Benzotrichloride
Encyclopedia
Benzotrichloride, also known as trichlorotoluene is an organic compound
with the formula
C6H5CCl3. It is principally used as an intermediate in the preparation of other chemical products such as dyes.
of toluene
, catalysed by light or radical initiator
s such as dibenzoyl peroxide. Two intermediates are observed:
Benzotrichloride is hydrolysed
to benzoyl chloride
:
It is also transformed into benzotrifluoride, a precursor to pesticides:
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
C6H5CCl3. It is principally used as an intermediate in the preparation of other chemical products such as dyes.
Production and uses
Benzotrichloride is produced by the free radical chlorinationChlorination
Chlorination is the process of adding the element chlorine to water as a method of water purification to make it fit for human consumption as drinking water...
of toluene
Toluene
Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...
, catalysed by light or radical initiator
Radical initiator
In chemistry, radical initiators are substances that can produce radical species under mild conditions and promote radical reactions . These substances generally possess weak bonds—bonds that have small bond dissociation energies. Radical initiators are utilized in industrial processes such...
s such as dibenzoyl peroxide. Two intermediates are observed:
- C6H5CH3 + Cl2 → C6H5CH2ClBenzyl chlorideBenzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colourless liquid is a reactive organochlorine compound that is a widely used chemical building block.-Preparation:...
+ HCl - C6H5CH2Cl + Cl2 → C6H5CHCl2Benzal chlorideBenzal chloride is an organic compound with the formula C6H5CHCl2. This colourless liquid is a lachrymator and is used as a building block in organic synthesis....
+ HCl - C6H5CHCl2 + Cl2 → C6H5CCl3 + HCl
Benzotrichloride is hydrolysed
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
to benzoyl chloride
Benzoyl chloride
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C6H5COCl. It is a colourless, fuming liquid with an irritating odour...
:
- C6H5CCl3 + H2O → C6H5C(O)Cl + 2 HCl
It is also transformed into benzotrifluoride, a precursor to pesticides:
- C6H5CCl3 + 3 KF → C6H5CF3 + 3 KCl