Reactions between ethylene oxide and derivatives of ethylene oxide and CO2 for generating cyclic carbonate from

A technology of cyclic carbonate and ethylene oxide, which is applied in the chemical industry, can solve the problems of difficult industrial production and long reaction time, and achieve the effects of short reaction time, high reaction yield and good repeatability

Inactive Publication Date: 2015-03-18
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Description
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  • Application Information

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Problems solved by technology

It is worth noting that most of the reaction methods that have been reported so far require relatively harsh reaction conditions such as high temperature and high pressure (5-9MPa, 155-200°C) and long reaction time, making it difficult to carry out industrial production, and ethylene oxide at room temperature The bottom is gas, easy to polymerize, therefore, improving the reaction yield and product selectivity, improving the reaction conditions so that it can be used in large-scale industrial production is the key problem that needs to be solved urgently.

Method used

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  • Reactions between ethylene oxide and derivatives of ethylene oxide and CO2 for generating cyclic carbonate from
  • Reactions between ethylene oxide and derivatives of ethylene oxide and CO2 for generating cyclic carbonate from
  • Reactions between ethylene oxide and derivatives of ethylene oxide and CO2 for generating cyclic carbonate from

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Taking CMP-Co as a catalyst to catalyze the reaction of ethylene oxide and carbon dioxide as an example to explore the influence of reaction conditions (temperature, pressure and time) on the reaction yield. The structural formula of the product was characterized by NMR. 1 H NMR (ethylene carbonate, 400 MHz, CDCl 3 ):δ=4.2(t,4H); 13 C NMR (400MHz, CDCl 3 ): δ=63.3,155. ( 1 H NMR and 13 C NMR spectrum see figure 1 and 2 ).

[0049] ① 100mg CMP-Co, 400mg tetrabutylammonium bromide; 1.1g ethylene oxide, carbon dioxide at room temperature for 48 hours, the yield of ethylene carbonate was 78.2%;

[0050] ② 100mg CMP-Co, 600mg tetrabutylammonium bromide; 1.1g ethylene oxide, carbon dioxide at room temperature for 48 hours, the yield of ethylene carbonate was 81.2%;

[0051] ③ 100mg CMP-Co, 600mg tetrabutylammonium bromide; 1.1g propylene oxide, carbon dioxide pressure 1.0MPa, 40°C for 12h, the yield of ethylene carbonate was 84.5%;

[0052] ④ 100mg CMP-Co, 600mg tet...

Embodiment 2

[0060] Taking CMP-Zn as a catalyst to catalyze the reaction of ethylene oxide derivatives and carbon dioxide to generate corresponding cyclic carbonates as an example. Table 2 shows the structures and reaction yields of oxirane derivatives and corresponding cyclic carbonates.

[0061] ① 50mg of CMP-Zn, 600mg of tetrabutylammonium bromide, 5.46ml of 1,2-epoxydodecane, and a carbon dioxide pressure of 3.0MPa were reacted at 120°C for 2h to obtain the product (a) with a yield of 91.6%. 1 H NMR (400MHz, CDCl 3 ),δ=4.43-4.70(m,1H),4.01-4.44(2,2H),2.82-2.89(m,2H),2.68-2.63(m,2H),2,35-2.42(m,2H) ,1.60-1.79(m,2H),1.30-1.54(m,8H),0.75-0.89(m,5H). 13 C NMR (400MHz, CDCl 3 ), δ=155.31 (C=O), 77.31, 71.26, 52.58, 47.28, 34.14, 32.76, 32.13, 29.55, 26.23, 24.64, 22.93, 14.33. Spectrum see image 3 and 4 .

[0062] ② 50mg CMP-Zn, 600mg tetrabutylammonium bromide, 3.32ml glycidol, carbon dioxide pressure 3.0MPa, react at 100°C for 1h, and the yield of product (b) is 91.2%. 1 H NMR (4...

Embodiment 3

[0073] A class of metal-complexed conjugated microporous polymers provided by the present invention catalyze the reaction of ethylene oxide and its derivatives with carbon dioxide to generate cyclic carbonates. The reaction conditions used are also applicable to 1,2-epoxycyclohexane Alkanes and the reaction of 1,2:7,8-dioxoctane with carbon dioxide.

[0074] The following uses CMP-Cr as an example to illustrate the reaction process of these two compounds with carbon dioxide. Table 3 shows the structures of these two compounds, the structures of the corresponding cyclic carbonates and the reaction yields.

[0075] ① 50mg CMP-Cr, 600mg tetrabutylammonium bromide, 5.06mL 1,2-epoxycyclohexane, carbon dioxide pressure 3.0MPa, reaction at 120°C for 12h, the yield of product (j) was 66.3%. 1 H NMR (400MHz, CDCl 3 ),δ=4.63-4.68(m,1H),1.75-1.95(m,2H),1.31-1.65(m,2H). 13 C NMR (400MHz, CDCl 3 ), δ=155.68 (C=O), 76.07, 26.98, 19.38. Spectrum see Figure 19 and 20 .

[0076] ② 50m...

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Abstract

The invention discloses reactions between ethylene oxide and derivatives of ethylene oxide and CO2 for generating cyclic carbonate. According to the reactions, metal complexed conjugated micropore high-molecular polymers (CMP-M) of one type are taken as main catalysts and quaternary ammonium salts (such as tetrabutylammonium bromide, tetrabutyl ammonium chloride and tetrabutyl ammonium acetate), triethylamine and 4-dimethylamino or potassium iodide are taken as catalysis promoters. The reactions disclosed by the invention are characterized in that the molar ratio of the ethylene oxide and the derivatives of the ethylene oxide to the catalyst promoters and the catalysts is (500-2000):(1-50):1, the reaction temperature is 0-120 DEG C, the reaction time is 1-24 hours, and the reaction pressure is 0.1-3MPa. The limit of high temperature and high-pressure (6-9MPa and 160-200 DEG C) to similar reactions in prior art is broken through, and the yield of cyclic carbonate can be up to 29-99% under gentle conditions. The reaction has the advantages of short reaction time, gentle reaction condition, high reaction yield, good reaction repeatability and the like, and the possibility of industrialization is improved.

Description

technical field [0001] The invention belongs to the field of chemical industry, in particular to a class of ethylene oxide and its derivatives and CO 2 A reaction to form a cyclic carbonate. Background technique [0002] CO 2 Gas is the most important greenhouse gas in human activities. With the increasing severity of the greenhouse effect, people have paid more and more attention to the treatment and absorption of carbon dioxide. Current reduction of CO in the atmosphere 2 There are two main categories of methods: the development of new and efficient CO 2 Separation and recovery technology, CO 2 Storage technology, CO emission reduction from stationary and mobile sources 2 Process technology, energy efficiency improvement and new energy technology, etc.; utilization of CO 2 As a chemical product or material with high value-added synthesis of carbon resources, it is of great significance to the development and progress of our human beings to fix it or convert it into ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/36C07D317/38C07D317/46B01J31/22
CPCC07D317/36B01J31/1691B01J2231/72B01J2531/0238C07D317/38C07D317/46
Inventor 邓伟侨杨瑞霞
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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