Experiment 5: Carboxylic acids: Preparation of benzoic acid

Objective:

To prepare benzoic acid from benzyl alcohol.

Introduction:

Carboxylic acids contain the carboxyl group. Carboxylic acids can be prepared
by oxidation of primary alcohol. In this experiment, an aromatic carboxylic acids
namely benzoic acid will be prepared by oxidizing benzyl alcohol. The oxidizing
agent used is alkaline potassium permanganate (VII). Reaction between the
alcohol with the oxidizing agent will produce sodium salt (i.e sodium benzoate),
which on acidification with hydrochloric acid will produce benzoic acid.

Materials:

Sodium hydroxide, potassium permanganate, benzyl alcohol, concentrated

hydrochloric acid, sodium sulphite, methyl orange solution and anti-bumping
stone granules.

Apparatus:

Buchner funnel, 100 mL round bottom flask, and filter paper.

Methods:

1. The mass of a small empty beaker is determined using the electronic

balance.
2. 3 mL of benzyl alcohol is transfered into the beaker and the mass of the
alcohol is weighed.
3. 2 g of sodium hydroxide is dissolved in 25 mL of distilled water, in a dry
100 mL of round bottom flask.
4. The weighed benzyl alcohol and 5g of potassium permanganate is added
into the round bottom flask.
5. Two to three anti-bumping granules is placed into the flask and allow
the solution to be refluxed for at least 30 minutes (make sure that
the solution is boiling).
6. Upon reflux, immediately transfer the hot mixture into a Buchner funnel
which is attached to a running water and vacuum filter the hot solution
obtained from the previous step.
7. The filtrate i s collected and a few drops of 10% of sodium sulphite is
added to eliminate the remaining/unreacted permanganate ions in the
solution. The colour of the filtrate will change from pink/light brown to
colourless upon addition of sodium sulphite.
8. Afew drops of methyl orange is added into the filtrate and shake well.
9. A few drops of concentrated hydrochloric acid is added into the filtrate
while shaking until the colour of the solution changes from red to blue.
10. The flask containing the solution is immersed in ice for a few minutes
to speed up the crystallization process.
11. The solution is transferred into a clean Buchner funnel and vacuum filter
to obtain the crystals formed (Remember to determine the weight of the
filter paper used for the vacuum filtration).
12. The remaining crystal particles left in the flask is rinsed with cold
distilled water and repeat step 11 to obtain all the crystals formed.
13. The crystals are formed and the filtrate is discarded into a waste
container. The crystals are placed on a clean petri dish and leave it
overnight at room temperature to allow the precipitate to dry completely.
14. On the following day, the mass of the crystals formed is weighed and
recorded, after which the percentage of product formed is being
calculated to be shown in the results section.
Results

Mass of beaker = 19.88 g

Mass of beaker + benzyl alcohol = 22.91 g
Mass of benzyl alcohol = 3.03 g
Mass of petri dish = 16.23 g
Mass of petri dish + benzoic acid = 18.01 g
Mass of benzoic acid = 1.88 g

Benzoic acid theoretical weight,

C6H7COH + [O] → C6H7COOH

𝑁𝑎𝑜𝐻,𝐻2𝑂,𝑅𝑒𝑓𝑙𝑢𝑥

Based on the balanced equation above, 1 mol of Benzyl alcohol forms 1 mol of
benzoic acid, 1 mol C6H7COH ≡ 1 mol C6H7COOH.
Hence, number of moles of benzoic acid = 3.03g / 108 gmol-1 = 0.0281 mol
0.0281mol of benzoic acid gives out mass of = 0.0281 mol x 122 = 3.423g

1.88
Percentage of product formed = x 100%
3.423
= 54.93%

Discussion:

In this experiment, our main objective is to produce benzoic acid in its solid
form. We have obtained the mass of benzyl alcohol which is 3.03g whereas the
benzoic acid formed through oxidation, filtration and purification is 1.88g. The
percentage yield of the benzoic acid is 54.93% compared to the theoretical weight
of benzoic acid. It is consider a success as the benzoic acid obtained by us
through experiment is more than 50%.

Additionally, reflux reaction of using Liebig’s condenser and allow water to

flow through it is used as it speeds up the reaction while preventing any volatile
products or reactants from escaping in vapour form. This ensures that the
reactants are all fully reacted without escaping into surroundings.
 Besides that, a Buchner funnel is preferred in this experiment as it uses
pressure also known as vacuum. Compared to the regular funnel which depends
mainly on the gravitational pull whereas Buchner funnel uses pressure which is
produced by having the high speed water to pass through forming vacuum
suction. By doing so, the filtrates are easily filtered and the residue can be
obtained in a faster time.

Questions:

1. Write down the complete chemical equation(s) for each step of the reaction
from steps 1 to 7.

a. C7H8O KMnO4/NaOH C7H6O2

b. C6H5COOH+NaOH C6H5COO-Na+ + H2O

c. C6H5COO-Na+(aq) + HCl C6H5COOH (s) +NaCl (aq)

d. Na2SO3 +MnO4- :

SO32- + MNO4- SO2 + Mn2+

2. a) What is the purpose of reflux in step 5?

Heating under reflux prevents any aldehyde (volatile) formed escaping
before it has time to be oxidised to the carboxylic acid.

b) Why is Buchner funnel preferred in this experiment, instead of using a

regular funnel?

In this experiment, a Büchner funnel is used for vacuum or suction

filtration instead of the regular funnel. Vacuum, or suction, filtration is
more rapid than gravity filtration and is most often used to collect solid
products resulting from precipitation or crystallization. This technique is
used primarily when the volume of liquid being filtered is more than 1-2
mL. In a vacuum filtration, a receiver flask with a sidearm, a filter flask,
is used. The sidearm is connected by heavy-walled rubber tubing to a
 source of vacuum. Thin-walled tubing (such as the tygon tube used to
connect cooling water) will collapse under vacuum, due to atmospheric
pressure on its outside walls, and will seal the vacuum source from the
flask. It is occasionally necessary to use specially prepared filter beds
to separate fine particles when using vacuum filtration.

Conclusion:

As a conclusion, benzoic acid can be formed through oxidation of benzyl

alcohol. However, the process does not stop there but it continues. Hence, in
order to obtain benzoic acid, process such as substitution, filtration, purification
has to be taken in order to obtain the benzoic acid. Last but not least, the
percentage yield of benzoic acid is 54.93%.

References:

1) http://www.chemicalland21.com/industrialchem/organic/benzoic%20acid.htm
2) http://www.chemicalland21.com/industrialchem/solalc/benzyl%20alcohol.htm
3) Jim Clark. (2004) Making Carboxylic Acids.
http://www. chemguide.co.uk/organicprops/acids/preparation.html#top