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A kind of supported copper catalyst for the preparation of substituted amine compound and bisphenol F

A copper catalyst and compound technology, applied in the field of supported copper catalysts, can solve the problems of difficult separation of products, cumbersome post-processing, etc., and achieve the effect of simple post-processing

Active Publication Date: 2021-12-28
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The traditional method of synthesizing substituted amine compounds uses relatively harsh reaction conditions such as strong acid or strong base, and uses highly toxic halogenated hydrocarbons as reaction raw materials for synthesis, and there are defects such as cumbersome post-processing and difficult separation of products. The synthesis of substituted amine compounds by a new type of catalyst under milder conditions has become a research hotspot of scientists in recent years

Method used

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  • A kind of supported copper catalyst for the preparation of substituted amine compound and bisphenol F
  • A kind of supported copper catalyst for the preparation of substituted amine compound and bisphenol F
  • A kind of supported copper catalyst for the preparation of substituted amine compound and bisphenol F

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The copper catalyst of embodiment 1 alumina support

[0053] (1) Put 10mmol of benzotriazole and 5mmol of 2-thiophenethiol in a 100mL round bottom flask, add 7mmol of fluorinating agent Selectfluor, 7mmol of potassium carbonate and 4mmol of copper acetate, and dissolve them completely with 30mL of nitromethane , placed in an oil bath at 100°C for 12 hours, after the reaction was cooled to room temperature, extracted with water and ethyl acetate for 3 to 4 times to collect the organic phase, the organic phase was rotary evaporated to remove the solvent, and the resulting Add 10mmol (3-iodopropyl)trimethoxysilane, 8mmol potassium carbonate, and 20mL dry tetrahydrofuran to the residue, and stir magnetically in an oil bath at 75°C for 12h. After the reaction, filter it, collect the filtrate, and Remove the solvent by rotary evaporation to obtain 2.33g white solid, then add 2.5g copper acetate and 20mL DMF to react at 80°C for 8h, centrifuge after the reaction, and wash the ...

Embodiment 2

[0056] The copper catalyst of embodiment 2 alumina supports

[0057] (1) Put 10mmol of benzotriazole and 10mmol of 2-thiophenethiol in a 100mL round bottom flask, add 10mmol of fluorinating agent Selectfluor, 15mmol of potassium carbonate and 8mmol of copper acetate, and dissolve them completely with 40mL of nitromethane , placed in an oil bath at 130°C for 24 hours, after the reaction was cooled to room temperature, extracted with water and ethyl acetate for 3 to 4 times to collect the organic phase, the organic phase was rotary evaporated to remove the solvent, and the resulting Add 15mmol (3-iodopropyl)trimethoxysilane, 10mmol potassium carbonate, and 30mL dry tetrahydrofuran to the residue, and stir magnetically in an oil bath at 80°C for 12h. After the reaction, filter it, collect the filtrate, and Remove the solvent by rotary evaporation to obtain 2.89g white solid, then add 3.0g copper acetate and 30mL DMF to react at 100°C for 12h, centrifuge after the reaction, and wa...

Embodiment 3

[0059] The copper catalyst of embodiment 3 alumina supports

[0060] (1) Put 10mmol of benzotriazole and 4mmol of 2-thiophenethiol in a 100mL round bottom flask, add 6mmol of fluorinating agent Selectfluor, 6mmol of potassium carbonate and 3mmol of copper acetate, and dissolve them completely with 25mL of nitromethane , placed in an oil bath at 100°C for 12 hours, after the reaction was cooled to room temperature, extracted with water and ethyl acetate for 3 to 4 times to collect the organic phase, the organic phase was rotary evaporated to remove the solvent, and the resulting Add 10mmol (3-iodopropyl)trimethoxysilane, 8mmol potassium carbonate, and 20mL dry tetrahydrofuran to the residue, and stir magnetically in an oil bath at 75°C for 12h. After the reaction, filter it, collect the filtrate, and Remove the solvent by rotary evaporation to obtain 1.86g of white solid, then add 2g of copper acetate and 20mL of DMF to react at 90°C for 10h, centrifuge after the reaction, wash...

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Abstract

The invention discloses a supported copper catalyst prepared by substituting amine compounds and bisphenol F, and belongs to the cross field of organic chemistry and material chemistry. The invention uses aluminum oxide as a carrier to load complexes containing cheap metal copper, and provides a supported copper catalyst. The catalyst of the present invention has excellent catalytic performance, and can be reused more than 5 times to catalyze the synthesis of substituted amine compounds, and the yield does not decrease significantly. At the same time, no strong acid is used as a reaction aid in the process of catalytic synthesis of bisphenol F. It is simple, greatly reduces the reaction cost, conforms to the development concept of green chemistry and environment friendliness, and has a very good application prospect.

Description

technical field [0001] The invention relates to a supported copper catalyst used for preparation of substituted amine compounds and bisphenol F, and belongs to the cross field of organic chemistry and material chemistry. Background technique [0002] At present, homogeneous catalysts are widely used in various fields of organic synthesis, but homogeneous catalysts have disadvantages such as poor stability, difficulty in separating from reaction products, and high price. Therefore, the immobilization of homogeneous catalysts has become an important issue in recent years. research hotspots. The methods of immobilization of homogeneous catalysts include ion exchange method, adsorption method, encapsulation method, covalent bond grafting method, etc. Among them, the covalent bond grafting method uses covalent bonds to bind the complex and the surface of the carrier together , has become the most popular and feasible method for the immobilization of homogeneous catalysts. [00...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22B01J31/18B01J31/16C07C209/68C07C211/45C07C211/52C07C213/08C07C217/58C07C37/20C07C39/16
CPCB01J31/226B01J31/1825B01J31/1633C07C209/68C07C213/08C07C37/20B01J2531/16B01J2531/0241B01J2231/4283B01J2231/4205C07C211/45C07C211/52C07C217/58C07C39/16
Inventor 王大伟李家豪胡文康杨清曹飞
Owner JIANGNAN UNIV
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