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Guidote AM, del Rosario DR, Abuzo AL. Experiencing Organic Chemistry.

Quezon City:
Office of Research and Publications, Ateneo de Manila University; 2005.
Experiment 3:

Separation of Benzoic Acid and


Naphthalene
Benzoic acid was first isolated from the dry distillation of gum benzoin. It is used as a
precursor to different compounds such as phenols, plasticizers and other benzoic acid
derivatives. It is also used as a preservative for acidic food and beverages through the
inhibition of the anaerobic fermentation of glucose of mold, yeast and some bacteria.
However, due to the low solubility of benzoic acid, its sodium salt sodium benzoate is more
widely used.

Napthalene is a natural constituent of coal tar, petroleum and coal. It is used in the
synthesis of phthalic anhydride, resins and naphthols, which are used in the synthesis of
various dyes. It is the primary ingredient of mothballs or moth repellents. Naphthalene
vapors build up in enclosed spaces to levels toxic to moths that attack textiles. It is also
used as a fumigant, and animal and insect repellent.

In this experiment, a mixture of benzoic acid and naphthalene is separated using a polar
and a non-polar solvent. Benzoic acid is made fully soluble in water by deprotonating it into
a benzoate ion using sodium hydroxide. It is later recovered as benzoic acid by protonation
using hydrochloric acid.

Prelab Questions
1. What is KD? Which is preferred in liquid-liquid extractions, a small KD or a large KD?
Explain.
2. Why are multiple successive extractions using small portions of solvent preferred
over a single extraction using large amount of solvent?
3. Which compound ends up in the aqueous layer and in the organic layer? Explain.
4. How are benzoic acid and naphthalene separated from each other?
5. Which solvent ends up in the upper layer? Lower layer? Explain.

Equipment
wax papers
2 2 in filter papers
sample vials

Chemicals
benzoic acid
naphthalene
hexane
10% hydrochloric acid
10% sodium hydroxide

Second Edition Draft For use only within the Ateneo de Manila University.
Guidote AM, del Rosario DR, Abuzo AL. Experiencing Organic Chemistry. Quezon City:
Office of Research and Publications, Ateneo de Manila University; 2005.
Procedures
Add about 5 mL hexane into the separatory funnel. Obtain an approximately 1 g mixture of benzoic
acid/naphthalene on a piece of wax paper. Put this into the separatory funnel and add about 10 mL
hexane to wash down the solids that have adhered to the sides of the mouth of the separatory funnel.

Add about 10 mL 10% sodium hydroxide into the separatory funnel. Put the stopper back on and
shake the flask vigorously until everything is dissolved. Open the stopcock occasionally to vent the
vapors that accumulate. Hold the funnel upright and swirl it gently to wash down the sides of the
funnel; set the flask aside to allow the mixture to resolve into two distinct layers.

TIP: Identify which of the two layers is the aqueous and the organic layer.
Drain the aqueous layer into a beaker and transfer the organic layer into an Erlenmeyer flask.

Recovery of Benzoic Acid


Return the aqueous layer back into the separatory funnel and wash it with about 5 mL hexane. Drain
off the aqueous layer and pour the organic layer into an Erlenmeyer flask. Repeat the process and
then collect the entire organic layer into the same flask.

Add ice-cold 10% hydrochloric acid into the aqueous layer until white precipitates of benzoic acid
form. Immerse the beaker containing the aqueous layer in an ice-water bath if necessary. Harvest
the crystals using suction filtration; wash the beaker with ice-cold distilled water if there are
precipitates remaining. Recrystallize benzoic acid in about 40 mL distilled water, heated until the
volume is reduced to about 25 mL. Air-dry the crystals and then get its mass and determine its
melting point. Submit the vial containing benzoic acid crystals.

Recovery of Naphthalene
Put the organic layer in the separatory funnel and wash it with about 20 mL distilled water. Drain off
and discard the aqueous layer. If the organic layer is hazy, decant it into a new Erlenmeyer flask and
dry it over anhydrous sodium sulfate until the solution becomes clear.

Heat a beaker half-filled with water. Choose a beaker such that a watch glass would fit over its
mouth. When the water starts to boil, use a medicine dropper to transfer some of the organic layer
onto the watch glass. Gradually add more solution as the solvent evaporates. The solvent may also
be allowed to evaporate under a fume hood in a vial. Exercise caution as naphthalene sublimes at
room temperature and is highly flammable.

TIP: Weigh the watch glass/vial before pouring in the solution. Dry naphthalene may stick onto
the glass and is very difficult to remove; transferring it into another container may significantly
decrease the yield.
Get the mass of the crystals and determine its melting point. Submit the vial containing
naphthalene.

Second Edition Draft For use only within the Ateneo de Manila University.
Guidote AM, del Rosario DR, Abuzo AL. Experiencing Organic Chemistry. Quezon City:
Office of Research and Publications, Ateneo de Manila University; 2005.
Postlab Questions
1. What factors may affect the purity of the benzoic acid and naphthalene obtained?
2. Would you expect a 100% yield for both benzoic acid and naphthalene using liquid-
liquid extraction? Explain.
3. What would be the effect on the yield for both benzoic acid and naphthalene if
hexane was replaced with either benzene or toluene?
4. Why isnt naphthalene recrystallized using hexane? What type of solvent can be
used to successfully recrystallize naphthalene? Why wasnt that solvent used to
extract naphthalene from benzoic acid?

References:
Most CF. Experimental Organic Chemistry. USA: Wiley & Sons; 1988.

Palleros DR. Experimental Organic Chemistry. USA: Wiley & Sons; 2000.

Second Edition Draft For use only within the Ateneo de Manila University.

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