Alpha,beta-unsaturated ketone or arone environment-friendly synthesis method

A green synthesis and unsaturated technology, applied in the α field, can solve the problems of large catalyst consumption, difficult post-processing, and easy pollution, and achieve the effects of low production cost, environmental friendliness, and pollution prevention

Active Publication Date: 2009-06-03
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the shortcomings of the prior art in the preparation of α, β-unsaturated ketones or aryl ketones, the catalyst consumption is large, the cost is high, the post-treatment is difficult, and it is easy to cause pollution. The invention provides a catalyst with reasonable process and high reaction yield. A green chemical synthesis method for α, β-unsaturated ketones or aromatic ketones with low consumption, convenient recycling, low production cost, clean and environment-friendly

Method used

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  • Alpha,beta-unsaturated ketone or arone environment-friendly synthesis method
  • Alpha,beta-unsaturated ketone or arone environment-friendly synthesis method
  • Alpha,beta-unsaturated ketone or arone environment-friendly synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0035] In a 2500ml four-neck flask equipped with a thermometer and mechanical stirring, add 168g (1mol) of diphenylmethane, 60g of N-hydroxysuccinimide, azobisisobutylcyanide (AIBN, 0.5g), and use 1800ml of acetic acid Ethyl ester / butanone (V / V=1:1) mixed solvent was dissolved and stirred, heated to 70°C, and air was introduced at V=1.5ml / min. The reaction temperature was maintained and stirred for 12 hours. Cool to below 0°C, and fully stir for 30 minutes, then stand still for 10 minutes, and filter to obtain 55 g of catalyst for filter cake recovery. The filtrate was transferred to a 2500ml three-necked flask, 10ml of triethylamine and 15g of ferrous sulfate were added, heated to 70°C and stirred for 24 hours. Cool to room temperature, add 5% dilute hydrochloric acid to make the pH value ≤ 5, separate the liquids, wash the upper transparent solution with water and concentrate to obtain a light yellow solid, which is recrystallized with 80% ethanol to obtain 166g of pure pro...

Embodiment 2

[0037] In a 2500ml four-necked bottle equipped with a thermometer and mechanical stirring, add 168g (1mol) of diphenylmethane, 60g of N-hydroxymaleimide, azobisisobutylcyanide (AIBN, 0.5g), and use 1800ml of acetic acid Ethyl ester / butanone (V / V=1:1) mixed solvent was dissolved and stirred, heated to 70°C, and air was introduced at V=1.5ml / min. The reaction temperature was maintained and stirred for 12 hours. Cool to below 0°C, and fully stir for 30 minutes, then stand still for 10 minutes, and filter to obtain 52.5 g of catalyst for filter cake recovery. The filtrate was transferred to a 2500ml three-necked flask, 10ml of triethylamine and 15g of ferrous sulfate were added, heated to 70°C and stirred for 24 hours. Cool to room temperature, add 5% dilute hydrochloric acid to make the pH value ≤ 5, separate the liquids, wash the upper transparent solution with water and concentrate to obtain a light yellow solid, which is recrystallized with 80% ethanol to obtain 155g of pure ...

Embodiment 3

[0039]In a 2500ml four-necked bottle equipped with a thermometer and a mechanical stirrer, add 168g (1mol) of diphenylmethane, 85g of N-hydroxyphthalimide, and azobisisobutylcyanide (AIBN, 0.5g). 1800ml of ethyl acetate / butanone (V / V=1:1) mixed solvent was dissolved and stirred, heated to 70°C, and air was introduced at V=1.5ml / min. The reaction temperature was maintained and stirred for 12 hours. Cool to below 0°C, and fully stir for 30 minutes, then stand still for 10 minutes, and filter to obtain 82.5 g of catalyst for filter cake recovery. The filtrate was transferred to a 2500ml three-necked flask, 10ml of triethylamine and 15g of ferrous sulfate were added, heated to 70°C and stirred for 24 hours. Cool to room temperature, add 5% dilute hydrochloric acid to make the pH value ≤ 5, separate the liquids, wash the upper transparent solution with water and concentrate to obtain a light yellow solid, which is recrystallized with 80% ethanol to obtain 146g of pure product with...

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Abstract

The invention discloses a green synthesizing method of alpha, beta-unsaturated ketone or aromatic ketone, which is characterized by the following: adopting relative unsaturated hydrocarbons or aromatic hydrocarbons as raw material; setting imide as catalyst; making azobisisobutyronitrile (AIBN) or benzoyl peroxide (BPO) as initiator; oxidizing in the organic solvent; dehydrating through dehydrant; separating and purifying to obtain the alpha, beta-unsaturated ketone; improving reacting receiving rate; reducing manufacturing cost; possessing mild reacting condition; using little catalyst; avoiding pollution.

Description

(1) Technical field [0001] The invention relates to a green synthesis method of α, β-unsaturated ketones or aromatic ketones, in particular to a green chemistry for preparing α, β-unsaturated ketones or aromatic ketones by using air or oxygen-enriched air or oxygen as a clean oxidant resolve resolution. This series of products are widely used in the synthesis of medicines, pesticides and dyes, and have high practical value and economic benefits. (2) Background technology [0002] Before the present invention was made, the synthesis of α, β-unsaturated ketones or aryl ketones in the prior art was prepared by using traditional oxidants such as high-valent chromium salts, chromium trioxide, and periodides. Such as J.Org.Chem.1969, 3587, proposed to use 25 equivalents of CrO 3 / pyridine is used as an oxidizing agent to obtain the target product, and the yield is about 70%; Syn.Commun.1987, 1227, proposes to use 25 equivalents of PCC (pyridine chlorochromate) as an oxidizing ag...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/587C07C49/76C07C45/32C07J7/00C07D333/22C07D307/12C07D207/333C07B41/06
Inventor 苏为科金灿刘建刚闻光东
Owner ZHEJIANG UNIV OF TECH
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