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Phenol

What is phenol?

Phenol is a colorless aromatic organic compound with the molecular formula C6H5OH. The structure of phenol contains one hydroxyl group directly attached to the benzene ring. It is a crystalline solid which turns pink on exposure to air or light. It behaves like a weak acid due to losing one hydrogen ion to form a phenoxide anion. The acidity of phenol can be explained by the stability or resonance of phenoxide ion. Phenol is moderately soluble in cold water but solubility increases in ethanol or ether solution due to the presence of a benzene ring. Phenol is used as an antiseptic and disinfectant. It is also used for the production of dyes, drugs, and phenol-formaldehyde resin or bakelite. It can be extracted first from coal tar but today it can be extracted commercially by the cumene phenol process.

Structure of phenol

The structure of phenol contains a benzene ring which is directly attached to a hydroxyl group.

Phenol structure, chemical properties such as acidity and solubility in water solution and uses

Properties of phenol

It is monohydric aromatic alcohol that is moderately soluble in cold water but readily soluble in ethanol or ether. It is a stronger acid than alcohol due to the resonance structure or formation of a phenoxide anion. The infrared absorption region of the phenolic hydroxyl group is the same as that of the alcoholic hydroxyl group. They can be differentiated by their nucleus which has its own absorption spectrum. Some common properties of disinfectant phenol are given below the table,

Properties of phenol
IUPAC name benzenol
Chemical formula C6H6O
Molar mass 94.113 g/mol
Appearance colorless crystalline solid
Density 1.07 g/cm3
Melting point 40.5 °C
Boiling point 181.7 °C
Conjugate base Phenoxide ion (C6H5O)
Dipole moment 1.224 D
Solubility in water 8.3 g/100 mL

Boiling point

Like other alcohol, phenol molecules are associated through intermolecular hydrogen bonding which extends over a chain. Therefore, the boiling point of phenol is much higher than the expected value obtained from their molecular weight.

Acidity of phenol

The acidity of phenol is weaker than carboxylic acids but stronger than alcohols. Due to resonance, the oxygen atom of the hydroxyl group acquires a positive charge. Therefore, it can be facilitated the release of the proton.

Acidity and resonace of phenol and phenoxide ion

The acidity of phenol is also explained by the stability of the phenoxide anion. The phenoxide ion has also resonance structures. It is more stabilized by resonance than the un-ionized phenol molecule due to the spreading of the negative charge.

Solubility of phenol in water

The solubility of phenol in water can be explained by hydrogen bonding with water molecules. Like other alcohol, it can also form hydrogen bonds with water molecules. The solubility of phenol is much less than that of other alcohol due to the presence of the benzene ring. With the increasing hydroxyl group, the solubility of phenol in water increases.

Chemical reactions

Most of the reactions of phenol are connected with the benzene ring rather than the hydroxyl group.

  • It gives violet colour with ferric chloride.
  • Phenol behaves as a weak acid and formed phenoxide salts with strong alkalies.
    C6H5OH + NaOH → C6H5ONa + H2O
    Alkali phenoxide reacts with alkali halide to form the phenolic esters.
  • It forms phenyl esters when warmed with an acid chloride or acid anhydride.
    C6H5OH + (CH3CO)2O → CH3COOC6H5 + CH3COOH
  • Many of the reactions of phenol are carried out by electrophilic aromatic substitution in ortho and para positions. For example, the alkylation of phenol forms p-derivative with a small amount of o-derivative.
  • It can be hydrogenated in presence of a nickel catalyst at 160 °C to form cyclohexanol.
    C6H5OH + 3H2 → C6H11OH

Phenol formaldehyde resin

At low temperature, in presence of dilute acid or alkali phenol condensed with formalin solution which contains 40 percent aqueous formaldehyde to form ortho and para-hydroxy benzyl alcohol. It is the basis of the preparation of phenol-formaldehyde resin or Bakelite.

Phenol formaldehyde Reaction and resin or Bakelite

Production Process

It can be first extracted from coal tar. It is the oldest method for the extraction of phenol. But such type of extraction is now insufficient to give the required amount of phenol for the industry. Therefore, we prepared it synthetically. The cumene phenol process is the most important process for the production of phenol. It is carried out by the oxidation of cumene to its hydroperoxide. It is decomposed by acid to form phenol and acetone. Both the products have commercial importance.

Cumene process for production

It is also prepared by oxidation of toluene by air in the presence of a chemical catalyst such as manganous or cupric salts.
C6H5CH3 → C6H5OH + CO2

It is produced by the steam distillation of benzene diazonium sulfate solution.
C6H5N2HSO4 + H2O → C6H5OH + N2 + H2SO4

It may be prepared by fusion of sodium benzyl sulphonate with sodium hydroxide. It is an early commercial route for the production of phenol.
C6H5SO3Na + 2NaOH → C6H5ONa + Na2SO3 + H2O

What is phenol used for?

  • A major part of phenol can be used for phenolic resins. It is the base material for the manufacture of nylon and other synthetic fibers. Phenolic resins can be prepared by the reactions of phenolic compounds with formaldehyde. The most famous example of phenolic resins is Bakelite.
  • Phenol–chloroform extraction technique in molecular biology is used for the separation of nucleic acids such as DNA and RNA from proteins and lipids.
  • It is also used for the production of different types of household products, antiseptics, and disinfectants. Phenol is the first antiseptic and disinfectant which we used in the surgical instruments.
  • Phenolic compounds such as salicylic acid, salol, aspirin, methyl salicylate, and phenacetin can be used for making different types of drugs in the pharmaceuticals industry.
  • Due to antiseptic and disinfectant properties, phenol is used for the production of different types of cosmetics like carbolic soap, sunscreens, hair colorings, skin lightening, or toners. Such types of use can be banned by European Union and Canada due to their safety concerns.
  • Phenol can be used for the production of explosive picric acid, indicator phenolphthalein, and solvent cyclohexanol.