The most commonly used technique for purifying a solid compound is re-

crystallization. In the most basic form of this process, the solid compound is
dissolved in a minimal amount of a hot solvent, and then the solution is allowed to
cool until the compound precipitates, or "re-crystallizes," from a super-saturated
solution. Impurities, which often are soluble in the solvent, stay dissolved, and
these impurities are removed, along with the solvent by filtration. As you may
have guessed, the success of this technique depends heavily on the solvent being
used.  The solid compound (solute) must be only slightly soluble in the solvent at
room temperature, while being virtually completely soluble in the solvent at higher
temperatures. In addition, it is vital that the solvent not react with the compound
which is being purified.

It is often the case that this basic form of re-crystallization is not sufficient to
remove all of the impurities--for instance, those impurities that are insoluble in the
solvent used for re-crystallization. In this case, the hot solution (with the solute
dissolved completely in the hot solvent) must be filtered while it is hot, without
allowing it to cool more than a few degrees to prevent any re-crystallization to
take place. This "hot filtration" technique removes those insoluble impurities all
the while keeping your solute in solution.  The "hot filtration" technique can be
tricky if you allow the solution to cool even a little bit. Therefore, once you are
fairly certain that your desired solute is fully dissolved, quickly perform a vacuum
filtration using a Büchner funnel to collect the filtrate, containing your dissolved
solute, to prevent appreciable formation of crystals.

Safety: Benzoic acid is a severe irritant and a sensitizer (exposure to

sensitizers does not cause cancer, but can make you more susceptible to those
substances, which do cause cancer), and is therefore classified as a harmful
solid. You may wish to wear gloves while handling it.  Be sure to wash your
gloves and hands after handling it.  

Before you begin the re-crystallization of benzoic acid, you should have
determined its solubility (you should have looked up this information in Exp 1a).
If you did not find this information for benzoic acid, its solubility is 0.34 g per 100
mL of cold water

Obtain about 1.0 g of "impure" benzoic acid (this sample of benzoic acid has a
small amount of sodium chloride added to it). What kind of container should you
use for the solid? (Guideline 1--however, we will be using only about 15-20 mL of
solvent, so use a 50-mL or a 125-mL beaker for this re-crystallization). Heat about
50 mL of DI water in a 150-mL beaker. Add about 15 mL of the heated water to
the "impure" benzoic acid (in your beaker), and place the benzoic acid/hot water
mixture on the hot plate. Add more hot water to the benzoic acid, as needed, until
the benzoic acid has completely dissolved (usually at boiling conditions). If the
 solid does not fully dissolve within about 5 minutes, using the initial 15-mL
sample of hot water, add more hot water in 5-mL increments. Once the solid has
completely dissolved, add an additional 2-5 mL of hot water to keep it dissolved.
Remove the container from the hot plate (and turn off the hot plate). 

Based on the solubility of benzoic acid in water, you can estimate your recovery.
For example, if 0.34 g of benzoic acid dissolves in 100 mL of cold water, then if
you started with 1.0 g of benzoic acid, the maximum you could recover by
crystallization would be about 0.66 g if you used 100 mL of water. If you used 50
mL of water, then only about 0.17 g would stay dissolved, and you would recover
a maximum of about 0.83 g of benzoic acid. How much water did you actually
use? How much benzoic acid should you recover?

Let the benzoic acid solution cool by placing on the bench top. After the mixture,
with some crystals present, has cooled to room temperature place the beacker in an ice bath to
enhance crystallization and crystal recovery, since most chemicals are less soluble at cooler
temperatures. Never place the beaker directly in an ice bath from the hot plate.  Let crystals for
normally by sitting on the bench. If you cool the supersaturated mixture too soon, before you
allow it to cool to room temperature, you may actually trap impurities in the solid material. 
Letting nature for crystals naturally is much for efficient and practical. Using vacuum filtration
you should collect your crystals. Use a small Büchner funnel placed on top of a 250-mL
vacuum filter flask. The vacuum assembly consists of your vacuum flask with Büchner funnel
connected to a vacuum trap which is inserted into a vacuum-trap-bottle which is then
connected to the vacuum line. After pouring your crystalline mixture into the Büchner funnel,
wash your beaker with DI water and collect this additional crystalline material in your funnel.
Wash the solid material with a little DI water to removed filtrate material and any soluble
impurities. Let the vacuum run for an addition 5 minutes or so before turning off the vacuum
and collecting your crystals

CHEMICAL INFORMATION

Name Structure (2-D)

benzoic
acid