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Complex catalyst containing diphosphine ligand

A technology of bisphosphine ligands and catalysts, which is applied in the field of complex catalysts, can solve the problems of large amount of ligands, low positive/isotropic ratio of product butyraldehyde, easy ligand decomposition, etc., and achieve good thermal stability

Inactive Publication Date: 2016-04-20
SHANGHAI HUAYI GRP CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Rh / TPP is currently a widely used catalyst system for the synthesis of butyraldehyde from propylene hydroformylation. Not high (<20), prone to ligand decomposition and metal rhodium precipitation during the catalyst cycle, resulting in catalyst deactivation
[0006] The previous research of the research group [Liao Benren et al., Molecular Catalysis, 2015, 29(1), 19-26] found that the addition of bidentate phosphite ligands and bisphosphine ligands can significantly improve the aldehyde content of 1-butene hydroformylation products. Although speculated that the molecular structure of the catalyst when adding specific bidentate phosphite and DPPB explained the reasons for improving the selectivity of the catalyst, it did not mention other bidentate phosphite ligands and The molecular structure of the catalyst when the bisphosphine ligand is used as an additive does not mention the stability of the metal complex itself

Method used

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  • Complex catalyst containing diphosphine ligand
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  • Complex catalyst containing diphosphine ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add [Rh(acac)(CO) to a 200mL stainless steel autoclave equipped with a pressure gauge under air atmosphere 2 ] (0.07mmol, 18.1mg) and 0.14mmol of 1,3-bis(diphenylphosphine)propane L3 bidentate phosphine ligand and 0.14mmol of L12 bidentate phosphite ligand, and 70mL of anhydrous toluene, connected Gas pipeline, after replacing the gas in the kettle with synthesis gas (hydrogen: carbon monoxide = 1:1) three times, stir with an electromagnetically driven mechanical stirrer, heat up to the temperature inside the kettle at 100°C, and feed synthesis gas until the total pressure is 2.0MPa , reacted at 100°C and 2.0MPa for 1h to prepare rhodium / (bidentate phosphite-bisphosphine ligand) complex catalyst HRh(L12)(L3)(CO). Its molecular structure is as follows: 31 PNMR (Toluene, 162MHz) P1 of L12 coordinated with rhodium: δ180.7ppm, P2 of L12 coordinated with rhodium: δ176.0ppm, P3 of L3 coordinated with rhodium: 24.0ppm, P4 of L3 in the complex: -19.6ppm, 1 J RhP1 = 248Hz,...

Embodiment 2

[0032] Add [Rh(acac)(CO) to a 200mL stainless steel autoclave equipped with a pressure gauge under air atmosphere 2 ] (0.07mmol, 18.1mg) and 0.14mmol of the BISBI ligand L1 bidentate phosphine ligand and 0.14mmol of the L12 bidentate phosphite ligand, and 70mL of anhydrous toluene, connect the gas line to the synthesis gas (hydrogen: Carbon monoxide = 1:1) After replacing the gas in the kettle three times, stir with an electromagnetically driven mechanical stirrer, heat up to the inner temperature of the kettle at 100°C, and feed synthesis gas until the total pressure is 2.0MPa, at 100°C, 2.0MPa After reacting for 1 h, the rhodium / (bidentate phosphite-bisphosphine ligand) complex catalyst HRh(L12)(L1)(CO) was obtained. Its molecular structure is as follows: 31 PNMR (Toluene, 162MHz) P1 of L12 coordinated with rhodium: δ179.8ppm, P2 of L12 coordinated with rhodium: δ175.9ppm, P3 of L1 coordinated with rhodium: 30.1ppm, P4 of L1 in the complex: -11.2ppm, 1 J RhP1 = 249Hz, 1...

Embodiment 3

[0035] Add [Rh(acac)(CO) to a 200mL stainless steel autoclave equipped with a pressure gauge under air atmosphere 2 ] (0.07mmol, 18.1mg) and 0.14mmol of 1,4-bis(diphenylphosphine)butane L4 bidentate phosphine ligand and 0.14mmol of L10 bidentate phosphite ligand, and 70mL of anhydrous toluene, Connect the gas pipeline, replace the gas in the kettle with synthesis gas (hydrogen: carbon monoxide = 1:1) three times, stir with an electromagnetically driven mechanical stirrer, heat up to 100°C inside the kettle, and feed synthesis gas until the total pressure is 2.0 MPa, under the conditions of 100° C. and 2.0 MPa, react for 1 h to prepare rhodium / (bidentate phosphite-bisphosphine ligand) complex catalyst HRh(L10)(L4)(CO). Its molecular structure is as follows: 31 PNMR (Toluene, 162MHz) P1 of L10 coordinated with rhodium: δ179.8ppm, P2 of L10 coordinated with rhodium: δ176.2ppm, P3 of L4 coordinated with rhodium: 24.4ppm, P4 of L4 in the complex: -15.6ppm, 1 J RhP1 = 249Hz, ...

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Abstract

The invention relates to a complex catalyst containing a diphosphine ligand. The complex catalyst is prepared from rhodium, bidentate phosphate ester and the diphosphine ligand. The general structure formula is shown in the specification. The complex catalyst can be used for reactions such as hydroformylation.

Description

technical field [0001] The invention relates to a complex catalyst containing a bisphosphine ligand. Background technique [0002] Olefin hydroformylation can conveniently and effectively convert cheap and easy-to-obtain basic chemical raw materials such as olefins into a variety of important chemical products such as aldehydes. It is the largest homogeneous catalytic process so far. [Trzeciak, A.M.; J. J. Coord. Chem. Rev. 1999, 190-192, 883-900]. Since the 1970s, rhodium catalysts modified with phosphorus-containing ligands have dominated the research on the hydroformylation of olefins due to their outstanding advantages such as high activity, excellent selectivity, and mild reaction conditions, and have become an industrial hydroformylation catalyst. Catalysts for the acylation process, international common hydroformylation process suppliers such as BASF, EvonikOXENO, Perstorp, DOW, etc. all use rhodium catalysts modified with phosphorus-containing ligands. Among them...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/24C07C45/50C07C47/02
CPCB01J31/2495B01J31/185B01J31/2404B01J31/2442B01J31/2461B01J2231/321B01J2531/0238B01J2531/822C07C45/50
Inventor 杨旭石赖春波范曼曼廖本仁高山林李媛陈毅立陈建伟张春雷
Owner SHANGHAI HUAYI GRP CO
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