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A kind of method for preparing aldehyde based on phosphonamide phosphine ligand catalyzing internal olefin

A technology for phosphine amide and phosphine ligands is applied in the field of catalyzing internal olefins to prepare aldehydes based on phosphine amide phosphine ligands, which can solve the problems of poor aldehyde selectivity, ligand deactivation, low conversion rate and the like, and reduce production energy consumption. , increase safety, effect on water stabilization

Active Publication Date: 2022-07-22
SICHUAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, rhodium-catalyzed cyclic olefin hydroformylation reaction conditions are relatively harsh, such as high pressure (8-22MPa), long reaction time (more than 50 hours), and adding some auxiliary catalytic additives and using mixed phosphine ligands , and the conversion rate is low, and the selectivity to aldehydes is poor
[0005] Some studies have pointed out that a catalyst for the hydroformylation reaction of internal olefins and its preparation method and application, the catalyst of the invention is an oil-soluble catalyst, and the catalytic system is a homogeneous catalytic system, but the invention has relatively high reaction temperature and high pressure , and the ligand is easily inactivated at high temperature

Method used

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  • A kind of method for preparing aldehyde based on phosphonamide phosphine ligand catalyzing internal olefin
  • A kind of method for preparing aldehyde based on phosphonamide phosphine ligand catalyzing internal olefin
  • A kind of method for preparing aldehyde based on phosphonamide phosphine ligand catalyzing internal olefin

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Embodiment 1

[0033] The invention provides a kind of method based on phosphine phosphine phosphine ligand and rhodium catalyst catalysis internal olefin to prepare straight chain valeraldehyde, comprises the following steps:

[0034] Combining the phosphine ligand binaphthol bisindolylphosphine with the metal rhodium precursor Rh(acac)(CO) 2 The molar ratio was 2:1 and was added to the autoclave. After adding toluene solvent, the gas was replaced with the synthesis gas mixed with hydrogen and carbon monoxide at a partial pressure ratio of 1:1. Then 5g of 2-butene was mixed with Rh (acac)(CO) 2 According to the 1064 molar ratio, a sample was taken and added to the reaction kettle. Then under the conditions of 1.0MPa (constant pressure) and 80°C, the reaction was stirred for 2h. After the reaction is completed, the product mixture is analyzed by gas chromatography, and the ratio of normal and iso-valeraldehyde is as follows:

[0035]

[0036] a molar ratio of n-aldehyde to iso-aldehyde...

Embodiment 2

[0039] The invention provides a method for catalyzing internal olefin linear valeraldehyde based on phosphine phosphine ligand, comprising the following steps:

[0040] Combining the phosphine ligand binaphthol bisindolylphosphine with the metal rhodium precursor Rh(acac)(CO) 2 The molar ratio was 5:1 and added to the autoclave, and then the xylene solvent was added, and the synthesis gas mixed with hydrogen and carbon monoxide at a partial pressure ratio of 2:1 was used to replace the gas, and then 5g of 2-butene was mixed with Rh (acac)(CO) 2A sample was taken at a 975 molar ratio and added to the reactor. Then, under the conditions of 1.0MPa (constant pressure) and 70°C, the reaction was stirred for 6h. After the reaction is completed, the product mixture is analyzed by gas chromatography, and the ratio of normal and iso-valeraldehyde is as follows:

[0041]

[0042] a is the molar ratio of n-aldehyde to iso-aldehyde;

[0043] b is the overall yield of valeraldehyde....

Embodiment 3

[0045] The present invention provides a method for preparing linear valeraldehyde based on phosphonamide phosphine ligand catalyzed internal olefin, comprising the following steps:

[0046] The phosphine ligand binaphthol bis-indolyl phosphine and the metal rhodium precursor Rh(COD)(acac) were added to the autoclave at a molar ratio of 10:1, and after adding trimethylbenzene solvent, hydrogen and carbon monoxide were used to press The synthesis gas mixed with a partial pressure ratio of 0.8:1 was subjected to the replacement gas operation, and then 5 g of 2-butene and Rh(COD)(acac) were sampled at a molar ratio of 2000 and added to the reaction kettle. Then under the conditions of 1.5MPa (constant pressure) and 80°C, the reaction was stirred for 6h. After the reaction is completed, the product mixture is analyzed by gas chromatography, and the ratio of normal and iso-valeraldehyde is as follows:

[0047]

[0048]

[0049] a is the molar ratio of n-aldehyde to iso-aldehy...

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Abstract

The invention discloses a method for preparing aldehyde based on phosphine amide phosphine ligand catalyzed by internal olefin. The internal olefin, organic solvent, rhodium complex and phosphine ligand are homogeneously reacted in synthesis gas, so that high efficiency and high selectivity can be achieved. Internal olefins are converted to aldehydes by homogeneous hydroformylation. For example, it can generate linear aldehydes with high selectivity for common internal olefins, and selectively generate dialdehydes for cyclic dienes, and the conditions of the whole reaction system are mild, the hydrogenation products are less, and the catalyst can be recycled, the production cost is reduced, and the production Security increases.

Description

technical field [0001] The present invention relates to the technical field of organic compound synthesis, in particular to a method for preparing aldehyde based on phosphonamide phosphine ligand-catalyzed internal olefin. Background technique [0002] Hydroformylation reaction refers to the conversion of alkenes or alkynes with synthesis gas (CO+H) under the catalysis of transition metals. 2 ) reaction, the product is an aldehyde with one more carbon, which is an atom-economical reaction, the atom utilization rate is 100%, and the world's aldehyde output exceeds 10 million tons / year, which is one of the most important application technologies in the chemical industry today. [0003] The hydroformylation of olefins has problems of chemoselectivity and regioselectivity. The chemoselectivity lies in the hydrogenation or carbonylation of the substrate, and the regioselectivity involves the selectivity of linear and branched aldehydes. For the hydroformylation of internal olefi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/50C07C47/02B01J31/22
CPCC07C45/50B01J31/186B01J2231/321B01J2531/822C07C47/02Y02P20/584
Inventor 郑学丽陈华唐松柏袁茂林李瑞祥付海燕
Owner SICHUAN UNIV
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