Electrophilic chlorination of arenes with trichloroisocyanuric acid over acid zeolites

• Safe and cheap chlorination process of arenes.
• Use of friendly solid acids instead of liquid acids.
• HUSY zeolite is the better catalyst for chlorination of toluene (100%), chlorobenzene (72%) and nitrobenzene (53%).
• DFT calculations allow to describe all the reaction steps occurring within the zeolite frame.

Trichloroisocyanuric acid (TCCA) reacts with arenes and its reactivity is highly affected by the acid strength of the reaction medium. Deactivated arenes are efficiently chlorinated by TCCA in solid acids. Our experimental results, along with DFT calculations show that chlorination using solid acid catalysis is feasible, thus leading to possible replacement of strong liquid acids used to promote this superelectrophilic reaction. We have tested several solid acids, showing the synergic need for acid strength and pore size for promoting the reaction.

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