Method for biphasic hydroformaylation of olefins based on phosphine-functionalized polyether alkyl guanidine salt ionic liquid

A technology of polyether alkylguanidine and ionic liquid, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalyst, carbon monoxide reaction preparation, etc., can solve the problems of small negative effect and high dosage of ionic liquid, etc. Achieve high catalytic activity, simple separation and circulation

Active Publication Date: 2015-11-04
永春县产品质量检验所福建省香产品质量检验中心国家燃香类产品质量监督检验中心福建
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In the present invention, the phosphine-functionalized ionic liquid not only has the characteristics of a phosphine ligand, can form a complex catalyst with rhodium, but also has the solvent performance of an ionic liquid, and can serve as a ca

Method used

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  • Method for biphasic hydroformaylation of olefins based on phosphine-functionalized polyether alkyl guanidine salt ionic liquid
  • Method for biphasic hydroformaylation of olefins based on phosphine-functionalized polyether alkyl guanidine salt ionic liquid
  • Method for biphasic hydroformaylation of olefins based on phosphine-functionalized polyether alkyl guanidine salt ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Rh(acac)(CO) 2 / [CH 3 (EO) 16 N + H=C(N(CH 3 ) 2 ) 2 ] 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 (EO) 16 N + H=C(N(CH 3 ) 2 ) 2 ] 3 [(SO 3 - ) 3 -1] and 1-octene in the ratio: [CH 3 (EO) 16 N + H=C(N(CH 3 ) 2 ) 2 ] 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 chromatog...

Embodiment 2

[0025] Rh(acac)(CO) 2 / [CH 3 (EO) 16 N + H=C(N(CH 3 ) 2 ) 2 ] 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 (EO) 16 N + H=C(N(CH 3 ) 2 ) 2 ] 3 [(SO 3 - ) 3 -1], 1-octene and n-heptane in the ratio: [CH 3 (EO) 16 N + H=C(N(CH 3 ) 2 ) 2 ] 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 phase, the upper layer is an organic phase, and the organic phase containing the product aldehyde is obtained through simple two-phas...

Embodiment 3

[0028] Rh(acac)(CO) 2 / [Ph(EO) 16 N + H=C(N(CH 3 ) 2 ) 2 ] 3 [(SO 3 - ) 3 Two-phase hydroformylation in -1] / 1-octene system

[0029] The ionic liquid is replaced by [Ph(EO) 16 N + H=C(N(CH 3 ) 2 ) 2 ] 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 12.6%, the selectivity of aldehyde is 91.9%, and the mol ratio of normal aldehyde and isomeric aldehyde is 2.6 :1, TOF value is 2316h -1 .

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Abstract

The present invention relates to a method for biphasic hydroformaylation of olefins based on a phosphine-functionalized polyether alkyl guanidine salt ionic liquid. A biphasic catalytic system is used in the method, wherein the catalytic system consists of the phosphine-functionalized polyether alkyl guanidine salt ionic liquid, a rhodium catalyst, a reaction substrate - olefins and a reaction product - aldehydes; liquid/liquid biphasic hydroformylation of olefins is performed at a certain reaction temperature and syngas pressure; the phosphine-functionalized polyether alkyl guanidine salt 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; separation and recycling of the rhodium catalyst are realized by liquid/liquid biphasic separation after the reaction; the rhodium catalyst is capable of being recycled for multiple times with no obvious decrease in catalytic activity or selectivity; the TOF value of the system reaches 240-2700h-1; and the highest catalytic cycle cumulative TON value reaches 47138.

Description

technical field [0001] The invention relates to the technical field of chemistry and chemical engineering, in particular to a method for two-phase hydroformylation of olefins based on phosphine functionalized polyether alkylguanidine 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 has developed very rapidly, and has become one of the most promising two-phase...

Claims

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Application Information

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IPC IPC(8): C07F9/50C08G65/48C08G65/335C07C279/08C07C277/08B01J31/24B01J31/28C07C45/50C07C47/02
CPCY02P20/50Y02P20/584
Inventor 金欣李淑梅刘强强
Owner 永春县产品质量检验所福建省香产品质量检验中心国家燃香类产品质量监督检验中心福建
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