A kind of hydroformylation reaction method and catalyst using rhodium ruthenium double metal and tetradentate phosphine ligand

A technology of catalysts and phosphine ligands, which is applied in the direction of physical/chemical process catalysts, catalytic reactions, organic compounds/hydrides/coordination complex catalysts, etc. It can solve the problems of low aldehyde product positive-to-isotropic ratio and achieve high conversion rate , Large industrial application value, high conversion effect

Active Publication Date: 2019-10-11
WUHAN CATALYS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] Aiming at the defect of low positive-to-isotropic ratio of aldehyde products in the existing internal olefin hydroformylation catalytic system, the technical problem to be solved by the present invention is to provide a catalyst and internal olefin combined with rhodium-ruthenium bimetallic and tetradentate phosphine ligands Hydroformylation method

Method used

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  • A kind of hydroformylation reaction method and catalyst using rhodium ruthenium double metal and tetradentate phosphine ligand
  • A kind of hydroformylation reaction method and catalyst using rhodium ruthenium double metal and tetradentate phosphine ligand
  • A kind of hydroformylation reaction method and catalyst using rhodium ruthenium double metal and tetradentate phosphine ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: adopt rhodium ruthenium bimetallic (Rh(acac)(CO) 2 , RuH(Cl)(PNN)(CO)) and biphenyl triphosphine ligand (Tribi) with rhodium ruthenium bimetallic (Rh(acac)(CO) 2 , RuH(Cl)(PNN)(CO)) and biphenyl tetraphosphine ligand (Tetrabi) isomerization and hydroformylation (S / C=2000, S / C is the molar ratio of reactant to catalyst )

[0040] Rh,Ru+Tribi: Weighing the rhodium catalyst Rh(acac)(CO) in the glove box 2 (5.2mg, 0.02mmol), 2,2', 6-three (diphenylphosphinomethyl)-1,1'-biphenyl (Tribi) (60mg, 0.08mmol) into the complexing bottle, and then remove Oxygen / water dichloromethane (Dichloromethane, 2.65g, 31.2mmol) solvent was placed in the bottle, and stirred to dissolve to form a complex solution of rhodium and biphenyltriphosphine ligand. Subsequently, the ruthenium catalyst RuH(Cl)(PNN)(CO) (9.8mg, 0.02mmol) was weighed in the glove box, added to the complexed rhodium catalyst solution, stirred at room temperature to dissolve it. Put the autoclave into the g...

Embodiment 2

[0045] Embodiment 2: adopt rhodium ruthenium bimetallic (Rh(acac)(CO) 2 , RuH(Cl)(PNN)(CO)) and biphenyl triphosphine ligand (Tribi) with rhodium ruthenium bimetallic (Rh(acac)(CO) 2 , RuH(Cl)(PNN)(CO)) and biphenyl tetraphosphine ligand (Tetrabi) isomerization and hydroformylation (S / C=4000)

[0046] Rh,Ru+Tribi: Weighing the rhodium catalyst Rh(acac)(CO) in the glove box 2 (2.6mg, 0.01mmol), 2,2',6-three (diphenylphosphine methyl)-1,1'-biphenyl (Tribi) (30mg, 0.04mmol) into the complexing bottle, and then remove Oxygen / water dichloromethane (Dichloromethane, 2.65g, 31.2mmol) solvent was placed in the bottle, and stirred to dissolve to form a complex solution of rhodium and biphenyltriphosphine ligand. Subsequently, the ruthenium catalyst RuH(Cl)(PNN)(CO) (4.9 mg, 0.01 mmol) was weighed in the glove box, added to the complexed rhodium catalyst solution, and stirred at room temperature to dissolve it. Put the autoclave into the glove box, pipette 100 μl of complexed rhodiu...

Embodiment 3

[0051] Embodiment 3: adopt rhodium ruthenium bimetallic (Rh(acac)(CO) 2 , RuH(Cl)(PNN)(CO)) and biphenyl triphosphine ligand (Tribi) with rhodium ruthenium bimetallic (Rh(acac)(CO) 2 , RuH(Cl)(PNN)(CO)) and biphenyl tetraphosphine ligand (Tetrabi) isomerization and hydroformylation (S / C=10000)

[0052] Rh,Ru+Tribi: Weighing the rhodium catalyst Rh(acac)(CO) in the glove box 2 (2.6mg, 0.01mmol), 2,2',6-three (diphenylphosphine methyl)-1,1'-biphenyl (Tribi) (30mg, 0.04mmol) into the complexing bottle, and then remove Oxygen / water dichloromethane (Dichloromethane, 6.63g, 78.0mmol) solvent was put into the bottle, and stirred to dissolve to form a complex solution of rhodium and biphenyltriphosphine ligand. Subsequently, the ruthenium catalyst RuH(Cl)(PNN)(CO) (4.9 mg, 0.01 mmol) was weighed in the glove box, added to the complexed rhodium catalyst solution, and stirred at room temperature to dissolve it. Put the autoclave into the glove box, pipette 100 μl of complexed rhodiu...

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Abstract

The invention discloses a homogeneous catalytic reaction method and catalyst for isomerization and hydroformylation of long-chain internal olefins. The method adopts two metal complexes of rhodium and ruthenium as catalysts; the ligand adopts a tetradentate phosphine ligand . The catalytic system of the present invention can carry out homogeneous internal olefin isomerization and hydroformylation reactions under certain temperature and pressure. The method of the present invention is not only suitable for long-chain internal olefins (≥C 8 ) and also suitable for internal olefins with carbon number less than 8, it is a method for homogeneous bimetallic catalytic reaction with high positive-to-iso ratio.

Description

technical field [0001] The invention relates to a reaction method and catalyst for isomerization and hydroformylation of internal olefins, in particular to a catalytic system combining a rhodium-ruthenium double metal complex and a biphenyl tetraphosphine ligand, which is used in a homogeneous reaction system Isomerization and hydroformylation of long-chain internal olefins. Background technique [0002] Hydroformylation technology, also known as "oxo synthesis method", has been the largest homogeneous catalytic reaction in the industrial field since it was accidentally discovered by Professor Otten Roelen in 1938 (Chem. Abstr. 1944, 3631). Every year, various aldehydes and alcohols produced by Fe, Zn, Mn, Co, Cu, Ag, Ni, Pt, Pd, Rh, Ru and Ir based catalysts have exceeded 10 million tons. In these catalytic reactions, the ability to achieve high selectivity to linear products (ie, high isotropic ratio) is extremely important for industrial applications. Although BASF, Dow...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/24B01J31/22C07C47/02C07C45/69
CPCC07C45/69B01J31/1815B01J31/2234B01J31/2409B01J2531/822B01J2531/821B01J2531/0258B01J2231/52B01J2231/321C07C47/02C07F9/5027C07F9/58C07F15/0073C07F15/008B01J31/181B01J31/20C07B41/06C07F9/52
Inventor 张绪穆张润通陈才友陈震
Owner WUHAN CATALYS TECH CO LTD
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