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Theory
❖ definition

Recrystallization is an important technique for purifying organic solids. The contaminated

solid is dissolved in a minimum of hot solvent, then cooled. The amount of solvent that is
used should be just enough so that the solvent is just barely saturated or almost saturated
when it is boiling hot.

Upon cooling the solubility decreases, and crystal formation can occur. The new crystals
are purer than the original because impurities are left in the solvent. Slow, gradual cooling
is best for formation of pure crystals. Filtration then provides purified material. Some mass
loss always occurs, because the solvent holds not only the impurities but also some of the
desired material as well. Additional unnecessary mass loss can occur if you use too much
solvent, don’t heat your solution to boiling in the process of dissolving your sample, if you
don’t cool adequately, or if you wash your product crystals excessively.

An appropriate solvent needs to have mediocre dissolving power: strong enough to dissolve
the sample when boiling hot, but not able to dissolve too much of the sample when cold.

❖ Purpose of the experiment

Separation and purification of solid organic compound

Objective: To separate benzoic and acetanilide impurities by the technique

recrystallization and to Calculate the percent recovery of benzoic acid and acetanilide after
recrystallization. Theory: As the Temperature increases, the amount of solute dissolved in
the solvent increases also.

❖ Types of cooling

Progressive cooling

Sudden cooling

❖ Types of crystal development

Crystal growth is the process that describes the formation of crystals during crystallization.
Crystal growth usually occurs in order after the nucleation process, unless a crystallization
nucleus is used to obtain the desired shape of crystals.

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Quartz crystals.

The crystal growth process gives a crystalline solid resolution in which the atoms or
molecules are aligned closely together, with constant spaces between each other in the
regular crystals, and the state of the crystalline material is distinguished by the presence of
the solidification property

Techniques edit

- Crystal growth from molten

An example is the Czukhralsky process and band smelting, which are used to prepare
wafers of single crystals of silicon.

- Crystals grow from the gas phase

Examples include sublimation or physical vapor deposition as well as chemical vapor

deposition.

- Crystal growth from solution

It is the most common case used in chemical laboratories, where the substance is dissolved
in a suitable solvent until saturation. Crystal growth from solution is achieved either by
evaporation of the solvent, or by changes in temperature.

❖ The properties of suitable solvent used in recrystallization:

1. It should not dissolve the compound in low temperature (at room temp.) but readily
dissolve the compound in high temperature (at its boiling temp.).

2. It should not dissolve the impurities in high temperature.

3. It should not react with the compound to be purified.

4. It should have a boiling point lower than the melting point of the solid purified.

5. The solvent should be volatile enough to be easily removed from the solvent after the
compound has crystallized.

6. Not toxic, available, cheap, inflammable.

❖ Why is gradual cooling preferred over sudden cooling in a process Show crystals in
the crystallization process?

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Gradual cooling is preferred over sudden cooling in the process of showing crystals in the
crystallization process in order to give enough opportunity for the crystals to grow and grow
well so that they can be distinguished either with the naked eye or by a microscope

❖ Sometimes the separation of the solvent in the solution may be difficult or delayed. In
this case, it must be Do the following: -

1. Adding one or two crystals of the dissolved compound, if available, to make this crystal
work as a nucleus, crystals of the substance to be purified are gathered around it.
2. Scratch the walls of the beaker or beaker containing the vessel to be collected with a
glass motor So that the charges generated by induction act as a nucleus around which
the crystals gather.
3. Adding an amount of another solvent so that it completely mixes with the first solvent
and has less solubility of the solute from the first solvent, in this case the second solvent
works to push Crystals outside the first solvent.

4. Heating

5. Cooling

Appropriate solvent test Conduct an experiment on the solubility of a solid that transports
a small amount (20 mg) of the substance To be purified by a teaspoon to a small test tube
and add to it about (5,0 .). Ml (ml) of the solvent, we stir the substance with a glass rod,
when the organic matter is Insoluble in the cold solvent, the solution is heated and the
organic matter is dissolved If flammable solvents are used, the test tube is heated in a water
bath The whole substance is in the hot solvent, in this case the solvent is suitable to dissolve
the substance If the solid is not completely dissolved in the hot solvent, it must be Add
another amount of solvent to obtain a clear solution. The resulting solution is cooled under
the water tap and if necessary, rub the walls of the tube with a glass rod and note Crystal
clearing. Thus, the process of testing the appropriate solvent by taking several solvents such
as Water, ethyl alcohol, acetone or benzene, etc., and choose the appropriate solvent for the
solution

And note the quality of the crystals in each solvent separately. In the process of testing the
appropriate solvent, the well-known term “like dissolves like” is noted The like dissolves the
like (that is, the polarized solvent dissolves the polarized substance and the solvent is not
The polarizer dissolves the non-polarized material, meaning that the material is similar in
composition and property Solid organic matter with appropriate solvent.

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 Material and Tools

Material

Benzoic acid

Water

Tools

Electrical Balance

Spatula

Beaker

Conical flask

Funnel

Stand with clamp

Filter paper

Burner

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 Procedure
1- Using a balance, we weigh 0.5 grams of benzoic acid
2- Put the benzoic acid in the beaker and add 20 ml of distilled water
3- We put the beaker on the benzene burner until the benzene dissolves in the water
4- Then we filter the hot solution into the conical flask
5- We let the conical Flask cool down a little, then put it in a cold-water bath to form
crystals
6- We are filtering again
7- We let the crystals on the filter paper dry Then the percentage is calculated

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Data

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 Discussion
The crystallization process is one of the methods used to purify solid organic materials
obtained from various reactions or that are isolated from some natural elements such as
leaves and seeds. It can be purified and diagnosed easily. The solvents suitable for
crystallizing a compound must meet several conditions, including the compound to be
crystallized while it is hot, and the impurities must be dissolved while it is cold, and that it
does not react chemically with the compounds to be crystallized, and that its boiling point
is lower than the melting point of the compounds to be crystallized. Ideally, we must
provide the following conditions: - Non-toxic – Non-flammable – Cheap We can divide
industrial carbon into two types: crystalline carbon and non-crystalline carbon. Activated
carbon is considered one of the forms of non-crystalline carbon. Some models contain
colored dissolved substances that cause the solution to discolor the solution. It is yellowish
in color or causes darkening in the colors of the colored organic matter. These impurities
can be removed by removing animal charcoal. As for the double solvent, it is two close
compounds mixed with each other and different in their solubility for a particular
substance. There is a big difference between crystal and precipitation, as precipitation is
the process of forming a solid substance while crystal is Process of slow crystallization
solid. The filtration process is used here for many purposes, including separating solid
impurities from a liquid or solution and collecting a solid product from the reaction
mixture or from for a solution from which a water compound has been crystallized, there
are two filtration methods: side filtration and vacuum filtration .

❖ Sometimes the separation of the solvent in the solution may be difficult or delayed.
In this case, it must be Do the following: -
1. Add one or two crystals of the dissolved compound, if available, to make this crystal
work as a nucleus, crystals of the substance to be purified are gathered around it.
2. Scratch the walls of the beaker or beaker containing the vessel to be collected with a
glass motor So that the charges generated by induction act as a nucleus around
which the crystals gather.
3. Adding an amount of another solvent so that it completely mixes with the first
solvent and has less solubility of the solute from the first solvent, in this case the
second solvent pushes Crystals outside the first solvent.

❖ Why we use minimum volume from solvent?

To prevent the loss of the compound because large volume of the solvent will keep most of
the compound dissolves in it.

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 ❖ Why we can’t put the hot solution directly into the ice bath?

You need to cool the solution first to room temperature before placing it in the ice-water
bath. Besides reducing the risk of breaking your flask and losing your product in the ice-
water, you will get better and purer crystals if you let the solution cool slowly.

❖ Why It is very important that we add the minimum amount of boiling solvent ?

In order to get a saturated solution. If you add too much solvent, the solution may be too
dilute for crystals to form.

❖ What is the purpose of first Filtration?

To remove of impurities.

❖ What is the purpose of second filtration ?

To have the pure crystal from mother liquor.

❖ What happens if you add too much water during recrystallization?

If you add too much solvent, the solution may be too dilute for crystals to form. It is
important to Slowly cool the flask first to room temperature and then in ice-water. A
rushed crystal formati

References

[1] Laurence M. Harwood, Christopher J. Moody (1989). Experimental organic

chemistry: Principles and Practice

[2] John Leonard; B. Lygo; Garry Procter. Advanced practical organic chemistry

[3] K. B. Wiberg, Laboratory Technique in Organic Chemistry, McGraw-Hill, New York,

1960, p. 98.

[4] A. I. Vogel, Practical Organic Chemistry, 3rd edition, Wiley, New York, 1956, p. 122.