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Extra resources for Catalysis and Organic Syntheses
Falbe and Korte (90) studied the cobalt hydroformylation of dihydropyran and its derivatives. The reactions were conducted at temperatures above 18O"C, with pressures of 300 atm of 1/1 H,/CO. Under these conditions, the initially formed aldehydes were hydrogenated to the alcohols in situ. As noted with acyclic vinyl ethers, formyl attachment was predominantly a. 77% Substitution on the double-bond carbon a to the oxygen increased the difficulty of the reaction, and formyl attachment occurred exclusively on the p-carbon [Eq.
The hydrogen partial pressure has a small but reproducible effect on the hydroformylation product composition. The direction of the change found was the same as for carbon monoxide partial pressures: the higher PH2 experiments gave higher percentages of n-aldehyde. Conflicting results have been reported for the effects of catalyst concentration in the cobalt-catalyzed reaction. 80 atm; temperature, 80°C. 6 28. 2 5. I 5. 05 g ; benzene, 27 g; PHz,80 atm; temperature, 80°C. A = % n-hexanal of total aldehydes formed: B and C = % 2-methylpentanal and 2-ethylbutanal.
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. 7 X lo-* M ;pressure, 500 psi 1/1 H,/CO; temperature, 100°C; reaction time, 17 hours; solvent, 50 ml benzene; olefin, 25 ml 1-hexene. Table reprinted with permission from Ind. Eng. , Prod. Res. 8,291 (1969). Copyright by the American Chemical Society. 2-Methylhexanal. 2-Ethylpentanal. Percent of total aldehyde which is I-heptanal.