Extraction of a Two Component Mixture

Purpose
The purpose of this lab is to separate a two-component mixture of benzoic
acid and acetanilide by means of simple distillation. Ethyl acetate will be the solvent
that the mixture is dissolved in and a sodium hydroxide solution will be used to
draw out the benzoic acid. Simple distillation will be used to extract the remaining
acetanilide and hydrochloric acid will be used to extract the benzoic acid.
Procedure
A weighed sample of benzoic acid and acetanilide will be put into ethyl
acetate to dissolve. This solution will be placed in a separatory funnel, where three
15mL aliquots of sodium hydroxide will be added. The solution will separate into two
different layers, the bottom layer will be drained out, this is the benzoic acid.
Hydrochloric acid is added to the benzoic acid solution and put through a vacuum
filtration apparatus in order to obtain just the benzoic acid. The remaining solution
left in the separatory funnel after the three aliquots of sodium hydroxide, will be
distilled. The distillate will be the ethyl acetate and the remaining brown liquid will
be the acetanilide. The flask containing the acetanilide will be put in an ice bath to
allow crystals to form and the final weight of both the benzoic acid and acetanilide
will be calculated.
For a fully detailed laboratory procedure, please refer to the Organic Chemistry Lab
Manual: Organic Chemistry 1 Manual, experiment #7: The extraction of a twocomponent mixture.
Reagents/Safety Information
Benzoic Acid: C7H6O2

Boiling Point 249.2 degrees C

Molecular Weight 122.12g/mole
Density 1.27g/cm3

Acetanilide: C6H5NH(COCH3)
Boiling Point 304 degrees C
Molecular Weight 135.16g/mole

Density 1.22g/cm3
Ethyl Acetate: C4H8O2

Boiling Point 77 degrees C

Molecular Weight 88.11g/mole
Density 897kg/m3

Safety:
Very concentrated hydrochloric acid and sodium hydroxide will be used in the
lab, they are irritants. If exposure or contact occurs, make sure to rinse the area
immediately with water. If exposure to the eyes occur, make sure to rinse
thoroughly up under the lid. If any further irritation occurs, seek medical aid.
The benzoic acid and acetanilide are irritants, if exposure occurs rinse the
area with water. Make sure to work in the fume hood. If a spill occurs, cover the spill
in an inert material and dispose of it in the non-halogenated waste container.
Reagents:

Benzoic Acid/Acetanilide
Ethyl Acetate
Sodium Hydroxide (NaOH)
Hydrochloric Acid (HCl)
Calcium Chloride (CaCl2)

Equipment

Analytical Balance
250mL Separatory Funnel
Graduated Cylinder
250mL Erlenmeyer Flask
Round Bottom Flask
Distillation Apparatus
Vacuum Filtration Apparatus

Reaction Equations
1) Benzoic Acid

(aq)

+ Sodium Hydroxide

(aq)

Water (L) + Sodium Benzoate

(aq)

2)

Sodium Benzoate

3)

Benzoic Acid (S)

Acetanilide (aq) + Sodium Hydroxide

(aq)

+ Hydrochloric Acid
(aq)

(aq)

Sodium Chloride

(aq)

No Reaction.

Structural Formula

Figure 1: Structural formula of benzoic acid.

Figure 2: Structural formula of acetanilide.

Observations/Data
2.5008g of the two component mixture of acetanilide and benzoic acid was
weighed out on the analytical balance. This was dissolved in 20mL of ethyl acetate,
dissolved very well/quickly in this solution. Poured this solution into a separatory
funnel. Three 15mL aliquots of sodium hydroxide was poured into the funnel. Two
separate layers were immediately formed. The bottom layer consisted of the
benzoic acid salt. When hydrochloric acid was added to the extracted benzoic acid,
a white precipitate was formed. The precipitate was vacuum filtered out and the
remaining benzoic acid was weighed at 18.4730g. The acetanilide/ethyl acetate
solution was distilled, ethyl acetate was boiled off and a light brown liquid remained
in the round bottom flask. The round bottom flask was put into an ice bath and a
white crystalline solid appeared. This final precipitate was weighed to be 1.5811g.
Weight of Round Bottom Flask: 42.2801g
Final Weight of Round Bottom Flask: 43.8612g

Final weight of Acetanilide crystals: 43.8612g 42.2801g = 1.5811g

Final weight of benzoic acid: 18.4730g
Discussion
Ethyl acetate was the solvent used to dissolve the benzoic acid/acetanilide
mixture. Both the acetanilide and benzoic acid are very soluble in the ethyl acetate.
When sodium hydroxide was added to the solution, no reaction with the acetanilide
occurred. Acetanilide has a nitrogen hydrogen bond, therefore it accepts protons,
whereas benzoic acid donates protons. The sodium hydroxide was used in order to
isolate the benzoic acid from the ethyl acetate by means of a neutralization
reaction. Since benzoic acid donates protons, it reacted with the sodium hydroxide
to create water and sodium benzoate, a compound that is soluble in water. Since
acetanilide did not react with the sodium hydroxide, and is more soluble in ethyl
acetate than it is in sodium hydroxide, it remained in the upper layer. The sodium
benzoate remained in the lower layer because it is more dense than the ethyl
acetate/acetanilide solution, allowing it to be funnelled out.
When hydrochloric acid was added to the sodium benzoate solution, the
chlorine in the acid reacted with the sodium to make sodium chloride as a by
product, and the additional hydrogen was used to recreate benzoic acid and water.
Benzoic acid is not soluble in water, so when it was reformed in solution, it was
created as a white precipitate.
When the ethyl acetate solution was distilled, it was easy to isolate the
acetanilide because of the difference in boiling points. Ethyl acetate has a much
lower boiling point than acetanilide, it has a boiling point of 77 degrees Celsius and
acetanilide has a boiling point of 304 degrees Celsius. The difference in boiling
points allowed the acetanilide to be extracted by using the distillation apparatus.
The IR spectra of the acetanilide shows a sharp nitrogen hydrogen bond at
roughly 2800 to 3000 wavelengths, and shows a carbon double bonded to an
oxygen at 1700 wavelengths. The IR spectra of the benzoic acid, there is a very
broad oxygen hydrogen bond, taking up almost 1000 wavelengths, ranging from
2300 to 3200 wavelengths. There is also a sharp peak at 1700 wavelengths which is
characteristic of a carbon double bonded to an oxygen. The differences in

wavelengths relates to the amount of energy or movement within the bonds of the
atoms. Since hydrogen is the lightest atom, there is a lot of movement within the
bonds, therefore any hydrogen bonds have the highest wavelength.
The melting point of the final benzoic acid and acetanilide could not be found
because of experimental error; there was not enough time for the isolated
compounds to be dried. Since the melting points of the compounds could not be
determined, the purity is unknown. The purity of the compounds could have been
determined by observing the sharpness and accuracy of the melting point.
Conclusion
The final weight of the benzoic acid was 18.4730g, and the final weight of the
acetanilide was 1.5811g. The melting point of the compounds could not be
determined therefore the purity of the substances is unknown.