Hydroformylation of 1-Undecene Catalyzed by [Rh (Ph2N3) (CO) (PPh3) 2]
Tetsuya YONEDA and Noriyuki KAMEDA*
Department of Chemistry, College of Science and Technology, Nihon University; Narashinodai, Funabashi-shi 274-8501 Japan
The homogeneous hydroformylation of 1-undecene catalyzed by triazenidorhodium complex [Rh (Ph2N3) (CO) (PPh3) 2] in several solvents (toluene, benzene, acetone, and tetrahydrofuran) was studied at 313 K. The products were dodecanal and 2-methylundecanal at 1.0×105 Pa of synthesis gas (CO/H2=1/1) , the amount of dodecanal being larger than that of 2-methylundecanal. A small amount of 2-undecene was also obtained by isomerization of 1-undecene.
In the case of toluene as solvent, the maximum yields of dodecanal and 2-methylundecanal were obtained at 1.0×105 Pa of synthesis gas pressure, while the formation rate of 2-undecene decreased with increasing the synthesis gas pressure from 1.0×104 to 1.0×106 Pa. The maximum yields of dodecanal and 2-methylundecanal were obtained at 323 K, while the formation rate of 2-undecene was accelerated by elevating the reaction temperature in the range from 303 to 333 K at 1.0×105 Pa of synthesis gas pressure. Moreover, the induction period was observed by adding PPh3 into the reaction system at 313 K, 1.0×105 Pa of synthesis gas pressure. Contrastively, a large amounts of PPh3 inhibited the reaction of hydroformylation and isomerization of 1-undecene. A plausible mechanism for hydroformylation was proposed.
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