By F.G.A. Stone, Robert West (Eds.)
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2753 (1970). Copyright by the Chemical Society. Rate measured as gas uptake in ml min-I. 60 ml min-I, respectively. 5 <4 <4 <4 ca 4 10 22 60 31 HRh(CO)(PPh,),, 30 mM; benzene solvent; substrate concentration, I M : I atm HJCO. peratures of 25", 45",and 65"C, with no excess phosphine, and a gas ratio of 1/1 H,/CO. Low isomer ratios of ( 2 - 4 ) : 1 were obtained. When the gas ratio was 2/1, the isomer ratio was still low and the competing hydrogenation and isomerization reactions were serious. However, conducting the reaction with a 100-fold molar excess of triphenylphosphine gave a slightly higher isomer ratio ( 5 .
43): By careful control of reaction conditions, modest yields of the intermediate aldehyde could be obtained. E. 3-Butadiene, the simplest conjugated diene, appears to be a promising substrate for the hydroformylation reaction, because the expected product (hexanedial) could be easily converted to useful products. Oxidation would produce adipic acid, hydrogenation hexanediol, and reductive amination hexamethylenediamine. However, this objective has been difficult to realize. It has been established that the cobalt hydrocarbonyl adds to form a stable wallyl complex (93, 94).
PRUETT 42 substrates with both rhodium and cobalt catalysts have been made (87); the results are given in Table XXIX. Similar results with ally1 alcohol were obtained by Kawahito and Ikeda (88). A rhodium tributylphosphine system gave 66% 1,Cbutanediol and 22% 2-methyl- I-3-propanediol. D. Unsaturated Ethers and Alkenyl Esters Early studies of the cobalt hydroformylation (4) included vinyl acetate as the olefinic reactant. A mixture of a-and p-formyl esters was reported. CH,COOCH=CH, + CO + CO,(CO),~ CH,COOCHCH, €I, I + CH3COOCH,CHzCH0 CHO P, a , 30% 2% Essentially the same results were obtained in a later study (89).