Chemistry 2

26.11.14

Separation of the benzoic acid (PhCOOH) from phenol dissolved in ethyl acetate
The mixture contains phenol (ca. 4.5 g) and benzoic acid (ca. 15 g)dissolved in 150 mL of ethyl
acetate.
Each student works with about 20 mL of the mixture.
Work-up
The mixture is treated with NaHCO3 5% (2*10 mL) in order to separate the acid (1) as sodium salt (2),
which is soluble in the water phase. The phenol does not react with dilute NaHCO3 and remains in
the organic phase (ethyl acetate).

COOH

COO-Na+
NaOH
water

The aqueous phase is separated from the organic phase containing the phenol and treated with HCl
5% until pH is about 1-2.

COO-Na+

COOH

HCl

The acid precipitates from the acidic aqueous solution and recovered by filtration. The acid is dried at
80oC and weight.

Questions:
1)
2)
3)
4)
5)
6)

What is the [PhCOOH] and [Phenol] in the mixture

How much PhCOOH did you recovered?
How much is your recovering yield?
How can you check the purity of your acid?
How can you recover the phenol from the organic phase?
How can you check the purity of the phenol?