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Theory

Equilibrium Distribution of Solute Between immiscible Solvent

Extractions are widely used and are relatively simple processes. Liquid-liquid extraction
involves the distribution, or partitioning, of a solute between two immiscible liquid phases.
Usually water and an organic solvent immiscible with water are the two phases.

The distribution (transfer) of a substance between two immiscible phases is the basis of
extraction. To cause a substance to transfer from one liquid into the other at a practical rate,
you must shake the immiscible liquids together. The most complete transfer you can hope
for is one in which an equilibrium is established. At equilibrium, no further transfer can
occur, and the ratio of concentrations (solubility, g/mL) of the solute in each layer is
constant. The ratio of the concentrations is known as the distribution, or partition
coefficient, KD, and is an equilibrium constant with a certain value for a give substance, pair
of solvents, and temperature. The constant, K D, for the given equilibrium is defined
mathematically, by C1 (solute in water) <==> C2 (solute in organic solvent)C1 and C2 are
concentrations in grams per litre or grams per millilitre of solute in solvent 1 and solvent 2.
The equilibrium concentration of solute, C 2 (right side of equation) appear in the numerator.
The equilibrium concentration of solute, C1 (left side of equation) appear in the
denominator. It is important to keep in mind that K D is meaningless unless accompanied by a
chemical equation. The usual assumption is that the concentration in the organic phase is
the numerator of the KD expression; therefore, KD is equal to an organic/water partition
coefficient.

The goal of this experiment is to determine the partition coefficient for benzoic acid under
two separate extraction procedures given in parts A and B. Dichloromethane (CH 2Cl2, also
called methylene chloride) is the organic solvent for both extractions. The extraction of a
compound, such as benzoic acid, which is slightly soluble in water yet very soluble in
dichloromethane, is an equilibrium processed governed by the solubility of the carboxylic
acid in the two solvents. In Part A procedures, the extraction of benzoic acid in water and
dichloromethane will be conducted. In part B procedures, conditions of the extraction of
benzoic acid will be changed making the water layer basic (pH>7) by substituting water with
aqueous sodium hydroxide. Under the conditions in part B, the sodium hydroxide in the
aqueous layer will react with benzoic acid to form sodium benzoate ion which is very soluble
in water yet slightly soluble in dichloromethane.

CO2H (s) + NaOH (aq) -----> CO2Na (aq) + H2O (l)

Procedure
Benzene-Water system
Three different concentration of the same volume were measured out, namely 50 ml of 0.50
mol dm-3, 0.25 mol dm-3, 0.125 mol dm-3, 0.0625 mol dm-3 acetic acid solution into separate
funnels and 50 ml benzene added to each. The separating funnel was stoppered and was
shaken well for 20 seconds. Then it was inverted and the tap was opened so as to relieve the
pressure inside, and then it was allowed to separate for five minutes. The process was
repeated three times and then it was allowed for 20 minutes for equilibrium.
The equilibrium was established, the two portions of the benzene were withdrawn for
titration. The two portions were titrated against a 0.05 base. The quantities that were
titrated were varying with initial concentrations for 0.5 mol dm -3 acid sample used 10 ml
portions, for the remaining solutions 20 ml portions were the best. The aqueous solution
was also titrated.
For the multiple extraction of benzene with water, 250 dm3 of 0.5 mol dm-3 acetic acid in
benzene was prepared by calculating the volume of the acetic acid and then mixed it with
benzene. The two portions of 75 ml of each were transferred into the separating funnels.
Into one 75 ml of water was added, that was the single batch extraction experiment. It was
shaken well and the proceeded as above. At equilibrium three 20 ml portions of water from
the aqueous layer were titrated against the 0.5 mol dm-3 base.
Into the second separating funnel 25 ml of distilled water was added and the pressure was
relieved was as before. The aqueous layer was drained into a 400 ml beaker. Another 25 ml
water was added into the funnel and the process was repeated, the aqueous layer was
drained into the first portion. The process with the last 25 ml portion of water was repeated.
The three 20 ml portions of the aqueous portion were titrated against the o.50 mol dm -3.

Treatment of the results


Benzene layer 20 ml portion of 0.5 mol dm-3 titration volumes

Initial volume (ml) Final volume ( ml) Volume obtained( ml) Colour
0 3.5 3.5 pink
3.5 3.8 0.3 Light pink
Benzene layer 20 ml portion of 0.25 mol dm-3 titration volumes

Initial Volume (mL) Final Volume (mL) Volume obtained (mL) Colour
0 1.5 1.5 Pink
1.5 2.5 1.00 Light pink

Benzene layer 20 ml portion of 0.125 mol dm-3 titration volumes

Initial volume(ml) Final Volume(ml) Volume obtained(ml) Colour


0 0.6 0.6 pink
0.6 1.4 0.8 pink

Benzene layer 20 ml portion of 0.0625 mol dm-3 titrations volumes

Initial Volume (ml) Final Volume(ml) Volume obtained (ml) Colour


0 0.2 0.2 Light pink
0.2 2.1 1.9 Light pink

Aqueous layer 10 ml portion of 0.50 mol dm-3 titration volume

Initial volume(ml) Final volume(ml) Colour


0 10.8 colourless

1. (a) given [NaOH] = 1. 0237 M


NaOH(aq) + KHP(aq) = H2O(L) + KNaKHP(aq)
Ratio 1 ; 1 ; 1 ; 1
Hence [KHP] = [NaOH] = 1.0237 M
(b) s

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