Objectives

1. To be able to purify Benzoic acid by means of recrystallization

2. To determine the percent recovery and melting point of benzoic acid
3. To test the purity of the product by determining the melting point.

Introduction

Crystallization is the process when a solute dissolves in a hot solvent and then returns to a solid
again by crystallizing in a cooled solvent. The crystalline substance is dissolved in a hot solvent
which will increase the solubility of the solution and eliminate any impure substances through
gravity filtration. Then the solution is slowly cooled causing the pure substance to recrystallize
and be isolated from the solution via filtration.

1. Why should the crystallization solution be cooled first before adding decolorizing
charcoal?
a. The carbon particles can act as minute boiling chips. If they are added to a hot
solution, frothing may occur.
b. It is important to remember that the fine carbon particles of charcoal can act as
tiny boiling chips. Because of this, there is almost an absolute certainty that the
heated solution would froth
2. How is premature crystallization prevented when filtering the insoluble impurities from
the hot crystallization solution?
a. Thus, the glassware immediately in contact with the hot solution must also be
kept hot.
b. The glassware (an Erlenmeyer flask and a funnel) must be preheated in an oven,
and used while very hot at the time when the solution to be filtered is ready.
3. Why shouldn’t the hot crystallization solution be immediately placed in an ice-water
bath?
a. Bumping the flask may induce precipitation instead of crystallization. Placing the
hot flask in an ice-bath also produces precipitates rather than crystals. Thus, it is
important to take note that crystallization is a slow cooling process rather than a
fast and rapid one. It is important to ensure that there is no abrupt change in
temperature; otherwise, the impurities may be trapped inside the crystal lattice
making the isolated crystals smaller and impure, as shown in Figure 2.
4. What is the importance of covering the crystallization solution covered with a watch
glass or beaker during cooling?
a. The crystallization flask must be covered with a watch glass during cooling down
to prevent dust contamination and solvent evaporation.
5. Why should the crystals be washed with cold water during suction filtration?
a. At this point, the crystallization solution would have already cooled to room
temperature, and stayed at that temperature for quite some time. Placing the
flask in an ice-bath may also increase crystal yield. The crystals may be separated
from the mother liquor through suction filtration.
 b. Once the suction filtration process is completed, the collected crystals should be
washed with a little more ice-cold solvent to remove final soluble impurities
which would otherwise be left on the surface of the crystals. The solvent used
for this final washing should be as cold as possible to minimize losses from the
crystals re-dissolving.
Reagents

1. Crude Benzoic Acid

2. Decolorizing Charcoal
3. Water

Reagents Phys and Chem Properties Safety Precautions

Crude Benzoic Acid. Physical state and appearance: Hazardous in case of skin
Sodium Benzoate Solid. (Granular solid. crystalline contact (irritant), of inhalation.
powder.) Slightly hazardous in case of
ingestion.
Odor: Odorless..
Molecular Weight: 144.11
g/mole
Color: White.
Melting Point: >300°C (572°F)
Solubility: Easily soluble in cold
water, hot water.
Decolorizing Charcoal Physical state and appearance: Keep away from heat. Keep
Carbon Solid. (Solid powder.) away from sources of ignition.
Odor: ​Odorless. Ground all equipment containing
Molecular Weight: ​12.01 g/mole material. Do not breathe dust.
Color: ​Black Keep away from incompatibles
Melting Point: ​3500°C (6332°F) such as oxidizing agents, metals,
Solubility: ​Insoluble in cold acids.
water, hot water.
Store in a segregated and
approved area. Keep in a cool
and ventilated area away from
combustible materials
Water Physical state and appearance:
Oxidane Liquid.
Odor: ​Odorless.
Boiling Point: ​100°C (212°F)

Procedures and set-ups

 1. Weigh 2.0 g of contaminated benzoic acid into another Erlenmeyer flask.
2. Add 2-3 boiling chips and 60 mL of distilled water, and then heat to boiling until the compound
dissolves.
3. Remove the flask from the burner and add into it 15 mL of cold water.
4. Add a spatula-point, or less, of decolorizing charcoal.
5. Boil the treated solution carefully for 1-2 minutes and watch out for frothing.
6. Filter the hot solution using gravity filtration (SEE FIGURE STH) into a fluted filter paper in a
warmed funnel and flask.
7. Once the filtrate runs clear, let the solution cool,
8. add 2-3 boiling chips into it and boil off excess solvent until the volume is 50-60 mL.
9. Allow the solution to cool down to room temperature and crystallize.
10. Chill it afterwards in an ice-water bath and then harvest the crystals using suction filtration (SEE
FIGURE STH).
11. Air-dry the crystals overnight.
12. Determine the percent recovery and determine melting point using a melting point apparatus.
13. Compare the appearance of the crystals with crude benzoic acid.
14. Place the recovered crystals in separate vials, label.
15. Hand them to your instructor.

Data and Observations