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By F.G.A. Stone and Robert West (Eds.)

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As noted before, the formyl group can be attached to either of the carbon atoms which constitute the original double bond. For olefins of greater than C , chain length, the formyl group may, under certain conditions, also be attached to a carbon atom which was originally saturated. But for propylene only two isomers are possible, as shown in Eq. (25). ] CH,CHCHO + CH,CH,CH,CHO I c H3 (25) As a result of the desire for obtaining as much of the linear isomer as ROY L. PRUETT 18 possible, both cobalt and rhodium hydroformylations have been studied with product composition as the goal.

0, catalyst [Co,(CO), + 2(n-C4H,),P]. Under the same conditions except at a temperature of 190°C, the n-hexanol was 84% of the hexyl alcohol produced. In addition to the increased proportion of linear product, other differences from the unmodified cobalt-catalyzed reaction may be noted. 0 Equiv. 9 Reaction conditions: propylene, 20 g; ethanol, 80 g; ethyl orthoformate, 90 g; PHs,80 atm; Pco. 230 atm; temperature, 110°C. Hydroformy lation 21 pressure of 500 psi is significantly less than that employed in processes using CO,(CO)~[or HCo(CO),] as catalyst.

9. The rate of gas uptake is plotted as a function of time for a reaction conducted in benzene and again for a second reaction conducted in butyraldehyde. The rate of reaction in the polar solvent was initially fast and decreased with time. The rate in the nonpolar benzene was initially slow, became faster as the solvent became more polar with the presence of product aldehyde, and then subsequently diminished with time. When the data were replotted as the log of unreacted olefin vs. time, the polar medium reaction showed first-order dependence on olefin concentration, whereas the nonpolar solvent reaction showed no definite order, owing to the constantly changing polarity.

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