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Preparation and application of amino-functionalized pillar penta-arene stationary phase

An amino-functionalized, column-pentarene technology is applied in the field of chromatographic analysis to achieve the effects of improving thermal stability and film-forming properties

Active Publication Date: 2022-04-05
SHENYANG POLYTECHNIC UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The supramolecular compounds that have been reported to be used in the field of gas chromatography include cyclodextrin, crown ether and calixarene, and the application of columnarene and its derivatives in gas chromatography is rarely reported. At the same time, there is no amino-functionalized columnarene ( P5A-C10-2NH 2 ) as a research report on gas chromatographic separation

Method used

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  • Preparation and application of amino-functionalized pillar penta-arene stationary phase
  • Preparation and application of amino-functionalized pillar penta-arene stationary phase
  • Preparation and application of amino-functionalized pillar penta-arene stationary phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] 1.0g (9.08mmol) 1,4-hydroquinone, 11.70g (39.00mmol) 1,10-dibromodecane, 6.52g (47.18mmol) potassium carbonate and 0.04g (0.15mmol) 18-crown ether -6 was added to 40 mL of 2-butanone, heated to 85°C for 16 hours, cooled, filtered, and the filter cake was washed with 100 mL of dichloromethane. The filtrate was evaporated to dryness to obtain 11.20 g of a yellow viscous crude product, which was purified by column chromatography, and the eluent was petroleum ether:dichloromethane=5:1 (V:V), and intermediate (I) was obtained as a white solid: 1.91 g . m.p.89.9-90.6℃.IR(KBr,cm -1 ):643.84(C-Br), 1036.54(C-O-C), 1216.81(C-O-C), 1438.73(C=C), 1461.43(C=C), 1473.71(C=C), 1508.01(C=C), 2850.71(CH 2 ), 2918.83 (CH 2 ), 2933.37 (CH 3 ).

[0057]

[0058] Add 1.1g (10mmol) 1,4-hydroquinone, 6.85g (31mmol) 1-bromodecane, and 1.74g (31mmol) potassium hydroxide to 25mL ethanol, heat to 81°C for 10h, cool down, pump Filter, and wash the filter cake with deionized w...

Embodiment 2

[0066] The difference between this example and Example 1 is: the reaction conditions are different, and the purification method of step 4 is different

[0067] 2g (18.16mmol) 1,4-hydroquinone, 21.80g (72.65mmol) 1,10-dibromodecane, 12.56g (90.82mmol) potassium carbonate and 0.08g (0.30mmol) 18-crown ether- 6 was added to 70mL of 2-butanone, reacted at 85°C for 16h, cooled down, filtered, and the filter cake was washed with 100mL of dichloromethane. The filtrate was collected and evaporated to dryness to obtain 20.250 g of a yellow viscous crude product, which was purified by column chromatography, and the eluent was petroleum ether:dichloromethane=5:1 (V:V) to obtain intermediate (I): 4.04 g.

[0068] Add 2.2g (20mmol) 1,4-hydroquinone, 13.26g (60mmol) 1-bromodecane, 3.37g (60mmol) potassium hydroxide to 50mL ethanol, react at 85°C for 8h, cool down, and filter with suction , the filter cake was washed with deionized water until neutral. Recrystallize twice (2×150 mL) with d...

Embodiment 3

[0073] This example differs from Example 1 in that: the reaction conditions are different, and the purification method in step 4 is different.

[0074] 2g (18.16mmol) 1,4-hydroquinone, 21.80g (72.65mmol) 1,10-dibromodecane, 12.56g (90.82mmol) potassium carbonate and 0.08g (0.30mmol) 18-crown ether- 6 was added to 70 mL of 2-butanone, reacted at 83°C for 18 hours, cooled down, filtered, and the filter cake was washed with 100 mL of dichloromethane. The filtrate was collected and evaporated to dryness to obtain 20.801 g of a yellow viscous crude product, which was purified by column chromatography, and the eluent was petroleum ether:dichloromethane=5:1 (V:V) to obtain intermediate (I): 4.20 g.

[0075] Add 4.4g (40mmol) 1,4-hydroquinone, 26.52g (120mmol) 1-bromodecane, 6.73g (120mmol) potassium hydroxide to 100mL ethanol, react at 85°C for 8h, cool down, and filter with suction , the filter cake was washed with deionized water until neutral. Recrystallized twice (2×150 mL) wit...

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Abstract

The invention belongs to the field of chromatographic analysis, and particularly relates to an amino-functionalized column penta-arene stationary phase, a capillary gas chromatographic column as well as preparation and application of the amino-functionalized column penta-arene stationary phase and the capillary gas chromatographic column. 1, 4-hydroquinone is used as a raw material, and the amino-functionalized pillarolenepentaarene derivative is obtained through five chemical reactions of etherification, cyclization, amination and hydrazinolysis. A long-chain functional group is introduced to the lower edge of a pillararene monomer, and then a host molecule with higher polymer recognition capability is obtained after cyclization. The pillararene integrates the advantages of the first four generations of supramolecular host compounds, and meanwhile, the film-forming property of the pillararene is improved by introducing a long alkyl chain and amino, so that the thermal stability of the pillararene is improved. The prepared P5A-C10-2NH2 serves as a stationary phase of gas chromatography and shows good separation performance in the aspect of separating compounds such as methylnaphthalene isomers, xylenol isomers, benzaldehyde isomers and halogenated benzene isomers, and the preparation method is simple and easy to implement.

Description

Technical field: [0001] The invention belongs to the field of chromatographic analysis, and in particular relates to an amino functionalized column pentaaromatic stationary phase, a capillary gas chromatography column and its preparation and application. Background technique: [0002] Since the invention of chromatography in the early 20th century, with the continuous development of science and technology, it has become an important part of analytical chemistry. Due to its fast analysis speed, high separation efficiency, high detection performance, good sensitivity, and good selectivity, chromatography analysis has become the most important method in modern separation and analysis science, and has been widely used in life science, material science, and medical science. , environmental science, food science, forensic science and aerospace science and other fields. Gas chromatography is one of the best methods for qualitative and quantitative analysis of complex substances. I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/54
CPCY02P20/55
Inventor 蔡志强黄秋晨孙涛陈若男章围李伟
Owner SHENYANG POLYTECHNIC UNIV
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