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Method for catalytic oxidation of cyclic ketone

A technology for catalytic oxidation and cyclic ketones, applied in organic chemistry methods, chemical instruments and methods, and oxidative preparation of carboxylic acids, etc. Good stability of oxidation activity and catalytic activity, overcoming the complex production process, and increasing the effect of mass transfer and diffusion rate

Active Publication Date: 2014-08-20
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the industrialized production of ε-caprolactone mainly adopts the Baeyer-Villiger oxidation process of cyclohexanone and peroxycarboxylic acid, but peroxyacid oxidants also have relatively large disadvantages: (1) after the reaction, a large amount of Organic carboxylic acid (salt) waste has a greater impact on the environment, and it is more difficult to recycle or process; (2) the separation and purification of reaction products are more difficult, the selectivity is low, the atom economy is poor, and it does not meet the basic principles of green chemistry; ( 3) Organic peroxyacids need to use high-concentration hydrogen peroxide in the production process, which is unstable in nature, high in production costs, and dangerous in 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 catalytic oxidation of cyclic ketone
  • Method for catalytic oxidation of cyclic ketone
  • Method for catalytic oxidation of cyclic ketone

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0043] This example illustrates the synthesis process of TS-1 molecular sieve and the synthesis process of tin-titanium-silicon molecular sieve according to the method of Zeolites, 1992, Vol.12, pages 943-950.

[0044]Mix 22.5 grams of tetraethyl orthosilicate with 7.0 grams of tetrapropylammonium hydroxide, add 59.8 grams of distilled water, mix well, and then hydrolyze at normal pressure and 60°C for 1.0 hour to obtain a hydrolysis solution of tetraethyl orthosilicate A solution consisting of 1.1 g of tetrabutyl titanate and 5.0 g of anhydrous isopropanol was slowly added under vigorous stirring, and the resulting mixture was stirred at 75° C. for 3 hours until it became a clear and transparent colloid. Put the colloid into a stainless steel sealed reaction kettle, and place it at a constant temperature of 170°C and autogenous pressure for 6 days to obtain a mixture of crystallized products; filter the mixture, wash it with water until the pH is 6-8, and dry it at 110°C Afte...

preparation example 2

[0046] Take the TS-1 molecular sieve obtained in Catalyst Preparation Example 1 according to the ratio of molecular sieve (g): sulfuric acid (mol): water (mol) = 100: 0.15: 15 and mix evenly, react at 90 ° C for 5.0 hours, and then follow the conventional method Filtration, washing and drying yielded acid-treated TS-1 molecular sieves.

[0047] The above-mentioned acid-treated TS-1 molecular sieves were mixed uniformly according to the ratio of molecular sieve (gram): triethanolamine (mol): tetrapropylammonium hydroxide (mol): water (mol) = 100: 0.20: 0.15: 180, and put into A stainless steel sealed reaction kettle was placed at a constant temperature of 190°C and autogenous pressure for 0.5 days. After cooling and pressure relief, it was filtered, washed, dried according to conventional methods, and roasted in an air atmosphere at 550°C for 3 hours to obtain a hollow structure molecular sieve.

[0048] According to X-ray diffraction analysis, it is a titanium-silicon molecula...

Embodiment 1

[0051] Weigh 2.3 grams of tin-containing titanium silicon molecular sieve Sn-TS-1 (SnO 2 The mass percentage is 2.1wt%, TiO 2 The mass percentage is 3.8wt%) to be installed in the 100ml three-necked flask, then add magnetic stirrer, 19.63 grams of cyclohexanone, 3.6 grams of water and 23ml concentration successively and be 30% hydrogen peroxide, now cyclohexanone and hydrogen peroxide The molar ratio 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 72°C. After 4 hours of reaction, the conversion rate of cyclohexanone was 30.65%, the selectivity of generating ε-caprolactone was 36.70%, the selectivity of 6-hydroxycaproic acid was 41.34%, and the Acid selectivity was 13.21%.

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Abstract

The invention discloses a method for catalytic oxidation of cyclic ketone, wherein reacting cyclic ketone, solvent and hydrogen peroxide based on a mole proportion of cyclic ketone: solvent: hydrogen peroxide=1:(0-8): (0.2-20) at 5-20 degrees centigrade and a 0.1-3.0 MPa reaction pressure in the presence of a catalyst and recycling the product, wherein the mass ratio of the catalyst to the cyclic ketone is 1:(5-30), and the catalyst is a tin titanium silicate molecular sieve.

Description

technical field [0001] The invention relates to a catalytic method for cyclic ketones, and more particularly relates to a method for oxidizing cyclic ketones with 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 hand, it can be used to improve softness, fluidity, low temperatu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B41/12C07B41/08C07D313/04C07D309/30C07C51/31C07C51/285C07C59/01C07C55/14C07C55/12
CPCY02P20/582Y02P20/584
Inventor 夏长久林民朱斌龙立华舒兴田邹飞艳汝迎春
Owner CHINA PETROLEUM & CHEM CORP
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