Hydroformylation of 1-Undecene Catalyzed by [Rh(Ph<sub>2</sub>N<sub>3</sub>)(CO)(PPh<sub>3</sub>)<sub>2</sub>]

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  • YONEDA Tetsuya
    Department of Chemistry, College of Science and Technology, Nihon University
  • KAMEDA Noriyuki
    Department of Chemistry, College of Science and Technology, Nihon University

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Other Title
  • [Rh(Ph<sub>2</sub>N<sub>3</sub>)(CO)(PPh<sub>3</sub>)<sub>2</sub>]触媒による1-ウンデセンのヒドロホルミル化反応
  • [Rh(Ph2N3)(CO)(PPh3)2]触媒による1-ウンデセンのヒドロホルミル化反応
  • Rh Ph2N3 CO PPh3 2 ショクバイ ニ ヨル 1 ウンデセン ノ ヒドロホルミルカ ハンノウ
  • Hydroformylation of 1-Undecene Catalyzed by [Rh(Ph2N3)(CO)(PPh3)2].

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Description

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.<br> 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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