Surface active phosphines for catalysis under two-phase reaction conditions. P(menthyl) [(CH 2) 8C 6H 4- p-SO 3Na] 2 and the hydroformylation of styrene

Abstract

The novel optically active phosphine, bis(8-phenyloctyl) (Menth) phosphine, (Menth = 1 R,3 R,4 S( - )menthyl) is synthesized and sulfonated under mild conditions to yield the corresponding sulfonated phosphine, disodium bis-(8-( para-sulfonatophenyl)octyl) (Menth) phosphine. The water soluble phosphine is used to generate an aqueous-methanol rhodium catalyst for the hydroformylation of styrene. The catalyst shows high catalytic activity, but virtually no optical induction. Normal to branch ratios for the hydroformylation of styrene are in the range 0.35 to 0.5. The catalytic data with TPPTS is given for comparison. TPPTS yields catalysts that are less active under two phase reaction conditions and slightly less selective for formation of 2-phenylpropanal.