CHM 457: Acid Base Extraction

NAME: Johan Fadli Bin Venantius

STUDENT ID: 2019461752

PARTNERS’ NAMES:

1.Muhamad Hafiz Zulkafli

2. Muhammad Imran Bin Zulkifli

DATE OF EXPERIMENT: 3/10/2019

DATE OF SUBMISSION: 11/10/2019

CLASS GROUP: AS245S2

Experiment 1: Acid-Base Extraction

Objective: To learn the concept of separating organic compounds by utilizing the concept of
acid/base chemistry so that separation can be done.

Introduction:

Extraction involves dissolving a compound or compounds either (1) from a solid into
a solvent or (2) from a solution into another solvent. A familiar example of the first case is
making a cup of tea or coffee - the soluble flavour and odour chemicals and caffeine are
extracted from the solid tea leaves or ground coffee beans into hot water (the solvent).
Insoluble plant material is left behind in the tea bag or coffee filter. An example of the second
case is an experiment that is often done in an introductory organic lab - an organic solvent is
used to extract the caffeine from an aqueous tea or coffee solution, leaving the more water-
soluble compounds behind in the aqueous solution. This in fact is how decaffeinated tea and
coffee are sometimes made.

Acid-base extraction is a procedure using sequential liquid-liquid extractions to purify

acids and bases from mixtures based on their chemical properties. Benzoic acid, C7H6O2 (or
C6H5COOH), is a colourless crystalline solid and the simplest aromatic carboxylic acid.
Benzoic acid has density of 1.23g/ml which are denser than water.

Organic acids and bases can be separated from each other and from neutral compounds by
extraction using aqueous solutions of different pH. Most organic acids (e.g., carboxylic acids)
are insoluble or slightly soluble in water, but these compounds are highly soluble in dilute
aqueous sodium hydroxide because the organic acid reacts with the base.

Thus, the acid may be selectively removed from a mixture by dissolving the mixture in an
organic solvent and then extracting the solution with dilute sodium hydroxide. The organic
acid may be recovered from the aqueous solution by acidification, which causes
precipitation, followed by filtration.
A drying agent is an inorganic salt which readily takes up water to become hydrated.

Drying agent Capacity Speed Applications

calcium chloride, CaCl2 high medium used for hydrocarbons
calcium sulfate, CaSO4 low fast generally useful
(Drierite)
magnesium sulfate, MgSO4 high fast not used for very acid-sensitive
compounds
potassium carbonate, K2CO3 medium medium not for acidic compounds
sodium sulfate, Na2SO4 high slow generally useful

Of the five drying agents in the above table, magnesium sulfate is a fine powder and the rest
are of a larger particle size. Calcium chloride, magnesium sulfate, and sodium sulfate are the
three most commonly used agents.

Procedure:

1. EXTRACTION :

i. 0.24 g of an unknown sample and 0.12 g of benzoic acid was weight and placed
in a test tube.
ii. 10 mL of ether was added to the mixture and was shaked to dissolve the
mixture.
iii. The solution then transferred to the separatory funnel and 5 mL of 1 M NaOH
was added, capped tightly and the layers was mixed by swirling and shaking
about 30 minutes. Pressure was vent by titling the funnel and opening the stop
cork.
iv. It was shakes again after closed the stop cock. The mixture was leaved to stand
and allow the layers to separate. The aqueous layer was drain into the
Erlenmeyer flask and was labelled as first extraction NaOH.
v. 5 mL of the 1 M NaOH solution was added to the ether layer in the funnel and
the steps (i)-(iv) was repeated and labelled as second extraction NaOH.
 2. FILTRATION :

i. The flask was taken to the hood and by using a glass rod slowly stirring when 6
M HCI was added into each Erlenmeyer flask until the solution was acidic by
using blue litmus paper.
ii. Then, the flask was taken to cool in an ice bath for about 15 minutes or until
thoroughly chilled.
iii. The solid benzoic acid was collected using Buchner funnel and filter flask.
iv. 2-3 mL water was used to wash and allowing the suction to continue for five
minutes to get solid as dry as possible
v. It was scrapped gently into a watch glass and was put into an oven for complete
dryness.
vi. The solid was weight and obtain melting point

3. REMOVE NaOH :

i. 5 mL of saturated solution of sodium chloride was added to the ether layer in

separatory funnel to remove any trace of NaOH solution.
ii. The layer was separated like before, capped, mixed and vent.
iii. The ether layer was transfer into and Erlenmeyer flask and 1 g of anhydrous
sodium sulphate was added to remove the moisture inside.
iv. The stop cork was closed and swirled and was leaved to stand for 10 minutes
v. While the ether layer was drying, a small beaker or Erlenmeyer was weighted.
vi. The dried ether layer was transfer using a Pasteur filter pipet into a beaker. The
beaker then brought to a steam bath in the fume hood to evaporate the ether.
vii. After evaporated, the beaker was cooled down at room temperature and
reweighing to determine the yield of two unknown sample.

The melting point was obtained and compared to the two chemicals given
 5 mL of saturated solution of sodium chloride is added to the ether layer in
separatory funnel. To let the layer separate as before it is capped, mixed and vented. Ether
layer is transferred into a flask and 1g of anhydrous magnesium sulphate is added to remove
moisture. The flask is corked and it is swirled and let it stand for 10 minutes.

While the ether layer is drying, a small dry beaker is weighed. The dried ether layer is
transferred to the beaker with a clean Pasteur filter pipet. The ether is carefully evaporated
on a steam bath in the fume hood. Then the beaker is cooled at room temperature, it is dried
and reweighed to determine our yield of unknown sample. The unknown compound is
scraped and the melting point of the unknown compound is obtained. The melting point is
then compared with the two melting points of the two chemicals given. Unknown neutral
compound determined. Percent recovery calculated by assuming that exactly half of the
original mixture was the unknown neutral compound.

Result :

Actual weight of unknown 0.2402

Weight of unknown recovered 0.1926

Melting point of unknown 168 oC

Color White

Calculation:
Actual weight of benzoic acid 0.1230
Benzoic acid:-
Weight of benzoic acid recovered
Filter paper: 2 pieces x 0.341g =
-Before drying
0.682g
-After drying 1.897g
0.091g Watch glass: 42.867g
Melting point of benzoic acid 163 oC
Extraction NaOH (before drying) =
Color Light Pink
45.446g – 43.549g = 1.897g

Extraction NaOH (after drying) =

43.640g – 43.549g = 0.091g

Percent of benzoic acid recovered = (recovered weight / actual weight) x 100

 = (0.091g / 0.1230g) x 100

= 73.98%

Unknown Sample:-

Flask: 46.7520g

Flask + Unknown sample: 46.943g

Unknown = 46.9446g – 46.7520g

= 0.1926g

Percent of Unknown recovered = (recovered weight / actual weight) x 100

= (0.1926g / 0.2402g) x 100

= 80.18%

Melting point: 168 oC

Discussion:

In this experiment we have determined the melting point of an unknown sample

which is 168 oC. From the data we have observed that the melting point of the unknown
sample is at the range of triphenylmethanol. However, it is slightly higher than the literature
temperature of the triphenylmethane, which is 163 oC. It maybe caused by the water and
ether is not fully removed from the sample where it may affect the melting point of the
unknown sample.

From the calculation, we have got the percentage of recovered benzoic acid and
unknown which are 73.98% and 80.18% respectively which maybe caused by the solution is
not fully extracted with NaOH or the extraction was not fully in acidic condition when we let it
to cool. If benzoic acid and water are not fully separated by NaOH then it there maybe some
residue of benzoic acid left. So, the extraction of NaOH is not fully recrystalize.

It is also same with the tryphenylmethyl solution. It maybe due to some factors where
the drying agent that is anhydrous sodium sulfate was not fully absorbed the water contains.
Mean that although the ether was fully vaporized, there still water remain which cannot be
evaporate along with the ether, this is because water have higher boiling point than ether
(35oC).

The colour solution of solution for the extraction of NaOH is pink, same with the
crystal. This is due to the effect of the litmus paper but iit will not affect the recrystallization
process. Triphenylmethanol (also known as triphenylcarbinol) is an aromatic organic
compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but
well soluble in ethanol, diethyl ether and benzene. It has density of 1.199g/cm3.

Conclusion:

We have studied the extraction and vacuum filtration technique, which is important. From the
result we have obtained, there are 73.98% of recovered benzoic acid and 80.18% of
recovered unknown solution. We identify the unknown solution by comparing the melting
point we obtained with the literature melting, the unknown solution is Triphenylmethane
References:

1. CUBoulder Organic Chemistry Undergraduate Courses – Drying Organic Solutions.

Retrieved on January, 17 2010 from
http://orgchem.colorado.edu/dryingorganicsolution
2. Acid and Base Extraction Retrieved on June, 6 2019 from
https://chem.libretexts.org/Ancillary_Materials/Demos%2C_Techniques
%2C_and_Experiments/General_Lab_Techniques/Acid-Base_Extraction
Questions:

1. List four water-immiscible liquids other than ether that could be used to extract
organic compounds from equeous solution.
i. Methylene Chloride (dichloromethane)
ii. Chloroform(trichloromethane)
iii. Carbon tetrachloride (tetrachloro-methane)
iv. Cyclohexane

2. Why is it wrong to leave a bottle of anhydrous sodium sulfate or calcium chloride

open?
The air contain of water, when open the bottle of anhydrous, it expose the anhydrous
to absorb the water particles in the air, this will affect the anhydrous effectiveness
during experiment.

3. Draw the structure of the product when benzoic acid reacts with sodium hydroxide.
Why is the product of this reaction easily extracted into H 2O, while the original
benzoic acid is not so easily extracted into H2O?

This is because the stronger OH-, removes a hydrogen H+ to form a salt, the polar
salt is soluble in aqueous solution, both OH- and benzoate are bases, the stronger
base takes H+ from the weaker base.

4. Why does benzoic acid precipitate out when the aqueous layer is acidified with HCl?
Because the benzoic ion is stronger bases than Cl-, so each one takes H+ from HCl,
the acid forms are not water soluble, so they precipitate out from solution.
 5. Develop a procedure for isolating a neutral compound from a mixture containing a
basic impurity by drawing a flow chart as on page 20.

Benzoic acid and triphenylmethane

Ether
p-chloroaniline

naphthalene

Extract with HCl ( 2 times)

Combined water
layers naphthalene

trace of HCl Amine hydrochloride

salt

Extract with water

add concentrated
NaOH
p-chloroaniline
water ether
Small amount (solid)
of HCl naphthalene

(discard) (discard)
Dry (sodium sulfate)
evaporate
naphthalene