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Bidentate phosphine ligand and application thereof in hydroformylation reaction

A technology for bidentate phosphine ligands and oxidation reactions, which is applied in the field of bidentate phosphine ligands and their application in hydroformylation reactions, can solve the problem of low linear selectivity of triphenylphosphine ligands, and achieve good results. Effects of catalytic activity and linear selectivity, simple structure, and strong chelating ability

Active Publication Date: 2018-11-13
NANJING CHENGZHI CLEAN ENERGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the linear selectivity of the triphenylphosphine ligand is not high. In order to maintain a high linear product selectivity, it is necessary to use hundreds of times more PPh than the Rh catalyst in the reaction. 3 Ligand

Method used

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  • Bidentate phosphine ligand and application thereof in hydroformylation reaction
  • Bidentate phosphine ligand and application thereof in hydroformylation reaction
  • Bidentate phosphine ligand and application thereof in hydroformylation reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A bidentate phosphine ligand A having the following structure and a preparation method thereof:

[0028]

[0029] Add 1mL (9.6mmol) of salicylaldehyde and 3.4g (9.6mmol) of 3-diphenylphosphino-4-aminobiphenyl, 30ml of absolute ethanol, molecular sieves and glacial acetic acid in the reaction flask, heat and reflux for 24 hours, remove Molecular sieves, concentrated, cooled to room temperature to obtain crude product, recrystallized with ethanol to obtain light yellow crystal 2.8g, namely intermediate product A1 (63.8%); add 30ml absolute ethanol, 1.1mL (6.1mmol) diphenyl Add 2.8gA1 (6.1mmol) after phosphorus chloride is mixed evenly, react at room temperature for 3 hours, concentrate, cool and crystallize to obtain a crude product, recrystallize with ethanol to obtain light yellow crystals, namely bidentate phosphine ligand A3.1g (79.2%) .

[0030] The elemental analysis of the bidentate phosphine ligand A: actual measurement (calculated value): C: 80.47 (80.5); H: ...

Embodiment 2

[0032] A bidentate phosphine ligand B having the following structure and a preparation method thereof:

[0033]

[0034] In the reaction flask, add 0.5mL (4.8mmol) salicylaldehyde and 1.9g (4.8mmol) 3-diphenylphosphino-4-amino-3'nitrobiphenyl, 20ml absolute ethanol, molecular sieves and glacial acetic acid, Heat to reflux for 24 hours, remove molecular sieves, concentrate, cool to room temperature to obtain crude product, recrystallize with ethanol to obtain light yellow crystal 1.4g, i.e. intermediate product B1 (58.1%); add 20ml absolute ethanol in reaction flask, 0.5mL ( 2.8mmol) of diphenylphosphine chloride was mixed evenly, then added 1.4g B1 (2.8mmol), reacted at room temperature for 3 hours, concentrated, cooled and crystallized to obtain a crude product, recrystallized with ethanol to obtain light yellow crystals, namely the bidentate phosphine ligand B1 .4g (72.9%).

[0035] The elemental analysis of the bidentate phosphine ligand B: actual measurement (calculate...

Embodiment 3

[0037] A bidentate phosphine ligand C having the following structure and a preparation method thereof:

[0038]

[0039]Add 2.1g (9.9mmol) 3-phenyl-5-methyl salicylaldehyde and 2.8g (10.1mmol) (o-aminophenyl) diphenylphosphine in the reaction flask, 50ml absolute ethanol, molecular sieves and glacial acetic acid , heated to reflux for 24 hours, removed molecular sieves, concentrated, cooled to room temperature to obtain crude product, recrystallized with ethanol to obtain light yellow crystal 3.3g, namely intermediate product C1 (70.8%); add 30ml absolute ethanol in reaction flask, 0.9mL (5mmol) diphenylphosphine chloride was mixed evenly, then added 2.4gC1 (5.1mmol), reacted at room temperature for 3 hours, concentrated, cooled and crystallized to obtain a crude product, recrystallized with ethanol to obtain light yellow crystals, namely the bidentate phosphine ligand C2 .5 g (76.3%).

[0040] The elemental analysis of the bidentate phosphine ligand C: measured (calculate...

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Abstract

The invention discloses a bidentate phosphine ligand. A structural formula of the bidentate phosphine ligand is shown in a following formula, wherein Ph is phenyl; a, b, c, d, e, f, g and h are the same or different, and are selected from H, R or Ar; R is alkyl or substituted alkyl; Ar is aryl or substituted aryl. A metal-phosphine ligand prepared from the bidentate phosphine ligand and transitionmetals is a catalyst for the hydroformylation reaction, has high activity and linear selectivity, and is a complex from transition metals Co (cobalt) and Rh (rhodium); the usage amount of phosphine ligand in the catalysis reaction is greatly reduced. The bidentate phosphine ligand has the advantages that the synthesizing is easy, and the cost of the raw materials is low. The formula is shown in the attached figure.

Description

technical field [0001] The invention relates to an organic phosphine ligand, in particular to a bidentate phosphine ligand and its application in hydroformylation. Background technique [0002] Hydroformylation reaction, also known as carbonyl synthesis reaction, refers to the reaction of CO and H 2 The process of forming aliphatic aldehydes with one more carbon atom than the original alkenes under the action of catalysts with alkenes. Aldehydes can be easily converted into chemicals such as alcohols, acids, esters, aldol condensation products, and acetals, which are widely used as plasticizers, fabric additives, surfactants, solvents, and fragrances. Hydroformylation has become the largest homogeneous catalytic reaction in industrial production. The global production capacity of OXO products such as butanol and octanol by monopropylene hydroformylation has exceeded 10 million tons per year. [0003] Industrially, the raw material olefins suitable for the oxo synthesis pr...

Claims

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Application Information

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IPC IPC(8): C07F9/50B01J31/24C07C47/02C07C45/50
CPCB01J31/2495B01J2231/321B01J2531/0258B01J2531/822C07C45/505C07F9/5022C07C47/02
Inventor 王健孙红平赵静王江张福强郑义
Owner NANJING CHENGZHI CLEAN ENERGY CO LTD
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