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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  • Abstract
  • Description
  • Claims
  • Application Information

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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 carri

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

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Example Embodiment

[0025] Example 1

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

[0027] Under inert atmosphere, add Rh(acac)(CO) to the stainless steel autoclave 2 , [CH 3 (EO) 16 MICH 3 ] 3 [(SO 3 - ) 3 -1] and 1-octene, the ratio is: [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), and then use synthesis gas (H 2 / CO=1:1) Pressurize to 5.0MPa, reaction temperature 95℃, reaction time 0.5 hours, then quickly cool to room temperature, vent the synthesis gas and open the kettle, the system is naturally divided into two phases, the lower layer is the ionic liquid containing rhodium catalyst The upper layer is the organic phase, which can also be extracted with n-heptane. After simple two-phase separation, the organic phase containing the product aldehyde is obtained. The result of gas chromatography analysis is: the conversion rate of 1-octene is ...

Example Embodiment

[0028] Example 2

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

[0030] In an inert atmosphere, add Rh(acac)(CO) into the stainless steel autoclave 2 , [CH 3 (EO) 16 MICH 3 ] 3 [(SO 3 - ) 3 -1], 1-octene and n-heptane, the ratio is: [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 to 1-octene is 2:1, and then syngas (H 2 / CO=1:1) Pressurize to 5.0MPa, reaction temperature 95℃, reaction time 0.5 hours, then quickly cool to room temperature, vent the synthesis gas and open the kettle, the system is naturally divided into two phases, the lower layer is the ionic liquid containing rhodium catalyst The upper layer is the organic phase. After simple two-phase separation, the organic phase containing the product aldehyde is obtained. The gas chromatography analysis result is: the conversion...

Example Embodiment

[0031] Example 3

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

[0033] Ionic liquid is replaced by [Ph(EO) 16 MICH 3 ] 3 [(SO 3 - ) 3 -1], the rest of the reaction conditions and steps are the same as in Example 1. The gas chromatography analysis results are: the conversion rate of 1-octene is 13.9%, the selectivity of aldehyde is 92.5%, and the molar ratio of normal aldehyde to isoformaldehyde 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
CPCY02P20/50Y02P20/584
Inventor 金欣李淑梅张梅徐冰莹
Owner QINGDAO UNIV OF SCI & TECH
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