Method for recovering and reusing selective homogeneous hydrogenation catalyst
The present invention relates to a method for recovering and reusing a selective homogeneous hydrogenation catalyst. The present invention relates to a method for recovering a selective homogeneous hydrogenation catalyst from a second reaction resolution in which a synthesis of cyclododecene is completed after synthesizing the cyclododecene by selective hydrogenation of a first reaction solution containing cyclododecatriene, triphenylphosphine, formaldehyde, and ruthenium chloride, and the method includes: preparing the selective homogeneous hydrogenation catalyst from the triphenylphosphine, the formaldehyde, and the ruthenium chloride during the selective hydrogenation of the first reaction solution, and synthesizing the cyclododecene; mixing a solvent containing cyclododecanone with the first reaction solution; and recovering the selective homogeneous hydrogenation catalyst through evaporation separation from the second reaction solution in which the synthesis of the cyclododecene is completed.
1 . A method for recovering a selective homogeneous hydrogenation catalyst comprising:
preparing a selective homogeneous hydrogenation catalyst from triphenylphosphine, formaldehyde, and ruthenium chloride in a first reaction solution, and selectively hydrogenating cyclododecatriene to cyclododecene in the first reaction solution;
in a second reaction mixture, mixing a solvent containing cyclododecanone with the first reaction solution; and
recovering the selective homogeneous hydrogenation catalyst through evaporation separation from the second reaction solution.
2 . The method of claim 1 , wherein the evaporation separation is performed through a distillation column,
the distillation column is provided with an upper column through which a product containing the cyclododecene is discharged, and a lower column through which the selective homogeneous hydrogenation catalyst and the solvent are separated, and
a pressure of the upper column is 0.1 bar or less and a temperature thereof is 100° C. to 200° C., and a pressure of the lower column is 0.1 bar or less and the temperature thereof is 150° C. to 250° C., during the evaporation separation.
3 . The method of claim 1 , wherein a molar ratio of the ruthenium chloride:the triphenylphosphine:the formaldehyde is 1:100 to 300:150 to 500.
4 . The method of claim 1 , wherein the selective hydrogenation is performed in a stirred tank reactor equipped with a gas-induced hollow stirrer.
5 . The method of claim 4 , wherein hydrogen gas present in a gas phase at an upper end of the stirred tank reactor is supplied to the reaction solution through a hollow of the gas-induced hollow stirrer.
6 . The method of claim 1 , wherein the first reaction solution further includes a catalyst activator containing acetic acid.
7 . The method of claim 6 , wherein the catalyst activator is added in an amount of 0.01 to 2 parts by weight based on 100 parts by weight of the cyclododecatriene.
8 . The method of claim 1 , wherein the selective hydrogenation is performed under conditions of a temperature of 100 to 200° C. and a pressure of 10 to 80 bar.
9 . A method for reusing a recovered selective homogeneous hydrogenation catalyst, comprising:
re-introducing the selective homogeneous hydrogenation catalyst recovered by the method of claim 1 into a third reaction solution containing the cyclododecatriene and performing secondary selective hydrogenation of the selective homogeneous hydrogenation catalyst to synthesize the cyclododecene.