Bisamide-substituted novel calixcrown ether compound as well as synthesis method and application thereof

A bisamide and hydrocarbon crown ether technology is applied in the field of organic extractants, which can solve the problems of low distribution ratio, poor fat solubility, low cesium distribution, etc., and achieves the effects of high reaction efficiency, simple purification process and improved extraction performance.

Inactive Publication Date: 2015-12-09
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although 25,27-bis(2-propoxy)-calix[4]arene-crown-6 with 1,3 alternating conformation has good extraction performance for cesium under acidic conditions, the dist

Method used

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  • Bisamide-substituted novel calixcrown ether compound as well as synthesis method and application thereof
  • Bisamide-substituted novel calixcrown ether compound as well as synthesis method and application thereof
  • Bisamide-substituted novel calixcrown ether compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 1

[0026] Example 1 11,23-bis(propionamido)-25,27-bis(2-propoxy)-calix[4]arene-crown-6

[0027] 1) Synthesis of 11,23-bis(nitro)-25,27-bis(2-propoxy)-calix[4]arene-crown-6: 4.26g of 25,27 in 1,3 alternate conformation -Bis(2-propoxy)-calix[4]arene-crown-6 is dissolved in 150mL of acetic anhydride, cooled to -10°C, stirred for 30min, and mixed with 100mL of acetic anhydride, 100mL of acetic acid, and 1mL of concentrated nitric acid. Slowly add dropwise to the above system, continue stirring for 3 hours after the completion of the drop, warm to room temperature, and stir for 12 hours. Pour the reaction solution into 500 mL of ice-water mixture, stir until solid precipitation is complete, filter with suction, and dry. The crude product obtained is recrystallized with a mixed solvent of methanol and ether with a volume ratio of 5:2 to obtain a pale yellow powder solid. Namely 11,23-bis(nitro)-25,27-bis(2-propoxy)-calix[4]arene-crown-6, the yield=93%;

[0028] 2) The synthesis of 11,23-b...

Embodiment 2 1

[0033] Example two 11,23-bis(propionamido)-25,27-bis(2-propoxy)-calix[4]arene-crown-6

[0034] The method for synthesizing white flaky crystals 11,23-bis(amino)-25,27-bis(2-propoxy)-calix[4]arene-crown-6 is the same as in Example 1.

[0035] Add 0.740 g of the obtained white flake crystals to 20 mL of dichloromethane to dissolve, ventilate nitrogen, cool to -5° C., add 0.25 g of propionyl chloride, and add 0.3 g of triethylamine dropwise. After finishing the drop, heat to reflux for 3 hours. After the completion of the reaction, the reaction solution was directly spin-dried under reduced pressure, dissolved in dichloromethane, and washed three times with distilled water. The organic phases were combined, dried with sodium sulfate, filtered with suction, the filtrate was spin-dried, and a small amount of dichloromethane was added to dissolve. The white precipitate is obtained in petroleum ether, filtered and dried to obtain the product 11,23-bis(propionamido)25,27-bis(2-propoxy)-cal...

Embodiment 3 1

[0036] Example three 11,23-bis(butyramido)25,27-bis(2-propoxy)-calix[4]arene-crown-6

[0037] 1) Synthesis of 11,23-bis(nitro)-25,27-bis(2-propoxy)-calix[4]arene-crown-6: 4.26g of 25,27 in 1,3 alternate conformation -Bis(2-propoxy)-calix[4]arene-crown-6 is dissolved in 150mL of acetic anhydride, cooled to -15℃, stirred for 30min, and a mixture of 100mL of acetic anhydride, 100mL of acetic acid and 1mL of concentrated nitric acid Slowly add dropwise to the above system, continue stirring for 3 hours after the completion of the drop, warm to room temperature, and stir for 12 hours. The reaction solution was poured into 500 mL of ice-water mixture, stirred until solid precipitation was complete, filtered with suction, and dried. The crude product obtained was recrystallized with a mixed solvent of methanol and ether with a volume ratio of 5:2 to obtain a pale yellow solid.

[0038] 2) The synthesis of 11,23-bis(amino)-25,27-bis(2-propoxy)-calix[4]arene-crown-6: Take 0.8g of the above...

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Abstract

The invention relates to a bisamide-substituted novel calixcrown ether compound. The general chemical formula of the bisamide-substituted novel calixcrown ether compound is 11,23-di(acylamino)-25,27-di(2-propoxy)-calix[4]arene-crown-6; a synthesis method comprises the following steps: firstly, synthesizing an intermediate of 11,23-di(amino)-25,27-di(2-propoxy)-calix[4]arene-crown-6, and condensing the intermediate and acyl chloride so as to obtain the bisamide-substituted novel calixcrown ether compound. According to the synthesized 11,23-di(acylamino)-25,27-di(2-propoxy)-calix[4]arene-crown-6, the hydrophobicity of an extraction agent is increased by increasing the length of carbon chains of acylamino, the extraction distribution ratio of the calixcrown ether compound, in which acylamino is introduced, to caesium is increased by five times or above at least under the same extraction condition, the extraction performance is improved, the grade of an extraction device in the extraction process is reduced, the separation cost is reduced and the bisamide-substituted novel calixcrown ether compound has a high potential of being applied to removal of caesium ions in radioactive wastewater.

Description

Technical field [0001] The invention belongs to the technical field of organic extractants, and particularly relates to a new type of bisamide substituted calixarene crown ether compound and its synthesis method and application. The new type of calixarene crown ether compound is 11,23-bis(amido)-25, 27-bis(2-propoxy)-calix[4]arene-crown-6. Background technique [0002] Cesium-137 is one of the long-lived fragment nuclides produced in the process of nuclear fuel fission. It mainly exists in the high-level liquid waste produced by the reprocessing of spent fuel. It has the characteristics of high heat release rate and strong radioactivity. If it is separated from the high-level waste liquid, it will not only help reduce the radioactive intensity of the high-level waste liquid, but also reduce the volume of glass solidification, thereby greatly reducing the disposal cost of the high-level waste liquid. Therefore, the development of cesium-137 separation technology is in line with t...

Claims

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Application Information

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IPC IPC(8): C07D323/00C22B3/36C22B26/10
CPCC07D323/00C22B26/10C22B3/304Y02P10/20
Inventor 易荣叶钢陈靖吕大超吴奉承
Owner TSINGHUA UNIV
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