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A method for catalyzing the cycloaddition reaction of three-membered heterocyclic compounds and carbon dioxide

A technology of heterocyclic compounds and carbon dioxide, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve problems such as the need to use solvents, harsh conditions, and large amounts of catalysts , to achieve the effects of environmental friendliness, mild reaction conditions and easy operation

Active Publication Date: 2019-02-05
HUIZHOU RES INST OF SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned catalytic systems all have disadvantages such as harsh conditions, large amount of catalyst, and the need to use solvents.
The conditions of the reaction are too harsh, however, the catalyst loading is 10mol% of the substrate but the system requires chloroform as a solvent

Method used

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  • A method for catalyzing the cycloaddition reaction of three-membered heterocyclic compounds and carbon dioxide
  • A method for catalyzing the cycloaddition reaction of three-membered heterocyclic compounds and carbon dioxide
  • A method for catalyzing the cycloaddition reaction of three-membered heterocyclic compounds and carbon dioxide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 10mL stainless steel autoclave, add 10mmol three-membered heterocyclic compound (general formula (II) structure, R1 is phenyl), add 0.01mmol of catalyst (in general formula (I), M is Al, n is 3, R is octyl), carbon dioxide is passed through, the pressure is 0.5MPa, and the temperature is 120 ° C. Stirring reaction is carried out. After the reaction is completed, ether is added to centrifuge to recover the catalyst. The supernatant is removed by rotary evaporation, and the product is obtained after vacuum drying Cyclic carbonate, yield 95%.

Embodiment 2

[0022] In a 10mL stainless steel autoclave, add 10mmol three-membered heterocyclic compound (general formula (II) structure, R 2 is propyl, R 3 is phenyl), add 0.1mmol of catalyst (M in the general formula (I) is Cr, n is 5, R is methyl), feeds carbon dioxide, pressure is 4.0MPa, is that stirring reaction is carried out at 30 ℃ at temperature, After the reaction, dichloromethane was added and centrifuged to recover the catalyst. The supernatant liquid was removed from the solvent by rotary evaporation, and the product oxazolidinone was obtained after vacuum drying with a yield of 92%.

Embodiment 3

[0024] In a 10mL stainless steel autoclave, add 10mmol three-membered heterocyclic compound (general formula (II) structure, R 1 is n-butyl), add 0.03mmol of catalyst (in the general formula (I), M is Zn, n is 6, R is ethyl), feeds carbon dioxide, pressure is 2.0MPa, and the stirring reaction is carried out at a temperature of 50°C , after the reaction, add chloroform and centrifuge to recover the catalyst, remove the solvent from the supernatant by rotary evaporation, and obtain the product cyclic carbonate after vacuum drying with a yield of 98%.

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Abstract

The invention discloses a method for catalyzing cycloaddition reaction of ternary heterocyclic compound and carbon dioxide. According to the method, a metalloporphyrin compound modified by imidazole ionic liquid is used as a catalyst, and cycloaddition reaction of ternary heterocyclic compound and carbon dioxid can be efficiently catalyzed with high selectivity under mild conditions. No solvent or cocatalyst is needed in the reaction process, the technology is simple, and the catalyst is easy to recycle.

Description

technical field [0001] The invention relates to a cycloaddition method of carbon dioxide, in particular to a method for catalyzing the cycloaddition of three-membered heterocyclopropane and carbon dioxide. Background technique [0002] With the intensification of the global warming effect and the development of organic chemistry, many scientific researchers will CO 2 As an environmentally friendly and cheap and readily available C1 resource, it is converted into various high value-added chemicals through chemical reactions. Among them, the reaction of epoxide and carbon dioxide to synthesize cyclic carbonate, or the reaction of aziridine and carbon dioxide to synthesize oxazolidinone has attracted the attention of chemists due to its 100% atom utilization and environmental friendliness. [0003] Cyclic carbonates are widely used in the fields of pesticides, medicines, resins, fuels, coatings, electronic chemicals, food additives and solvents, and are important fine chemical...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/36C07D263/22B01J31/22
CPCY02P20/584
Inventor 纪红兵周贤太杨智罗荣昌
Owner HUIZHOU RES INST OF SUN YAT SEN UNIV