By F.G.A. Stone, Robert West (Eds.)
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Additional info for Advances in Organometallic Chemistry, Vol. 17: Catalysis and Organic Syntheses
Sample text
0 X A4 Rh for reaction at 85"C, 1500 psi 1/1 HJCO. An increase in CO pressure increased the concentration of rhodium in solution, and an increase in temperature sharply decreased the metal concentration. These are understood as factors that influence the equilibrium between phosphine and carbonyl complexes. For amine resins, an additional implication was the fact that partial reduction of aldehyde to alcohol occurred and further changed the solvent polarity. Some pertinent data are summarized in Table XXXII.
Table reprinted with permission from J . Org. Chem. 34, 327 (1969). Copyright by the American Chemical Society. 25 Hydroformylation T A B L E XI11 HYDROFORMYLATION OF 1-OCTENE WITH VARIOUS Hz/CO RATIOS"(5'9) RhiC (g) Reaction time (min) % Aldehyde which H,/CO Ratio Iil 311 113 15 10 10 30 30 60 86 90 75 is straight-chain 'I Octene, 112 g ; 5% RhlC. 10-15 g; toluene, 200 ml; triphenyl phosphite, 15 g; temperature. 90°C; pressure, 80-100 psi. addition to affording improved isomer ratios, the reaction proceeded under conditions of temperature which were much milder than those effective with cobalt or even phosphine-modified cobalt catalysts.
Rc,s. L k v 8, 291 (1969). Copyright by the American Chemical Society. '' '-Ethylpentanal. 32 ROY L. 0 Y Y 2 a 3 u.. 9. Effect of solvent variation on hydroformylation of 1-hexene. Reprinted with permissionfromlnd. Eng. , Prod. Res. Dev. 8,291 (1969). Copyright by the American Chemical Society. Thus, the rule of Keulemans (49), that a-quaternary carbon formyl compounds are not formed, was followed. The olefin isomerized to allow formyl attachment to a primary carbon atom. Addition of phosphine, which decreases isomerization.