Benzotrichloride
chemical compound
Benzotrichloride (BTC), also known as α,α,α-trichlorotoluene, phenyl chloroform or (trichloromethyl)benzene, is an organic compound with the formula C6H5CCl3. Benzotrichloride is an unstable, colorless or somewhat yellowish, viscous, chlorinated hydrocarbon with a penetrating odor. Benzotrichloride is used extensively as a chemical intermediate for products of various classes, i.e. dyes and antimicrobial agents.
Structure and reactivity
Benzotrichloride is a poorly water-soluble, clear to yellowish liquid with a penetrating odor. It hydrolyzes rapidly to benzoic acid and hydrochloric acid with a half life of about 2.4 minutes, thus making the compound unstable in the presence of water. In other chemical reactions, benzotrichloride reacts at the chlorinated α-carbon, for example in substitution reactions. It is used as an intermediate in the synthesis of benzoyl chloride, benzotrifluoride and 2,4-dihydroxybenzophenone which in turn are also intermediates in other reactions:
C6H5CCl3 + resorcinol → 2,4-dihydroxybenzophenone
C6H5CCl3 + H2O → C6H5C(O)Cl + 2 HCl
C6H5CCl3 + 3 KF → C6H5CF3 + 3 KCl
These compounds are further used to synthesize chemicals needed in the pharmaceutical industry (benzoyl peroxide), the synthesis of pesticides, dyes and UV-absorbing compounds which are often used in paint and plastics to prevent degradation by sunlight.
Production
Production capacity of benzotrichloride was estimated at 80,000 tonnes for the year 2000. It is produced by the free radical chlorination of toluene, catalysed by light or radical initiators such as dibenzoyl peroxide.
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