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Application of morpholine-containing ionic compound serving as catalyst for synthesizing cyclic carbonate

A cyclic carbonate and morpholine technology is applied in the field of catalysts for synthesizing cyclic carbonates, and achieves the effects of low energy consumption, environmental friendliness and clean process

Inactive Publication Date: 2013-11-27
WUHAN IL CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no morpholine-based ionic liquid or ionic liquid crystal has been used as a catalyst system to catalyze the synthesis of cyclic carbonate by cycloaddition reaction of carbon dioxide and epoxy compounds.

Method used

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  • Application of morpholine-containing ionic compound serving as catalyst for synthesizing cyclic carbonate
  • Application of morpholine-containing ionic compound serving as catalyst for synthesizing cyclic carbonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] In 50 milliliters of stainless steel autoclaves, add 9.25g (0.1mol) epichlorohydrin, 0.32g (1%mol) N-methyl-N-dodecylmorpholine ammonium bromide (its preparation is with reference to N- For the preparation of methyl-N-hexadecylmorpholine ammonium bromide, only dodecyl bromide is used instead of hexadecane bromide), the reaction kettle is sealed, and carbon dioxide with a pressure of 0.1MPa is filled, and the temperature is raised to 90°C. Reacted for 24 hours, cooled to room temperature, and slowly released the pressure. The resulting liquid was distilled under reduced pressure to obtain the product 4-chloromethyl-[1,3]dioxolane-2-one—a cyclic carbonate, which was GC-MS and NMR detection, the reaction selectivity is 100%, and the yield is 99.9%. The NMR data are as follows: 1 HNMR (CDCl 3 , 300MHz): δ (ppm): 3.78 (dd, J =3.6,12.3Hz,1H); 3.86 (dd, J =4.9, 12.3Hz ,1H); 4.44(dd, J =5.7,8.8Hz,1H); 4.64(t, J =8.7Hz,1H); 5.02~5.08 (m,1H)

Embodiment 2

[0029] Same as the reaction conditions and detection method in Example 1, only the catalyst used is changed to 0.04g (1‰ mol) N-methyl-N-decylmorpholine ammonium iodide (the preparation refers to N-decyl-N - Preparation of methyl-morpholine ammonium chloride by replacing the chlorine of N-decyl-N-methyl-morpholine ammonium chloride with iodine) to obtain 4-chloromethyl-[1,3]dioxane Pentan-2-one, the reaction selectivity is 100%, and the yield is 98.6%.

Embodiment 3

[0031] Same as the reaction conditions and detection method in Example 1, only the catalyst used is changed to 0.06g (2‰ mol) N-methyl-N-tetradecylmorpholine ammonium chloride (its preparation refers to N-methyl- Preparation of N-hexadecylmorpholine ammonium bromide, only tetradecyl chloride was replaced by hexadecane bromide) to obtain 4-chloromethyl-[1,3]dioxolan-2-one, The reaction selectivity was 100%, and the yield was 99.0%.

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Abstract

Disclosed is a method for synthesizing cyclic carbonates, wherein a compound as represented by formula (I) or formula (II) is used as the catalyst, wherein R1 is methyl or ethyl; R2 is a C10-18 alkyl group; X- is one of Cl-, Br-, I-, BF4 - and PF6 -, and Y- is one of Cl-, Br-, I-, BF4 -, PF6 -, CH3SO3 - and CH3C6H4SO3 -. No organic solvent or cocatalyst is used in the reaction process. The reaction temperature is 50 to 140°C, the reaction time is 1 to 24 hours, the reaction pressure is 0.1 to 0.5 MPa, and the molar ratio of the substrate to the catalyst is in the range of 1000:1 to 50:1. Compared to the traditional synthesis methods, the method disclosed has the advantages of being simple in processes, environmentally-friendly, mild in conditions, high in catalyst activity, high in efficiency, low in energy consumption and free of equipment corrosion.

Description

technical field [0001] The invention relates to the use of morpholine-containing ionic compounds as catalysts for synthesizing cyclic carbonates. Background technique [0002] Due to the continuous consumption of fossil fuels, the content of carbon dioxide in the atmosphere is increasing day by day, and the accompanying many environmental problems have attracted more and more people's attention. At the same time, carbon dioxide is the most abundant source of C1 in nature. How to effectively activate carbon dioxide, fix it and convert it into high value-added products has become one of the most challenging issues in this century. Based on the consideration of atom economy, cycloaddition of epoxy compound and carbon dioxide to generate cyclic carbonate is one of the good conversion pathways, and the product cyclic carbonate itself is a very good polar aprotic solvent. It has important applications in the synthesis of secondary lithium batteries, pharmaceuticals and fine che...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/36C07D317/38B01J31/02
CPCB01J2231/324B01J31/0239C07D295/037
Inventor 周晓海张海波龚青周夏衍
Owner WUHAN IL CHEM TECH
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