Chemistry 227

Recrystallization

The main purpose of this experiment is to become familiar with the recrystallization
technique. Recrystallization will be used to purify an unknown impure mixture (acetanilide,
salicylic acid or benzoic acid) and a known sample of impure benzophenone. The unknown
will be recrystallized with distilled water and benzophenone will be recrystallized with
petroleum ether. Recrystallization of benzophenone will require hot gravity filtration. Melting
point determination will be used to measure the success of the recrystallization and to
determine the identity of the unknown solid.
Introduction
The technique by which a solid compound is purified by its characteristic solubilities is called
recrystallization. It is possible to purify compounds by recrystallizing them in a solvent in which
they are soluble at higher temperatures but insoluble at a lower temperature. The target
compound dissolves in the solvent at higher temperatures allowing the experimenter to filter
out insoluble impurities via hot gravity filtration. At low temperatures the target compound
forms crystals and precipitates out of solution while the soluble impurities remain dissolved in
the solvent.
Recrystallization involves dissolving the impure material in a minimum amount of boiling
solvent, gravity filtering the hot solution to remove any insoluble impurities, allowing the
solution to cool and to deposit crystals of the compound, vacuum filtering the crystals from the
cold solution that may contain dissolved impurities, and drying the crystals.
Choosing the proper solvent is imperative to a successful recrystallization. The properly
selected solvent dissolves a moderate quantity of the target substance near its boiling point,
dissolves only a minimal quantity near 0 C, does not react with the target substance,
dissolves impurities readily at all temperatures or does not dissolve them at any temperature
and is readily removed from the purified product.
Procedure
Solid Unknown (Benzoic Acid, Salicylic Acid or Acetanilide)
Dissolution. Obtain the impure sample. Prepare two melting point samples to be used later.
Record the appearance of the impure mixture. Weigh a small Erlenmeyer flask empty. Add
the remaining impure mixture to the Erlenmeyer flask. Weigh the Erlenmeyer flask and solid
mixture. Record the exact amount of original solid mixture being used. Add a stir bar to the
dissolution flask. Dissolve the impure solid in a minimum volume of hot solvent. Continue
adding hot solvent until the desired solid and soluble impurity dissolves. Note: Make sure
both the distilled water and the dissolution flask are being heated on the hot plate at the same
time! Also, make sure the mixture is stirred to facilitate dissolution. As the hot solvent is added

observe carefully whether solid is continuing to dissolve. Note: The impurity will dissolve.
Once all more solid dissolves, add another approximately 2-10 mL of hot solvent to prevent a
supersaturated solution upon cooling.
Isolation and Drying. Once the solution has cooled to room temperature, cool the
undisturbed crystals in an ice bath. Preweigh a watchglass and filter paper that fits the
Buchner funnel. Collect the crystals via suction filtration. Wash the crystals with cold solvent
(distilled water) to remove any adsorbed impurities and to maximize transfer of the purified
solid. Allow the crystals to dry until the next lab period. Store according to directions of
instructor.
Solid Known Benzophenone
Dissolution. Obtain the impure sample. Prepare two melting point samples to be used later.
Record the appearance of the impure mixture. Weigh a smaller Erlenmeyer flask empty. Add
the remaining impure mixture to the Erlenmeyer flask. Weigh the Erlenmeyer flask and solid
mixture. Record the exact amount of original solid mixture being used. Add a stir bar to the
dissolution flask. Dissolve the impure solid in a minimum volume of hot solvent. Note: Make
sure both the petroleum ether and the dissolution test tube are being heated in the water bath
at the same time! Continue adding hot solvent until the desired solid dissolves. Make sure the
mixture is stirred to facilitate dissolution. As the hot solvent (heated in test tube in water bath)
is added observe carefully whether solid is continuing to dissolve. Note: The impurity will not
dissolve.
Hot Filtration and Crystallization. Gravity filter the hot mixture using preheated equipment to
prevent premature recrystallization. Filter into a clean Erlenmeyer flask. If crystals form, add
more hot solvent until all of the solid dissolves. Depending on how much solvent was added
concentration of the solution may be required. If not, proceed to cool the undisturbed solution
to room temperature. Once the solution has cooled to room temperature, cool the undisturbed
crystals in an ice bath.
Isolation and Drying. Preweigh a watchglass and filter paper that fits the Buchner / Hirsch
funnel. Collect the crystals via suction filtration. Wash the crystals with cold solvent to remove
any adsorbed impurities and to maximize transfer of the purified solid. Allow the crystals to dry
until the next lab period.
Melting Point Determination. In the next lab period, weigh the watchglass, filter paper, and
dry unknown solid. Record exact weight of recovered unknown solid. Calculate percent
recovery. Determine the approximate melting point by completing the fast run. Determine a
more accurate melting point of the recovered solid by conducting a slow run. Use the melting
point data to identify unknown solid. Complete other characterization data according to the
instructor.

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Important Notes:
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Avoid adding too much hot solvent during dissolution. Watch carefully whether solid is
dissolving with each added portion.
Keep the dissolution vessel covered while heating to prevent loss of vapor and desired
solid.
Include stirring after each added portion of hot solvent to facilitate dissolution.
Preheat gravity filtration equipment well to prevent premature recrystallization.
Maximize transfer with cold solvent to maximize percent recovery during suction
filtration.
Goals include maximum recovery and maximum purity.

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