Phenol

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Introduction

Phenol is a colorless to pale pink crystalline solid with a sweet, pungent odor. Exposure to phenol may irritate the skin, eyes, nose, throat, and nervous system. Phenol molecules consist of hydroxyl groups directly attached to benzene rings. Due to the stability of the benzene ring, the phenol structure hardly converts into the ketone structure. The oxygen atom of the phenolic hydroxyl group adopts sp2 hybridization, providing a pair of lone electrons to form a delocalized bond with the six carbon atoms of the benzene ring. The large π bond strengthens the acidity of the enol, and the electron-pushing effect of the hydroxyl group strengthens the polarity of the O-H bond, so that the hydrogen of the hydroxyl group in the phenol can be ionized.

Phenol

Reactions of Phenols

Most of the chemical properties of phenols are similar to alcohols. For example, phenols react with acids to form esters. The phenoxide ion (ArO-) can be a good nucleophile in the synthesis of Williamson ethers. Due to the benzene ring structure, phenol can undergo electrophilic substitution reactions similar to benzene, such as nitration and halogenation. Compared with the electrophilic substitution reaction of the benzene ring, the substitution on the phenol ring is much easier, which is due to the electron-donating effect of the hydroxyl group, which increases the electron cloud density of the benzene ring. The hydrogen atoms on the phenolic hydroxyl groups of phenol can be replaced by carbon-containing groups to form ethers or esters. In addition, phenol can also undergo condensation reaction with formaldehyde under the catalysis of acid or base to form phenolic resin.

Applications

10-Phenol-1Phenols are widely used in household products and as intermediates in industrial synthesis. For example, phenol (in low concentrations) is used as a disinfectant in household cleaners and mouthwashes. In addition, phenol can be used in medicine to make fungicides, antiseptics and disinfectants. Less toxic phenols, such as n-hexylresorcinol, have replaced phenol in cough suppressants and other preservative applications; butylated hydroxytoluene (BHT) is much less toxic than phenol and is commonly found in food of antioxidants.

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