Hydrogenation and hydroformylation of C-4 unsaturated alcohols with an [Rb(acac)(CO)(2)]/PNS catalyst in water solution (PNS =Ph-2 PCH2CH2CONHC(CH3)(2)CH2SO3Li)

A catalytic system containing [Rh(acac)(CO)(2)] and water soluble phosphine PNS (PNS=Ph2PCH2CH2- CONHC(CH3)(2)CH2SO3Li) was used for the hydrogenation and hydroformylation of C-4 unsaturated alcohols: 1-buten-3-ol (CH2 = CHCH (CH3)OH) (1), 2-methyl-2-propen-1-ol (CH2 =C(CH3)CH2OH) (2) and 2-buten-1-o l (CH3CH=CHCH2OH) (3) in water. The most reactive substrate, (1), with a te rminal double bond, is hydrogenated at 313 K and 0.1 MPa of H-2 pressure gi ving 92% of 2-methyl-propanol after 4 h. The hydrogenation of (2) and (3) w ith, respectively, 74% and 65% yields was performed at 353 K and 0.5 MPa of H-2 pressure. The main products of the hydroformylation of (1), (2) and (3 ) alcohols are 2-hydroxytetrahydrofuran derivatives formed by hydroxyaldehy de cyclization. The hydroformylation of (1) gave 81-95% of 2-hydroxy-5-meth yl-tetrahydrofuran at 323-353 K and 1 MPa CO/H-2 regardless of the PNS conc entration. In the hydroformylation of (2) and (3) the highest yield of prod ucts, respectively 92 and 77%, was achieved at 353 K, 1 MPa and [PNS]: [Rh] = 3. During the reaction a pH decrease was noted. (C) 1999 Elsevier Scienc e B.V. All nights reserved.