Falguniben Patel W212183422

EXPERIMENT 4 - Purification - Recrystallization of Benzoicacid

1. Introduction:

To discrete Benzoic acid impurities by the method of recrystallization and to calculate the
percent recovery of benzoic acid after the procedure. The amount of solute dissolved in the
solvent increases with the temperature ratio. This process of recrystallization may be used to
purify a solid and eradicate the impurities. A solid sample will remain impure in aqueous
solution and pure solution will be present on the filtered paper.

2. Equipments:

Hot plate, 125-ml Erlenmeyer flask, ice, stirring rod, spatula, Buchner funnel, impure benzoic
acid, weighing paper, digital scale, rubber tubing, benzoic acid, boiling stones, filter paper, 25ml
graduated cylinder, 50ml beaker, Mel-temperature apparatus.

3. Discussion:

All products after chemical reaction would be not pure. It should be purify by removing by-
products and impurities. Solid compounds are purified by this method where as liquids are by
distillation process.

With this recrystallization method solid compound may have two types of impurities: those more
soluble in a main component or vise-versa.

Synthetic organic substances always have some impurities so it can be purified by

recrystallization. Less soluble compounds will crystallize first. Crystal will form only between
the right molecules, so indirectly it will helps in the purification process. This process accelerates
purity of the final product but it is not the perfect process. The organic compounds’ solubility is
one of the important factors for this experiment. In general that compound would dissolve in the
solution at higher temperature almost at the boiling point of that particular compound and
completely insoluble at normal room temperature. One can use melting point experiment
previously to check the impurity of that compound before starting this experiment. An
acceptable solvent will dissolve ample of impure solution at higher temperature near it’s melting
point. At low temperature around 25 to -50 C, little pure compound should remain in the solution.
The volatile recrystallization solvent should be easily removed relatively during the
crystallization process. Make sure that solvent should not react with benzoic acid and it’s boiling
point should be lower than the melting point of the benzoic acid. Toxicity, flammability and
expense should be considered before the selection of the solvent.
Make sure that polar solvent dissolve polar compound easily and vise versa. Be careful selecting
that kind of like likes like solvent formula. Few are described as under,
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solvent formula polarity boiling point( C)
water H2O verypolar 100
ethanol CH3CH2OH polar 78
methanol CH3OH polar 65
dichloromethane CH2Cl2 slightlypolar 40
diethylether (CH3CH2)2O slightlypolar 35

Low carbon compound and compound with one polar functional group will easily dissolve in
water. You can see the relation between carbon number and solubility with this under described
table:

alcohol formula Solubility (g/100 mlH2O)

n-butanol CH3CH2CH2CH2OH 8
n-pentanol CH3CH2CH2CH2CH2OH 2
n-hexanol CH3CH2CH2CH2CH2CH2OH 0.5
n-pentanol CH3CH2CH2CH2CH2CH2CH2OH 0.1

The compound with more than six carbon can easily dissolved in non-polar compound as
benzene and cyclohexane. The solvent must be highly soluble in one another. If one compound
cannot be found than pair of different compound can be used like water –acetone and water-
ethanol etc. That compound should be dissolved in minimum amount of selected high
temperature solvent. Here, benzoic acid is easily soluble in hot water and not in cold water.

Solubility formulas are:

% lost in cold solvent = (solubility in cold solvent/solubility in hot solvent) x100

% recovery of solid = [g (solid) – g (solid lost)] x 100 / g (solid)
4) Procedure:

Figure 1- Dissolving benzoic acid

Erlenmeyer flask
Benzoic acid solution

Hot plate

1. Weigh out 1 gm of impure benzoic acid on weighing paper.

2. Add this compound into a 125-ml Erlenmeyer flask and add 20 ml distilled water.
3. Boil this mixture on hot plate and dissolved benzoic acid genteelly and completely.
4. If you can see any undissolved particles in that, add little bit cold or hot water only. Do
not add too much water as it will reduce saturation and decreased the amount of pure
compound.
5. Add drop by drop water into the mixture until all mixture will dissolve and solution is
boiling.
6. Add addition 10-15ml of water to that mixture after you see a complete clear solution and
not a single granular of solid benzoic acid.
7. Cover that small beaker with another Erlenmeyer flask on the counter top gently to avoid
dust contamination.
8. Allow flask to cool down gently around 5-10 minutes which will form good crystals.
9. After 10 minutes if the crystallization won’t happen then scratch the sides of flask above
the level of solution with rod.
10. That may scrape some small crystal into the solution and initiate forming crystallization.
That seed crystal serve as a nucleation point for the whole crystallization process.
11. An ice bath at this point may help to form more crystals.
 Fig. 2 – Büchner funnel and suction flask

Benzoic acid

Buchner funnel

Vacuum

Filtrate

12. Collect solid chemicals by placing suction filter paper on Buchner funnel apparatus
as shown in figure 2.
13. Now quickly pour the cool mixture into Buchner funnel.
14. Collect solid material using rod out of the flask soon. If needed use 1-2ml of cold water
to get all solid from the flask.
15. Run aspirator for few minutes to air dry the crystals.
16. By using spatula, remove filter paper from Buchner funnel and press that filter paper with
dry paper towel against it to make it complete dry.
17. Calibrate another weigh- paper and transfer that solid on that paper and weigh it again
18. Calculate the percent recovered using the following formula and determine the
melting point of recrystallized benzoic acid.

Weight of benzoic acid obtained after recrystallization

%Recovered = -------------------------------------------------------------------- x 100
Weight of benzoic acid before recrystallization
CHEM 2423 Recrystallization of Benzoic Acid
EXPERIMENT4– Recrystallization of BenzoicAcid

Data and Results (Recrystallization)

REPORT FORM Name: Falguniben Patel

Instructor: Dr.Yokabet Gideon

Date: 04-13-2020
1. Sample name: Impure Benzoic Acid

2. Data on the impure Benzoic acid

a. Mass of the benzoic acid +weighing paper 1.60g

b. Mass of weighing paper 0.60g

c. Mass of impure benzoic acid 1.00g

3. Data for recrystallized benzoic acid

a. Mass of recrystallized benzoic acid +weighing paper 1.20g

b. Mass of weighing paper 0.41g

c. Mass of recrystallized benzoic acid 0.79g

d. Calculation of percentage recovery

(Show calculation) = 0.79 (1.20-0.41) x 100
1.00 (1.60-0.60)

=79%

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d. Melting point of recrystallized benzoic acid 121-124 C

e. Structural formula of the benzoic acid

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 CHEM 2423 Recrystallization of Benzoic Acid
Pre-Laboratory Questions–EXP4 Name:Falguniben Patel

1. What is the ideal solvent for crystallization of a particular compound? What is the primary consideration in
choosing a solvent for crystallizing a compound?

- It does not react and dissolves compound with solubility difference with temperature. It should remove from
crystals by washing or evaporation. Fast evaporation with low boiling point compound is ideal. Moreover, it
should be a high temperature coefficient.

2. Impure benzoic acid was dissolved in hot water. The container of solution was placed in an ice-water bath
instead of being allowed cooling slowly. What will be the result of cooling the solution in this manner?

-In this manner solution will precipitate and not crystallized. Moreover, this compound will carry more
impurities.

3. Outline the successive steps in the crystallization of an organic solid from a solvent and state the purpose
of each operation.
1. Dissolve solid product in minimum volume of hot solvent . Purpose- to get into solution
2. Cool solution in a mixture of ice, water and salt. Purpose- to enable pure product to crystallise, solubility
decreases with temp, so cold. Impurities are present in small quantities, so do not saturate and are left in
solution.
3.If it all sets solid, you haven't used enough solvent, so add a little more and warm until everything
dissolves. Purpose: you need solid and supernatant liquid to effectively filter and remove impurities.
4.Filter preferably by Buchner filtration. Purpose to remove surplus solvent
5. Wash filtrate with a little cold solvent. Purpose .. solid will be wet with solvent containing impurites ..
need to wash this away .. but not so much that you lose a lot of your yield by it redissolving in solvent
6 .let suction continue for a while. Purpose to remove bulk of washing solvent
7. remove filter pad, and scrape product onto a pad of several bits of dry filter paper and spread it out using
a spatula. Purpose: to let last bit of solvent evaporate to give pure, dry product. This is vital or melting point
will be inaccurate.
8. for normal lab, where both percentage yield and melting point are important, this will do. However if
you want a very pure product or have to check the melting point, repeat the whole process. Purpose: to get
very pure product and 'spot on' melting point. You will however get a slightly lower yield.

4. Compound X is quite soluble in toluene, but only slightly soluble in petroleum ether. How could these
solvents be used in combination in order to recrystallized X?

To recrystallized X, you'd heat it in a solution of petroleum ether, where it is mostly insoluble. Then you'd
add a small amount of toluene until it dissolves. Then you slowly cool the mixture, and the crystals should
come out of solution.
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5. 0.12 g of compound “Y” dissolves in 10 ml of acetone at 25 C and 0.85 g of the same compound dissolves
in 10 ml of boiling acetone. What volume of acetone would be required to purify a 5.0 g sample of
compound?

5gm x10ml
0.85gm = 58.82 ml acetone would be required to purify 5g of compound.

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CHEM 2423 Recrystallization of Benzoic Acid
Post-Laboratory Questions–EXP4 Name:Falguniben Patel
Due after completing the lab.

1. Give some reasons why Suction filtration (vacuum) is to be preferred to gravity filtration.
Vacuum filtration provides dryer products in less time and it is faster than suction filtration. It is also most
useful when crystals are filtered out.

2. A student recrystallized some impure benzoic acid and isolated it by filtration. He scraped the purified
benzoic acid off the filter paper after it had dried and took the melting point as a test for purity. He was
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surprised that most of the white solid melted sharply between 121 and 122 C but that a small amount
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remained unmelted even at temperatures above 200 C. Explain this behavior.
- The unmelted material was not the benzoic acid. It was impurity of that compound remain unmelted.

3. What does the term “oiling out” mean? How can one prevent oiling out?
Oiling out means when a solution produces insoluble oil instead of crystal because it became insoluble at a
temperature above the melting point or due to too little of solvent. One can prevent oiling out by adding
more solvent or by using solvent with lower boiling point.

4. What are the purposes of the following in recrystallization of solids?

I) Boiling stones– It will prevent bumping of the solution upon boiling.

II) Activated carbon- It will remove any colored impurities during the crystallization.

III) Seed crystals– The seed crystal is a small piece of single crystal from which a large crystal of same
material is to be grown. Upon addition of a seed crystal to supersaturated solution large crystals can be
grown easily as the intermolecular interactions can be formed much more easily. The process may also
be called nucleation.

5. Give one reason why we cannot reuse boiling chips?

Boiling chips catch the chemicals in its pores and were reuse them , they would release those chemicals
and contaminated that solution.

6. 0.12 g of compound “Y” dissolves in 10 ml of acetone at 25 oC and 0.85 g of the same compound
dissolves in 10 ml of boiling acetone. If 5.0 g of compound “Y” were to be recrystallized from 75 ml
acetone, what will be the next maximum amount of “Y” that will be recrystallized?

Boiling Acetone need for 5gm of compound = 5g x 10ml/0.85g = 58.82 ml

Grams lost in cold water = 58.82ml x 0.12g /10ml = 0.70g
Solid recovered (g) = 5g- 0.70g = 4.30 gm
Solid recovered (%) = 4.30g/ 5g x 100 = 86%