Benzoic Acid - C6H5COOH

What is Benzoic Acid?

Benzoic acid is an organic compound which is described by the chemical formula C6H5COOH. It consists of a carboxyl group attached to a benzene ring. Therefore, benzoic acid is said to be an aromatic carboxylic acid. This compound exists as a crystalline, colorless solid under normal conditions. The term ‘benzoate’ refers to the esters and salts of C6H5COOH.

The commercial production of benzoic acid is done via the partial oxidation of toluene with oxygen, catalyzed by manganese or cobalt naphthenates. This chemical reaction is illustrated below.

Benzoic Acid

Another industrial method of preparing benzoic acid is by reacting tri-chlorotoluene with calcium hydroxide in the presence of water, and the treatment of the calcium benzoate product with hydrochloric acid.

Structure

The structure of a C6H5COOH molecule is illustrated below. This molecule consists of a benzene ring to which a carboxyl functional group is linked. The molecule consists of 7 carbon atoms, 6 hydrogen atoms, and 2 oxygen atoms.

Benzoic Acid Structure

Properties of Benzoic Acid

The physical and chemical properties of C6H5COOH are discussed in this subsection.

Chemical Data

Benzoic Acid Formula C7H6O2 or C6H5COOH
Molecular Weight/ Molar Mass 122.12 g/mol
Density 1.27 g/cm3 at 15oC
Boiling Point 523K
Melting Point 395 K

Physical Properties

  • Benzoic acid has a colorless appearance in its solid state, which is of a crystalline nature.
  • The crystal structure is monoclinic.
  • The presence of the aromatic ring gives this compound a faintly pleasant odor.
  • At a temperature of 130oC, the density of this compound reduces to 1.075 grams per cubic centimeter.

Chemical Properties

  • It is soluble in water, and the solubility at 25oC and 100oC is 3.44 g/L and 56.31 g/L respectively.
  • It is soluble in benzene, carbon tetrachloride, acetone, and alcohols.
  • The acid dissociation constant (pKa) of benzoic acid corresponds to 4.2
  • Its reactions can occur at the carboxyl group or even at the aromatic ring.

Uses of Benzoic Acid

Some important uses of C6H5COOH are listed below.

  • The production of phenol involves the use of benzoic acid.
  • This compound is used in ointments that prevent or treat fungal skin diseases.
  • C6H5COOH is used as a preservative in the food industry.
  • Benzoic acid is an ingredient in many cosmetic products, such as lipsticks.
  • It is also a precursor to benzoyl chloride.
  • One of the components of toothpaste, mouthwash, and facewash creams is C6H5
  • This compound is also used in the manufacture of dyes and in insect repellants.

Frequently Asked Questions

What are the uses of benzoic acid?

The primary use of benzoic acid is in the industrial production of the aromatic compound phenol. This is done via a process known as oxidative decarboxylation. It can be noted that the ideal temperature under which this process can be carried out is in the range of 300 to 400 degrees celsius. Also, benzoic acid and its salts are widely used in the food industry as food preservatives.

Comment on the solubility of benzoic acid in water

Benzoic acid is not very soluble in water. However, the solubility of this compound in water increases when the temperature is increased (as is the case with most compounds). At a temperature of 0 degrees celsius, the solubility of benzoic acid in water corresponds to 1.7 grams per litre. When heated to 100 degrees celsius, the solubility of this compound in water increases to 56.31 grams per litre.

How can benzoic acid be prepared?

Industrially, benzoic acid can be prepared by employing oxygen gas for the partial oxidation of toluene. It can be noted that this process usually employs manganese or cobalt naphthenates as catalysts. This compound can also be prepared via the hydrolysis of benzamide and benzonitrile. It can also be prepared by oxidizing benzyl chloride or benzyl alcohol, or any other derivative of the benzyl group.

To learn more about this compound and other aromatic compounds, such as pyridine, register with BYJU’S and download the mobile application on your smartphone.

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