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Phosphorus salt amphiphilic bifunctional organic catalyst as well as preparation method and application thereof

An organic catalyst and amphiphilic technology, which is applied in the field of phosphorus salt amphiphilic bifunctional organic catalyst and its preparation, can solve the problems of multi-component weighing and measurement, increased errors, accuracy and mechanism research, etc. problems, to achieve the effect of precise components, short synthetic routes, and easy access to raw materials

Pending Publication Date: 2022-04-12
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the characteristic of the existing organic catalytic system is that the two or more components of the nucleophilic and electrophilic reagents are mixed or even added with a cocatalyst or initiator to realize the polymerization reaction, which brings great benefits to the reagent operation, accuracy and mechanism research of the polymerization reaction. It is difficult; the weighing and measuring of multiple components increases the error of experimental operation

Method used

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  • Phosphorus salt amphiphilic bifunctional organic catalyst as well as preparation method and application thereof
  • Phosphorus salt amphiphilic bifunctional organic catalyst as well as preparation method and application thereof
  • Phosphorus salt amphiphilic bifunctional organic catalyst as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] The synthetic route of catalyst CAT1 is as follows:

[0083]

[0084] in, The molecular structure formula is as follows:

[0085]

[0086] The preparation process is as follows:

[0087] In a flame-dried Schlenk vessel, diallyldiphenylphosphine bromide (173.6 mg, 0.5 mmol, 1 equiv) and 9-borabicyclo[3.3.1]nonane (9-BBN) (122 mg, 1.0 mmol, 2.0 equiv) was dissolved in 10 mL of chloroform. The reaction mixture was allowed to stir at 80 °C for 12 hours. All volatiles were removed and the resulting white solid was washed 3 times (10 mL) with hexanes to give the desired product in quantitative yield, product 1 H NMR spectrum as figure 1 Shown (400MHz, CDCl 3 , 298K).

Embodiment 2

[0089] The synthesis of catalyst CAT2, synthetic route is as follows:

[0090]

[0091] in, The molecular structure formula is as follows:

[0092]

[0093] The preparation process is as follows:

[0094] In a flame-dried Schlenk vessel, diallyldiphenylphosphine iodide (307mg, 0.78mmol, 1 equiv) and 9-borabicyclo[3.3.1]nonane (9-BBN) (190.4mg, 1.56 mmol, 2 equivalents) dissolved in 10mL CHCl 3 middle. The reaction mixture was allowed to stir at 80 °C for 12 hours. All volatiles were removed and the resulting white solid was washed 3 times (10 mL) with hexane to afford the desired product in quantitative yield, product 1 H NMR spectrum as figure 2 Shown (400MHz, CDCl 3 , 298K).

Embodiment 3

[0096] The synthetic route of catalyst CAT4 is as follows:

[0097]

[0098] The preparation process is as follows:

[0099] In a flame-dried Schlenk vessel, dissolve CAT1 (118.3 mg, 0.2 mmol, 1 equiv) and sodium benzoate (115.3 mg, 0.8 mmol, 4 equiv) in 8 ml of CHCl 3 middle. The reaction mixture was allowed to stir at room temperature for 48 hours. The filtrate was collected by filtration under nitrogen to remove all volatiles and the resulting white oil was washed 3 times (10 mL) with hexane to obtain the desired white quantitative product.

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Abstract

The invention discloses a phosphorus salt amphiphilic bifunctional organic catalyst as well as a preparation method and application thereof, and belongs to the field of synthesis and application of organic catalysts. The invention solves the problem that the existing organic catalytic system is characterized in that the polymerization reaction can be realized only by mixing two or more components of nucleophilic and electrophilic reagents and even adding a cocatalyst or an initiator. According to the phosphorus salt amphiphilic bifunctional organic catalyst provided by the invention, nucleophilic and electrophilic groups and initiation species are mixed into a catalytic system, the catalyst has nucleophilic and electrophilic bifunctional sites, and the use of a complex multi-component multicomponent catalytic system is avoided. The catalyst can be used for preparing high polymer materials such as polyether, polyester, polycarbonate, polythiocarbonate and polythioether and synthesizing blocks or random copolymers of the high polymer materials, can also be used for preparing fine chemicals such as cyclic carbonate, lactone and thiocyclic carbonate through small organic molecule coupling reaction, and has the characteristics of high efficiency, high selectivity, controllability and the like.

Description

technical field [0001] The invention relates to a phosphorus salt amphiphilic bifunctional organic catalyst and a preparation method and application thereof, belonging to the field of organic catalyst synthesis and application. Background technique [0002] Organocatalysts have attracted the attention of scientific researchers because of their low cost, easy availability, and low biological toxicity. However, compared with the application of organocatalysts in organic methodology, organocatalysts are still in their infancy in the field of polymer synthesis and preparation. Typical polymer materials include: polyester, polycarbonate, polyether, polyamide, polysiloxane, polyurethane, etc. [0003] At present, the commonly used organic catalytic systems mainly include the following categories: carboxylic acid catalytic system, pyridine base catalytic system, nitrogen-heterocyclic carbene catalytic system, nitrogen-containing organic base (guanidine, amidino, amine) catalytic sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02C07D317/36C07F9/6596C08G65/10C08G64/34C08G63/42C08G63/87
Inventor 李志波王晓武
Owner QINGDAO UNIV OF SCI & TECH
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