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Method for synthesizing five ring carbonate using natural reproducible resource

A technology of cyclic carbonate and renewable resources, applied in the direction of organic chemistry, etc., can solve the problem of low conversion rate, and achieve the effect of simple method and improved catalytic effect.

Inactive Publication Date: 2008-12-03
SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Epoxidized soybean oil with CO from renewable resources 2 Synthesis of cyclic carbonates has also been reported: Tamami, J.Appl.Poly.Sci.2004, 92, 883 and Kenneth M.Doll, Green Chem.2005, 7, 849, in their work, too long reaction time And harsh supercritical conditions limit the application of this route. In our research, we found that using quaternary ammonium salts and lewis acids as catalysts can effectively catalyze this reaction, but the conversion rate is not high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Catalyst MgCl 2 After 0.31g and 1.04g of tetrabutylammonium chloride (molar ratio is 1:1) are dissolved in the solvent tetrahydrofuran, add it into an autoclave with a volume of 100ml equipped with a magnetic stirrer, a ventilation tube and a sampling tube, and add according to the proportion of the catalyst. Add 85g of epoxidized soybean oil to the epoxy group of epoxidized soybean oil in an amount of 2mol%, raise the temperature to 100°C, and start feeding CO 2 Gas, keep the pressure at 2atm, react for 20h, and discharge the material to obtain a brown liquid, then add 20g of ethyl acetate for extraction, wash with a large amount of water, dehydrate under vacuum at 90°C to obtain the product, and analyze and test the product. The epoxy value of the epoxidized soybean oil is 0.376, and the epoxy value of the product measured after the reaction is 0.098, and the conversion rate is 73.9%.

Embodiment 2

[0023] Catalyst ZnCl 2 After 0.88g and 1.04g of tetrabutylammonium bromide (molar ratio is 2: 1) are dissolved in the solvent pyrrolidone, add a volume that is equipped with magnetic stirring, ventilation tube and sampling tube in the autoclave that is 100ml, add according to the proportion of catalyst Add 85g of epoxidized soybean oil to the epoxy group of epoxidized soybean oil in an amount of 3mol%, raise the temperature to 120°C, and start feeding CO 2 Gas, keep the pressure at 8atm, react for 20h, and discharge the material to obtain a brown liquid, which is extracted by adding 20g of ethyl acetate, washed with a large amount of water, and dehydrated at 90°C under vacuum to obtain the product, which is analyzed and tested. The epoxy value of the epoxidized soybean oil is 0.376, and the epoxy value of the product measured after the reaction is 0.057, and the conversion rate is 84.8%.

Embodiment 3

[0025] Catalyst CoCl 2 ·6H 2 O0.77g and tetramethylammonium iodide 2.08g (molar ratio is 1: 2) are dissolved in solvent N, after N dimethylformamide, add a volume that is equipped with magnetic stirring, ventilation tube and sampling tube and be 100ml In the autoclave, add 85g of epoxidized soybean oil in an amount that the catalyst accounts for 3mol% of epoxy groups added to the epoxidized soybean oil, heat up to 140°C, and start feeding CO 2 Gas, keep the pressure at 15atm, react for 30h, and discharge the material to obtain a brown liquid, add 20g of ethyl acetate for extraction, wash with a large amount of water, dehydrate under vacuum at 90°C to obtain the product, and analyze and test the product. The epoxy value of the epoxidized soybean oil is 0.376, the epoxy value of the product measured after the reaction is 0.028, and the conversion rate is 92.6%.

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Abstract

The invention discloses a synthesizing method of five-membered ring carbonate through natural regenerating resource, which comprises the following steps: allocating quaternary ammonium salt and lewis acid with molar rate at 14-41; adding in the solvent until dissolving completely to obtain the catalyst solution; adding 2-5mol% epoxy soya oil and 100mol% catalyst in the reactor; aerating carbon dioxide under 2-20 atmosphere pressure at 120-160 deg. c; stirring to react for 20-40 h to obtain the product; extracting the product through acetic ester; washing; dehydrating.

Description

technical field [0001] The present invention relates to a kind of by natural renewable resource epoxidized soybean oil and CO 2 Method for generating five-membered cyclic carbonates. technical background [0002] Cyclic carbonates are used in a wide range of applications and are important raw materials for many plastic industries such as polycarbonate. As a member of cyclic carbonates, five-membered cyclic carbonates are widely used as monomers for synthetic polymers, organic polar solvents, intermediates for fine chemicals, electrode materials, and biochemical materials. The application fields of cyclic carbonates with longer chains also include fuels, lubricating oils, plastic additives, etc. In recent years, people have also used five-membered cyclic carbonates and primary amines to replace toxic isocyanates to generate non-isocyanate polyurethane (NIPU). [0003] The traditional synthesis of cyclic carbonates uses toxic phosgene, but efforts have been made to find som...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/34
Inventor 亢茂青李振荣赵雨花王军威王心葵
Owner SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI