Method for preparing ketone compound from olefin

A technology of ketone compounds and olefins, applied in the field of organic chemical synthesis, can solve problems such as high cost, environmental problems, and limitations on the practicality of Wacker reactions, and achieve the effect of simple synthesis and low price

Active Publication Date: 2021-08-17
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the Wacker reaction usually uses expensive divalent palladium salts as catalysts, and sometimes requires high catalyst loading, which leads to high cost and environmental problems, which limit the practicality of the Wacker reaction.

Method used

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  • Method for preparing ketone compound from olefin
  • Method for preparing ketone compound from olefin
  • Method for preparing ketone compound from olefin

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0015] Ligand preparation method:

[0016]

[0017] Add hydrazide (10mmol), pyridine formaldehyde (10mmol) and solvent methanol (20mL) into the reaction flask, add elemental iodine (0.5mmol) under stirring, and reflux reaction in the presence of air for 8 hours. After the reaction, add water and ethyl acetate The ester was extracted three times. The water layer was removed, and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized with 20 mL of ethanol to obtain the ligand.

Embodiment 1

[0018] Embodiment 1 (preparation of ligand L1)

[0019]

[0020] The hydrazide is selected from acetylhydrazide, the pyridine formaldehyde is selected from pyridine-2-carbaldehyde, and the ligand L1 is prepared according to the method of implementation one. 1 HNMR: δ8.59(d, J=7.5Hz, 1H), 8.01(d, J=7.5Hz, 1H), 7.85(dd, J=7.5, 7.5Hz, 1H), 7.42(dd, J=7.5, 7.5Hz,1H),2.63(s,3H). 13 C NMR: δ164.7, 164.5, 157.4, 149.2, 137.2, 124.2, 123.6, 20.5.

Embodiment 2

[0021] Embodiment 2 (preparation of ligand L2)

[0022]

[0023] The hydrazide is selected from benzohydrazide, the pyridine formaldehyde is selected from 4-methoxypyridine-2-carbaldehyde, and the ligand L2 is prepared according to the method of implementation one. 1 H NMR: δ8.61(d, J=7.5Hz, 1H), 7.98(m, 2H), 7.73(d, J=7.5Hz, 1H), 7.62(m, 3H), 7.43(s, 1H), 3.81(s,3H). 13 C NMR: δ164.8, 164.4, 159.4, 158.3, 150.2, 133.7, 129.3, 129.1, 128.7, 127.7, 127.5, 107.9, 105.4, 55.8.

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and discloses a method for preparing a ketone compound from olefin by using an iron catalyst. According to the invention, the ligand and the iron salt form an iron catalyst in the on-site reaction, the raw materials in the formula are easy to obtain, and the synthesis is simple. By using the catalyst, olefin can be efficiently converted into ketone compounds, and compared with a palladium catalyst, the price is very low, and the catalyst is suitable for industrial application.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for preparing ketone compounds from olefins realized by an iron catalyst. Background technique [0002] Olefins can be produced in large quantities from petroleum resources and are a very abundant chemical feedstock. Therefore, they have been used as starting materials for the synthesis of a large number of fine chemicals, and the oxidation of alkenes has become one of the most direct routes to the synthesis of aldehydes and ketones. The Wacker process represents a milestone in the utilization of olefins by industrially catalyzing the oxidation of ethylene to acetaldehyde through the combination of palladium and copper. Since the discovery of this method, the Pd / Cu catalyst system has been extended to the oxidation of various terminal alkenes (Wacker-Tsuji oxidation) and provides a very efficient method for the synthesis of methyl ketones....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/04C07C45/34C07C49/76C07C49/84C07C49/403B01J31/22
CPCC07C45/34B01J31/1815C07C2601/14B01J2531/842B01J2231/70B01J2531/0213C07C49/04C07C49/76C07C49/84C07C49/403
Inventor 朱纯银曹洋张欣
Owner JIANGSU UNIV
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