Вы находитесь на странице: 1из 4

Tiffany Liu

October 11, 2018


Zeynep Akgun

​ ​ Extraction of Benzoic ACid and its Conjugate Base


Experiment VI-The Partition Coefficient (K​​p​)​​ 30​
from Two Immiscible Phases​31 ​

Abstract:

This goal of this laboratory was to perform an extraction of benzoic acid through a liquid-liquid

extraction technique. In this, a solution of benzoic acid and methylene chloride was mixed with deionized

water or sodium bicarbonate. The organic layer was then gathered from each tube and separated using a

pipette. Sodium sulphate was then added to both tubes to further dry out the aqueous material remaining.

After drying, the methylene chloride was then boiled off and the benzoic acid in each tube is then

weighed. By the end of the experiment, about 51 mg of benzoic acid was left in the tube that mixed water

with the methylene chloride and benzoic acid solution and 21 mg of benzoic acid was left in the other

tube.

Reactions:

+ H​2​O(l) → +

+ → +
Procedure:

Poulos, Z. J. A Laboratory Manual for the Health Science Major: Organic Chemistry I CHE 231L;

Macmillan Learning Curriculum Solutions: Plymouth, MI, 2018; pp 101-109.

We changed all liquid additions for 600 microliters to 1000 microliters.

Data:

Mass of culture tube A: 11.483g

Mass of benzoic acid for tube A: 0.053g

Mass of culture tube and benzoic acid for tube A: 11.532g

Mass of benzoic acid recovered in tube A: 0.049g

Mass of culture tube B: 11.497g

Mass of benzoic acid for tube B: 0.051g

Mass of culture tube and benzoic acid for tube B: 11.518g

Mass of benzoic acid recovered in tube B: 0.021g

Calculations:

Tube A:

Mass of culture tube and benzoic acid for tube A - mass of culture tube = mass of benzoic acid recovered

11.532 g(11532 mg) - 11.484 g(11484 mg) = 0.049 g(48 mg)

Original mass - recovered mass = Aqueous mass

50 mg - 48 mg = 2 mg

K​p​ = ​(mg/1000μL)organic layer​ = m


​ g​organic layer​/mg​aqueous layer
(mg/1000μL)aqueous layer

K​p​ = 48 mg/2 mg = 28

Tube B:
Mass of culture tube and benzoic acid for tube B - mass of culture tube = mass of benzoic acid recovered

11.518 g(11518 mg) - 11.497 g(11497 mg) = 0.021 g(21 mg)

Original mass - recovered mass = Aqueous mass

51 mg - 21 mg = 30 mg

K​p​ = ​(mg/1000μL)organic layer​ = m


​ g​organic layer​/mg​aqueous layer
(mg/1000μL)aqueous layer

K​p​ = 21 mg/30 mg = 0.7

Discussion:

The partition coefficient found for benzoic acid in water was about 28. This is greater than 1,

which is expected. The partition coefficient for benzoic acid in sodium bicarbonate, on the other hand,

was less than 1. This value was to be expected as well, but it is on the higher side. In this experiment, we

used liquid-liquid extraction instead of distillation because there are two liquids that need to be separated.

The purpose of doing this extraction was not to recover a certain amount from another material, but to

measure the partition coefficient and solubility of the benzoic acid. We separated out the methylene

chloride layer from the aqueous layer of water in tube A. Tube B also had water in the aqueous layer

because when sodium bicarbonate reacts with benzoic acid, it creates carbonic acid, which is unstable and

breaks apart into CO​2​ gas and water. In both reactions, sodium sulphate was added to dry the non-visible

water left in the extracted layer. And to remove the sodium sulphate and further dry the organic layer, the

liquid left in the tube is then filtered through a sodium sulphate column using gravity to move the liquid

through. The methylene chloride and benzoic acid solution is then heated in a sand bath in order to

remove the methylene chloride to obtain pure benzoic acid. The tubes are then weighed to find the masses

that would determine the solubility and partition coefficients of benzoic acid in the two different liquids.

Sources of error could have affected my results. There could’ve been too much water taken with my

organic layer. I noticed that the “snow-globe effect” was not very present in my test tubes, which

indicates that might be the case. In order to determine the functional groups of benzoic acid to see if we
obtained it, an IR spectroscopy should be used. Around 1600 cm​-1​, there are peaks that suggest there is a

benzene ring in this structure. At around 1678 cm​-1​, there is a large peak suggesting that there is a C=O

bond. There are also medium peaks at 3071 cm​-1​, 3977 cm​-1​, and 2827 cm​-1​ that show multiple C-H

bonds. There are medium peaks at around 1601 cm​-1​ that shows double bonds between carbons. There is

also a peak at around 1101 cm​-1​, which shows a C-O bond.