Preparing Benzoic Acid from Benzylalcohol

Preparing Benzoic Acid from Benzylalcohol

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Preparing Benzoic Acid from Benzylalcohol

Planning (a)

Problem

The aim of this experiment is to synthesize benzioc acid, with the
highest possible yield, by oxidizing benzylalcohol.

Hypothesis

We expect the percentage yield to be about 50% due to several
processes such as cooling and filtering.

Possible Variables

- Time

- Temperature (of water)

- Filter

Planning (b)

Apparatus/ Materials

- Round bottomed flask under reflux

- benzylalcohol

- HCl

- Na2O4

- Büchner funnel

- beakers

- sodium carbonate

Procedure

The benzioc acid is synthesized by heating benzylalcohol in a round
bottomed flask under reflux. In addition to that, we use Na2O4 as a
oxidizing agent. After that, we use HCl to precipitate it. After the
some time, we filter it through a Büchner funnel before it is
recrystallized and filtered again. The mass was recorded as it was
dry.

By adding sodium carbonate, we will now test whether what obtained is
benzoic acid or not, because one can observe bobbles if it is an acid.
After that we burn it to test if it is aromatic. Soot would be
possible to obtain if it was to be aromatic.

Data Collection

Mass of benzylalcohol

3.991 grams

Mass of flask (before adding benzoic acid)

95.47 grams

Mass of flask (after adding benzoic acid)

96.68 grams

After the addition of sodium carbonate

Bubbles were obtained

After burning it

Soot was obtained

Data Processing

Mass of benzoic acid

96.68 – 95.47 = 1.21 grams

We assume that the reaction goes to completion which would mean that
one mole of benzylalcohol should give one mole of benzoic acid.

Hence, the theoretical yield is 100% by amount of mol.

Molar mass

Benzylalcohol

108 g/mol

Benzoic acid

122 g/mol

Initial amount of benzylalcohol: [IMAGE]

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Amount of benzoic acid at completion: [IMAGE]

Percentage yield: [IMAGE]

Conclusion

The actual yield was about 27%. That means the underestimated
processes of purification such as stated in the hypothesis. The amount
of the produced benzoic acid in this experiment was probably higher
than the amount we have obtained in the end, because the number of
impurities in the final product were eminently lower than the amount
of lost benzoic acid due to purification processes.

After all, it is quite certain that the final product was benzoic acid
based on the fact that, according to tests, it was aromatic and
acidic.

Evaluation

Several processes, such as filtering for impurities not soluble in
water as well as filtering for impurities soluble in water, were
necessary to make sure that the final product of this reaction was as
pure as possible. However, it is very likely that at least some of the
benzoic acid was lost during that kind of processes, because the
product had to be transfered between several containers, and different
filters were used. We definitely lost some of the benzoic acid when we
filtered out the soluble impurities, because the acid is soluble as it
gave of its proton. Even though, the addition of HCl shifted the
equilibrium towards the side where the benzoic acid is undissociated,
we could not keep all the acid.

We lost a big amount of benzoic acid during the liquid filtering,
where it was dissolved to filter out the insoluble impurities. An
obvious amount was left in the filter after the dissolved benzoic acid
was precipitated due to the cooling of the solution on the funnel.

It is reasonable to assume that the obtained benzoic acid was quite
pure, so that impurities were just a small part of the mass of the
final product.

Suggestions of improvement:

- increase the number of purification processes to reduce the amount
of impurities, even though, that might result in a lower percentage
yield do to the fact that some of the benzoic acid might be lost in
processes, such as filtering

- when the acid runs through the filter, to filter out impurities, the
filter and the funnel should be warm and the solution heated more to
make sure that neither the acid precipitates nor is filtered out à
higher percentage yield

- prevent unintentional cooling and precipitation of the acid by being
faster with filtering out impurities à higher percentage yield
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