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Diphosphine ligand and application thereof in hydroformylation

A bidentate phosphine ligand, chemical reaction technology, applied in the direction of carbon monoxide reaction preparation, organic compound preparation, organic compound/hydride/coordination complex catalyst, etc., can solve the problem of linear selectivity of triphenylphosphine ligand Advanced problems, to achieve the effect of good catalytic activity and linear selectivity, simple structure, strong chelating ability

Active Publication Date: 2018-09-28
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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  • Diphosphine ligand and application thereof in hydroformylation
  • Diphosphine ligand and application thereof in hydroformylation
  • Diphosphine ligand and application thereof in hydroformylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A bidentate phosphine ligand A having the following structure and a preparation method thereof:

[0026]

[0027] Add 2.1mL (20.1mmol) salicylaldehyde and 5.6g (20.2mmol) (o-aminophenyl) diphenylphosphine in reaction flask, 50ml dehydrated alcohol, molecular sieve and glacial acetic acid, heat and reflux for 24 hours, remove molecular sieve, Concentrate, cool to room temperature to obtain crude product, recrystallize with ethanol / ether to obtain light yellow crystal 5.8g, namely intermediate product A1 (75.7%); add 30ml absolute ethanol, 2.7mL (15mmol) diphenyl chloride Add 5.7gA1 (15mmol) 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, that is, bidentate phosphine ligand A7.1g (83.8%).

[0028] The elemental analysis of the bidentate phosphine ligand A: actual measurement (calculated value): C: 78.46 (78.58); H: 5...

Embodiment 2

[0030] A bidentate phosphine ligand B having the following structure and a preparation method thereof:

[0031]

[0032] In the reaction flask, add 1.1mL (10.5mmol) salicylaldehyde and 3.2g (10.5mmol) 2-phenylphosphino-4-ethylaniline, 30ml absolute ethanol, molecular sieves and glacial acetic acid, heat and reflux for 24 hours, remove Molecular sieves, concentrated, cooled to room temperature to obtain a crude product, recrystallized with ethanol / ether to obtain 2.9g of light yellow crystals, namely intermediate product B1 (67.5%); add 30ml of absolute ethanol, 0.9mL (5mmol) diphenyl Add 2.1g B1 (5.1mmol) after the phosphorous chloride is mixed uniformly, react at room temperature for 3 hours, concentrate, cool and crystallize to obtain crude product, recrystallize with ethanol to obtain light yellow crystal, namely bidentate phosphine ligand B2.3g (77.6% ).

[0033] Elemental analysis of the bidentate phosphine ligand: actual measurement (calculated value): C: 79.08 (78.9...

Embodiment 3

[0035] A bidentate phosphine ligand C having the following structure and a preparation method thereof:

[0036]

[0037]Add 1.5mL (9.9mmol) o-tert-butyl salicylaldehyde and 2.8g (10.1mmol) (o-aminophenyl) diphenylphosphine, 30ml absolute ethanol, molecular sieves and glacial acetic acid in the reaction flask, and heat to reflux for 24 hours , remove molecular sieves, concentrate, cool to room temperature to obtain crude product, recrystallize with ethanol / ether to obtain light yellow crystal 3.1g, namely intermediate product C1 (71.7%); add 30ml absolute ethanol in reaction flask, 0.9mL (5mmol) Add 2.2g C1 (5mmol) after diphenylphosphine 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, that is, bidentate phosphine ligand C2.5g (80.5 %).

[0038] Elemental analysis of the bidentate phosphine ligand: actual measurement (calculated value): C...

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Abstract

The invention discloses a diphosphine ligand, the structural general formula of which is as follows: in the general formula, Ph is phenyl, a, b, c, d, e, f, g and h are the same or different, and areselected from H, R, OR, NR2 and NO2 or cyan; R is alkyl or substituted alkyl. A metal-phosphine ligand complex prepared from the diphosphine ligand and a transitional metal complex can be applied to acatalyst for hydroformylation and is high in activity and linear selectivity, and is particularly a complex based on a transitional metal selected from Co and Rh. Furthermore, the use amount of a phosphine ligand in catalytic reaction is greatly reduced. The diphosphine ligand disclosed by the invention is easy to synthesize, and the raw materials are low in cost.

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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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/50B01J31/24C07C47/02C07C45/50
CPCB01J31/2495B01J2531/0258B01J2531/822C07C45/505C07F9/5022C07C47/02
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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