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Phosphine-functionalized polyether imidazolium-based ionic liquid and application thereof in the hydroformylation of olefins

A technology of polyether imidazolium salt and ionic liquid, applied in the field of chemical industry, can solve the problems of small negative effect and high dosage of ionic liquid, and achieve the effect of high catalytic activity, simple separation and circulation

Active Publication Date: 2015-11-04
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In the present invention, the polyether imidazolium 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 to add additional A large number of other ionic liquids fundamentally solve the problem of excessive dosage of ionic liquids, and at the same time minimize the negative effects of ionic liquids in catalytic reactions

Method used

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  • Phosphine-functionalized polyether imidazolium-based ionic liquid and application thereof in the hydroformylation of olefins
  • Phosphine-functionalized polyether imidazolium-based ionic liquid and application thereof in the hydroformylation of olefins
  • Phosphine-functionalized polyether imidazolium-based ionic liquid and application thereof in the hydroformylation of olefins

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Rh(acac)(CO) 2 / [CH 3 (EO) 16 MICH 3 ] 3 [(SO 3 - )3 Two-phase hydroformylation in -1] / 1-octene system

[0027] Under an inert atmosphere, add Rh(acac)(CO) to a stainless steel autoclave 2 、[CH 3 (EO) 16 MICH 3 ] 3 [(SO 3 - ) 3 -1] and 1-octene in the ratio: [CH 3 (EO) 16 MICH 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 the 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 chromatography analysis results are: the conversion rate of 1-octe...

Embodiment 2

[0029] Rh(acac)(CO) 2 / [CH 3 (EO) 16 MICH 3 ] 3 [(SO 3 - ) 3 Two-phase hydroformylation in -1] / 1-octene / n-heptane system

[0030] Under an inert atmosphere, add Rh(acac)(CO) to a stainless steel autoclave 2 、[CH 3 (EO) 16 MICH 3 ] 3 [(SO 3 - ) 3 -1], 1-octene and n-heptane in the ratio: [CH 3 (EO) 16 MICH 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 separation. The gas chromatography analysis results are: the c...

Embodiment 3

[0032] Rh(acac)(CO) 2 / [Ph(EO) 16 MICH 3 ] 3 [(SO 3 - ) 3 Two-phase hydroformylation in -1] / 1-octene system

[0033] The ionic liquid is replaced by [Ph(EO) 16 MICH 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 transformation rate of 1-octene is 13.9%, the selectivity of aldehyde is 92.5%, and the mol ratio of normal aldehyde and isomeric aldehyde is 2.7 :1, TOF value is 2572h -1 .

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Abstract

The present invention relates to a phosphine-functionalized polyether imidazolium-based ionic liquid and a method for biphasic hydroformaylation of olefins based on the phosphine-functionalized polyether imidazolium-based ionic liquid. The method uses a biphasic catalytic system, wherein the catalytic system consists of a phosphine functionalized polyether imidazolium-based ionic liquid, a rhodium catalyst, the reaction substrate, olefins and the reaction product, aldehydes; liquid / liquid biphasic hydroformylation of olefins is performed at a certain reaction temperature and syngas pressure; the phosphine-functionalized polyether imidazolium-based ionic liquid acts both as a phosphine ligand and as a rhodium catalyst carrier; there is no need to add any other ionic liquid to the system; and separation and recycle of the rhodium catalyst are realized by liquid / liquid biphasic separation after the reaction. The catalytic system provided by the present invention is high in catalytic activity. The rhodium catalyst is capable of being recycled for many times with no obvious decrease in 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 polyetherimidazolium salt ionic liquid and a method for two-phase hydroformylation of olefins based on the phosphine-functionalized polyetherimidazolium 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 the catalyst carrier...

Claims

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Application Information

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IPC IPC(8): C07F9/50C07F9/655C07D233/60B01J31/02B01J31/06B01J31/24C07C45/50C07C47/02C07C47/228C08G65/335C08G65/48C08G65/00
CPCY02P20/584Y02P20/50
Inventor 金欣李淑梅张梅徐冰莹
Owner QINGDAO UNIV OF SCI & TECH
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