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http://courses.chem.psu.edu/chem36/HTML/Experiments/recrstal.pdf
Recrystallization
Recrystallization is a useful purification method for most organic compounds that are solids at room
temperature. The selection of a proper solvent is the most critical part of the recrystallization procedure.
Organic solids are usually more soluble in hot solvent than in a comparable volume of cold solvent. The
process of recrystallization involves dissolution of the solid in an appropriate solvent at elevated
temperature and the subsequent reformation of the crystals upon cooling. This way, many impurities will
stay in solution and your target compound is purified. However, it is not possible to recover your entire
compound following a recrystallization. To maximize your yield, it is very important to only use a
minimum amount of hot solvent.
Choosing the appropriate solvent is the most challenging part of the recrystallization. In choosing a
solvent, remember that “like dissolves like”, which means that a nonpolar compound will dissolve well in
a nonpolar solvent, and a polar compound will dissolve well in a polar solvent. Also note whether a solvent
is flammable or not and find its boiling point. This will enable you to select an appropriate heating device.
Generally speaking, solvents with boiling points below 100°C should be heated in a water bath (NO OPEN
FLAME), above 100°C can be heated directly on a hot plate or you may use a sand bath.
Your task will be to recrystallize benzoic acid from water and from a solvent pair of your choice.
Benzoic acid is widely distributed in plants, such as anise seed, cranberries, prunes, cherry bark,
cinnamon, and cloves. In most plants, it acts as a natural preservative that inhibits the growth of bacteria,
yeasts, and molds. Its salt, sodium benzoate, is produced by the neutralization of benzoic acid with sodium
bicarbonate, sodium carbonate, or sodium hydroxide. The salt is not found to occur naturally. It is used a
preservative in a variety of food products, such as jams, soft drinks, and cereals. Benzoic acid is also an
effective food preservative, but its sodium salt is more popular, partly because it is more soluble in water
than benzoic acid.. Benzoic acid is also detected in car exhaust gases, presumably as an oxidation product
of toluene.
Procedure
(The solubility of benzoic acid in water is approximately 68.0 g per liter at 95 °C; and 1.7 g per liter at 0
°C. Calculate the amount of hot water needed to dissolve your sample of benzoic acid.)
Weigh out about 1.0 g of impure benzoic acid. Use a few milligrams to determine the melting point.
Transfer the remaining solid (after weighing accurately on the milligram balance) to an Erlenmeyer flask
containing a few milliliter of water. Heat the mixture with a hot plate. Add a boiling stick (a wooden
applicator) to the test tube to
prevent bumping. Heat the mixture to reflux. More solvent
is added to the mixture in small portions using a Pasteur
pipet until the solid just dissolves (saturated solution). Stir
until the solution dissolves. Record the total volume of
water used.
Cool the flask in an ice bath. As the solution cools, the
solubility of the solid decreases and the solid crystallizes.
Once the flask is cool and crystals have precipitated out,
collect by vacuum filtration.
Rinse the crystals with a small amount of a COLD 50/50 water/ethanol mix. Allow the crystals to air dry
on the filter, then weigh them, and take a melting point.
Note: The products of a chemical reaction should always be dried to constant mass, meaning its mass after
drying should not change significantly between two successive weighings.
Sometimes it is necessary to induce crystallization. This becomes necessary, if a solution does not
crystallize upon continuous cooling. Several techniques may be used to induce crystal formation. One
technique involves scratching the inside surface of the flask with a glass rod. The rod should not be fire-
polished and is moved vertically in and out of the solution. Enough force should be used so that an audible
scratching is heard. Seeding is the second technique. A small amount of the original crystal is saved, and
then placed in the cooled solution. This seed can promote crystal formation.
Procedure
Recrystallize another accurately weighed sample (about 1 gr)of benzoic acid using a solvent pair of your
choice. Consult the table of solvents and their dielectric constants and/or practice before hand with a small
amount of benzoic acid. Start with the solvent in which the substance is soluble. Always only use a
minimum amount of solvent. Continue to add the hot solvent in which the compound is more soluble
dropwise to form a solution. Then add the second solvent, dropwise again, to induce crystallization.
Collect, wash, and dry the crystals as above. Weigh the dried, purified crystals and obtain a melting point
Analysis
Calculate the percent recovery for both recrystallization procedures and compare the efficiency of each.
Percent recovery = weight of pure crystals recovered x 100
weight of original sample
Compare the melting points of the impure benzoic acid to the melting points of the pure samples.
Comment on the two methods of recrystallizations. Keep in mind that there are many situations where a
solvent pair is the only available option. Explain your choice of solvents in the solvent pair
recrystallization. Make suggestions for improvements to the experimental methods for recrystallization in
our chemistry lab.
Hand in your combined purified samples of benzoic acid in a properly labeled vial. (Name of the
sample, combined mass, and your name.)
Questions
1. Briefly describe how insoluble impurities are removed during a recrystallization?
2. Briefly describe how soluble impurities are removed during a recrystallization?
3. Both benzoic acid and 2-naphthol melt around 122 ºC. If you have an unknown sample of either of
these two solids, describe how you could determine if the solid was benzoic acid or 2-naphthol.