Method for catalytically oxidizing cyclic olefin

A technology for catalytic oxidation and cyclic olefins, which is applied in the direction of organic chemical methods, chemical instruments and methods, and oxidative preparation of carboxylic acids, etc. It can solve the problems of short service life, difficulty in recycling, and unstable properties of heteropolyacid catalysts, and achieve the goal of overcoming production problems. craft complex effects

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

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 olefin
  • Method for catalytically oxidizing cyclic olefin
  • Method for catalytically oxidizing cyclic olefin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Take by weighing 3.45 grams of hollow titanium-silicon molecular sieves (produced by Hunan Jianchang Petrochemical Company, brand HTS, analyzed by X-ray diffraction to be the titanium-silicon molecular sieve of MFI structure, the adsorption isotherm and the desorption isotherm of the low-temperature nitrogen adsorption of this molecular sieve are between There is a hysteresis ring, the grains are hollow grains and the radial length of the cavity part is 15-180 nanometers; the molecular sieve sample is at 25°C, P / P 0 =0.10, the benzene adsorption measured under the condition of adsorption time 1 hour is 78 mg / g, the same below) is installed in the 100ml three-necked flask, then adds magnetic stirrer, 4.12 grams of cyclohexene, 3.6 grams of water and 23ml concentration is 30% hydrogen peroxide, and the molar ratio of cyclohexene and hydrogen peroxide is 1:4 at this moment. The three-necked flask is placed on a temperature-controlled magnetic stirrer, and the upper part of...

Embodiment 2

[0037] Weigh 4.88 grams of hollow titanium-silicon molecular sieves and put them in a 100ml three-necked flask, then add a magnetic stirrer, 4.12 grams of cyclohexene, 6.4 grams of methanol and 46ml of hydrogen peroxide with a concentration of 30%. The molar ratio is 1:8. 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 75° C., and after 2.5 hours of reaction, the conversion rate of cyclohexene was 32.08%, and the selectivity to ε-caprolactone was 23.64%. The selectivity of ε-caprolactone was 45.82%. The selectivity to 6-hydroxycaproic acid was 23.67%, and the selectivity to adipic acid was 21.89%.

Embodiment 3

[0039] Weigh 2.65 grams of hollow titanium-silicon molecular sieves and put them in a 100ml three-necked flask, then add a magnetic stirrer, 16.48 grams of cyclohexene, 7.41 grams of tert-butanol, 6.4 grams of methanol and 23ml of hydrogen peroxide with a concentration of 30%. The molar ratio of hexene 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 68°C. After 3 hours of reaction, the conversion rate of cyclohexene was 8.57%, and the selectivity of ε-caprolactone was 25.37%. The selectivity to 6-hydroxycaproic acid was 46.43%, and the selectivity to adipic acid was 15.33%.

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Abstract

The invention provides a method for catalytically oxidizing cyclic olefin. The method is characterized in that reaction is carried out in the presence of a catalyst under the conditions that molar ratio of cyclic olefin to solvent to hydrogen peroxide is 1: (0-80): (0.2-20), temperature is 5-200 DEG C and reaction pressure is 0.1-3.0MPa and products are recovered, wherein the mass ratio of the catalyst to the cyclic olefin is 1: (5-300) and the catalyst is a titanium-silicon molecular sieve.

Description

technical field [0001] The invention relates to a method for catalyzing the oxidation of cyclic olefins, more specifically to a method for catalyzing the oxidation of cyclic olefins with hydrogen peroxide as an oxidant. 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 hand, it can be used to improv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/12C07B41/08C07D313/04C07D309/30C07C51/31C07C51/285C07C59/01C07C55/14C07C55/12
Inventor 林民朱斌夏长久龙立华邹飞艳舒兴田汝迎春
Owner CHINA PETROLEUM & CHEM CORP
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