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Phosphine-functionalized polyether quaternary ammonium salt ionic liquid and application thereof in hydroformylation reaction of olefins

A technology of quaternary ammonium salt ions and ionic liquids, applied in the field of two-phase hydroformylation of olefins based on phosphine-functionalized polyether quaternary ammonium salt ionic liquids, can solve the problems of small negative effects and high dosage of ionic liquids, and achieve catalytic activity High, simple separation and circulation effect

Active Publication Date: 2015-11-11
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In the present invention, the polyether quaternary ammonium salt ionic liquid of phosphine functionalization has the characteristic of phosphine ligand, can form complex catalyst with rhodium, has the solvent performance of ionic liquid again, can serve as the carrier of rhodium catalyst, therefore does not need Adding a large amount of other ionic liquids fundamentally solves the problem of excessive use of ionic liquids, and at the same time minimizes the negative effects of ionic liquids in catalytic reactions

Method used

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  • Phosphine-functionalized polyether quaternary ammonium salt ionic liquid and application thereof in hydroformylation reaction of olefins
  • Phosphine-functionalized polyether quaternary ammonium salt ionic liquid and application thereof in hydroformylation reaction of olefins
  • Phosphine-functionalized polyether quaternary ammonium salt ionic liquid and application thereof in hydroformylation reaction of olefins

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Rh(acac)(CO) 2 / [CH 3 (OCH 2 CH 2 ) 16 N(C 2 h 5 ) 3 ] 3 [(SO 3 - ) 3 Two-phase hydroformylation in -1] / 1-octene system

[0023] Under an inert atmosphere, add Rh(acac)(CO) to a stainless steel autoclave 2 、[CH 3 (OCH 2 CH 2 ) 16 N(C 2 h 5 ) 3 ] 3 [(SO3 - ) 3 -1] and 1-octene in the ratio: [CH 3 (OCH 2 CH 2 ) 16 N(C 2 h 5 ) 3 ] 3 [(SO 3 - ) 3 -1] / Rh(acac)(CO) 2 =10:1 (molar ratio), 1-octene / Rh(acac)(CO) 2 =10000:1 (molar ratio), then use synthesis gas (H 2 / CO=1:1) pressurized to 5.0MPa, reaction temperature 95°C, reaction time 0.5 hours, then rapidly cooled to room temperature, vented the synthesis gas and opened the kettle, the system naturally divided into two phases, the lower layer was the ionic liquid containing rhodium catalyst The upper layer is an organic phase, which can also be extracted by adding n-heptane, and the organic phase containing the product aldehyde is obtained through simple two-phase separation. The gas chromat...

Embodiment 2

[0025] Rh(acac)(CO) 2 / [CH 3 (OCH 2 CH 2 ) 16 N(C 2 h 5 ) 3 ] 3 [(SO 3 - ) 3 Two-phase hydroformylation in -1] / 1-octene / n-heptane system

[0026] Under an inert atmosphere, add Rh(acac)(CO) to a stainless steel autoclave 2 、[CH 3 (OCH 2 CH 2 ) 16 N(C 2 h 5 ) 3 ] 3 [(SO 3 - ) 3 -1], 1-octene and n-heptane in the ratio: [CH 3 (OCH 2 CH 2 ) 16 N(C 2 h 5 ) 3 ] 3 [(SO 3 - ) 3 -1] / Rh(acac)(CO) 2 =10:1 (molar ratio), 1-octene / Rh(acac)(CO) 2 =10000:1 (molar ratio), the volume ratio of n-heptane and 1-octene is 2:1, then use synthesis gas (H 2 / CO=1:1) pressurized to 5.0MPa, reaction temperature 95°C, reaction time 0.5 hours, then rapidly cooled to room temperature, vented the synthesis gas and opened the kettle, the system naturally divided into two phases, the lower layer was the ionic liquid containing rhodium catalyst The upper layer is an organic phase, and the organic phase containing the product aldehyde is obtained through simple two-phase se...

Embodiment 3

[0028] Rh(acac)(CO) 2 / [Ph(OCH 2 CH 2 ) 16 N(C 2 h 5 ) 3 ] 3 [(SO 3 - ) 3 Two-phase hydroformylation in -1] / 1-octene system

[0029] The ionic liquid was changed to [Ph(OCH 2 CH 2 ) 16 N(C 2 h 5 ) 3 ] 3 [(SO 3 - ) 3 -1], all the other reaction conditions and steps are the same as in Example 1, and the gas chromatography analysis results are: the conversion rate of 1-octene is 13.2%, the selectivity of aldehyde is 92.5%, and the mol ratio of normal aldehyde and isomeric aldehyde is 2.7 :1, TOF value is 2442h -1 .

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Abstract

The invention relates to a phosphine-functionalized polyether quaternary ammonium salt ionic liquid, and a method of two-phase hydroformylation of olefins on the basis of the phosphine-functionalized polyether quaternary ammonium salt ionic liquid. In the invention, a two-phase catalysis system is employed, wherein the catalysis system is composed of the phosphine-functionalized polyether quaternary ammonium salt ionic liquid, a rhodium catalyst and a reaction substrate olefin and a reaction product aldehyde. A liquid-liquid two-phase hydroformylation reaction is carried out at a certain reaction temperature and under a synthesis gas pressure, wherein the phosphine-functionalized polyether quaternary ammonium salt ionic liquid is not only a phosphine ligand but also a carrier of the rhodium catalyst, so that the system is free of addition of other ionic liquids. When the reaction is finished, the rhodium catalyst is separated and recycled through simple liquid-liquid two-phase separation. The catalytic system is high in catalytic activity. The rhodium catalyst can be used repeatedly for several times without significant reduction of catalytic activity and selectivity.

Description

technical field [0001] The invention relates to the technical field of chemistry and chemical engineering, in particular to a class of phosphine-functionalized polyether quaternary ammonium salt ionic liquid, and a method for two-phase hydroformylation of olefins based on the phosphine-functionalized polyether quaternary ammonium salt ionic liquid. Background technique [0002] The rhodium-catalyzed hydroformylation of olefins is a typical atom-economical reaction, and it is also a carbonylation reaction with more reports in the literature. It has become an ideal method for the preparation of high-carbon aldehydes / alcohols. Homogeneous hydroformylation has the advantages of high catalytic activity, good selectivity and mild reaction conditions, but the separation and recycling of rhodium catalysts has been the focus of attention in the field of homogeneous catalysis for a long time. [0003] In recent years, the liquid / liquid two-phase catalytic system with ionic liquid as t...

Claims

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Application Information

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IPC IPC(8): C07F9/50C07C45/50C07C47/02B01J31/02B01J31/24B01J31/28C08G65/00
CPCY02P20/584Y02P20/50
Inventor 金欣李淑梅
Owner QINGDAO UNIV OF SCI & TECH
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