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Original Articles

Synthesis of Dichlorophenylphosphine via a Friedel-Crafts Reaction in [Et4N]Br-XAlCl3 Ionic Liquids

, &
Pages 2667-2677 | Received 14 Sep 2004, Accepted 18 Dec 2004, Published online: 19 Aug 2006
 

The Friedel-Crafts reaction of phosphorus trichloride and benzene in [Et 4 N]Br-XAlCl 3 ([Et 4 N]Br = tetraethylammonium bromide) ionic liquids (ILs) was investigated for the clean synthesis of dichlorophenylphosphine (DCPP). A simple product isolation procedure was achieved, and the effects of IL's composition, reaction time, and quantity on this reaction were studied. The [Et 4 N]Br-XAlCl 3 ILs gave this reaction a green character. From the isolation experiments, it was found that (a) because of the formation of the complex of DCPP and AlCl 3 , the catalytic activity of the [Et 3 NH]Cl-XAlCl 3 ([Et 3 NH]Cl = triethylhydrogenamonium chloride) was reduced; (b) with the addition of quaternary ammonium to the IL's residue, additional DCPP could be recovered.

Notes

a ILs: [Et4N]Br-2AlCl3.

a Reactions were carried out with refluxing for 6 h.

a The recovery of DCPP is calculated based on the DCPP used in the preparation of complex.

b The recovery of DCPP is calculated based on the weight increase of the IL residue after each reaction.

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