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EXPERIMENT TITLE
II.
EXPERIMENT DATE
III.
IV.
EXPERIMENT PURPOSE
V.
BASIC THEORY
A. Extraction
Crystallization, purification, and isolation (may only be restricted to a solid)
are insufficient ways to separate mixtures of compounds. Extraction is the recovery
of a substance from a mixture by bringing it into contact with a solvent, which
dissolves the desired material. Partitioning is the separation between two distinct
phases (immiscible liquids) and also called fractional separation.
Like recrystallization and distillation, extraction is a separation technique
frequently employed in the laboratory to isolate one or more components from a
mixture. Unlike recrystallization and distillation, it does not yield a pure product;
thus, the former techniques may be required to purify a product isolated by
extraction. In the technical sense extraction is based on the principle of the
equilibrium distribution of a substance (solute) between two immiscible phases, one
of which is usually a solvent. The solvent need not be a pure liquid but may be a
mixture of several solvents or a solution of some chemical reagent that will react
with one or more components of the mixture being extracted to form a new
substance soluble in the solution. The material being extracted may be a liquid, a
solid, or a mixture of these. Extraction is a very general, highly versatile technique
that is of great value not only in the laboratory but also in everyday life. Extraction
is a convenient method for separating an organic substance from a mixture, such as
an aqueous reaction mixture or a steam distillate. The extraction solvent is usually a
volatile organic liquid that can be removed by evaporation after the desired
component has been extracted.
The extraction technique is based on the fact that if a substance is insoluble
to some extent in two immiscible liquids, it can be transferred from one liquid to the
other by shaking it together with the two liquids. For example, acetanilide is partly
soluble in both water and ethyl ether. If a solution of acetanilide in water is shaken
with a portion of ethyl ether (which is immiscible with water), some of the
Fractional Distillation
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acetanilide will be transferred to the ether layer. The ether layer, being less dense
than water, separates out above the water layer and can be removed and replaced
with another portion of ether. When this in turn is shaken with the aqueous solution,
more acetanilide passes into the new ether layer. This new layer can be removed and
combined with the first. By repeating this process enough times, virtually all of the
acetanilide can be transferred from the water to the ether.
As we stated above, the substance being extracted may be a solid.
Extractions of this type will not be conducted here, but they are probably already a
part of your own experience. The brewing of tea from tea leaves (or the tea bag that
combines extraction and filtration) and of coffee from the ground bean are excellent
examples of the extraction of a solid mixture with a hot solvent (water).
B. Coefficient Distribution (KD)
In the laboratory one of the more important applications of the extraction
process has been its use to remove an organic compound from a solution when
distillation is not feasible. Extraction is accomplished by shaking the solution in a
separatory funnel with a second solvent that is immiscible with the one in which the
compound is dissolved, but dissolves the compound more readily. Two liquid layers
are formed, and the layer that has most of the desired product in it can be separated
from the other. Sometimes not the entire product is extracted in a single operation
and the process must be repeated once or twice more to assure a clean separation. It
has been found that when two immiscible solvents are shaken together, the solute
distributes itself between them in a ratio roughly proportional to its solubility in
each. The ratio of the concentration of the solute in each solvent at equilibrium is a
constant called the distribution ratio(d) or partition coefficient (K ).
The larger the value of Kd, the more solute will be transferred to the ether
with each extraction, and the fewer portions of ether will be required for essentially
complete removal of the solute.
[
[
]
]
,where o and aq refer to the organic (ether) and aqueous layers, respectively,
and Wo and Waq are the weights in grams of material dissolved in each respective
layer. Co = concentration of organic solution and Caq = concentration of aqueous
solution.
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C. Separatory Funnel
A separatory funnel is used to separate immiscible liquids. When two
immiscible liquids are placed in a separatory funnel, two layers are seen. The denser
solvent will be the bottom layer. Most halogenated solvents are denser than water,
most non-halogenated solvents are less dense than water. If you are not sure which
layer is which, add a drop of water and see which layer it joins.
The following is an example in which iodine (I 2) in being extracted from an
aqueous solution into dichloromethane (methylene chloride). Iodine, while slightly
soluble in aqueous solutions, is more soluble in dichloromethane. Therefore, when
aqueous solution containing iodine is placed in contact with dichloromethane, the
iodine migrates into (is extracted by) the dichloromethane layer. Iodine in an aqueous
solution appears brown. Dichloromethane is a colorless liquid. Since dichloromethane
is a volatile solvent, this extraction should be done in a hood. The performing is
shown below:
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D. Titration
Iodine in water solutions is usually colored strong enough so that its presence can be
detected visually. However, close to the end point, when the iodine concentration is
very low, its yellowish color is very pale and can be easily overlooked. Thus for the
end point detection starch solutions are used. Iodine gets adsorbed on the starch
molecule surface and product of adsorption has strong, blue color. Exact mechanism
behind adsorption and color change is not known, see for example this explanation of
starch as an indicator usage. In the presence of small amounts of iodine adsorption
and desorption are fast and reversible. However, when the concentration of iodine is
high, it gets bonded with starch relatively strong, and desorption becomes slow, which
makes detection of the end point relatively difficult. Luckily high concentrations of
iodine are easily visible, so if we are using thiosulfate to titrate solution that initially
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contains high iodine concentration, we can titrate till the solution gets pale and add
starch close to the end point. In the case of titration with iodine solution we can add
starch at the very beginning, as high iodine concentrations are not possible before we
are long past the end point. At the elevated temperatures adsorption of the iodine on
the starch surface decreases, so titrations should be done in the cold.
VI.
B. Materials
Iodium 0,1 M
Chloroform p.a
Starch solution
H2SO4(aq)
Aquades
Na2S2O3 0,01M
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VII.
FLOW CHART
I.
10 mL Iodium 0,01 M
-Put into volumetric flask
II.
10 mL Iodium
-Move into separated funnel
Separated
Organic layers
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Water layers
Page 6
III.
Water layers
KD Iod
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VIII.
DATA OF EXPERIMENT
No.
Procedure
Data of Experiment
Before
After
Conclusion
non polar
Iodine can
solution, non-
extract in
I2+water = yellowish
organic solvent,
brown
polar, like
namely
I2+CH3Cl two
dissolve like
chloroform.
layer = orangish
Reaction
brown
I2+H2O
3I2(aq) +
2CH3Cl(aq)
organic layer-
2CH3I3(aq)
bottom layer )
+3Cl2(aq)
10 mL Iodium 0,01 M
-Put into volumetric flask
Solute with water until Volume was 100 mL
I2 =
yellowish
brown
1.
Hypothesis/Rea
ctions
I2 and CH3Cl is
100 mL Iodium
Water =
colorless
CH3Cl =
10 mL Iodium
colorless
That proven by
two layer
(water layer-
-Repeat
Forming two
layers2-5 times
Separated
2.
Organic layers
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Water layers
Page 8
colorless
Na2S2O3 =
Na2S2O3 colorless
colorless
Volume Na2S2O3
Starch
needed =
solution =
V1 = 3,7 mL
V2= 3,8 mL
V3 = 3,5 mL
Kd first titration =
2,86
KD first titration =
2,86
KD second titration =
3,14
KD third titration =
3,14
KD average =
Water layer
= orangish
Water layers
brown
H2SO4 =
-Added 4 mL of H2SO4 2M
-Titrate with Na2S2O3 0,001M
3.
colorless
Blue color disappear
-Determine initial
concentration of Iodium
- Repeat three times
KD Iod
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Coefficient
distribution
Iodine (KD) is 3
Page 9
IX.
EXPLANATION
This experiment is have purpose to extract iodine in organic solvent. First, is to
determine mole of iodine as of standard solutions. In determining mole iodine standard
solution , the first step that done is take 10 mL of iodine solution 0,1 M reddish brown ,
then the solution diluted with aquadest use volumetric flask 100 mL and have result
reddish brown color solution.The reaction that occur is
I2(aq) + H2O(l) no reaction occur
After a solution of iodine obtained, the results of dilution is taken as many as 10
mL using volumetric pippette and then in put into erlenmeyer .After that added 2 mL
H2SO4 2M that will make change color become brownish orange. The role of H 2SO4
added is because in iodometric titrations are carried out in strongly acid media, a situation
that promotes the reaction between oxidizing agents and iodide, and also H 2SO4 is a
strong acid and will deliver H+ which will help to proceed the reaction much faster or as a
catalyst. Then added 1 mL starch solution 2 % , and undergo a change colors become
purpleish black. Starch solution is added as an indicators for titration, when starch is
mixed with iodine in water, an intensely colored starch/iodine complex is formed. Many
of the details of the reaction are still unknown. The iodine/starch complex has energy
level spacings that are just so for absorbing visible light - giving the complex its intense
blue color. The complex is very useful for indicating redox titrations, when there is
excess oxidizing agent, the complex is blue; when there is excess reducing agent, the I 5breaks up into iodine and iodide and the color disappears. After that a solution is titrate
using Na2S2O3 0,01 M . The reaction that occur is
I2 + 2e-
2I-
2 S2O3 2-
S4O62- + 2e-
I2 + 2 S2O3 2-
2I- + S4O6 2-
Based on the theory, the end point of I 2 is changing color became colorless. From
theory we know that the color is shown in the picture below (left picture) and our
experiment (right picture). We can assume that based on the theory our end point is right.
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Our Experiment
Theory
Color I2solution +
Color at end
Color I2solution +
Color at end
H2SO4 + Starch
Point
H2SO4 + Starch
Point
In this titration, obtained changing color solution become colorless at the volume
of titrant Na2S2O3 is 9 mL. By knowing the volume of Na2S2O3 that needed , it can use to
find out a mole from I2 by calculation below:
Based on the calculation mole Iodine as standard is 0,045 mmol. Which will be
used to acquire mmol I2 organic in phase, to determine coefficient distribution of Iodine.
Second steps is to extract iodine, by using a water solvents and organic solvents
that in this experiment using chloroform . Using chloroform to extract because, iodine is
a non-polar molecule this has a weak interaction with the hydrogen bonded water
molecules. The energy associated with the iodine/ water interactions is not enough to
compensate for the lost energy of the water/water interactions. This ultimately means that
not much iodine will dissolve in water. If a solvent with weaker solvent/solvent
interactions than water were introduced to this system, iodine would find it easier to
disrupt these interactions and insert itself (dissolve) between the solvent molecules,
cyclohexane or chloroform are such solvents. They have no hydrogen bonding and are
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only very slightly polar. Energywise, it is more favorable for the iodine to dissolve in the
non-polar solvent than in the water, so it exists preferentially (but not totally, an
equilibrium will exist) in the non-polar solvent. The release of energy as the iodine
switches solvents is partially responsible for the initial build up of pressure in the
separatory funnel, so two layers are produced when the two solvents are added together.
In short Iodine, is slightly soluble in aqueous solutions, is more soluble in
dichloromethane. Therefore, when aqueous solution containing iodine is placed in contact
with dichloromethane, the iodine migrates into (is extracted by) the dichloromethane
layer. The first step that done is take 10 mL of I 2 solution 0,1 M brownish orange .Then
diluted with aquadest on volumetric flask 100 mL . After diluted , take solution of the
results of dilution with using volumetric pipette 10 mL and poured into separating funnel.
The reaction occur is
I2(aq) + H2O(l) no reaction occur
After that added chloroform solution 5 mL as an organic solvent and shake 2-5
times until two layer separated perfectly. That was obtained two layers, upper layer is
water layer brownish orange and bottom layer is organic layer purple. The reaction that
occur is
3I2(aq) + 2CHCl3(aq) 2CHCl3(aq) + 3Cl2(g)
After that separate organic layer with take out into beaker glass, it do repeatedly
until all the organic layer are strictly separated entirely. Based on the theory, when
aqueous solution containing iodine is placed in contact with dichloromethane, the iodine
migrates into (is extracted by) the dichloromethane layer. Iodine in an aqueous solution
appears brown. From theory we know that the color is shown in the picture below (left
picture) and our experiment (right picture). We can assume that based on the theory our
result is right
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Theory
Our Experiment
Color of layer
Color of layer
when Iodine
already wholly
when Iodine
already wholly
extracted with
separated
extracted with
separated
The water layer moved into erlenmeyer .After moved into erlenmeyer added 2 mL
H2SO4 2M. The role of H2SO4 added is because in iodometric titrations are carried out in
strongly acid media, a situation that promotes the reaction between oxidizing agents and
iodide, and also H2SO4 is a strong acid and will deliver H+ which will help to proceed the
reaction much faster or as a catalyst. And then added 1 mL starch solution 2 % that make
changing color to blackish blue. Starch solution is added as an indicators for titration,
when starch is mixed with iodine in water, an intensely colored starch/iodine complex is
formed. Many of the details of the reaction are still unknown. The iodine/starch complex
has energy level spacings that are just so for absorbing visible light - giving the complex
its intense blue color. The complex is very useful for indicating redox titrations, when
there is excess oxidizing agent, the complex is blue; when there is excess reducing agent,
the I5- breaks up into iodine and iodide and the color disappears. Titrate solution using
Na2S2O3 0,01M. The reaction that occur is
I2 + 2e-
2I-
2 S2O3 2-
S4O62- + 2e-
I2 + 2 S2O3 2-
2I- + S4O6 2-
Extraction iodine do 3 times, which also continue with the titration repeated 3
times to get valid results. Based on the theory, the end point of I 2 is changing color
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became colorless. From theory we know that the color is shown in the picture below (left
picture) and our experiment (right picture). We can assume that based on the theory our
end point is right.
Theory
Color
Color at end
Color
Color at end
I2solution +
Point
I2solution +
Point
H2SO4 +
H2SO4 +
Color
Color at end
Color
Color at end
I2solution +
Point
I2solution +
Point
H2SO4 +
H2SO4 +
In first titration, volume of Na2S2O3 needed when solution change from purpleish
black to colorless is 3,7 mL. With known volume of Na2S2O3 in titrations, we can
calculate coefficient distribution iodine, the calculation below:
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( )
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Coefficient distribution (KD) iodine in third titration based on the calculation is 3,14.
Based on the calculation that have been gained above the value of KD on each titration
the value of KD iodine average is 3.
X.
DISCUSSION
From the results that we obtained, the value of coefficient distribution of iodine equal
to 3 it is deviated from the theory. While value of coefficient distribution of iodine from
theory is 10. This may due to some of the errors or mistakes have been occurred during the
experiment. First and foremost is, iodine solution that we use in experiment is maybe has
contaminant so it can affect the end point of titration, so the volume of Na2S2O3 that needed
for determine mole of I2 is
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XI.
CONCLUSION
From this experiment we conclude that; first Iodine can extract in organic
solvent, namely chloroform, that proven by two layer of organic layer(bottom) and
water layer (upper)that formed. Second, the coefficient distribution (KD) Iodine is 3.
XII.
2.
3.
weak base that ionize in water solvent and not react in organic solvent?
5.
Prove that with multiple extraction will have increases percent result,
Its mean that the only reaction affecting extraction efficiency is the
We can assume that the solute is initially present in the aqueous phase and that
we are extracting it into the organic phase. A conservation of mass requires
that the moles of solute initially present in the aqueous phase equal the
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combined moles of solute in the aqueous phase and the organic phase after the
extraction.
3.
HA, by an organic phase in which ionic species are not soluble. In this case
the partition coefficient and the distribution ratio are
Although the weak acid is soluble in both phases, its conjugate weak base, A,
is soluble only in the aqueous phase. The Ka reaction, which is called a
secondary equilibrium reaction, affects the extraction efficiency because it
controls the relative abundance of HA in solution.
4.
Because the weak base exists in two forms, only one of which extracts
into the organic phase, the partition coefficient, KD, and the distribution ratio,
D, are not identical.
For the concentration of HB+ and substitute back into the equation for D,
obtaining
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5.
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REFERENCES
Mengetahui,
Dosen/Asisten/Pembimbing,
Praktikan,
(.)
()
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Page 20
ATTACHMENT
color
yellowish brown
funnel
colorless
chloroform
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Page 21
purple solution
funnel
Separated again
Fractional Distillation
Pouring to Erlenmeyer
Page 22
with H2SO4
Na2S2O3(aq) 0,01M,
Initial scale
Final scale
colorless solution
0,01M
was 0 mL
was 3,7 mL
solution
Fractional Distillation
Page 23
Initial scale
Final scale
0,01M
was 5 mL
was 8,8mL
become colorless
solution
Initial scale
0,01M
was 9 mL
12,5 mL
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Page 24
0,01M
solution
13 mL
mL
become colorless
solution
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Page 25
CALCULATION
Reaction :
I2+ 2e -
2I-
2S2O32-
S4O6+ 4e- x 1
x2
= 0,01 N
V Na2S2O3
= 9 mL
mmolek I2
= mmolek S2O32-
mmolek I2
= VS2O32-x N S2O32-
mmolek I2
= 9 mL x 0,01 N
I2
= 0,09 mmolek x
I2 standard
= 0,045 mmol
First titration
VNa2SO3
= 3,7 mL
mmolek I2
= mmolek S2O3-
mmolek I2
= V S2O3-x Na2SO32-
mmolek I2
I2
= 3,7 mL x
I2 (a )
= 0,0185 mmol
Mmol I2(0)
[I2](a)
= 0,00185
[I2](0)
= 0,0530
KD
=[
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[ ]( )
]( )
Page 26
Second Titration
VNa2SO3
= 3,8 mL
mmolek I2
= mmolek S2O3-
mmolek I2
= V S2O3-x Na2SO32-
mmolek I2
= 3,8 mL x 0,01 N
= 3,8 mL x
I2 (a )
= 0,0180 mmol
Mmol I2(0)
[I2](a)
= 0,00180
[I2](0)
KD
=[
= 0,0054
[ ]( )
]( )
Third Titration
VNa2SO3
= 3,5 mL
mmolek I2
= mmolek S2O3-
mmolek I2
= V S2O3-x Na2SO32-
mmolek I2
I2
= 0,035 mmolek x
I2 (a )
= 0,0175 mmol
Mmol I2(0)
[I2](a)
= 0,00175
[I2](0)
= 0,0055
KD
=[
KD average
Fractional Distillation
[ ]( )
]( )
=3
Page 27