Simplification of the synthesis of the reversible addition–fragmentation chain transfer agent 2-(2-cyanopropyl)-dithiobenzoate

Abstract

The general literature procedure for the preparation of the reversible addition–fragmentation chain transfer (RAFT) agent 2-(2-cyanopropyl)-dithiobenzoate (CPDB) was modified by omitting the recrystallisation of the intermediate di(thiobenzoyl)disulphide. The yield of the CPDB in the simplified synthesis was increased four times compared to the standard one. The behaviour of the CPDB obtained by the modified procedure and by the standard one in the polymerisation of methyl methacrylate was investigated. The CPDB synthesized by the simplified procedure showed itself to be a good RAFT agent, giving excellent control over the polymerisation of methyl methacrylate and it behaved in the same manner as the CPDB prepared by the literature method. The obtained poly(methyl methacrylate) had a narrow molecular weight distibution (PD = 1.1).

Keywords

• 2-(2-cyanopropyl)-dithiobenzoate
• preparation
• reversible addition–fragmentation chain transfer
• poly(methyl methacrylate)