Preparation method and application of ionic phosphoramidite ligand

The technology of phosphonamide and monodentate phosphonamide is applied in the field of preparation of ionic phosphonamide ligands, which can solve the problem of limited research on phosphonamide ligands, and achieves efficient preparation, functional modification, good Application prospect, favorable effect of reaction rate

Inactive Publication Date: 2021-03-05
上海簇睿低碳能源技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Compared with the synthetic application of phosphite ligands, the research on phosphoramidite ligands is relatively limited, and the water-soluble phosphoramidite ligands are rarely reported.

Method used

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  • Preparation method and application of ionic phosphoramidite ligand
  • Preparation method and application of ionic phosphoramidite ligand
  • Preparation method and application of ionic phosphoramidite ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The preparation method of the ionic monodentate phosphoramidite with structural formula A and its application in the hydroformylation reaction of butene:

[0038]

[0039] Dissolve 2.04 g of imidazole in 50 mL of ultra-dry dichloromethane under the protection of nitrogen, add 0.43 mL of phosphorus trichloride dropwise under ice bath, react for 30 minutes and filter, and protect the filtrate with nitrogen. Dissolve 0.93 g of biphenol in 10 mL of ultra-dry dichloromethane, add the solution dropwise to the above filtrate, react at room temperature for 1 hour, filter, and spin to dry the solvent. The obtained product is purified by column chromatography, and the eluent is ethyl acetate : n-hexane = 1:10, to obtain monodentate phosphoramidite product. Under the protection of nitrogen, 1.41 g of the obtained monodentate phosphoramidite was dissolved in 20 mL of toluene, 0.52 mL of n-chlorobutane was added, the temperature was raised to 110 ° C and refluxed for 12 h, after ...

Embodiment 2

[0042] The preparation method of the ionic monodentate phosphoramidite whose structural formula is B and its application in the hydroformylation reaction of butene:

[0043]

[0044] Dissolve 2.04 g of imidazole in 50 mL of ultra-dry dichloromethane under the protection of nitrogen, add 0.43 mL of phosphorus trichloride dropwise under ice bath, react for 30 minutes and filter, and protect the filtrate with nitrogen. Dissolve 0.93 g of biphenol in 10 mL of ultra-dry dichloromethane, add the solution dropwise to the above filtrate, react at room temperature for 1 hour, filter, and spin to dry the solvent. The obtained product is purified by column chromatography, and the eluent is ethyl acetate : n-hexane = 1:10, to obtain monodentate phosphoramidite product. Under the protection of nitrogen, 1.41 g of the obtained monodentate phosphoramidite was dissolved in 20 mL of toluene, 0.61 g of 1,3-propane sultone was added, the temperature was raised to 110°C and refluxed for 12 hou...

Embodiment 3

[0047] The preparation method of ionic monodentate phosphoramidite with structural formula C and its application in butene hydroformylation reaction:

[0048]

[0049] Dissolve 2.04 g of imidazole in 50 mL of ultra-dry dichloromethane under the protection of nitrogen, add 0.43 mL of phosphorus trichloride dropwise under ice bath, react for 30 minutes and filter, and protect the filtrate with nitrogen. Dissolve 2.05 g of 3,3'-5,5'-tetra-tert-butyl-2,2'-biphenol in 10 mL of ultra-dry dichloromethane, add the solution dropwise to the above filtrate, react at room temperature for 1 hour, and filter , and the solvent was spin-dried, and the obtained product was purified by column chromatography, and the eluent was ethyl acetate:n-hexane=1:10, to obtain a monodentate phosphonite amide product. Under the protection of nitrogen, 2.53 g of the obtained monodentate phosphoramidite was dissolved in 20 mL of toluene, 0.61 g of 1,3-propane sultone was added, the temperature was raised t...

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Abstract

The invention discloses an ionic phosphoramidite ligand, a preparation method and application of the ionic phosphoramidite ligand in hydroformylation reaction. A general formula of the ligand is shownin the specification. The preparation method comprises the following steps: dissolving phosphorus trichloride and imidazole in a solvent, conducting stirring for reaction, conducting filtering, dissolving substituted biphenol in a solvent, dropwisely adding the formed solution into the filtrate for reaction, and purifying the obtained product to obtain phosphoramidite; and reacting phosphoramidite with a quaternization reagent in a solvent to obtain a product, and purifying the product to obtain the ionic phosphoramidite. Through the method provided by the invention, a series of neutral phosphoramidite ligands can be conveniently synthesized, and a series of ionic phosphoramidite ligands with different physicochemical properties can be efficiently synthesized through a quaternization method.

Description

technical field [0001] The invention relates to a preparation method and application of an ionic phosphonamidite ligand. The catalyst has a simple synthesis process, unique physical and chemical properties, and has high industrial application prospects in reactions such as hydroformylation. It belongs to metal organic and Homogeneous catalysis technology field. Background technique [0002] The hydroformylation reaction, also known as the oxo reaction, is the reaction of olefins and synthesis gas (CO+H 2 ) Catalyzed reaction process to form aldehyde or alcohol. The annual output of aldehydes and alcohols produced by hydroformylation has exceeded 10 million tons. [0003] Co metal complexes were used as catalysts in early hydroformylation reactions, but the reaction conditions were harsh, product selectivity was poor, and Co complexes were highly toxic (Angew. Chem. Int. Ed., 1994, 33, 2144). With the deepening of research, it is found that the catalytic activity of Rh met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6571C07F9/6506B01J31/18B01J31/22B01J31/20C07C45/50C07C47/02
CPCC07F9/6571C07F9/6506B01J31/187B01J31/188B01J31/2213B01J31/20C07C45/505B01J2531/822B01J2531/0241B01J2231/321C07C47/02
Inventor 孙予罕王慧王栋梁马春辉宋文越杜洋袁湘琦
Owner 上海簇睿低碳能源技术有限公司
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