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Issue 9, 2010
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Phosphonium nitrate ionic liquid catalysed electrophilic aromatic oxychlorination

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Abstract

Trioctylmethylphosphonium nitrate (P8,8,8,1NO3), an ionic liquid made via a green synthesis, catalyses electrophilic aromatic chlorination of arenes with HCl and air at 80 °C. The aromatic oxychlorination is truly catalytic in nitrate, proceeds without added solvents, and uses atmospheric oxygen as oxidant. The extent of chlorination can be controlled to yield selectively mono or dichlorinated products, and the ionic liquid catalyst can be recycled. Dependence of the chlorination rate on HCl and nitrate concentrations as well as on the rate of re-oxidation of the nitrogen intermediates by air, allowed us to propose a reaction mechanism.

Graphical abstract: Phosphonium nitrate ionic liquid catalysed electrophilic aromatic oxychlorination

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Supplementary files

Article information


Submitted
15 Apr 2010
Accepted
13 Jul 2010
First published
05 Aug 2010

Green Chem., 2010,12, 1654-1660
Article type
Paper

Phosphonium nitrate ionic liquid catalysed electrophilic aromatic oxychlorination

M. Noè, A. Perosa, M. Selva and L. Zambelli, Green Chem., 2010, 12, 1654 DOI: 10.1039/C0GC00004C

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