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Method for catalytically oxidizing cyclic ketone

A technology for catalytic oxidation and cyclic ketones, which is applied in organic chemical methods, chemical instruments and methods, and oxidative preparation of carboxylic acids, etc., can solve the problems of non-compliance with the basic principles of green chemistry, difficult purification, and large environmental impact, and achieve extended reaction operation cycle, overcoming the complex production process, and the effect of high cyclic ketone conversion rate

Active Publication Date: 2012-05-16
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But peroxyacid oxidizing agent also has bigger shortcoming: (1) can produce a large amount of organic carboxylic acid (salt) wastes after finishing the reaction, has bigger impact on environment, and it is difficult to recycle or handle; (2) separation of reaction products , purification is more difficult, selectivity is low, atom economy is relatively poor, does not meet the basic principles of green chemistry; (3) organic peroxyacids need to use high-concentration hydrogen peroxide in the production process, the property is unstable, the production cost is higher, and It is more dangerous during transportation, storage and operation, thus limiting its application in industrial production
However, heteropolyacid catalysts have shortcomings such as unstable properties, small specific surface area, easy deactivation, difficult recovery and short service life, so they have not been widely promoted at present.

Method used

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  • Method for catalytically oxidizing cyclic ketone
  • Method for catalytically oxidizing cyclic ketone
  • Method for catalytically oxidizing cyclic ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Take by weighing 2.3 grams of tin-loaded acid-eluted aluminum nano-beta-molecular sieves (tin oxide content 3.1wt%, aluminum oxide content 2.4wt%) catalyst and put it in a 100ml three-necked flask, then add a magnetic stirrer, 19.63 grams of cyclohexane Ketone, 3.6 grams of water and 23ml of 30% hydrogen peroxide, the molar ratio of cyclohexanone to hydrogen peroxide is 1:1. The three-necked flask is placed on a temperature-controlled magnetic stirrer, and the upper part of the three-necked flask is condensed and refluxed with a condenser, and the magnetic stirrer and heating device are started to start the reaction. The reaction temperature was controlled at about 80°C. After 8 hours of reaction, the conversion rate of cyclohexanone was 60.65%, the selectivity of generating ε-caprolactone was 46.45%, the selectivity of 6-hydroxycaproic acid was 28.94%, and the The acid selectivity was 23.73%.

Embodiment 2

[0043] Take by weighing 2.44 grams of tin-loaded acid-eluting aluminum nano-beta-molecular sieve catalyst (tin oxide content 3.2wt%, aluminum oxide content 1.8wt%) and put it in a 100ml three-necked flask, then add a magnetic stirrer, 19.63 grams of cyclohexane Ketone, 30 grams of acetone and 23 ml of 30% hydrogen peroxide, the molar ratio of cyclohexanone to hydrogen peroxide is 1:1. The three-necked flask is placed on a temperature-controlled magnetic stirrer, and the upper part of the three-necked flask is condensed and refluxed with a condenser, and the magnetic stirrer and heating device are started to start the reaction. The reaction temperature was controlled at about 60°C, and after 1 hour of reaction, the conversion rate of cyclohexanone was 17.82%, the selectivity of forming ε-caprolactone was 96.65%, the selectivity of 6-hydroxycaproic acid was 1.46%, and the selectivity of hexanoic acid was 1.46%. Acid selectivity was 0.73%.

Embodiment 3

[0045] Take by weighing 2.65 grams of tin-loaded acid-eluting aluminum nano-beta-molecular sieve catalyst (tin oxide content 2.7wt%, aluminum oxide content 3.4wt%) and put it in a 100ml three-necked flask, then add a magnetic stirrer, 19.63 grams of cyclohexane Ketone, 18 grams of dioxane and 46ml of concentration are 30% hydrogen peroxide, and the molar ratio of cyclohexanone to hydrogen peroxide is 1:2. The three-necked flask is placed on a temperature-controlled magnetic stirrer, and the upper part of the three-necked flask is condensed and refluxed with a condenser, and the magnetic stirrer and heating device are started to start the reaction. The reaction temperature was controlled at about 73°C. After 5 hours of reaction, the conversion rate of cyclohexanone was 68.57%, the selectivity of forming ε-caprolactone was 97.98%, the selectivity of 6-hydroxycaproic acid was 0.64%, and the Acid selectivity was 0.32%.

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Abstract

The invention provides a method for catalytically oxidizing cyclic ketone. The method is characterized in that reaction is carried out in the presence of a catalyst under the conditions that molar ratio of cyclic ketone to solvent to hydrogen peroxide is 1: (0-50): (0.2-20), temperature is 5-200 DEG C and reaction pressure is 0.1-3.0MPa, wherein the catalyst is a tin-supported pickled aluminum nano Beta-molecular sieve and the mass ratio of the catalyst to the cyclic ketone is 1: (5-300).

Description

technical field [0001] The invention relates to a method for catalytically oxidizing cyclic ketones, more specifically to an environment-friendly method for oxidizing cyclic ketones in the presence of β molecular sieves through hydrogen peroxide. Background technique [0002] ε-caprolactone has the advantages of low viscosity, easy processing, and low VOC content. It is used as oligomer and denaturant in the process, which can improve the toughness, low temperature characteristics and reactivity and other functionalities; in terms of coatings, it is used as an improvement in solvents and latex coatings for automotive primers, surface coatings and various building materials. It can improve the toughness of the coating film, improve the low-temperature characteristics, reactivity, and increase the crosslinking density; in terms of adhesives, it can be used to improve the bonding properties of hot-melt adhesives and solvent-based adhesives; in resin modification On the one han...

Claims

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Application Information

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IPC IPC(8): C07B41/12C07B41/08C07D313/04C07D309/30C07C51/31C07C51/285C07C59/01C07C55/14C07C55/12
CPCY02P20/582
Inventor 夏长久朱斌林民龙立华邹飞艳舒兴田汝迎春
Owner CHINA PETROLEUM & CHEM CORP
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