Jasmine Carter

September 28, 2017

Synthesis of Benzoic Acid

Claflin University

CHEM 231_03 L

Instructor: Mr. N. Ahmad

ABSTRACT

The purpose of the experiment was to prepare benzoic acid from impure sodium

benzoate, to calculate the percentage yield of the products, and to determine the melting point.

During the laboratory experiment, 2 grams of sodium benzoate was dissolved in water and the

solution was made to react with hydrochloric acid to form benzoic acid. The benzoic acid was

separated from the reaction mixture by vacuum filtration and it was dried and then weighed on

an electronic balance to calculate the percentage yield. A sample of the filtered substance of

benzoic acid was heated using a Mel – temperature apparatus to determine the melting point as

well. Therefore, the percentage yield of benzoic acid was calculated to be 95.5 % and the melting

point was determined to be 121.6 – 122.6˚C.

INTRODUCTION

A reaction mixture is product of the act or process or an instance of mixing and reacting two or

more substances together causing reaction. For instance, if sodium benzoate becomes protonated by

hydrochloric acid, it will form benzoic acid. To separate precipitates from mixtures, the process of

filtration can be performed. Filtration is a technique used either to remove solid impurities from an

organic solution or to isolate an organic solid. The two types of filtration commonly used in organic

chemistry laboratories are gravity filtration and vacuum filtration. To separate benzoic acid from a

reaction mixture, the process of vacuum filtration is commonly practiced. Vacuum filtration is a

chemistry laboratory technique which allows for a greater rate of filtration. Whereas in normal filtration,

gravity provides the force which draws the liquid through the filter paper, however, in vacuum filtration a

pressure gradient performs the function. Vacuum filtration has the advantage of offering a variable rate

depending on the strength of the pump being used to extract air from the Buchner flask. However, care

must be taken not to use such a strong vacuum that the filter paper rips which will cause all the solid to be

lost back into the solvent or in extreme cases the glass flask happens to break.

 Benzoic acid is a colorless crystalline solid that is the simplest aromatic carboxylic acid. Its

chemical formula is C6H5COOH. It is soluble in water, alcohol, benzene, and ether. Its aqua solution is

weakly acidic. It is non-toxic and stable under ordinary conditions. Benzoic acid occurs naturally in many

plants and resins. It is also detected in animals. The organic compound is an important precursor for the

synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates.

Its salts are used as a food preservative. Benzoic acid is produced commercially by partial oxidation of

toluene with oxygen. The process is catalyzed by cobalt or manganese naphthenate and uses cheap raw

materials since it is considered environmentally green.

EXPERIMENTAL PROCEDURE

2 grams of impure sodium benzoate was weighed on an electric balance and transferred in a 100

mL beaker. 10 mL of distilled water was measured and poured into the beaker. The sodium benzoate was

stirred until it was completely dissolved. 5 mL of 3M hydrochloric acid was measured and it was added

slowly until about 4 mL was added while the sodium benzoate solution was being stirred. More

hydrochloric acid was added while the solution was being stirred and the solution was tested frequently

with pH paper until the pH was 1. To test the pH, the stirring rod was utilized to transfer the drop of

supernatant liquid to the strip of pH paper. The addition of a little hydrochloric acid caused no harm. The

solution was cooled to 10˚C or below by setting the small beaker in a larger beaker which contained

crushed ice and a little water for approximately 5 – 10 minutes. If a new substance had formed, it was

separated from the reaction mixture by vacuum filtration. Therefore, it was washed with cold water for

purification and filtered and dried. Then, the benzoic acid was weighed on the electronic balance and the

resultant mass was utilized to determine the percentage yield. Furthermore, 2 – 3 mm of the benzoic acid

substance was obtained and placed into a capillary tube. The closed end of the capillary tube was dropped

through the stem of the inverted funnel. The tube bounced on the table which resulted in the powder being

tightly packed into the bottom of the tube. The capillary tube was placed in the Mel-temperature

apparatus chamber with its closed end pointed down. The switch was turned on and the power level was

set to obtain the desired heating rate. The start temperature was set to 80˚C and the stop temperature was

set to 150˚C. The ramp rate in which the temperature increased was set to 2˚C per minute. The sample

was observed continuously so that its respective melting point was not missed. The temperature was

recorded when the sample first started to melt and when the sample was completely melted. Once the

sample had melted, the power was turned off and the capillary tube was removed and disposed of in a

special container. However, the remainder of the benzoic acid substance was stored away for future

laboratory studies.
DATA

Mass of the Sodium Benzoate acid 2.04 g

Theoretical yield of Benzoic acid 1.728 g
Mass of Benzoic acid 1.65 g
Percentage yield of Benzoic acid 95.5%
Melting point of product 121.6 – 122.6˚C

CALCULATIONS

C6H5COONa + HCl → C6H5COOH + NaCl

Molar mass of C 6 H 5 COONa=( 7 •12.011 ) + ( 5 •1.008 )+ (2 •15.999 ) +22.990=144 g/mol

Molar mass of C 6 H 5 COO H=( 7 •12.011 )+ ( 6 •1.008 ) + ( 2• 15.999 )=1 22 g /mol

Mass of Sodium Benzoate acid = 2.04 g

1 mol
Theoretical yield=2.04 g ( 144 )g =0.01416 mol( 122 g
1 mol )
=1.728 g

Mass of Benzoic acid = 1.65 g

1.65 g
Percentage yield= •100=95.5 %
1.728 g
CONCLUSION

In essence, the experiment was proven to be successful based on the resulting data. For

instance, the actual yield (1.65 g) was lower than the theoretical yield (1.728 g) of benzoic acid.

Therefore, the percentage yield was calculated to be 95.5%. Also, the melting point of benzoic

acid was determined to be 121.6 – 122.6˚C, which indicates that the benzoic acid was purified

since pure substances have a sharp melting range of 1 – 2 degrees. Moreover, a source of error of

the experiment would be if the students did not weigh the sodium benzoate properly for

approximately 2 grams, then it would have led to inaccurate data because it would have yielded

an actual yield higher than the theoretical yield. Another source of error would be if the students

did not let the benzoic acid dry thoroughly, then it would have resulted in insufficient data as

well. Too, a source of error would be a defect in the electronic balances, which would cause an

inaccuracy in the students weighed mass of the benzoic acid for the actual yield. In addition, a

source of error would be if the capillary tube was filled with a sample larger than 2 – 3 mm, then

the sample would heat unevenly and result in an inaccurate melting point range determination.

Also, a source of error would be if the sample was not heated at a low ramp rate of about 2 ˚C

per minute, then the results would have yielded an inaccurate determination of the melting point.

Lastly, a source of error would be students’ inattentiveness to the capillary tube to determine

when the melting of the solid started and when it was completed. Because, if the students were

distracted while the solid had begun to melt, then there would be an inaccuracy in the melting

point determination.
REFERENCES

1. “Benzoic Acid.” The Chemical Company. The Chemical Company, n.d. Web. 28

September 2017.

2. “Filtration.” Organic Chemistry at CU Boulder. University of Colorado at Boulder, n.d.

Web. 28 September 2017.

3. “Reaction Mixture.” Wiktionary. MediaWiki, 26 May 2017. Web. 28 September 2017.