Diphosphine-rhodium complex-catalyzed hydroformylation of .ALPHA.,.BETA.-unsaturated esters.
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The product distribution in the hydroformylation of α,β-unsaturated esters (ethyl acrylate, methyl methacrylate, methyl crotonate, and methyl tiglate) catalyzed by Rh<SUB>2</SUB>Cl<SUB>2</SUB>(CO)<SUB>4</SUB> was studied at 150 °C under 100 atm of synthesis gas (CO/H<SUB>2</SUB>=1/1) in the absence or presence of various additional phosphorus ligands. In order to attain a high selectivity of α-formylation (>80%), the addition of shorter methylene-chained diphosphines (R<SUB>2</SUB>P(CH<SUB>2</SUB>)<I><SUB>n</SUB></I>PR<SUB>2</SUB>, R=phenyl or cyclohexyl, <I>n</I>=2–4) to the reaction system was essential, while the use of Rh<SUB>2</SUB>Cl<SUB>2</SUB>(CO)<SUB>4</SUB> alone or in combination with triphenylphosphine or a longer diphosphine, Ph<SUB>2</SUB>P(CH<SUB>2</SUB>)<SUB>5</SUB>PPh<SUB>2</SUB>, resulted in a very low α-selectivity. The effects of the reaction variables on the product distribution were also examined for acrylate and methacrylate using Ph<SUB>2</SUB>P(CH<SUB>2</SUB>)<SUB>4</SUB>PPh<SUB>2</SUB> and Ph<SUB>2</SUB>P(CH<SUB>2</SUB>)<SUB>2</SUB>PPh<SUB>2</SUB>, respectively, as additional ligands.
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