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The method of styrene epoxidation reaction

A technology of epoxidation reaction and styrene, which is applied in chemical instruments and methods, organic chemistry, chemical/physical processes, etc., can solve the problems of poor catalyst stability and achieve the effects of good stability, low cost and excellent catalytic performance

Active Publication Date: 2016-04-06
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Kureshy et al. investigated the catalytic performance of Mn(II)-, Ru(II)-Schiff base complexes for the epoxidation of styrene, using Mn(II)-Schiff base complexes as catalysts, at a temperature of 25 °C, the reaction After 180min, the yield of styrene oxide is 42%, and with Ru (II)-Schiff base complex as catalyzer, the yield of styrene oxide is only 26%, and the stability of these two kinds of catalyzers is relatively poor

Method used

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  • The method of styrene epoxidation reaction
  • The method of styrene epoxidation reaction
  • The method of styrene epoxidation reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Weigh 10 millimoles of o-aminophenol, put it into a round-bottomed flask (50 milliliters) containing 20 milliliters of absolute ethanol, heat and stir at 50° C., add 10 millimoles of 2-acetylpyridine after the o-aminophenol is completely dissolved, and stir for 1 After 6 days, the light yellow polyhedral crystals were separated by suction filtration and washed with a small amount of ethanol to obtain 2-acetylpyridine o-aminophenol Schiff base complex.

[0021] Weigh 5mmol of 2-acetylpyridine-o-aminophenol, put it into a round-bottomed flask (50ml) containing 15ml of absolute ethanol, heat and stir at 75°C, and add 5mmol of acetylacetone after the 2-acetylpyridine-o-aminophenol is completely dissolved Molybdenum, stirred brown powder to precipitate, continue to heat and stir for 2 hours, then cool and suction filter, wash with ethanol and dry in vacuum at 40°C to obtain a brown powder product, its structural formula is as follows, and its infrared analysis spectrum is sho...

Embodiment 2

[0024] Weigh 10 mmol of o-aminophenol, put it into a round-bottomed flask (50 ml) containing 20 ml of pyridine, heat and stir at 50°C, add 10 mmol of 2-acetylpyridine after the o-aminophenol is completely dissolved, and stir for 1 hour After standing for 6 days, the light yellow polyhedral crystals were separated by suction filtration and washed with a small amount of ethanol to obtain 2-acetylpyridine o-aminophenol Schiff base complex.

[0025] Weigh 5mmol of 2-acetylpyridine-o-aminophenol, put it into a round-bottomed flask (50ml) containing 15ml of pyridine, heat and stir at 75°C, and add 5mmol of molybdenum acetylacetonate after the 2-acetylpyridine-o-aminophenol is completely dissolved. Stir brown powder to precipitate, continue to heat and stir for 2 hours, then cool and suction filter, wash with pyridine and dry in vacuum at 40°C to obtain the product. Its structural formula is as follows, and its infrared analysis spectrum is consistent with figure 1 resemblance.

[0...

Embodiment 3

[0028] Take 2.5mmol (0.29ml) of styrene, 5mmol (0.72ml) of tert-butyl hydroperoxide (TBHP), 6ml of benzene as solvent, and 0.025mmol of catalyst, put them into a 25ml one-necked flask, stir in an oil bath at 80°C, condense and reflux 9h. The molar ratio of styrene to catalyst was 100:1.

[0029] Reaction result: the conversion rate of styrene is 69.35%, and the selectivity of styrene oxide is 80.19%.

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Abstract

The invention relates to a styrene epoxidation reaction method, which mainly solves the problem that methods for catalyzing epoxidation of styrene by adopting a molybdenum Schiff alkali compound are undisclosed in the previous literatures. According to the method, tert-butyl hydroperoxide and styrene are taken as raw materials and are in contact with a catalyst for 1-24 hours to generate styrene oxide in the presence of a solvent at an ordinary pressure under the conditions that the reaction temperature is 30-120 DEG C, and the molar ratio of the tert-butyl hydroperoxide to the styrene is (1-20):1, wherein the catalyst is a 2-acetylpyridine o-aminophenol molybdenum complex, the chemical structural formula of the 2-acetylpyridine o-aminophenol molybdenum complex is shown in the specification, and in the formula, R is selected from -OHR2 or R2 is CnH2n+1, and n is 2-10. The method can be applied to the industrial production of styrene oxide prepared through styrene epoxidation reaction.

Description

technical field [0001] The invention relates to a method for styrene epoxidation reaction. Background technique [0002] Schiff base refers to a class of organic compounds containing imine or azimine characteristic groups (-RC=N-), which are formed by condensation of carbonyl and amino groups of aldehydes and ketones under certain conditions. Due to the hyperconjugation between the C=N bond and the benzene ring, such compounds are generally relatively stable. The benzene ring contains Schiff bases with coordination functional groups such as -OH and -N. The intramolecular hydrogen bonding makes it have a rigid structure, and it is very easy to form complexes with high-valent metals as multi-dentate ligands. Therefore, Schiff bases occupy an important position in coordination chemistry. [0003] Schiff bases are an important class of organic synthesis reagents and intermediates. Schiff base compounds and their metal complexes have important applications in the field of cata...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/04C07D301/19B01J31/22
Inventor 高焕新王戈金国杰宋纪元陶乔杨穆谭丽
Owner CHINA PETROLEUM & CHEM CORP
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