Synthesis and use as a catalyst support of porous polystyrene with bis(phosphonic acid)-functionalized surfaces

The synthesis of a novel polymerizable bis(phosphonic acid) monomer, 1-(3-vinylphenyl)-propane-2,3-bis(phosphonic acid), is reported. Highly porous cross-linked polystyrenes possessing surface-supported bis(phosphonic acid) groups were obtained by copolymerization of 6b with styrene and divinylbenzene. Two different methods were employed: first the polymerization of a bis(2-ethylhexyl) sulfosuccinate stabilized water/oil microemulsion in the presence of 6b; second the polymerization of the monomers in the presence of a pore-forming diluent. By both methods most of the functional groups were located on the pore surface. The best accessibility (75%) was obtained in the microemulsion polymerization. The porous polymer was ion-exchanged with Pd and used for the hydrogenation of 1-octene. The catalyst could be reused without regeneration and showed no sign of deactivation during 10 hydrogenation experiments. 14 refs., 5 figs., 3 tabs.