New water soluble chelating phosphines for aqueous phase catalysis

The syntheses of two chelating phosphines with pendant groups -p-C6H4-(CH2)(3)-C6H5, 2,2'-bis{di[p-(3-phenylpropyl)phenyl]phosphino}-1,1'-binaphthalene (BINAP type phosphine) and 2,2'-bis{di[p-(3-phenylpropyl)phenyl]phosphinomethyl}-1,1'-biphenyl}-1,1'-biphenyl (BISBI type phosphine), are described. These phosphines are further sulfonated with concentrated H2SO4 under mild conditions to yield their tetrasulfonated water soluble analogs, Two phase hydroformylation of octene-1 with in situ rhodium catalyst of the water soluble phosphines is investigated. The results indicate that the rhodium catalyst with sulfonated BISBI type phosphine offers both good activity under two phase conditions, due to the surface activity of the phosphine and excellent selectivity (97% of l-nonanal, at Rh/P ratio of 1/9).