UNIVERSITI TUNKU ABDUL RAHMAN

FACULTY OF SCIENCE

BACHELOR OF SCIENCE (HONS) BIOCHEMISTRY

YEAR 1 TRIMESTER 3

UDEC 1164 ORGANIC CHEMISTRY

Name

Sri Sangliswaran s/o Subramaniam

ID

1203776

Experiment Title

Extraction : Extraction with Acid and Alkali

Partners

Nurul Maswin bt Anaqi Suen

Tan Chai Yuin

Date of Submission

11.2.2015 (week5)

Experiment 4
Title:

Extraction; Extraction of Acid and Alkali

Objectives:

To study the extraction of acid and alkali from a mixture

To acquire the skills of extracting and separating mixtures from a solution
To determine the melting point of benzoic acid and p-dichlorobenzene through
laboratory experiment
To corroborate the percentage recovery of the benzoic acid and p-dichlorobenzene
extracted from the ether solvent and aqueous solvent.

Introduction:
Acid-base extraction is a procedure using sequential liquid-liquid extractions to purify acids
and bases from mixtures based on their chemical properties. The most important characteristic of a
solvent-solvent extraction is that the two solvent must be insoluble with one another. Thus, this will
separate the mixture of the two solvents into two layers. Mostly, water will be used as a aqueous
solution and the other will be the organic solvent. The selectivity of the organic compound must be
done with care and only volatile solvent to be used as it will ease the evaporation process to form
crystals.
The cleanest separations of organic compounds can be affected by use of acid or alkaline
solution which convert the compound to be extracted to a water soluble, ether insoluble salt.
Approximately 5% to 10% solution of sodium hydroxide, for an instance, converts acids. Phenolic
compound undergo similar salt formation with sodium hydroxide solution. Hence, a sodium
hydroxide solution is used as carboxylic acid and phenolic compound extractor from its solution in an
organic solvent, or in other words, an organic solvent can be used to remove impurities from a
carboxylic acid or phenols dissolved in aqueous sodium hydroxide.
Likewise, carboxylic acids are converted to their sodium salt by aqueous solution of sodium
bicarbonates, but it is not a sufficient alkaline to promote formation of salts of phenolic compound.
This provides an elegant methods for the separation of a carboxylic acid and a phenolic compound.
The acid may be removed from the solution in an organic solvent firstby means of extraction with
sodium bicarbonate solution and then the phenol, using the sodium hydroxide solution. Inorganic
acids are regularly removed from organic solvent by extraction with sodium hydroxide, sodium
carbonate, or sodium carbonate solution. Dilute hydrochloric acid is often used in the extraction of
basic substances from mixtures or in the removal of basic impurities. The dilute acid converts the
base such as ammonia or an organic amine (R3 N) into the water-soluble chloride salt (R 3 NH+, Cl-).
Conversely, organic impurities may be removed from amines by extraction from a dilute acid solution
with organic solvents.
Sodium salts of carboxylic acids and phenolic compounds are readily reconverted to the
parent compounds by treatment with sulphuric or phosphoric acid. The chlorides of amines revert to
the original amine upon addition of sodium hydroxide solution.

Glassware :

Separatory funnel (250 ml), Buchner funnel, capillary tubes, conical flasks, beaker (50
ml), watch glass

Materials :

benzoic acid, p-dichlorobenzene, ether, 10% Sodium Hydroxide (NaOH), concentrated

hydrochloric acid (HCl), andhydrous Calcium Chloride (CaCl2), Distilled water, litmus
paper

Procedure :
1. About 40 mL of ether was measured and poured into a separatory funnel that contains 2 g of
benzoic acid and p-dichlorobenzene mixture. Then, roughly 20mL of 10% sodium hydroxide
solution (NaOH) was added into the funnel.
2. The funnels was closed and shake well. Intermittently, the funnel was inverted and and any
surplus pressure in the funnel was released through the tap.
3. The stopper was removed and lower aqueous layer in the funnel was ran into a conical flask.
Additional 10mL of 10% NaOH was added into the separatory funnel obtain the remaining
residue and the lower aqueous layer was ran into the same conical flask.
4. Concentrated hydrochloric acid (HCl) was added drop wise until the mixture becomes acidic
and until the precipitation process ceased.
5. The ether solution in the separatory funnel was washed with distilled water and the lower
layer was discarded from the funnel.
6. Three to four granules of anhydrous calcium chloride (CaCl2) was added into the ether
solution in the separatory funnel and the mixture was shaken occasionally until the turbidity
ceased.
7. The solution then was decanted into a small clean beaker.
8. Small boiling chips was added into the beaker and was heated gently in a hot water bath until
only 15 to 20 mL of solution remained in the beaker.
9. The ether then was decanted onto a watch glass and set aside for the ether to evaporate.
10. The benzoic acid was filtered using the Buchner funnel and a flask. The filter paper then was
set aside to dry.
11. The weight and the melting point of the recovered benzoic acid was determined.
12. After the ether evaporated, the weight and the melting point of recovered p-dichlorobenzene
was determined.

Results and calculation:

Weight before separation
Mass of benzoic acid

1.00 g

Mass of p-dichlorobenzene used

1.00 g

Weight after separation

Mass of plastic container + benzoic acid crystals

1.07 g

Mass of plastic container

0.50 g

Mass of benzoic acid crystals

0.57 g

Theoretical melting point of benzoic acid crystal

122 oC

Experimental melting point of benzoic acid crystals =

120 oC

Mass of plastic container + p-dichlorobenzene

1.1047 g

Mass of plastic container

0.5231 g

Mass of p-dichlorobenzene crystals

0.5816 g
=

53 oC

Experimental melting point of p-dichlorobenzene crystals =

54 oC

Theoretical melting point of p-dichlorobenzene crystals

Percentage recovery of benzoic acid =

Weight of compound recovered

Weight of compound used

0.57g
1.00g

57 %

x 100 %

x 100 %

Percentage recovery of p-dichlorobenzene

Weight of compound recovered

Weight of compound used

0.5816 g

x 100 %

1.00g
=

58.16%

Percentage error of recovery of benzoic acid

=

weight of compound used weight of compound recovered

Weight of compound used

1.00g 0.57g

x 100 %

1.00g
=

x 100 %

43 %

Percentage error of recovery of p-dichlorobenzene

=

weight of compound used weight of compound recovered

Weight of compound used

1.00g 0.5816g
1.00g

x 100 %

41.84%

Relative accuracy of melting point of benzoic acid

=

melting point of compound recovered

melting point of pure compound

120 oC
o

122 C
=

98.36%

x 100 %

x 100 %

x 100 %

x 100 %

Relative accuracy of melting point o p-dichlorobenzene

=

melting point of compound recovered

melting point of pure compound

54 oC

x 100 %

53 oC
=

x 100 %

101.9%

Percentage error of melting point of benzoic acid

=

theoretical melting point experimental melting point

Theoretical melting point

122 oC 120oC
122 oC

x 100 %

x 100 %

1.64%

Percentage error of melting point of p-dichlorobenzene

=

experimental melting point theoretical melting point

Theoretical melting point

54 oC - 53 oC
o

53 C
=

1.89%

x 100 %

x 100 %

Discussion:
In this experiment the extraction of benzoic acid and p-dichlorobenzene was carried out in an
ether solution. Benzoic acid is a simple aromatic carboxylic acid and a colourless crystalline solid.
The p-dichlorobenzene is colorless solid with a very strong odor.[1] Below are the structural formula
and the molecular formula of benzoic acid and p-dicholorobenzene;

C6H5COOH
Benzoic acid

C6H4Cl2
p-dichlorobenzene

Organic bases and acids can be separated from each other as wella s neutral compound by extraction
using aqueous solution of different pH. Mostly, organic acids are weak acid and dissociate partially in
water, but when the molecular mass of the acid increases the acid becomes insoluble and does not
dissociate or react in presence of water, but are very soluble in organic solvents like sodium
hydroxide, NaOH solution as this is a base. This concept is applied in the extraction process, where
the acid can be selectively removed from a mixture by dissolving the mixture in an organic solvent
and then extracting the solution with dilute aqueous NaOH solution. Therefore, the organic compound
can be recovered from the aqueous solution by neutralization with concentrated hydrochloric acid,
HCl which causes precipitation and then followed by filtration to extract the precipitate.
For the extraction to occur successfully, there are some criteria for the acid and alkali to
achieve before it could produce a product. The acid and alkali only works if there is a large difference
in their solubility between their charged and uncharged form. The reaction will cease to some extend
where;
a) the acidic and basic functional groups in the same molecules are zwitterions.
b) lower amine that is miscible or significantly soluble in water at most pH
c) the acid is a very lipophilic acid and the base is an amine that do not dissolve in the aqueous phase
in their charged form
d) the acids are hydrophobic acids

The acid-base extraction technique used the theory that the salts which is ionic tend to be
water-soluble while neutral molecules tend not to be soluble. The addition of an acid to a mixture of
an organic acid and base will result in the acid remaining uncharged while the base will be
protonated. The addition of the base to a mixture of an organic acid and base will result in the base
remaining uncharged while the acid is protonated to give the corresponding salt.
When acid-base extraction was carried out, an acid or base compound that was ether soluble and
water insoluble will be changed to ether insoluble and water soluble salt. The solubility of benzoic
acid was shown below:
Carboxylic acid

Salt of carboxylic acid

-High solubility in ether

- Low solubility in ether

-Low solubility in water

- High solubility in water

Not only that, when choosing a solvent, the solvent must adapt to several criteria in order to be
accepted as an ideal solvent. Firstly, the solvent that have chosen must be immiscible in water. This is
to ensure that the solvent can be drawn out during the extraction. Secondly, the solvent must not react
chemically with the component of the mixture except in the acid and base extraction, this is very
crucial as to result in intentioned outcome rather than producing an unwanted product. Thirdly, the
solvent must be readily to be removed from the solute of the following extraction, the volatility of the
solvent plays an important role here as the solvent must be volatile in order to be eliminated during
the recovery of the precipitate. Lastly, the solvent must have a favorable distribution coefficient for
the component to be separated, this is to ensure that the solvent can react with the solute.
From the result obtained, the percentage recovery of benzoic acid and pdichlorobenzene are 57% and 58.16% respectively. Both the recovery shows lower percentage of
recovery due experimental errors done while conducting the extraction. The benzoic acid precipitate
was left to dry in open area, an amount of precipitate might have lost due to humidity of the lab.
Besides that, some of the precipitate remained in the filter paper that is hard to remove, thus
contributes to the low percentage of recovered mass. For the p-dichlorobenzene, the final extracted
liquid should be heated gently and the beaker containing the solution must be covered all time due to
the volatility of the compound, but during the heating, over heating causes some of the pdichlorobenzene evaporated and evaporation occur throughout the experiment when the beaker is not
covered. This causes the amount of p-dichlorobenzene recovered lower than the proposed amount.
The percentage error of the melting point for benzoic acid is 1.64% and for p-dichlorobenzene is
1.89%. The reason is that the melting point of recovered benzoic acid is lower than the pure benzoic
acid and the melting point of recovered p-dichlorobenzene is slightly higher than the pure compound
is because the substances that we extracted are not a pure substance due to the laboratory condition..
So the melting point of both substances was affected.

Several precautionary steps was taken into action to prevent mishap in laboratory.
While shaking the mixture of ether, benzoic acid and p-chlorobenzene with NaOH in the separatory
funnel, the tap of the funnel must be opened at several intervals to release the gas. This is essential as
this will prevent the stopper of the funnel from pooping out from the funnel and cause injuries. While
handling the concentrated HCl, all students ensured wearing gloves and safety goggles to avoid any
contact with acid and all handling of the concentrated acid are conducted in fume chamber. Not only
that, no flame was introduced near the extraction as the ether that are being extracted are volatile and
highly flammable. Maximum care was taken when transferring the precipitates from the filter paper
to the plastic container in order to transfer all the precipitate and to reduce the error.

Conclusion:
The melting point of benzoic acid and p-dichlorobenzene was determine through experimental
procedures that 120 oC and 54 oC respectively.
The percentage of recovery of benzoic acid and p-dichlorobenzene is 57% and 58.16% repectively
due to pureness of compounds are less.
The extraction of acid and alkali was studied.

Reference:
1. Solubilities of Inorganic and Organic Compounds. (1952). In Google Books. Van Naustrad.
2. Reactivity of acid and alkali. (2004). In Organic Chemistry for STPM (Vol. 2). Fajar Bakti.

1.

4.

The mixture was shake in the separatory funnel

2.

addition of acid into aqueous

solution
5

Ether

Testing with blue litmus shows

the compound is acidic

Aqueo
us
solutio

Two layer are formed

3.

6.

Aqueous
layer
collected
in a flask

The precipitate then filtered in

Buchner funnel

7.

9.

The ether then poured in watch glass

and left to dry

The precipitate then was left to dry

8.

10.

Benzoic

The ether solution was heated

p-