A kind of method that hydrophobic rhenium ionic liquid catalyzes olefin epoxidation

An ionic liquid and hydrophobic technology, applied in the direction of chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problem of high price, complicated process, non-recyclable reuse, etc. problems, to achieve the effect of protecting the environment and simple process

Inactive Publication Date: 2011-12-07
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In the traditional olefin epoxidation process, a large amount of organic solvents such as dichloromethane are used, not only the process is complicated, but also the yield is low. In addition, a large amount of organic solvents are directly discharged into nature, causing pollution to the environment
[0003] In order to increase the yield, catalysts are also used, but the catalysts are all solid catalysts, such as using methyl rhenium trioxide (MTO) as a catalyst to catalyze the epoxidation of olefins. Methyl rhenium trioxide is expensive and cannot be recycled and reused. high process cost

Method used

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  • A kind of method that hydrophobic rhenium ionic liquid catalyzes olefin epoxidation
  • A kind of method that hydrophobic rhenium ionic liquid catalyzes olefin epoxidation
  • A kind of method that hydrophobic rhenium ionic liquid catalyzes olefin epoxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the method for cyclopentene epoxidation catalyzed by hydrophobic rhenium ionic liquid

[0018] (1) Preparation of hydrophobic rhenium ionic liquid

[0019] Take 50g of heptylimidazole bromide, dissolve it in 300ml of deionized water, carry out ion exchange in hydroxyl resin, collect the effluent, add it to 1000ml of 10% (w / w) ammonium rhenate aqueous solution, and heat it at 70~90℃ Stir for 3 to 5 hours, remove water by rotary evaporation, add anhydrous methanol and acetonitrile mixed solution after cooling, seal and stir vigorously for 10 minutes, place at -30 to -40°C for 10 to 15 hours, distill under reduced pressure to remove methanol and acetonitrile , vacuum dried.

[0020] NMR characterization of hydrophobic rhenium ionic liquid figure 1 .

[0021] (2) Hydrophobic rhenium ionic liquid catalyzed cyclopentene epoxidation method

[0022] Preheat the hydrophobic rhenium ionic liquid with an oil bath to a reaction temperature of 50°C, add carbamide p...

Embodiment 2

[0023] Example 2 Cyclohexene epoxidation catalyzed by hydrophobic rhenium ionic liquid

[0024] (1) Preparation of hydrophobic rhenium ionic liquid

[0025] Same as Example 1

[0026] (2) Cyclohexene epoxidation catalyzed by hydrophobic rhenium ionic liquid

[0027] Preheat the hydrophobic rhenium ionic liquid with an oil bath to a reaction temperature of 60°C, add carbamide peroxide, the mole number of carbamide peroxide is 1.5 times the mole number of cyclohexene, and after mixing evenly, add cyclohexene, in which ions The mole number of the liquid is 80% of the mole number of cyclohexene, mechanically stirred under normal pressure, and the reaction time is controlled at 3 hours. After the reaction was finished, the product and substrate were extracted with n-hexane, the conversion rate of the upper layer was measured by gas chromatography, and its quantitative index was confirmed by the internal standard method to obtain a single product, which was the epoxide of the alke...

Embodiment 3

[0028] Example 3 Hydrophobic rhenium ionic liquid catalyzes the epoxidation of 1-hexene

[0029] (1) Preparation of hydrophobic rhenium ionic liquid

[0030] Same as Example 1

[0031] (2) Hydrophobic rhenium ionic liquid catalyzed the epoxidation of 1-hexene

[0032] Preheat the hydrophobic rhenium ionic liquid with an oil bath to a reaction temperature of 65°C, add carbamide peroxide, the molar number of carbamide peroxide is 2.5 times the molar number of 1-hexene, after mixing evenly, add 1-hexene, Wherein the mole number of the ionic liquid is 100% of the mole number of 1-hexene, mechanically stirred under normal pressure, and the reaction time is controlled at 3 hours. After the reaction was finished, the product and substrate were extracted with n-hexane, and the conversion rate of the upper layer was measured by gas chromatography, and its quantitative index was confirmed by the internal standard method to obtain a single product, which was the epoxide of the alkene, ...

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Abstract

The invention relates to a method for catalyzing epoxidation of olefins by hydrophobic rhenium ionic liquids. The technical scheme adopted is: use the hydrophobic rhenium ionic liquid as a catalyst, preheat the hydrophobic rhenium ionic liquid to 40-70°C, add an oxidizing agent, after mixing evenly, add the reaction substrate olefin, the number of moles of the hydrophobic rhenium ionic liquid It is 10-100% of the mole number of olefins, reacted for 1.5-3 hours under normal pressure, and extracted with n-hexane to obtain the target product. The invention has simple process, realizes homogeneous catalysis, the conversion rate is above 95%, the reaction is green and pollution-free, and the environment is protected. The catalyst can be recovered and recycled, and the conversion rate is still above 90% after 10 cycles.

Description

technical field [0001] The invention belongs to the field of chemical catalysis, and in particular relates to a method for catalyzing olefin epoxidation with hydrophobic rhenium ionic liquid. Background technique [0002] In the traditional olefin epoxidation process, a large amount of organic solvents such as dichloromethane are used, which is not only complicated in process, but also low in yield. In addition, a large amount of organic solvents are directly discharged into nature, causing pollution to the environment. [0003] In order to increase the yield, catalysts are also used, but the catalysts are all solid catalysts, such as using methyl rhenium trioxide (MTO) as a catalyst to catalyze the epoxidation of olefins. Methyl rhenium trioxide is expensive and cannot be recycled and reused. Cause high process cost. [0004] Ionic liquid is a green solvent that is odorless, non-polluting, easy to recycle, and can be recycled many times. Using ionic liquids as catalysts c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D301/19C07D303/04B01J31/02
Inventor 臧树良房大维
Owner LIAONING UNIVERSITY
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