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
4 " 2-Methylhexanal. Table reprinted with permission from Ind. Eng. C h r m . Prod. 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.
The total rate of reaction was also decreased with excess phosphine, but not to an excessive degree over the range studied. The above conclusions were applicable to 1 : 1 mixtures of hydrogen and carbon monoxide. A ratio of 2/1 HJCO resulted in higher reaction rates and higher isomer ratios, and it also dramatically increased the undesirable hydrogenation and isomerization reactions. Some quantitative data for these trends are given in Table XVI. JCO. Table reprinted with permission from J. Chem.
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. resulted in no reaction. B. Cyclic Olefins Differences in reactivity have been exhibited between acyclic and different types of cyclic olefins. Vinylcyclohexene in a cobalt hydroformylation at 120"-134°C and 475-720 atm pressure gave a 65% yield of a mixture of mono- and dialdehydes (66).