A kind of highly active bifunctional catalyst and its preparation method and application

A dual-functional catalyst and high-activity technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve the problem of reduced reaction rate, difficult chiral cyclic carbonic Ester synthesis and other issues

Active Publication Date: 2015-10-07
SHENYANG GOLD JYOUKI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the reaction temperature or pressure is reduced, the reaction rate is likely to drop significantly, and some systems are accompanied by the formation of by-products such as polycarbonate and polyether.
In addition, the above catalysts are usually difficult to use in the synthesis of chiral cyclic carbonates

Method used

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  • A kind of highly active bifunctional catalyst and its preparation method and application
  • A kind of highly active bifunctional catalyst and its preparation method and application
  • A kind of highly active bifunctional catalyst and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] Compound b: In a 100mL round-bottomed flask, compound 1 (3.60g, 10.0mmol) and anhydrous potassium carbonate (1.5g, 12.0mmol) were dissolved in 50mL refined acetonitrile, and refined diethylamine (1.7mL, 12.0mmol) was added, Reacted at 80°C for 24 h, followed the reaction by TLC until no raw materials remained, stopped the reaction, cooled the reaction liquid to room temperature, filtered, and removed the solvent under reduced pressure to obtain the crude product as a white turbid liquid. Dissolve it in 10ml of ethyl acetate, add 40mL of 2mol / L dilute hydrochloric acid solution, and stir vigorously for 0.5h. The aqueous phase was separated, the organic phase was extracted with water (20 mL×3), the aqueous phases were combined, and saturated sodium bicarbonate solution was slowly added to make it alkaline to pH=8, and extracted with dichloromethane (50 mL×3). The combined organic phases were washed with saturated brine (200 mL×1), dried over anhydrous sodium s...

Embodiment 2

[0074]

[0075] Compound g: In a 100mL round bottom flask, ethylenediamine monohydrochloride (0.19g, 2.0mmol) and 3,5-di-tert-butyl salicylaldehyde (0.47g, 2.0mmol) were dissolved in 30mL of anhydrous methanol, join in Molecular sieve. After reacting at 20°C for 2 h, refined triethylamine (0.27 mL, 2.0 mmol) and compound d (0.87 g, 2.0 mmol) were added, and 30 mL of ethanol was added, and stirring was continued for 4 h. Stop the reaction, filter with suction, wash the filter cake with dichloromethane, and remove the solvent from the filtrate under reduced pressure to obtain a crude product. Separation and purification by column chromatography (silica gel column; developer volume ratio: petroleum ether / ethyl acetate / triethylamine=100 / 10 / 1) to obtain compound g as a yellow solid (yield: 0.49g, yield: 38 %).

[0076] 'H NMR (400MHz, CDCl 3 )δ13.51(s,1H),13.36(s,1H),8.35(s,1H),8.32(s,1H),7.29(s,1H),7.19(s,1H),7.07(s,1H ),7.01(s,1H),3.84–3.89(m,4H),3.46–3.49(m,4H),3.32–3.3...

Embodiment 3

[0084] In a stainless steel autoclave with a volume of 200mL, add it in the following order at ambient temperature: the catalyst is dissolved in alkylene oxide, the system is heated to the set temperature, and then carbon dioxide gas is fed to the set pressure (maintained during the reaction). Constant pressure), after reacting for a certain period of time under stirring, the unreacted carbon dioxide in the reactor was slowly released, and the residue was analyzed by infrared spectrum and nuclear magnetic spectrum, and no by-products such as polycarbonate and polyether were found. The cyclic carbonate was distilled off under reduced pressure, and the purity of the product was determined by gas phase or liquid chromatography and nuclear magnetic resonance spectroscopy. It was found that the selectivity of the cyclic carbonate in all systems was higher than 99.5%. See Table 1 to Table 6.

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Abstract

The invention relates to a high-activity double-function catalyst as well as a preparation method and application of the high-activity double-function catalyst. The catalyst is a tetradentate schiff base aluminum complex and the molecule contains more than one quaternary ammonium salt or quaternary phosphonium salt radical. Under a low catalyst concentration, the high-activity double-function catalyst still has the higher catalytic activity; reaction conditions are relatively moderate and a process is simple and convenient; the catalytic efficiency is high and the product selectivity is high; any organic solvent does not need to be added; and when chiral epoxyalkane is used as a reactant, the optical purity of a product can be completely kept.

Description

Technical field: [0001] The invention relates to a catalyst for synthesizing cyclic carbonate, in particular to a highly active bifunctional catalyst for catalyzing and activating carbon dioxide and alkylene oxide to synthesize cyclic carbonate, a preparation method and application thereof. Background technique [0002] carbon dioxide (CO 2 ) As an important carbon source on the earth, it is converted into carbohydrates through photosynthesis and releases oxygen at the same time, which is one of the most important reactions to maintain the ecological cycle. However, in human daily life and industrial production, CO 2 Excessive emissions of the 2 become the main gas that causes the greenhouse effect. Therefore, CO 2 It is an important research direction of green chemistry that carbon-resources are chemically fixed and transformed into useful fine chemicals. Under the action of catalyst, carbon dioxide can react with alkylene oxide to prepare cyclic carbonate. These cycl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22B01J31/24C07F5/06C07D317/38C07D317/36
Inventor 任伟民于凯徐桅吕小兵
Owner SHENYANG GOLD JYOUKI TECH
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