffeine

Determine dust caffeine melting

196-202°C

Discussion In this experiment,

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,

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,

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 : O

2C 2 H 5 OH

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

Laborant must prepare our apparatus and chemical

Assistant should be diligent to teach us about the procedure

BIBLIOGRAPHY Anshori

Organic Chemistry

Bandung: Padjadjaran University

Bruice,

Organic Chemistry 4th edition

London: Longman Valey

Caballero,

Extraction of Caffeine From Tea Leaves

USA: Dragon Alley

Organic Chemistry 4th edition

Virginia: M

Graw Hill

Olcina,

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

Ethanol used bacause it is polar compound and also caffeine could be bond with polar compound,

caffeine could be solvent in ethanol and ethanol is volatile so it will be easy to evaporated

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