Binuclear ionic liquid type heteropolyacid salt solid acid catalyst for synthesizing chalcone derivatives, preparation method and application

A technology of solid acid catalyst and ionic liquid, which is applied in the field of preparation of green heterogeneous catalysts and achieves the effects of good recovery and reuse performance, high activity and mild reaction conditions

Active Publication Date: 2020-01-31
HEFEI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no report on the successful synthesis of chalcone derivatives catalyzed by ionic liquid-type heteropolyacid salts

Method used

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  • Binuclear ionic liquid type heteropolyacid salt solid acid catalyst for synthesizing chalcone derivatives, preparation method and application
  • Binuclear ionic liquid type heteropolyacid salt solid acid catalyst for synthesizing chalcone derivatives, preparation method and application
  • Binuclear ionic liquid type heteropolyacid salt solid acid catalyst for synthesizing chalcone derivatives, preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0037] 1) Synthesis of sulfonic acid functionalized binuclear ionic liquid inner salt THDAPS

[0038] Dissolve tetramethylhexamethylenediamine (4.3g, 25mmol) in 20mL of acetonitrile, and slowly add 1,3-propane sultone (6.1g, 50mmol) dropwise under magnetic stirring and ice-bath conditions. After 12 hours of reaction, A blocky white crude product was obtained, which was washed three times with ether and ethyl acetate respectively to obtain the pure inner salt THDAPS.

[0039] 2) Binuclear ionic liquid type heteropoly salt solid acid catalyst [THDAPS] 1.5 Synthesis of PW

[0040]The above inner salt [THDAPS] (1.0g, 2.4mmol) and phosphotungstic acid (4.6g, 1.6mmol) were dissolved in 20mL of deionized water respectively, and then the aqueous solution of phosphotungstic acid was added dropwise to the inner salt solution, at room temperature The reaction was carried out under magnetic stirring for 24 hours. After the reaction was completed, the resulting suspension solution was pl...

Embodiment 2

[0046] 1) Synthesis of sulfonic acid functionalized binuclear ionic liquid inner salt TEDAPS

[0047] Dissolve tetramethylethylenediamine (2.9g, 25mmol) in 40mL of acetonitrile, and slowly add 1,3-propane sultone (9.2g, 75mmol) dropwise under magnetic stirring and ice bath conditions. After 16 hours of reaction, A blocky white crude product was obtained, which was washed three times with ether and ethyl acetate respectively to obtain the pure inner salt TEDAPS.

[0048] 2) Binuclear ionic liquid type heteropoly salt solid acid catalyst [TEDAPS] 1.5 Synthesis of PMo

[0049] The above-mentioned inner salt [TEDAPS] (1.0g, 2.8mmol) and phosphomolybdic acid (5.11g, 2.8mmol) were dissolved in 30mL deionized water, and then the aqueous solution of phosphomolybdic acid was added dropwise to the inner salt solution, at room temperature The reaction was carried out under magnetic stirring for 18 hours. After the reaction was completed, the obtained suspension solution was placed in a...

Embodiment 3

[0052] 1) Synthesis of sulfonic acid functionalized binuclear ionic liquid inner salt TBDAPS

[0053] Dissolve tetramethylbutanediamine (3.6g, 25mmol) in 50mL of acetonitrile, under magnetic stirring and ice bath conditions, slowly add 1,3-propane sultone (7.6g, 62.5mmol) dropwise, and after 20h of reaction , to obtain a blocky white crude product, which was washed three times with ether and ethyl acetate to obtain the pure product inner salt TBDAPS.

[0054] 2) Binuclear ionic liquid type heteropoly acid salt solid acid catalyst [TBDAPS] 2 Synthesis of SiW

[0055] The above inner salt TBDAPS (1.0g, 2.6mmol) and silicotungstic acid (5.18g, 1.8mmol) were dissolved in 15mL of deionized water respectively, then the aqueous solution of silicotungstic acid was added dropwise to the inner salt solution, and magnetically Stir the reaction for 18 hours. After the reaction is completed, place the resulting suspension in an oven at 70°C. After evaporating water to dryness, the white ...

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Abstract

The invention discloses a binuclear ionic liquid type heteropolyacid salt solid acid catalyst for synthesizing chalcone derivatives as well as a preparation method and application thereof, and relatesto the technical field of preparation of green heterogeneous catalysts in organic chemical industry. The preparation method comprises the following steps: reacting a tetramethyl diamine compound with1, 3-propane sultone to obtain a sulfonic acid functionalized binuclear ionic liquid inner salt, and carrying out hybridization reaction on the sulfonic acid functionalized binuclear ionic liquid inner salt and heteropolyacid by using water as a solvent. According to the invention, three binuclear sulfonic acid functionalized ionic liquid inner salts with different carbon chain lengths are respectively used for hybridizing with the heteropolyacid; the binuclear sulfonic acid functionalized ionic liquid type heteropolyacid salt solid acid catalyst is simply prepared; the catalyst has the advantages of high catalytic activity, high chalcone derivative yield (up to 81-94%), low consumption, mild reaction conditions, short reaction time and favorable catalyst recovery and reuse properties, can implement stable reuse through simple filtration operation, and effectively solves the problems of difficulty in recovery and separation of the ionic liquid catalyst, incapability of recovering andreusing the heteropolyacid catalyst and the like.

Description

technical field [0001] The invention relates to the technical field of preparation of green multi-phase catalysts in organic chemical industry, in particular to a dinuclear ionic liquid type heteropoly salt solid acid catalyst for synthesizing chalcone derivatives, a preparation method and application. Background technique [0002] Chalcone derivatives are widely distributed in nature, such as safflower, hops, licorice and other medicinal plants, and are an important class of organic synthesis intermediates. In addition, chalcone derivatives also have important pharmacological effects, which not only play an important role in plant resistance to diseases and parasites, but also have strong biological activities in antiviral, antitumor, and antimalarial aspects. Using benzaldehyde compounds and acetophenone as reactants, using a homogeneous strong base or strong acid as a catalyst, the Claisen-Schmidt condensation reaction occurs, and the condensation reaction is one of the i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/18B01J27/188B01J31/34C07C303/32C07C309/13C07C45/74C07C49/796C07C49/807C07C201/12C07C205/45C07C253/30C07C255/56
CPCB01J31/0285B01J31/0298B01J27/188B01J31/34C07C303/32C07C45/74C07C201/12C07C253/30C07C309/13C07C49/796C07C49/807C07C205/45C07C255/56Y02P20/584
Inventor 王晓晨刘安求董强徐杨书函高大明朱德春吴云徐泽忠叶超杰方志
Owner HEFEI UNIV
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