Thermoregulated phase transfer ligands and catalysis XIV: Synthesis of N,N-dipolyoxyethylene-substituted-4-(diphenylphosphino) benzenesulfonamide (PEO-DPPSA) and the catalytic activity of its rhodium complex in hydroformylation of 1-decene

Abstract

A novel water soluble phosphine, N,N-dipolyoxyethylene-substituted-4-(diphenylphosphino) benzenesulfonamide (PEO-DPPSA), is synthesized by ethoxylation of 4-(diphenylphosphino) benzenesulfonamide Ph 2P–C 6H 4SO 2NH 2 (DPPSA) obtained from palladium-catalyzed P–C coupling reaction between 4-I–C 6H 4SO 2NH 2 and Ph 2PH. The PEO-DPPSA possesses the same property of inverse temperature-dependent solubility in water (cloud point, C p) as nonionic surfactants. Investigation on the behavior of RhCl 3·3H 2O/PEO-DPPSA complex in the aqueous–organic biphasic hydroformylation of 1-decene showed that the complex exhibited high catalytic activity. The conversion of 1-decene and the yield of aldehydes reach as high as 97.8 and 95.6%, respectively, under optimized conditions. The high reactivity of Rh/PEO-DPPSA complex can be attributed to a process termed thermoregulated phase transfer catalysis.