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A kind of porous perfluoroalkyl sulfonylimide acidic resin and its application

A perfluoroalkyl sulfonylimide acidic and resin technology, which is applied in the field of coumarin synthesis, can solve the problem that the influence of the H site of the resin cannot be ruled out

Inactive Publication Date: 2016-05-18
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of post-modification method cannot exclude the possible residual -SO in the resin 3 H site effect

Method used

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  • A kind of porous perfluoroalkyl sulfonylimide acidic resin and its application
  • A kind of porous perfluoroalkyl sulfonylimide acidic resin and its application
  • A kind of porous perfluoroalkyl sulfonylimide acidic resin and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the preparation of porous trifluoromethanesulfonimide acidic resin comprises the following steps:

[0044] Synthesis of step 1 p-styrenesulfonyl trifluoromethylsulfonylimide sodium

[0045] The synthesis reaction scheme is as follows:

[0046]

[0047] In a 250mL double-necked round bottom flask, add 16.585g (0.08mol) of p-styrenesulfonyl chloride with a polymerization inhibitor, stir, add 120mL of refined 1,2-dichloroethane, add 13.230g (0.088mol) of three Fluoromethylsulfonamide, heated up to about 40°C to completely dissolve trifluoromethylsulfonamide, and another 19.021g was refined (C 2 h 5 ) 3 Add N (0.188mol) dropwise to a constant pressure funnel, raise the temperature to 60-70°C for 48 hours, cool, add about 40mL0.5mol / LH 2 SO 4 Acidification to remove excess (C 2 h 5 ) 3 N, separation, chloroform extraction, combined organic layers, first with Na 2 CO 3 Wash to alkaline, then wash to neutral with distilled water, concentrate, anhydro...

Embodiment 2

[0054] Example 2: Synthesis of Porous Perfluoroalkylsulfonylimide Acidic Resin Catalyzed 7-Hydroxy-4-methylcoumarin

[0055] The synthetic reaction of 7-hydroxyl-4 methylcoumarin is as follows:

[0056]

[0057] Add 0.55g (5mmol) resorcinol (pale yellow solid), 1.16g (10mmol) methyl acetoacetate (colorless liquid), and 0.62g PDVB-0.3- 4 C F NH (the molar weight of the loaded acid is 10% of the molar weight of resorcinol), the temperature was raised to 140°C for reaction, and the progress of the experiment was monitored by TLC for 2 hours. After the reaction was completed, it was in the form of a bright yellow powder solid, cooled to room temperature, poured into 20 mL of ice water and stirred, a large amount of solid was precipitated, filtered under reduced pressure, and a light yellow solid remained. Soxhlet extracted the solid with acetone at 78°C for 12 hours, and desolvated the extract to obtain a pale yellow solid, which was recrystallized from methanol to obtain a n...

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Abstract

The invention discloses porous perfluoroalkyl sulfimide acid resin which is prepared by the steps of polymerizing p-styrene sulfonyl perfluoroalkyl sulfimide salt and p-divinylbenzene; then performing an acidification reaction. The invention also discloses a catalytic application of the porous perfluoroalkyl sulfimide acid resin in coumarin synthesis and a synthesis method of coumarin. In the invention, the porous perfluoroalkyl sulfimide acid resin can be circularly used as a catalyst for coumarin synthesis; by adopting the synthesis method disclosed by the invention, 80-92% of coumarin yield can be obtained.

Description

technical field [0001] The invention relates to a porous perfluoroalkylsulfonylimide acidic resin and its application, and a method for synthesizing coumarin. Background technique [0002] Strongly acidic cation exchange resins are widely used, common Type acidic resin is mainly -SO 3 Type H and perfluoroalkyl-SO 3 H type, all have strong acidity. Representative products such as divinylbenzene cross-linked sulfonated polystyrene Amberlyst-15 (H 0 ≈-3), perfluoroalkane sulfonic acid resin Nafion (H 0 ≈-12) are all acidic resins with great application potential. However, Amberlyst-15 has low thermal stability (<120°C), and it is difficult to use it for a long time under the condition of heating; Nafion has good thermal stability (<280°C), but it is in a dense and non-porous state, and most of the acid points Buried, unable to fully function in the catalytic system, and expensive. DuPont tried to disperse Nafion resin into porous silica to make Nafion / SiO 2 Compl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08J9/36C08J9/26C08F212/36C08F212/14C07D311/16C07D311/92B01J31/06
Inventor 马忠华贺梦丽马敬中熊蕾陈萌
Owner HUAZHONG AGRI UNIV
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