By F.G.A. Stone and Robert West (Eds.)
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M O Mnormal products x 100/mol% normal plus mol% branched products. Time to consume 4 of the total gas reacted during the run. H,/CO = I , only 87% conversion of the I-hexene occurred overnight, also incomplete hydrogenation of the RCHO product to RCH,OH. 'I 1. Further progress in providing linear aldehydes from olefinic substrates has been provided by modified rhodium catalysts. Without modifiers, the product from the hydroformylation has very low normal : is0 isomer ratios; I-octene gave only 31% of the linear isomers in one example (28).
CH$H =CHCOOC ,H -[ CH,CHC H,COOC,H, I CHO + CH,C H,CH,COOC ,H5 I CHO 1 With rhodium catalysts, higher amounts of the lactone which is formed ROY L. PRUETT 36 from the p-formylated product (13) were observed (70), as shown in Table XXIII. At the lowest temperature, appreciable amounts of the aisomer were noted. At the higher temperatures, y-formylation resulting from isomerization was noted, although the quantity was much less significant than that found with cobalt catalyst. Again, addition of trialkylphosphine was found to be effective for reducing the amount of products obtained by attaching a formyl group to a carbon other than that of the original carbonxarbon double bond (73).
25 ml. Table reprinted with permission from Ind. E n g . Chem.. Prod. Res. Dev. 8, 291 (1969). Copyright by the American Chemical Society. -Methylhexanal. 2-Ethylpentanal. carbon atoms affects both the rate of reaction and the product distribution. 2-Methyl-1-pentene reacts at about half the rate of I-hexene ( 4 8 ) , 2,3-dimethylbutene at one-eightieth the rate. In addition, the product from the latter obtained by reaction at 140°C, 160 atm of H,/CO, and Rh,O, as catalyst consisted almost entirely of 3,4-dimethylpentanol ( 6 5 ) .