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Title: Extraction separation of a Mixture of Benzoic Acid, Naphthalene , Aniline

Objective:
The objective of this lab is to separate a mixture of naphthalene and benzoic acid.
MSDS:
Acids Uses of acid solution Base Uses of basic solutions
Use this solution only to Use this solution only to
6M
6 M HCl neutralize a basic solution never neutralize an acidic solution
NaOH
for extractions never for extractions
Use this solution for washes and Use this solution for washes and
1.0 M 1.0 M
extractions (e.g., in a separatory extractions (e.g., in a separatory
HCl NaOH
funnel) never for neutralizations funnel) never for neutralizations
10% NaHCO3 (sodium bicarbonate solution) can be used to neutralize an acidic solution
within a separatory funnel, if you want to end up with a solution near neutral pH. To get
rid of the NaHCO3, simply use 2-3 DI water washes, effectively washing the ether layer
and getting rid of the bicarbonate ion. Do not use sodium bicarbonate solution to
neutralize an acidic solution not in a separatory funnel.

Materials:
 Naphthalene  Ventilated hood
 Benzoic acid  Ice bath
 Separatory funnel  Watch glass
 Droppers  Sodium chloride
 Beakers  Ethanol
 3M hydrochloric acid  Bunsen burner
 Aniline  Vacuum
 Methylene chloride  Filter paper
 3M sodium hydroxide  Buchner funnel
 Anhydrous sodium sulfate.  Filtering flask
 pH paper 
 Erlenmeyer flasks

Methods:
Steps in an Extraction

1 A solvent or solvent mixture was carefully added to the separatory funnel.

2 the extraction solvent was added to the funnel.
3 the resultant layers were mixed.
4 the layers were left to settle and separate.
5 the last latter was drained into Erlenmeyer flask.
6the remaining layer was drained into an Erlenmeyer flask.

Part A. Separation of the Three Components by Chemically Active Extraction

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1.1 gram of benzoic acid, 1 graam naphthalene, and 1 mL aniline were weighed out and dissolve
it in 20 mL of methylene chloride in a clean beaker.

2. After it was completely dissolved, it was transfer to the separatory funnel (make sure the
stopcock is closed before it was added.

3. The contents of the separatory funnel was swirled to encourage dissolution.

4 This solution was extracted twice with 10 mL portions of 3M hydrochloric acid

5. The aqueous layers from each of the acid extractions into the same labeled flask. the layers
were identified it was tested by checking for the aqueous layer by adding a drop of water.it
mixed with the top layer meaning that was the aqueous layer.
6.The organic layer was returned to the separatory funnel and extracted twice with 10 mL
portions of 3M sodium hydroxide.
7. The aqueous extracts were combined from each of the base extractions into a second labeled
flask (Base Extract).

8. The organic layer was combined into a small flask and dried using anhydrous sodium sulfate.
it was decanted into a labeled and weighed beaker and placed in the ventilated hood for the
solvent to evaporate.
9. The Base extract was cooled in an ice bath.

10.The Acid extract is basified with 6M sodium hydroxide to pH 9; pH paper was used to
confirm.

11. 10 ml of methylene chloride was added to the basified acid solution to dissolve the liquid
product. It was separated using a separatory funnel. The organic layer was collected in a small
flask, iit was dryed with anhydrous sodium sulfate and decanted into a labeled weighed small
beaker and the solvent was allowed to evaporate in the ventilated hood.

12. The cooled base extract from step 9 was acidified with 6M hydrochloric acid to pH 3; a
white precipitate appeared in the flask. pH paper was used to confirm.

13. The precipitates by vacuum filtration were isolated. The precipitates were thoroughly washed
with cold water to remove aqueous sodium chloride.

14. The precipitates were spread and labeled on a weighed watch glass and allowed to air dry.

15. The weight of all samples and melting point of the solid benzoic acid that remains when all
the methylene chloride has evaporated was determined.

Part B Recrystallization of the Separated Components

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1. Benzoic acid was recrystallized from hexanes; useing approximately 1 mL for every 0.1 g of
crystals.

2. Naphthalene was recrystallized using a mix solvent.

3. Ethanol and water were the solvet pairs used. Naphthalene is readily soluble in ethanol and is
not soluble in water.

4. 0.1 g of naphthalene was added it was dissolved in the minimum amount of hot 95% ethanol.

5. Add water drop wise until the solution becomes cloudy while keeping the mixture warm.

6. Add a few drops of 95% ethanol to the cloudy solution until it is again clear, and then allow
the solution to cool undisturbed at room temperature. You should observe naphthalene
crystallizing out of the solution.

7. The flask was chilled on ice and isolates the crystals by vacuum filtration; rinse the crystals on
the filter paper with chilled 70% ethanol.

8. The yield and melting points of the purified compounds were determined, then they were in
the proper recovery jars.

Results and discussion:

The experiment begins with the preparation of benzoic acid and naphthalene mixed in

ether. Benzoic acid was massed out to 0.1064 g and naphthalene was massed out to 0.1083 g.

Sodium bicarbonate was then added 1.0 at a time to the solution. We observed a separation of an

aqueous layer and organic layer by identifying a thin line in the middle of the two layer. This

line indicated that the two layers had properly separated. The bottom layer was identified to be

the aqueous layer. Benzoic acid combined with sodium bicarbonate creates sodium benzoate

which is denser than naphthalene combined with ether. Therefore the top layer is the organic

layer containing naphthalene with ether solution. After removing the aqueous layer out and

separating the aqueous layer from organic layer we were left with two different solutions that

needed extraction.
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After the extraction methods were performed on the organic layer which had naphthalene

with ether we were able to calculate our percentage recovered. The naphthalene was observed to

be a white powdery substance within the test tube.

𝑦𝑖𝑒𝑙𝑑 0.0074𝑔
𝑥100 = 6.83% 𝑛𝑎𝑝𝑡ℎ𝑒𝑙𝑒𝑛𝑒 𝑟𝑒𝑐𝑜𝑣𝑒𝑟𝑒𝑑.
𝑖𝑛𝑖𝑡𝑖𝑎𝑙 0.1083𝑔

After the extraction methods were performed on the aqueous layer which had sodium

benzoate we were able to calculate our percentage recovered. The benzoic acid was observed

turned into a white precipitate with each addition of hydrochloric acid.

𝑦𝑖𝑒𝑙𝑑 0.0612𝑔
𝑥100 = 54.3% 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑 𝑟𝑒𝑐𝑜𝑣𝑒𝑟𝑒𝑑.
𝑖𝑛𝑖𝑡𝑖𝑎𝑙 0.1128𝑔

Chart 2 - Flow of Benzoic Acid and Naphthalene in Ether

For the experiment performed benzoic acid and naphthalene were dissolved in ether. The

organic layer which contained naphthalene, a neutral compound, and ether were very easy to
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extract. The procedure required that the ether be boiled off in boiling water then vacuumed to

boil any remaining ether at room temperature. (Murphy)The experimental results for percent

recovered were low at less than 6%. Such a low percent recovery is a cause for concern and

requires thought as to why such a low yield resulted and what the errors may have been.

Understanding the experiment and characteristics of naphthalene may help identify the error. The

organic layer was contained in a test tube which was boiled in a flask of water. Inside the test

tube a metal stir bar was placed in order to prevent bumping and also to ensure an even boiling

of the ether. Additionally it was noted that that we may have boiled the naphthalene/ether

solution slightly longer than prescribed by the lab procedure. (Williamson, 1989). Benzoic acid

when combined with sodium bicarbonate will result in the formation of sodium benzoate along

with water and carbon dioxide. We attempted to extract benzoic acid as a salt form using this

technique. Sodium bicarbonate, a weak inorganic base, was specifically used because NaOH

would be too strong a base and react with other compounds thus not separating into layers. The

sodium bicarbonate would deprotonate and ionized benzoic acid. This puts sodium benzoate into

the aqueous layer. This aqueous layer was pipetted out and placed in a side flask to be used later.

The reaction can be charter in equation 1 and mechanism 1.

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Sodium benzoate is the salt of a benzoic acid. In water sodium benzoate hydrolyses to

form a sodium hydroxide and benzoic acid. Since benzoic acid is a weak acid it will be partially

ionized in water and sodium hydroxide will be fully ionized. (Bacher). The result is an alkaline

solution due to having more hydroxyl ions than hydrogen ions. When we add hydrochloric acid

the compound undergoes an acid base reaction which forms sodium chloride salt and re-forming

the benzoic acid. This can be seen in equation 2 and mechanism 2.

However, a catastrophic error occurred when we attempted to extract benzoic acid from

the sodium benzoate using hydrochloric acid. When our group attempted to re-form the benzoic

acid by dropping hydrochloric acid into the solution nothing occurred. We attempted to continue

adding even more hydrochloric acid than prescribed but still no reaction. Investigating the error

we first assumed that we misplaced our beaker that held the sodium benzoate with another. To

test this theory we added hydrochloric acid to every beaker that we had which contained a liquid.

No reaction occurred on any of them. (Murphy)To continue investigating the cause of the error

we charted each step of the experiment to understand where we may have made an error. We

came up with several theories such as accidentally adding double the naphthalene and no benzoic

acid in the initial stage or accidentally dumping the sodium benzoate. The error could not be
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identified much to the disappointment of our group. Therefore we attribute the catastrophic

failure to human error.

Conclusion:

𝑦𝑖𝑒𝑙𝑑 0.0074𝑔
𝑥100 = 6.83% 𝑛𝑎𝑝𝑡ℎ𝑒𝑙𝑒𝑛𝑒 𝑟𝑒𝑐𝑜𝑣𝑒𝑟𝑒𝑑.
𝑖𝑛𝑖𝑡𝑖𝑎𝑙 0.1083𝑔

𝑦𝑖𝑒𝑙𝑑 0.0612𝑔
𝑥100 = 54.3% 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑 𝑟𝑒𝑐𝑜𝑣𝑒𝑟𝑒𝑑.
𝑖𝑛𝑖𝑡𝑖𝑎𝑙 0.1128𝑔
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References:

Bacher, A. (2013, December 30). Extraction in Theory and Practice (Part I). Retrieved

October 5, 2015, from http://www.chem.ucla.edu/~bacher/Specialtopics/extraction.html

Murphy, T. (n.d.). Extraction. Retrieved October 5, 2015, from

http://www.wfu.edu/chemistry/courses/organic/extract/extraction.htm

Williamson, K., & Masters, K. (1989). Macroscale and microscale organic experiments

(6th ed.). Lexington, Mass.: D.C. Heath.