Preparation method and application of natural walnut shell powder sulfonic acid catalyst

A technology of walnut shell and powder sulfonic acid is applied in the field of preparation of natural walnut shell powder sulfonic acid catalyst, can solve the problems of low product yield, high cost, ungreen reaction conditions, etc., and achieves high reaction activity, short reaction time, Effects that are easy to prepare

Pending Publication Date: 2020-04-21
HUAQIAO UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing synthetic methods, the product yield is not high, and the reaction conditions are not green. It is a ubiquitous problem; secondly, some catalysts are poisonous and generally expensive; and in these types of reactions, organic solvents are generally required. Even anhydrous organic solvents increase the cumbersomeness of experimental operations and bring a lot of pressure to environmental protection

Method used

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  • Preparation method and application of natural walnut shell powder sulfonic acid catalyst
  • Preparation method and application of natural walnut shell powder sulfonic acid catalyst
  • Preparation method and application of natural walnut shell powder sulfonic acid catalyst

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preparation example Construction

[0026] like figure 1 Shown, the natural walnut shell powder sulfonic acid catalyst WSP-SO in the following embodiment 3 The preparation method of H comprises:

[0027] (1) Grind 10g of natural walnut shells into powder, add CH 2 Cl 2 30mL and stir well;

[0028] (2) Add 4 mL of chlorosulfonic acid dropwise to the material obtained in step (1) at 0° C., stir at room temperature for 5 h after the addition is complete, then fully wash with ethanol, and finally dry at room temperature to obtain the Natural walnut shell powder sulfonic acid catalyst WSP-SO 3 H.

[0029] The synthetic route of following each embodiment is as follows:

[0030]

[0031] Among them, R 1 is hydrogen, 2-chloro or 4-chloro;

[0032] R 2 is 2-chloro, 4-bromo, 4-nitro or naphthyl;

[0033] R 3 is hydrogen, 2-chloro, 2-nitro, benzyl, 4-methoxy or 4-methyl.

Embodiment 1

[0035] The preparation of benzyl acetate (structural formula is as follows):

[0036]

[0037] Benzyl alcohol (4.6mmol), acetic anhydride (1.2eq), WSP-SO 3 H (50mg), magnetons, then put the test tube into the microwave reactor, set the reaction conditions as follows: microwave radiation power 300W, reaction temperature 50°C, reaction time is 5min, the reaction process is monitored by TLC, after the reaction is completed, the product is collected and passed The product was separated and purified by centrifugation, rotary evaporation and column chromatography with a yield of 95%.

[0038] The infrared and nuclear magnetic characterization of this product are as follows: FT-IR (KBr, cm -1 ): 3034, 2955, 1734, 1497, 1455, 1379, 1024, 964, 920; 1 H NMR (500MHz, CDCl 3 )δ: 7.41-7.34 (m, 5H), 5.15 (s, 2H), 2.13 (s, 1H).

Embodiment 2

[0040] The preparation of 2-chlorobenzyl acetate (structural formula is as follows):

[0041]

[0042] Add 2-chlorobenzyl alcohol (4.6mmol), acetic anhydride (1.2eq), WSP-SO 3 H (50mg), magnetons, then put the test tube into the microwave reactor, set the reaction conditions as follows: microwave radiation power 300W, reaction temperature 50°C, reaction time is 5min, the reaction process is monitored by TLC, after the reaction is completed, the product is collected and passed The product was obtained by separation and purification by centrifugation, rotary evaporation and column chromatography.

[0043] The infrared and nuclear magnetic characterization of this product are as follows: FT-IR (KBr, cm -1 ): 3065, 2959, 1735, 1478, 1443, 1379, 1028, 969, 919; 1 H NMR (500MHz, CDCl 3 )δ: 7.38(d, 1H), 7.30-7.20(m, 4H), 5.21(s, 1H), 2.10(t, 3H).

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Abstract

The invention discloses a preparation method of a natural walnut shell powder sulfonic acid catalyst. The preparation method comprises the following steps: (1) grinding natural walnut shells into a powder, adding CH2Cl2, and uniformly stirring; and (2) dropwise adding a chlorosulfonic acid solution into the material obtained in step (1), stirring at room temperature after the drop-by-drop addition, then fully washing with ethanol, and finally drying at room temperature to obtain the natural walnut shell powder sulfonic acid catalyst. The natural walnut shell powder sulfonic acid catalyst is used for catalyzing an acetylation reaction of alcohol, phenol and amine successfully in microwaves, and ester and amide compounds are synthesized in series. Compared with traditional test tube reactionproduced catalyst, the natural walnut shell powder sulfonic acid catalyst has the advantages of being easy to prepare, low in cost, high in reaction activity, short in reaction time, capable of beingseparated quickly and high in product yield.

Description

technical field [0001] The invention belongs to the technical field of organic catalytic synthesis, in particular to a preparation method and application of natural walnut shell powder sulfonic acid catalyst. Background technique [0002] Esters and amides play a key role in the synthesis of medicines and pesticides. Compounds that are widely used in agriculture, industry, and medicine can be successfully synthesized through ester or amidation reactions. Therefore, it is of great significance to study the green synthesis of esters and amides. In the existing synthetic methods, the product yield is not high, and the reaction conditions are not green. It has always been a common problem; secondly, some catalysts are toxic and generally expensive; and in these types of reactions, organic solvents are generally required. Even anhydrous organic solvents increase the complexity of experimental operations and bring a lot of pressure to environmental protection. Contents of the i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/06C07C67/08C07C69/157C07C201/12C07C205/22C07C231/02C07C233/05C07C233/15C07C233/07C07C233/25
CPCB01J31/06C07C67/08C07C201/12C07C231/02B01J2231/49B01J2231/4283C07C69/157C07C205/22C07C233/05C07C233/15C07C233/07C07C233/25
Inventor 熊兴泉廖旭
Owner HUAQIAO UNIVERSITY
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