Lab3 PPT Extraction

Extraction of
Caffeine
SCC 251 Organic Chemistry I, Fall
2021, LaGuardia Community
College, NYC
Week 3, Lab 3
Chemical
formula of
Caffeine
Introduction
 The active ingredient that makes tea and coffee valuable to humans
is caffeine.
 Caffeine is an alkaloid, a class of naturally occurring compounds
containing nitrogen and having the properties of an organic amine
base.
 Caffeine is found in over 60 plant species. Caffeine belongs to a
family of naturally occurring compounds known as xanthines. The
xanthines, which come from plants, are possibly the oldest known
stimulants.
 Caffeine is the most powerful xanthine in its ability to increase
alertness, put off sleep and to increase the capacity for thinking.
 Caffeine is a vasodilator (relaxes the blood vessels) as well as a
diuretic (increases urination).
 Caffeine does not exist alone in tealeaves; the leaves are mainly
cellulose, pigments and chlorophylls, and tannins. Tannins are
phenolic compounds of high molecular weight. The acidic phenols
of tannins can complex with metals like calcium to form solid
precipitates.
Sources of caffeine
 plant sources:
 coffee and cocoa beans
 tea leaves
 kola nuts
While coffee and tea are both popular products
containing caffeine, the amounts vary widely in
a single serving.
Caffeine has a slightly bitter flavor. As a result,
decaffeinating coffee beans and tea leaves will
leave the flavor slightly changed even if no
other compounds are lost Much of the flavor of
coffee and tea comes from tannins and other
flavoring agents.
Alkaloids
 Caffeine (C8H10N4O2) is an alkaloid. Alkaloids are
bitter tasting, natural nitrogen-containing
compounds found in plants.
 Alkaloids are often found to have potent
physiological activity. Examples are morphine,
heroin, lysergic acid (LSD), cocaine, quinine,
strychnine, and nicotine.
 The basic property of alkaloids come from the lone
pair of electrons found on at least one nitrogen.
The basic N in caffeine can be used to increase or
decrease its water solubility.
 Acidic conditions will form the conjugate acid salt
giving caffeine increased water solubility as a
cation. On the other hand if caffeine is in a basic
environment it takes the neutral form and is only
somewhat polar.
Extraction: Extraction is a technique commonly used in organic chemistry to
separate a wanted material from those unwanted.
In order to successfully extract any substance from one solvent into another, we must maximize differences in
solubility.
• Adding NaCl to the caffeine in water solution: The water will be more attracted to the very polar NaCl and less
attracted to caffeine thus “salting out” the caffeine from water solution.
• Adding Ca(OH)2 or CaCO3 to a caffeine in water solution: This makes the solution basic so puts caffeine in its
least polar form and so more readily solvated in organic solvents and less attracted to water.
 The water solution contains much more than just caffeine, and some of these compounds are also soluble in
organic solvents. Basic Ca(OH)2 reacts with tannic acids to form insoluble tannin salts which precipitate and so
can be removed from the solution before the caffeine is extracted.
Distillations
Techniques
Reflux
This is called
the Soxhlet
Extraction
Technique: Rotary Vacuum evaporator
Procedure
Reagents Required:
• Dichloromethane.
• Anhydrous sodium sulfite.
• Distilled water
Materials Required:
• Tea bags.
• Beaker (500ml).
• Hot plate.
• Separating funnel.
• Melting point apparatus.
• Tea bags are used as the
source of caffeine for this
experiment.
• Take 5 tea bags and record
the weight of these tea bags.
• Take 500 ml beaker add 200
ml of distilled water to it. Now
place the 5 tea bags in this
beaker.
• Boil the contents in the
beaker vigorously using a hot
plate.
Allow the mixture to cool for 5 minutes and then decant the
mixture into another beaker.
Gently squeeze the tea bags to liberate the rest of the water.
Cool the aqueous solution to near room temperature.
Continue cooling in an ice box, the tea must be cool (20° C)
before coming in contact with dichloromethane (boiling point =
40° C).
Extract the solution three times with 30-mL portions of
dichloromethane (CH2Cl2). Do not get dichloromethane on your
hands.

Extraction step:
 a. The tea solution is poured into a separating funnel and

20ml of dichloromethane is added to it. The mixture will
separate into two layers - the top layer is the tea layer and
bottom layer is the dichloromethane since it is denser than
tea.
 b. Remove the funnel from the stand and keep your fingers on
the stopper and carefully shake the separating funnel.
 c. Vent the separating funnel periodically (every 30 sec) to
relieve vapour pressure created inside the funnel
 d. When the contents have been sufficiently shaken place the
separating funnel back on the ring stand and let the two layers
separate.
 e. Drain the bottom layer into a conical flask because now the
caffeine is extracted into the dichloromethane layer. Cover the
mouth of the conical flask to avoid evaporation of solution
 f. Repeat steps a) through e) twice.
Extraction
Decant the
dichloromethane into a
conical flask (100ml).
Evaporate the
dichloromethane solvent in
a hot water bath.
When all the solvent is
removed you observe a
residue of yellowish green -
white crystalline caffeine.
Purification of Caffeine
 Obtain 0.35 g caffeine and place in small Erlenmeyer flask.
 Add 20 mL of distilled water and try to dissolve the caffeine. You might need to heat the mixture
slightly to dissolve all the caffeine
 Transfer the solution to a separatory funnel
 Add 10 ml methylene chloride to the separatory funnel supported in an iron ring and make sure the
funnel is closed
 The solvent with higher density will be the lower layer
 The aqueous layer will be the top layer
 Complete as before.
Purification procedure
Obtain 0.35 g caffeine and place in small Erlenmeyer flask.
Add 20 mL of distilled water and try to dissolve the caffeine.

You might need to heat the mixture slightly to dissolve all the
caffeine
Transfer the solution to a separatory funnel
Add 10 ml methylene chloride to the separatory funnel

supported in an iron ring and make sure the funnel is closed
The solvent with higher density will be the lower layer
The aqueous layer will be the top layer
Complete as before.
Thank you

Lab3 PPT Extraction

Uploaded by

Copyright:

Available Formats

Lab3 PPT Extraction

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Lab3 PPT Extraction

Uploaded by

Copyright:

Available Formats

Extraction of

 a. The tea solution is poured into a separating funnel and

 Obtain 0.35 g caffeine and place in small Erlenmeyer flask.

slightly to dissolve all the caffeine

 Transfer the solution to a separatory funnel

 The solvent with higher density will be the lower layer

 The aqueous layer will be the top layer

Obtain 0.35 g caffeine and place in small Erlenmeyer flask.

Add 20 mL of distilled water and try to dissolve the caffeine.

Transfer the solution to a separatory funnel

Add 10 ml methylene chloride to the separatory funnel

The solvent with higher density will be the lower layer

The aqueous layer will be the top layer

You might also like