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Vinyl functionalized phosphine ligand synthesis method, phosphine ligand and application

A vinyl functional, phosphine ligand technology, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, carbon monoxide reaction preparation, etc., can solve the problem of unsatisfactory activity and stability of immobilized catalysts, low P ligand concentration, and catalyst issues such as decreased selectivity

Pending Publication Date: 2021-09-21
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the low concentration of P ligand in the prepared heterogeneous catalyst, the traditional immobilization method has always had unsatisfactory activity and stability of the immobilized catalyst. Compared with the homogeneous hydroformylation catalyst, the heterogeneous catalyst Selectivity has also declined (J.Am. Chem.Soc.2015,137,5204-5209)

Method used

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  • Vinyl functionalized phosphine ligand synthesis method, phosphine ligand and application
  • Vinyl functionalized phosphine ligand synthesis method, phosphine ligand and application
  • Vinyl functionalized phosphine ligand synthesis method, phosphine ligand and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Under the protection of 298K inert gas, 180kg of p-hydroxystyrene (1.5kmol), 182kg of pyridine and 3.6kg of bisphenol A (polymerization inhibitor) were dissolved in 900L of toluene, stirred for 1 hour and poured into the upper tank of the enamel reactor (material storage tank) , located on the upper part of one side of the reactor), add 70kg phosphorus trichloride and 70L toluene to the enamel reactor, adjust the temperature of the reactor to T1 degrees Celsius, and drop the mixed solution of the head tank into the reactor at T1°C, drop After the addition was complete, the reaction was continued for 1 hour.

[0027] Under the protection of 298K inert gas, the pH of the reaction solution was adjusted to 6 with 2% (mass concentration) hydrochloric acid solution, and the reaction was fully annihilated after stirring for 1 hour. After standing for 2 hours, the mixed solution was divided into two layers, and the upper oil layer was taken out. Filter through 10cm thick silica...

Embodiment 2

[0032] Under the protection of 298K inert gas, 180kg of m-hydroxystyrene (1.5kmol), 182kg of pyridine and 3.6kg of bisphenol A (polymerization inhibitor) were dissolved in 900L of toluene (reaction solvent). Add 70kg of phosphorus trichloride and 70L of toluene (reaction solvent) into the enamel reaction kettle, adjust the temperature of the reaction kettle to T1 degrees Celsius, drop the mixed solution of the high level tank into the reaction kettle at T1℃, and continue the reaction after the addition is completed 1 Hour.

[0033] Under the protection of 298K inert gas, the pH of the reaction solution was adjusted to 6 with 2% (mass concentration) hydrochloric acid solution, and the reaction was fully annihilated after stirring for 1 hour. After standing for 2 hours, the mixed solution was divided into two layers, and the upper oil layer was taken out. Filter through diatomaceous earth with a thickness of 10cm, and distill off the solvent at 100°C to obtain a light yellow oil...

Embodiment 3

[0037] Under the protection of 298K inert gas, 180kg of o-hydroxystyrene (1.5kmol), 182kg of pyridine and 3.6kg of bisphenol A were dissolved in 900L of toluene. Phosphorus and 70L toluene, adjust the temperature of the reactor to T1°C, add the mixed solution of the high level tank to the reactor at T1°C, and continue to react for 1 hour after the dropwise addition is completed.

[0038] Under the protection of 298K inert gas, adjust the pH of the reaction solution to 6 with (mass concentration) 2% hydrochloric acid solution, stir for 1 hour to fully annihilate the reaction, and after standing for 2 hours, the mixed solution is divided into two layers, the upper oil layer is taken out, and the oil layer is passed through Filter through 10cm thick diatomaceous earth, distill off the solvent at 100°C to obtain a light yellow oily liquid, add 80kg of ethanol to heat the mixed solvent to 100°C to fully dissolve, then cool down to 5°C to recrystallize and dry to obtain vinyl Functi...

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Abstract

The invention belongs to the field of heterogeneous catalysis, and relates to a method for high-yield macro production of a vinyl functionalized phosphite phosphine ligand. The prepared vinyl functionalized phosphine ligand can be used as a carrier of a heterogeneous catalyst after being polymerized so as to be used for preparing a catalyst for a high-performance olefin hydroformylation reaction. A group with relatively large steric hindrance is introduced to a benzene ring, so that steric hindrance around an Rh active center is increased, and generation of more normal aldehydes is induced. Most importantly, by changing the position of the vinyl on the benzene ring, the steric hindrance around the polymerized P is changed, and the coordination microenvironment is finely regulated and controlled, so that the modulation of hydroformylation catalytic performance is realized. Meanwhile, a vinyl polymerization inhibitor is added in the monomer synthesis process, so that the synthesis yield of the vinyl phosphine ligand monomer is increased, and the emission of pollutants is reduced.

Description

technical field [0001] The invention belongs to the field of heterogeneous catalysis, and in particular relates to a synthesis method and application of a vinyl functionalized phosphine ligand. Background technique [0002] Olefin hydroformylation is a reaction in which olefins, carbon monoxide and hydrogen are converted into aldehydes using transition metal complex catalysts. Today, the concepts of green environmental protection, energy saving and emission reduction are becoming more and more popular. As a reaction of 100% atom economy, this reaction is in line with the basic concept of green chemistry and has been paid more and more attention by chemists. [0003] The product aldehyde of the hydroformylation reaction can be further converted into more value-added chemicals (formula 1) such as alcohols, acids, esters and amines, which are used in the preparation of various detergents, surfactants, Plasticizers or main raw materials of high value-added fine chemicals such a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/46C07F9/48C07F9/145B01J31/06B01J32/00B01J31/22B01J35/10C07C45/50C07C47/02
CPCC07F9/46C07F9/4875C07F9/145B01J31/06B01J31/2213C07C45/505B01J2531/822B01J2531/827B01J2531/845B01J2531/0238B01J2231/321B01J35/617B01J35/615C07C47/02
Inventor 李存耀丁云杰严丽姜淼丁玉龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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