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Method for synthesizing ketone through catalyzing and hydrolyzing alkyne with silver perfluorooctanesulfonate

A technology for catalyzing alkynes with silver perfluorosulfonate and silver salts, which is applied in the field of catalysis to achieve good selectivity, good yield, and simple separation of products

Active Publication Date: 2015-04-22
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no public documents and patent applications about the method of preparing ketones by the hydrolysis of terminal alkynes catalyzed by silver perfluorooctane sulfonate at home and abroad.

Method used

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  • Method for synthesizing ketone through catalyzing and hydrolyzing alkyne with silver perfluorooctanesulfonate
  • Method for synthesizing ketone through catalyzing and hydrolyzing alkyne with silver perfluorooctanesulfonate
  • Method for synthesizing ketone through catalyzing and hydrolyzing alkyne with silver perfluorooctanesulfonate

Examples

Experimental program
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Effect test

preparation example 1

[0019] Add 0.05 mmol perfluorooctane sulfonate silver hydrate (AgOSO 2 C 8 f 17 ·H 2 O), 0.01mmol perfluorooctane sulfonic acid (HOSO 2 C 8 f 17 ) and 3.0mLH 2 O, 1mmol phenylacetylene (R 1 = Ph, R 2 =H) Then the flask was placed in an oil bath reactor with magnetic stirring, and the reaction was carried out at 100° C. for 12 hours. After the reaction was completed, 5ml of n-hexane was added for extraction and separation, the catalyst water in the lower layer was repeatedly catalytically utilized, and the upper layer liquid was subjected to column chromatography to obtain the product acetophenone. The result of the reaction is: the yield of acetophenone is 83%. After the catalyst system can be reused 5 times, its catalytic performance is slightly reduced, and the yield is 70%.

preparation example 2

[0021] Add 0.05 mmol perfluorooctane sulfonate silver hydrate (AgOSO 2 C 8 f 17 ·H 2 O), 0.02mmol perfluorooctane sulfonic acid (HOSO 2 C 8 f 17 ) and 3.0mLH 2 O, 1mmol phenylacetylene (R 1 = Ph, R 2 =H) Then the flask was placed in an oil bath reactor with magnetic stirring, and the reaction was carried out at 100° C. for 12 hours. After the reaction was completed, 5ml of n-hexane was added for extraction and separation, the catalyst water in the lower layer was repeatedly catalytically utilized, and the upper layer liquid was subjected to column chromatography to obtain the product acetophenone. The reaction results are: the yield of acetophenone is 94%, and the selectivity is greater than 95%. After the catalyst system can be reused five times, its catalytic performance is slightly reduced, and the yield is 83%.

preparation example 3

[0023] Add 0.1 mmol perfluorooctane sulfonate silver hydrate (AgOSO 2 C 8 f 17 ·H 2 O), 0.02mmol perfluorooctane sulfonic acid (HOSO 2 C 8 f 17 ) and 3.0mLH 2 O, 1mmol phenylacetylene (R 1 = Ph, R2 =H) Then the flask was placed in an oil bath reactor with magnetic stirring, and the reaction was carried out at 100° C. for 12 hours. After the reaction was completed, 5ml of n-hexane was added for extraction and separation, the catalyst water in the lower layer was repeatedly catalytically utilized, and the upper layer liquid was subjected to column chromatography to obtain the product acetophenone. The result of the reaction is: the yield of acetophenone is 94%. After the catalyst system can be reused 5 times, its catalytic performance is slightly reduced, and the yield is 86%.

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Abstract

The invention provides a method for synthesizing a corresponding ketone through catalyzing and hydrolyzing an alkyne with silver perfluorooctanesulfonate. According to the method, water serves as a solvent, an alkyne serves as a raw material, silver perfluorooctanesulfonate serves as a main catalyst, and perfluorooctanesulfonic acid serves as an auxiliary catalyst, and reaction is carried out to synthesize a corresponding ketone. The method provided by the invention is an environment-friendly method for synthesizing a ketone by hydrolyzing an alkyne. The method has the advantages that the selectivity and yield of the target product are more than 90%, n-hexane or diethyl ether is added at the end of reaction to divide reactants into two phases, the catalysts can be reused directly in the water phase, the product of reaction is extracted and separated simply to obtain a corresponding ketone, and the whole reaction and separation processes are simple and environment-friendly.

Description

【Technical field】 [0001] The invention belongs to the field of catalysis, and in particular relates to a preparation method for ketone synthesis by catalyzing the hydrolysis of alkyne with perfluorooctane sulfonate silver hydrate, as well as catalyst recycling and product separation technology. 【Background technique】 [0002] Ketones are important key intermediates in organic synthesis. Synthesis of ketones by hydrolysis of terminal alkynes is one of the main methods for the synthesis of ketones. The commonly used classic preparation method is to prepare ketones by catalytic hydrolysis of terminal alkynes under a dose of mercury and acidic conditions, but this method causes huge pollution to the environment. [0003] In the past two decades, researchers have developed a series of methods for the preparation of ketones by hydrolysis of terminal alkynes, mainly including transition metal complex catalysis, such as: Ru, Pd, Sn-W, Au, Fe, Ir and Co, etc. Among these methods, a...

Claims

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Application Information

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IPC IPC(8): C07C45/42C07C49/78C07C49/76C07C49/84C07C49/807C07C49/80C07C49/258C07C49/543C07C49/04C07C49/215C07C49/213C07C255/56C07C253/30C07C201/12C07C205/45C07C205/37C07C225/22C07C221/00C07D307/46C07D319/06C07C69/738C07C67/313B01J31/22
Inventor 邱仁华李宁波许新华王金英张小红
Owner HUNAN UNIV
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