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Method for preparing cyclic carbonate from carbon dioxide and epoxy compound through cycloaddition

A technology for epoxy compounds and cyclic carbonates, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve the problems of complex preparation process and high catalyst cost, To achieve the effect of good selectivity, low price and cost reduction

Inactive Publication Date: 2012-12-19
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most catalysts need to add co-catalysts, the preparation process is complicated, and the cost of some catalysts is relatively high

Method used

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  • Method for preparing cyclic carbonate from carbon dioxide and epoxy compound through cycloaddition

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preparation example

[0021] (1) References Mukhopadhyay M, Reddy M M, Maikap G C, et al. Journal of Organic Chemistry , 1996, 60: 2670~2676, preparation of catalyst ligand bisfural formaldehyde ortho-phenylenediamine by reaction of o-phenylenediamine and furan formaldehyde: take 1.92g (20mmol) 2-furan formaldehyde dissolved in 10mL absolute ethanol, stir at room temperature Next, a solution of 1.08g (10mmol) of o-phenylenediamine dissolved in 10mL of absolute ethanol was slowly added to the 2-furan carboxaldehyde ethanol solution. Continue to stir the reaction at room temperature for 5 hours, let it stand overnight, extract with petroleum ether, and obtain pale yellow needle-like crystals, which are the catalyst ligand bisfurylformaldehyde-o-phenylenediamine. 1 H NMR (400 MHz, CDCl 3 ): δ 7.80,6.24(m, 6H, furan H ), 7.48(s, 2H, -CH=N), 7.46, 7.22(m, 4H, Ph H). Infrared ν (cm -1 ): 1642 (C=N), 1564, 1508, 1392 (aromatic ring), 1287 (C-O-C). Melting point: 94-97°C. Elemental Analysis C 16 h 1...

Embodiment 1

[0027] will be 0.1×10 -3 Put the molar bisfural formaldehyde acetal o-phenylenediamine zinc complex catalyst into a pre-dried 100mL stainless steel autoclave, vacuumize, replace the air in the autoclave with high-purity nitrogen, and add purified propylene oxide into the autoclave with a syringe 0.02 moles, heated up to 85°C, and introduced CO 2 to 1.5MPa, stirred for 10 hours, then lowered the temperature to stop the reaction. After the reaction system is cooled, the remaining gas is released, distilled, and the distillate is collected around 34°C to obtain propylene oxide, and then continue to heat up and distill until there is no distillate, and the obtained colorless liquid is propylene carbonate .

[0028] The yield of propylene carbonate analyzed by gas chromatography was 83%.

[0029] The distillation residue is transferred to an autoclave to be used as a catalyst for the next catalytic reaction.

[0030] The catalyst was directly reused 4 times, and the yields of p...

Embodiment 2

[0033] Will 1×10 -3 Put the molar bisfural formaldehyde acetal o-phenylenediamine zinc complex catalyst into a pre-dried 2L stainless steel autoclave, vacuumize, replace the air in the autoclave with high-purity nitrogen, and add purified propylene oxide into the autoclave with a syringe 10 moles, heated up to 85°C, and introduced CO 2 to 5MPa, stirred for 36 hours, then cooled down to stop the reaction. After the reaction system is cooled, the remaining gas is released, distilled, and the distillate is collected around 34°C to obtain propylene oxide, and then continue to heat up and distill until there is no distillate, and the obtained colorless liquid is propylene carbonate .

[0034] The yield of propylene carbonate analyzed by gas chromatography was 71%.

[0035] The distillation residue is transferred to an autoclave to be used as a catalyst for the next catalytic reaction.

[0036] The catalyst was directly reused 4 times, and the yields of propylene carbonate were ...

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Abstract

The invention specifically discloses a method for preparing cyclic carbonate from carbon dioxide and an epoxy compound through cycloaddition, which belongs to the technical field of organic synthesis. A difuran formaldehyde-1,2-phenylenediamine zinc complex is used as a catalyst in the method. Compared with the prior art, the invention has the following advantages: 1, furan formaldehyde (usually called as furfural) is prepared from corncobs or rice bran, so furan formaldehyde is cheap and is not a petrochemical product, and when furan formaldehyde is used to replace salicylaldehyde and diamine compounds for preparation of Schiff alkali ligand through a reaction, cost can be reduced and requirements of green chemistry are met; 2, the catalyst has the advantages of easily available raw materials, simple preparation, a stable structure, high catalytic efficiency and good selectivity; 3, when the catalyst provided by the invention is used for preparation of cyclic carbonate, catalytic reaction conditions are relatively mild and operation is easy; 4, no organic solvent is added in the reaction, and a product can be easily separated; and 5 5, the product and the catalyst can be easily separated, and the catalyst can be reused.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing cyclic carbonates by cycloaddition of carbon dioxide and epoxy compounds. Background technique [0002] Cyclic carbonate is a high boiling point, aprotic polar organic solvent and organic synthesis intermediate with excellent performance. It is widely used in the fields of fine chemical synthesis, urea decarburization, gas separation, battery electrolyte and metal extraction. At the same time, it is also the raw material for the production of dimethyl carbonate by transesterification and the preparation of high polymers by ring-opening polymerization. Cyclic carbonates include macrocyclic carbonates with five-membered rings, six-membered rings, seven-membered rings and more than seven-membered rings, among which five-membered ring carbonates are the most widely used. The preparation methods of cyclic carbonate mainly include phosgene ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/36B01J31/22
Inventor 秦刚范利丹曹少魁杨政鹏王李波
Owner HENAN POLYTECHNIC UNIV
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