Preparation method of cyclic carbonate and preparation method of sulfonamide bifunctional quaternary ammonium salt catalyst

A cyclic carbonate and catalyst technology, applied in the field of preparation of cyclic carbonate, can solve the problems of poor selectivity, oxidation, and easy hydrolysis, etc., and achieve the effects of improving reaction efficiency, avoiding toxicity, and simple equipment

Pending Publication Date: 2022-01-28
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The currently used catalyst types mainly include quaternary ammonium salts, alkali metal halides, organophosphorus salts, ionic liquids, transition metal complexes, metal oxides, molecular sieves, supported metal halides, supported metal complexes, etc., many of which Catalysts have poor selectivity, are easily hydrolyzed or oxidized and are toxic, and most organic catalysts often require high temperature (>100°C) and pressure (>10atm)

Method used

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  • Preparation method of cyclic carbonate and preparation method of sulfonamide bifunctional quaternary ammonium salt catalyst
  • Preparation method of cyclic carbonate and preparation method of sulfonamide bifunctional quaternary ammonium salt catalyst
  • Preparation method of cyclic carbonate and preparation method of sulfonamide bifunctional quaternary ammonium salt catalyst

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Catalyst precursor - synthesis of aziridine:

[0088] Add 4-dimethylaminopyridine (DMAP, 0.1 equiv) to a solution of glycinol (20 mmol) and triethylamine (TEA, 3.5 equiv.) in anhydrous acetonitrile (120 mL) at 0°C; then slowly add p-toluenesulfonyl chloride (2.0equiv.), keep the reaction liquid milky white during the process. After the p-toluenesulfonyl chloride was added dropwise, the reaction mixture was stirred for 30 minutes to warm up to room temperature, and the reaction was continued for 5-7 hours. After the reaction was completed, the reaction solution was spun out of the solvent to obtain a light yellow emulsion, which was then dissolved with 200 mL of ethyl acetate. Wash the organic phase with saturated sodium chloride solution (80 mL) 3 times, and dry the organic phase with anhydrous magnesium sulfate overnight, remove the anhydrous magnesium sulfate by filtration, and concentrate the filtrate by rotary evaporation. The obtained crude product was purified b...

Embodiment 2

[0094] Catalyst precursor - synthesis of aziridine:

[0095] At 0°C, add 4-dimethylaminopyridine (DMAP, 0.1 equiv) to a solution of valinol (20 mmol) and triethylamine (TEA, 3.5 equiv.) in anhydrous acetonitrile (120 mL); then slowly drop p-toluenesulfonyl chloride (2.0equiv.), keep the reaction liquid milky white during the process. After the p-toluenesulfonyl chloride was added dropwise, the reaction mixture was stirred for 30 minutes to warm up to room temperature, and the reaction was continued for 5-7 hours. After the reaction was completed, the reaction solution was spun out of the solvent to obtain a light yellow emulsion, which was then dissolved with 200 mL of ethyl acetate. Wash the organic phase with saturated sodium chloride solution (80 mL) 3 times, and dry the organic phase with anhydrous magnesium sulfate overnight, remove the anhydrous magnesium sulfate by filtration, and concentrate the filtrate by rotary evaporation. The obtained crude product was purified ...

Embodiment 3

[0101] Catalyst precursor - synthesis of aziridine:

[0102] At 0°C, to phenylglycinol (20mmol) and K 2 CO 3 (4.0 equiv.) Add anhydrous acetonitrile (120mL) to dissolve; then slowly add p-toluenesulfonyl chloride (dissolve in anhydrous acetonitrile) (2.0equiv.), keep the reaction liquid milky white during the process. After the p-toluenesulfonyl chloride was added dropwise, the reaction mixture was stirred for 30 minutes to warm up to room temperature, and the reaction was continued for 5-7 hours. After the reaction was completed, the reaction solution was spun out of the solvent to obtain a white emulsion, and then toluene was added dropwise (stopped when the organic layer and the solid layer were separated). The obtained crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate=10 / 1) to finally obtain aziridine 33 as a white powder.

[0103] Catalyst Synthesis:

[0104] Dry the flask and add the rotor, then add aziridine 33 (3mmol), Yb...

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Abstract

The invention discloses a preparation method of cyclic carbonate and a preparation method of a catalyst, and belongs to the technical field of green catalytic synthesis. The invention designs an artificially synthesized organic catalyst derived from a natural alpha-amino acid raw material. R2 groups in the catalyst are side chain R groups of glycine, valine, phenylglycine and phenylalanine, a catalyst structure with better activity is obtained through a preliminary screening experiment, R1 and R3 groups in the catalyst structure are further modified, and the catalyst with optimal activity is screened out. Finally, through reaction condition optimization and substrate range screening, the efficient catalytic activity of the organic catalyst for catalyzing epoxide to prepare cyclic carbonate under mild conditions is verified.

Description

technical field [0001] The invention belongs to the technical field of green catalytic synthesis, and in particular relates to a preparation method of a cyclic carbonate and a preparation method of a catalyst thereof. Background technique [0002] Cyclic carbonates, or organic cyclic carbonates, are a value-added product synthesized from atmospheric carbon dioxide and can be used as intermediates in fine chemical synthesis, electrolytes and polar aprotic solvents in lithium-ion batteries, and can also be used For the synthesis of important polymers such as polycarbonate and polyurethane. However, under the premise of no catalyst addition, the conversion rate of the raw material epoxide is only low even under high temperature and high pressure conditions, and its reaction activity has been significantly improved after adding a small amount of catalyst. In view of its wide range of applications and strong economic potential, there is an urgent need to improve its synthesis co...

Claims

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Application Information

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IPC IPC(8): C07D317/38C07D317/36B01J31/02C07D213/26C07D213/04
CPCC07D317/36C07D317/38B01J31/0271B01J31/0244C07D213/04C07D213/26
Inventor 郭凯张奔何军吕湛李振江孙戒胡永铸高罗玉刘博
Owner NANJING UNIV OF TECH
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